What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Executive
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
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)? 144
How many hookup stories have you here posted before? 10

The Teen with Tats

How long ago did this hookup happen? This week

What was your relationship status at the time? In a relationship (monogamous)

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

How long did you know the person before this hookup? For less than a week

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 former MILF fuck buddy of mine emailed me last week. I thought she wanted to get together again but instead she said the daughter of a friend of hers confided to my friend that she wanted to sleep with an older man without any complications or online dating, etc. So my friend was wondering if I could help out. Ever the gentleman I suggested we meet (the three of us) to better understand the conundrum. I met “Tracy” and my friend. Tracy was 19, very pretty and slim, with blue streaks in her blonde hair and some visible tattoos. I was instantly drawn to her before realizing it could be my daughter! At any rate it was a fun meeting, we talked a lot and we agreed to get together soon.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few days later, in the driving rain, I drove to Tracy’s apartment she shared with others. She was off on a weekday and the large apartment was empty. Between the space and the cool weather outside it was perfect for a romp with a teenager. We chatted a bit, and I promised her I would be gentle and sweet as I sensed some nervousness. I was attracted to her tight, short black dress. She had a few partners in her young life but obviously no one as old as me. After some time she leaned in for a kiss on her mattress on the floor — and was on top of me in seconds.

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 made out passionately for a while, taking me back to my youth. I started moving my hands to explore her young and in-shape body. She put her hands on my raging cock under my jeans. I started to take off my shirt and soon I was introduced to a work of art — awesome tattoos all over her body. I took time to explore her perky breasts, flat stomach, firm ass and strong legs before licking her panty-covered pussy. In minutes I pulled off her undies and went down with my tongue for a good 15 minutes. For me the thought of eating out a teen-ager was a remarkable sensation. For her — well, she couldn’t stop moaning in delight. We then moved to a 69 position and then she on top with my cock rubbing her clit. For a young , shy woman she had the right moves! She then reached for a condom and slid it on me and began our intercourse with her on top. That’s where I admired the tattoos and lovely breasts. We tried a number of positions, including me carrying her around her room before I came while doggy style. For someone who wanted to experiment sexually I’d say she was well on her way and had sex like a pro. Afterward we cuddled under the sheets and talked about her future plans. I gave her some good advice that I hope will stay with her. She thanked me for treating her well and helping her fulfill a fantasy. I couldn’t get over that I had slept with someone nearly 30 years younger!

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? We texted each other to compliment our love-making skills. It’s possible we’ll get together again but that’s uncertain.

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, Attraction to partner(s), Learning new things, experimenting

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? I told my MILF friend that we had a great time. She’s happy she connected us.

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? Sleeping with a teen-ager. There’s something about it when you could be their daughter.

What was the WORST thing about this hookup? I am married, so there’s that.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Just as individuals are different, so too are sexual needs.

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? I’m starting to think that it’s impossible to stay monogamous.

What do you think about the Casual Sex Project? Keep up the good work

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