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What’s your gender? Man
How old are you? 46
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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Professional
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
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)? 3
How many hookup stories have you here posted before? 0

Sucked Off by Wife’s Best Friend

How long ago did this hookup happen? 20 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 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? Jennifer was in her mid-20s, pretty, a bit chubby with red hair. Very Irish-looking. We had gone to high school together, and I’d known her for many years. I think she might have had a crush on me at various points, but we were never romantically or sexually involved. She had been my wife’s roommate for a few years, and I’d consider her a friend, and she was a frequent visitor to our house.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We’d had some people over, and it got late. Everyone left except Jennifer and my wife. My wife fell asleep on the couch, while Jennifer fell asleep in our bedroom.

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? I went into the bedroom to move Jennifer out of our bed. She was known for never wearing underwear, and she had on a short dress that was pulled up, facing away from me, and her ass was exposed (I now wonder if this was a set-up). I decided to start fondling her ass, and she starting pushing back into me in a way that told me she liked it. I started to finger her pussy and she rolled over and spread her legs. I was impressed at how different her pussy was from my wife’s. My wife’s pussy is a massive “outie” with big labia. Jennifer’s pussy was just like a tiny hole with nothing surrounding it. I actually thought her pussy was kinda creepy.

After I fingered her for a few minutes, she said “I want to suck your dick.” She got on her knees on the floor in front of me and pulled down my pants. She the proceeded to give me the best blowjob of my life.

If I was to describe my wife’s blowjobs, I’d use the words “tickly” and “light.” They were/are nice, but they are definitely salad and not entree. I can’t come just from a wife BJ. I’d never really understood why BJs were held in such esteem.

Jennifer’s BJ was different. She SUCKED me off. It was like she was desperately trying to nurse the jizz out of my balls and into her throat. It was like she was in complete control of my cock, and I probably lasted about a minute. When I started cumming Jennifer pumped her head and lips in perfect rhythm to match my orgasm.

How sexually satisfying was this hookup? Very

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? I thanked Jennifer. We went aand woke up my wife, and my wife and I went to sleep in our bed, and Jennifer slept on the couch. The next day we all ate breakfast together. I walked Jennifer out to her car, and I told her that I was sorry that I’d started something sexual with her, but I also told her that she’d given me the best blowjob of my life, and I thanked her again. We never spoke of it again, and we never had any other sexual contact, but we continued to socialize routinely. I never told my wife, and I have had extramarital sexual contact since. My wife once told me that if I ever made a “sexual mistake” that she did not want to be told as long as I learned from it, and I honored that request.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Just happened, I don’t know why, just went along with it

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

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? I don’t know / I’m not sure

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? I don’t know / I’m not sure

Did your partner(s) consent to this hookup? You would need to ask her. She seemed like an active participant.

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? I don’t know / I’m not sure

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? A little bit

Why do you regret this hookup? On the one hand, I wish I could say I’ve never cheated on my wife. On he other hand, with the exception of a girl putting her mouth on my penis for about 30 seconds and then stopping due to guilt when I was a teenager, this BJ was the only sex I’ve ever had outside of with my wife (and the only orgasm ever given to me aside from my wife). Before we met, my wife had lots of different kinds of sex with lots of different people, so there is a part of me that it’s only fair that I got to experience someone else at least once.

What was the BEST thing about this hookup? I now get the hype about blowjobs. I’m glad I was able to experience a really great BJ at least once in my life.

What was the WORST thing about this hookup? Again, I wish I could say I’ve never cheated on my wife. Also, see below for unintended consequences.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It took years for me to realize that why that BJ was so good is that my wife is not good at sucking dick. I feel no resentment for that. However, that realization then led years later to me understanding that my wife is actually not a good lover. She has no interest in doing anything to please me aside from lying there and letting me use her body to get off. No kissing, no noise, no movement. Doggie is “degrading” and woman on top is “too much work.” If I want to play a little sex game I’m a “pervert.” It’s a strange predicament because I truly love my wife, I actually really adore her, and after a long marriage I am still extremely attracted to her, but I now realize that I’m never going to have a great sex life. In summary, this BJ made me realize what I was missing, but it took a long time to realize that because I never knew anything else.

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

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

Anything else you want to add about this hookup? With recent publicity regarding sexual assault, in the last year or two I realized that fondling a sleeping woman’s ass could have gone terribly wrong, and it probably wasn’t the right thing to do, although from Jennifer’s behavior she seemed not to mind.

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 envy anyone who has a partner who is interested in being an active, giving lover. Please realize there must be lots of us who want to be good, honest relationship partners and thus don’t get to have awesome sex lives. It’s not being “sex negative,” it’s just the way the cards were dealt. Retrospectively I wish I’d had sex when I was younger, but there is no way to change my current situation with leading to a lot of heartache.

What do you think about the Casual Sex Project? I have enjoyed many of the stories.

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

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