Summer Fuck-Buddy: Second Time Even Better



What’s your gender? Man
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Seattle
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Photographer
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Queer
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? This is my second

Summer Fuck-Buddy: Second Time Even Better

How long ago did this hookup happen? 13 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a month

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was 18, I was 19. She was a medium-tall woman with black hair and pale white skin, pretty face and amazing body. She worked out and had a great physique, and on top of that she was super curvy, with huge breasts that were absolutely perfect. I had noticed her when she started hanging around my group of friends during a summer back home from college, but I didn’t feel terribly attracted to her until she set out to make me her summer fling with some less-than-subtle seduction that brought me around very fast. I wrote a previous story about that first night when we went from acquaintances to fuck-buddies (I called it Summer Fuck Buddy – The First Night, if you want to check it out too), when a night of playing video games turned into some incredible mutual oral. She had given me the first blowjob of my life, which remains one of the best I have ever had. We started hanging out a lot over the next week, almost every day – mostly as friends, playing video games and frequenting record stores and such – but most of our hang-outs ended with us going down on or fingering/hand-jobbing each other. I mean, we were teenagers with a friend who wanted to make us come; neither of us could keep our hands/mouths/genitals to ourselves for a whole evening. But that said, neither of us necessarily felt ready to go full-on fuck-buddy and have sex; we had both only slept with one person up until that point, and both wondered if sex was something that should be saved for the next relationship. Somehow friendly oral seemed perfectly innocent and fun, though. Until one night, the urge to fuck was just too strong to resist.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were hanging out one night, and my parents weren’t home. We had been out around town for a while, and had just picked up some carry-out to take back to my place and eat, since we had the house to ourselves. Of course, given the nature of our friendship, house to ourselves pretty much equated to “we can fool around and be as loud as we want,” but I figured we’d hang out for a bit first. I asked her what she wanted to do – maybe watch a movie or something? She responded with – “do you want to watch some porn?” That was something new – I had never watched porn with her or anyone else – but what the hell, why not?

This was 2003, so I actually had a handful of porn DVDs sitting around. I’ve always been very picky about porn – I’ve always hated the usual shallow, creepy, mainstream stuff that feels very objectifying to its female stars and apathetic towards whether she’s enjoying the sex or not. Sex-positive, female-pleasure-focused porn was always my go-to; women who had pubic hair and didn’t look like they’d gotten plastic surgery to get the role, and a focus on her feeling good, and having what was hopefully a real orgasm. This made it pretty good porn to watch as a couple, and soon we were both quite horny, rubbing our crotches through our pants, and looking to each other for a visual cue for whether or not it was ok to open our pants and start masturbating.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Before long, we decided that yes, that was totally ok, and our pants came unbuttoned and unzipped, though we left them on. She reached into her pants and started rubbing her clit, and I pulled out my penis and started stroking myself. Soon, watching each other masturbate was way hotter than the porn – I learned right then that I love putting on a show by masturbating for someone, and I love seeing my partner masturbate in front of me.

It didn’t take too long for us to take advantage of having the house to ourselves: she tore off all her clothes and laid down on the carpet of the living room, continuing to play with herself. Since we had never had a house totally to ourselves before, this was actually the first time I had seen her completely naked from head to toe: usually it a shirt around her neck, pants around her ankles, or pleasuring her under a skirt that was still on, in case we heard any parent coming up the hall. Even though I had seen every part of her already, the sight of having her finally completely nude (on the floor of my family living room, no less) was a massive turn-on. While she had shaved her crotch before that first night, when I mentioned to her that I am a pubic-hair fan, her response had pretty much been “thank god, I hate having to shave there,” and she had let her bush grow out for the last week since then (I hate the societal pressure on women to shave if they don’t want to – misogynistic bullshit. Grow it if you want to grow it, or shave it if you want to shave it, but don’t let fucking Playboy or whatever media awfulness tell you you what you should want). Her black-haired bush growing against that goth-white skin just made her look even hotter nude. Soon I joined her in nakedness, and was kneeling beside her, kissing her nude body while we both continued to play with ourselves. As I was kissing her breasts, I was kneeling in such a way that my penis was pretty damn close to them, and on a whim I caressed my dick across those soft, huge tits that were such a turn-on to me. Then she said something I honestly never expected to hear: “have you ever tit-fucked a woman before?”

