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What’s your gender? Man
How old are you? 36
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? US – Washington DC
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Agnostic
How religious are you? Not at all
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? 5

Random Gay College Grad Romp

How long ago did this hookup happen? Just Today

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? Jerry was a 24 year old college grad student who I met on Squirt. We shared pictures and from his description and photos he was 5’8″ and portly weighing about 50 pounds on top of my chubby 190 @ 5’9″. He was a 2nd generation Indian American (i.e. from India) and had an uncut cock that was about 5″ long and average thickness. He was untrimmed down below and had furry legs but a smooth chest and back.

He contacted me the night before wanting to hook-up. I have a rule that if I am will to cruise online, I can wait until the next day to see if I still feel like I want to hook up. I chat with him and decide that we could hook-up tomorrow. We had sex chat and I jerked off to thoughts of him fucking me the next day.

He reached out after his interview the next day and I decide that I do want to have sex with him and ask him to come over.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Jerry came to my apartment and I went down to meet him. He is exactly as his pictures showed him and he had the most adorable smile. We went upstairs and I could tell he was a bit nervous about meeting, but he was definitely enthusiastic. I asked if he needed anything and he said no and we decided to just go to the bedroom and get the party started.

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? In the bedroom, we awkwardly came together and rubbed on each other. At this point, as much as he called himself a Dom Top online, he was anything but. He was awkward and reminded me of myself some years back when I was just figuring out my sexuality and starting random hook-ups. We kissed a bit as we stripped each other of our shirts and proceeded to take of our own pants and socks off until we were in our underwear (him long boxer briefs and me a jock strap). We let our hard-ons rub against each other and continued kissing and rubbing each other’s bodies.

Jerry reached and grabbed my ass and rubbed my crack and hooked his fingers in my jock and pulled it down, allowing my 6″ hard cut cock to spring out. He grabbed a hold of it and said how beautiful I am. I laid down on the bed and he lowered his mouth onto my cock. He sucked on the head and quickly worked all the way down my shaft, deep throating me. I was moaning up a storm and leaking so much it caused him to pull off and cough. I asked to switch and he stood up and I pulled down his boxer briefs and his cock sprung out with an upward curve. His foreskin was tight up against his head and the tip of his glans was poking out.

I grab hold and pull on his foreskin and he moans. I push him back on the bed and proceed to give him a blowjob, easily taking his size into my mouth and just touching the back of my throat. I sucked him and played with his balls for about five minutes before switching positions to where he could play with my ass while I blew him. I had put a dab of lube on my clean ass and he proceeded to finger me while I sucked on him. After a couple of minutes of him fingering me, I asked him if he would fuck me, and he agreed. We discussed barebacking and shared history. He was recently tested and hadn’t had any anal sex in a year. I haven’t had sex since the last time I was tested.

We agreed to fuck without protection and he requested that I ride him. Given his size, this was the better option for us to fit together. I climbed on top of him and grabbed a bottle of poppers and took a big whiff before plunging down on his cock. It felt fantastic having his fleshy tip penetrate my ass and slide up inside of me. I started settling down when Jerry had a look on his face and said to stop moving and as I did, he said he was almost going to cum. I didn’t want to get him off too quickly, so I held still for about a minute. I slowly started riding him and stopped another 15 seconds later. I did this a few more times and in-between take another hit of poppers and let my mind melt with ecstasy. I started riding him again and he said “oh god, not yet” and I pushed all the way down on his cock knowing he was going to cum. I felt him become larger and then started sliding up and down on his cock, milking every drop of cum as he was moaning. I rode him for another minute jacking my cock.

I finally stopped riding and just settled in on his cock. He apologized for cumming so fast and I said it’s alright. I pulled up off him and felt his load run down my thigh. I wiped it up and he grabbed ahold of my cock and started jacking me. I ask him if he would blow me and he agreed. I laid back and he started going to town on cock, but hesitated more than before. I called this the after-humming jitters where the sexual experience isn’t quite as fun as it was before. I took a hit of poppers and let him suck me for a while until he gagged and I could tell he wanted to stop. I took over and jacked my cock and asked him to finger my ass, which he did. I finally erupted my load a coup of minutes later.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? Yes, one

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? We basically wiped up and then got dressed and he left a few minutes later.

I was disappointed that he had cum so fast and also didn’t make me finish, but overall I would rather service a guy then get serviced so I was happy. I did slightly regret that I didn’t use protection, but based on our conversation and his mannerisms of shyness and basically new to sex, I felt safe.

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? Fun, pleasure, horniness

How intoxicated were you? A little tipsy/high

What substances did you consume? Marijuana, hashish, Poppers (Amyl Nitrate)

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? No One

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? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I am engaged and cheated on my fiancé. She knows I am bi (and about some past exploits) and doesn’t enjoy oral sex (giving or getting) and can’t do anal sex because of IBS. She also doesn’t play with my ass, which we previously had but has since stopped. She knows that she is leaving me somewhat high-and-dry at times, but I won’t tell her about this experience.

What was the BEST thing about this hookup? Sucking on a foreskin again and pleasing someone while getting anal sex.

What was the WORST thing about this hookup? Partner cumming too quickly for us to get a better experience.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? No change. Still enjoy sex.

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

All things considered, how NEGATIVE was this experience? A little negative

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