First And Only Time

by JD

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Virginia
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Executive
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Horny all the time
How many sexual partners have you had in your life (including oral sex)? 40
How many hookup stories have you here posted before? 2

First And Only Time

How long ago did this hookup happen? 7 years ago

What was your relationship status at the time? Same as current status

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? He was a white male. I never got his name and didn’t really want to know it either. He was clean cut and well dressed in his work clothes. He was a white collar professional type, clean shaven, with dirty blond hair. I didn’t look too close as I wasn’t eager for too much eye contact. I had just met him that day through Craigslist.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I loved to cruise Craigslist for women and had decent success. One day my female prospect bailed and I was just so horny with my only desire a blowjob. I decided to check out an ad of a “straight” guy just looking to suck. I was way too horny so I replied and began chatting. He seemed laid back and I agreed to let him come to my house after work. He would walk in, suck me, and leave. I couldn’t believe I was doing this, but I was always curious if a guy could suck better since they know firsthand what feels good. He was persistent and I was thinking with the bulge in my pants.

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? As planned, he parked on my street and walked to the door and, as instructed, he walked right in. I was on my couch in the front room in basketball shorts and t-shirt. We said hey and he walked over and sat next to me without speaking. He swallowed his saliva, took a nervous deep breath, and pulled my shorts and boxers to my ankles. I was surprisingly rock hard and had my usual sexual fervor going. I hadn’t come in days and purposely edged before he got there so I would cum easily. He lowered his head and rubbed his tongue all over my shaft as he took me all the way in. Damn, it really felt good, and I closed my eyes and let him work. It wasn’t long though. After about 10 pumps, I could feel that huge load coming. He didn’t sense this and took me out of his throat to catch his breath and I proceeded to spurt my load all over his chin and all over my couch and body. I stayed silent and he wiped his chin and said thanks and he left. I cleaned up and it turned out my female friend was available. I fucked her later and now realize I should be more patient.

How sexually satisfying was this hookup? A little

Did you have an orgasm? Yes, one

Did your partner have an orgasm? No

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? The bj felt great and I came hard, but I’m really not that into guys so if felt like a curiosity. He messaged still wanting to get together again, but I will really have to be horny again to go down that path. I prefer cumming on tits and a pretty face.

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

What were your motives for this hookup? Thought it was an important experience to have, Boredom, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Marijuana, hashish

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? Nobody. Just here.

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? Somewhat

Why do you regret this hookup? I felt dirty after and realized it wasn’t my jam.

What was the BEST thing about this hookup? Cumming on his chin and his surprised look/grin.

What was the WORST thing about this hookup? It was a dude and not a woman. I could have shot that load on Lindsey’s face instead.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope. Was still kind of cool and now I know.

All things considered, how POSITIVE was this experience? A little positive.

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? Love it and wish there were more.

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