What’s your gender? Man
How old are you? 57
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Writer
What’s your current relationship status? Single
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Cross dresser
How many sexual partners have you had in your life (including oral sex)? 8
How many hookup stories have you here posted before? 1

Sissy Suck Off

How long ago did this hookup happen? This week

What was your relationship status at the time? Single

How would you best classify this hookup? Paid sex

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? This guy was a thick young jock. Massive thighs. Average height. Nice face. Small nose. Huge, beautiful circumcised cock

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I paid a shemale escort for a session and she arranged for him to join us because she said she wanted to see me suck cock and I said I wanted to because I had only sucked one other cock before: my friend at school

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 have very long hair and I was wearing panties and a bra with breast forms under an open button up white shirt. My shemale friend put lipstick on my and eye shadow. My shemale friend went between the guy’s legs and got him hard, then told me to suck him. I got down on my knees and found myself staring a huge, beautiful uncircumcised cock straight in the eye. I resolved to suck it off.
I lowered my mouth onto it and slid my lips right down it. And slowly, lovingly slid my mouth up and down his large shaft for a couple of minutes. Then I opened my throat and tilted my head a little and tried to deepthroat him. I got most of it in and he started to let out the occasional sigh and moan. I moved back to sucking him and went at it faster, then slower. Sometimes I took it out and wiped his Vick head across my lips and small, pert, girly nose. While I was sucking him, he would hold up my hair in his hands to make it easier. And sometimes he would put his hand on the back of my head to pul me closer and encourage me. After sucking him for several minutes and listening to him groan, I decided to take a break as he did not seem too close to coming.
We sat, me in the middle, my shemale friend to my left and the jock to my right. His cock was huge and needy, so I spat in my hand, reached out and started jerking him lightly but fast. To my surprise, he really liked that. I could tell he was excited, so I got back down on my knees between his legs and took his shaft in my mouth and bobbed up and down on it quickly, alternating between sucking him and giving him an urgent hand job. I could tell he was very excited and sure enough when I went back down on him, he said in a sighing voice ‘I’m gonna cum!’ So I made my lips soft and slid my lips up and down his twitching cock quickly. Just then I felt drops of sperm spray into my mouth and more and more liquid enter it. I kept a steady, loving pace up for a couple of minutes as I took all the sperm out of his heavy balls into my mouth. He came for a long time. Then I gently slowed down, cane off him and swallowed.

How sexually satisfying was this hookup? Very

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

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? He went to the bathroom upstairs for a long time. My shemale friend and I started to worry. Then he came back down and left. I lay back in my chair faint with pleasure, vibrating with excitement, dying to come, jerking myself. My shemale friend saw this and said ‘Don’t come! Don’t come!’

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Discussed STI testing history

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, Submission / Relinquishing power

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol, Cocaine

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? 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 talked to my shemale friend. She said she wanted to see him in me and wished I sat on him. She said his cock was huge and beautiful. I agreed. She wanted to know if he came a lot. She said I was such a slut. She knows what I want to hear

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

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? Sucking his massive, beautiful cock. Hearing his sighs and moans. Having him hold my hair up and encourage me to suck him. Feeling him ejaculate in my mouth. Having a mouthful of his sperm. Swallowing it. Feeling like a dirty, submissive slut

What was the WORST thing about this hookup? I wondered if he was attracted to me

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I alway thought I was a sissy slug. Now I know I am. I daydream about his cock and sucking him off. I want to see him again

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? Get to know yourself!

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 am very glad I did this

What do you think about the Casual Sex Project? It is fascinating

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