An Unexpected – And Unprotected – Reunion

by Sean

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 fourth

An Unexpected – And Unprotected – Reunion

How long ago did this hookup happen? 12 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

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

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 a medium-height brunette with jet-black hair and pale white skin: a total emo-girl, flirting with goth. She had a pretty face, and a beautiful body: curvy but toned from working out, with gorgeous large breasts. She looked a bit like Sarah Silverman, if she was a teenager dressed for an Alkaline Trio show. She was 19 at this point, and I had just turned 20. For one hot summer between years of college she had been first my fuck-buddy, and then my girlfriend – I wrote about my first two major sexual adventures with her in my two “Summer Fuck-Buddy” stories. The relationship had ended very badly, as I got emotionally attached while she remained mostly just into the sex, and I got hurt when she broke it off very suddenly. But the sex had been great – she was a wonderful lover, and gave heavenly oral – and I can’t deny that I still jerked off thinking about her a lot. It was now most of a year later, I was done feeling hurt or bitter, and we were trying to remain friends. I still wasn’t sure if I really cared to be friends with her, after the nasty breakup, but every time I was home from college I kept finding myself hanging out with her. Maybe I was hoping for one more hookup, or maybe I actually hoped we could be friends, but either way, I feared it was a recipe for drama. Yet I couldn’t stay away when I was in town and she asked to hang out…

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was home for spring break, the school year after our summer fling. We were drifting apart, and only texted or talked occasionally – she wasn’t being exactly a great friend, and I was getting tired of putting up with it. But I was only home briefly, and I was feeling nostalgic, so when she asked to hang out I said yes. Things back at school were complicated: I was in the midst of a very drama-fueled period of hooking up with my (male) roommate, who had trouble even admitting to himself that he liked guys, and was thus very far away from wanting a relationship. He also had a girlfriend at a different college who had no idea he was sometimes having a bisexual fling with his roomie, and he was spending spring break with her, which only made me more anxious to take my mind off things by jumping right back into my old social life at home.

She called me and after some internal debate I went over to her house, to eat some Taco Bell and watch a movie. I honestly thought we were just hanging out as friends: at winter break when I had been home we had briefly made out, but otherwise kept things strictly platonic. She had a boyfriend at the time, though, and I didn’t know that they had broken up until we were hanging out (as I said, we didn’t talk much anymore). As a student herself, she lived at home, but it was late, and shortly after we started the movie her mom went to bed upstairs, leaving us alone in the living room. Sitting on the couch together watching the movie felt very natural – it felt a bit like old times. As the movie went on we started to cuddle up together, which again felt totally natural, and quite harmless at first. But as she cuddled closer, feeling her pressing against me started to bring back memories of how good it felt to have her pressed against me when we were having sex. I put my arm around her, and she snuggled in – I wondered if she was thinking the same thing. I tentatively placed a hand on her thigh, to see how she would respond. She made a little “mmmmm” sound – flirty, but not overtly sexual. I made an “mmmmm” sound back, and slid my hand a little deeper onto her inner thigh. She looked up at me, and smiled – and then I tentatively gave her a kiss. And she kissed me back, harder and more sexually, with tongue. Now we were making out, kissing deeply with our tongues intertwining. My hand finished sliding up her thigh, and playfully rubbed across the crotch of her jeans, which resulted in one more, more enthusiastic “mmmmm” sound. We left the movie on so her mom wouldn’t suspect anything if she heard – her mom would know something was happening if we went to her bedroom, and would come down and ask me to leave (she had knocked on the bedroom door to ask what was going on while we were mid-oral once before), so we had to stay here in the living room and hope she didn’t come downstairs. But we both knew exactly what we wanted.

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 kept making out for a while, exploring each other’s bodies with our hands. She still loved massaging my boner through my skinny jeans, and her large, curvy breasts still drove me wild. My luck with women hadn’t been great that year at school, and my luck with guys only slightly better. My one hookup had been my roommate: sex with him was really hot, and I loved his scrawny scene-kid physique, but it felt like it had been forever since I felt a woman’s soft curves in my hands (I love both, but at this point in my life when I wasn’t in a monogamous relationship I liked the variety), and her killer breasts offered a wonderful welcome back. Of course in the back of my mind I knew that hanging out with her had been a questionable enough idea, and sleeping with her again was a downright terrible idea that would probably lead to more drama, but in that moment I wanted her so bad that I frankly didn’t give a fuck, and I’m pretty sure she felt the same. As she caressed the erection still contained in my pants, my hand found its way back to her crotch, and she grinded herself against me with horny readiness, and breathed heavily.

