31 Days of Hot Sex

Ok! this goes to couples who want to improve their  Sex life…Your comment will be review for our coming Topics

Challenge 1

 Slip a doughnut around his penis, and slowly eat it off.

Let me preface this by saying that D. does not have a small package. On a scale of one to porn star, I’d rate him about a seven. I only share this because I don’t want you getting the wrong impression when I tell you what I’m about to tell you.

I used a “donette”. In case you’re not familiar with doughnut varieties, this is a miniature doughnut, about one-quarter the size of regular ones, and is usually sold in grocery stores or 24-hour stores and comes in a pack of five or so. In other words, this is not the doughnut that Cosmo had in mind. But I was determined to do this challenge first (basically I was just really craving a doughnut and I figured the calories didn’t count if it was for “work”) and those were the only kind I could find.

While D. and I got ready for bed, I informed him very matter-of-factly, “I’m going to slip a doughnut around your penis and eat it off.” Since he’s seen the list of 31 challenges, he had been prepared. He was not prepared for the donettes, though.

“Uh, that’s not going to fit around me,” he said.

“We’ll make it work,” I responded.

I pushed him down onto the bed, grabbed a donette from the package (which I had slyly hid on my night table), pulled down his boxers, and…placed the donette on the tip of his hard penis. (Who knew you just have to mention oral sex and doughnuts to get a guy revved up in no time?) I don’t know how to describe it besides that it looked like a little hat. And really, nothing’s sexier than a peen with a beret on, right?

I broke the donette in half and holding it around the base of the penis. I alternated licking the dessert and D. Then I took a bite of the doughnut and D.’s whole body went tense. Had the doughnut been bigger, I think he would have felt more comfortable, but he didn’t seem to enjoy seeing my teeth so close to his member.

I ended up removing a piece of the doughnut and eating it then going back to oral. Which felt a little weird. More like a snack break than a sexy way of incorporating food into foreplay. On the other hand, I’ve never given a tastier BJ. And D. freaking loved it. He said it made the whole experience just feel different and like he didn’t know what to expect next. If you have an oral formula and don’t mix up your style much, I definitely recommend this. Even if the main oral event is the same as usual, using food during the foreplay part of it forces you to go at a different pace and use different techniques.

After we finished and we were just chilling in bed, D. reached for a donette and said, “Mmm junk food.” (At least he didn’t sing, “It’s my dick in a doughnut” to the tune of “Dick in a Box”…oh wait, he did that too.

Challenge 2

 Squirt some lotion on his chest and stomach, then rub it in using nothing by your bare breasts. Don’t stop till all the lotion is absorbed.

If my boobs had a resume, the “Special Skills” section at the bottom would now read:

-Proficient in getting free drinks

-Accomplished in titty-effing

-Ability to one day produce milk

-Adept at making dresses and tops look sexier

-Trained in massage therapy

OK, “trained in massage therapy” might be a bit of a stretch (hey, who doesn’t exaggerate on their resume?), but my tatas have talent!

I was going to go with another challenge today, but after D. and I showered post-gym, he complained that his skin was really dry and reached for the lotion. “No! Don’t!” I yelped, startling him. “I mean, I’ll do it! For you! With my boobs!”

(Sometimes I think D. and I should keep a notebook filled with all of our weird out-of-context quotes. Or who knows, maybe D.’s roommate already does. It could be a blog: WTFDidMyRoommateAndHisGFJustSay.com.)

I reminded D. that using my breasts to apply lotion to him was on our Cosmo to-do list and obviously, he was thrilled. He lay down on the bed naked and I brought the bottle of lotion over. Instead of squirting it on his body, I put it directly on my breasts (bonus: it was chilly and made my nips perky) then straddled him and leaned down.

Aaaand he squealed. And not out of delight. Because it was cold.

“Oh come on,” I said, not at all sympathetically. “You’re getting a fun-bags massage so you’re not allowed to complain.”

After a few more seconds, the lotion felt significantly warmer and D. went from tensing all of his muscles to relaxing. I felt slightly strange moving my breasts in circles over his torso and chest, but maintaining eye contact kept it feeling sexy, not silly. I also found it helpful to get on my hands and knees and arch my back to make my torso touch his. Much hotter then laying flat on him and just rubbing around, which I may or may not have done at first until D. laughed at me and said, “That’s not how it’s done.” Which begs the question: How many times has he had this done to him?

D. ended up flipping me over so he was on top. And the massage/lotion application quickly turned into a happy ending. For moi. And that’s when I realized the best part about using my breasts to apply lotion to D. It meant that there wasn’t any lotion on my hands or his. And if you’ve ever been manually stimulated by a guy who has anything on his hands (lotion, cologne, hot sauce, whatever), then you know this is a major bonus. (I’ve definitely gotten irritated vadge from a guy who had hand lotion on. And I have a friend who got what she called “Bear Claw Vagina” after some guy went to town on her nether regions without properly washing the aftershave off of his hands.)

So now, I’m satisfied, well-moisturized, and not suffering from Bear Claw. All in all, I’d say it was a successful challenge.

Is your guy a boobs man? How do you “involve” your breasts in hookups? Have you ever had a hookup-turned-disaster, like my friend’s aftershave incident?

Challenge 3

naked guy in shower
: While he’s showering, ambush him without saying a word, get on your knees, and take him in your mouth.

If I didn’t know any better, I’d think D. was in cahoots with the editors over at Cosmo who are coming up with these challenges. Because if D. were to list his favorite sexual acts, a shower beej would probably make the top 10.

We hook up in the shower fairly regularly so I decided to put a little twist on the challenge to make it more interesting for us. Instead of getting in the shower with D., I simply pulled back the curtain, knelt outside the tub, and went to work. (OK, this may or may not also have to do with the fact that I had just gotten a blowout and didn’t want to get my hair wet.)

D. had gone to the gym earlier so I gave him ample time to, you know, wash his business before I ambushed. (I don’t know about you, but I made the mistake of doing oral on an ex post-workout and it was not a pleasant experience.) I stealthily sneaked into the bathroom and pulled the curtain aside, flashing him a smile.

I reached for his junk then put my mouth on it. Then something surprising happened. He let out these really loud moans. I’m talking, Is something wrong? Should I stop? type of moans. He’s not usually incredibly loud when we hook up, and definitely not right at the beginning. (D.’s more of a quiet moaner throughout and a “Ohhhh S.” guy during climax.) I was taken aback, but I kept going because—get this—his toes were curled. And I heard from a friend once that guys curl their toes when they’re either super aroused or about to climax.

And my instincts were right! He was loving it.

And I have to say, I was loving it too. One thing I like about giving oral in the shower is that the water helps keep things slick. So I can get one hand involved without any risk of chafing. (Aside: if you’re going to give an HJ in the shower, I highly recommend using conditioner as lube.)

I did the one-hand-and-mouth technique for a little while then resurrected an old tip I once read in Cosmo about treating the guy’s penis like an ice cream cone. Yeah, yeah, it sounds a little weird and cheesy, but it gets a great reaction. Hold onto his equipment with one hand and swirl your tongue around the tip. I alternated doing this and putting it in my mouth, and judging by D.’s continued moans and groans, it was a hit.

He finished and his legs were so shaky that he had to lean against the wall. (Or maybe that had something to do with him working out earlier, but I’m gonna take the credit!) I asked him later if it was perhaps a particularly good BJ. I didn’t want to embarrass him by alluding to the abnormally loud moans, but he knew what I was saying. He told me it was just such a great surprise.

Sure, anticipation is great. But in the words of D., so is “getting into the shower thinking the most exciting thing you do in there will be exfoliating your face, only to find out you’re gettin’ head”. Wise words, D., wise words.

What’s the craziest place you’ve ever gone down on a guy? And what is your boyfriend/husband’s sex soundtrack, ie what noises does he make during hookups?

Challenge 4

naked couple kissing

Have him enter you while you’re sitting on a table or counter and he’s standing up in front of you.

After a girls-only night out that involved almost as many bottles of wine as people, I showed up at D.’s place on a mission. To eat a frozen pizza. (Thought I was going to mention the challenge, didn’t you?) After accomplishing that mission, I moved on to the challenge (determined by me earlier in the day, unbeknownst to D.) I showered then called D. Into the bathroom and planted a kiss on his lips. After first basin’ it for a while, I hopped up onto the ledge of the sink and pulled him between my legs and reached for his crotchal region.

I undid his pants then hopped off the ledge and got on my knees. Man, that bathroom is seeing a lot of oral action recently!

I took him in my mouth and when he was hard, resumed my perch atop the sink. D. reached between my legs and proceeded to majorly tease me. Finally I just grabbed his butt and pulled his whole body toward me.

“I want you inside me.” (Note: this is a great line if you’re hesitant about sounding raunchy when you dirty-talk. Hot, but not nasty.)

D. obliged, but the thrusting was slightly awk. I ended up placing my hand next to my butt to brace against his pumping. Otherwise I would have fallen back into the sink.

The angle was awesome, though. All the benefits of standing up sex without the balance/muscle fatigue/oh-god-am-I-too-heavy-for-him concerns. If this were Amazon, this would read; if you like sex up against the wall we think you’ll love sex on a sink!

I also found that if I let my legs dangle a little, as opposed to wrapping them around D.’s waist, I got some nice C-stimulation.

But alas, not enough to climax. Maybe it was because I’d been drinking, but I just felt like I was gonna need a serious time commitment in order to get there. And—I’m a little embarrassed to admit—I wasn’t willing to put in the time.

On the upside, I found a new sex spot around the apartment. And one that’s super easy to, ahem, clean up afterward!

What are your thoughts on standing-up sex? Have you or would you try this variation? Besides the bedroom, what room do you most frequently hook up in? And lastly, do you ever find it difficult to climax after drinking?


Challenge 5

 Announce to each other throughout the day—by text, on the phone, or in person—every time you feel horny.

Had I known that was going to be the challenge for the day, I might not have been so baffled when I received the following email from D. But since we hadn’t discussed a challenge.

I made a reservation at [name of restaurant] for 8:30. And also, I’m kinda horny right now. I thought you should know.

I probably spent a good 20 seconds just staring at what he had written. Why is he telling me? I thought. Is he, like, going to jerk off right now and wanted to let me know? Did he have a Freudian slip and type “horny” when he meant to say “hungry”? I could not figure out what the hell his email meant.

Then a lightbulb went off. The list of challenges! Horny announcements! He had initiated a challenge!

I called him and barely managed to get out a “Me too” before having a laughing fit.

D. explained that he had found the list on his bookshelf that morning and chosen this challenge.

For the rest of the day, we exchanged emails and texts, written as if they were breaking news updates. “Just in: S. is turned on.” “Horny,” texted D. followed by another one not 30 seconds later. “Update: still horny.”

As you can tell, we were treating it more like a joke than actual sexy foreplay.

When we got to dinner later, though, I could note the benefits of having done the back-and-forth. Simply, we both knew we were having sex that night. Not that it was such a rare occurrence for the two of us to have sexy time on a Friday night after a dinner out, but something about knowing we would definitely do it was hot. I almost felt like I was on a second or third date with a new guy and we both knew we’d end up hooking up that night. So it becomes all you can think about.

Well, it also was all we could think about because we continued to the texting through dinner.

I went to the bathroom after ordering and texted, “Wanna have sex with you right now.

When I got back to the table, D. had a huge grin on his face. And upon checking my phone a few minutes later, I saw a response: “I’m with you. Maybe we should wait till after dinner?”

Well, after dinner we walked back to my apartment and made out the whole way back. I’m not a huge PDA person and neither is D., but what can I say? The sexting (if you can even call it that) had us feeling all in lurv. Well, I think it had D. horny, but something about how funny D. is and how on the same wavelength we are gave me the warm and fuzzies.

And what do you get when you combine horniness and warm and fuzziness? Very good sex. It was missionary and very intimate. Fairly quick. Vanilla, but delicious. And if we’d continued the texting, the exchange might have looked something like this:

S.: Update: No longer horny. Just satisfied.

D.: This just in: Me too


Challenge 6

couple about to have sex

Have a 15 minute orgasm, following the instructions .

Editor’s note: Today’s challenge was “crashed” into the blog. In other words, it wasn’t on the original list of to-dos we sent S. But when we learned about the 15-minute-orgasm, we just had to ask her to try it out. If you want to try it (and uh, why wouldn’t you?), send this to your man.

I wish I could say that my first thought when I was asked to do this challenge was: Bring it on. Or, Can’t wait! But if I’m being totally truthful, my first thought was: Bullshit.

Then I read some of the comments on the article Cosmo ran and realized that maybe this was a real (read: possible) thing. And while I was doubtful that I’d be able to get my O on for a quarter of an hour, I knew I had to try.

And ready for this? It effing worked. Not 15 minutes, but waaaay longer than usual. And probably longer than ever before. But I honestly have no clue how long it went on for because I was, like, in some weird pleasure haze. Ew, pleasure haze sounds like some bad 70s porno. You know what I mean, though.

You can check out all the instructions here, but basically D. just found my sweet spot. Just to the left of my clitoris and he used a really light touch. He did circular motions really softly then pulled away slightly so he was barely touching me. Then he would go back to caressing the whole clitoris. Then back to the sweet spot. And—like the good receiver that I am—I made sure to let him know exactly when he hit it. By moaning. Loudly. And repeatedly. Using his name. It’s all about the positive reinforcement, ladies. Like when your dog learns to sit. Or, you know, when your boyfriend finds a special spot on your hoo-ha.

