by Jess

Gender: Female
Age: 32
Current location: Denver
Highest education received: College degree (eg., BA, BS)
Occupation: Comedian
Relationship status: Deeply in Love
Religious affiliation: Calvinist
How religious are you? A little
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Hetero but experimented with women
How many sexual partners have you had in your life (including oral sex)? 40+
How many hookup stories have you here posted before? None

Lost My Bra

How long ago did this hookup happen? Four Years

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

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? I’ll call him Mike, I met him that night at the bar.  He was handsome with black hair and light brown skin, fit and about ten years older than me.  He bought me a drink and sat down and I was quite attracted to him which is why I agreed to go back to his room.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A little background to shed some light on why I hooked up with Mike.  I am a Stand Up Comedian and on the road quite a bit usually for a few weeks at a time and then home for a week or two.  I had also just broken up with a serious boyfriend of several years and had not been dealing with it well and mostly handled it by sleeping around.  In two months I probably slept with a dozen different guys.  I also really enjoy sex.
I had done my routine at a casino in the Midwest.  It had been a bit nicer so I had worn a dress on stage.  I had gone back to my room, shaved my legs and made sure around my pussy was trimmed and made sure I was showing a little cleavage.  I was just about three weeks since my breakup. I went down to the bar and being honest here I was looking to get laid.
A few people recognized me and bought me drinks.  The first was a couple, the second was a guy I was not interested in and Mike was the third.  He was in a suit and bought me a drink and he was handsome and charming.  He said he had seen my show and thought I was funny and we talked a bit and flirted.  Generally I stay away from fans (I have a bit of a following) but that night I didn’t care.  Mike said he was in town on business and asked if I wanted to go back to his room and I said yes.

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? I was a little nervous, I always am with a new partner and I was a bit drunk.  Still we got back to his room and he started kissing me.  He took my dress off and then it was as if a switch flipped.  Mike pushed me down on the bed and pulled my bra and panties off.  We made out naked for a bit and he fingered my clit a few times and played with my tits and sucked on them.  He then penetrated me and rode me for about ten minutes before he came.  It felt good but I didn’t orgasm
We waited about half an hour before we went again.  We talked for a bit and he asked about my tattoos, they all come with a story.  Second time we had sex was about the same as the first but I moaned a lot and screamed a bit, I always get loud close to climax and had an orgasm.  Mike shushed me a bit and looking back I think I laughed a bit.
We relaxed again and talked some more, and then he began to suck on my tits and then lower.  Mike went down on me and it felt amazing and I had a rather intense orgasm.  I was fingering his cock a bit and offered to blow him but he said no and we fell asleep soon after.
In the morning we had sex again just standard missionary with a lot of making out and we both had orgasms close together.  We ate some room service and made out some more and then I went to get dressed to leave.  I couldn’t find my bra which we both thought was pretty funny and I ended up letting him keep my panties too since they were part of a set.  I kissed Mike goodbye and did the walk of shame back to my room.  Still he was a great lover and I really enjoyed myself.

Did you have an orgasm? Did your partner(s)? I did three times and Mike did three times as well

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms for any penetration but we didn’t really discuss STIs

What were your REASONS for having this hookup? Dealing with my breakup and I was horny, and mostly because I wanted to

Were alcohol or drugs involved? If so, how much? I had a few drinks and was a little drunk.  At the point where inhibitions were gone and I let Mike have me but not that he should have felt guilty

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? I had to get on the road, had another show a few hours away that next day.  He texted me a few days later when he checked out of the room, said he never did find my bra.  Unlike most of the men I slept with during this time, I wouldn’t have minded seeing Mike again but it never quite fell together.  I stayed in contact with him via text and email for about a year and we were even in the same town a few times, but it never quite fell together for us to get together again.  I broke contact when I went monogamous with my current boyfriend.
A few months back I came across Mike’s Facebook, he is now married with a kid on the way.  I am happy for him.

To whom did you talk about the hookup? How did they react? Don’t think I ever told anyone specifically about mike but a few friends and my current boyfriend know I went through a bit of a slutty phase between relationships.

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

Do you regret this hookup? If so, why? Not at all, unlike most of my hookups during this time

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 sex was pretty good and the worst part was it was only one night.  During this time I was struggling with the ideas of monogamy and marriage and casual sex.  I didn’t mention it above but my relationship had been five years and ended due to cheating I learned it was ok to have sex for pure fun when I was not in a relationship.  I found that I feel the idea of marriage is a bit outdated but that I can have a monogamous relationship.
About this hookup though, this was one of the few during this time I rather enjoyed and felt better about myself after.

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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