My 4th Craigslist Hookup

by Danny

Gender: Male
Age: 31
Race/ethnicity: White
Current location: Texas
Highest education received: Some college (not 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? 3 so far

My 4th Craigslist Hookup

How long ago did this hookup happen? July 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 a bigger girl in her mid 20s, Hispanic, and had long dark curly hair. We were complete strangers to each other and had not met or communicated at all before the night we hooked up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Once again, I was in town for my army national guard drill weekend once a month and staying in a hotel room provided by my unit. Still flying high off of the success of last month’s hookup, I decided to hit up Craigslist again and found a promising ad from a woman who wanted someone to come over tonight. I scanned for the usual red flags and determined the ad was worth responding to. A couple of short emails had me convinced she was legit enough, so I was soon on my way over to her address.

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 was waiting outside for me when I arrived and walked me inside. She nervously told me that she’s never hooked up with someone from Craigslist before, but she hadn’t had sex in nine months and and that she “has needs.” She was self-conscious about her body, so she took off her clothes while under a blanket. I slowly took off my clothes, being sure to keep engaged in friendly conversation as I did so to help her relax.

Once we were both naked, I slipped under the blanket with her. We kissed and began to feel up and down each other’s bodies. I sucked on her ample breasts and kissed my way down to her shaved pussy. She started really letting go of her nervousness once I began tracing the tip of my tongue around her labia and lightly flicking it across the base of her clit. She tried to reciprocate by taking my cock into her mouth, but she admitted that she didn’t have much practice with blowjobs and it showed. I told her it was ok and I didn’t expect her to do anything that she wasn’t comfortable doing.

At that point, she was ready for me to enter her. I was on top of her missionary-style and gently guided my cock to her pussy, which opened easily as I slid deeper inside her. We fucked with a gentle back and forth motion, slowly gaining momentum as we began to lose ourselves in the moment. She let out such sweet soft moans, and I could feel her clenching and unclenching around my cock as she savored every moment. Finally, I reached my climax and came deep inside her pussy. Our rhythm slowed, then stopped, and then we just laid there for a moment with my now softening penis still inside of her as we basked in the afterglow of the moment.

We rolled over and cuddled for a few minutes, but we decided it would be best if I didn’t stay too long. I had to wake up early in the morning and didn’t want to accidentally fall asleep in her bed. I got up, got dressed, gave her a deep kiss, and left.

Did you have an orgasm? Did your partner(s)? yes, we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t use any protection. I knew I was clean, and she had proof that she had just been tested. She was also on a birth control patch.

What were your REASONS for having this hookup? I wanted to have another successful Craigslist hookup after last month went so well. At this point, I was also hoping to find someone who was willing to become a fuck-buddy for when I was in town.

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? We texted back and forth for the next couple of days. We talked about how much we each enjoyed the experience. She was especially turned on by the fact that I came inside of her and told me about how she let the cum run out over her fingers so she could play with it after I left. Hearing that was a big turn on for me.

We texted sporadically over the next year and would often try to plan a time when we could hook up again, but our plans usually fell through. We did finally hook up again one more time, 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 and even gave a detailed account to an online friend that I have sense lost touch with. I was chatting with that online friend on the night that I had the hookup, so I told her what was going on before I left and told her how it went after I got back. She congratulated me for getting laid on such short notice.

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

Do you regret this hookup? If so, why? not at all

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 it not only went well for both of us, but she was still talking with me afterwards about doing it again sometime. This was a big boost to my self-esteem and a significant development point for my sexuality since I now felt it was likely that I could find a semi-regular fuck-buddy and didn’t have to rely on hoping I could land a successful Craigslist hookup with a total stranger to continue to experiment with having extramarital sex.

The worst thing about this hookup is that I was a little worried about how I had just had unprotected sex with a total stranger. There was a fear in the back of my mind that she would call or text me telling me she had gotten pregnant even though she was on birth control. Thankfully, that never happened.

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

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

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