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What’s your gender? Man
How old are you? 23
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? Mexico City
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Historian
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? A little
What’s your sexual orientation? Gay/lesbian
How many sexual partners have you had in your life (including oral sex)? 30
How many hookup stories have you here posted before? None

Venice Hook Up

How long ago did this hookup happen? 2015

What was your relationship status at the time? Single

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

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? He was 50 by the time it happened. A 6’1 Caucasian man, bald and with a gray goatee. He was muscular. We met on Grindr the day before and chatted for a while before he asked me out. Because he had a blurry picture and no data on his profile, I wasn’t feeling super excited for the event. I accepted to meet him after another guy made a last minute cancel.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I lived for a couple of months in Venice and lived close to the Grand Canal. I told him to meet me outside the Gallerie dell’Accademia. I wasn’t feeling particularly attracted to that guy at that moment, so I thought it would be nice if I’d just greet him and make some cardio after that. I wore a pair of tights and a tee and waited for him at the top of the bridge. He hopped off from a vaporetto a few minutes later.
I felt so horny the minute I saw him. He told me I looked better than in the pictures. We talked for about an hour. He spent a couple of days in town for business on his way back to New York. We went to Zattere, the waterfront that overlooks the Giudecca Channel and strolled for about an hour until we reach a dock and kissed me. He pulled my waist towards his and I could feel his dick was getting harder while his fingers were trying to get inside the tights. the moon was full and its lights reflected over the water. It simply couldn’t get better.

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 went to his hotel and showed me his room. I was enjoying the view from the window when I felt his thick cock on my ass. He started to undress me and told me I was a very hot and handsome person. I felt very confident; couldn’t believe I was spending the night with hung like him. He kissed me fiercely and leaded me to his bed. I pulled of his shirt and started to kiss his nipples. His chest was big, hairy and fit, along with his arms and ass.
I was feeling a bit anxious since I only had outercourse before. Also because it was the very first time I dated a man as old as him. When I told him no one had penetrated me before, he simply knew what to do: he was so gentle and cautious it didn’t hurt me at all. While we were fucking he asked me if I liked the feeling of having his thick cock over my tight ass. That made me feel even hornier. I still remember what that man gave me as one of the most intense and rewarding experiences I’ve ever had.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 chatted on Grindr the day after that. I was feeling surprisingly good: confident, handsome and full of energy. I’ve never had any kind of reject or guilt considering the fact that I was first penetrated by a stranger.
The day before we chatted on Grindr for a while. Even though he told me he had an amazing night, he couldn’t see me one time during his trip. A few days later I asked for his Facebook account but he never replied to my message. Guess he just gave excuses for he wasn’t interested in repeating the experience.

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, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up

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 talked about it with several friends, especially girls. I don’t think they really understand why I feel so attracted to older men and even told me that was a little bit disgusting. Most of them told me I’ve got a sort of unresolved daddy issue and they even suggested me to get some therapy. My gay friends felt a bit jealous on the other hand, asking me for every detail.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

Did you get emotionally hurt as a result of this hookup? A little bit

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? The painless penetration and my hands grabbing the man’s ass while we were on our way to orgasm. That man really made me see the stars.

We cuddled after we were done. While he hugged me I could feel his chest and beard on my back. He told me I looked like an angel to him. It was very romantic.

What was the WORST thing about this hookup? Sex with this man was physically and emotionally fulfilling, so I started to started to have a crush on him, even after he stopped texting me.

Dealing with the fact that I might just be another one-night stand on his list.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I’ve dated with several older men after that experience. Even though I do feel sexually and emotionally attracted to people from my age, somehow I end up dating and sleeping with older men. They also find me very attractive.
I sometimes see myself having a relationship with a man who is decades older than me, but I’ve got the feeling that the society where I live wouldn’t have a positive reaction on that. No one from my family knows about this. Guess that a gay artsy who dates old men is still quite shocking in a country like Mexico, so I have to be discreet on that aspect.
People who find out about this experience have given me a wide perspective on this aspect. I don’t think the age gap should be considered for this particular situation, but most of the people I’ve talked about this find it disturbing.
There’s been some friends who have told me that my parents’ divorce during my early childhood. I feel bothered when people try to take my taste on mature men to an unconscious level as if it would be only one worth to analyze. Yes, I like to have sex with older guys. No, I don’t have a crush on my dad.

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

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? It’s been a year and I’ve masturbated thinking about what happened that night many times.

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’ve been in the closet for several years. I consider myself as a very sexual being and not exploring that realm was making me feel upset, frustrated and a tad depressed. Gay apps were a helpful platform for meeting guys who were also looking for fun. Even though I use them frequently, I’m trying to get rid of them because I’d like to work on my gaydar rather than depending on a phone for meeting new people.
Casual sex made me realize there’s a world outside my stiff, sexually repressed community. It has enabled me to meet guys with different ways of thinking and expand the way I perceive human interaction. But it has also being a harmful thing to do, for I’ve had strong feelings for guys who were interested in my body and nothing else. I think I have a wider perception on how the gay world works now.

What do you think about the Casual Sex Project? It’s liberating. I’m excited to share my sex tales with people who might have similar questions and struggles.

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