The climax was like nothing I’ve ever experienced. It just freaking lasted. It wasn’t a really strong orgasm at first. Normally, I climax sort of fast and hard then the moment passes. Which is nice and good for busy days. But this was really different. It started off barely noticeable then slowly built from there. And I almost didn’t realize it was happening at first.

But here’s the crazy thing (and also the reason I am so madly, crazily in lust with my boyfriend): I never told D. about the new challenge. I’m not kidding you. In fact, I was sort of putting it off, thinking we’d do it next weekend…or later. I just wasn’t ready to “fail” so early in the blog.

And when he started to manually stimulate me, I did not expect it to turn into a long O or be anything different than the usual. But it went on. And on. And on. I could not believe it.

I think I know what happened. I have a feeling D. has been going on cosmopolitan.com. (Now that he’s allowed to read the blog—unlike with 77 Positions—he’s been checking out the site more.) And I bet he saw the article Cosmo put up and learned the moves. I’ll find out and let you all know!

In the meantime, I want to know if you’ve ever had a long orgasm. How did you get that to happen? Also, what’s the best orgasm you’ve ever had. Describe it below!

Challenge 7

python sex position

Go through your getting-ready routine totally naked in front of each other. Wash your face, make breakfast—but don’t put on clothes till right before you walk out the door.

So, D. and I now spend pretty much every night together, about half the time at his place and the other half at mine. It’s definitely getting to the point where I can imagine myself living with him. How different can it really be from what we’re doing? (Every time I think that, I imagine all of my living-together couple friends saying, “It’s sooo different.” And I know it is, but I wanna know how!)

Anyway, the point of all that (besides the fact that I selfishly want to get all of your thoughts on the topic!) is that D. and I have definitely fallen into a morning routine. And none of it involves staying naked for very long. In fact, my entire morning is essentially one long boner killer.

For starters, I wear boxers and a tee almost every night. I know, I know! Bad bad bad. But at least they’re not sweats, right? Or pajama jeans. Then I immediately get dressed. So D sees me for a total of, oh, 45 seconds without clothes on. And then he often is forced to watch me put on tights, officially the unsexiest act a woman can do.

So I was excited for this challenge. And D. was probably thanking the Cosmo gods.

When the alarm went off, I got right up and stripped down. And just as the challenge required, I started going through my routine. I checked my email, did my hair, put on makeup, all while D. watched with a puzzled but pleased look.

Then he got up and followed suit. Which is to say, instead of putting on his business suit, he donned his birthday suit.

As soon as I knew he knew what was going on, that was it. We both knew morning sex was going to happen.

But I was determined to draw it out. I walked to the kitchen and poured myself some coffee. (Hey neighbors across the way, you’re welcome.)

But D. dragged me back to the bedroom and threw me down on the bed. (There’s no doubt men’s favorite time to have sex is the AM. Cock-a-doodle-do.)

He started kissing my breasts and my neck. Sigh. Then he pushed my legs apart and went to town manually. Double sigh.

I turned over and angled my butt toward him, which as we all know is the universal signal for, “Let’s do it like doggies”. D. gently entered me. (I always find the first thrust in this position a little uncomfy—am I the only one?—so I need it to go slow.)

I arched my back, which sent D. into a moan-fest. Not sure if it’s about the angle or the fact that he gets a better view of my butt, or that it makes him think I’m more into it, but D. freaking loves the curved back during doggy.

He reached around and rubbed my clitoris until I finished. So hot. Especially knowing that every time I involuntarily bucked my hips during orgasm, D. felt it.

He kept thrusting away. For a while. And then a while longer. Then I started to worry about the time. Then I really started to worry about the time.

And then I sort of voiced my concern to D.”How are you…doing?

“Great.” [Pause.] “I’m not really sure what’s going on. But this feels great.”

But the way he said great wasn’t too convincing. So we changed positions. I got on top and within a minute, he finished. I’m not sure what that was about. Usually he freaking loves doggy style. But it just seemed not to be working. Maybe he was just more in the mood for lay-back-and-do-nothing sex (ie, girl-on-top) or maybe he just needed to look at my pretty face to finish. Kidding. I think it’s probably the former.

Have you ever experienced something similar, in which the guy doesn’t climax for a looong time in one position then you switch it up and all of a sudden—bam? Also, what’s your favorite time of day to hook up? And your guy’s favorite time?

Challenge 8

couple eating ice cream naked
  Give yourself a whipped cream bikini and let him lick it off of you.

Actual Gmail correspondence:

Subject: the best shopping list you’ve ever received

To: D.

From: S.

Will you pick up condoms and whipped cream? They may or may not have anything to do with each other.

Re: the best shopping list you’ve ever received

To: S.

From: D.

Haha that is quite a list. I also picked up a rubber chicken, a pulley, and a power drill. They may or may not have anything to do with this.

Not super spontaneous, I know. Doing it Varsity Blues style, where I surprise him by walking out in nothing but a whipped cream bikini would have been way hotter. But I wasn’t going to have time to stop by the store and I really wanted to try this challenge. (My eagerness to do it that day had something to do with the fact that I was feeling good about my body after a super hard gym class that seriously worked by ass and thighs. And hey, you gotta strike when the iron is hot. Or rather, you gotta wear a whipped cream bikini when your body is hot.)

The bad news is that we didn’t get to it that night. We were both exhausted. We had dinner, zonked out in front of the TV, and went to bed. Though at least I opted for cute boy shorts and a not-hugely-baggy tee!

The good news is that last night, I got to my place and as soon as I walked in the door, received a text from D. saying he would be there in 20. And the roommate was out of town! So I decided I was going to greet D. at the door in my homemade lactose swimsuit and give Ali Larter a run for her money.

I did a lazy girl’s shower, which is to say I used wipes to clean off my entire body. Hey, if I were going to feast off of someone’s body, I would appreciate it if he took the time to make sure the eating area was hygienic. Then I waited for D. to buzz the downstairs door. A few minutes past and I found myself a little nervous. (Remember that episode of SATC where Carrie worries that she and Aidan are getting too comfortable and she misses the stomach flip that comes with new, uncertain relationships. Then she manages to make her own stomach flip? Well, not like this was some big relationship moment, but I have to say the butterflies in my stomach felt kind of nice. It reminded me of how I felt early on in our relationship, when I was anticipating a hookup.)

Then he buzzed. I pressed the button to let him in the downstairs door, knowing that the elevator would take at least 45 seconds. In that time, I quickly sprayed on a top (more like pasties) and a bikini bottom, which was really just a triangle of whipped cream that covered the upper part of my crotch. (Don’t wanna get it too close to your vadge, ladies.) I was just finishing up my work of art when D. knocked on the door. I unlocked it then stood back.


He said that a few more times while I tried to look sexy, but probably just had this stupid grin on my face.

D. leaned in for a kiss. Then, as if he realized he was going about this all wrong, he planted his mouth on my nipple and didn’t come up till he had finished that entire half of the “bikini”. (Sidenote: Could asymmetrical one-boob-coverage bathing suits be the next fashion trend? If so, I want the credit.) He did the same with the other side then began licking off the bottom.

He mostly just focused on the creases where my legs meet my torso since I didn’t want to get whipped cream all up in my business. But it was super hot since it forced his down-south kisses to be purely teasing.

After all of that tongue action, I was ready for the real deal. So we hopped in the shower. (Cosmo doesn’t tell you this, but a whipped cream bikini leaves you very, very sticky.) And the below-the-neck kisses continued. But not for long because I was in the mood for sex. Not oral, but straight up P in the V sex. We faced each other and D. held up one of my legs as he entered me.

D. finished before me, but I was sort of OK with stopping right after that. We had left the water on and it was washing away all of the natural lubrication I had going on, which made the sex a tad uncomfortable toward the end.

D. raved about the bikini for the rest of the night. And even though it was on the Cosmo challenge list and he had to have known it was coming, he kept saying things like, “It’s so awesome you did that.” I think that translates to: girlfriend points, earned.

Would you ever try this challenge? Have you ever involved any other food (besides doughnuts, donettes, and whipped cream)? If you’ve never done it before, go for it tonight and report back tomorrow!

Challenge 9

 Put a condom on him using your mouth.

Bet you were wondering why I asked D. to pick up those condoms along with the whipped cream the other day? Well, um, clearly it was so I could roll on a love glove using just my mouth!

D. and I don’t usually use condoms, except when I forget to take my pill or when we need a little help in the lube department. (I know, I know—it’s ridiculous to use a condom for lube instead of just buying a bottle, but for some reason I am not all that eager to jump on the lube bandwagon. I promise I will soon, though. Especially since the May issue of Cosmo offers up some very fun ways to incorporate the slick stuff.)

So, last night I stepped out of the shower and walked into D.’s room, where he started kissing me. Wet, open-mouth, hard kisses. If these kisses could talk, they would have said—no shouted—I want to eff you. These were not lovemaking kisses, they were banging kisses. D. removed by towel and led me to the bed, where he pulled back the covers. I wanted to remind him that we’d be using a condom, which meant we could do it anywhere, including on top of his duvet cover, and not worry about cleanup. But I decided to keep my mouth shut. Not exactly dirty talk.

Before laying me down, he turned me so I was facing away from him and reached around with his right hand, which he slipped between my legs. He groaned as soon as he felt that I was already wet. Thank the eff-me kisses for that! And like clockwork, I felt him start to go hard against my butt.

I turned my head around then whispered in his ear, “I want you inside me. Let’s use a condom.”

Now let me pause to say that D. has never complained about using condoms. He swears he doesn’t notice a huge difference. And I don’t think he’s saying it just because he thinks it’s the right thing to say. He’s never had an issue getting off when he’s wrapped. And it doesn’t seem to take him significantly longer either. That said, we’ve had stints in the past when I’ve taken a break from the pill and we’ve had to use condoms regularly. And whenever I go back on the pill and we stop using condoms, he always raves about how amazing it feels to be inside me, with nothing between us.

Basically, D. may not be condom’s number one fans, but I don’t he was all that bummed we were using a condom. And in fact, I think he was looking forward to the challenge. Hey, what guy wouldn’t enjoy an activity that involved his junk and a girl’s mouth, even if there were a condom in the mix?

First, I placed it on the tip using my hands. But like an amateur I forgot to squeeze the tip to get the air out (major no-no since it can cause the condom to break). D. corrected my mistake then I continued. I got it past the ridge then placed my lips around his shaft and basically just pushed against the rolled up condom.

I was planning to just roll the whole thing on, but—Oh. My. God—the taste! I felt like I was eating…well, a condom! I improvised by pulling away for a moment and licking his balls while I used my hand to roll the condom on a bit more. Then after I prepared myself for the taste, I put my mouth around his member again and pushed the condom on until it was fully unrolled.

And then I immediately turned around because there was no way I was kissing D. with that taste in my mouth!

Which meant we were doing it doggy-style. I got on hands and knees on the bed and D. entered me. The lights were still on, which made me a tad self-conscious about D. having a prime view of my rear, but I appeased that anxiety by turning my head around and making eye contact with him. We kept our eyes locked until he came. And when he did, he leaned forward so he was on top of me. I flattened my body out so I was no longer on my hands and knees.

After a few seconds I whispered, “Mmmm, that was—”

“I’m not finished yet!” D. blurted out and he proceeded to shake and groan some more.

I had to stifle a laugh.

Later, after he had disposed of the condom, he sat down and looked at me as if he had something serious to say.

“So, I have an observation,” he said. (Aww, he knew I was going to blog about it so he wanted to give his two cents.) “You ate off all of the condom’s lube!” he exclaimed as if he had just discovered the next Twitter.

He explained that he had absolutely noticed a difference in how the condom “moved against the inside” of me. Interesting, right? It must have all come off in my mouth.

Do you and your guy use condoms? Do you have any tricks for making them feel more sexy and fun? Have you ever used your mouth to put it on him?

Challenge 10

couple kissing
 Do nothing but kiss each other above the waist—on the lips, ears, neck, nipples, shoulders, etc.—for a full 30 minutes.

I remember back when I was in high school—and still a virgin—I was obsessed with making out. Not that I was doing it a ton, but I just loved the idea. Then at some point making out turned into simply a precursor to sex. Sigh. Gone were the days of liplocking with a guy for 30 minutes (shout out to Sam!). I was slightly devastated and I swear to god, I remember thinking, “Will I never just make out with a boy again? Will I never make out with my future husband?”. Soon after, I realized how great sex was and this fear was slightly appeased.

But the 15 year old S. still rears her makeout-loving head.

So you can understand why I was so excited for this challenge.

I told D. the plan. (I recommend you do the same since letting him know midway through could find you guilty of blue balling in most states.)

We lay down on my bed and started slow. Kisses with no tongue, just our lips pressed together. Then open mouth, but unlike some of my first kisses, D.’s tongue didn’t dart into my mouth.

Then he placed both hands on my cheeks. Swoon. Men, if you’re reading this, take note: both hands on the cheek is the fastest way to make a girl melt.

D. got on top of me at this point, but I pushed him off. We had to take this slooow. I leaned over him and started kissing everywhere but his lips. Cheeks, eyelids, nose, neck.

He retaliated by latching on to my lower lips and sucking.

H. O. T.

I definitely felt myself getting turned on so I pressed my body against his. He was definitely packing. But I refused to let that change our course of action.

We started Frenching. Yes, I said Frenching. First, he ran his tongue over my lips length-wise then pried them apart. Totally middle-school dance style!

Once he was in (weird to use that phrase in this blog and not be referring to sex) we totally went at it. Full on heavy gotta-have-you-now, only-one-minute-left-of-seven-minutes-in-heaven making out. He pinned my arms above my head and placed himself over me.

And then, ladies, I’m not embarrassed to say we dry humped. I spread my legs and he rubbed himself against me.

