Meeting a stranger, taking him home, pegging him slowly [f/m] | 2016

I guess you could say it started my friend Maria. Maria is a designer. She's not rich or famous but she has this wonderful little studio where she creates her own clothes and a few boutiques carry her line. She's also involved in local theater and she has created costumes for a lot of small plays in the city. Whenever she works with a theater troupe, they usually offer her a couple of tickets for opening night. Every once in a while, she invites me to go along as her "date". I'm always happy to accept, because not only does it mean a free show but usually we go backstage afterwards and take part in the post-opening-night festivities.

Maria called me that afternoon saying someone had offered her tickets for a show that evening and would I like to go? The play was put on by a group of young Danish actors who were only in town for a week, friends of a friend of Maria from what I gathered, and they performed for a couple of nights only at a small but well-respected venue. I didn't have any plans for that evening so I gladly accepted. I try to keep up with trendy experimental stuff and it's always fun to meet people from other countries.

Maria had casually warned me that this particular show had some adult content. She knows I'm always open-minded about that sort of thing and I guess that's why she didn't make a big deal out of it, but boy! That play definitely was something! The story was about this love triangle between two men and a woman and there were a lot of scenes where the actors were naked on stage. And I was finding out that the theater isn't like the movies where the director can position the camera in just the right way to make sure that not too much is shown. I could really see all of the actors, close up and from every angle. It was such a small venue they were maybe a dozen feet away from me, sometimes arguing and shouting and yelling, and sometimes whispering sweet words to one another, caressing, kissing and... groping! All three were in their early twenties, young and beautiful, and seeing them naked right in front of me I was definitely a bit flustered!

The atmosphere backstage after a first show is always a bit electric. People are excited, happy to have finally broken the ice, but there's still some anxiety in the air, worries about the audience's reaction, discussions about what to do differently the next night, etc. I tried my best to compliment everyone to let them know how much I liked the play, figuring that since my ticket was free I should chip in by making all involved feel good about what the work they'd done.

I didn't know anybody there other than Maria and she had other friends to talk to so I quickly ended up on my own. That was fine with me since I'm usually pretty good at meeting new people. I talked to just about everybody. Most of them were young and only a few years out of school, many hipster types with the kind of cool demeanor I was never able to pull off, even in my younger days. I hate to admit this but I had a good ten years on most of the people there! About half the room were Danes and the rest were locals. I don't know if it's because of age or cultural differences but initially conversation was a bit stiff and it was hard to find something to talk about other than the standard unexciting platitudes. Slowly though discussion drifted toward our limited shared experiences: the play, the people in attendance, the actors on stage, the naked actors on stage, public nudity and, finally, sex. Maybe it was because of what we'd just seen on stage, but people were oddly interested in sex that night! And pretty soon I found myself discussing dildos and strap-ons with people I'd only met minutes ago...

I can be pretty open about my sexuality given the right audience, but I usually don't dive in so quickly! Perhaps deep down I wanted to show these kids that I too could be cool and edgy. I don't know. But that night, after seeing that play, the mood certainly lent itself to it! Pretty soon I had a handful of guys and gals around me and I was entertaining them with my tales of silicon sex, doing (I hope!) a pretty good job at convincing them how fun and liberating and empowering a good dildo and harness can be.

In the three years since my boyfriend and I started experimenting with pegging, I discovered that a surprising number of guys are curious about anal play. It's not like I'm walking around with this sign that says "I peg" around my neck, but as you can probably tell I'm not shy about my sexuality either. One way or another these curious people eventually find out about my bedroom activities (sometimes more quickly than others!) Guys more than girls are usually less shy about asking me questions about it: how did I start? Is it something I do often? What does my boyfriend think about it? And often, after some beating around the bush: so where exactly does someone find a lady that's into that sort of thing?

Over the years I've received literally dozens of requests from guys who wanted me to peg them. Of course they don't usually come right out and ask then and there, although that too has happened. What typically happens is that a few days after our conversation I'll get a text, or an email, or a Facebook message from the guy. At first it'll be really innocent, just a note saying how great he thinks I am. That nice little compliment usually leads to another question or two, like he's casually continuing the conversation from the night before. Only after the exchange has gone back and forth a few times does he feel comfortable enough to finally come out and ask. (Of course some situations are different... I won't tell you how many PMs I received after my last two stories!)

