Hotel Bar

This post is sponsored by The T Bar.


What’s your gender? Man
How old are you? 62
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Massachusetts
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Consultant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Open for Experimentation
How many sexual partners have you had in your life (including oral sex)? 100+
How many hookup stories have you here posted before? 1

Hotel Bar

How long ago did this hookup happen? Today

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

How would you best classify this hookup? Paid sex

How long did you know the person before this hookup? Just met that day

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? At a NYC hotel bar in midtown. A woman 2 stools over who looked she was waiting for someone caught my eye. She looked older with a little more cleavage on display than most at the bar. When the person who had been sitting between us left, we started to chat.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Very quickly Tina told me she was a masseus and asked if that was of interest. I told her I was naughtier than that. She broke the ice and started a negotiation that ended with us agreeing on a price for sex X2 orgasms (I thought) and we went up to my room, stopping at the ATM on the way.

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? Tina was quite carnal and after a little bit of small talk she was in pantyhose and nothing else, on her knees, sucking my cock (with a condom on). She was enthusiastic about giving me head and between the suction and her hands I blasted into the cover after about 10 mins. She cleaned me off with a warm cloth and we started talking about psychology and politics. After about 10 mins I asked her if she was ready for round 2 and if she wanted to fuck. Instead of mounting me she started giving me another blow job while fondling my balls and stroking me. I figured out I wasn’t getting into her pussy, but her attention felt good and she stayed with sucking and stroking long enough to get me off a second time, about 15 mns by the clock. When her mouth wasn’t on my cock she was a very dirty talker, which made the encounter even hotter.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, one

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 as she dressed. She left. I felt relaxed and completely drained. It had been at least a year since anyone had sucked my cock and I thought that it should happen more often.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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? Very

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. This is a covert activity

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? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Sexy lips on my cock, the feeling of fucking Tina’s mouth

What was the WORST thing about this hookup? Not fucking her pussy.

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? Somewhat positive

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

Anything else you want to add about this hookup? It was my first time engaging a paid partner in a pickup situation rather than with the web or by phone. I could have made a better deal…

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I like sex with new people but don’t want to risk complications. I love a paid encounter from time to time so I can get what I need.

What do you think about the Casual Sex Project? Love the opportunity to share. Other’s stories get my hopes up

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