by Tgroan

Gender: Male
Age: 39
Race/ethnicity: Caucasian
Current location: NJ
Highest education received: College degree (eg., BA, BS)
Occupation: Manager
Relationship status: Married
Religious affiliation: Independent
How religious are you? A little
Sexual orientation: Bisexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 0

1st Time With Another Man

How long ago did this hookup happen? 11 years ago

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Casual internet hook-up

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 “Timmy” via a casual sex site for gay men.  He messaged me and we met in a public place for the first time to eye each other up.  He was handsome and about 10 years older than me.  Average build and black hair.  I was a bit nervous about the encounter initially, but followed him back to his car and then to his hotel room in something of a trance.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It began at a local open air market.  I was waiting for him in a predetermined location and he approached quickly.  After only a few minutes of small talk he said he’d like to suck my cock and fuck my ass and we left together.  We rode in his car back to his hotel.  During the ride, he rubbed my crotch.  Once in the room, he pulled me close and kissed me.

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? We kissed for a short while until he suggested we get naked and lay down.  We continued kissing and he stroked my cock while I stroked his.  He then said he wanted to taste me and gave me a fantastic blowjob.  Before I came, he said it was my turn to taste some cock.  I licked his shaft from the base to the tip before wrapping my lips around him.  I was incredibly turned on having a real cock in my mouth for the first time, but also felt somewhat detached from the experience, almost as though I were observing myself sucking his cock.  I tried deep throating him, but gagged.  After a while, he asked what I would like to do next, and I said I wanted him to fuck my ass.  He nodded and I jumped up to grab a condom and some lube.  I laid on my back and threw my legs up in the air.  He slid into me slowly and we kissed deeply as he did so.  Initially, I lost my erection, but as he began to pump into me more vigorously, I got as hard as I’ve ever been.  His cock simply felt right being inside me.  After a time he asked me to ride him and I obliged.  I continued to bounce on his crotch for several more minutes while he stroked my cock.  He asked me to cum on him and I masturbated furiously while continuing to ride his cock.  Before long, I shot one of the biggest loads I’ve ever produced onto his chest and chin.  He grinned and rolled me onto my back so he could masturbate and cum on me as well.  Afterward, we cleaned up quickly and agreed to get together again.

Did you have an orgasm? Did your partner(s)? We both came by masturbating on each other.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No precautions for the oral sex, but he did wear a condom during anal sex.

What were your REASONS for having this hookup? I’d been curious about sex with other men for more than a decade and had wanted to feel a real penis in my ass during this span.

Were alcohol or drugs involved? If so, how much? No drugs.  No alcohol.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? After the hook up I wandered around town for a while with a satisfied grin on my face.  I was happy with the experience and couldn’t wait to have sex with him or another man again.  Once I got home, I masturbated again and came on myself.

To whom did you talk about the hookup? How did they react? I’ve only chatted about the experience with others online.  Those I’ve told said they wished they had such a positive first same sex experience.

Was this a consensual and/or wanted experience for you? For your partner? It was consensual and wanted by us both.

Do you regret this hookup? If so, why? No regrets.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing was getting a longtime fantasy fulfilled in such a positive way.  Worst thing was that he couldn’t get hard to immediately fuck me again.  I don’t think this changed my way of thinking about casual sex.  I’ve always thought it could be a healthy outlet as long as one comes at it for the right reasons.  In this case, I wanted to try something I’d fantasized about and wasn’t expecting love or a relationship.  I also did not do this to make me feel better about me.  I simply wanted to explore something that had conceptually turned me on for a long time.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? We did get together one more time before he finished his consulting job.  Wish I had had a chance to explore more with him, but knew this was nothing long term before we hooked up the first time.

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