Wine Soaked Night

by Trib

What’s your gender? Man
How old are you? 55
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 occupation? Sales
What’s your current relationship status? In a serious relationship (monogamous)
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)? 4
How many hookup stories have you here posted before? 3

Wine Soaked Night

How long ago did this hookup happen? 1 month ago

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

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

How long did you know the person before this hookup? For more than 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? She is a work colleague and a sexy, fabulous, and spectacular person. She has a great body and knows it, and she is not shy when she has a drink or two in her. She is full of life and a great spirit to be around.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As always, when we travel together for work, we tend to spend a lot of time together. We were at a regional office together and ended up having dinner together, and several glasses of wine. She was getting very suggestive and we ended up back in her room after the bar closed so we could order room service.

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? Almost immediately after the door closed for the wine order, she was undoing her top and I could see her fabulous tits. She has the best boobs I have ever seen. They are full and young-looking, with small, pert nipples. She told me to look the other way while she slipped into her pajamas – a slinky camisole and pajama pants. Of course, I could not help taking a look at her fabulous ass as she pulled them up.

We drank a little and kissed deeply, our tongues enjoying each others’ mouths. She told me to slow down a bit and be more gentle and probing with my tongue – I’ll remember that forever. My hands were rubbing over her covered tits and her pussy through her pajama pants. She lifted her arms so I could peel her top off and I kissed and sucked on her tits. She moaned and my hand slipped down her pajama pants past her shaved mound and into the warmth of her pussy. She was so wet and eager. In a minute, she was naked and with legs spread wide open, and I tongued, fingered, and licked her for 15 or 20 minutes while she writhed and groaned. I switched up the position and asked her to bring her pussy up to my face while I laid on my back, and she did. I could look straight up past her great tits and into her beautiful eyes.

We must have started fucking 3 or 4 different times, and each time she would play with my cock and bring me closer to the edge. Finally, she squatted over me so my cock entered in her and I could feel the weight of her tits on my chest as she rose up and down on my cock. I came suddenly, in her. I know she is on birth control.

After a few minutes, I wanted to make sure she was satisfied. I played with her with my fingers, and whispered dirty things in her ear. She pulled my other hand up to her throat while I fingered hard. I told her I wanted to fuck and eat her every day. I wanted my cock in her mouth, pussy, and ass. She told me she loved watching porn and dreamt of being with another woman, so I worked that into my sex talk – I would fuck her while she ate the pussy of another woman. She must have come 4 or 5 times during this 10 minutes of pure sexual energy. We were spent, but still used the rest of the night to cuddle, kiss, suck and fuck some more. In the morning, I had to travel to another city, but knew I would catch up with her later that day.

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? As this was the third or fourth time, and I know I have feelings for her, it made it difficult how we walk away from each other each time, but I know I love her as my fried and occasional fuck buddy and I hope it continues.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Intoxication

How intoxicated were you? A little tipsy/high

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? no one ever

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