Summer Fuck-Buddy: The First Night



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 first

Summer Fuck-Buddy: The First Night

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? Fuck-buddies / Booty call

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, just a few months younger than me. A brunette of medium-tall height, with long, wavy, black hair and pale white skin. Her face was cute, although it wasn’t until she made the first move that the attraction occurred and I started to think of her as sexy or beautiful. Her body was fucking incredible, though: she was very curvy, with huge, gorgeous breasts, and worked out and had a great physique. I had noticed this, of course, but didn’t feel particularly attracted to her at first, until she caught my attention with some heavy-duty flirting that soon turned to outright seduction.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was the summer after my Freshman year of College. I had just lost my virginity that year, but the attempt at a relationship that followed the hookup didn’t work out very well, and ended in a rough rejection in which she hurt me very badly. I was very sexually frustrated, and really wanted to find someone to have more sex with that summer, female or male. This girl started hanging around my group of friends through a mutual friend, and while I cannot deny that her incredible breasts caught my eye right away, the attraction just wasn’t there – for me at least. It was there for her, and fortunately she decided to do something about it. It didn’t take me too long to come around, when she came to the FYE where I was working for the summer in a decidedly short skirt and cleavagey top, and started really flirting. She called me over to a far corner of the store to ask about some CDs there, and while we were there she started stroking her leg, and said to me, “I just shaved my legs – I can’t believe how smooth they feel! Feel this – isn’t that a great feeling?” I was hesitant at first, but as a horny 19 year old I was not about to turn down an outright invitation to feel this woman’s very nice-looking legs, even if I hadn’t been terribly attracted to her up until then. Yes, they did feel great – and that feeling got me thinking, and maybe a little bit hard. She asked when I was getting off work, and then asked if I wanted to come over and play some video games after I got off. She was clearly inviting me to fool around – it started an internal debate in my head: I hadn’t really felt attracted to her until that moment, so was I a terrible or shallow person to so quickly go from not feeling attracted to going to her place to fuck after work? I started to say that I wasn’t sure, but one more “please?” from her – and another look at the wonderfully toned and curvy legs I had just felt – and I said yes. It wasn’t like me to do so, but I figured that if she wanted a friend to get off with, and I wanted the same thing, why not give it a try? I picked some condoms up on the way, just in case. It turned out I didn’t need them that night – in my horny thoughts I had slightly overestimated how fast things would move – but it’s better to be safe than sorry, and what happened was just as wonderful. We both knew that something would happen that night that would feel really good, but the specifics felt very spontaneous – we were both totally in the moment, figuring out just what we wanted from a friendly hookup.

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? We went through the motions of playing video games for maybe ten minutes, but soon things turned to making out, intensely. I started feeling her up – oh my god, those huge tits felt so incredible to my 19-year-old self – and gradually my hand crept down to those smooth legs, and up her skirt. As I pulled her underwear aside, I felt two things: she had a clean-shaven crotch (I generally prefer women with pubic hair, but it was a very pleasantly silky sensation all the same), and her vagina was starting to get quite wet. When I touched it, she stopped me – she said she didn’t want to move that fast, and she didn’t think she wanted to actually have sex tonight; it was just too soon into knowing me for her to feel comfortable going full-on fuck-buddies, but let’s take things slower and see how the night goes. I understood, of course – I had only done this sort of thing once myself, and it was generally outside my comfort zone. We returned to making out – kissing this girl (who I had now decided was definitely very hot) and massaging her toned physique and those incredible tits was more than enough for me.

