What’s your gender? Man
How old are you? 33
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? 5
Visit With a College Friend Turns Sexy
How long ago did this hookup happen? 8 years ago
What was your relationship status at the time? Single
How would you best classify this hookup? Friends-with-benefits
How long did you know the person before this hookup? For more than 3 years
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’s my best friend, since college. A part punk, part nerd, really fun woman, with a petite build, pale complexion with freckles, a very pretty face, and dark hair (though at the time of this story bleached and dyed red). We had been strictly platonic friends for a couple years until during our Junior year at school in Chicago we had both had a pretty frustrating dry spell in the dating and sex departments, and she had suggested helping each other to ease the frustration with strictly casual and friendly, uncomplicated sex. Thanks to good communication and a very open, trusting friendship, the arrangement worked really well, and for the last two years of college, when we were both single, we would continue to occasionally sleep together while making sure that the sex never dominated or overshadowed our friendship. Although the first time one of us started dating someone it was a little tricky and awkward to re-establish boundaries, it was all good after that, and we remained once-again-platonic best friends when one or both of us were dating other people. After college, we stayed in touch, and one of us tried to visit the other every summer after I moved to Seattle and she moved to LA. After college, we both started dating other people once we were both established in our new home cities, and so for the first three years or so after graduation our visits to see each other were strictly in platonic friend mode. But somewhere after that, between times when we saw each other, my boyfriend and I broke up, and she and her boyfriend broke up. I was single, but she was dating a new guy she had met more recently. She came to visit me that summer, as per usual, and I assumed that things would remain in just-friend mode. In fact, since it had been four years since we’d last had sex, I figured that side of our friendship was done with for good. It didn’t quite turn out that way.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The first couple days of her stay were totally in just-friends mode; old friends hanging out, catching up, doing all the things we liked to do, like digging through used record stores and playing video games from the 90s. Since I shared an apartment with two roommates, as per usual I let her sleep in my bed, and I stayed in a sleeping bag on the floor. Sure, we knew each other’s bodies very well, but sleeping in the same bed would blur that line between friends and lovers in a way that we knew wouldn’t be ok given that she had a boyfriend she’d been dating for a couple months. But on the third night, she was in town, she woke me up in the night. “Hey, Sean?” I asked her what was up, from my spot on the floor. “I’m really horny… I know it’s been a few years, but would you want to help a girl out again?” I propped myself up to look at her in the bed. “…but you have a boyfriend.” “He’s not that serious. We’ve only been dating a couple months and I’m not too attached or anything. And he doesn’t really know what I like. I was laying here thinking about the sex we used to have back in college, and it got me really wanting that again.” I hesitated. I was totally game, but cheating on a partner had always been totally off limits for us. “You’re sure you’re cool with cheating on him with me? That’s not going to make things weird?” “I’m sure.” I paused again and realized that since I hadn’t expected this to happen, I wasn’t prepared. “I don’t have any condoms – I didn’t think we’d be doing this!” She smiled at me and reminded me that when she’d been dating her previous boyfriend for the better part of three years, she got an IUD after they’d had a condom-breaking scare, and had been sticking with that method. She asked me if I’m tested, or if I know for sure that I’m clean. I did – and she told me that she did too. “Ok, get up here into bed,” she told me.
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? I got up and pulled back the covers to join her under them. When I did, I saw that her pajama bottoms were already off under the blankets, and her labia and the first two fingers on her right hand were visibly wet – she had already been masturbating before she even woke me up. She giggled as she saw the smile that was spreading across my face. She pulled off her shirt, and I stripped off my pajamas, revealing that I was already starting to get a little bit hard. Yes, she’s my best friend, but seeing her naked again was seriously a sight for sore eyes. I climbed into bed with her, and we kissed on the lips for the first time in four years.
Even after all that time, there was no awkwardness – we very quickly got down to business with some very heavy, deep kissing, and our hands started exploring each other’s bodies. “We should be quiet – we probably don’t want my roommates to know we’re having sex, yeah?” “Yes, absolutely,” she said. We made out and fingered/hand-jobbed each other for a couple minutes, and then I asked her, “what exactly was it that you were missing so much?” She responded with her characteristic frankness: “how well you know how to eat my pussy.” Over the time in college when more of our Saturday night hangouts ended in fucking than didn’t, she had helped me to figure out exactly how she likes to be eaten out so that she always came. I was nervous I’d be a little rusty – both with her pussy and with cunnilingus in general, considering that I had spent much of the last three years sucking my boyfriend’s dick instead – but it came back to me quickly. I kissed my way down her neck, across her small but very nice tits, and down her pale white stomach until I got to her trimmed-but-bushy crotch. But I didn’t want to dive right in just yet: first I moved all the way towards her feet, and slowly kissed my way up her legs, to tease her. “You fucking tease!” she whispered jokingly. I smiled, and when I got there I delayed the moment further by licking all around her inner thighs and crotch before finally tracing my tongue across her labia and sticking the tip of my tongue into the opening of her vagina. She tasted just as good as I remembered, and I tongued her there for a while before moving back up towards her clit and pleasuring her that way too. Following the cues of her body language, I switched back and forth between those positions for a while, before she reached down and grasped the back of my head and pulled it closer to her crotch – her sign that her orgasm was imminent. As I licked her clit faster, I took one finger and slid it slowly into her vagina – and pow, she started to come around my finger, turning her head and burying her face in her pillow to quiet the moans.