I've always turned down these kind requests from strangers. I try to be polite and positive because I don't want the guys to feel bad about wanting to explore this side of their sexuality. But I'm in a relationship and pegging is sex, and sex with someone other than your partner is usually not ok, or at least it's something you have to discuss with him or her ahead of time (of course every relationship is different so as they say your mileage may vary). Besides, if a guy is going to just come up to me and offer me sex I'll almost certainly turn him down. It was true back when I was single and it's even truer now. Sex only for sex isn't something that's all that attractive to me. There needs to be some special spark to get me going, there has to be something about the guy that excites me. It doesn't have to be anything big: often I find it's all about the way he presents himself, the way he acts or the way he talks, or what he talks about. Some shared kink or some common experience is sometimes all that's needed for me to feel a connection. But sometimes, like that night, I can be a bit more superficial...

As I was talking about my sexual proclivities, a tall young man came up to me to listen in. Now I'm not usually dazzled by a good looking guy walking up to me, but oh my! That guy sure had something about him! And normally I don't go for pretty men (and in this case with the age difference, I could almost say pretty boy!) I generally prefer men that are a bit more rugged, more flawed, more real. But this guy looked like a young Matt Damon, without the floppy hair of Good Will Hunting. He had broad shoulders without being too muscular, a good chest, good hips and strong legs. And he had the kind of presence that commanded everyone's attention. All eyes immediately turned toward him and everyone else just naturally quieted down just a notch.

He told me his name was Magnus. He had a girl with him whose name I forget, so I'll refer to her as "his girlfriend" but really I didn't get a girlfriend vibe coming from her. She was a local and I'm not sure how long they'd known each other, but they talked like they didn't have that many shared experiences; a lot of "me" and "you" and not many "we" or "us". Anyway, both of them joined in the conversation and Magnus particularly started asking about the dildos and harnesses and positions and so forth; the typical line of questioning that I've answered dozens of times before so I like to think I can make it sound funny and interesting and intriguing. He seemed particularly into it. He had this way of directing the conversation without monopolizing it, the cool confidence of someone used to lead a crowd. You know how sometimes you have a hard time choosing a restaurant to go to with your friends? Everyone's standing around after a movie or something trying to decide between Chinese and Italian? Well Magnus talked like the guy who just showed up an hour late and tells everyone they should go for that new little Afghan place that just opened around the corner, and everyone agrees! I've always had a soft spot (or a tingly one!) for guys like that and Magnus was no different...

Pretty soon it was just the three of us and still Magnus was quizzing me as his girlfriend looked on. So what kind of dildo is best exactly? Why? What's my favorite position? Does my boyfriend moan when I fuck him? Did I wish he did? So at some point I simply tell his girlfriend "You know if he is that interested, I can tell you where to go to get a good dildo." But then he answers "Actually for my first time I'd rather do it with someone who knows what they're doing. Like you!"

At first I thought he was just kidding. My God I wish I could have seen my reaction when he told me he wasn't! My mouth just dropped. I'm pretty sure I literally stayed there, mouth wide open while I stared at him. I just had absolutely no idea what to say! I've had this asked of me before, but never quite like this! His eyes were locked onto mine and he had this confident, focused, serious but playful air about him, the kind of discreet swagger that must have come from never having any girl (or any guy!) tell him no. And it worked! He was the one asking me to fuck him, yet it felt like he was in control, like I was the one asking something of him! And for a moment my thoughts drifted back to these three Danish actors on stage, naked, kissing...

I looked for words to stall him a bit. "Well maybe one day if we meet again..." "What about tonight?" "What do you mean..." "I mean we could do it right now" and he turned to his girlfriend "Do you want to come and see me get fucked?" Oh my! Now that's really not how this usually goes! Guys who ask me to fuck them don't usually want to bring their girlfriend along!

