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What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York City
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Bartender
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? >100
How many hookup stories have you here posted before? 0

Sex With A Married Cougar

How long ago did this hookup happen? 2 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? First of many

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? I’m a bartender in NY. Due to the nature of the job, there’s a code between bartenders. “If you go home alone then it’s your choice.” I just found this site and I plan to add a few of my experiences. This story is one of my top 10.

It was a busy Friday night and an attractive older woman sat at the bar and ordered a drink. She was wearing a tight business suit that hugged her firm figure. I noticed she wore a wedding ring with a huge diamond. I’m usually good at guessing a woman’s age, but I was wrong with her. I thought she was in mid-40s40s, but she was actually in her early 60s. She was alone, so I flirted a little because that always helps with tips. She ate up my compliments, so I kept it up. She was looking me up and down and flirting back. That’s usually a good sign if a hook-up is going to happen. I got a little more information about her. She’s married, a real estate lawyer in Manhattan and lives in the upper district. She was staying at a hotel in the city to stay out late and ‘blow off some steam’ from a hard week at work. Not long into the conversation, she was very direct with what her idea of ‘blowing off steam’ was. She was looking for a guy to have sex with but she noticed most of the guys were much younger and didn’t think she would have a shot at anyone due to her age. She thought about leaving and trying out another place. I tossed out some compliments and asked her to stay and try. She was hesitant at first but I told her if she has no luck, I’m more than willing to leave with her. She petted my hand and told me thanks.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It slowed down around midnight and she was still hanging out at the bar. I asked if I could leave and got approval. I held her hand and we left. Knowing this was a ‘sure thing’ I squeezed her ass. I was impressed at how firm it was. She gave me a kiss in the elevator.

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? Once we got to her room, we were having sex within minutes. I was expecting this to be a ‘hit it and go’ situation but we ended up having amazing sex all night. We did it four times. She was amazing! At one point, she was bent over and I was doing her from behind I said, “You’re husband is one lucky bastard.” She loved the compliment & quickly rewarded me too. We were both tired and she asked me to stay, and we fell asleep in the bed.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Around 8am, I woke up with ‘morning wood.’ She took care of it. I was about to make my exit, but she insisted we shower together first. OMG, that was an amazing experience! She ordered breakfast through room service and we ate & talked. We were both wearing hotel robes and I looked into her crystal blue eyes and I told her how pretty she was with no make-up on. She is a natural stunning beauty. Deep down I wish she was my age and single.

We’ve met up a few more times. She’ll find out my schedule and on my days off in, she’ll stay in the city at a hotel. She insists I stay with her. We stay busy having amazing sex. The sex is great and she’s become a close friend.

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

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

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

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 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? A few friends. They were impressed when I told them how wild she was in bed.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? I met a great person and we’ve become friends. The sex is still amazing!

What was the WORST thing about this hookup? I wish she was much younger and not married. She’s the type of woman I would love to have had the opportunity to date.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Older women married women are fun to have sex with.

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

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

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? It doesn’t bother me to have sex with married women. Being a bartender, most of my casual hook-ups are with married women.

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