Craigslist Success

by Frank

Gender: Male
Age: 38
Race/ethnicity: Caucasian
Current location: Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: College Professor
Relationship status: Attached
Religious affiliation: Absolutely none
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? I have never been with another male but it’s not outside the realm of possibility.
How many sexual partners have you had in your life (including oral sex)? 20? estimate.
How many hookup stories have you here posted before? 0

Craigslist Success

How long ago did this hookup happen? A week 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…)? One night stand (though she did email me looking for another “date”)

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? We met on Craigslist. Other than face pics and the little info we had exchanged, we were complete strangers. She was open about being a BBW and made no attempt to hide it, though she was bigger than I had imagined when I arrived. I wasn’t immediately attracted to her but I wasn’t turned off either. I do like big women after all. At worst I’d be getting off. I met her at her house.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We planned only the initial meeting via email, along with a little about our sexual interests. She told me that she gets very wet, orgasms easily, and is a squirter. All of that  sounded just fine to me! She made the initial post and I responded.

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 started by smoking a joint, and we chatted a bit while we smoked. She was friendly and I was confident we’d actually go through with the arrangement. When we got back from our joint, she wordlessly walked into her bedroom so I followed. We sat across from each other on her bed, and after a couple of awkward moments, I leaned in and kissed her, and things progressed quickly from there. She was wearing spaghetti strap shirt so I pulled the straps down and sucked on her nipples, and she rubbed my cock and started undoing my pants. She got up and stripped quickly, so I did too, and lay back on her bed. I started fingering her and almost immediately she both came (squeezing my fingers really hard!) and squirted all over my wrist. She hadn’t lied. She was kind of straddling me as I fingered her and tried to shift herself onto my cock, which I wasn’t cool with since I wasn’t wearing a condom, so we kept going with the fingering a bit while she stroked me, and she had another orgasm or two. Hard to say. At any rate, after a bit, she wanted to fuck, so we got a condom and I bent her over. She wanted to get fucked hard and I obliged. She came again and squirted all over me, which was pretty fucking hot, I must admit. Her pussy squeezing me was intense, though, as was the hard fucking, and so I came pretty quickly. I went down on her after this, which was not the greatest… she was a big girl and I couldn’t breathe for a lot of the clit licking, and again, she squirted a lot. I felt like I had gone for a swim? I washed up and came back hoping for a blowjob! which she gave for a few minutes before asking to fuck again. I obliged but couldn’t really get it up for the second round so it wasn’t spectacular. I fingered her to a final orgasm. She was good in bed and I am a BBW lover, but she was a little too big even for me and so I didn’t feel 100% into it. That said, she was pretty great in bed and willing to do whatever, so I think I’d give it another go.

Did you have an orgasm? Did your partner(s)? I had two. She had multiple.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms and pill (according to her).

What were your REASONS for having this hookup? Casual sex is simple, it’s about fulfilling a desire via the most direct route. I also need to be discreet for my work and my partner. It also allowed me to explore my BBW fetish.

Were alcohol or drugs involved? If so, how much? Marijuana (just a little)

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? I initially was a little disappointed, because the second round wasn’t that great and the head was great but far too brief. The extreme amount of squirting was also a little gross, especially during the oral. That said, we emailed again after the fact and the next time we’re in the same town I’ll certainly drop her a line again.

To whom did you talk about the hookup? How did they react? Nobody.

Was this a consensual and/or wanted experience for you? For your partner? yes.

Do you regret this hookup? If so, why? No.

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 first session of intercourse was fabulous. The squirting made things a little messy. I’m a fan of casual sex so this didn’t change anything for me.

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

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

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

What’s Your Fantasy? Click here to be part of the largest survey on sexual fantasies ever!