We may have been bending the rules a bit, but it was pretty damn awesome. The kissing continued as we gyrated. And I came close to climaxing, but it didn’t happen. D. kept trying to get in my pants, but I resisted and I can tell he found it totally hot.

After what I’m guessing was about half an hour we stopped. Not because we wanted to. But because we had to. Otherwise, the whole thing would have turned into sex. I made a deal with D. that we would put it on pause then come back to it later.

We untangled ourselves from each other and went to the living room, where we watched exactly half an hour of TV. Then it was back to the bedroom where we finished up—doing things I never would have considered doing during a high-school seven minutes in heaven session. You’ll have to wait till tomorrow to find out exactly what we did. But here’s a hint: D. got 360-degree views of me.

Describe your absolute hottest kiss. And let me know how frequently you and your boyfriend/husband make out without it leading to something more. Have you ever come close to climaxing from dry humping?

Challenge 11

  Do a Dirty 360. Get into girl-on-top, and spin all the way around without pulling away.

I told you in the last post that D. got a 360 degree view of me. Well, I wasn’t totally honest. It was more like 330 degrees. And then I fell off.

But I’m getting ahead of myself.

So, D. and I were in bed, all over each other. Within just a few seconds he had his hands between my legs. He did the whole teasing thing by touching everywhere but the target—thighs, leg crease, lower abdomen. Then he went for it, using the techniques he must have learned reading this article on the 15 minute female orgasm. (Thank you, Cosmo!) Then D. took my hand and put it on his junk.

(What are your thoughts on this move, ladies? D. almost never does it (and thankfully, he’s never ever done the push-my-head-down move as a not-so-subtle way to get head). But it definitely gave me pause.)

Regardless, I took the hint and started to give him a hand job. And after a few tugs D. whispered in my ear, “I want you so bad, S.” I took that not-at-all-subtle hint and climbed on top. I rested my hands on the wall behind D.’s head and hovered just over D.’s shaft, being a big ol’ tease.

It worked. He got all riled up and eventually just grabbed my shoulders and pulled me down so he was completely inside of me. (D. was clearly in a slightly aggressive mood! And I liked it!) I leaned down so my torso was parallel to his, kissed his ear then murmured, “Think we can do a 360?”

D.’s face lit up like a Christmas tree. I’ve never done this with him (or anyone else, for that matter) and I have to admit I was wondering if he even would even find the challenge appealing.

Then something hit me: I had absolutely no effing clue how I was going to spin all the way around. Would my feet be in his face? Would D. fall out? Would I stay in reverse cowgirl for a little bit then continue on my circuitous journey or just do the spin in one motion?

Luckily D. took control of the situation. He moved my left leg so that it was straight out in front of me then crossed it over his chest. (Word to the spinners: make sure your feet are clean for this challenge because he might get a face-full.) My torso and right leg followed the lead and soon I was facing sideways and somehow we had not lost down-there contact.

We stayed in this position for a little while (my hands were behind me supporting my weight so I sort of looked like a crab) because it felt so damn good. D. was thrusting and the angle was something I’d never experienced before. It was shallow penetration, but I remember reading that there are a ton of nerve endings right at the entrance of the vagina that often get overlooked. So maybe that’s why I was enjoying the position so much.

But you know what they say: the spin must go on. Plus, I was afraid D. would finish if we kept going at it in the crab pose. So I continued on my trip and ended up in reverse cowgirl.

If you read my last blog, 77 Positions in 77 Days, then you know that I had never tried reverse cowgirl until recently, but as soon as I did, I was a convert. It feels so amazing and I secretly think that it gives D. a great (and flattering) view of my ass. We stayed like this for a while and D. did the reach around and stimulated my clitoris manually. When I came close to climaxing, I grabbed his hand and moved it over his to make sure I got just the touch I wanted.

It worked; I had a super strong orgasm and I could hear D. moaning behind me so I knew he was enjoying watching me arch my back and throw my head back. Once the waves of pleasure ceased, I turned around and said, “Well, should we get on with this?”

Without warning D. grabbed my torso again and tried to manually move me the last 180 degrees. Bad, bad idea. I got maybe halfway around then fell. Off his penis. And off the bed.

Yes, it’s as ridiculous as it sounds. Luckily there was a wall not far away to break my fall, but my clumsiness killed the moment. When I recovered and climbed back on top, D. had gone from a full-fledged hard-on to a chubby. (He later said that it’s really hard for guys to stay in the moment when something humorous is going on. It’s like their brains short circuit when they have to deal with two conflicting emotions. Men!)

I didn’t want to pressure D. to get hard again so we could complete the remaining 30 or so degrees. I know from experience that the more a dude knows you’re waiting for him to go stiff, the more difficult the task is. So I decided to give him oral instead. I knew it would be the quickest way to arouse him and he wouldn’t feel like I was waiting on him.

The good thing about starting a blowy when the guy is still a bit soft is that you can usually get the entire thing in your mouth, even if he’s well-endowed. D. loved that and it didn’t take more than a minute or two for him to climax.

Afterward, while we lay in bed laughing about what had happened he looked over, grabbed my hands and said, “S., I’ve never had so much fun having sex with someone.” I feel the exact same way.

Have you ever done a 360? If so, please share your tips for making it work! Also, have you ever had a guy go soft while you’re hooking up? How did you “recover”? Just carrying on or taking a break?

Challenge 12

couple undressing each other standing up
 Go down on him with an ice pop in one hand. Take turns sucking on his penis and the ice pop.

Doughnuts, whipped cream, popsicles. This is starting to feel a bit like a food blog. A very, very dirty food blog. Using very, very lowbrow food. But hey, how many food blogs do you visit that give you tips on how to get off and get your guy off? Thought so.

After a delicious dinner (lasagna with ground turkey meat for all of you foodies who are wondering), D. started washing dishes. I stealthily went into the freezer and grabbed a popsicle. Then I stood behind D. and reached around so I was rubbing his crotch through his jeans. I undid his belt and the top button and reached a hand in.

“Mmmm,” he murmured then turned around so he was facing me.

He dried his hands on his jeans and reached for my face.

Then something happened. I don’t know why, but all I could focus on was how D. had left the water running. Two seconds, three seconds, four seconds passed and he still didn’t turn it off. My inner nag took over and I exclaimed, “D.! You are the worst with leaving the water on!”

As soon as it came out of my mouth I regretted it. What is wrong with me?, I thought. D. is washing the dishes (without being asked), he’s trying to kiss me, and I feel the need to harp on the fact that he sometimes leaves the water running?

“Jesus, S. Sorry, I’m a little distracted since you stuck your hand down my pants.”

I apologized, but the moment was killed. Luckily, I had a popsicle to revive said moment.

Also very luckily, D. is not the type to sulk. And as soon as I reached for the popsicle and asked him if he was up for the challenge, he seemed to forget that I had gone all mean mommy on him.

I unwrapped the popsicle (actually it was a fudgesicle), knelt down, and popped it in my mouth. I admit I felt like a bit of a porn star mimicking oral sex on a frozen treat while my boyfriend watched. But I’ve learned something while doing these challenges. You really have to own it. As silly as it seems to wear a whipped cream bikini or pretend to pleasure a popsicle, if you go big, your guy will, well, get big too. The second you start giggling or acting self-conscious or asking him if you look lame or if you should stop, though, he’ll start to wonder if what you’re doing really is lame. (Yes, this advice is as much for me as it is for all of you since I can be the queen of self-consciousness in bed. Just thought I’d share.)

Anyway, I didn’t giggle and tried my best not to feel stupid. And it worked. D. was loving watching me go to town on that popsicle (not part of the challenge, but why not, right?) and he did this sighing thing he always does when I know he’s enjoying something visual.

After I was sure that my mouth was sufficiently cold, I put my lips around D.’s tip. He flinched at first, but then said, “Ohhh the cold feels good” so I took more of him in my mouth. I felt him harden as I swirled my tongue around him and tightened my lips on his shaft.

After D. was at “full mast”, I pulled away and went back to the fudgesicle. Then I gave his balls some attention. Perhaps not the best technique. I could literally feel them retract into his body when my cold mouth touched them. I quickly shifted my focus back to his shaft. Crisis averted!

I handed the pop to D. and wrapped a hand around the base of D.’s penis. I then began moving it up and down in synch with my mouth so that my lips and the circle I had formed with my thumb and pointer finger never lost contact. This is a great way to simulate a deeper beej without having to worry about your gag reflex.

After, oh, about 10 strokes like this, D.’s knees buckled a little (remember, he was still standing up) and he said, “You’re gonna make me come.” And when he did, I really thought he was going to collapse on top of me and we’d end up in the ER, D. with a busted knee and me with a concussion and melted fudgesicle all over my face.

But D. braced himself on the kitchen counter and managed to stay upright. As soon as he had regained muscle control, he lifted me up and pulled me into a bear hug and whispered, “I love you”. I whipped my head around and smiled.

“What? Don’t look so surprised,” he said, laughing. “I can’t imagine being without you.”

“Well, without me you’d be a guy with his pants around his ankles, a dying boner, and a half-eaten fudgesicle in your hand. So yeah, don’t imagine being without me.”

First, I’ll ask the unsexy question: When you get the urge to nag, how do you quell that? Or do you just let it out and hope that your relationship isn’t slowly turning into that of a miz old couple? And secondly, the sexy question: What is your go-to move to make oral sex hotter for your guy? Mine is the mimicking-deep-throat-by-using-a-hand move, but I want to hear yours!

Challenge 13

  Make an “OK” sign around his penis, then stroke downward and follow with your other hand, making the same motion. Repeat until he climaxes. (Use lots of lube!)

Full disclosure: I am not a hand job girl—I can’t even remember the last time I gave one. (Did I give one during the 77 Positions blog? I’m totally spacing!) Despite what you might have heard from guys (“Why would I want a girl to do that to me when I could just do it myself?”), I learned tonight that being, ahem, handy is very, very hot. Especially when combined with some oral action.

And that’s exactly what I did—combined it with oral. Because I had a feeling it would take D., oh 90 minutes to climax from a hand job alone and as a writer, I can just not afford to get carpal tunnel syndrome. (Or am I wrong? Are guys capable of finishing quickly with just an HJ? Has your guy ever come from that alone?)

But let me back up…I got into bed totally naked while D. was showering. Then when he got in and realized my lack of clothing, he let out a “Woohoo!” and immediately took off his boxer shorts and t-shirt. In the past, I’ve often left on some amount of clothing when I’m giving D. oral, but I thought it would be hotter if he could see my entire bare-ass body while I performed.

I had planned poorly and didn’t have any lube, which is why I chose to start out with oral to get the area wet. I went down on D. hands-free for a minute or so then pulled back.

That’s when I started the “OK” hand job. I placed my right hand around the base of his penis and slooowly moved it toward the tip. As soon as I got there, I followed with my left hand. I continued this for a few strokes then came up with a genius idea (if I do say so myself!). With my mouth free and the shaft taken care of, I could really go to down on his balls. Normally during oral, I use my mouth on his penis, and my hands intermittently on his stepchildren, but this seemed like a fun way to switch it up.

The positioning was a little strange—I had to turn my head sideways to make it work—but the result was awesome! D. was loving all that attention. In fact, I would venture to say that D. seemed to be enjoying this combination more than my aforementioned move!

While spending so much time down below with his two friends, I realized that I don’t have a whole lot of technique variation when it comes to giving the balls oral attention. Normally I’m there for just a few seconds at a time, so a few licks suffices. But since my tour of ball duty lasted a few minutes, I was forced to come up with new moves quickly.

In case you’re interested (and you should be!), here they are:

-Lick the “seam” (ie the line between the balls).

-Use the tip of your tongue to press firmly against his taint (the spot right behind his balls).

-Actually suck on them, though be sure to cover your teeth with your lips.

-Lick them, then pull away and alternate blowing cool air and breathing heavily on them. The alternating hot and chilly sensations can be really pleasurable.

D. finished in just a few minutes and he told me later it “felt really amazing” so I’ll definitely be trying this technique again! Just be sure to have tissues nearby because the clean up is not as easy as with a beej.

Do you have any techniques for giving the balls some loving? What types of touches and licks does your guy prefer in that area?

Challenge 14

woman using a blindfold
  Have sex blindfolded.

I’m just gonna say it. This might be my favorite challenge yet. I effing loved it. And D. told me he feels the same way. In fact, it was so good that I’m going to ask every single one of you to try it tonight then report back in the comments section because I’m dying to hear what you think.

D. and I were standing in line at the grocery store when I turned to him and said, “Oh by the way, we’re having sex with blindfolds on tonight.” I guess I didn’t realize how loudly I said it because the woman in front of us immediately perked up. Well, lady, if you’re out there, here are all the juicy details you wanted to overhear…

D. initially took off his tie and tried to tie it around my head, but it kept slipping down so we had to get creative. D. found two of his winter scarves and we essentially wrapped our entire heads in them. We then bounced around and got in a few different positions to make sure they would stay on. They did. (Though I recommend that if you have sleep masks, you just use those.)

We promised not to remove the scarves until the very end. Then D. said, “OK, let’s get in bed.” I mistakenly thought that I should take off all of my clothing first, assuming D. would do the same. He did not. He left everything down to his socks on, which meant I had to remove them sans vision. You’d think that was the trickiest part, but it wasn’t. We learned that it is surprisingly difficult to find someone’s mouth when you have no visual cues. I probably kissed D.’s cheek last night more than I ever have before.

