by

What’s your gender? Man
How old are you? 50’s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? In a serious relationship (open)
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)? 50+
How many hookup stories have you here posted before? A few

Bar Hookup

How long ago did this hookup happen? Last month

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? 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? Nice looking MILF type woman. I’d say a few years older than me. She was attractive with long blonde hair. She wore a loose fitting dress and heels. I went out of town for a conference and decided to go to a local bar. She sent a cocktail to me and I went over to thank her. We were both alone and she mentioned that we should move to a table to get better acquainted.

She told me that she was married but she and her husband were fighting. She decided to head out for a drink to cool off I guess. We talked for quite a bit and I asked her why she sent me a drink if she was married. Her response was that she just wanted to meet someone nice and possibly get some revenge since he cheated on her. I asked her if that meant she wanted to have sex, but she replied she wasn’t sure but was still enjoying my company.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She excused herself to the ladies room. When she came back we had another drink and it was obvious she was pretty tipsy. She was getting very flirty. I figured it was best to let her make a move since I wasn’t sure what her intentions were. Then she took my hand and slipped it under her dress. “Feel how wet I am?” she whispered in my ear. I asked if she wanted to take this to my room and she agreed.

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 my hotel room and sat on the couch. She leaned in an started kissing me which was nice, but suddenly she stopped. I figured that meant she was having second thoughts but she knelt between my knees and undid my slacks. I generally go commando so I was at full attention when she commented on my size and how well groomed I was.

At this time she got up and straddled me on the couch, her panties were soaked as she grinned on me. It started to feel pretty good when she stopped again. It was then she said fucking me would be going too far but she said she wanted to give me a blowjob as long as I didn’t cum in her mouth. She wanted it all over her dress and hair so she could go home to her husband covered in another man’s cum. She wanted to prove that she could find sex anywhere.

I agreed to it, but told her it had been quite some time since I came and there was possibly going to be more than she bargained for. She just smiled and said to give her some warning. Frankly she was excellent at oral sex with plenty of eye contact and just enough teasing to keep me on edge. Finally at the point of no return I warned her. She smiled and aimed it directly on her dress. I think she got a bit more than she bargained for since she exclaimed, “I’m soaked”!

With that she smiled, composed herself a bit but never went to the bathroom to clean up. She had my cum all over her dress which was very obvious. We said our goodbyes and thanked each other.

I often thought of her walking cum covered through the hotel lobby. I wish I was there to witness that.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

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? Not sure as we never spoke again

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

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

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

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? Somewhat

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? 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? Nobody

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Great oral sex

What was the WORST thing about this hookup? That she didn’t want penetration

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

All things considered, how NEGATIVE was this experience? A little negative

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