I tried to be quick and think on my feet, but really I just drew a blank. He was so young, so hot, so different from the guys I'm used to... I wanted him! That almost never happens to me but this time I really wanted to have sex with this guy! I had never popped any guy's cherry before... Of course there was my boyfriend, but I'd been a virgin myself when that happened so it didn't really count since I didn't know what I was doing (and when I say virgin of course I don't mean literally, I just mean we had never done that before) What would it be like now that I was more experienced and could really focus on the moment, without wasting all this energy just trying to figure out how everything worked?

Of course there was my boyfriend. I really meant what I said earlier about not doing anything (or anyone!) without your significant other's approval. I tried to call him but didn't get a reply. I knew he was at home so I figured he was probably in bed already. What should I do? I figured trying to explain all this over the phone was probably not the best idea anyway so I told Magnus and his girlfriend to get us a cab, I was taking them home.

As soon as we got to my apartment I pointed Magnus to the bathroom, handed him a towel and asked him to shower. Partly because sex is always nicer when the guy's all clean and has that nice soapy perfumy smell, but mostly because that would buy me some time to talk things over with my boyfriend. As I suspected, he was in bed and fast asleep. I got in between the sheets and woke him up in the most pleasant way I know! By the time he had come to his senses he was fully hard and my head was bobbing up and down his erect shaft. "Oh hi... what time is it...?" I pushed myself up to get on top of him, lifted up my dress and took him in me. "Honey... I have something to ask you" I said as I very slowly ground up and down...

From there I asked, I cajoled, I flattered, I seduced, I titillated, I pleaded and I begged, and I promised a hundred naughty things if he would let me have my way for that one night. In the end though, he wasn't really all that difficult to convince. The idea of me pegging a guy in front of another girl was almost as much a turn on for him as it was for me! His only condition was that this would be only a one time thing (no problem there since that's also what I wanted) and that he'd be allowed to watch (which was also easily arranged).

When Magnus came in from the shower with a towel around his waist I had all my equipment ready. His girlfriend had showered too but my mind wasn't on her right then. I had him lie down on the bed and when I took the towel away from him I saw that these two already had some fun in the bathroom because he was still half erect! Lying on his back I pushed his knees up and settled in between his legs.

I took it very slow since this was his first time. It's always better to first get into the mood to make things more enjoyable later on! I grabbed the lube and spread some generously over his cock. He was a tall guy and he was pretty long down there too! I don't usually put too much importance to that kind of stuff but it's always nice to be able to get a good grip. I slowly stroke him up and down all the way to the tip of the head and gently traced circles with the lube around the crown. I cupped his balls and ran my fingers on his lower abdomen and upper thighs with my other hand. His hair was very very short and my lubed hand glided easily over his skin.

I teased him like this for a good long time, waiting until I felt him fairly close to coming. Only then did I dip a finger lower, running along the crack and on either side of his asshole. I felt him get even closer so I let go of his cock and focused on his ass. I applied more lubed and ran my whole hand inside the cheeks. On every pass my fingers would linger longer and longer over the hole, massaging the muscle all around and getting it slick and wet.

I always like to take it slow for this part because it looks like it feels so pleasurable and I enjoy watching the guy's body responding to my touch. It's just such a turn on to have a guy like putty under my hands, to see the look on his face when I caress here, or touch there, or press a finger softly just over that spot... It's such a strong visual and it always gets me wet and ready! But it's also fun to make the pleasure last a little longer, and continue the slow pace for a while...

He was breathing heavily and his cock bobbed up and down each time my fingers pressed against him. He didn't make a sound but just laid there with his arms flat on the bed on either side of him, completely relinquishing control. That was a bit of a surprise for me (I thought somehow he would have wanted to direct the action) but I took it as my cue to take charge and I just went along with it. His girlfriend was sitting next to us on the bed wearing only a towel, her eyes focused on the movements of my fingers. Every once in a while she made some comment like "Does that feel good baby?" but I kind of wished she would keep quiet; I was really enjoying this silent massage. My boyfriend was standing back some distance, but I could see his whole attention was on what I was doing.

