by John Wilmot

Gender: Male
Age: 62
Race/ethnicity: Mixed
Location: East Coast
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Artist
Relationship status: Married
Religious affiliation: Buddhist
How religious are you? A little
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Experiential
How many sexual partners have you had in your life (including oral sex)? 60-70
How many hookup stories have you here posted before? 0



How long ago did this hookup happen? Yesterday

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Paid sex

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? BL is in her early 20’s, very attractive, about 5’5″, 110 #, long dark hair, with a very fit, well proportioned body, a nice small tight ass, long legs and firm and natural B’s. She has Italian blood, with smooth light olive skin, and was shaved all over. 

She had been advertising on the local fuck boards starting 3-4 years ago, and has had pictures and presence on various discussion forums. I was into her look, had always wanted to see her, but never got around to it. Her review pages indicated that she was very open, friendly and personable, and not mechanical in her “services”.

In the past year, she seems to have gone UTR (under the radar), and had generally disappeared from cyberspace. Her review threads were closed, her pics and website disappeared. I did see that she was occasionally still doing doubles with a friend of hers, so I knew she was somewhat active, at least with previous clients or guys who knew how to get in touch with her. 

Knowing my window of opportunity may be closing with BL, I found her e mail address and reached out to her to see if we could arrange an hour’s meeting. While her response was not immediate, I did eventually hear back from her. She has a limited availability but was willing to see me. It took about a month of comparing schedules to be able to agree on a date.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I instigated by reaching out to BL. The gist of the planning was finding a mutually agreeable time to meet. We finally settled on an early weekday morning.  

I generally prepare for these trysts by showering, attending to my personal grooming, including shaving, meticulously, and dressing nicely, if casually. I also make sure I have correct amount in large bills in a small white envelope that I can discreetly leave on a table when I arrive. I then take a nice hit of pot before leaving the house. I brush my teeth in the car once I arrive at my destination.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? The meeting started with what is a standard two-call system for these situations. I called the morning of, and I got directions to her place, a pretty upscale apartment complex in the city, very near the freeway exit. Once parked, we exchanged texts, and I got her apartment number, instructions on how to get past the doorman (easy) and where the elevators were. 

I got to BL’s floor, made my way to apartment and knocked. The door swung open slowly, BL was behind the door. The big reveal! She was hotter than her pictures, and she was in heels and a red thong and bra set. I said hi, glad to meet you, etc. She put her arms around me and we kissed. I put my arms around her and cupped her ass. She then led me to her bedroom, while apologizing for the mess. It was very much a student’s apartment, and actually cleaner than most. 

We got to her room and chatted a bit to get a feel for each other. These situations are very intimate, but very bounded, and with experience you can get a good sense of the other person and generally make a connection very quickly, at least when it goes well. In this instance, it went very well, as BL is a very bubbly, fun and open person who really enjoys sex and her sexuality. I’ve found that the difference between impersonation and authenticity de minimis, as it seems that there is no way to invent a persona without putting yourself into it.  

I started by kissing her and taking off her clothes, including her heels. After a couple of minutes of touching and feeling, I took my clothes off and climbed onto the bed, when things got more serious. A lot of kissing and feeling, then I went down on her first, which she seemed to really enjoy, pushing and grinding onto my mouth. Eventually, to prevent a crick in my neck I slipped both my hands under her ass and lifted her hips up. She raised her legs to her shoulders and and her ass, not her pussy was in the center of my view. “Lick it” she said. I was glad to oblige, as she was very clean. I think she had her first orgasm soon after. We switched to 69, and then she wanted me to lie back so she could ride me while I felt her breasts and looked at her. A feeling of bliss and good fortune overcame me, and I was smiling ear to ear. Eventually we moved to missionary position, and we looked into each other’s eyes as our movements led to their eventual, mutually satisfying conclusion.

I held her in my arms for a while, then I laid between her legs and looked and played with her pussy.  We chatted a bit and I did get to know her situation, inasmuch as one can given the time constraints and the unspoken rules of the interaction.

She was a great lover, and I think the money exchange equalizes the playing field, and the participant to the transaction are then free to pursue desired ends with out secondary agendas. I have found a very satisfying and meditative state can ensue.

When things go well, which it did, the experience is definitely not anonymous or uncaring. Two humans have exposed very intimate parts of themselves to each other. 

I left a little after my hour was up, promising to see each other again.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom use.

What were your REASONS for having this hookup? Meeting a new person, getting physically intimate.

Were alcohol or drugs involved? If so, how much? A hit of Sour Diesel (pot) just before.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Got in my car and left her place. It was a beautiful morning, and getting laid for starters is like having dessert first. I hope to meet B again, and I felt that she was a very sweet person, open, vibrant and sexy. I have been looking for a new regular since the beginning of the year, and she is one of two that I have met that would qualify.

To whom did you talk about the hookup? How did they react? I never share any of my activities with anyone at all. I have occasionally posted anonymously on sexual review boards, and once in a while traded PM’s with other users of said boards.

Was this a consensual and/or wanted experience for you? For your partner? Yes and yes.

Do you regret this hookup? If so, why? Not at all.  As a matter of fact, I intend to repeat.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I had hoped to meet someone personable, sexual and physically attractive. BL pretty much fit the bill. In addition, she’s enthusiastic, funny, comfortable with herself, has a strong appetite for sex and has (literally) a professional skill set.

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

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

Anything else you want to add about this hookup or anything else? As BL is “under the radar” and does not advertise or tour, she meets her clients at her apartment. It was a little messy and not as luxurious as meeting someone at a 4 star hotel. I am used to shower facilities, fresh towels, mini-bar, etc.

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