Exploring With a Friend

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, I don’t know exactly how many
How many hookup stories have you here posted before? Several

Exploring With a Friend

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…)? It was a one-off thing with a friend

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? A little while back, I submitted a story on this site about cheating on my girlfriend at university with R, one of her housemates. M was another housemate of my girlfriend and R. She was a tall brunette with nice curves and a really sexy Irish accent. We were friends and I knew she’d always been attracted to me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Shortly after I’d broken up with my girlfriend, I ran into M on a night out in a club. We were both quite drunk, and to cut a long story short we ended up making out in the club and she asked if she could come back to my place. We walked back, talking drunkenly about music and mutual friends.

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 went to my room and were making out on my bed when M stopped and told me that she was a virgin and that she’d never gone beyond kissing a guy before, but she wanted to start. We kept making out and gradually removed each other’s clothes until we were both completely naked. I got her to lie on her back and I knelt on the floor and spread her legs and went down on her for a while whilst reaching up to squeeze her breasts and stroke her nipples. After that, I fingered her and she seemed to enjoy it but she told me her clit was too sensitive and stopped me before she came. I asked her if she wanted me inside her and she said she wasn’t ready to go that far, so I put her hand on my cock and she gave me a hand-job instead. We did this with me lying on my back and her lying next to me, until the end when I rolled her onto her back, positioned myself above her and came on her breasts. We lay there and talked for a couple of hours and then started making out again. M said she wanted to give me a blow-job, so I stood up and she sat on the edge of the bed in front of me and sucked my cock. She didn’t want me to come in her mouth, so I pulled out at the end and she finished me off with her hand and I came on her breasts again. We got into bed and fell asleep. In the morning, M gave me another hand-job and this time I rolled her over and came all over her arse cheeks.

Did you have an orgasm? Did your partner(s)? I had several. M didn’t – I wanted her to but I couldn’t finger her or go down on her long enough to make her come as she said her clit was too sensitive and asked me to stop.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None, but there was no penetration involved in the end so we didn’t need to.

What were your REASONS for having this hookup? I was drunk and horny. On some level, it was sort of as a favour to M, as she wanted to explore her sexuality a bit with someone she felt comfortable with, and we were friends and very relaxed with each other. But that’s not to say I didn’t enjoy it myself, it was fun!

Were alcohol or drugs involved? If so, how much? Yes, we were both drunk to start with, although things continued the next morning when we’d sobered up.

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? M and I became even closer friends but we never hooked up again. Not long afterwards, she started seeing her first serious boyfriend and they are now married. She moved back to Ireland so I rarely see her these days but we stay in touch.

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? No.

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? It was exciting to be doing these things with someone who was experiencing them for the first time, and as we were friends it felt quite intimate even though it was pretty dirty and involved me coming on her three times!

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

All things considered, how NEGATIVE was this experience? Not at all negative

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