Craigslist Hookup

by Jimmy

What’s your gender? Man
How old are you? 42
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Richmond
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Accountant
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 0

Craigslist Hookup

How long ago did this hookup happen? 1 year ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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? I met her on Craigslist. I was curious and made a posting. “Kate” was a divorced businesswoman that was going to be in town and she was very straightforward. She said she was a total freak that wanted to have some fun in her hotel while in town for work. She sent several sexy pictures and told me all about the dirty things she liked, such as group sex, dp, bdsm, anal etc. Pretty much you name it, she was into it. She said she really explored her sexuality after her divorce. And damn did that turn me on. She had medium auburn hair and was fairly attractive. She had huge D cup breasts and a sexy tribal tramp stamp. I thought it would be sexy to shoot all over it.

So we chatted about sexual interests and decided to meet. Her schedule got messed up for our first planned meeting so she found another and I thought it was over. She said he sucked so we worked it out for me to come by in the morning around 6 at her hotel.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I parked in the hotel lot and had some gum to freshen my coffee breath. Then I grabbed a recently purchased box of condoms and nervously walked into the hotel lobby. I had never had a planned casual encounter before, so my heart was racing like crazy. But as I was about to turn around she texted me another sexy picture and said she had a surprise hidden for me. I said fuck it and rode the elevator up to her room.

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 nervously knocked on the door and she quickly answered wearing some tight jeans and a wife beater tight over those hard perky nipples. We awkwardly said hi and then I just went for it and we made out passionately as I ripped her clothes off and threw her onto the bed. I quickly went down on her and tasted that pussy I had been craving. She clearly had been worked up with some toys around and boy was she juicy. She came for the first time so quickly and boy was she a moaner. Her moan was oddly sexy and just dirty sounding. I decided to look for my surprise and quickly had three fingers wedged in that tight ass that she had already lubed????I played around and used a nice vibrating toy. I did this while I licked her clit as she came at least 4 more times on my face with her just grinding juices all over my face. With all the assplay it was getting a bit smelly but we didn’t care in the horny heat of the moment. I pushed her to her knees and she did not hesitate to unbuckle my pants and start sucking my rock hard cock. She was really passionate with her sucking and you could tell she was a freak that just loved cock. I didn’t want to cum too quick so bent her quickly over the bed and gave her a few hard spanks leaving a huge red welt on that ass. I wanted her to think of me every time she sat down at work the rest of the day. I slipped on a condom and said, “Sorry but I want that ass baby.” She said, “Don’t be sorry for giving a girl what she wants.” Then she proceeded to guide my cock into her asshole. It was damn tight and only the second time I had fucked anal and I was in heaven. I fucked that ass like there was no tomorrow. When I knew I couldn’t hold any longer I ripped off the condom slung it on her back and came all over that little tramp stamp and collapsed next to her. She laid there slowly sucking the last of my cum out while I started to finger her again into a few more orgasms.

We were both covered with juices and damn her sheets looked like a mess for housekeeping. We showered together and fucked again in the shower after she kept sucking me to get me going again. I bent her face against the wall and fucked her until I came deep in her pussy. She begged me for it and I just went for it. We dressed and kissed again and I was on my way.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I felt kind of dirty the next few days and went to get tested asap and all was fine luckily. She lives in another city and we didn’t exchange contacts so likely never again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms, Birth control pill / patch / ring / injection / implant, Discussed STI testing history, Exchanged recent STI test results

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Power / Dominance, Boredom, It was easy / convenient

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I’m married

What was the BEST thing about this hookup? That tight asshole and her raw filthy sexuality

What was the WORST thing about this hookup? Cumming inside her and worrying about possible std

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It makes me want more.

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

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

Anything else you want to add about this hookup? She told me she still had cum leaking in her panties during her first work meeting.

You have a hookup story to share? Submit it here!