No, I never had. Had she, I asked? She told me that yes, her ex had tit-fucked her a few times, and she thought it was pretty fun. “Would you like to try?” she asked. As I rubbed the tip of my penis across one of her nipples, it was obvious that the answer was going to be yes. “Just one rule – ” she said, “if you come on me you have to lick it up.” Given that, as I said in my previous story, I’m bisexual and tasting cum was something I found kinda hot, that was absolutely a deal!

As she continued to play with herself, she invited me to climb on top of her, straddling her chest. I slid my penis between her breasts, and she moved both hands up to them and squeezed them together around me. As I moved in-between them, it definitely felt really good. And when I thrust myself all the way forward between them, she would reach her face towards my penis and give the tip a little lick. But I’ve gotta say, I felt a bit weird doing it. I felt selfish, since this was something that I couldn’t imagine she was getting much out of. That made it harder to enjoy; I wanted our hook-ups to be equally pleasing to the both of us. Our oral was always mutual; this felt too one-sided. This isn’t to say it wasn’t hot, and it wasn’t making me feel pretty damn good, but it lacked the fulfillment that giving equal pleasure to her brought. I said that to her, and said I wanted to do something that was good for her too. What would she like? “Do you have any condoms?” she asked. Yes, I did – I had bought some that first night just in case. And I must admit, at this point I was more than ready to use them, but I know she had been hesitant about going all the way just as friends. I asked her if she was sure. “Yes! Get one!” was what she said in response.

She didn’t need to ask me twice – I got one, and put it on while she resumed fingering herself. I moved to go down on her for a bit before we began, but she stopped me. “Just get up here and fuck me!” I loved her directness. I did as she asked – I moved up, positioned myself on top of her, and guided my penis into her. Holy fuck she was tight! She was so. fucking. tight. Her muscles squeezed my dick unbelievably hard; it was the most incredible sensation. I asked to make sure it wasn’t hurting her, since it was so tight – “no, it feels great! I just have a small vagina – but it can handle it, believe me.” I slowly moved within her, wanting to be gentle until I knew just what she liked, since I was sure such a tight vag is extra sensitive. I quickly realized that slow and steady like that was exactly what she liked – she moaned with pleasure and wrapped her arms and legs around me. Then at one point she asked me to just stop for a moment and leave myself fully inside – “I just want to feel you inside me for a minute,” she said. It had been a long time since either of us had had sex with anyone, and we both savored the moment. It didn’t take me long to realize, though, that I was not going to last. Between how absurdly tight this woman’s vagina was, and how much time we had spent masturbating, I was way, way closer than I wanted to be. There was no way I could hold on much longer, as the squeeze of her muscles made every thrust feel like the last one I’d be able to take. I stopped for longer and longer periods between each movement, and she could tell what was going on. “Are you going to come?” “I’m sorry,” I said – “I can’t hang on much longer!” Then I thought about it – while I knew I couldn’t put this orgasm off short of stopping altogether, which I know she didn’t want any more than I did, I also knew I had enough stamina (and enough cum) to keep going beyond one orgasm. I felt like such a selfish lover to ask it, but I also didn’t know what else to do to make myself last any longer. “May I come, and then change condoms and keep going? I know I’ve got enough in me for more than one round!” “Of course,” she said, in a voice more understanding than I had feared. She later told me that her ex had had quite a bit of trouble lasting long with her the first few times too. “Ok,” I said, and kissed her while I resumed slowly moving, this time being unafraid of how close it was getting me. It only took a few thrusts before I came inside her. She clutched me even closer when she could feel me start to come, and kissed me deeply while it happened. I could feel the tight resistance of her muscles squeezing me as my orgasm squeezed back; I was honestly afraid that the condom would break from the pressure. Thankfully, when I pulled out I found that it had not. I took the condom off that disposed of it, and then returned to her. This time I did go down on her, as a thank you for being so understanding. I wanted to give her an orgasm too, but before I could she told me it was time to come back up and get back in her. I was almost fully hard again, but she gave me a little bit of oral to get me all the way there, and I got a second condom.