But the fun started when he began to “finger blast” me (his term, not mine). I decided that because he couldn’t see me, I would totally let go, contort my body into weird positions, make wild faces, etc. just for the hell of it. What I didn’t expect was to actually enjoy doing those things. Let me explain…

While he was going to town on me manually, I lifted both legs straight up in the air and curved my back into a C as if I were doing a sit-up. I wouldn’t normally have done this because, uh, I’m sure I looked like a total Cirque de Soleil freak. But I think it made me reach orgasm more quickly. Even D. said that I came super fast. (Ah, I love that that is a compliment when directed at a girl.) I also made a conscious effort to make wacky O-faces to get a sense of what it was like if I, say, opened my mouth really wide, scrunched by eyes up, or smiled hard. That didn’t seem to make much of a difference during my orgasm. Maybe because I don’t think I usually try to hold back when it comes to my O-face.

Then we got to the main event. There was some confusion as to what position we would get in. I had assumed he’d be on top and he thought I would be on top. Then we realized what was going on and both tried to get on top. And that forced us to communicate. Now, I didn’t realize how little D. and I speak during sex, but this challenge made us be really vocal. And that was hot.

Basically, we had to give play by plays of our every move. “I’m climbing on top of you. I’m going to straddle you. I’m going to lean down and lick your nipple (so don’t accidentally sit up because we’ll knock heads).” You get the idea.

After a few minutes in GOT, I climbed off and stood next to the bed. “Uh, where did you go?” D. asked, sounding slightly panicked. “Stand up,” I told him. I could practically hear his confusion in the silence, but he did as he was told. Then I turned so I was facing away from him, placed his hands on my hips, and bent down.

“Ohhhh, I get it,” D. said, the doggy-style light bulb appearing over his head.

After we had been going at it for a few minutes, I had a realization. Normally D. comes pretty quickly when we’re in this position, but last night he wasn’t. And I know why. It’s the visual that puts him over the edge. When I brought this up with him later, he said he hadn’t really thought about it, but that it was absolutely true. Part of what makes doggy-style so hot for guys is that they get to stare at your butt and watch you bounce back and forth against their crotch. But with blindfolds, it was all about the feeling, not the image. And I’m almost too embarrassed to admit this (but hey, it’s anonymous)…D. went soft on me.

I ended up finishing him off with oral and I know it sounds weird that something like that could happen and this would still be one of my favorite challenges, but I’m sort of blocking out that aspect of it. Because there was something so fun about cutting off one of our senses that made the rest of the experience really hot. And it was freaking fun too! I am such a big fan of being fun/funny in bed and this challenge definitely lends itself to that vibe.

That said, I do want to hear your thoughts about what happened…

Have you ever had a guy go totally soft on you—when he’s not drunk and doesn’t seem too stressed? What did you do? Should I be concerned?


Challenge 15

naked couple kissing
Take off all his clothes…using only your mouth. (You can undo his fly with your fingers.

I’m going to reiterate part of this challenge for you ladies, because I like you and I bet you have nice teeth that you don’t want to destroy: You can undo his fly with your hands. Someone—and I’m not going to name names, but it starts with D—didn’t read the complete challenge when he suggested it and someone—whose name starts with S—might be getting a stern talking to at her next dentist appointment about not biting down on a metal zipper and yanking.

But anyway! As I said, D. suggested the challenge. I was totally game because, as you’ve probably learned, I enjoy having fun in bed and yes, I’ll admit it, being a little silly during sex.

He had mentioned it in the morning before work and I imagined that we would do it right before bed, when it came time to remove our clothes and have sex. But when I arrived at his apartment yesterday evening, I found him looking like he was working at a mall clothing store. Which is to say he was wearing a lot of layers. (Ever noticed that? I secretly think they are minimum layer requirements since they’re basically walking mannequins.) He had purposely dressed heavily because he knew that I’d be removing every item with la bouche. Lovely.

He was standing there with a satisfied grin on his face. And I knew this could not wait until after dinner. I threw down my bag, kicked off my shoes, and gnashed my teeth while growling. “I plan to bite,” I said.

“Fair enough,” he responded, clearly enjoying himself.

I started with the top half of his body. The scarf was easy. Yes, he was wearing a scarf. And I won’t take you through every single jaw-aching detail, but here’s the recap: It is hard to take off a sweater/shirt/undershirt without your hands. If you plan to do this, follow my technique: cheat and use your hands. Ha, just kidding. But seriously, I had to a few times. I used my mouth to peel the sleeves over his hands then I took the bottom of the front of the shirt in my mouth and peeled it up his body. I asked him to lie down then I crouched at this head, leaned over and grabbed the shirt between my teeth again and yanked. I’m sure the whole thing looked oh so sexy.

I used my hands a bit to get it over his head, but that was it!

Thank gah D. was not wearing socks (I wouldn’t have gone there) so next up were his jeans. And remember, ladies, he hadn’t mentioned the part about using your hands on his fly. I was down there for a good two minutes without making any progress—and killing my teeth!—when D. took pity on me. He quickly unbuttoned them and lowered his zipper.

“Ahhh! Thank you! Sweet relief!” I moaned.

“Wow, I wish you said that every time I unzipped my pants.

I didn’t want to put my mouth on the bottom of his jeans. (Have you seen the streets in Manhattan? You wouldn’t want your mouth near that either.) So I started at the top. Tricky business, I’ll tell you. I sort of pulled back both sides of the front of his jeans to reveal his boxers. Basically, to get them down, there was a lot of wiggling on D.’s part and a lot of yanking on my part. I recommend your guy wears lose stretchable clothing for this challenge. Sweatpants or mesh shorts or something similar. When his jeans were at his knees, I went back up and pulled down his boxers. Easy.

And then, well, then I used my mouth for something I enjoy much more—treating D. to oral sex.

Have you ever tried something like this? What are some other suggestions for sexy ways to remove his—or your—clothes before sex? Have you ever given a strip tease? Tell me about the experience below!

Challenge 16

 Leave on stiletto boots or pumps while you have sex in missionary position. Gently press the heels against his butt and thigh.

I’m walking around with a silly grin on my face today. I sat in meetings with the grin on my face. I ate lunch at my desk with the grin on my face. I rode the subway with the grin on my face (even when someone tried to get on while I was trying to get off—huge pet peeve). What’s that? You want to know why? Well, as you can probably guess, it has to do with the challenge.

Last night I had some of the best sex I’ve ever had. D. and I had orgasms that were not only simultaneous (right down to the millisecond), but also incredibly strong. I don’t know if the snakeskin stilettos had anything to do with it, but I might never take off these kicks! I’m going to be like a baseball pitcher who refused to wash his socks after he throws a no-hitter. I won’t take off these shoes after I threw a…eh, never mind, this analogy doesn’t really work. But you get my drift.

D. and I had watched a movie at my place and I was practically dozing off (ugh, why am I always so freaking tired at night lately?), but then when we went to the bathroom to brush our teeth, he got all playful and flirty with me. And by “playful and flirty”, I mean he yanked down the boxers I was wearing as pajamas and pinched my butt. Ladies, this move goes all the way back to prehistoric kindergarten and it means a guy wants sex.

After we brushed and gargled, we made out in the bathroom for a few minutes then took things to the bedroom.

I stealthily sneaked a peek at the Cosmo Challenges list and chose this one. I dropped my boxers, pulled off my tank top, and put on my heels. Now, I believe that the phrase “his jaw dropped” is overused to the point where it’s lost most meaning. But D.’s jaw most definitely lowered at least an inch. The good thing about doing these challenges with a guy is that, even though he’s seen the list and knows that we’ll get to all of them eventually, he is still as excited as a kid in a candy shop when the time actually comes.

D. dropped trou and pushed me up against the wall. There’s something so hot about being a little bit constricted—being caught between a wall and a “hard place” if you will. Then he brought me over to the bed and lay me down so my legs and shoes were dangling off the end. He stood at the foot of the bed and leaned over me, but his weight was still on his feet.

As soon as D. entered me I lifted my legs and wrapped them around his torso. (I was hesitant at first to press my stilettos into his back and wanted to ease into that.) As D. started pumping faster and I knew—from reading Cosmo that his body would be more tolerant of pain (endorphins and all that stuff)—I laid my calves on his back so that he could feel the length of the heel of the shoe. Then I upped it by actually digging in a little—but very gently!

He moaned, which let me know that it was OK so I kept going.

Then he shifted so that his torso was a bit more upright (rather than parallel to mine) and reached between my legs with one hand. He all but stopped thrusting and started to stimulate my clitoris and to be totally frank, I wasn’t anywhere close to climaxing. But he kept at it using some of the techniques he picked up from the 15-minute orgasm tutorial and within about two minutes, I was on the edge.

And when D. whispered that he was about to finish, that pushed me over said edge. And it felt like our bodies were totally synchronized. Every muscle spasm, every gasp, every wave of pleasure. Yes, I know I’m sounding a bit romance novel-ish, but it felt like a scene in a romance novel. All D. needed was long, flowing locks.

Anyway, it was so amazing that I can’t stop smiling. And I keep wanting to ask people, “Did you have an amazing simultaneous orgasm with your hot boyfriend last night? Because I did.”

Yes, I’m showing off. But I’m not going to be selfish and keep the technique to myself. I think it was all about D. slowing down his thrusts (and therefore slowing down his own orgasm) while he manually stimulated me. And he used firm circular motions with two fingers. And as he sensed that I was close to peaking, he resumed thrusting, got himself to a point where he was close then pressed even more firmly on my button. Oh yeah, and don’t forget the lucky heels.

Who knows if that exact formula will work again, but I’m sure as hell going to try.

I’d love to hear your tricks for crossing the finish line at the same time. Share them below por favor!


Challenge 17

couple kissing
  When he’s not expecting it, grab him, and kiss him passionately for a full minute. A lot of couples only kiss hello and goodbye or when they’re lying down, so this will surprise him and turn him on.

Please excuse me while I shamelessly brag for a moment. I am a good kisser. Nay, a great kisser. How do I know this? I’ve been told. And I know what you’re thinking—lots of guys just say that without meaning it. But the percentage of guys I’ve kissed who have given me that compliment is probably about 75 percent. And it’s not just, “You’re a good kisser.” It’s, “Wow, that might be the best kiss I’ve ever had.” One time, after making out with a guy, he messaged me on Gchat later to say that I was awesome at kissing. I once kissed a female friend and she told me after that she hadn’t expected me to be so damn good. Let’s just say that if adults played Spin the Bottle, they would all try to get it to aim at me.

The point of all that is to say that I think the reason I’m such a skilled smoocher is because I enjoy it so much. I freaking love to get my kiss on. Ever since I first planted one on [name redacted], I knew it was for me. And kissing D. is particularly amazing. So, as you can imagine, I’ve been looking forward to this challenge.

This challenge is really similar to Challenge 10 except that it feels less sexual to me. And sweeter. And you may be surprised to hear that I actually wanted this one to feel sweet and innocent and romantic, not at all sexual.

So in the middle of dinner I set down my fork and knife, leaned over the table, grabbed the sides of D.’s face and pressed my lips to his.

(Now, I didn’t have a timer set. I figured I would just kiss until I was sure a minute had passed.)

First we kissed with our mouths closed—and I ran my wet lips from side to side over his. Then I pushed out my bottom lip slightly and wedged it between his lips so he was forced to suck on it. After a few seconds of that I pulled back so our lips were barely touching then parted my mouth slightly and ran my tongue over my own lips so he could also feel it.

D. opened his mouth wide and ran his tongue over mine. It was some intensely hot Frenching! But then that big ol’ tease pulled away and started to gently nip at my lips. (Sidenote: Yes, D. is an amazing kisser. I have definitely met my match. If we ever reproduce, our offspring will be Olympic kissers.)

He then pulled a very impressive maneuver. While still kissing me, he walked around the side of the table so he was next to me. He wrapped his arms around me and starting open-mouth kissing me again. And I swear, my knees went a little weak. And that’s when I realized how great this challenge really is. It allows you to kiss long enough to get that weak-kneed feeling without going into sexy time territory. And D. and I are rarely in that sweet spot.

We kept on smooching for at least another 30 seconds and when we pulled away both D. and I had big goofy grins on our face. Man, I love that guy.

How often do you kiss your guy without having it lead to sex? Do you always kiss hello and goodbye? When is the last time you made out for a long time with him?

Challenge 18

couple kissing
  Put lube between your breasts, squeeze them together, and have him thrust into your cleavage.

I don’t know about you ladies, but I most definitely did not learn about this form of sex in high school health class. Which is why it’s a very good thing that Cosmo exists—to supplement my very lacking sex education.

Don’t get me wrong. I’ve t-effed before. But it’s not a big part of my repertoire. I always feel slightly awkward doing it, like, uh, What should I do while you’re up there thrusting away? That said, D. is a a fan and though he wouldn’t admit it, I think he wishes we did this more. You see, D. is fascinated with my breasts. (OK, it’s probably more accurate to say he’s fascinated with breasts in general, but he has better access to these tatas.) If it were up to him, I’d be topless at all times at our apartments—cooking, watching TV, doing Zumba exercise videos.

What I’m trying to say is that I knew he was going to be into this challenge and I wanted it to feel really special. I showered first and exfoliated my chest to make sure it was nice and smooth. (Downside: it was all red, but I like to think that it was a bull’s eye for D.) Then I coated my breasts, chest, and shoulders with lotion. Fragrance-free, alcohol-free lotion. I recommend you do the same unless you want him to get peen burn.

I grabbed a bottle of that same lotion and brought it into bed.

“Are you DTTF?” I asked.

D. looked slightly confused. “Down to…[lightbulb goes on] Oh! Yes!” he exclaimed.

I lay on my back and handed him the lotion, suggesting he first lube me up.