I licked her until the aftershocks of her orgasm were complete, but her body language was definitely not that of someone settling down after the fun is done. “Oh shit yeah,” she said, “now get up here and let’s fuck.” She didn’t have to tell me twice – my erection was throbbing from the pleasure of going down on her. I moved upwards and rubbed the tip of my penis across her soaking wet inner thighs. She definitely seemed ready, but just one more time, in the interest of being a good friend, I asked, “you’re sure you’re ok with this?” “Absolutely,” she said, “and besides, we’re in the middle of it now, I’m pretty sure what we just did is already cheating, even if we stopped now.” She smiled, and added, “and besides, I’ve never cheated before – it’s kinda fun how naughty this is! Especially since I’m really not serious about this guy.” “Yeah, this is fun!” I had to agree. And then I reached down with one hand, guided my dick to the opening of her vagina, and slid myself inside – feeling her unprotected around me for the first time.
She felt so good: the soaking wetness of her vagina after all that oral felt incredible. “Oh fuck,” she moaned, closed her eyes, and kissed me. Partly in the interest of quietness and partly because it was just what felt right, we fucked very slowly and passionately, and she wrapped her arms and legs around me to pull me closer in. I felt her nails dig into my back, and she moaned her pleasure into my ear and licked it. We kept going like this for quite a while, and eventually, I could feel the muscles of her vagina start to tighten as her heavy breathing accelerated and it was clear that she was approaching orgasm number two. This felt SO good – it was a fuck for the ages as if we were trying to make up for not having had sex in four years. But with how good it felt, I knew there was no way I could feel her orgasm without coming too, so I had to softly interrupt the moment to ask, “Where do you want me to come? That’s one boundary we’ve never had to discuss before.” “Right where you are!” She replied. That’s what I was hoping she’d say – I really wanted to know the feeling of coming in her. “Sounds amazing!” I continued my slow motions within her, getting a little bit more intense as we were both clearly approaching climax. She dug her nails in deeper into my back. And then, with a moan she tried to keep as quiet as possible, she came, and when she came, I came inside her.
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 stayed in our embrace for a bit as the wave of orgasmic pleasure stayed over us, and then we cuddled up in the bed. I asked if I should stay there with her, or go back to my sleeping bag, and she told me to please say. The next morning when we woke up together, we laid there and talked for a bit. She at first felt guilty to have cheated on her boyfriend, but the guilt subsided when she realized that her willingness to prioritize pleasure in the moment over faithfulness to him meant that she really wasn’t feeling anything serious about him at all. After all, they had only been together for a couple months, and after the initial fun of the relationship was starting to wear off she wasn’t so sure how she felt about a long-term commitment with him. She said that maybe having the temptation to go back to our friendly-sex ways was exactly the test she needed to see if he was really boyfriend material or if she should move along. The verdict was definitely that she was going to move things along. I told her I was glad I could help, and I asked her if the previous night had scratched the itch she’d been having. Mostly, she replied.
We soon wound up kissing again, and once again getting very excited. Soon she climbed on top of me and we had some quick morning sex before we got out of bed. Both of my roommates had gone to work by this time, so she did it fast and hard since she didn’t need to worry about too much noise, and massaged her clit until she brought us to a loud mutual orgasm. The rest of the week was great: doing all the stuff we loved to do as friends by day, and then having sex every night and sharing the bed for the remainder of her stay. After all, we probably weren’t going to see each other again until our annual visit the next summer, so we wanted to stock up while we could! She broke up with her boyfriend when she got back, not surprisingly. By that next summer I once again had a girlfriend and she once again had a boyfriend, and we’re both still with those people, so that visit wound up being the last time we added such benefits to our friendship, but it was a great week of sex to send off that part of our friendship with. We remain best friends to this day, though, and I was in her wedding party when she and her now-husband got married. He doesn’t know that she and I ever used to sleep together (nor does my girlfriend), and it’s probably best that we keep it that way, to avoid any drama or complicated feelings from our partners. That’s part of why it’s so great and so cathartic to be able to write about it on here though!
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) IUD (Intrauterine device), Discussed STI testing history
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? No one – it stayed just between us.
How would you best summarize people’s reactions about this hookup? I didn’t tell anyone
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? Amazing, unprotected sex with a very communicative and fun partner, who also happens to be my best friend!
What was the WORST thing about this hookup? The initial guilt of cheating.
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No – though it continued my positive feelings that our previous hookups had instilled in me.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all 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? I think more people should be open to exploring it, as it can be a really great thing for people. But with that said, communication is even more important than with in-a-relationship sex, and both partners have to be on the same page to help things go well.
What do you think about the Casual Sex Project? I love it! Both as a way to read about other people’s experiences and to share my own in a way that I wouldn’t except in an anonymous forum. It is stimulating to both the mind and elsewhere. 😉
You have a hookup story to share? Submit it here!