Wine One More Time

by Trib

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Business
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
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? 1

Wine One More Time

How long ago did this hookup happen? 2 months ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? 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? This woman is a work colleague. She is around 45 but is a knockout. She has magnificent boobs and butt, but her sexiest thing is her smile. We have worked together for a few years, and gotten along well. We have also traveled previously and there is another story on this site about a previous trip. I’ve always liked her. I’ll call her P.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Much like the last time, when we are in the home office, we are friendly, we joke, but it is still very professional. This time we were traveling in Asia to visit a company office. A third colleague was with us. We went out for a fabulous dinner and all three people were enjoying themselves, but only P and I were drinking wine. After the meal, we went to an outside terrace and continued drinking and talking. At around 11, our colleague called it a night, and we continued drinking. We had planned after our last semi hookup to not let it happen again, and it was time to go back to our rooms and as we were heading there, she suggested we find another drink and the only place serving at that time was room service. So off to her room we went. We got to her room and the wine arrived. She was wearing the sexiest outfit romper style shorts all in black.

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 got to her room, the wine was poured and within minutes we were kissing. Oh my god she can kiss. Her tongue danced around my mouth and I could feel the heat rising. I asked her to dance and we put some music on the phone and we swayed slowly, kissing and our bodies getting closer. She then said we should get into bed and finish what we started. I unbuttoned her shirt and the romper came down that beautiful body and within 10 seconds her bra was off and I was sucking on her beautiful tits. She loved it and arched her back to push her boobs towards me. She was down to her panties now and I could see the wetness of her pussy through them. I pulled the panties aside and began to lick her pussy and she immediately put her hands on my head to pull me in. It was only a couple of minutes but it was time for me to get naked as well. She climbed on top of me and reached down and maneuvered my cock into her pussy. She was tight and glorious and starting rocking back and forth on me and I was going to blow it quick. I switched positions so I was on top and her legs went up over my shoulders and I started slowly but gradually could not control it. As I thrust into her, she started grabbing and spanking my butt and the back of my legs and moaning. She was very verbal – saying she loved my cock inside her and kept asking me how sexy she was – and god, was she! After a few minutes, I could feel my load blow into her (I am fixed) and collapsed.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? We talked and cuddled for a few hours after and fucked one more time. We both eventually fell asleep but I woke up an hour later and got dressed and went back to my room. I could not find my underwear anywhere though.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Hoping or expecting it would lead to something more, Thought it was an important experience to have, Intoxication

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not 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 gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Are you kidding?

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? A little bit

Why do you regret this hookup? It will never lead to anything and it is hard seeing her at the office.

What was the BEST thing about this hookup? The connection, the fun, the laughter

What was the WORST thing about this hookup? leaving her there in the bed

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

Anything else you want to add about this hookup? No

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