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)? About 250 to 260
How many hookup stories have you here posted before? Several

Double Trouble

How long ago did this hookup happen? Two weeks 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…)? One night stand (two one-off hook ups in quick succession)

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 couple of weeks ago, I was at a conference in a pretty upmarket country house hotel. On the first night, there was a dinner for about fifteen of us in the one of the function/dining rooms. There were two waitresses serving us. Both were blonde, but one was curvy and tanned whilst the other was petite and paler. They must both have been in their early twenties.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a couple of glasses of wine, I began taking every available opportunity to flirt with them both, and they both flirted back. At the end of the evening, everybody left and somehow the curvy waitress and me were the last two people in the room. I asked her if the bar was open so I could have one more drink and she said yes and that she’d come through and serve me. We talked and flirted some more whilst I sat at the bar drinking a glass of whisky, and she laughed at everything I said and was clearly into me. At 1am she told me it was time for the bar to close and the end of her shift. I asked if she wanted to come up to my room, and she said ok.

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 room, we started kissing and slowly removing each other’s clothes until we were both naked. Then she got on her knees on the floor and sucked my cock for a bit. Then I fingered her a little to make sure she was wet enough and we moved to the bed. I put a condom on and she got on top of me, and for a while we just had sex like that, with her moaning as I squeezed her breasts. Then, I had her hold herself still above me whilst I thrust up into her hard and fast from below. My hips were smacking against her arse cheeks and her breasts were bouncing around and she was moaning more and more. At the same time, I worked her clit with my fingers and I managed to time it so that just as she came, I came inside her as well. Afterwards, we chatted a bit more and she laughed and told me how much she’d ‘needed a good fuck’. Then she said she’d better get home, and she got dressed and left.

When I came down to breakfast the next morning, I noticed that both waitresses from the night before, the curvy girl I’d fucked and the petite girl, were serving again. The curvy girl smiled at me as I walked in and every time I caught her eye. Then I noticed that the two of them kept whispering to each other and glancing at me, and when the petite girl brought me my food she said “is there anything else I can do for you, sir?”, in a flirtatious way. After I’d finished, just before I got up to leave, she came over, looked around to make sure nobody could hear her, and told me that her shift finished at 2pm and if I wanted her to she’d come up to my room. I was a little surprised by how forthright she was, but of course I said that sounded like fun and gave her my room number.

I made sure I got away from the session of the conference I was supposed to be attending in time to be back in my room by 2pm. About five minutes later, there was a knock at the door and I opened it, and in walked the petite waitress in her uniform of tight black shirt and pencil skirt. She told me that she’d been feeling really horny lately and that her friend had told her I was good in bed. I played in cool and suggested she take her clothes off, and in quite a matter of fact way she just stripped off in front of me. We started kissing and I squeezed her arse and played with her breasts before fingering her. As she got more and more excited, she started whispering “I want you to make me come” and I kept working her clit until she did. After taking a moment to recover, she removed my clothes and played with my cock a little and then I sat on the edge of the bed and she got to her knees on the floor and sucked it for a while. Then she stopped and told me she wanted me inside her, and I told her to get on her hands and knees on the bed whilst I got a condom and put it on. She was ready and waiting for me and moaned as I entered her from behind. There was a huge mirror on the wall to our right and we could watch ourselves in it and see absolutely everything, which was really hot. I fucked her gently at first, but with the view in the mirror and the fact she kept moaning and smiling at me in it I couldn’t help myself, and pretty soon I started pounding into her hard and fast, my hips and balls smacking against her arse cheeks, until I came. Afterwards, we lay on the bed naked and both agreed the sex had been awesome. I told her I needed to take a shower and get back to the conference event I was supposed to be at, and she said she’d better get home and got dressed and left.

Did you have an orgasm? Did your partner(s)? Yes. The first girl came whilst I was having sex with her and fingering her. The second girl came when I fingered her. I came whilst having sex with each of them.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No discussions but I used condoms with both girls.

What were your REASONS for having this hookup? I hooked up with the first girl because I was horny and bored and it turned out she was up for it. The second girl initiated things with me herself, and it was too good an opportunity to turn down as she was gorgeous.

Were alcohol or drugs involved? If so, how much? I’d had a few glasses of wine and a whisky when I hooked up with the first girl, but wasn’t really drunk. She was sober. With the second girl, both of us were 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? After I’d hooked up with the petite waitress, I didn’t see either girl again. They weren’t at the hotel for the rest of the day or the next morning when I left. I enjoy a lifestyle of having a lot of casual sex with a lot of different women, but even so hooking up with two complete strangers so soon after each other, and in those circumstances, was something new and exciting for me.

To whom did you talk about the hookup? How did they react? Nobody – I don’t usually talk about my sex life.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for me and for each of the two girls.

Do you regret this hookup? If so, why? No. Both hook ups were hot and fun, and none of us wanted or expected anything further to come from them.

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? The best thing was really hot sex, twice in less than 24 hours, with two different gorgeous girls. There really wasn’t anything bad about it at all!

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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