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What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Student
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Gay/lesbian
Any other term(s) that describe your sexuality or sexual identity? Passive
How many sexual partners have you had in your life (including oral sex)? 60+
How many hookup stories have you here posted before? 0

Daddy Issue

How long ago did this hookup happen? 1 month

What was your relationship status at the time? In a relationship (monogamous)

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? During one of my travels, I was activity searching for men over 40 on one of the gay dating websites. I found a man: 45, tall, handsome, well built and with a big cut cock and big balls. He was exactly what I was looking for. We decided to meet up in a cafe to have a coffee once I am in his country and see how things will go from there. We chatted quite often for a week or more before we met. Nothing sexual but more of “how is life?” small talk.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The day came and I arrived first to the cafe and waited for him. I was quite nervous and did not know what to expect or if I should go ahead. A couple of minutes later he arrived. As I expected: tall, mature looking, well dressed and sexy. I got so horny once I was him and wished we were already alone and naked. We started talking and for two hours or so, our conversation went back and forth between politics and local history. Did I say I am a nerd? I am gay and a nerdy guy. However, I do not seem like either. Once we drank our coffee, he said if I am interested in joining him home. I gave an enthusiastic YES!.

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? Once we got his place and took off our coats he kissed me. We kissed passionately in the hallway and I sucked his tongue and he gave a happy moan. He kept grabbing my ass and kissing me harder and grabbing my nipples, which made so horny. He took down my pants and grabbed my balls and cock with his big hands and kissed me even more. Then he took some spit on index and middle and they went under my balls and found my hole. He started rubbing it. Then said with a smirk that I am very tight and that he will enjoy it.

I took down his pants and started licking and sucking his balls. They filled my mouth and he was groaning. Then I began to suck him and massage his penis while doing so. He became even more excited and got me to stand up and shoved me towards the bedroom, only to stop me half way push my chest and face twards the wall while grabbing my hair with one hand and fingering my hole. I felt his penis on my ass and wanted him to fuck me so bad.

We arrived to the bedroom and he pushed me on the bed. We started kissing and we we held each other and kissed for some time. He started to smell sweaty and it turned me on even more. I started to alternate between sucking his dick and rimming him. He loved it and he he loved it even more when I looked at him while doing it. His cock and his hole were delicious. He would stop me every now and then because he was getting close. He would put me on my back and take my knees to my head and rim me so hard. Overtime I sucked him and rimmed him I did with so much passion because I waned him to be close and flip me on my back to rim me.

We started using some poppers and started rubbing his penis on my hole. I knew he wanted to go in bare and I wanted it. I wanted his huge cock and his warm load inside of me. While he was rubbing his cock went a bit in. At that point all the times I had taken STD and HIV tests and had waited for results flashed in front of my eyes. So I asked him to put on a condom.

I was very tight and it took several attemps before he could get it in. With the help of poppers it did not hurt much. We settled on doggy as the easiest way. He went in and started fucking me so hard. I was so into him that I kept on kissing him and sucking his tongue most of the time. He loved it. He would offer his tongue to and I would suck it and kiss him while squeezing his cock with my anal muscles. Loved to hear his moans. The more I squeezed his cock the harder he fucked the more I kissed him.

He turned me on my back and went between my legs. The way his cock made its way in was amazing. He saw I liked it and he kept on taking his cock out, spitting on it and then thrusting in. I would put my hand on his firm stomach while he did that and kiss his arms and hands. I worshipped every piece of his body. It was worth worshipping.

I felt something building up inside of me. I was about to cum. The build up was taking a long time. I did not touch my self and I have never experienced anything like it. Once it was reaching critical levels I put my self up and said he should be careful because I am close. I saw his face expression go wild. He gave me his tongue to suck for a bit and then push me back and started fucking me harder and harder. The build up was immense and then it came. The longest and strongest orgasm I have ever had. I could not breath and once I was done he took out his cock and covered me with his warm cum.

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? Once we were done we cuddled for a bit and continued talking about politics. I had to go but I think he wanted me to stay. But I could not.

I would like to tell him that the sex we had was the best sex of my life. But he will never know.

It feels bad to cheat on my partner but this need to meet older men is strong and takes over.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms, Discussed STI testing history

What were your motives for this hookup? Emotional intimacy, closeness, connection, To feel better about myself, Submission / Relinquishing power

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? No one

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? 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? A little bit

Why do you regret this hookup? I regret doing it. But I also regret not letting him fuck me bare and emptying his load inside of me.

What was the BEST thing about this hookup? The fact that I got appreciated by an older man. He wanted me, he enjoyed me, he used me, he gave me all his attention and devoted himself to me.

What was the WORST thing about this hookup? That I cheated on my partner.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It got me to realize that I do have daddy issues and need to be liked and approved by older men through sex. That does not make my attraction to older men unnatural or something to be worried about. I need to understand it more.

I should be more honest with my partner about this and maybe he will understand…

All things considered, how POSITIVE was this experience? Fairly 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? Some of the best people in my life are a result of casual hookups.

What do you think about the Casual Sex Project? It is a great platform to see how others relate to casual sex.

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