Filling All Holes



What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Insurance
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Filling all Holes

How long ago did this hookup happen? 2 weeks ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a month

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? Jen is a 29 year old woman, she is about 160cm, short red hair, green eyes. her figure is average, the boobs are rather small, her pussy is shaved. I did not consider the girl to be very pretty, but I really enjoyed her sexual energy.
She was a participant in a training that I did for a group of employees.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was tasked to do a training for a group of people in my company’s branch in Melbourne, Australia. It was the first time I was doing this training. Usually a colleague and friend of mine does this training, but he couldn’t do it this year, so it fell on me. This way I won two weeks in Australia, all by myself. I have been married for 8 years now and I have a five year old son. I wanted to use the opportunity for some extramarital sexual activity. I tried it with Tinder and also with chatting up women I met by random, but no luck.

After the last day of training, there is a dinner and drinks sponsored by the company. My friend who had done the training last year texted me that this was a great opportunity to pick up women. I had not thought of this option and cursed my stupidity that I had mentioned my son and wife during the training. That would certainly not make my attempts to fornicate easier. Still, I took off my wedding ring for the occasion and hoped for the best.

I noticed that Jen had always been a little bit flirty with me during the training. I had the impression that she liked me. So I chatted with her and got the impression that she was responsive. Towards the end of the dinner, I mentioned to her that I had not seen that much of Melbourne. Jen offered to show me around a bit. I took the clue, excused myself for a moment, went to the toilet and got some condoms from the vending machine. (Just in case we got really lucky!) Then I went to explore the city with Jen.

She took me to the Eureka tower skydeck, where I invited her to another drink. Jen got a bit giggly while we enjoyed the view over Melbourne from the 66th floor. Jen was nicely drunk which I hoped would improve my chances.

Then we went out for a stroll on Southbank. While we were walking along the Yarra River enjoying the sight of the skyscrapers, I thought it is now or never anyway and I reached for her hand. I was pleased that she accepted and we walked hand in hand for a bit. I noticed that we were actually walking towards my hotel, which I saw this as a stroke of luck. We stopped by the river and I kissed her. Jen stuck her tongue inside my mouth and we started making out, leaning against a concrete railing. Jen was wearing a short dress. I felt up her legs and got my hand into her undies. I slid a finger inside her pussy. Jen softly moaned into my ears as she was leaning against me and I was fingering her.

I mentioned that my hotel was not far away. Jen understood and we went to my room.

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? Jen got naked pretty much as soon as we entered the room. She seemed to be as keen on sex as I was. She had a lot of sexual energy, her lustfulness was intense. Our fuck session lasted for hours. We had quite an extensive foreplay. I licked Jen’s nipples, her pussy, her arsehole and even her toes. There was a little bit of a footjob and most of all, Jen gave me oral for a very long time. I even fucked her mouth for a bit, but gently. I did not want to put her off by attempting a deepthroat. Jen did not seem to mind.

Jen rode me like a cow girl gone crazy screaming out her lust. We changed position several times and I ejaculated while we were doing it doggy style. I had noticed that Jen frequently massaged her clit while I was fucking her. This made me feel a bit insecure because I wondered whether I was doing her well enough. But then I realized that I was enjoying myself, she was obviously having a good time, so who cares.

After the first round of sex. Jen got up and plundered the mini bar. I thought this was great as it would keep her drunk enough to want to have more sex with me. She drank the mini bottle of wine and I had the can of beer. Jen went to the toilet and came back to the bedroom with a little plastic packet of soap. She mentioned that those are perfect for anal sex. I was all ears and asked her whether she wanted me to stick my penis into her arse. Jen was up for it.

Jen got my pecker up again with a round of 69. I was massaging her clit while licking her arsehole. I opened the package of fluid soap and lubed her anus with it. When I felt I was stiff enough I put on the condom and slowly pushed my way inside Jen’s anus doggy style. She moaned and massaged her clit while I was fucking her from behind. I was already a bit exhausted from all this fucking so Jen came way before me by masturbation and I stopped fucking and took of the condom without having ejaculated. I took off the condom and masturbated while Jen was sucking on my balls and occasionally putting my penis into her mouth. It took a while until I finally ejaculated on Jen’s breasts.

We kissed and talked for a bit after this long sex session, but Jen did not want to stay with me in the hotel. It was already late at night so I offered Jen to give her money for a taxi, which she readily accepted. Before she left, she teased me that I would obviously not tell my wife about this experience in Melbourne.

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? It was the perfect One night stand. Jen’s last comment about my wife made it clear that she knew all the time that I am married and this would be a one-off encounter. We both (at least I hope so) had enoyed the sex and that is it. I don’t know whether I will ever see her again and if I do, whether we will have sex 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, To feel better about myself, To feel more desirable, To feel more confident

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

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? I don’t know / I’m not sure

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 told my work friend about my sex adventure and we realised that he had fucked the same woman last year. She really seems to be into casual sex. We laughed a bit awkwardly when we learned that we both now share having had the same sex partner. A bit odd, but not a real problem. She lives on the other side of the world.

How would you best summarize people’s reactions about this hookup? Neutral

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? I have been monogamous for many years and it was great to have sex with someone else, with a stranger. Jen may not be very pretty, but her lustfulness was amazing and made this encounter a great experience. She was so open to do anything.

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I was happy to have found a sex partner who seemed to have enjoyed her time with me. This raises my hopes for future extramaritial sex adventures.

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? Monogamy is not for me, I need to cheat on my wife from time to time. I wonder whether monogamy is good for anyone.

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 I could talk to my wife about my and her needs. It is a shame that once you have a family, casual sex needs to be kept as a dirty secret.

What do you think about the Casual Sex Project? I read the stories and envy the guys who get to fuck all the time.

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