The Kinkiest Sex Of My Life



What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Belgium
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Businessman
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 14
How many hookup stories have you here posted before? 0

The Kinkiest Sex Of My Life

How long ago did this hookup happen? Two years

What was your relationship status at the time? Engaged/Married (monogamous)

How would you best classify this hookup? Paid sex

How long did you know the person before this hookup? For less than 6 months

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 met Kira on a sugar daddy website; she is based in London and I visit there often. She is Eastern European, with a few extra pounds as they say. We exchanged a lot of sexy texts and she sent some very explicit photographs and videos. Her proposed rate of pocket money for a date was more than my budget usually reaches to. But I found her level of sexual energy both fascinating and a little intimidating.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We actually had a missed connection to begin with. We had arranged to meet up in London one evening but she simply didn’t show, no reply to texts or anything. I shrugged with disappointment and put it down to experience. But a few weeks later she got back in touch and explained that there had been a family emergency that night; could she make it up to me some time? So we agreed to meet at Leicester Square one evening when I was visiting London.

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 insisted on buying some booze (vodka and tonic in a can) and we went back to my hotel. As soon as I had given her her pocket money, she started by giving me the best blowjob of all time, with the cold booze in her mouth dribbling down my cock, as I filmed her on her phone. Then she climbed on top of me and rode me till we both came.

We took a break for a Chinese meal and then went back to my room for another go. This time I took her from behind, and moved to fucking her ass when she asked me. She came again but I couldn’t quite finish.

We lay back and caught our breaths, curled up together, her back to me. I realized I was getting hard again and eased myself into her. She said, “You know you’re in my ass? Stay there a moment” and reached for her big vibrator which she worked into her pussy. The vibrations through her body were amazing to feel as I thrust into her ass with the vibrator deep inside her. Eventually I came again.

But she wasn’t finished yet! As I slid softening out of her ass, she reached for a packet of lube from her bag and asked me to fist her. I’d never done that before; but I smeared it all over my hand and started to fuck her tight hole with my clenched fist. She gasped and screamed and soon came again, her vaginal walls pulsing around my hand.

It is the kinkiest sex I have ever had.

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? I got her an Uber back to her station after midnight, and decided that although it had been amazing sex I wasn’t desperate to repeat the experience – it was a little overwhelming.

I stayed in touch with Kira on Facebook, but did not insist on another meetup. A bit more than a year later I saw that she had had a baby. We send each other friendly greetings from time to time but I don’t feel I especially need to see her again.

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

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? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Somewhat

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 have told a few of my other lovers about it. They were amazed by Kira’s kinks.

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Having anal sex with Kira while her vibrator was deep in her pussy.

What was the WORST thing about this hookup? I would have liked to go on longer, and she was willing to stay the night, but I had stupidly made breakfast plans for the next morning so it wasn’t possible.

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? Fairly positive

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

Anything else you want to add about this hookup? It was one of a number of hookups I have arranged through the sugar daddy site. They take a dim view of effectively being used as an escort agency; I feel that it’s fine because we were both open to making it a longer term arrangement, although in the end that was not what happened.

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 am a late comer to casual sex, but I very much enjoy it as an intense and cathartic physical activity.

What do you think about the Casual Sex Project? A great idea. Inspires reflection as well as arousal.

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