But as we continued, she started rubbing her crotch against mine progressively harder and harder, and starting breathing heavier and heavier. She was so turned on – she clearly had been just as frustrated as me, and needed this just as much as I did. I slowly massaged my way down her body, until I was down there again, but this time I stayed outside her underwear, not wanting to move too fast. She loved it – I could feel her react with such enjoyment as I massaged her clit though her panties, and I could feel her wetness absolutely soaking though them. Then she gasped something that was incredible – and very self-confidence boosting – to hear as a teenager and pretty inexperienced lover: “oh my god, you’re driving me wild!” When she said that, I tentatively started to pull her panties aside once again. “Yes!” she said – and I slid my finger inside, then a second finger. She closed her eyes, and opened her mouth into an ecstatic look of pleasure. I continued to finger her slowly and deeply, while rubbing her clit with my thumb. I slowly moved down below her waist, pulling off her underwear but leaving her skirt on, admiring her beautiful vagina as I continued to pleasure her. I moved my face in towards it, and started to lick her clit while I kept fingering her. She moaned at the first lick, and placed one hand behind my head to push my face closer to her pussy. Her juices tasted very sweet. It wasn’t too long before she came around my fingers. She relaxed into a deeply-satisfied state, and I cuddled with her. A few minutes later she picked the video game controller back up, and we resumed playing. At that point, I thought the night’s sexual activities were over – and that was fine with me. Being able to go down on her and make her come like that was very satisfying for me as well, as giving oral has always been one of my favorite parts of sex.

But then as we were playing games, she asked – totally casually and unexpectedly – “how big is your penis?” I was totally taken aback by how out of nowhere the question came. I told her the standard six-ish inches long. She responded by asking how big around it was. I told her pretty thick, I guess, but that to get a good idea of that she’d just have to see it. She asked me to show her – and I said ok, of course, but would she maybe give me a hand getting hard? She smiled, and started rubbing my crotch through my jeans until I was obviously very hard indeed. I took it out for her. I couldn’t believe how the night was going. I had thought we were done, and I was perfectly happy to play a bit of post-cunnilingus Sega and go home, but now I found myself with my boner out, stroking it for her so she could get her desired demonstration of what I look like at full hardness. I had no idea what may or may not happen from here, but this was the first time I had masturbated in front of a woman, and it was pretty hot – especially since I knew her juices were still on my hand from fingering her, and I was now rubbing them on me. Feeling good, and feeling bold, I asked her if she wanted to try it out. She coyly said “no, you can put it away for now. I know where to find it if I need it – I was just curious what it looked like.” I smiled – her coy manner turned me on, and I had a feeling that she had something in mind. She picked her controller back up, and started another level, but kept coyly smiling, and reaching over and gently hand-jobbing me through my jeans. Then in the middle of a level maybe ten minutes later, she abruptly paused the game, and unzipped my pants.

Her tease had kept me totally hard that whole time, with the occasional quick stroke between Sonic levels, so when she undid my jeans and pulled my dick out, it was throbbing. No one had touched my penis but me in a good seven or eight months, and it was very appreciative. She gently stroked it, expertly sliding her hand along my shaft and caressing the tip with her fingers. Then as she continued to stroke, she asked me if I had ever gotten a blowjob before – and I confessed that I hadn’t. She gave it just a moment’s thought and a sly smile, and before I knew it I was getting my first blowjob. She knew what she was doing, too, and her experience was a huge turn-on: she sucked me so incredibly, swirling her tongue around the tip of my penis, licking tenderly up and down the shaft, and occasionally taking me really deep. This was one hell of a first blowjob – it would be several years before I would be with another woman who gave oral as magnificent as hers. While she was going down on me, I started once again stroking her body, and feeling those incredible tits. Feeling this, she paused for a moment, sat up, and at last took her shirt off. Between her physique and those breasts, she looked fantastic topless. When I told her this, her response was half a sincere thank you, and half a coy “I know.” As she resumed the blowjob with even greater enthusiasm, I continued to massage her everywhere, slowly moving from her breasts back to her crotch, reaching behind her (she was kneeling next to me on the bed) to feel that once again her vagina was very wet, and asking for my fingers to enter. Between the warm slippery feeling of fingering her and the even more enthusiastic licking and sucking on me that it inspired, I soon felt my orgasm building. I told her that I felt very close to coming, and asked where she would like me to cum – should I have a tissue to cum into? She just looked up at me with that coy smile once again and said no, she had it under control, and locked her lips around me. The thought of orgasming against her tongue and filling her mouth was incredibly hot, since I had always wondered what it would feel like; so hot that it quickly pushed me over the edge, and my whole body shook with the orgasm. She made an “mmmm” sound as I came in her mouth – came so much that a bit of cum escaped her lips and tricked down her hand that was still stroking me. When my orgasm was done, she sat up and swallowed her mouthful of cum, and I licked her hand clean (I’m bisexual, so I have no problem tasting cum, even if I hadn’t had the pleasure of tasting another guy’s yet at this point). We then laid down on the bed together, and I continued fingering her to a second orgasm, while basking in the glory of my first blowjob experience.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? We kissed passionately before she eventually said I had to leave – her dad was asleep down the hall, after all, and she didn’t want him to wake up and see that I was still in her room. When we kissed, tasting my cum on her tongue was incredibly hot, and it was a reminder of how sexy the situation had been. I asked her what this made us – fuck-buddies, or a possible relationship. She said we’ll see – but in the mean time, let’s hang out and do this again soon. I eagerly agreed. We hung out a few days later – and that time, I did get to use those condoms that I had bought. But that first experience of sex with this fuck-buddy was so great in itself that I think I’ll write another story about it… suffice to say, we both came a whole lot that summer.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, I was feeling lonely, It was easy / convenient

