Unexpected Rebound



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 many sexual partners have you had in your life (including oral sex)? 20+
How many hookup stories have you here posted before? 2

Unexpected Rebound

How long ago did this hookup happen? Last night

What was your relationship status at the time? Same as current status

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 is 24, light brown hair, beautiful blue eyes, very cute girl next door type, with an absolute sweetheart personality, shes about 5’3″ or so, average weight few extra pounds around her midsection but she frequents the gym so shes in very good shape, I’ve always been an ass man but she has an amazing set of D-cups, speaking of ass hers is small but still nice, and for a short chick she has phenomenal legs. She is my friend’s ex-girlfriend, I’d known them both for about 3 yrs, they had been together for roughly 7yrs since high school but he was very neglectful and after some shit happened in her life it was more than the relationship could take and the broke up. Me and her had been close since day one, we just clicked, so after the break up we still maintained contact. There had always been some level of unspoken sexual chemistry between us, i definitely had an interest in her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it?  It had been about a month since the break up and she was still in a bit of a slump getting her life back together, we hung out at my place ordered a couple pizzas and watched some movies, we eventually fell asleep on the couch, when I woke up it was about 1 am, her head was in my lap, I did my best not to wake her but was unsuccessful, I said I’d grab her a blanket and pillow but she asked if I’d mind her sleeping in my bed, saying she missed the feeling of being with someone and it helped her sleep better, she asked for a t-shirt she could sleep in and then we crawled into bed, we laid on our own sides for a bit which seemed a little awkward so I reached over to put an arm around her and she immediately accepted and snuggled up, tossing a leg and arm around me and her head on my chest, I ran my fingers through her hair and up and down her back, I felt nice laying there with her, she started asking about my sex life, finally I asked what all the questions were about, she was a little hesitant but she finally spilled, her friends had been pushing her to find a rebound guy, but the only guy she had ever been with was her ex so she was a little inexperienced and didn’t feel right about hooking up with a random, we laid there in silence for a few minutes, I knew then we were going to hook up, I tilted her head up and kissed her.

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? She kissed me back and got on top of me, I removed her shirt and we began to attack each other, she was grinding me hard as I swelled up then everything came to a halt as she sat up, the room was dark so I couldn’t see her, but I felt her shuffle back, I asked if something was wrong, she yanked my boxers down then I felt her hand grasp the base of my cock then another on top of that, then slowly moved her hand up to the tip then I hear her gasp “Holy shit, i don’t think that’s going to fit,” I laughed a little and she quickly snapped back “Its not funny, I’ve never had anything that big,” I reached out and pulled her in and kissed her and assured her I’d be gentle, I kicked off my boxers as she removed her bra and panties, and lined up for missionary, she gasped as I slid the tip in, she was border line virgin tight but incredibly wet as I pushed the rest of the way in, I took it slow as she moaned and clawed at my back, after a while she loosened up and got comfortable with it and told me to get on my back so she could ride me, she didn’t have to ask me twice, she knew how to ride and she was loving ever second of it, I was playing with her tits when she caught me off guard and told me to choke her a bit, I was hesitant but she told me to do it again saying it made her orgasms more intense, so I reached up and put a hand on her neck, she placed her hands on my chest and began to buck her hips harder and faster than any other woman I’d been with, I warned her I wouldn’t last at this pace but she just kept going I tried holding back but it was no use I groaned and blew my load, she rode me all the way through my orgasm then she got hers, her body losing all control she collapsed onto me, her pussy milking my still throbbing cock. Our sweaty bodies laid there, panting heavily, neither of us really had words, we quickly passed out.

I woke up in the morning with a raging hard on and her clinging to me, us hooking up felt surreal but here we were naked in bed together, she finally came to and smiled as I stared at her, we kissed and she asked what time it was cause she had plans, she noticed my erection and said she really should go BUT if we were quick she definitely wouldn’t mind a repeat of last night, I pulled her on top of me and we started going at it, she reached down lined me up and took it much easier than she had last night, now that she was used to it I wanted to fuck her a little harder, so I tossed her off and got behind her, it may be small but she has a great little ass, I grabbed her hips and pushed my cock inside her, she yelped a couple times but begged for it harder, I was pounding every inch of cock I had into her guts, I could feel her bottoming out but she loved it, I remembered the choking thing from the night before and decided to pull her hair, she loved it, started moaning and saying she was close, I wasn’t far off either, hers finally hit her and she lost all ability to hold herself up, I fell to the bed with her, my cock slipped out and erupted all over her firm little ass and back.

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? We ended up showering together before she left, felt a little guilty banging my friends ex but the sex was amazing. We both agreed we should probably keep things quiet, even though we both admittedly have had a thing for each other for a while, she’s fine being FWB.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

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

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? It’s a friend’s recent ex

What was the BEST thing about this hookup? I’ve wanted to hook up with her for a while

What was the WORST thing about this hookup? Knowing we can’t be more

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

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

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