First Time With A Male

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Somewhat
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 3

First Time With A Male

How long ago did this hookup happen? 10 years

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For less than a week

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? I was curious about my feelings toward men. I had played with my ass some and had used some small dildos to penetrate myself, but I wanted to see what a cock felt like in my mouth and ass. I started searching for a site for males to hook up and found one that sounded right. I posted a profile and got several responses, but none of them could host and I couldn’t either. I finally got one response from a guy I’ll call C, that said he was a total bottom and that he loved to suck cock and balls. I sent him a message and we were soon chatting and talking on the phone. We planned a hookup for the next day. I went to his house. He was about 20 years older and seemed to be fit. He greeted me at the door naked and suggested I get undressed and join him in bed.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I got undressed and sat on the bed with him. I have a reasonably large cock at 7 1/2 inches and thick, but even soft he was big. Much bigger than me. He told me he had surgery to remove his prostate and could not get hard. In a way, I was happy because I didn’t want him shoving that coke can up my ass since I had only used small dildos on my self.

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 had told him over the phone what I expected from the hookup: a good blow job with ball sucking, at least a finger in my ass, and maybe some prostate stimulation. He had told me that he just wanted me to fuck his ass.
He told me to lay back and spread my legs. He climbed between my legs and began fondling my cock and balls, following his fingers with his lips until he started licking my balls. He worked his way down to my ass, rimming me and then working his tongue into my ass. He played with my cock and balls as he licked my ass. He then moved to my balls, sucking the first one and then the other into his mouth while he stroked my cock with one hand and inserted a finger into my ass. I was enjoying his attention and then he moved his mouth to the head of my cock and took all of me into his mouth and down his throat. He was playing with my ass as he sucked and stroked my cock, getting closer and then backing off and then closer again. Finally, he got me too close and even though he backed off, I told him I was going to cum. He sucked me back in and I came a ton as he swallowed it all. He continued to suck on me as I went soft. We relaxed a bit and had some water.
I wanted to play with his large cock even though he said he couldn’t get hard. I said that was okay, I just enter to play. I took his big cock in my hand and felt the weight of it. Then I took his balls in my other hand. I leaned over and sucked his head into my mouth. He was so big I could only take his head in. I ran my tongue over his cock and then sucked on his big balls. I had him play with my cock while I sucked on his limp cock. He finally got me hard again. He handed me the lube, laid on his back, and spread his legs. I lubed him up, spread the lube on my cock, and asked how he wanted it. He said shove it all in now, so that’s what I did. He was tight and I enjoyed his tight ass pulling at my cock as I reamed it. It took a while for me to cum, and when I did, I didn’t think I would ever stop. I kept stroking his ass as I came inside of him.
We finally got up, showered, got dressed, and I went home.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? I don’t know

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 got together several more times over the next year until he moved away.

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

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

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? None

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? Great first time male male sex.

What was the WORST thing about this hookup? Nothing.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Open to more mm sex.

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? Casual sex is great as long as every one involved is on board.

What do you think about the Casual Sex Project? Splendid.

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