Casual Sex, Finally!



What’s your gender? Man
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Italy
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Master Degree student
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? I’ve long desired starting experimenting and living a meaningful sexual life, this is my first experience as such.
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0

Casual Sex, Finally!

How long ago did this hookup happen? 3 days ago

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

How would you best classify this hookup? Short fling

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? T. is a non-binary, female-presenting, male person about my age. Since I was curious about trying dick, I swiped right on their cute Tinder profile last summer and, much to my surprise, I was reciprocated! We texted and exchanged butt and dick pics (I shaved my butt to be sexier for both of us), but we weren’t able to meet for a few months. While I thought they were very cute and attractive (I was right) I was worried about my physical appearance, as well as anything that can be of concern about your first casual sex experience: what if I don’t like them? What if it’s all a scam or whatever? What if I get some STIs or STDs? Overall, we didn’t talk much about ourselves so I didn’t know much of them before actually meeting.
We’d been planning an escapade for about 3-4 weeks, but we were so busy and tired all the time that we only managed to actually plan it the night before – but everything was fine. We decided to spend a weekend in a B&B in front of a lake and visit a cultural attraction the next day, taking advantage of the low season.
T. is a bit short and chubby, with fair skin and beautiful black eyes and hair. They shave their whole body, dress in a feminine fashion and pay great attention to their make up. I absolutely loved their buttery, androgine body and especially their wonderful ass.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Not long after closing the room door behind us we started cuddling and making out, with T. being the initiator: I am quite shy and always paranoid about consent and whatnot, while T. is more of an active person, especially in bed. It was already clear that we were going to be intimate and that I was going to be penetrated, that was the whole point of us meeting.

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? We started playing with each others’ bodies quite soon: I focused more on stroking and sucking my lover’s cock, while they mostly enjoyed fingering and rimming my ass. T. loved having me facesitting on them and diving in my butthole with their tongue, while I discovered the joy of getting facefucked by a caring lover – I preferred not to try to deepthroat their penis, though. Of course, we helped ourselves stroking our own penises when the other could not. The whole time I was more passive and T. more active, but it was never brutal or forced; instead, everything was very natural and harmonious.
We spent so long doing this that we had dinner very late, and we took a detour to get condoms and lube.
When we got back to our accommodation we started having oral sex again, and we finally tried anal. Unfortunately, my asshole is very tight, contracted and not particularly sensitive (I even had a fissure a couple of years ago): this meant that, besides some great moments during facesitting, it didn’t give me much pleasure, and the penetration was uncomfortable and painful, even after using an anal dilator; my partner, then, agreed to stop as soon as I told them, and the whole penetration didn’t probably last more than two minutes. It was a bit disappointing for me, but T. reassured me it was no problem and it didn’t take long before we started hugging, kissing, cuddling and having wonderful oral sex again.
We started sleeping very late, and when we woke up we fucked this way even more. I don’t remember if we fucked after breakfast too, but anyway it ended when we had to free the room.

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? The next day we had a tasty breakfast in the B&B and checked out, and we went to visit the cultural attraction I mentioned before. The experience was wonderful and I remember it fondly; My escapade partner and I have become very intimate and we hope to meet and fuck again, but I’m a bit dubious about my ass; I’ll maybe see a doctor to see if there’s anything wrong with it, and I maybe will try to train it and see if it gives me pleasure.

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, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely

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

How intoxicated was your partner? Not at all (no alcohol or drugs)

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 didn’t tell anybody about this hookup, but maybe I’ll tell my friends or my family if the topic comes up or if I feel comfortable with that.

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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? Getting intimate with a loving, caring and interesting person, feeling appreciated and sexy.

What was the WORST thing about this hookup? Finding out that my asshole is difficult to fuck; that’s pretty much the only negative thing about those two days

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really, it just gave me the confirmation of what I was already thinking: having sex, relationships, experiences is broadly speaking good and positive, and I should do it more, worry less and be a bit more crazy in life.

All things considered, how POSITIVE was this experience? Very positive

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

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? In general I’m under the impression that people should fuck more, and that anyone should fuck as much as they want without feeling judged or having to hide it. I also think that this is a period of crisis for men who, very broadly speaking, must reinvent and rediscover themselves and learn how to approach partners. I mean, it’s no surprise women are so uptight and choosy about men, right?
Knowing this has always made me very anxious about dating, and that’s why I’ve only had one relationship in my life and had never had casual sex before; this episode has given me hope about myself, my ability to enjoy life and to be a good person to others, and how attractive my butt is.

What do you think about the Casual Sex Project? It’s… interesting, to say the least? I hope the data are good and unbiased enough to find meaningful answers and questions

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