It turned into a super hot breast massage, which was just lovely. But it got cut short as soon as D. got hard. Which was, oh, two minutes in.

He straddled my chest, which then leaned forward so his hands were resting on the wall. I squeezed my twins together and around D.’s shaft and he thrust forward.

I found that the most comfortable position was for me to sort of push my right breast in by pushing my right upper arm against it and using my left hand to squeeze my cleavage together. (Is this making any sense? Here’s another way to think of it: If my cleavage was a half pipe—or rather, three-quarter pipe—for D.’s junk to, ahem, travel in, my left hand was the top one quarter of the pipe. OK, this is probably getting more and more confusing for you. All you have to know is squeeze ’em together and if you need help squeezing to make it tighter, use a hand.)

We had to stop three times to add more lotion, but D. told me afterward that he liked the physical action intermittently sprinkled with visual stimulation (ie, him rubbing lotion on my breasts).

He finished after about 10 minutes, which feels like a hella long time when your breasts are getting banged. (And yes, he gave me a pearl necklace.) Next time I think I’ll start with oral and use more lube to make the process go faster.

Have you ever t-effed? Any tricks for making it more enjoyable?

Challenge 19

couple undressing each other standing up
  Have him push you up against the wall in a narrow area, like a hallway, then have standing-up sex.

I’ve written in the past about how I have trouble fully enjoying any sort of sex position in which the guy has to hold me up. And some of you have shared that you’re in the same boat as me. It’s not that I think they can’t hold me or I’m self-conscious about my weight or anything. It’s just that I can’t fully relax because I’m thinking about his muscles getting tired, if I might fall, etc. Well, ladies, I’ve found a way to enjoy standing-up-against-a-wall booty. It’s a little solution I like to call Doggy Up Against a Wall.

D. and I discussed doing this challenge in the morning and all day I was thinking about the best place for us to do it. I don’t have any narrow hallways and I’m luckier than many New Yorkers in that my bedroom is wider than my wingspan. So I chose the doorway to my bedroom.

And it ended up being ideal! I hereby declare that the doorway is the new bed! OK, maybe not, but it’s definitely an untapped hot spot.

D. and I were already in bed when we started making out. (I’m all about the looong kissing sessions now.) As soon as we had removed each other’s clothes, I led him to the door and opened it very quietly. Oh yeah, did I mention that my roommates were home? Yep. It was late and their doors were shut, and we kept the lights off. I figured that if anyone came out, we could stealthily dismount and return to bed unnoticed. Looking back, this was probably totally unrealistic, but what can I say? I guess I was in the mood for an extra challenge and thrill of potentially getting caught.

But back to the original challenge. We stood in the doorway and suddenly, remember that D. was supposed to push me up against it, I said, “D., push me up against the door.” He obliged, though it definitely doesn’t feel as animalistic when you have to prompt the guy to tap into his animal urges. Ah well. He did and we grinded against each other. Well, he grinded against me and I stood, pressed up against the doorway.

When it came time to move past foreplay and get to the main event, I have to admit I was slightly nervous. Having him hold me up against a wall is nerve-racking enough, but up against the narrow edge of the doorway while my roommates slept nearby was a whole other story. So I improvised. And thus was born Doggy Up Against a Wall.

I turned around so I was nearly flush against the doorway with one hand on either side of the wall and stuck my butt out. D. pulled at my hips so my body was basically forming a sideways V. He reached around and slipped a hand between my legs. I was already wet from the grinding, but he kept on keeping on with the foreplay. I love that he did that! Sometimes I feel like guys wait for the absolute first hint that our bodies are ready for penetration and go for it. There’s something really nice about knowing that he didn’t just want me to be ready, but to be dying for it.

And man, was I dying for it. D. brought me close to an orgasm–alternating rubbing my clitoris in slow, circular motions and inserting two fingers inside me while tugging at my nipples with his other hand. And they say men can’t multi-task!

When my breathing got heavy and I was close to finishing, D. must have sensed it. He pulled his hands away and then pushed himself into me. But instead of sticking my butt out further so we were in a more typical doggy style position, I tried to flatten myself against the door.

Had there been less foreplay, I think it might have been uncomfortable, but it felt amazing! It was such a tight fit and each time D. pulled out and thrust in, I felt his tip all along the inside of me.

Then D. put his hands over mine so we were both supporting ourselves on either side of the wall and pushed his entire body against mine, thrusting very gently and shallowly. He hit my G-spot and I climaxed quickly. He followed and here’s where my only complaint about this position comes in: when he finished, he rammed against me, pushing my groin and torso against the wood panel of the doorway. Uncomf. Next time, I’ll be more prepared.

Have you ever done doggy standing almost straight up against a wall? Any tips for making it extra hot? And out of curiosity, on average how long does foreplay last for you and your guy?

Challenge 20

couple kissing
 Have sex without making a sound.

Note to the Cosmo editors of this blog: Yes, I know this challenge wasn’t on the list you gave me. But pleeeaaase let me include it. Read on and you’ll see that it’s an awesome challenge!

Editor’s note: Sure, we’re always up for hearing new sexy dares. (Just as long as you’re not using this to get out of #25 on the list!)

Warning to prude readers: you will probably not like this post. Actually, if you’re a prude, you probably won’t like this blog at all. And you’re probably not reading it. So we’re all good! For the rest of you, you might judge me a tad, but I think you’re still going to like it.

I hooked up with D. while other people were in the room. I know, gasp. But in my defense, it was a big room. And we were very horny. D.’s two friends were staying with him—on an air mattress on the floor—and we were going to stay at my apartment, but we all went to a bar and D.’s place was just so close. And I didn’t feel like trekking to my apartment. So that was that.

D.’s friends were more than just a little buzzed and they quickly passed out on the air mattress and began snoring. And I took that as a cue to start having the sessay time.

I surprised D. by pulling off his tee and shorts then stripping down. Then, after making sure that Buzzed and Buzzed-er were still snoring away, I got on top of him totally nekkid. D. was pretty much paralyzed with fear of being caught so I took his right hand and pressed it between my legs. I kept my hand over his as he began to move his fingers inside of me. It was really difficult not to let out a single moan or even a heavy breath. But I let D. keep going.

I leaned down so I was on my hands and knees, my face hovering over his face, allowing him better access to my naughty bits. At one point, I started to let out a noise, but D. clamped his mouth over mine and kissed me hard. It was seriously hot.

Then he flipped me over and got on top, spreading my legs with his knee and pushing himself inside me. He started thrusting, but it was causing a creak-squeak noise over and over. We heard Mr. Buzzed shift on the air mattress (luckily it was loud as all hell) and we immediately froze. Then his snoring resumed, letting us know that it was safe to resume thrusting.

To avoid making noise I lifted my hips so when D. pressed against me, I didn’t get pushed into the bed.

“It’s like we’re having astronaut sex,” I whispered. And it really was. Very weightless-feeling and a bit strange.

After a few minutes, I got ballsy and decided I wanted to be on top so we repositioned. I’m not gonna lie—I was watching Buzzed and Buzzed-er almost the whole time, making sure they didn’t wake up. Definitely not the best thing to be paying attention to when you’re having sex, but hey, it is what it is.

I leaned back on my hands so that my back was arched and D. was hitting my G-spot. My breathing started getting heavy and I let out a whisper of a moan. D. reached up and hooked his thumb in my mouth to quiet me. I closed my lips around it and sucked. I know, very porn star-esque. Except of course for the lack of pleasure noises.

I came quickly—and fairly silently—and D. followed soon after. He looked he was concentrating a hell of a lot to keep from letting out a massive groan. It was actually really sexy to watch him try to contain himself.

Afterward, we lay under the covers catching our breath and giggling (yes, D. giggled) about our naughty little “public” hookup. And D.’s two friends didn’t act weird this morning, which makes me think they didn’t realize what went on just a few feet from them.

And while I probably would have climaxed even if we were making noise, I have to say that the silence made it extra hot. In the same way that cutting off one sense (sight) makes you focus more on the physical sensations, taking the sounds out of sex, made me show my enjoyment in other ways, like really moving my hips or breathing heavily on D. or whatever.

Have you ever tried “silent sex”? And at the other end of the spectrum, what kinds of noise do you usually make? Do you have a go-to moan or word/phrase you use a lot?

Challenge 21

couple making out in public
  Go to a bar or restaurant where there’s a single-stall bathroom. Stop inside together and make out.

As you may or may not remember from my last blog, 77 Positions in 77 Days, D. and I were once escorted out of a bar for trying to get busy in a bathroom stall. (And I once got kicked out of a bar at college for bringing a guy in with me.) But bouncers and rules be damned! I would not let a history of making-out-in-public-bathrooms problems stop us from completing the challenge at hand. (That said, we took extreme measures not to get noticed by anyone who worked at the bar. Because, honestly, if we were kicked out of a bar for a third time, my friends might start to judge and call me an exhibitionist behind my back.)

D. and I were at a friend’s birthday party that had devolved into nothing more than a Thirsty Thursday. Read: everyone was pretty boozed up. Read: they wouldn’t notice if D. and I sneaked away for a few minutes. I wasn’t drinking (headache) and D. had drank only a couple beers so we were very sober compared to the rest of the group. Which I think worked in our favor. (If we were to flash back to the past two times I attempted this—and was subsequently booted—you would see that I was far from sober and that’s ultimately what got me caught. Basically, what I’m saying is don’t get silly-drunk and try this challenge. It’s one that’s much better executed with your wits about you.

D. and I stood by the beer pong table and when everyone around us seemed completely riveted by the game, I whispered to D., “Three minutes. Bathroom. Prepare to suck face.”

And then I proceeded to shimmy on over to the bar. (That’s the second secret to completing this challenge without getting caught: don’t both head over to the bathroom together. Amateur mistake. Dead giveaway.) Once I was sure no one was looking (and yes, I did feel a bit like the female James Bond, in case you’re wondering) I walked over to the bathroom, which was around a corner. A minute later D. joined me.

We locked the door and operation makeout commenced. We knew from the beginning we weren’t going to have sex in there, but we hadn’t discussed in detail exactly what we would do. We just said we’d just play it by ear.

Well, apparently “play it by ear” means “finger blasting” in D.’s dictionary…

We started by just kissing. Then D. stuck his hand up my dress and started caressing my thighs. And ladies, I’m not going to, ahem, beat around the bush. I got wet really quickly. I think it was a combination of the the fact that I knew we could get caught and the urgency of the situation. D. didn’t even remove my underwear. He just pushed them aside and inserted two fingers in me. He alternated stroking my G-spot and rubbing my clitoris. And within about three minutes (or the length of one song played by the DJ on just the other side of the wall), I climaxed. And here’s where we come to lesson number three: do this challenge in a loud bar. When I climaxed, I got suuuper loud. OK, some of it might have been slightly exaggerated just for the hell of it. Hey, when else can you yell, “Oh, D., yes, yes, yesssss!” in a public place?

After my little show, I slumped against D. and told him that this was one of the best birthday parties I’d ever been to.

After basking in the moment for, oh, 15 seconds (everything’s accelerated when there’s potentially someone standing outside waiting to use the bathroom), we gathered ourselves and I reached for the door handle.

“Wait!” D. exclaimed. And I swear, for a second I thought he was going to ask that I reciprocate. Which would have been totally cool if it weren’t for the aforementioned potential someone outside the door. “I need to wash my hands.”

Ahh, D. Ever the hygienic person.

After he washed, I slowly opened the door to check for people. Nobody was waiting and not a single bouncer was in sight. Phew.

I walked out first and made a beeline for the bar. D. must have followed because when I got back to the beer pong table, he was standing there. And the game wasn’t even finished. That’s how quick we were.

Have you ever hooked up in the bathroom of a bar or restaurant? Did you get caught?

Challenge 22

 Make up a sex position based on the name The Dirty Downward Dog, and try it out tonight.

Yesterday I was flipping through the channels and came across Going the Distance. And I would have kept flipping (don’t hate me for saying this, but I’m not a huge Drew B. fan), but it was the scene where she and Justin Long are having slow, sweet, romantic, perfectly lit, intimate sex, probably with some amazing song in the background, and I was entranced. You’d think I was some 11-year old who was watching a sex scene for the first time. (Hmm, guessing kids these days don’t usually make it to 11 without seeing a sex scene. Ugh, I feel old.) But I couldn’t stop watching. Justin does not do it for me (except in those Mac/PC commercials and I think that’s more about the fact that I am super into Apple products), but in that moment, I never wanted to be under Justin Long so much in my life.

And then it hit me. They were—excuse me while I gag out this phrase—making love. I despise that phrase. Like, despise despise. But that’s exactly what they were doing and there’s no other way to describe it. And a moment later, something else hit me. It has been a long ass time since D. and I have—must suppress gag reflex—made the love.

Don’t get me wrong. The sex, as you all know, has been good. Oftentimes damn good. But love has not been made as of late. And I miss it. (OK, as I typed that, I had to suppress another kind of physical reaction, a little lump in my throat.

Now, don’t go reading in to this and start thinking that something’s off in our relationship, yadda yadda yadda. (Though, yes, that’s probably what I would consider if I were you.) But I do think we’ve temporarily forgotten that sex doesn’t have to be all aggressive and hot-n-raunchy all the time.

After the scene ended, I rehinged my jaw, picked up my phone, and called D.

“What are you doing right now?” I asked when he picked up.

“Watching TV.”

Going the Distance?!”

“Uh, I don’t know what that is, but no.”

“Well, I am and it’s making me want to see you and hook up with you.”

“I like this movie! Come on over!”

