First Time With A Man



What’s your gender? Man
How old are you? 43
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Lawyer
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 70
How many hookup stories have you here posted before? 0

First Time With A Man

How long ago did this hookup happen? 7 years ago

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? I met him through Craigslist. I had been harboring a conflicted interest in giving a man a blowjob for some time, and would peruse the ads on Craigslist during down times at work. My interest usually quickly fizzled whenever I actually reached out to anyone, but this guy was different. He was attractive, fit, very straight/masculine sounding, and assertive. Had also had a good sized member, which fit into my fantasy.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We exchanged a couple of emails while I was at work. He explained he was also “straight”, but was interested in getting a blowjob from a man. Whenever I started to panic or hesitate about actually meeting up, he was good at assertively persuading me, telling me he knew this was what I really wanted, etc. I was just finishing up my work and he wrote insisting that we meet up that night, and that I give him my address. I wrote out my address on the screen. My heart was pounding and my head was spinning as I suddenly pressed send. He quickly replied, “Great, I’ll be there in an hour.” As I walked home, I felt like I was in a dream, and that everyone I walked by somehow knew what I was about to do.

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 downed a couple of large shots of vodka at home to quell my nerves. He arrived on time. My knees buckled a bit as I answered the door. I had brought a cushion over by the door thinking we would do it there for some reason. When he saw it he just laughed and pushed it out of the way. We walked over to the bed. After a minute of small talk, he gently pressed on my shoulders and told me to get on my knees while he pulled his shorts down. His large semi-flaccid dick was hanging right in front of my face now. In our email exchange I had insisted we use a condom, but my will gave way and I went straight to licking his dick. The taste didn’t bother me, as I feared it might. His dick instantly got hard after my tongue touched it. To my surprise, I seemed to know exactly what to do, licking his dick and balls while I grabbed his firm ass. I bobbed up and down on it, looking submissively up at him as he groaned in pleasure. After a few minutes he was on the verge of cumming and he grabbed the back of my head and started thrusting deep into the back of my throat, causing me to make a faint gagging sound, which I think we both enjoyed. He came hard into my mouth. It tasted salty and bitter. After he was done, I made a motion excusing myself to go spit in the sink. I wish I had had the guts to swallow, but I was afraid it would make me vomit. We chatted for a few minutes after that. He expressed an interest in doing it again sometime.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even 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? After he left, I felt proud of my accomplishment and texted him that he could come back for another round whenever he was free. He never got back to me, which made me feel a little cheap and, to be honest, turned me on even more. I tried to recreate that experience with a couple different guys, but it never measured up to that first experience.

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

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Somewhat

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? A couple of girlfriends after that. One reacted very positively and was turned on by it. For another, it raised red flags about my sexuality.

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Finally acting on a long time fantasy.

What was the WORST thing about this hookup? Only happened once. I would have liked to have experimented further with this man.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Although I identify myself as mostly hetro, this experience evidenced to me the fluidity of our sexual nature.

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? Once I became comfortable with it, I engaged I a lot of causal sex in my 20s and early 30s. I believe it was a necessary phase for me to go through to exorcise some demons and be able to eventually find contentment in a monogamous relationship.

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