by Handsome Exec Virginia

Gender: Male
Age: 47
Race/ethnicity: White
Current location: Virginia
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Sr. VP
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Passionate
How many sexual partners have you had in your life (including oral sex)? 137
How many hookup stories have you here posted before?: 6

Craigslist Heavy

How long ago did this hookup happen? Yesterday

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…)? One-night stand

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 was a late-bloomer when it came to sex and once I became active many years ago I vowed to only sleep with women who are slim, fit or athletic. No heavies. Over the years there have been a few heavier ones, but never truly overweight. (I did have tremendous success sleeping with slim types). I’ve been scoping out Craigslist to see what’s out there and found an appeal from “D.” We connected only and agreed to have lunch. I liked our email conversation, though the photo she sent was not flattering. I ended up liking her a lot over lunch but left thinking I wouldn’t want to sleep with her. D is a bit heavier than I would like, my age, not all that attractive but very nice and engaging. But I was wondering: are the heavier ones good in bed? She said she was in a dead-end marriage and hadn’t had sex in 6 months. I could help!

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A few weeks passed and we picked a day to get together. I got a hotel room and she met me in the lobby. We went upstairs and talked to get caught up. We then started to kiss — and you know what? It was great! So it continued until we were disrobed and my cock was hard. She was heavy, indeed, but not too much.

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? After a lot of kissing, we explored each other’s bodies. We did oral – and again, it was great. At this point I was surprised that I was even aroused since her body type was not my preference. I tried to ignore the belly and thick thighs, but again it wasn’t bad at all. After 20 minutes of this she angled me on top of her, grabbed my cock and put it inside her – without a condom. The sex was better than I thought. We tried a few positions before I pulled out and sprayed on her tummy.

Did you have an orgasm? Did your partner(s)? Yes for me. She came twice.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. No discussion whatsoever. I’m clean and she hadn’t had it in a while in a marriage.

What were your REASONS for having this hookup? Curiosity — what’s a heavy woman like in bed?

Were alcohol or drugs involved? If so, how much?: None.

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? A little guilty since we’re both married. We might stay in touch but I don’t see this as a repeat performance when I have so many other options.

To whom did you talk about the hookup? How did they react? None.

Do you regret this hookup? If so, why? A little. We are both married.

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? Best was that my curiosity was addressed. It was also the heaviest woman I’ve slept with. I also pleased her, which is important to me. She left happy!

All things considered, how POSITIVE was this experience  A little positive

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