Since the feeling of entering her super-tight vagina was so intense, I wanted to savor it, and also have a bit of fun returning some of the teasing and build-up of anticipation that she liked giving me. I teased her for a bit, rubbing the head of my penis across her bush, tracing her labia and rubbing her clit with it, and putting the tip partway in and taking it out again to caress the contours of her vulva some more. This really got her going, getting gasps from her every time I started to put it in and then pulled back. She even laughed a bit each time I’d go a little further in and then back out. Finally, once we were both thoroughly revved back up from the tease, I plunged fully into her, and she again pulled me close with her arms and legs. Thankfully, having just come gave me just the stamina and longevity I needed to be able to last long and give her the love-making she wanted, with a few more tips from her about what felt good along the way. It was really, really hot: we were both grinding against each other so passionately, holding each other so close, kissing almost constantly, and getting very, very sweaty. By the end of it, we were both positively soaked. As we went along, I could feel her muscles twitch and tighten even more as she responded with near-orgasmic pleasure (though I don’t credit myself as being any great lover for doing this; just a good listener who paid attention to her helpful directions and her moans and breathing to find the right ways to move for her – communication is everything!). As she got closer, the muscles of her vagina just got even tighter – the feeling was even more mind-blowing than before, and at one point her muscles tightened so much that I popped out of her completely, and almost had trouble fitting back in! She told me to be careful to keep it inside her from now on, because it’s only going to get harder to fit back in from here on out – she was on the final stretch. So was I – it had been maybe twenty minutes or half and hour since we had resumed having sex, and she was getting me very close to the edge all over again. I asked her if she was close to coming, and she told me helpfully (again, communication!) that she can never get more than just close to orgasm from a penis; she needs her clit stimulated at the same time to finish. I reached down and started rubbing her clit as I slowly fucked her; her breathing and movements started to get heavier and more intense almost immediately. “More! Faster!” she said to me, grabbing my back and digging in with her nails. I started rubbing her clit faster, and fucking her faster as well. “More!” she said again. I was right about to come again. I rubbed her clit more, and started thrusting into her as hard as I could. “Fuck! Yes!” she yelled. There was no more hanging on for me, though – it was so intense that I started to come, although I kept rubbing her clit all the while. Fortunately, that last bit of fast stimulation did the trick – right then she came too, and my orgasm rolled into hers, our bodies spasming together. The feeling of her orgasm around me was incredible, and I think it squeezed every drop of cum I had in my body out of me. We collapsed into each other’s arms and kissed; a sweaty, sexy mess on my parents’ living room carpet.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? The rest of that night was fantastic, as we stayed on a high from the great sex. The next day we talked, and she said she felt conflicted about whether it had been the best idea to actually have sex while we were basically just friends, or if it had been a bit too slutty of us. She didn’t regret it, she said, but she wondered if it was irresponsible. By that next evening, though, when we were getting to the time of day when we were not only both horny, but were able to do something about it with our parents asleep, she said that she had decided that no, there was definitely nothing wrong with it, and she wanted to again. A repeat performance followed. I still had great trouble lasting the first time around in that tight vagina – double-features became our standard method of sex that summer, though I tried to always make sure she had at least as many orgasms as I did.

After a couple days of this, we talked, and both said we wanted to give an actual relationship a try. After all, hanging out most days and having sex most nights was so close to a relationship already, just without the commitment. However, it soon became clear that I was getting much more emotionally attracted to her than she was to me. At the time I thought I was falling in love with her, although once I fell in love for real with someone else a couple years later I realized that it hadn’t been quite all that serious. But I did, at least, feel quite serious about her, and she absolutely didn’t return the sentiment. I made a convenient boyfriend to her, but not one she felt terribly committed to. The relationship started to get a little bit strained as the end of summer approached and I knew I cared about keeping it going much more than she did. Then once I went back to school, the connection pretty much went away for her altogether, and while I wanted to try a long-distance relationship, it only took her a week to hang out with her ex and end up fucking him. I was badly hurt at the time, but I got over it – I realized that she wasn’t a bad person for doing that; we were just looking for different things, and I just had the bad luck to get more attached than she did.