I moved off the couch and knelt in front of her as I undid her pants and pulled them off, so she was sitting bottomless on the sofa. Her neatly trimmed but beautifully full bush of black hair stood out in stark contrast to her pale skin: even her pussy looked goth, and it turned me on so hard. She undid my pants as well, pulled them down, and I kicked them off. We were facing each other: me kneeling in front of her, her sitting on the low couch, with our faces and crotches perfectly level with one another. I started rubbing her clit, and she started giving me and hand-job. She was so wet, and the opening of her vagina welcomed my fingers in. I hadn’t brought a condom, because I definitely hadn’t expected this. As much as I really wanted us to have sex one more time, I was pretty sure this was to be an oral kind of night – which was still perfectly fine, since I really missed both the feeling of her blowjobs and the taste of her vagina. But she had another idea…

She scooted herself closer to the edge of the couch, bringing her vagina right up to the edge. Then she reached around my back with the hand she wasn’t stroking me with, and pulled me closer. With her hand-job hand, she guided my penis towards her, and slipped my tip between her wet, waiting labia. As the head of my penis slid into her, I first gasped with pleasure, then pulled back with alarm. “Condom!” I said. “I’m on birth control,” she said, “we don’t need one.” Holy shit, I thought – I’d never had unprotected sex with a woman before, and I had always wondered what that silky feeling of a woman’s vagina would feel like condomless. “Well in that case…” I said, and slid my dick towards her once again. Once again she guided it towards her waiting pussy, and this time I happily entered. I thrust forward and slid deep inside, as she pulled me close with that hand behind my back. It felt like heaven! She had an exceptionally tight pussy that felt super intense with a condom on; without one, the intensity was doubled. My nerve endings felt like they were on fire with pleasure, and every movement inside her felt incredible. I told her this, and she moaned and kissed me deeply, gyrating around my penis.

We fucked slowly, gently, passionately – me thrusting into her from my kneeling position in front of the couch, and her arching her waist to get the angle that felt best for her, holding me tight and kissing my neck to stop herself from moaning too loud. Her mom was, after all, asleep right above our heads, with merely a flight of stairs, a hallway, and no door standing between us and getting caught in the act. We moved with a rhythm that felt truly sensual, savoring every stroke of feeling our skin bare against each other for the first time. The feeling of sex with her felt so familiar and so good, yet the lack of a condom made it a whole new sensation. We kept going like that for about maybe ten minutes, though I had to slow the pace down from time to time as we went along, as I could feel my orgasm building. Soon, the feeling was becoming too intense to ignore. “I’m so close to coming…” I told her. “That’s ok,” she said, “just as long as you’ve got enough for round two. I’m not done yet!” “Oh, I’m good for at least round two,” I assured her – I always have enough cum for a couple rounds of sex, and I have always held strongly that one of the most sacred rules of sex is to never be selfish, and always make sure your partner has at least one orgasm.

I continued to slowly move myself within her for as long as I could, until the feeling got too powerful to hold back. “I’m going to come!” I whispered. Then, just to make sure we were on the same page, “in you?” “Yes!” She pulled me closer and arched against me harder, sliding me as deeply into herself as I could go – a motion that finished the job, as I felt her devastatingly tight pussy cover my every inch. I came so hard, and her fingernails dug into my back with pleasure as we both felt my orgasm fill her.

We held in that embrace for a while, making out as I remained in her post-orgasm. And then I asked her to lay back on the couch, and moved to go down on her. I kissed up her legs towards her crotch, as she happily laid back to relax and receive the oral. As I looked up at her vagina while I kissed towards it, I could see a bit of my cum dripping out of her onto her mom’s couch. “Shit, I think we’re gonna need to clean off the couch when we’re done,” I said. “That’s ok,” she said, “it won’t be the first time!” When she said that was the first time I had really stopped to think that of course I wasn’t the first guy to do it with her unprotected, I didn’t exactly know her sexual history since she’d been on the pill, and I wasn’t positive that this was safe, beyond the feeling that I trusted her to tell me if it wasn’t. I asked then (although I realize it was a little late by this point), “you are tested, right? You know this is safe?” “Yes,” she reassured me, “I got tested after the last time I hooked up with someone.” With that good news, I kept kissing up her inner thigh, until I reached her vagina, and began to slowly lick her clit and ease my tongue inside her.

She tasted as sweet as ever, though this time mixed with the salty taste of my cum. I certainly didn’t mind that taste, though, and I loved the sensation of pleasuring her orally again. She moaned with ecstasy, and reached down and placed a hand on the back of my head to pull me even closer. I ate her like that for what felt like forever, in the best way – bringing her to the edge of orgasm several times, but stopping just short; she said she didn’t want to come just yet. Her thighs closed tightly around my head, as we both took our time, giving and enjoying – god I had missed this. At one point I got her so close that she had to tell me to stop touching her for a minute altogether, and when I pulled my soaking face back I could see her vulva literally twitching with the muscle spasms of near-orgasm. When the close-call was over, she placed her hand on the back of my head and guided me back to licking her clit, but only for another minute. “I’m so close…” she said. “I want to come with you back in me. Are you ready?” Hell yeah I was! Watching her near-orgasm had me hard as a rock once again.

