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? 4 so far

My 1st Successful Repeat Hookup

How long ago did this hookup happen? January 2012

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…)? 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? This is the same woman from my previous story, “My 4th Craigslist Hookup.” She is a bigger girl, Hispanic, in her early-mid 20s, and has long dark curly hair. We had first met six months ago when we originally hooked up and had not seen each other since. We had been texting back and forth periodically over the past six months and had been trying to make plans to hook up again. I was very excited that we were finally able to do so.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had spent months off and on texting back and forth how our next hookup would go. The plan was very much along the way our first hookup went. The next time I was in town, I would come over, we would have sex, and then I would go back to my hotel room to sleep. This time, however, she wanted to be a bit more rough and adventurous for the actual fucking. Last time she was very nervous and self-conscious, so the kind of slow and gentle sex we had was just what she needed then, but now she was more comfortable with the idea of letting go a bit more in bed.

Also, she had gotten an IUD since the last time we fucked, so there was no concern about the birth control failing. She definitely wanted me to cum inside her again and assured me that she was still clean.

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? I drove over to her house, and she came outside to meet me on the front porch. She gave me a passionate kiss and led me inside. We chatted a little while we stripped, and then she started sucking my cock. I noticed how much more at ease she felt this time. She didn’t seem the least bit self-conscious about her body like she did last time. Also, her cock sucking technique had greatly improved. She had told me before about the boyfriend she had between our last hookup and this one, so I knew she had been practicing.

Eventually, I pushed her back down onto the bed and dove my face in between her legs and began to eagerly eat out her pussy. She started moaning and squirming to the point where she was begging me to fuck her. I happily obliged by sliding my cock into her pussy and started with a slow but steady rhythm missionary-style. I started going harder and faster for a while and then suggested she try being on top. We switched positions, and she straddled me while I was on my back. I guided my cock into her as she lowered herself down into position and rode me for a little while.

She wasn’t too comfortable with the cowgirl position though since she was a bigger girl and was worried about being too heavy for me. I assured her that it was fine, but she was ready to switch positions again soon anyway. This time we got into position for doggy style. I held onto her hips while she bounced her ass against my crotch. She would bury her face in the sheets and moan every time I plunged my cock deeper into her. She told me she wanted it rough, so I grabbed her hair with one hand and pulled her closer to me. I started slapping her ass with the other, and she started bucking her hips back against my crotch harder and harder. We both came hard, and I filled up her pussy with my cum. I will never forget looking at that beautiful cream-filled pussy as she slumped forward with her ass in the air after I pulled out my spent cock.

She rolled over, and I laid down on the bed next to her. She cuddled up to me and then reached between her legs to let some of the cum drizzle on her fingertips. After showing me her cum-drizzled fingers, she licked them clean and smiled.

We talked for a few minutes about how much fun we had and how this hookup went differently from our first one. I got dressed, gave her a passionate kiss, and then left.

Did you have an orgasm? Did your partner(s)? Yes, we both had an orgasm.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I did not use protection. She had an IUD, and we both assured each other we were clean.

What were your REASONS for having this hookup? Our last hookup went so well, so we wanted to have another one.

Were alcohol or drugs involved? If so, how much? Neither alcohol nor drugs 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 continued to text off and on for the next several months. We both felt great about the whole experience and wanted to do it again. Unfortunately, we never got the chance. I haven’t heard from her in about two and a half years.

To whom did you talk about the hookup? How did they react? I’ve told a few friends and sexual partners, but have never given a detailed account until now.

Was this a consensual and/or wanted experience for you? For your partner? This experience was consensual and we both wanted it.

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 this is the first time I’ve had two successful casual sex experiences with the same person. The worst thing about this hookup is that this was the last time we saw each other. Our lives and schedules turned out to be incompatible to become even semi-regular fuck-buddies. However, this did give me an idea of how things would progress if I ever did find a fuck-buddy, which was good for the development of my own sexuality when I later upgraded one of my friendships to friends-with-benefits, but that’s another story.

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

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

Anything else you want to add about this hookup or anything else? My wife at the time (now ex-wife) and I were trying out polyamory at the time, and her new boyfriend stayed with her during this weekend while I was out of town. She was having sex with him for the first time while I was having this hookup experience, so that was going on in the back of my mind the whole time.

Later that month, my wife and I separated. She got entirely too wrapped up in her new relationship and wasn’t interested in me anymore. I was devastated and wasn’t interested in having sex at all for about three months afterward. That’s where my next story will pick up.

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