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What’s your gender? Man
How old are you? 27
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? South America
What country and/or city do you live in? Colombia
Highest education received: Some college (currently in college)
What’s your occupation? College Intern at a School
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Slow, passive, spontaneous
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 1

A Paid Release

How long ago did this hookup happen? One Week Ago

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

How would you best classify this hookup? Paid sex

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 was looking of an escort on the internet, and I found this hot, blonde, bespectacled MILF-type woman that was showing her face, had fake tits but a natural and great ass, so I contacted her through WhatsApp about her services. After she confirmed she was in fact the woman I was looking for with the guarantee that if she wansn’t when I came to her place I could decline the service, I asked her for a budget about her services, and then after agreeing to have anal sex with her as an extra service, I stipulated an hour to meet, and she accepted while answering me about my questions with patience and some terms of endearment, and finished the conversation by asking her to meet me with her signature glasses, a dental floss thong, something resembling a fishnet, and basic baby doll lingerie or something that I saw in one of the pictures that looked hot on her. So, just like that, I went so see her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She provided her services mainly in a hotel, where a receptionist asked me for some money to pay for the room, and she pointed me towards said room she was in. After I knocked on her door, this hot MILF opened her door and with a smile, a hug, and an attempt at a kiss. She let me in with an affable behavior she maintained during the whole thing. She was indeed dressed in the fishnet lingerie and thong I asked for, and apologized for having a different set of glasses than the ones she had in her pictures which I didn’t mind, started to hug me again, tried to kiss me and tease me with her body. Previously, I told her I wanted to grab her tits and her ass since it was so big in the pictures, and in person, it looked so much better. I’m a smacker, so that’s what I did: I grabbed her big ass, smacked it several times, buried my face between her cheeks while she was moving accordingly and pushing it at the same time towards my face. I wanted to lick her butthole, but I restrained myself for precautions. After that, she made me suck on her tits, and I gladly complied while she was (probably fake) moaning. She laid on the bed after I asked her if she could turn on the lights, which she did, and I smacked her ass some more while she was laying down doggy-style and pushing her ass on my dick. She was still affable and entertained during the whole thing, and indeed she told me during the service that she loved being an escort and that she could not give up on that job since she loved how much she, “liked getting fucked so good”.

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 asked me to lower my shorts and grabbed my dick through my trousers. When I took them off, she grabbed it and asked for a condom. Before that, I asked her if we could watch ourselves in a mirror, where I licked her cheeks and smacked them some more. After all that foreplay, I told her I wanted to fuck her. She took one of my condoms and put on in my dick with her mouth. It felt so great that I put my hand on her neck and started to push, to which she went along, but before I came, I put her in all fours on her bed and put my dick in her asshole. She asked me to push slowly. After only two thrusts, I came inside her, and then she proceeded to give me a massage while she talked to me about her life, her job as a licensed masseuse, and the fact that it was her birthday two days before the service.

I was horny again, so I asked for a blowjob which she gave me and I was below her, grabbing her ass, shaking it, smacking it again, and putting my fingers inside her vagina. She sucked my dick for a while before she sat on it by her own volition and started to ride me reverse cowgirl. I came after a while, but kept riding for a moment, and she climbed down after.

She offered me a shower which I took gladly to wash off the oil from the massage, and while I was there, she kept talking about herself, about her bussiness, the city’s climate, some feng shui thing she believes in, and other trivial things that didn’t bother me at all. She was very enthusiastic during the whole thing and a great service overall. She stole a bit of money from me but it didn’t bother me either since I gave her almost the exact amount and the change wasn’t much, and I went 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? I don’t know

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? After the hookup, I felt weird, with a load off of me, but with the regret that I had to pay money to have sex, and with a hot MILF that wouldn’t pay attention to me in different circumstances. I still feel weird up to this moment. I don’t know if I’ll ever ask for her services again, I need to have some money available as I did last week, and even then I don’t know if I’d take an escort again.

I was horny that day, I wanted to have sex so much, and as I said in a previous story, I’m not popular with the ladies, not precisely a catch, and most of the time I’m an awkward man.

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

What were your motives for this hookup? Fun, pleasure, horniness, To cheer myself up, I was feeling lonely, Boredom, It was easy / convenient

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? I didn’t speak to anyone about this and I don’t plan on telling anyone about this experience. I’d rather keep that to myself, besides putting out there on the Internet in a story like this.

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 had to pay for sex. It’s still sex, but I don’t know how other people have it easy and have sex whenever they want.

What was the BEST thing about this hookup? I wanted to fuck a hot MILF in the ass, and I did it. I was horny as hell and with money available, so I took the chance.

What was the WORST thing about this hookup? I had to pay for it. In other circumstances, a woman as hot as her wouldn’t give me a second glance.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. It made me realize how much I love sex, but also that I’m lonely as fuck, but I think I made it pretty clear throughout this story and the previous one I posted.

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

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

What do you think about the Casual Sex Project? It’s a great thing to have, I like this space where I can let it all out without someone judging me.

That I know of.

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