This whole time we had kept our shirts on, thinking that if we heard her mom getting out of bed above our heads we’d have time to scramble back into our pants and avoid getting caught. But as we prepared for sex round two, we both felt way too good to not be naked. We both tore off our shirts. After months of still thinking about her naked when I was masturbating away at college, it was wonderful to see her nude once again. She pulled some pillows and cushions off the couch onto the floor so we could lay down to have sex this time. We were pretty sure her mom was asleep for the night, but at this point, there was nothing we could do to avoid getting caught anyway, so we may as well make ourselves comfortable and have the sort of sex that we wanted to have. She laid down on her back and invited me to climb on top of her, sliding her mouth around my penis for one teasing lick as she got into position. Then I slowly guided myself into her once again.

We started out fucking slowly and sensually like before, as she wrapped her arms and legs around me. But I could hear from her moans and feel from her movements that she was still very close to coming, and I started speeding up my movements to increase the intensity even further. “Yes!” she whispered to me, and I moved still faster and harder in response. Her fingernails dug into my back, and she told me “I’m so close!” I knew that she generally didn’t come just from penetration alone, so I reached down with one hand and started to rub her clit while we kept fucking. It didn’t take much of that until she grabbed me hard, let out a moan that was probably a bit too loud for the circumstances, and came. Usually the feeling of a partner coming around me is enough to push me over the edge as well, but since her orgasm came so fast after we had started up again (yay, oral!), I held on – which is good, because she wasn’t done yet either. She flipped us over and got on top, and started riding me very fast. Her movements were almost frenzied – she was still in orgasmic mode, and wanted to roll that first orgasm into a few more. She went at it with such intensity, and soon reached down and started massaging her clit once again while she did it. Soon she made herself come again – really hard! And this time, the intensity was so strong that she brought me there with her, and I came inside her once again. Holy shit it was intense. Once both of our nice, long orgasms were finished, she collapsed on top of me, and we laid there cuddling, as an exhausted mess of sweat and cum in a pile of cushions on the living room floor.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Things went a bit better than expected after the hookup. We had both been on the same page about it being a one-time sexual reunion while I was in town, and there weren’t any tense feelings or moments of uncertainty about what it meant after we finished – we had had a great time together, and were both doing a pretty good job of not overthinking it. It made me feel a little bit worse about how apathetic a friend she was when I wasn’t in the room, and the hookup didn’t make her act like any better of a friend, but the drama that I had feared never occurred. It had been what we needed, and despite coming towards the end of a friendship that would continue to drift apart, it was a very positive experience. As I left at the end of the night (after helping to clean off the couch), we both clearly felt a bit better and more content than we had earlier that day.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, 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? I mentioned it to one of my good friends back at college, but that’s it.

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

Did you get emotionally hurt as a result of this hookup? A little bit

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? At a time when my love life was full of drama and stress, this provided some much-needed, very good and complication-free sex. Being able to experience one more round of sex with this wonderful former lover was great, and it was some of the best sex we ever had. Doing it unprotected for the first time also added a whole new dimension to it.

What was the WORST thing about this hookup? I had feared going in that it would cause some drama, and while it didn’t, it did add a bit more sting to her apathy as a friend. There was very little negative about it overall though.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? This was one of the most positive casual hookups I had had, and went more or less the way I think they should: two people helping each other to feel amazing in a safely drama-free situation. If more friends could have such great sex together without it being a big deal or changing the friendship too much, I think we’d all be much happier with our sex lives, and sex would be much less stigmatized!

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? While in this case my trust in her was well-founded, it’s generally a good idea to ask the STD question before you’ve had unprotected sex with someone, and not after… it’s just always good to be on the safe side!

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 casual sex can be a great thing – though it depends on the people involved. If partners are on the same page, and are open to taking care of each other’s and their own needs in a casual hookup without it having a negative aftermath, that’s great. People should feel more free to have the sorts of sex that they want without it being stigmatized, and people should be able to feel sexually fulfilled even if they’re not in a relationship. The biggest things to always take care of are clear, understood consent, and strong communication. It’s easy for people to get emotionally hurt in the intimacy that even casual sex entails, so you need to talk and know exactly how you both feel and what you both want before entering any situation.

What do you think about the Casual Sex Project? I love it! It provides a wonderful opportunity for people to talk candidly and honestly about their sexual experiences and desires in a way that we just can’t in our society where sex is still as stigmatized as it is. It’s so great to read other people’s stories, to see how others experience sexuality – it’s both very enlightening and very arousing! And it’s incredibly liberating to be able to write so frankly and openly about it. I sometimes wonder if I’m going into more detail than the mission of this site was made for, leaning too far away from straight-up study and into the realm of writing erotica, but exploring both of these sides of my stories is equally liberating. And frankly, it’s a pretty good exercise as a writer to try and capture the honest sexual experiences and the erotic feelings they inspire in my story.

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