by David

Gender: Male
Age: 29
Race/ethnicity: White British
Current location: London
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Investment Banker
Relationship status: Single
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? Over 250
How many hookup stories have you here posted before? Several

The One That Got Away?

How long ago did this hookup happen? About 8 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Sex with an ex

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? H had been an early girlfriend of mine when we were at school together when we were both 16. We were crazy about each other – looking back we were probably in love. We were together for a few months but the relationship eventually broke down because H was a virgin and I wanted sex and she wasn’t ready, and I behaved like a typical teenage boy about the whole thing. Anyway, later on H and I ended up going to the same university and I’d run into her from time to time. She was gorgeous – creamy skin, red hair, great legs, fantastic large breasts.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I ran into H at a house party one night, towards the end of our second year at university. We’d both already had quite a bit to drink by the time we got talking, sitting on a bench in the garden. She told me her boyfriend, who she’d been with since freshers’ week, had broken up with her the week before, and she was obviously still upset about it. We reminisced about when we were together as teenagers, and we ended up kissing for a while. I said “shall we go?” and she smiled at me and nodded. My house was just round the corner so we walked back there holding hands.

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? Once we got to my place, we sat on my bed and kept kissing. The weather was warm and she was wearing a summer dress and no tights so I put one hand up her dress and ran it up her inner thigh until my fingers were touching her pussy through her knickers. Then I slipped to the floor, hiked up her dress around her waist, pulled her knickers off, kissed her thighs and started going down on her. I kept going for a while but my neck got sore, so I switched to using my fingers instead and didn’t stop until she came. At that point, she took off her dress and her bra and she was completely naked in front of me on the bed. I took my clothes off too, got a condom from a drawer by my bed and put it on. Then I lay on the bed on my back and had her get on top of me, and she moaned gently as my cock slipped inside her. She rode me like that for a long time and I kept running my hands all over her body – her thighs, her arse, her hips – and squeezing her breasts and playing with her nipples. I remember she was moaning loudly and I knew my housemates would be able to hear her, but I didn’t care. After a while, I had her get off me and lie on her back and I fucked her as she wrapped her legs around my waist. She was moaning and gasping the whole  time with her breasts pressed against my chest and I fucked her faster and faster until I came.  We lay there and talked for a while and then she fell asleep with her head on my chest and my arm round her shoulders. We both woke up early the next morning and started again, kissing and running our hands all over each other’s bodies. I fingered her for a while and she played with my cock. Once she was wet enough, I put on another condom, then I rolled her onto her side so that we were spooning. I got my cock inside her and had my right hand holding her hip and my left arm wrapped round and underneath her so that my forearm was across her breasts and my fingers could play with her right nipple. I got so turned on watching her arse cheeks jiggle as my pelvis thrust against them that I just started fucking her quite hard and came pretty quickly. Once we’d finished, we more or less immediately fell asleep again.

Did you have an orgasm? Did your partner(s)? She did when I went down on her and then fingered her. I did both times that we had sex.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t discuss anything, but I used a condom both times.

What were your REASONS for having this hookup? I’d begun to develop feelings for H again after seeing her a few times not long before we hooked up, and I’d always regretted missing out on having sex with her back when we were together. Physically, she was completely irresistible.

Were alcohol or drugs involved? If so, how much? We’d both drunk quite a bit, but I don’t think it had any effect on the decision to hook up – I think we’d still have done it if we were stone cold sober.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? It was mid-morning by the time we woke up again. I gave her my dressing gown to wear and made her pancakes for breakfast before she went home. H was one of the few girls I’ve ever had serious feelings for. I wanted a relationship with her again, and we hooked up a few more times over the next couple of weeks. When I told her how I felt, she said she had feelings for me too but wasn’t ready for another relationship so soon and she decided it would be best for us to stop hooking up. We stayed friends for a while but both moved on and I hardly ever see her anymore.

To whom did you talk about the hookup? How did they react? Nobody.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both of us.

Do you regret this hookup? If so, why? I don’t regret it – the sex was mind-blowing and it was an absolutely incredible night. But what followed was difficult.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Everything about that first hook-up and the ones that followed was great. But H ending things was painful.

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

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

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