Weird Week That Reminded Me When I Was In My 20’s

by Options111

What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? san jose
Highest education received: Some college (not currently in college)
What’s your occupation? Purchasing Manager
What’s your current relationship status? Single
Religious affiliation: Christian
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)? 200+
How many hookup stories have you here posted before? 0

Weird Week That Reminded Me When I Was In My 20’s

How long ago did this hookup happen? week of March 25th

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? 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? Well on Monday after two weeks of working like a dog to meet customer deadlines I get called into a meeting and told this is not working out, that’s never happened before, but thought it is what it is and took my 8K final check and went home. As I sat there, I jumped on a escort site and started just looking. I was feeling a little down due to the this is not working out statement, it was politics. So around 11PM I see something that makes me raise my eyebrows and I send a text to just inquire, inquiring lead to she is on the way, I have 8000.00 in my hand, hell no I did not deposit it, the company was in bad shape financially so I cashed it about 5 minutes after leaving. I thought to myself, OK lets see how this goes! I was incredibly stress free and relaxed, I had the biggest hard on that actually hurt it was so hard. She texted when she arrived and I greeted her as she was walking up to the front door. We hugged and introduced ourselves, she said what’s your name: I said, “My John name is Joe, but my real name is XXXX.” she thought that was the funniest joke she has ever heard coming from a client, she stated everyone is always wound tight, looking at her I knew why. I am not at all bad looking and I have dated women better looking than her, but what kept going through my mind is this women is beautiful and open minded, the women I dated were not that open minded, LOL. So after some chat she reaches down and she said I have never felt a cock as hard as this one is ever. I asked if I was her first, which made her unable to control her laugh which made her snort, that had us both laughing uncontrollably for 1-2 minutes. She said afterwards that she felt so comfortable with me and she has not quite had that feeling for any clients she has meet up to that point. That is where the story takes a weird turn! I paid 300/Hr but I had left 500 on the table since I had the cash, she said, “I haven’t even started and you’re tipping me.” I said, “I am not concerned with that, cause what you do is priceless, I cannot negotiate what you’re worth, cause you are worth everything in the world to someone.” She teared up a little and we had our moment then it turned into 2 hours of talking just laying on my bed. She turned off her phone and said, “you don’t mind if I stay a while?” I said not at all, I would love that. We spooned for a while, laid like couples do for a while and fucked our brains out for over an hour. The weird thing that happened is she never put a condom on me and we fucked 3 times resulting in me cumming in her. The craziest thing about it for the next 4 days I had called 4 different escorts. 3/4 as things heated up ended up fucking me bareback and letting me cum in them. I do not indulge in escorts but maybe once every 3-4 years, but I thought wow things have changed. Actually I do a lot of negotiating and leveraging, when I am home I want nothing to do with that, so I am actually more like the guy I was in my 20’s and I could always go out and hook up with the hottest chick in the room always on the DL, with what I was going through I found myself not working quickly due to a deadline, but more just talking about nothing which ended in something. I got checked out just out of concern and no I did not catch anything and the first escort calls me from time to time to hang out, no money exchanged, sometimes we have sex most of the time we don’t. She said that is what she appreciates the most about me,

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The internet

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? Head, with me working the clit, to bareback sex

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? Concerned about 3 weeks later got a check up and continue to do so every 3 months just for peace of mind.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? To cheer myself up

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? my close buddy, he said dude how the fuck do you pull that off. I wouldn’t even know where to start.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? I met a new friend

What was the WORST thing about this hookup? Nothing as of yet

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No

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

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

Anything else you want to add about this hookup? Wear a condom

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? Neutral

What do you think about the Casual Sex Project? Love it

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