Unexpected Online Hookup

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What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (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)? 5
How many hookup stories have you here posted before? 0

Unexpected Online Hookup

How long ago did this hookup happen? 4 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

How long did you know the person before this hookup? For less than a week

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 responded to an online ad my partner had posted. She was 23 years old, blonde, 5’5, thick but curvy body, and tattoos on her upper arms.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I responded to her online ad of looking to do something fun. She responded back to me that she was actually in need of some quick spending cash and looking to give a blowjob for $20. I wasn’t interested in paying someone but jokingly wrote that wouldn’t help her so she could instead fuck me for $100. I expected to be turned down and received a message that she couldn’t do that. A few days later, a message appeared asking if my offer was still good. I was horny and after some deliberation with myself I told her yes. I also told her that I would host if she provides whatever protection is to be used. She agreed and headed over once he exchanged the details.

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 she arrived, I was stunned to see that she was 10 times better looking than the photo she had sent. I led her to the bedroom and it was obvious we were both nervous. We chit-chatted for a few minutes about random things. She confided to me that I was the only real guy to respond to her ad so she decided it was time to give up some pussy. Eventually she asked if I wanted to get more comfortable and I told her yes. I asked if she wanted the cash before or after and she gave me a deer stuck in the headlights look but soon said after. I got naked as she undressed to just wearing panties. We kissed and I sucked on her large breasts until she moved down the bed. She told me not to cum in her mouth and then engulfed my cock giving me a really good blowjob. After a few minutes, her eyes looked at me and then came up asking if I wanted to fuck. I replied, “Yes, do you?” and she told me yes . She reached into her pants on the floor pulling out a condom. As I put the condom on, she pulled her panties off and spread on the bed. As we fucked in the missionary position, she started biting her lip. The only times she released from this lip biting was to speak to me. It felt so good having sex with her. We swapped to fucking doggie-style and she asked me to spank her some. While fucking doggie, she let out a few “oh, fuck”s. She was then orgasming with her pussy squeezing down on my dick. Once her pussy released, she asked me if I had felt that. We then changed to fucking on our sides then back to missionary. We were having sex for what seemed like hours and it felt incredible. I asked if she wanted to finish me with her mouth. She got down on her knees blowing me. I told her that I was going to cum but she kept going taking every drop into her mouth then swallowing. We laid together in bed for a few minutes and she thanked me for using a condom as she doesn’t want to get pregnant like this. While getting dressed, she told me that she had never done something like this before and had to tell herself it was just sex over and over on the drive over. I told her that she was really good in bed and she said that I was too. I pulled out the cash and she laughed saying she was officially a whore now then thanked me for not making her feel like one. She asked if she could write me in the future then gave me a hug and left.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 was ashamed that I paid someone for sex but didn’t feel bad about what happened and didn’t think I would hear from her again. She did write me again a week later and we had sex again. A month after our second encounter, she wrote me saying she was desperate for some cash. That third time we had unprotected sex and I never heard from her again. However, I did see her interviewed on the news discussing her new job working for Uber.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, I don’t know if my partner was on any (other) method

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? I don’t know / I’m not sure

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 never told anyone.

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? Not at all

What was the BEST thing about this hookup? The sex was the best I ever had.

What was the WORST thing about this hookup? That I paid someone to have sex.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I became more open to having casual sex instead of strictly with those I was dating.

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? I love the ability to see how others think.

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