by John Wilmot
Current location: East Coast
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Relationship status: Married
Religious affiliation: Buddhist
How religious are you? Somewhat
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? 1
My Own Private Lolita
How long ago did this hookup happen? 2 years
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? She had ads in a local board and her photos had been done by a well known glamour photographer. In the very tastefully done photos she posed in a lacy black bra and panties in a flood lit room. In another, she posed with a .44 Magnum, blowing the smoke from the barrel, her hand barely large enough to reach fully around the grip. That one caught my eye, not the usual prop for hooker photography. She was very pretty, a blonde, with medium length tousled hair, slim, punkish and very cute at 4′-11″. All of 90 pounds, maybe. She had small, perky breast, maybe B cups, but I am no expert at sizing. She went by “Jill Bait” and claimed to be 18. I knew she’d be young and but I’m pretty good at chatting people up, at least for a little while, so I was not worried about not being able to make a connection.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She had a” handler”, which was not surprising, as its hard to get a hotel room, rent a car or navigate the logistics of screening clients, etc. at that age. The handler put me off from seeing her, as well as the possibility of her being underage.
After about a year of seeing her ads, she changed her non de guerre to “L” and it looked like she had gone independent. In addition, she had been doing doubles with a regular of mine, so I got back channel confirmation that she was both legit and very sweet.
I was turning 60, and I wanted to treat to myself. As I’ve aged, my philosophy of gifting has evolved; now when I give a gift, it is something that the giftee would desire, but would never spend the money, either being too extravagant or being frivolous. It was time to apply this philosophy to myself, and I thought giving myself the gift of sex with “L”. Her rate was $400/hr, which is not an amount I spend lightly.
I emailed “L” and arranged a meeting. She was hosting an in-call at an upscale downtown hotel.
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? A beautiful mid-summer morning, I went downtown, parked the car and went to the park, which was starting to gather al fresco lunchers. I had been texting with “L”, she was running late and had not even checked into the hotel. Bad form to be late for these kinds of assignations, especially at this price level, a pretty high degree of professionalism is expected. The silver lining was that I’m pretty much guaranteed to be her first client of the day.
I ran into a friend that I had not seen in a long time and we had a great chat, a serendipitous way of killing some time.
Almost an hour later, I finally got “L”‘s invitation to come up to her room, with the instruction to come right in as the door would be open. I walked across the park to the hotel, nonchalantly crossed the foyer, found the elevator, went up to her floor, found her room and went in.
She was obviously not together, as she was still in the bathroom getting ready. Not what I would consider good trade craft. For her own safety and my peace of mind, she shouldn’t have been in the bathroom with the door to her suite unlocked.
In the tastefully decorated anteroom, I sat on the on a bench and chatted her through the door until she came out. When she finally appeared, I saw a beautiful, hot little blonde in panties, a bra and high heels, which brought her up to almost my height. She was nervous and apologized for her disorganization, but her beauty certainly made up for it as far as I was concerned. We kissed and fondled and quickly stripped down and moved to the bed. I started to go down on her, but soon found smegma between her labia. I like pussy very clean as I like to be uninhibited in my licking and sucking. I led her back to the bathroom, where I sat her at the edge of the tub and gently washed and cleaned her with a warm washcloth. Did I have tender paternal feelings? Who’s to say what passes between two people?
We went back to the bed where she was much more relaxed when she figured out that I was not pissed about her being late, etc. As a matter of fact, I was amused and pretty much in the moment as I generally have no script for these interactions. We went through the basic sexual repertoire, blow job, 69, cunnilingus, and fucked in missionary and doggie. She was so small, and I felt tender, cradling her in my arms, ravishing her gently. She herself was a good lover, and liked to please orally. She seemed reluctant to be pleased herself, but in the end lost those inhibitions.
Did you have an orgasm? Did your partner(s)? We both orgasmed, at different times. She when I went down on her, I when I was fucking her in missionary.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom for intercourse, no discussions.
What were your REASONS for having this hookup? Lust, new experience. I still find it amazing that one can hookup with very pretty and personable women pretty much on demand for a little bit of money. To some, $300 or $400 may be a lot of money, but it’s not when you can cut through society’s taboos and get laid with a lady of your choice, with impunity and very little to no complications.
Were alcohol or drugs involved? If so, how much? Some pot.
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? I saw “L” one other time, did a double with my regular girl. Obviously there is not future in these relationships, but I wish her well and hope she finds the life she is looking for. She has stopped advertising and I would guess is out of the business or has found a sugar daddy.
To whom did you talk about the hookup? How did they react? No one.
Was this a consensual and/or wanted experience for you? For your partner? Consensual.
Do you regret this hookup? If so, why? No.
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? The best thing for me was pinpointing my desires and getting exactly what I wanted. In addition, I became more conscious of the fact that despite the transactional nature of the sex, I generally am able to make a genuine personal connection within the bounded nature of the interaction.
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 or anything else? Two people meet, the hotel room door closes. Sex and maybe a little love ensues.
You have a hookup story to share? Submit it here!