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What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Philadelphia
Highest education received: College degree (eg., BA, BS)
Religious affiliation: Christian
How religious are you? Somewhat
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 3

The pot smoking babysitter

How long ago did this hookup happen? 5 years

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For 1 to 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? Becky was a fellow parent in my daughter’s kindergarten class when we first met. We soon realized our daughters were good friends and that our sons were also the same age. She was about 5’8, overweight, with shoulder length black hair and brown eyes. She was very nice and helpful. When my son entered kindergarten, we needed some one to watch him a few days a week a after school.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In May, Becky hosted a birthday party for her oldest daughter. A few of the wives were outside talking about sex. Apparently, my wife had told them that I had a huge sex drive and lasted long after smoking pot.
In the following weeks, Becky started to be more flirty with me. I did not know what my wife said to the other wives. Becky knew I had a few days off while my wife worked. She asked me to come over one of the days, so we could smoke some pot. I said sure, I was always upto smoking pot.

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? When I got there I noticed her younger kids were not there. I thought it was she didn’t want her kids there while she smoked. We sat outside in her porch smoking. She immediately started talking about how her hubby was not pleasing her. She also said she saw how I looked at other women and flirted. She wanted to know if I ever cheated. I admitted that I did.

She leaned over to me and kissed me awkwardly. I was shocked. She said maybe we should move to the bedroom. I was hesitant as I was not sexually attracted to her. But I was not one to turn down sex. We moved to the bedroom and we kissed. Still I was not really feeling anything. It felted very forced. We stripped ourselves naked and got on the bed. I was still smoking some pot as she went down to suck my cock. She was talented cock sucker. She deep throated me, sucked on my balls and was very verbal telling me how much she wanted my cock.

I finally was super aroused and told her I wanted to fuck her pussy. She got on top to ride my cock. She was very awkward riding it. My cock kept popping out as she moved up and down. We switched to missionary. Her dirty talk kept up and I loved it. Our physical sexual connection was not very good. We could never get in a good rhythm together. She kept encouraging me to fuck her, but eventually I told her I think this isn’t right. As we laid in bed, she agreed.

How sexually satisfying was this hookup? A little

Did you have an orgasm? No, but I was close

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? We got dressed. She apologized saying her marriage was in a bad place. And she wanted to have an affair to see if sex would be better. I told her you can’t force it. There needs to be that certain attraction. She understood. I told her I was honored that she wanted me. She then told me what my wife had told the wives. We laughed. Our relationship has been awkward since, but it is still good.

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? Just happened, I don’t know why, just went along with it, It was easy / convenient

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

What substances did you consume? Marijuana, hashish

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

How wanted was this hookup for you at the time? Not at all

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

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? A little bit

Do you regret this hookup? Somewhat

Why do you regret this hookup? I should have stopped her when I thought the kiss was awkward

What was the BEST thing about this hookup? Hearing how much of a dirty talker she was.

What was the WORST thing about this hookup? The lack of sexual rhythm

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? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

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