In the end, we made awesome fuck-buddies, but a terrible couple. We didn’t talk anymore within a year, and I can’t say I missed her after how it ended. But now, with a bit of time and a better perspective, I’m able to look back and appreciate it for what it was – a summer fling with some really great sex. Lesson learned, though: you can’t base a solid relationship off of almost no common interests except a love of video games, punk music, and fucking. But then again, we were 18 and 19, and I’m pretty sure that age exists specifically for video games, punk music, and fucking, so we probably spent that summer doing exactly what we should have been doing.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My friends knew we were hooking up at this point, but I never told any of them the specific details of what happened for us in the bedroom (er, the living room…). I did talk about it in greater detail with my college friends who had no way of knowing her – I didn’t feel as guilty to tell them about it. There were a few moments that I had to tell them about – to this day, “just get up here and fuck me” and “I just want to feel you inside me for a minute” are two of the sexiest things anyone has ever said to me; I couldn’t keep that to myself.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Somewhat

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was incredible! Every time I think about the feeling of her vagina – still the tightest I have ever felt – I get totally aroused. And while fucking her breasts didn’t do a ton for me at the time, that stands out as one sexy memory as well, as I’ve never been with a woman again with breasts that substantial. This is a night of sex that I still think about from time to time when I’m horny.

What was the WORST thing about this hookup? Getting too emotionally attached and getting hurt by her. I wish I had kept the same casual mentality that she did, but it’s not in my nature, which historically has been as a bit of a hopeless romantic.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Just like our first hookup, it taught me that – with proper communication and both parties being able to try it without things getting dramatic – two friends helping each other out with their sexual desires and frustrations can be a wonderful thing. However, it also taught me that it’s very, very easy to get attached, and the danger of falling for a fuck-buddy is a very real one.

It also taught me the importance of communication as the number one key to making sex great. Without her open communication and helpful tips I might not have been able to make her come as well as I did, and without me feeling comfortable to talk to her, the whole premature-ejaculation part might have been a night-ruiner instead of an intermission break with much more, better sex that followed.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Somewhat negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? In theory, I love the idea of casual sex: we can’t all be fortunate in finding love, or finding that ideal partner, at any given time in our lives, and in some cases we’re just not ready to commit to a serious partner, and there’s no reason why we shouldn’t be able to have fun and enjoy our sex lives with understanding partners in the same situation. In concept, I think two friends, or even two relative strangers, deciding to help each other feel pleasure is a great thing, if the communication is strong so that the situation is understood and it can happen without anyone feeling hurt or emotionally left out. But that’s where it usually falls down for me: as much as I wanted a friend to have uncomplicated orgasms with when I was single, I’m a romantic deep down, and it’s hard for me to have sex with someone without developing deeper feelings for them, and at least wanting dates in addition to action. Both times I’ve consciously tried to have a friend with benefits, I wound up wanting more emotionally, and she wanted it to just stay causal, and my feelings were hurt in the process. It’s not their fault, of course; we just wound up needing different things from the pairing. But that is a recipe for drama. For people who can do it, adding benefits to a friendship can be a great thing, but I have never found that balance. Fortunately, now that I’m in a long-term relationship, I don’t think I’ll ever have to.

What I think needs to be changed is the bullshit misogynistic way in which society still acts like it’s more ok for a guy to want casual sex than a girl. Everybody struggles with loneliness and sexual frustration, and everybody just wants to get laid and feel good sometimes. Women have just as much right to want a friendly hand as a man, obviously, and it’s awful that women still sometimes get villified for wanting flings. We should be more free and more understanding about the different types of sexual partnerships people want – the real focus needs to be on communication and consent.

What do you think about the Casual Sex Project? I love it, on several levels. Since this is an anonymous forum, it gives people the freedom to reveal personal details and be totally honest about sexual desires and experiences in a way that we simply would not feel free to do if our faces or names were known. It’s a shame that our culture has such hang-ups about sex, but it’s great that this site creates a safe space to share honest experiences, tell our stories, and learn from other people’s stories. I’ve sure as hell never told this (or any) sex story is such detail elsewhere, and I found it so liberating to write it out. And I must admit, kinda hot to share something so intimate. Same goes for the stories I read from other people – hearing such honest personal stories can be both very enlightening and perspective-expanding, and very hot as well. This site is equally great for the mind and for the sex drive.

You have a hookup story to share? Submit it here!