by Danny

Gender: Male
Age: 31
Race/ethnicity: White
Current location: Texas
Highest education received: Some college (currently in college)
Occupation: Tech support
Relationship status: Engaged
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 10 (8 intercourse, 2 oral only)
How many hookup stories have you here posted before? 1 so far

My 2nd Craigslist Hookup

How long ago did this hookup happen? Spring 2011

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? She was 50 and reasonably fit with short dark hair and tan skin. She was married, but not happily and told me that she likes to hook up with younger guys to give her the sexual satisfaction that she can’t get from her husband anymore. We had not met in person before the hookup. We had only exchanged emails and a few pictures.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Since I had successfully hooked up once before by responding to a Craigslist ad, I decided to place an ad of my own. In order to help filter out fake responses, I asked any serious responders to include the word “green” in the subject. After wading though so many obviously fake responses, I found one that looked legitimate. I responded, and we began to exchange pictures and plan our hookup over email.

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? She came over to my house while my wife (now ex-wife) was at work (as stated in my previous posting, my wife had given me the go-ahead to experiment with other women but she didn’t want any details about it), and I took her back to the bedroom. She was obviously nervous and not very talkative. I did my best to we warm and friendly to put her at ease.

We undressed each other, and I massaged her back to help her loosen up. This led to some kissing and fondling and groping. I had her lay down on her back while I moved in between her legs and began to give her oral sex. Her pussy was very clean and sweet-tasting. Finally she was looking like she was starting to enjoy herself. I took her moans of pleasure as my cue that she was ready to fuck now.

I got up to put a condom on and then got into missionary position, but her libido seemed to have cooled off somewhat. Her pussy had constricted, and I couldn’t slip my cock inside her. We tried a couple of other positions to see if that would work better, and we both tried stimulating her clit, but nothing seemed to be working. She encouraged me to try to force my cock in, which I finally managed to do, but I could tell it was uncomfortable for her so we stopped. We got up, got dressed, and she gave me a kiss goodbye and left.

Did you have an orgasm? Did your partner(s)? Neither of us climaxed.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore a condom. We each claimed to be clean.

What were your REASONS for having this hookup? I had hooked up with a stranger from Craigslist before and was feeling a growing urge to try it again.

Were alcohol or drugs involved? If so, how much? Neither drugs nor alcohol were involved.

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 tried contacting her afterward to say that I understand if things felt awkward and would be willing to try again later. I never received any response from her and have not heard from her since.

I felt some guilt about having sex with someone other than my wife, but not as much as in my first hookup. Mostly, I just felt disappointed that it had not gone very well and was starting to think that I was incapable of having casual sex that wasn’t disappointing in some way. My next hookup would assuage those fears, but that’s another story.

To whom did you talk about the hookup? How did they react? I’ve told a few friends and sexual partners, but I’ve never given a detail account. They usually respond with something like, “That’s too bad.”

Was this a consensual and/or wanted experience for you? For your partner? Yes, it was consensual and wanted by both of us.

Do you regret this hookup? If so, why? I regret that it went so poorly and that she apparently did not want to have any contact with me afterward.

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 thing about this hookup is that I have been able to use it as a learning experience for how to tell when things just aren’t going right and to not “force it” (literally or figuratively) when that happens.

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

All things considered, how NEGATIVE was this experience? Fairly negative

Anything else you want to add about this hookup or anything else? Several months later, I posted another Craigslist ad, and she responded to it not realizing it was me again. I emailed her back, but once again she would not respond.

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