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? No one for a little bit, since I’ve never been one to tell sex stories about people – I think it’s really not ok to tell hook-up stories to people who know the other person unless they specifically say it’s ok to tell. However, soon our dynamic became obvious to the group, as we didn’t try to hide it and were very close and a bit physical when we were all hanging out. At that point, when friends asked me if we’d hooked up, I said yes, but left it at that. It was only much later that I confided in them what a fantastic giver of blowjobs she was. As I went back to school and she needed to find someone else to fulfill her sexual needs, at least one of my other friends got to experience her great oral skills, but at that point I was happy for them rather than jealous. I told my best friend at college about the fling, but she didn’t know her, as I went to school out of state, so I didn’t feel guilty about sharing. And this was my best friend – the two of us talked about everything, especially comparing notes on our sexual adventures and frustrations.

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

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

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? For a 19-year-old (fuck, for anyone), what’s not amazing about ending a long day at work with some totally unexpected and totally amazing mutual oral sex with a fun partner?

What was the WORST thing about this hookup? Nothing. We continued hooking up, and eventually some drama was caused, in the expected way – one of us developed romantic feelings (I did) that the other one (her) did not return. But the hookup itself was exactly what we needed, and even if I got too close and and wound up getting hurt by her more consistently casual attitude about the whole thing, I don’t regret a thing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? At the time, it was just what we both needed – an equally horny and willing friend to help each other out of our frustration. It’s a shame that it wound up getting a bit more dramatic, but that happened later. This hookup taught me that if you and a friend both really need someone to go down on you, and you’re open to trying a little friendly action even if you hadn’t necessarily thought of doing it before, what the hell, you might as well try it – assuming the communication is good and you can do it without it getting awkward.

This hookup also continued the feeling I had started to have already that giving oral sex is one of my favorite things to do. Whether it’s with a woman or a man, I love the intimacy and the satisfaction of using my mouth to make someone feel that good. There’s no other feeling in the world like someone cumming against your tongue. It also taught me that, with the right partner who is just as into oral as I am, receiving a blowjob is every bit as amazing as intercourse. It makes me frustrated when anyone treats that as foreplay only – sometimes that should be the main event itself (mutually, of course, so no one feels left out!).

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? In hindsight, having unprotected sexual contact with someone who I knew so little was probably rather dangerous. Since it was all oral there was obviously no risk of pregnancy, but in terms of potential STD risk it was a stupid thing to do, with the swallowing of fluids involved. It turned out ok, of course – we were both fairly inexperienced, and definitely both clean, but remember, people – safe sex!

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!