When I pushed a finger in he tensed up but stayed quiet and still. By then I could sense he was ready: his relaxed muscle would open under the lightest of pressure from my fingertips. I left my finger there a while to let him settle and with my other hand I squeezed and jerked his cock back to a full erection. I went in like this two or three times, applying more lube each time until his slick hole offered no more resistance. I curled my fingers slightly inside him to probe and caress the sensitive area close to his cock. I felt the tension build up within him and I squeezed his cock hard to milk some precum out of him. Only when I felt him close to bursting did I strap in.

He still lay there calm and quiet with his eyes closed, his cock a hard rod jutting straight up into the air. His girlfriend's eyes were wide staring at the length of dildo as I put it on! I had chosen my favorite one: a long purple silicone cock with a bulbous end that I wear inside me and that rubs and caresses me with each thrust. The sight of it can be impressive the first time: it's not really much bigger than a regular cock, but I remember worrying it would never fit inside my boyfriend when we first got it! Turns out though, not only does it fit, but we found that a good girth provided more stimulation for him and the length of it made it easier to manipulate for me.

My eyes were on him when I pushed the head in. He frowned and held his breath for a moment, but then relaxed and exhaled once his ass adjusted to this new feeling. Again I stroke his cock and with lubed fingers massaged the stretched muscle around the dildo. I stayed like this a long time, my hips not moving, giving him time to ease into the position. Eventually he's the one who started slowly pushing himself toward me...

I only pushed back hard enough to offer some resistance, making it easier for him to slide himself over the dildo. Slowly, inch by inch he pushed until my hips finally made contact with his ass. Only then did I start thrusting, very gingerly at first. My hips moved back, pulling the length of the dildo out of him, and then slowly moved forward to fill him back again. Again, slowly, out then in, out then in.

"Jerk him off but don't let him come" I figured his girlfriend should make herself useful. My own hands I used to lift his legs up, high and spread wide to give me easy access to him. I also used his legs for support and I leaned slightly into them to help me keep my balance as I quickened the pace slightly.

The movement of the dildo slowly built up within me. The sensations grew stronger and more intense with each push in and out. I took a deep breath and continued at this torturous pace for a while, enjoying the anticipation and the agonizing thrill of this slow gratification. My body was pleading for me to give in, my clit was screaming for attention, but I continued this deliberate pace for a while longer, concentrating on the naked body in front of me, his eyes still shut, his features relaxed, his chest expanding with each breath, his cock large and swollen in his girlfriend's hands.

Finally I couldn't wait any longer and lust took over. His calm demeanor finally broke when I started pushing in harder and deeper. First he frowned, then his mouth gaped open as he sucked the air in. He grunted and moaned and finally opened his eyes and stared at my hips thrusting into him, at my breasts bouncing with each stroke, at my eyes locked on his body. We both held the gaze for a moment, one thrust, two thrusts, three thrusts, until he closed his eyes again and threw his head back.

The sight of him under me had me going like crazy and I let go of his leg and reached into the harness for my clit. "Make... him... come" my own breath was ragged as I commanded his girlfriend. I wanted to see his orgasm, to see his face under the strain of it, to see his cum come gushing out. It became harder to control the movement of my hips I was so focused on my own pleasure. My thrusts became more jerky and erratic. His own grunts got louder with each wayward lunge which only made me even more worked up and frantic.

He came first.

He let out a moan and his seed gushed out in a heavy milky flow over his stomach. One, two, three, the fourth spurt spilling softly over his girlfriend's fingers. My own orgasm followed not long after and my thighs strained and pushed me up stiff and still as I let each wave wash over me. My eyes clenched shut and for a while the whole world disappeared. There was only the pleasure rolling over my body, the tight grasp of my hand under his knee and the fullness of the dildo inside me.

When I opened my eyes I found him staring at the mess on his stomach. He pushed himself up on his elbows and looked up at me, then down at the dildo still inside him. He didn't say anything but just let himself drop back down heavily on the bed.

And that was that.

I wish I had some sort of epilogue for this story but I don't really. Magnus and his girlfriend left soon after and I never saw them after that. My boyfriend said he enjoyed watching me fuck that night but doesn't feel any particular inclination to repeat the experience. As for me, well... That was one hot night and I'm happy that I now have this memory to carry with me.