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? 2 so far

My 3rd Craigslist Hookup

How long ago did this hookup happen? June 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 53, white, and reasonably fit with dirty blonde hair. We were complete strangers to each other. She had placed a Craigslist ad and I responded to it. After my last hookup that ended somewhat disappointingly, I was a bit anxious but hopeful this would go better.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was with my army national guard unit for a week of some specialized training, and they had provided a hotel room for me for the week. I typically don’t go out in the evenings, but wanted some companionship, so I decided to hit up Craigslist to see if there were any ads in the Casual Encounters section that looked interesting and post a few ads of my own.

For most of the week, this seemed like an exercise in frustration. I couldn’t get a single response from a genuine woman who wanted to hook up, and every reply I sent to other ads went unanswered. Finally, I received a reply to a response I had sent in to an ad that looked interesting, and we began to talk via email and text. I found out she was nearly twice my age, which made her concerned. I assured her though that age wouldn’t be a problem with me.

I told her where the hotel was and we agreed on a time to meet. I waited for her outside, and she spotted me when she pulled up. We went to grab a bite to eat at a nearby restaurant to break the ice a little and get more comfortable with each other. This helped both of us relax a little, and by the time we got back to the hotel room we were ready to jump in bed.

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? When we got back inside the hotel room, she went over to the bed to lay down and gave me a compelling “come hither” look. We began to make out and undress each other on the bed while kissing, rubbing, licking, and sucking various body parts as we went. She sucked my cock for a while, and I returned the favor by eating her pussy until she was starting to cum. She let out a loud moan and arched her back while her juices ran down my face. It was incredible!

I got up to dry off my face, and she pulled a condom out of her purse and slipped it onto my cock. Then we jumped back in bed and fucked vigorously in a few different positions. I can’t remember details, but she definitely knew what she was doing and was obviously enjoying every minute of it. I’m not sure how many times she came while we fucked, but by the time I finally reached my climax I was spent.

After we cleaned up a little, we cuddled for a little while in bed, still naked. We talked about several different things, some sexual and some not, while coming down from the experience until we begin to drift off for a brief nap. After several minutes of semi-consciousness, she decided it was time to go. She got dressed, kissed me hard, thanked me for a wonderful evening, and left.

Did you have an orgasm? Did your partner(s)? We both had orgasms.

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

What were your REASONS for having this hookup? I wanted to bounce back from my last disappointing hookup and hopefully prove right the saying, “third time’s a charm.” I’m happy to say I accomplished both.

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? This was the first hookup I’ve had where I didn’t feel any lingering guilt afterward. I felt really good about the whole experience and would have loved to meet her again sometime for another hookup. However, she wanted it to stay a “one time only” experience since she’s been burned in the past by fuck-buddies who have gotten too attached. I can completely understand and respect the sentiment.

To whom did you talk about the hookup? How did they react? I’ve told a few friends and sexual partners, but have never gone into detail before.

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? 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 best thing about this hookup was that it was my first 100% positive hookup experience. This experience made me much more confident in my own sexual abilities and went a long way to dispel any lingering fears or trepidations I had been having about casual sex.

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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