I paused. “OK, but I don’t want to have sex. I want to…have…intimate non-sex sex.”

“I have no idea what you’re talking about, but come over for some non-sex sex.”

I headed over and told D. about my realization and how I was feeling. He totally got me and he said that what he loves about hooking up with me is that it’s always different and new-feeling. And that if I wanted to try something a little different (ie, calmer, slower), he was all for it.

I told him we should create a sex position, as per this challenge, but we should come up with one that wasn’t doggy style. Cue look of slight disappointment in D.’s eyes. Sorry, dude, but doggy style is not what comes to mind when I think of lovemaking. I was able to say it without gagging that time!

Here’s what we came up with:

D. sat on the couch with his feet planted on the ground. I straddled him and wrapped my legs around his torso. Once he was inside me, he cupped the back of my head with his right hand, put his left one on my lower back and leaned forward. Far forward. So my head was almost touching the floor. Then he proceeded to thrust slash rock back and forth.

I put my feet up on the back of the couch and grabbed onto D.’s shoulders. He was really deep inside of me and each thrust felt really intense.

And here’s the best part: we maintained eye contact almost the entire time. And we didn’t say anything. I think I was trying to emulate the Going the Distance scene I had watched earlier (Go ahead, judge me. I’m judging myself!) and D. was just following my silent lead.

The position allowed for awesome clitoral stimulation, but I think D. was actually too deep to hit my G-spot (is that possible?). I needed D. to be moving in a slightly more circular way if I was going to climax, so I whispered for him to stay still and I began to move my hips in small circles (really, more like ovals) until I got close. Then I lowered my feet and wrapped them around his torso again so I could pull him closer to me. I arched my back, completed a few more circles and bam. Orgasm.

D. watched without moving or saying anything as I climaxed. And after I returned to this planet, he started gently thrusting again. A minute later, he finished, pulling me up into a sitting position and hugging me hard.

If it were a movie, we would have had perfect, slow-motion, simultaneous orgasms without any mess or clean-up. But I’m not Drew and he’s not Justin and this wasn’t a movie so I can’t complain.

Then D. went off-script and whispered in my ear, “I love you so much, [insert my full name here].” JLong, you got nothing on my leading man.

OK, I’m dying to know if anyone else has experience what I did—the sense that you and your guy only have sex, but don’t make love. Or is it the opposite, that you feel like you’re always having nice, lovely, intimate sex, but rarely effing. Also, if you had to choose between banging porn-style and doing it Going the Distance-style for the rest of your relationship, which would it be?

Challenge 23

 Have him stand facing you while you’re laying face-up on the bed and give him upside down oral.

So, uh, this is pretty much the opposite of the last challenge. (Though D. did try to convince me otherwise. He said, “Think of it as making love to my penis.” Real nice, D.)

Now, I don’t remember how I first learned about upside-down oral. It might have been Cosmo, it might have been Samantha on Sex and the City, and it might have been a friend at a sleepover. All I know is that the word on the street was that if you went down on a guy while you were face-up, it was easier to deep throat.

Full disclosure: I am not a deep throater. I gag. A lot. I gag at the dentist when they put the fluoride treatments in. I often gag when I brush my teeth. And I occasionally gag when I go downtown on D. (Downtown on D. Hmm, sounds like a dirty movie.) My name is S. and I’m a gagger.

It hasn’t ever been a problem even when the package in question is rather large. I have a little trick which I’m sure I’ve shared here before (or more likely, you already knew because you all are such sex goddesses!): “extend” your mouth by wrapping your thumb and a few fingers around his shaft and keeping your hand flush against your lips. It gives the impression of taking him in deeper than you are.

So needless to say, I am the perfect guinea pig for this move. And I’m happy to report that Cosmo/Samantha/my friend at the sleepover was not wrong. I was able to take more of D. in my mouth without my gag reflex kicking in. Well, let me rephrase that. I was able to take more of D. in my mouth without my gag reflex kicking in as much. Alas, it did kick in (but only because D. got overzealous and thrust too much) and it wasn’t pretty. (More on that later.)

I got on my back (fully clothed, which now I realize was a tad weird) and hung my head off the side of the bed. Then D. dropped trou and positioned himself right near my face.

Here’s where I take a moment to discuss the male genitalia as seen from underneath. WTF?!?! And that’s all I have to say about that.

I had to lean way back and then D. sort of “placed” himself in my mouth. The angling was very awkward and weird at first, but as soon as D. got hard and we got into a rhythm, it was smooth sailing. I even reached around and grabbed his butt cheeks.

I definitely noticed that I was able to take him in deeper than usual. (I remember hearing that your throat is stretched out or something, but don’t quote me on that since it could have been some unreliable sleepover guest who also told me that you can get pregnant from kissing. FYI, not true.)

But then it happened. D. thrust just a tad too deeply, I gagged, and dear readers, I admit this only because this blog is anonymous, I gagged-slash-snorted-slash-coughed and snot came out of my nose. Yes, yes it did. I must have looked like a deer in headlights. A deer with a sinus problem in headlights, to be exact. But D. was so close to finishing that he didn’t seem to notice. Or actually, now that I think about it…I was convinced he could see me (paranoid), but I bet he couldn’t.

He finished up quickly and I third-grader-ly wiped my nose on my sleeve before he could spot the evidence of my gagging fiasco. Or at least some of the evidence. He later apologized for “bein’ so huge” and making me gag. I don’t think he was that sorry.

Have you ever tried this technique? Any tips for not gagging during oral, ladies? And make me feel better—share your most mortifying bodily function mishap during a hookup.

Challenge 24

from the back

Cosmo Challenge: Put your hair in a ponytail and have him gently yank it while doing you from behind.

Call me crazy, but in some ways this feels like the raunchiest of all the challenges we’ve done. (This coming from the girl who answered the door in a whipped cream bikini and ate a doughnut off a shaft.) But I think it’s that this one seems porn-ish. And don’t get me wrong, I love porn as much as the next horny girl, but that doesn’t mean I want to star in my own personal porno, thankyouverymuch.

So I decided to have a little sit-down with D. before engaging in this challenge.

“I don’t want this to get…weird,” I said, hoping he would just read my mind.

“Uh, care to elaborate?” he responded, clearly not having read my mind.

“Like…don’t think of me as a porn star.”

D. stifled a laugh and I got irrationally offended. “I could be if I wanted to, you know.”

“Got it, S. You’re not a porn star, I won’t treat you like one, but I’ll remember that you could be one. Anything else I should keep in mind?”

“That’s all. Except…well, do we need a safety word?”

That’s when he full on burst out laughing. “S., we’re not breaking out ball gags or doing intense roleplay. I think we’ll be fine. All I’m going to do is pull your hair.” Then he reached over and tugged at my hair. “See?”

Satisfied that this wouldn’t get into icky territory (I know, I know, I’m crazy), I agreed to carry on with the challenge.

D. started by going down on me. And holy moly, I wanted to forget the whole challenge and just stick with that. But—argh—D. stopped before I could climax and moved right into doggy style. (Aside: does it bother you when a guy gets really close to making you orgasm then stops? Uh, it’s not like we can’t keep going, dudes. The show can go on.)

I’ve learned over the years that D. (and other guys) tend to really love when a girl is on her elbows and knees rather than hands and knees. So instead of your back being like a table top, it’s at a 45-or-so degree angle and your butt is pointed up at him. And that’s exactly what I did. It got a, “Oh god, S.” out of D.

D. knelt behind me, but instead of getting right to it, he reached his right hand under and between my legs (!) and inserted it inside me. Then with the other hand he reached around my torso and started gently rubbing my clitoris (!!). And then with his other hand (!!!)…no, just kidding. But it was pretty freaking amazing. Then again he stopped before I climaxed. Duuude, come on.

He pulled his hands away and pushed his penis inside me. He reached around and rubbed my clitoris as he did. And ladies, I kid you not: within five, OK maybe seven, seconds, I finished. I think I was so warmed up that just the slightest touch sent me over the edge. It was awesome.

D. had a slightly delayed reaction (he must have been shocked that I needed just a few seconds of P in the V to have an O), but as soon as he realized what was going on, he reached up with his free hand and pulled the pony.

I had almost forgotten that was part of the deal and for a moment I thought, What the eff?!. D. tugged very gently and there was no pain. Or perhaps he tugged hard, but I didn’t feel the pain since your body has a higher tolerance for discomfort when you’re turned on. Interesante, right?

D. took a few minutes more to meet me at the finish line, but I was so blissed out that I hardly realized what was going on. Afterward, while we were laying in bed, sweaty and smiling, D. said, “That was hotter than porn.”

Do you and your guy ever get a little rough with each other during sex? What’s the farthest you’ve gone? Hair-pulling? Spanking?

Challenge 25

  Have sex outside (in your yard at night) and leave your clothes 100 feet from where you’re getting it on. It’ll make you feel more vulnerable and naughty.

I sit here typing with sand between my butt cheeks. And no, that is not a non sequitur. It has to do with the above challenge. As you might have guessed by now, D. and I had sex on the beach. (And yes, I’m giving myself major props for using “butt cheeks” and “non sequitur” in consecutive sentences for the first time in the history of writing.)

I knew from the beginning of the blog that this was going to be a challenge to complete for the following reasons:

1. My “yard” is an alley. An alley where I’ve seen drunk kids smoking, feral cats, Ratatouille (this is my name for rats because it makes me think they’re not gross, diseased creatures, but rather adorable, friendly characters from children’s movies), and trash. A lot of trash. This is not my idea of a hot hookup locale.

2. No less than 315 (rough estimate) people would be able to watch D. and me doing it. And there would probably be a YouTube clip of us. Then our anonymity would be lost. Then I’d have to stop blogging for Cosmo. And I don’t want that. And I hope you guys don’t either!

3. We were at D.’s parents’ beach house (which they weren’t using at the time) and well, how could we not complete this challenge on the beach?

So let me set the scene for you…

Nighttime. About 9:30 p.m. Empty-ish private beach. We were in clothes, not bathing suits. Totally sober (this is important to mention because I don’t want you to think my judgment was impaired when you read certain details below).

We started by sitting on the shore just hanging out. He was sitting with his legs outstretched and I had my head on his lap facing up. D. wasn’t making any moves—even though we had previously agreed to do the dirty there—so I had to take matters into my own hands mouth.

I turned my head slightly toward his upper body and started kissing his stomach. Then I shimmied his shorts and boxer-briefs down and had a big glass of Oral Sex on the Beach.

Then an interesting thing happened. My body was perpendicular to D.’s at this point, sort of propped up on my side and he was now leaning back on his elbows. Can you picture it? So, then he shifted a bit so that his torso was more parallel to my body and his head was near my crotch. He started kissing my belly and thighs then reached up my skirt and rubbed me through my underwear. (I had forgotten how hot it is to be touched through the fabric of undies—the sensation is totally different. And totally hot.

I was still going to town on his nether region when he pushed aside my thong and inserted one finger inside of me. I let out a moan, then immediately stifled it, worried that the people down the beach would hear my ecstatic soundtrack and know what was up…and…I don’t know? Tell D.’s parents? Call the cops?

Oh? Did I forget to mention there were people on the beach? Yes, just a few and thy weren’t nearby. Plus, it was nearly pitch black so they definitely couldn’t see us. (There’s another reason doing it in my city “yard” would be a bad idea: there’s no such thing as pitch black in Manhattan, which would just make our sure-to-be-shot YouTube clip that much more embarrassing.)

So there we were in the 69 position (only it wasn’t mutual oral, it was oral and manual) on the beach. Lovely. But I wanted to actually have sex on the beach. Full-on, real deal, textbook definition sex.

(For those of you thinking of doing this: throw down a towel first. Getting sand in personal crevices is less than fun. And according to something I read in Cosmo, it can be risky too.)

“I want you inside me,” I whimpered. (Yes, I just used the word whimpered. That’s how hot D. got me.)

“I want to be inside you,” D. responded. (Sort of the equivalent of saying, “You too” when one partner says, “You make me so happy”—which is to say, not super creative or thoughtful—but this was sex, not a love letter and I believed him.

I sat up, yanked down my underwear, tossed it aside (never to be seen again), and straddled D. I lowered myself onto him slowly, taking him in one inch at a time and he groaned with pleasure slash impatience (impleatience, if you will). Then I leaned forward and pinned his hands over his head in the sand.

“Don’t move,” I commanded and he stopped his mini-thrusts. (Do your boyfriends/husbands/hookup buddies thrust even when they’re on the bottom? I’ve never been with a guy who does it as much as D.) Then I moved my hips in circles, feeling the pressure of his penis on the front, back, and sides of my lady canal.

Because I was leaning forward slightly, I was getting awesome clitoral stimulation and I told D. that I was close to finishing. Actually, I moaned (loudly), “You feel so damn good, I’m going to come any second.”

And I did. And he was close behind.

A moment later, I got off of him and stood up to search for my underwear. And that’s when I realized it: those people who were far down the beach? Not so far down the beach? Actually, rather close. I freaked and immediately lay down next to D. (I guess so he would block me?). Then we decided to make our stealthy exit. No time to continue looking for my underwear. We grabbed our flip-flops and bolted. And as we ran—me, commando and D., with his shorts unzipped and unbuttoned—we heard laughter. I’ll never know if they were laughing at us. Or if they had no idea what we were doing—or that we were there at all. But I’m pretty sure there’s a group of people telling the story of the Sex on the Beach couple to their friends right now. If you’re out there, hope you liked the show!

Ever had sex on the beach? Ever been caught having sex? Ever had both experiences at the same like moi?

Challenge 26

  Pose naked, and sketch each other.

