What’s your gender? Man
How old are you? 39
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Ontario, Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Insurance
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0
Last Time With An Amazing Finish
How long ago did this hookup happen? 2004
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 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? My partner was pretty much my ex-girlfriend at the time. She was 24, 5’8″ and around 130 lbs. She had an absolutely beautiful face and the most stunning eyes I’ve ever seen, nice b-cup breasts and a shapely round butt. Very much the girl next door type. We were the same age and had met in the first year of university and had been a couple through our entire time there. After graduation, our relationship began to fall apart slowly over time. After a few months it was clear to both of us we were growing apart so we had a conversation where she told me she thought our relationship was ending and ‘maybe it was time for us to break up’. I was in denial but it was clear that was the end. We continued to hang out regularly as friends, but hadn’t told anyone that we were basically broken up. I was confused at the time but still in love with her.
At that point, sex had ceased. We always had a healthy sex life but in retrospect, it was a bit vanilla. She could occasionally be a bit wild (public sex, secret handjobs in public, blowing me while driving) but usually it was straight sex in bed. She had, to this day, the tightest pussy I’ve ever fucked, she felt absolutely amazing and I’ve never felt anything like it again, just a vice grip on your cock. Like most long-term couples we had long since stopped using condoms (her on the pill), but for whatever reason, I had never come inside of her. I was always too afraid of pregnancy so I’d always pull out and shoot on her breasts, ass, and occasionally in her mouth.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? That day we went to a baseball game with friends. It was an awkward day, our friends were beginning to understand that something might be wrong with us, and we were still trying to figure out what we were, both of us still in a bit of denial. I remember I drove her back to her place at the end of the day (afternoon game). As we got to her place a huge thunderstorm started so she invited me in and said I could stay if I wanted so I didn’t have to drive home in the storm. We sat on her couch talking and watching the rain, eventually getting closer and closer.
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 don’t remember who started it but we eventually ended up making out on the couch. At this point it had been a couple of months since we last had sex so there was that incredible sense of longing. My hands moved to her breasts quickly, playing with them through her tank top, her hand reaching between my legs rubbing my already fully erect cock. We quickly moved to her bedroom and the clothes began coming off. I pulled off her tank top and began playing with her breasts through her bra, then pushed her breasts out of the bra and began sucking her nipples. She had incredible large nipples that got extremely erect when she was turned on.
I pulled her pants and underwear off and laid her down on the bed and moved down to her sweet spot, massaging around her inner thighs with my fingers before slowly massaging her pussy with my tongue. I could feel her juices in my mouth right away and it was obvious how turned on she was as she moaned and writhed with pleasure. After a few minutes, she pulled me up began to go to work on my penis, her warm and wet mouth making beautiful suckling and slurping noises as she worked up and down my shaft. She crawled up on me and whispered, “Why don’t you get on top of me.” She rolled onto her back and spread her legs, I climbed on top and she immediately grabbed my shaft and guided it to her opening.
Because of how tight she was it sometimes required a bit of finesse to penetrate her initially but on this night I slid right in. It felt incredible, the combination of the weird feelings between us and the amount of time between our last encounter made the sex extremely hot. Her pussy was gripping me just right and very quickly I was having trouble holding on. After about ten minutes rhythmically thrusting into her, slowing down at points to prevent myself cumming, she rolled over and mounted me in the cowgirl position.
Cowgirl was probably the favorite position for both of us, she loved the control and I loved the way she felt when she ground her incredibly tight pussy on my shaft. She sat up on me and slowly started bouncing up and down, I watched my cock disappear inside of her while I played with her breasts and sucked her nipples. She slowly picked up the pace, then suddenly stopped and pushed me deep inside and began to slowly grind my cock. She picked up the speed and it was the best feeling in the world, hitting all the right spots. She leaned forward and grabbed my wrists with her hands and put them above my head so there was no way I could pull out, I was almost there. At that point, I warned her I was going to cum. She raised herself up so just the tip of my cock was inside as I let loose with my first volley of sperm, she then sat down putting my shaft deep and started grinding even harder. I pumped my entire load inside of her as she milked my balls empty. It was easily the most intense orgasm I’ve ever had, as she forced me to shoot spurt after spurt deep into her. I came so hard my balls were sore when it was over, and she gave me a memory I’ll never forget.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, one
Did your partner have an orgasm? I don’t know
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? I woke up before her the next morning and lay in bed next to her, rubbing her back hoping I could maybe get another turn. When she woke up, she said she had to go to work and said I could grab some breakfast out of her fridge before I headed home.
A few weeks later we had another talk where things were ended for good. We never spoke about that one last hookup after it happened. After that, we hung out less and less until I found another girl (my now partner, mother of my children) and eventually we lost touch completely.
Although it’s been many years I still think about this encounter fairly regularly and still masturbate thinking about it from time to time. It was the first time I’d ever com in a girl bareback and it happened to be the last time I had sex with that girlfriend with her pretty much forcing me to cum in her, making it way hotter than I could’ve imagined. I still remember the intensity of that orgasm and the combination of complete sexual satisfaction and a bit of soreness when it was over. I don’t wish to be back in that relationship (as I said we weren’t right for each other by that point) but I do wonder what one more time with her would feel like, how she would feel, etc.
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, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, I was feeling lonely, Just happened, I don’t know why just went along with it
How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it
What substances did you consume? Alcohol
How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it
What substances did your partner(s) consume? Alcohol
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’ve mentioned to one buddy who thought it was extremely hot that she made me cum in her our last time in bed.
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? I don’t know / I’m not sure
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? It was one last time with a girl I was (and still am) incredibly physically attracted to. Having her force me to cum inside of her was outrageously sexy and I’ve never felt anything like it again. I have no desire to have a relationship with her as I’m extremely happy with my partner now, but I still occasionally think about that night
What was the WORST thing about this hookup? I wish it had happened again, I would’ve loved to have another round with her!
Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really, we were two people in a weird place, I was inexperienced with breakups and emotional and just wanted to feel close to her again, as well as deeply lusted after her all at once, it was an interesting combination of emotions that lead to incredibly intense sex
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? Not really, I think I covered most of it
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? Sex is sex, people should do what they like and no one should feel shame for doing anything sexual. Sex is fun and natural, as long as all parties are consenting and people don’t get hurt I see nothing wrong with it.
What do you think about the Casual Sex Project? Great place, love reading stories, finally got around to sharing one of my own
You have a hookup story to share? Submit it here!