What’s your gender? Man
How old are you? 47
What’s your race/ethnicity? Mixed / Multiracial
What continent do you live on? Australia
What country and/or city do you live in? Sydney
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Transport
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Enthusiastic!
How many sexual partners have you had in your life (including oral sex)? Around 50
How many hookup stories have you here posted before? 3

Outdoor sex with a working girl

How long ago did this hookup happen? A year ago

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? Her working name was Leigh, I have no idea of her real name. I was driving through a part of town where I knew street prostitutes hung out. It’s an area with truck stops and light industry. I saw her sitting on the curb at about 1 a.m. as I drove past. I wasn’t sure if she was working or just a drunk girl having a breather on her way home but I slowed down and lowered the passenger window and she got up and leaned in. She was kind of heavy set (I wouldn’t say overweight though) and I thought she was pretty. She had a nice smile and general demeanor.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I hadn’t really planned to pick up a girl that night. It was only the second time I’d ever picked up a working girl from the street, and my first time in that area. But when I decided to drive home that way I had a vague notion that if I did find someone I’d at least pay for a blowjob. So when Leigh got in and told me her rates (which I thought were reasonable) I told her I’d like a blowjob. She said “oh, I wanted sex!” which amused me but I stuck with the blowjob – at first!

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? I paid Leigh her money and she directed me to drive into a driveway of one of the light industrial complexes. It was deserted. I pulled out my dick and she put a condom on (with her mouth) and began to suck. Her mouth was lovely but the trouble was there were these stupid kids who’d been following her around and hassling her customers all night and they saw the car and pulled in up the driveway and turned on their lights. I wasn’t really worried about safety or being outed but I did lose my erection as a result of the distraction. She got really annoyed at the kids and got out to confront them but they took off like the cowards they were. When she got back in I asked her if she was okay. She was fine but annoyed that they’d interfered with her doing her job. We were getting on well by this time (we kind of bonded over the kids incident) so I asked her if I could pay the difference and upgrade to full sex. She was very enthusiastic, so I gave her the money and she directed me to drive to a cul de sac which was completely dark. We got out of the car, she lay in the back seat, I pulled down my pants and after she put another condom on me, I got on top of her.
Now there’s something about car sex – I’ve never been a fan. The angles are always awkward and I’m never comfortable so after a few minutes I asked her if she knew a place we could stretch out outdoors. She said yes, so we got back in the car, and she directed me to drive up the freeway towards town. We ended up in one of the inner suburbs, a quite built up area, coincidentally near one of the depots where I sometimes work. We stopped off at a block of flats where she said she had a blanket stashed in the basement but when she looked, she said the cleaners had thrown it out. But I have an old padded coat, thigh length, which I keep in the boot of the car in case I need to protect the paintwork when I’m shifting heavy stuff, so I told her not to worry. So we kept driving towards the local oval.
It was about 2:30 a.m. by the time we stopped. I got out the coat and spread it on the grass. It was Autumn and cool but not cold. She took off her shirt and bra and I sucked in her lovely breasts – they were large and firm. She pulled down her pants and lifted her skirt, I pulled my jeans and boxers down to my ankles and she put another condom on me and in I went.
She was lovely and warm and wet. I fucked her in the missionary position, then pulled out and she got on her side, and I lay behind her, rubbing my dick against her clit and cunt while caressing her gorgeous breasts with my other hand. Finally I felt my orgasm building and I shoved my dick deep in her cunt and just let go. I loved the feel of her plump buttocks against my crotch and thighs as I unloaded in her.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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? We lay there for a while, me still buried in her. Just us, semi naked, under the stars, in the middle of the suburbs. Like the high school experience I never had! A plane flew high overhead and disappeared into the black, I remember that. I looked at Leigh’s face, saw she was smiling and kissed her on the cheek. Eventually we pulled apart and I slipped the condom off, tied a knot in it and threw it into the bushes (the only part I regret – I should’ve looked for a bin). I ended up driving Leigh back to the place I found her, at her request. I hope she got more action that night and those stupid kids stopped bothering her.
I have no particular desire to see Leigh again. It was wonderful, almost magical, but it could so easily not have been. I’d rather have the memory of that moment than try to recreate it again. But I wish her all the best, I hope she’s still happy and safe.

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, Attraction to partner(s), Learning new things, experimenting, Thought it was an important experience to have, Just happened, I don’t know why, just went along with it, It was easy / convenient

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

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Marijuana, hashish

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? A couple of friends. My (male) FWB in fact. He was intrigued.

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? The whole experience. It felt like the kind of thing you do as a teenager when your life is ruled by hormones – only I never had that kind of experience as a teenager. So in a way it was like visiting a part of my youth that could or should have happened but didn’t. And within the bounds of a professional-client relationship, it was quite romantic.

What was the WORST thing about this hookup? Me throwing that condom into the bushes. I hate littering.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No not really. I’ve dealt with all that by now.

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? I’m generally not inclined to pick up street prostitites – I think brothels are much safer. Also I don’t like to exploit anyone who’s down on their luck. But Leigh was enthusiastic about her work (we talked a lot in the car), she wasn’t coerced, she didn’t have a pimp and she seemed happy with her life. If she hadn’t been I couldn’t have gone through with it.

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? Casual sex is a big part of my life. I wish it was more generally accepted. I also wish that people could see that having sex with a person outside of a relationship (I’m married) is not the worst betrayal. Where I work I am surrounded by middle aged men who trash talk their wives and call them bitches, etc. and make fun of them in nasty ways. Well, I may sleep around, but I have never put my partner down in public. I have never aired our private disagreements. I am always supportive of her and what is important to her in public and at home. I love her, it’s just we aren’t sexually on quite the same page. So I consider my casual flings a very small misdemeanour compared to the emotional betrayal I see going on around me.

What do you think about the Casual Sex Project? Greet! It lets me tell someone honestly about my life.

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