Yes, that dashing young woman you see above is me. Though because D. is quite the artiste (we both were into art in college), I had to cut off my head from the image. But he did an awesome job and I’m sort of tempted to frame it and put it up in my room. Except, of course, that my parents are often in my apartment. And I have roommates. And friends who come over. And a landlord who is occasionally there too. But there is a part of me that’s glad I at least have the option of doing it. It’s like that Sex and the City (last SATC reference in this blog, I promise…maybe) episode when Samantha gets nudie photos taken so that when she’s old and gray and saggy, she can remember when she looked hot. Sidenote: I don’t think Kim Cattrall will ever be old and gray and saggy. I, on the other hand, will be someday.

But back to the challenge. So! D. and I waited till the roomies were away then locked ourselves in my room with lots of paper, pencils, a glass of wine each (highly recommended if you’re going to do this), and a kick-ass sexy playlist. We used Cosmo’s suggestions then supplemented with the following: “Everlasting Light” by The Black Keys. If I were in the habit of quoting Rachel Zoe, I would say, “I diiiieee” right now. It’s so good. Go Grooveshark it right this second. And if you love it, go download it. Your genitals will thank me. It’s the perfect hookup song. Also, “The Horses” by Ricki Lee Jones from the Jerry Maguire soundtrack. Cheesy as a big block of cheddar, but good for intimate moments like this. And lastly, Edie Brickell’s “Nothing”. Old school, classic, relaxing, the perfect get-drawn-naked-by-your-boyfriend song.

D. wanted me to pose sitting on the bed cross-legged. I could think of nothing less flattering and immediately nixed that idea. (Note to those of you thinking of trying this: definitely practice your poses beforehand. I had two in mind: one in which I was laying face-down with my head in my chin and the other in the pose you see above. D. wanted to be able to draw a little nip—apparently his specialty—so we went with the latter.)

I giggled the whole time, but D. maintained his composure. What a professional.

And when he showed me the finished drawing, I have to admit I got a little teary-eyed. Judge away, but I thought it was just really sweet. Sure, he had to do it for the challenge, but the fact that he took it so seriously and did such an awesome job made me feel really good.

And damn, did he do an awesome job.

So then it was my turn.

Unlike me, D. had not put any time into what pose he wanted. What he had decided? That he had to be at full mast. Oh sorry, I forgot this is Cosmo—no euphemisms necessary. He wanted his penis to be hard.

So while I giggled and gawked he fluffed himself. Which only made me giggle and gawk more. But again, he maintained his composure with all of the professionalism of a nude art model. Has he done this before?

D. was also happy with the finished product. Just look at the size of that blurry area [Editor’s Note: black box] between his legs! But I swear I didn’t exaggerate. From that angle, it really was that big!

So, what do you think of our creations? Would you ever try this? Have you already?


Challenge 27

  Pick up a vibrating ring that slips around his shaft, and use it tonight.

“I think this could be like a gateway drug,” said D. as we walked into the drugstore a few days ago.

I looked at him puzzled.

“First it’s a little vibrating ring that you pick up in Duane Reade. Then it’s bunny rabbits.”

Awww, D. was having vibrator envy. I assured him that he didn’t have to worry about competition because nothing beats a good old-fashioned, non-battery operated penis. (What I didn’t tell him: I had a sneaking suspicion that a battery-operated device combined with a good old-fashioned penis might win the competition.)

We purchased our new toy. It cost $13, $15 if you count the gum I purchased along with it because I suddenly turned into my 14-year old self (the girl who was embarrassed to buy tampons) and didn’t want to be seen purchasing just a vibrating ring. The gum clearly made it much better. Right.

“I don’t need a bag, ” I told the cashier. Always thinking about the environment, even when I’m thinking about D.’s soon-to-be-buzzing shaft.

“Just a garbage-sized bag to wear on my—”

D. started to joke.

Oooookay!“, I interrupted and pulled him out of the store.

I’ll skip over the subway ride home in which we made just about every “ring” pun you could think of. The highlight was probably D. doing the “Single Ladies” dance in his seat and singing, “If you like it then you shoulda put a c*ck ring on it”. You get the idea.

Later, when we were naked in bed, things stopped being so funny. Dun dun dun. I know, that sounded so dramatic. But it did catch me off guard…

D. couldn’t keep it up. He had a “chubby” throughout all of the foreplay, but never got “rock hard”. These are all his phrases by the way. And then once he put the ring around his…posey (sorry, it just sounded so right), he went soft.

He tried to enter me a few times, but…uh, yeah so not happening. I could tell it was getting him stressed out. He was flustered and just kept trying and trying even though it clearly was a no-go. I pushed him down on the bed and went down on him for a minute, but it was as if his junk had taken an Ambien.

“It’s this weird contraption!” he said. “It just looks so weird!”

And indeed it did. Very robotic. Not enough to throw me off my game, but then again, it wasn’t my penis.

I continued to go down on him, but got nothing. So we decided to take a break. D. pleasured me manually—something that usually gets him very hard very quickly. Nada. Even though I turned up the volume and maybe exaggerated the sounds a teensy bit.

I could tell he was feeling really stressed about it so we just stopped completely.

And here’s the thing, ladies. This isn’t the first time it’s happened. D. and I were hooking up a few days earlier and D. was one big Mister Softee. He says he got stressed because of where we were (a bathroom at a house party, and there was a guy banging on the door telling us to hurry up). Fair enough. I can see why that would make it hard to get…well, hard. But twice in one week was slightly worrisome. Or is it? Am I overreacting? They say it’s not a trend until it happens three times. So until then I’ll try not to think about it.

Anyway, the next day I was determined to make it work. (I don’t think Tim Gunn’s words have ever been used in this type of situation, but it fits!) I made sure there were no distractions in the room, lit a candle, dimmed the lights, and then I teased D. big time. I didn’t want to go right for the bull’s eye and make him feel bad if he couldn’t go from six to noon. So I started with his nipples. I licked them, sucked on them, then gently bit them. I sneaked a peek down below and saw that we had lift-off so I slowly worked my way down, first kissing his stomach, then his cut lines, then his thighs, then his balls, and finally taking him in my mouth. He got to 100 percent in just a few seconds, but I didn’t stop because I knew that going to get the apparatus (sounds so sexy, right?) and putting it on had the potential to kill his boner. And I wanted him to be almost on the edge of climax when we had to pause.

I waited until I heard his breathing get ragged and he was saying my name every few seconds. Ha, it’s like monitoring contractions. “They’re 15 seconds apart! It’s go time with the vibrating ring!”

Then I reached for the ring, handed it to D., and held my breath.

He took it from me. Stayed hard. Stretched the ring part (yes, it’s stretchy). Stayed hard. Placed it at the base of his shaft. Stayed hard.

D. pushed my legs apart, kneeled in front of me, and pushed in. Then he literally growled. I’m not kidding. He grabbed my wrists, pinned them above my head, and began to thrust.

I think that’s what the call a comeback, folks.

After a few minutes of missionary, he flipped me over so I was on top and that’s when he turned on the buzzy toy. (There’s a little switch on the side.) I was shocked at how strong the vibrations were. Shocked. Ladies, who have tried it—were you surprised at its strength too? It made his whole package shake!

The sensation was strange at first. Not pleasurable really. When the little nub on the ring connected with my clitoris it felt good, but in a dull way. Not anything that would send me over the edge, like I was expecting.

D. kept trying to reposition it, but maybe my clitoris is located in a slightly different spot than the average woman’s because we just couldn’t get it to work well. We sort of gave up on that and just resumed normal sexing, which was just fine with me. D. finished shortly after. Then he polished me off manually. And I didn’t even have to lie—his body beats a vibrator any day.

Have you ever brought toys into the bedroom? Was your guy intimidated at first? And has your boyfriend/husband ever had trouble getting it up twice in a row? What was going on?

Challenge 28

girl at laptop

The following is an actual email exchange between D. and me. I’ve put his email in italics so it’s easy to differentiate between what I wrote and what he wrote.


To: D.

From: S.

Subject: you should really take a break from work and do this…

 Send naughty texts or emails back and forth for all-day preplay. Start with “When we get home…” and see where the story goes from there. Take it away, D.

Funny you brought this up because I was just about to email you that when we get home tonight I was going to spank your butt very firmly.

That’s such a coincidence because I was going to do the same thing. But with a spatula. Aaand switching to my iPhone since I’m paranoid HR is watching my computer.

Yeah! Bring HR with you. Now we’re talking. I’ll pick you up and throw you down on the bed after that spank. What do you think?

Not if I throw you down first then rip off your shirt (the red button-down) and start licking your nipples…

That would be hot! I could grab you firmly down there and bite on your neck.

I like the sound of that. And while you are grabbing me, I’ll use one hand to grip your junk and the other to pull your hair. Then you’ll start to get hard and I’ll lean down and kiss your cut lines…

[An hour passes…]

Did I scare you off? Went for the wang too soon? Fine, back to licking your nipples…and sucking at them…

[Another hour passes…]

When I still get no response, I panic that I’ve somehow sent the last message to the wrong person. My parents? My boss? That person I once emailed about a chair on Craigslist? Who would be the worst recipient? Check my outbox before I can start to hyperventilate too much and see that yes, D. was in fact the recipient. And he was probably just called into a meeting. With HR? Because he was spending time engaging in inappropriate messaging while at work? Panic returns…]

[Then finally, a message! This is definitely one way to bring that butterflies feeling back into your relationship.]

ha ha ha! No, I was just fiddling with the rubber vibrating thing and well, I got distracted. I’m back, though. And let’s just forget that gadget. I’m ready to get on top of you and have you guide it in.

[This, readers, is when I start to get very turned on. Beforehand, I was just having fun with it, but at this moment, it feels like true dirty talk.]

Oh yeah and arrrgghh, keep pulling on my hair too.

[Yep, fully turned on. If only because I know how much he’s enjoying this.]

I’m pulling it. Your hair. And your junk. Except you got one thing wrong. You’re on bottom and I’m on top. I’m straddling you and rubbing myself all over your package. And then…


[Yes? I mean, I know guys tend to be succinct in emails, but I just told the man I was rubbing my crotch on his and the response I get is yes?]

Then I can hold all you up on my hips and pound repeatedly from underneath.

[Interesting…I’m starting to think this whole dirty email talk thing could be very revealing because it forces him to put ideas and fantasies into words. For example, I’ve never heard him say anything about enjoying the above action and it’s not as if we do it all the time. But my male mind-reading (slash email decoding) skills tell me that the fact D. brought it up here means he’s craving it. Save that little piece of knowledge for later…]

Hot. I put my hands behind me and arch my back. I lift my hips up so just your tip is inside me. Then I lower myself so your totally inside me. Deep. And I arch my back the other way, lean down and kiss you. First your lips then your neck. Then your ear lobe.

Rrrrrrr I just grabbed my junk.

[It takes me a second to realize that D. doesn’t mean he’s imagining grabbing his junk. He’s actually doing it. Aaand cue the tingle between my legs. Followed immediately by wonder as to where he was when he went hand-to-crotch.]

For real? Hot. Grab it again and imagine it’s my mouth down there. Then run your tongue over your upper lip and imagine it’s my tongue there. (How can my mouth be in two places at once? Magic.)

That worked! Damn. Now I’m grabbing your boobs and squeezing.


End scene. All of this took place over the course of a few hours. And let me tell you—when I got to D.’s place that night, I was so riled up, I didn’t need much foreplay. The key is to read the exchange right before you see the guy, too. That’s what I did. I whipped out my iPhone on the subway ride home and relived the excitement. So by the time I was at D.’s front door, my lady parts were good ‘n’ ready for some loving. And since this whole exchanged is saved in my Gmail account, I can access it whenever I want/need. It’s like foreplay-on-the-go.

Do you ever e-dirty talk or sext with your guy? What sorts of messages do you send? What do you find more arousing—seeing sexy pictures of your guy or reading a sexy email or text from him?


Challenge 29

candy necklace
  Pick up candy necklaces and slide them up each other’s thighs. Then nibble off each piece.

I sent D. to pick up the supplies and he came back with the following:

Four candy necklaces of varying color combinations.

A candy bracelet.

Two candy watches.

Please don’t say you’re going to wear the watch on your junk, please don’t say you’re going to wear the watch on your junk, please don’t say you’re going to wear the watch on your junk, I repeated silently.

D. held up the bracelet. “Guess what this is for?”

That D.! Years of knowing each other and he still manages to surprise me. Here I was thinking he’d put the watch around his shaft. And he was planning to put the bracelet around it.

We ended up putting watches and bracelets aside and opened up one of the necklaces.

I pushed D. down on the bed, he pulled off his socks (thank the lord) and boxers and leaned back with a grin.

I stretched the necklace out and carefully put it on, making sure it didn’t touch his feet. Ew. Then I rolled it up above his knee. And that’s when it started looking like it might snap. Note: These are made for children’s necks, not grown men’s thighs.

But I took my chances (hey, I’m a risk taker, what can I say?) and rolled it up until the necklace was just below his business.

“Look at me!” exclaimed D. “I’m wearing a rainbow garter belt.”

I burst out laughing. Sidenote: I laugh when D. and I hook up. Like, a lot. But I was just reading on cosmopolitan.com (ya heard of it?) that guys like when a women has a sense of humor in bed. But I do sometimes worry that we have too much of a sense of humor in bed. It’s nice at certain moments, but it’s hard to get really aroused when you’re giggling.

With all of this in mind, I decided not to let this become one big joke. “I’m going to eat your garter belt,” I said in the most serious tone I could muster for such a phrase. #WeirdestThingtoSayinBed.

