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What’s your gender? Man
How old are you? 46
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Legal field
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 0

Trailer Park Trash

How long ago did this hookup happen? Last night

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? For less than a month

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 had met D on a Kik chat I got to through Craigslist. The focus of the chat was sexual, but there was no open hooking up in the chat as that was done person-to-person via PMs. She had posted some pics of her shaved kitty in the chat room and sent me some more personal pics via PM, so I knew she was fuckable. Because she lived over an hour away in the opposite direction that I typically go, I knew the best that would happen is that this becomes a weekend fuck-buddy situation.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Both D and I are football fans which was a connection. I am also a huge hockey fan, and I proposed that we go to a minor pro hockey game in her city. She agreed and we set a date for the next Saturday home game, in just over two weeks time. Over the two weeks we continued to text and there was no doubt that the hockey players were not going to be the only people getting physical activity that weekend!

D had cautioned me beforehand not to judge her for where she lived, as one of her responsibilities was to manage a trailer park. I was skeptical, but since I had already developed a connection, I elected to be non-judgmental.

During our texting, she had mentioned she’d been celibate (and hadn’t masturbated) for three years up until about five months ago when she masturbated for the first time. She had sent me a video she took of her masturbating and she didn’t just squirt, she gushed like Niagara Falls! It was incredible! Because of this I mentioned I had had a vasectomy and tested clean just a month prior, and assuming she was clean I asked if she had any objection to engaging in intimacy without condoms. She responded that she too was sterilized and had only had sex with one local person since the end of October. Thus we agreed that we would bareback.

She lived with her 23-yr old son in the trailer park, so I rented a hotel room immediately adjacent the hockey arena to avoid any awkward moments. I did not want to take any chances as to how this 23-yr old guy would react to some strange dude showing up and fuckin’ his mamma.

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 had offered to cook dinner for her, her son and his daughter before going to the hockey game. I saw the place she was living in, and was – quite frankly – disgusted and embarrassed for her. Nonetheless, I cooked a beautiful meal and we headed to the hockey game. We went to the arena to purchase the tickets and returned to the room. We had 45 minutes to game time, so we got naked, slipped under the covers, and started making out. I went down on her for about 20 minutes and I could feel her body tremor and shake, but she wasn’t able to orgasm. We then cleaned up and went to the game.

After the hockey game, we returned to the hotel room and had a tub together in the soaker tub to defrost from the cool arena. We were in the tub for about an hour, chatting about a variety of topics. At this time she told me she had been a drug user about a decade ago but has been clean for something like 5-7 years. I also told her that despite the texting for weeks, going to the hockey game, and eating her out before the game, I still did not know her name – only her first initial from her Kik handle!

After the tub, we hopped back into the bed under the sheets and started snuggling and making out. After some serious making out and some clit play, I was hard and decided to get on with the dirty deed. I mounted her in the missionary position and slid right in. It was such a beautifully tight pussy compared to my wife’s pussy, and I started to pump it. I would alternate between pumping hard and pulling out and just letting the head slide in and out of her inner pussy lips. This drove her crazy! After a few minutes of missionary, I got her to flip around and mounted her doggie style, with my left leg resting on the foot and the right on the knee. So transitioned from a stationary position to one where she was rocking back and forth in sync with my body to drive my cock in further. I again modulated my pumping and eventually busted a nut inside her. It was so beautiful – there is no more intimate moment that ejaculating inside a woman in your first lovemaking session. I then dutifully ran to the washroom to get the Kleenex box so she could clean herself.

We rested and chatted for a bit, and about 1 am we started going at it again. This time I was too tired to cum and my pecker went all “wet spaghetti” on me. We washed up and laid in bed chatting some more until we went to sleep at 2 am.

What I find disturbing was that as we were relaxing and engaging in post-coitus conversation, she took out her phone and showed me a video of doing reverse cowboy on some dude. I asked her rhetorically if it was the local guy she had sex with a few times before and to my surprise, she said it was someone from the chat group. I was literally shocked – she had told me she had only had sex with one guy since testing last April, but this was clearly another person and was recent since the chat group had only been going a month or so. The dude was clearly wearing a condom and she had mentioned she had unprotected sex with the local dude, so maybe this was what she meant? I was unsure, but it raised issues with her credibility.

Before going to sleep, I told her I would probably wake up with morning wood and would roll her over and have sex with her to address it. I jokingly told her it wasn’t rape if I told her in advance, and we both had a laugh at that. Sure enough, at around 5:30 am I woke up with morning wood. I started to spoon her, adjusting her buttocks so my hard member shipped between her butt cheeks, but did not enter her. For about 60 seconds I kept moving it in an in and out motion, which caused her to stir.

I snuck out of bed to get my Astroglide lube, coated my cock, and went back to bed. I peeled the covers back, rolled her from her side to her back, raised and spread her legs, and then slide myself in. In return, I received a long groan of pleasure. I continued to pump her for a few minutes before getting her to flip onto her knees and I moved to doggie. After a few minutes of doing her doggie style my body realized it was still morning and went wet spaghetti again. I pulled out, and we both went back to sleep.

At 8 am I again awoke with morning wood and had her get on her hands and knees so I could do her doggie again. After about 5 minutes I unloaded in her, shooting my semen into her pussy.

After nutting in her the second time, we decided to go for breakfast and then sit in the hot tub prior to checking out. We did this, checked out and went on our merry ways.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? No

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? Despite the ethical lapse, I suggested she come spend the weekend at my place in two weeks so we can continue our tryst. She was open to this suggestion.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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 yet.

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? A little bit

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Finally connecting with someone I’d been texting with for a few weeks, and whom I saw photos of their intimate regions and a masturbation video. Also, ejaculating directly into her vagina. There is nothing more intimate than finishing in your partner.

What was the WORST thing about this hookup? The lost of trust over the mysterious lover that she did not previously admit to. It led me to question most everything she told me about her past sexual life, including the long celibacy.

The realization that we’re from opposite sides of society. She, her lifestyle and her circle of friends represent the stereotypical trailer park trash reputation. For example, she said she caught her boyfriend in the spare bedroom with another trailer park resident while his two pre-teen children were in the house.

Also, the realization that

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The lack of full disclosure is a reminder that Craigslist is Craigslist! While I’ve met some great people through Craigslist, it’s certainly not a trusted source of casual sex parties.

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

All things considered, how NEGATIVE was this experience? A little negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? My spouse resides 3,000 miles away with our children. Humans have needs to be met, and casual sex is one outlet. Prior to relocating to California 28 months ago, I had never been with another woman and probably will not be with another woman when we co-locate. But having casual sex with many women have been a huge learning experience given my lack of partners.

What do you think about the Casual Sex Project? Excellent idea.

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