Caught by the Zamboni Driver

by Rick

What’s your gender? Man
How old are you? 65
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? College Professor
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Jewish
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)? Almost 100
How many hookup stories have you here posted before? 1

Caught by the Zamboni Driver

How long ago did this hookup happen? 1 month

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 first saw Ashley on a sugar daddy website. I first thought that she was a catfisher, her pictures looked too good to be true. Young, thin, long blond hair, super cute smile.

I picked her up at her apartment near downtown. I was a bit stunned by her appearance, young, thin, blond. She was the girl in the pictures. I was nervous about her being underage that I asked to see her ID. She just turned 19. I’m 65.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The plan that we agreed to online was to go to lunch. I headed off to that direction. We started talking on the way and she talked a bit about needing money. I put my hand on her leg and she moved closer. I figured I’d go for it and I said that we didn’t really need to go to lunch, we could go right to a motel. She was good with it.

I hadn’t planned for this. I figured she that either she wouldn’t match her pictures or if she did, it would take more than one lunch to seal the deal. That’s why I scheduled a business meeting soon after lunch time.

She asks I smoke pot, but I decline, gave that up decades ago. I ask if she’s a user, and says no, just a pot smoker. I don’t know if I believe her.

As we are driving we are rubbing each other. Her tits are really small, the tit of a 19 year old girl. I have always wanted to have sex in a car and have never done it. So, I ask. She’s game. First, we go to stop in a convenience store, she buys condoms, I pee. We drive around and end up in a recreation area and park behind the ice skating rink that is quite deserted.

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’s at it right away, she knows what to do. Quickly, we are in the back seat. She’s naked, my pants are around my ankles, and she’s sucking my dick like a champ. It’s hard for me to cum usually, but I’m almost ready to burst. I stop her I want to stick it in. She’s game with that and we try a few positions in the back seat. Finally, I’m cumming in her, with the condom. I’m barely done when she says ‘Uh oh.’ I look where she is looking and there, out the back of the building comes the Zamboni. The driver is looking right at us. Shit.

I ask what do we do now, but quickly realize that best course is pull up the pants and high tail it out of there, which is what we do.

We try to find a place to have the lunch we were supposed to have in the first place but realize that I’m running out of time and I don’t really need to sit with her at lunch.

On the way back to her apartment I ask her to suck my dick, and she readily and enthusiastically complies. One problem, I didn’t take the condom off in the excitement and now it’s gone. If my wife finds the condom in my car it will not be good.

I drop her off at her apartment and we talk about a next visit. She’s good with an afternoon in a motel room and videos. I’ve got plans. I hand her some money, and ask if that’s good, she says yea. Worth every penny.

I still need lunch and have a few minutes before my appointment. I go in for a slice and in the pizza parlor bathroom start stripping down to find the lost condom.

There it is, in my shoe. It must have gone down my pants leg and ended up in my shoe.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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 felt great about this. Sex in the car was on my bucket list. I hope to see this girl again. She’s expressed a willingness to see me again. Also, she’s OK with videos and I want to explore that.

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, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? I don’t know

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’ve posted this on a couple of boards with good feedback.

I’ve thought of talking about this with my therapist but haven’t. I don’t think the details make that much of a difference.

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? Fun and adventure.

What was the WORST thing about this hookup? Not much bad.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not at all. I’ve been enthusiastic about casual sex and remain so!

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? Just a fun experience that I don’t want to forget!

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? I wish it was more socially accepted.

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

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