by Jesse

Gender: Male
Age: 52
Race/ethnicity: Caucasian
Current location: Central Texas
Highest education received: College degree (eg., BA, BS)
Occupation: IT Management
Relationship status: Married
Religious affiliation: None
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

Mature Man Meets Young Woman For Awesome Summer Break

How long ago did this hookup happen? 2 months ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Fuck-buddies

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? She is a young, very attractive college student. She is half Spanish and half black. She is tall, thin, and medium sized breasts. We never met before. I had been thinking about a woman just like her. It is amazing, like she was plucked right out of my mind. I know this sounds like a fiction, but that is exactly why I am sharing this. I can hardly believe it myself.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I placed an ad on Craigslist for a younger woman that is interested in experiencing an older man. Yes was the only (real) woman that replied. We emailed back and forth for a while, then we started texting. During our conversations, she said that she was 18. I have no interest in minors, and told her so. She said she could show me her ID when we met. Since she was staying at her parents house for the summer break, she invited me to come over during the day, when her parents were at work.

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 arrived, it was a little awkward. We hugged, then I checked her ID. Yeah, almost 19. Since she was the young inexperienced one, I took the lead. I started kissing her and she got really passionate. Throughout our first encounter, I would let her know what we were going to do next.

Did you have an orgasm? Did your partner(s)? Did we orgasm? Absolutely! She was so wet by time I was in her. I felt her orgasm just seconds before I did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We took precautions by wearing a condom. She said she only had one partner before me and that she tested clean in her last physical. I also happened to visit my urologist a month prior and tested clean.

What were your REASONS for having this hookup? Both of us had the same fantasy. I wanted to experience a young woman. She wanted to experience a mature man. Our fantasies came true!

Were alcohol or drugs involved? If so, how much? No drugs or alcohol.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After the first time, we were laying in her bed, catching our breath. Again, it started getting a little awkward. Neither one of us could think of any thing to say other than that was awesome, so I got dressed and left. We continued to email and text. To my surprise, she wanted to meet up again. From the second time on, we were both more relaxed and could carry on a casual conversation, so no more awkwardness. That continued until she went back to college for the fall semester. We still text and email occasionally.

To whom did you talk about the hookup? How did they react? I only have one person on this planet I could share this experience with. I have a friend from high school. We have become friends with benefits over the past couple years. I shared this experience with her. She was not too surprised since she is a cougar herself.

Was this a consensual and/or wanted experience for you? For your partner? This was definitely consensual for both of us.

Do you regret this hookup? If so, why? Do I regret the experience? No I don’t. As I mentioned, it was a fantasy come true. I count this as one of my lifetime experiences I will always remember and have fond memories of.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best part about the experience is how incredibly sensually exciting it was. The worse part was the risk of her parents coming home early and getting caught.

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

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

Anything else you want to add about this hookup or anything else? After this experience, I find myself wanting another one like it. Who wouldn’t want it again? I realize, however, this may be a once in a lifetime experience. I don’t dwell on that thought, however.

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