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What’s your gender? Man
How old are you? 58
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Communications
What’s your current relationship status? In a serious relationship (monogamous)
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? Heterosexual, do not like men, but like cocks
How many sexual partners have you had in your life (including oral sex)? 5
How many hookup stories have you here posted before? None

How I Learned I Was A Sissy Cocksucker

How long ago did this hookup happen? When I was in my teens

What was your relationship status at the time? Single

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 3 years

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? Nick was around 6 ft. tall, good looking, and slender. Slender. We were the same age.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at a British private school. No planning was involved on my part but my friend decided to seduce me.

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? I was a teenager and my friend Nick and I became very close, spending a lot of time together and laughing a lot. One day, we were in the music room in the basement. I was sitting in a chair and Nick sat on the arm. He started stroking my chest through my shirt. It felt good so I did not stop him. Slowly, his hand wandered lower. Then, he reached my trousers and he slipped under the beltline. It felt good. He undid my pants, lowered them down my legs, began stroking me just alongside the elastic of my underwear. I felt his fingers graze my penis and he began teasing it through the cotton. I didn’t want him to stop. He slipped my underwear down and my cock stood naked before him. Then, he lowered his head and put his lips around it and slid his mouth down. He moved his mouth up and down my shaft, sucking me. After a while he stopped.
A couple of weeks later, we were walking by the cricket field and I suggested we resume our activities. We went to an attic room. I told him it was my turn, I wanted to see his cock. I undid his pants and pulled them down with his underwear and his cock sprang out. It was only slightly smaller than mine and uncircumcised. I knelt between his legs and lowered my head over his cock and moved my mouth up and down, sucking. After a while, he wanted to stop. I was disappointed.
A few weeks later, we were down in the basement music room again. I got him to sit on the window ledge with his back to the window, so no one could tell what we were doing. I knelt between his legs and took out his penis and began sucking it again. After a while, I could tell he was getting excited as I moved my lips more quickly up and down his shaft. My mouth seemed to be filling with liquid. He wanted to stop. I wanted to continue. He insisted we stop.
A month later, we had a free study period. No one was around. Each boy had a cubicle, which consisted of a desk with a bench facing it and a cupboard on one side and a curtain on the other offering privacy. We were in Nick’s cubicle. Nick was sitting on the bench and I went underneath the desk between his knees. I lowered my head and slid my lips down to the base and then slowly withdrew up his shaft. Soon I was bobbing my head up and down much more quickly, swirling my tongue over his cock head, and tickling his slit. To my surprise, it suddenly started to flex and swell in my mouth. Thrilled, I began sucking urgently. I felt a blast of warm liquid hit the back of my throat and my mouth was overtaken by a pungent, salty taste. I stopped moving, took my mouth off his cock and held his cum in my mouth. Then I swallowed it. I felt so submissive and dirty.
That’s how I learned I was a sissy cocksucker.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was close

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 masturbated furiously. Turned on but somewhat compromised as I always thought I was straight. I wanted to do it over and over.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Learning new things, experimenting, Emotional intimacy, closeness, connection, Submission / Relinquishing power, Just happened, I don’t know why, just went along with it

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? Not at all

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? No one. Eventually my current partner. She is incredibly turned on by it.

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

Did you get emotionally hurt as a result of this hookup? Somewhat

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? It allowed my submissive side to come out and I got to suck cock and swallow sperm

What was the WORST thing about this hookup? It ended or friendship and intimacy and turned into a series of occasional sexual episodes

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It makes me very excited when I remember it and I wish I could relive the experience.

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

All things considered, how NEGATIVE was this experience? A little 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? I like the idea, but intimacy makes sex incredible. I need intimacy before I want sex.

What do you think about the Casual Sex Project? Very interesting

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