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? 0 (but will post more)

My 1st Craigslist Hookup

How long ago did this hookup happen? July 2010

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 + booty call

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 Hispanic, average height, and thin with dark hair. She was two years older than me and turning 30 in a couple of days. We had never met before, and had only exchanged a handful of messages and pictures before we hooked up. Other than that, we were complete strangers to each other. Before this point, I had never had sex outside of a romantic relationship and certainly had never hooked up with a stranger before. I was a bit nervous and excited to finally experience casual sex for myself.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My wife (now ex-wife) and I had been considering having an open relationship for a while. She had even had a girlfriend for a couple of weeks, but that had ended badly. This was almost a year later, and she had agreed that I could experiment with other women as long as I was careful, but she didn’t want to know the details.

Once a month I go out of town for drill with my army national guard unit, and they provide me with a hotel room for the weekend. I began searching through Craigslist ads for casual encounters for those weekends. I found one that looked promising, and we began talking via email a couple of days before my next weekend drill. I told her where the hotel was and what time to be there, and I would be outside to meet her.

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 showed up and spotted me, and I took her back to my hotel room. We sat on the bed and talked for a bit. She did most of the talking, actually. She opened up about family, friends, work, her on-and-off boyfriend/best friend, her past sexual experiences, and all sorts of things that I don’t really remember much of at all. I sat and listened and chimed in when I had something to add to the conversation until she was finally comfortable enough to get to the reason why we were meeting in the first place.

I remember very clearly what happened next. Silently, we each got up and stood on opposite sides of the bed, stripped, and walked around to the foot of the bed. We looked each other’s naked body up and down, and then embraced in a hard kiss.

After this point, it’s a bit fuzzy how things happened and in what order. I remember she gave amazing oral sex but did not want me to give her oral in return, which is a shame because I absolutely love giving cunnilingus. I fondled her breasts and licked and sucked her nipples. She asked me to slip on a condom, and I entered her. She was very wet and not tight at all. We fucked missionary, then doggy style, and back to missionary to finish up. Before either of us could cum though, she stopped and said she had to go because it was getting so late.

We got up and she got dressed. before she left, she pushed me down on the bed and have me a deep, hard kiss that made my head spin and then told me we would finish what we started tomorrow night. She promised me it would be worth my while.

I’m not sure I would say that promise really delivered. The next day, she told me she had a car accident on the way home. No injuries, but now she had no transportation. She asked me if I was willing to pick her up from work and then take her home after we were done fucking, and I agreed. I went to pick her up, but ended up getting lost for at least half an hour. Apparently my GPS interpreted part of a street number as an address. Anyway, I finally found her, picked her up, and took her back to the hotel.

This time we got down to business right away. We both stripped down immediately, but for some reason she insisted on leaving her bra on. After a little foreplay, she asked me to slip on a condom and fuck her. I didn’t want a repeat of last night’s unfinished business, so I fucked her hard and fast. I may have overcompensated because I came sooner than I had anticipated. I could see her starting to look a little disappointed when she realized I was cumming, so I kept fucking her until I started to go soft and then pulled out and fingered her until she came too.

At that point, she was really revved up, but my mood had started shifting hard after my orgasm. This was the first time someone other than my wife had brought me to climax, and I was starting to feel guilty about the whole thing. I rolled over on my back and she straddled me. She started playing with my cock so it could get hard enough for her to ride, but my head just wasn’t in it anymore. I told her the sex was really great, but I was spent for the night. She seemed disappointed but understanding.

Did you have an orgasm? Did your partner(s)? Not on the first night, but we both did once on the second night.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore a condom during intercourse. We asked each other about STDs and each said we were clean.

What were your REASONS for having this hookup? I was curious about and eager to experience casual sex for years. The thought of fucking a complete stranger is exciting to me. I’m not sure exactly what her reasons were for posting the ad in the first place, but I got the impression that she was no stranger to this sort of hookup.

Were alcohol or drugs involved? If so, how much? No drugs or alcohol for me. She brought beer and offered me one which I declined, and both evenings she admitted to smoking weed beforehand to keep from getting too anxious.

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 talked in the car when I drove her to her house, which was farther away than I had expected. I told her that she was the first person other than my wife that I had fucked, and she seemed a little surprised by that. She told me I was welcome to contact her again whenever I was in town, but I had no intention of doing so.

It was in the early hours of the morning when I got back to the hotel, and I was still feeling guilty. I sent my wife a text telling her how much I loved her, and eventually went to sleep.

To whom did you talk about the hookup? How did they react? I’ve mentioned it to a few friends and my current fiancé, but I’ve never told the story in detail before. I never told my ex-wife, and I doubt she ever found out about it.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual, and we both wanted the experience.

Do you regret this hookup? If so, why? I regretted it at the time because of the guilt, but not so much anymore since my wife at the time and I are divorced.

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 was to finally satisfy my curiosity for having casual sex with a stranger. This was a big step in my own personal sexual development. The worst thing about this hookup was the guilt I experienced about having sex and cumming inside someone other than my wife. Also, there really wasn’t much attraction or chemistry between the two of us. It made me realize how important those sparks are for even non-romantic sex and how awkward it can feel when they’re not there.

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

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

Anything else you want to add about this hookup or anything else? While my curiosity about casual sex was satisfied, my appetite for it started to slowly grow after this encounter. It was about nine months later when I finally decided I was ready to have another such encounter, but that’s another story.

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