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What’s your gender? Man
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? 0

Wine will do it every time

How long ago did this hookup happen? Two days ago

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For 1 to 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? I’ve worked with her for 3 years and we’ve been good colleagues for that time. We had never hooked up before, but one business trip a year earlier, when I made sure she made it back to her room after a night of drinking, she kissed me drunkenly. I got her to bed, but it stuck in my mind for a year. She is very attractive 44 year old with a great body and a fun attitude.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were again on a business trip and after dinner with another colleague continued with some more drinks in the hotel lobby. We were sitting closer and closer as the wine drained, and again she kissed me a quick peck, but that progressed to deep French kissing and some light over the top feeling of those magnificent tits. I brought her back to her room but basically poured her into her bed and went back to my room that night.

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? Skip to night 2 of the trip and back in the hotel lobby after a cozy dinner at an area Italian restaurant. More wine, and same scenario, but less time went on before I took her back to her room again. This time, she was much more aggressive, pulling me onto her on the bed and where we kissed more and her tits were starting to come out the top of her dress. I kissed her tit lightly and she got up and peeled off her dress leaving her in bra and nylons. I pulled the bra down to suck er nipples and the bra came off. We continued to kiss lightly and then deep French kisses, with her gasping between each kiss and arching her back to encourage me to play with her tits. And they are magnificent – the best I have ever seen! My hands roam down her back her nylons, pulling at her ass. She flips over and lifts her hips so I can peel off the nylons and I get my first glimpse at her beautiful shaved pussy. I go down on her – she is very wet and play with her with my fingers and tongue. I am still mostly clothed at this time, but proceed to strip down. We roll around the bed for a bit, but due to the 4 bottles of wine we shared, I was not able to get a particularly firm erection and honestly in the back of my mind was nervousness and concern we should not be doing this. She reached down and gave my cock a few quick jerks, which helped, but in the end we did not have sex and neither of us had an orgasm. We did start to talk and lay there and she fell asleep in my arms.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, not even close

Did your partner have an orgasm? No

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? Guilt came quickly. Never done this before and she is a friend. We chatted a little about it and both our memories were shaky. We said this would never happen again but part of me hopes and wonders. I like her.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Intoxication

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? No one

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Very much

Why do you regret this hookup? We talked and agreed it was a bad idea but I was always the one who looked out for her – and I did not that night.

What was the BEST thing about this hookup? Seeing those boobs – I hate to be so carnal – but I had wanted to see them for years.

What was the WORST thing about this hookup? Aftermath and emotion

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? yes

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Fairly negative

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