What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Some college (not currently in college)
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How long ago did this hookup happen? 6 months
What was your relationship status at the time? Same as current status
How would you best classify this hookup? One-night stand
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 is the same age as me (29), 5’5″ 125lbs, hazel eyes and dyed reddish brown hair, small perky A-cups, the most amazingly firm round ass. Even though she is a mom, she is easily one of the tightest fittest bodies I have ever seen. She has a tramp stamp on her lower back and some song lyrics on her left rib cage. I’ve known her for 15 years give or take but she was always very shy and a tomboy. She’s never really had any real boyfriends that I’ve known of, however, when she was 19 she had a drunken hook up with a guy she was kind of seeing and wound up getting knocked up, they had the kid and shortly after she was single. In our early 20s, we became pretty close. She was very friendly and flirty but things never escalated as she would always pull away and get distant, eventually, I got tired of the games and moved on. Her BFF eventually got married to one of my friends and that was when I started to learn things about her. One night when we were about 27, the topic of birth control came up or something and the BFF mentioned that this woman had been on the pill since just after she had her kid yet she rarely ever had sex. She had only been with three guys and only had sex a few times a year with one of her guy friends. She was asexual or something and that’s when a lot of stuff started to make sense, from what the BFF said it was not like she was against sex but it didn’t really do much for her and she’d usually just get herself off if she needed a release. She was attractive and all but the lack of sex meant I saw zero future worth pursuing.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?
It was a Friday night and we were going to a friends birthday. It was nothing big just dinner and drinks at the local pub. She dropped her kid off at her sister’s for the night and came by my place to hang out before the pub. She had a way of making a simple pair of jeans and a t-shirt look incredibly hot. We had a couple of drinks before calling a cab and headed out for the night. It was nothing out of the ordinary. We had dinner and started putting back some drinks. She wasn’t much of a drinker and before we knew it, it was already midnight. We were pretty drunk and called a cab.
We got back to my place and I asked the driver how much more it would be to her place. But at some point, she stopped me and asked if she could just crash on my couch so she didn’t need to get a ride back for her car in the morning. I said ok and we went inside. We weren’t really ready for bed and decided to watch a movie. Before settling down she asked for a pair of PJs or sweatpants so she could get out of the jeans. I gave her a pair and she went to change and then came back and snuggled up to me on the couch. She picked the movie [some chick flick] and we killed the lights. It wasn’t long into the movie and the scenes were getting increasingly sexual. It had been years since I had even thought about her sexually but being drunk and cuddled up with her watching this movie, I found myself becoming increasingly horny. The way she was laying against me provided me with a good angle to rub her back. I started out over her shirt for a while as she purred seemingly enjoying it then I stopped at which point she asked me to continue. I did and after a few minutes casually slipped my hand under the shirt and continued rubbing, she showed no sign of objection so I continued. I slowly pushed further down her back with each stroke until I was at the waistband of the sweatpants. I slowly slid my fingers under then over the thin sideband of a thong. She shivered a little as my hand made its way over and caressed the curve of her firm ass cheek. I rubbed her butt for a while then stopped. A few minutes after stopping she sat up and asked why I stopped, I shrugged my shoulders and said I didn’t know but asked if she liked it. She shyly smiled but didn’t respond. I asked if she was going to answer and she didn’t say anything then placed a hand on my thigh and just stared at me. We looked at each other in the glow of the TV. I finally went for it leaning in and kissed her. She kissed back and her hand started to slowly move up my thigh. I ran a hand up the back of her shirt and pulled her close as we made out like high school kids. She crawled onto my lap and I got harder by the second. She pulled my shirt off and I did the same to hers, revealing a simple black bra that cupped her firm little tits. I unclipped it and pulled it off, exposing her hard little nipples. I kissed down her neck and sucked on her nipples as she moaned, then she pulled me back up and asked softly: “Please tell me you have condoms.” I nodded my head and she got up and told me to get them. I went over to the end table where I kept a few for these occasions and I pulled them out. Then she told me to stand up and drop my pants first. I happily complied and dropped my jeans and boxers, my erection springing up her eyes went wide and she gasped and blurted out “WOW! holy crap!” I just laughed a little, knowing what I knew about her lack of sexual experience and her reaction and it was safe to assume I was the biggest she’d ever seen. I asked if she wanted to stop, but she just shook her head unable to look away. I told her it was her turn and she pushed the sweats down then turned and slowly peeled the thong down.
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 were both completely naked now and I could tell she probably needed a bit more warming up so I laid her down and got between her legs and told her to relax and go with it. She was shaved and had nice tucked in lips. I began to lick her pussy and she jumped a little. It didn’t take long to get her juices flowing and her hips bucking. She was incredibly wet so I asked if she was ready and she nodded yes. I slipped a condom on, lined up and pushed in slowly. I couldn’t believe how tight she was. It took a few minutes to get myself all the way in and for her to get comfortable then we started fucking in missionary but she couldn’t handle the deeper strokes so we switched to her on top. We went at it in cowgirl for a while. It was working for her but her pace was too slow for me so we switched it up. She had loosened up a bit so I took her in doggy. Her ass looked better than I could have imaged as I pounded her hard and deep. I could tell I was pushing her limits but I was super close so I grabbed her hips and started speed fucking her but it was too much and she stopped me, with my balls throbbing on the edge of release. I reluctantly pulled out and we returned to cowgirl and she started riding me again. Her pace was a little quicker and harder and I could feel myself building up again. She was so wet and it felt amazing. She was building up to her own orgasm and she was on a mission to get there as she was grinding and bucking on my cock. That was when it occurred to me in my drunken state that things were feeling a little too good and wet. I was certain the condom had broken and tried to stop her but she wasn’t stopping until she got her orgasm, and she got it. She started to moan and twitch and buck uncontrollably. Her walls trembled as her pussy squeezed me with a death grip and that was more than I could handle. I thrust into her and my cock swelled and unloaded inside of her. We both sat there speechless for what seemed like forever. Then the movie ended and we turned on the lights and that was when my suspicions were confirmed. The condom was bunched up at the base of my cock. We both sat there waiting for the other to say something; then finally she said, “Well, the good news is I’m on the pill.” We both laughed a little and talked and went to bed.
How sexually satisfying was this hookup? Very
Did you have an orgasm? Yes, 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? We woke up the next day naked in bed and well aware of the previous night’s events. We discussed it and she was clear she wasn’t interested in any sort of relationship and how she was barely sexually active. She actually hadn’t had sex in about 9 months. We had breakfast and she left. I don’t have any expectations at all. If the opportunity presents itself, I’d take it but that’s about it.
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Birth control pill / patch / ring / injection / implant
What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication
How intoxicated were you? Drunk/high but not wasted
What substances did you consume? Alcohol
How intoxicated was your partner? Drunk/high but not wasted
What substances did your partner(s) consume? Alcohol
How wanted was this hookup for you at the time? Somewhat
Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’
How wanted was this hookup for your partner at the time? I don’t know / I’m not sure
Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’ but didn’t give a ‘no’
How would you best summarize people’s reactions to 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
You have a hookup story to share? Submit it here!