I leaned down and ate a “bead”. Delish! I had forgotten how much I love cheap, nothing-but-sugar-and-probably-chemicals candy! I ate another. Then another. Then I decided I should probably not eat the entire thing and call it a day. This was supposed to be a sex challenge. Not an eating challenge.

I moved up and licked each of D.’s nipples. I left a trail of kisses and nibbles down his stomach and thighs. (OK, then I had another bead. What?! I was hungry!) I licked his cut lines and the area right above the base of his penis.

Next I took him in my mouth. He still wasn’t hard so I was able to fit his entire member inside me (without gagging). The good thing about combining oral sex and food is that you’re not at a loss for lube since you’re salivating like crazy. I alternated sucking and licking the length of his shaft and balls until he was hard.

As soon as he was, I went back to his nipples and gave them some loving.

This went on for a few minutes until D. whispered, “Oh, S., you’re going to make me come.”

And he did. Like whoa.

His entire body shook. He groaned and moaned and made the same noises the Wild Things do in the movie Where the Wild Things Are (you know, the scene when Jack gets in his boat and leaves their world). Yep, I was pretty much going down on a Wild Thing.

It was so intense and unexpected that I started to find it funny. I suppressed a snort. And another. Then D. lifted his hips high off the bed and went, “Rrrrr” almost like a growl and I couldn’t hold it in. I snorted.

So much for squashing my sense of humor in bed. Oh well, I don’t think D. noticed. And man, I really hope he didn’t. If he ever laughed at my orgasm, I would be so offended/embarrassed/hurt/self-conscious/mad/any other words to throw in here?

After he had converted back from a werewolf and into a human male, he pulled me up and spooned me. “S., I love you so much. I don’t know what it is, but I do.”

That, I had to laugh at. “You don’t know what it is?” I asked.

“Well, yes it’s that. But also, there’s just something about you that is really great and cool.”

Aww. Even if it was post-orgasm, I couldn’t help but smile.

Would you try this challenge? What’s your feeling on food in the bedroom? And also, have you ever laughed at your partner’s orgasm face or sounds? Has he ever laughed at yours?

Challenge 30

  Play strip trivia. Ask each other questions like, “What’s my favorite restaurant?” and “Where was our first date?” Whoever answers incorrectly has to remove an item of clothing.

Warning to readers: Part of what I’m about to write is not sexy. In fact it’s so unsexy that I felt the need to do a redo. But I wanted to be honest with all of you, which is why I’m sharing both stories: The first attempt, which made me feel like D. and I were a couple who’s been together for 40 years. And not in an awww cute way. In a we are waaay too comfortable, this-is-getting-asexual way. Ugh. The second attempt made me feel like D. and I were a couple who’s been together for, oh, three days and couldn’t get enough of each other.

I had emailed D. earlier in the day to say, “By the way, we’ll be playing strip trivia tonight. Start coming up with ideas.

D. came over to my place after work and we ate dinner…in pajamas…in front of the TV…me, faux complaining about how when we watch DVR’d shows, he’s so bad at hitting Play at the right time so that we don’t see any commercial, but also don’t miss any of the show. I know, a picture of romance, right?

Finally, I stood up and turned off the TV. I was going to turn this runaway train of unsexiness around. Right after I picked off the piece of rice that had fallen from my sushi roll and stuck to my yoga pants. “Let’s get you out of those clothes,” I told D. with a smile.

We went into my room and he lay down on the bed in a pin-up pose, which made me laugh out loud, but didn’t do much for my libido.

“OK, how does this work?” I asked, standing over him. “I ask a question and if you get it wrong, you take something off, right? But what about if you get it right?”

“Then you take something off,” he responded.

“Yeah, except I’m only taking off my shirt. And I’m not wearing a bra. And I don’t feel like putting one back on. And maybe I’ll take off my pants, but nothing else.”

“How fun for me,” D. said, sarcastically, but I knew he was only half-serious. “Are you serious?”

“I feel like crap, I’m having a fat day, so yeah, I’m serious. So ask easy questions that I’ll get right.”

We got into bed and I started. (Note: I’ve slightly changed some of the questions and answers so they don’t give away our secret identities!)

“Where did I first say I love you?”

D. got a big grin on his face. “Ohhh easy one. I can’t forget that. Over brunch the morning after a party at Sarah’s.”

Ding ding ding. I took my shirt off…at least halfway. I was exposed, but it was still on one arm. He went next.

“What is my brother’s middle name?”

“Start taking off those socks because I so know this. Also because you’re wearing socks with shorts. In bed. Garrett!”

D. slowly reached down and coyly removed his socks then threw them in the hamper, the whole time maintaining eye contact with a lusty gaze.

“What was my first pet’s name?” I asked.

He mulled it over for a while then exclaimed, “Pepper! Because the dog was white and black!”

I have never owned a dog. And I’ve never owned a pet named Pepper. Nor have I owned a white and black pet. Or a pet with fur. “I appreciate your enthusiasm, but no. It was a guinea pig and her name was Lollipop. Get naked.”

He took off his shirt. And readers, here is when I started getting really tired. I know it’s lame. But I was exhausted! And not even a hot male chest would get me going. Lame, lame, lame I am.

“What was the name of the restaurant we went to on our first date?” D. continued, unaware of my drowsiness.

“Frank,” I mumbled and I watched him take off his pants.

I don’t remember much else after that. D. tells me we went through a few more questions, but all I know is that the next morning I woke up with my shirt tangled around one of my arms, next to a boy who was naked all but for his boxer briefs.

Duh. Press. Ing. Seriously, I had a moment of panic that morning. Like, Is this what’s become of us? Are we that couple? I had that thought in the back of my head all day and while I didn’t really think we were going to turn into some sad, sexless relationship overnight, I was worried that this could be a taste of what was to come. I know you’re probably thinking I’m overdramatic and that any girl could be expected to act the same way from time to time. But there was something more going on. Something I’m having trouble putting into words. But it just left a pit in my stomach that gave me a bad case of the uh-ohs. And even if it—it being a sexless relationship—didn’t happen for ten or twenty or fifty years, I was worried.

So that night when I got to D.’s apartment that night, I turned the runaway sexless train around. And for reals this time.

Luckily, his roommate was on a business trip. Every more luckily, I wasn’t having a fat day. The sex gods were smiling down upon us.

I had met up with a friend for a glass of wine beforehand and was feeling uninhibited and frisky. A good combination. As soon as I walked in the door, I pinned D. up against the wall and kissed him hello. On his right nipple. “Honey, I’m home,” I whispered while taking off his shirt.

He looked dumbstruck. Probably because of my 180 transformation. I kicked off my ballet flats, took off my dress, then lead him into his bedroom wearing just a bra and boyshorts.

And from there, here is what happened: missionary, girl-on-top, doggy style, oral sex (performed on him), up against the wall, missionary with my head hanging off the bed. And I was loud. Porn star loud.

I came, he came, we all came.

I woke up the next morning with a shirt tangled around my arm. Except this time it was D.’s shirt, not mine which I had fallen asleep half-wearing like the night before.

Have you ever had a moment of panic like I had, when you realize you might be headed down a very unsexy path with your guy? How did you turn things around? And back to the challenge: Have you ever played strip trivia or strip poker or strip anything else?

Challenge 31

  Give him a lap dance. But in this strip club, he’s naked too.

I always get emotional when things come to an end. I cry at graduations (even those that aren’t my own), I put off finishing good books (seriously, I have probably a dozen novels that I’ve read all but the last 10 pages), and you don’t even want to know what I look like after a breakup. Let’s just say, waterproof mascara’s got nothing on me. And when the 77 Positions in 77 Days blog ended, I definitely felt a pang of nostalgia. And it’s happening again with this blog. When I asked D. if he felt the same way and jokingly mentioned he was going to cry about it, he said, “Sure. If by crying, you mean my penis will do the crying, you’re right.” So poetic. So romantic.

Anyway, I saved this challenge for last because it’s a bit of a doozy. You know that I’m not always totally comfortable flaunting what I’m working with. Obviously, I’m pretty damn confident (enough to do this and this ), but a striptease/lap dance is a whole new kind of confidence. And I thought it would be good to go out with a bang. Quite literally.

D. was already at my apartment when I got home (yes, he has a set of keys, something I thought would feel much more momentous than it really did). I had purposely worn an outfit that would work well for a striptease. Nothing but a red G-string and tassels on my nips. Kidding. I was in a flouncy skirt, tee, scarf, and heels. Skyscraper heels that almost gave me a twisted ankle like five times during the day. The things I do in the name of hot sex!

As soon as I got home, D. said he was starving and started rummaging around in the fridge for something to have for dinner. Knowing that a big meal after a long day would do a number on our sex drives (and my I-feel-so-hot mentality), I pulled him away from the kitchen and pushed him onto the living room chair.

And that’s when I made my first mistake.

When you remove your clothing during a striptease, you shouldn’t then put the items on him. Seems so obvious now. Actually it seemed so obvious as soon as I removed my scarf and wrapped it around his neck then promptly burst out laughing.

“What do you think of my ascot?” D. asked in a British accent.

“OK, uh, take that off. And uh, take off your shirt.” Wow, what a hot stripper I am, I know.

But then things got sexy again. He took off his shirt—and my, were his abs looking good (gotta remember to compliment him on those later)—and I got on my knees and started kissing his chest and shoulders.

Next I roughly unbuckled his belt, pulled it off, and used it to playfully smack him then myself.

D. laughed, but I could tell he was getting into it.

I stood up and pulled off my shirt very slowly. The key, I’ve learned is to draw out every movement when you’re stripping. The slower the better. You want to keep him on a low simmer. I turned around so my back was to D. and leaned down to grab my ankles, shaking my booty as I did.

“Holy shit,” was all that came out of D.’s mouth.

Oh, what’s that you say, I thought. You noticed my incredibly hot new underwear? Black lace, Brazilian cut, for the record. Pick up a pair right this instant. They are so damn flattering.

With my skirt still on, I leaned back so I was almost sitting on him, but my arms were supporting me, using the arm rests.

I rubbed myself against his crotch, feeling that he was hard already. (“I’d like to thank my waxer and my Brazilian cut undies…”)

Then I stood up and pulled down D.’s pants. But his shoes were on and I didn’t feel like taking them off. Something about it felt very unsexy, like I was caring for an elderly relative or something. So he was sitting there on my red Pottery Barn easy chair, pants and boxer-briefs around his ankles, with his member standing at full attention.

I dropped my skirt and my underwear followed. I left my shoes on too. But for other reasons. Those reasons being that I was channeling my inner stripper. And I don’t know about your inner stripper, but mine leaves on her heels.

And that’s when we heard keys. As in the roommate’s keys. Outside my door. D. panicked and bolted upright. I ran into my room and without thinking, slammed the door.

“Are you kidding, S.?” he asked, out of breath, after he’d joined me in there. He had waddled in after me, pants around his ankle.


A moment later when no one had entered the apartment, we realized it was probably the neighbors across the hall whom we’d heard. So we resumed our places. D. hadn’t lost his erection, which surprised me. I was worried it would have thrown off his game. But nope!

I did some more ass-on-crotch grinding then I got down on my knees and took D. in my mouth.

“Holy shit,” he said for the second time that night. (I took it as a good sign.)

The angle made it really easy to make eye contact as I went down on him. So I did just that. I made sure not to make it a staring contest. (I read in last month’s Cosmo that guys like eye contact but only to a point.) And it was a huge turn-on to watch D.’s face as he experienced every bit of pleasure.

The only drawback to this position is that I couldn’t get at D.’s balls. So I decided to grab his butt with my hands instead, pulling him deeper into my mouth. I also employed the good ol’ hum-while-you-go-down trick, which got yet another “Holy shit” out of D. Quite the curser, that night!

D. orgasmed quickly and I got to watch the whole thing unfold because of my viewpoint. He threw his head back, squeezed his eyes shut, and his hands got all shaky. (For those of you just joining, I am in fact describing a climax, not my boyfriend having a seizure.) And his whole torso seemed to tense up with ever wave of the orgasm. Fascinating stuff, ladies. Sort of like being a scientist in a sex lab.

D. lay there for a full minute with a big grin on his face. “You are awesome, S.”

And then I blurted something out:

“I think you’re The One for me.”

Whoa! Where the hell did that come from? I asked myself. Not that it’s not true. But we don’t really talk like that.

“Hell yeah,” he responded. “We have such a good time together.”

Sigh of relief. He hadn’t taken it to be some marriage proposal or something (it wasn’t, for the record) or big announcement. Maybe he hadn’t realized I’d capitalized “The One” in my head. When it’s lowercase, “the one”, it doesn’t sound as daunting. You know, like, “Which muffin would I like? The one right there.” or “I like the dress with the sequins, but I like the one with the beading more.” Not like, “You are The One and only for me.”

A few minutes later, we were standing in my kitchen making grilled cheese sandwiches when he took my face in his hands and kissed me long and hard. “S., we really do have an awesome time together. I love you so much.”


I got a little teary when he said that. Partly because I knew it would be our last challenge for 31 Days of Hot Sex. But I have good news for you ladies. This won’t be the last you see (or rather, read) of me. I’m working with Cosmo on something really cool and I think you’re going to love it. Stay tuned!

Did you try  of the challenges from this blog? What was your favorite? Which was your guy’s favorite?

Send us your comments and you don’t have to reveal your identity.
















culled cosmopolitan

Filed in: News, Relationship & Family

Leave a Reply

Submit Comment

Confirm that you are Human *

© 2018 Giant Comfort. All rights reserved. XHTML / CSS Valid.
Powered By GiantComfort.