by Darko_D

Gender: Male
Age: 26
Race/ethnicity: White
Current location: Alaska
Highest education received: College degree (eg., BA, BS)
Occupation: Military
Relationship status: Single
Religious affiliation: Christian
How religious are you? Somewhat
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Heteroflexible?
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 0

Failed First Attempt

How long ago did this hookup happen? 5 years

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…)? One Night Stand

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 older than I was, I think he was about thirty. He was fresh out of the military and working for a law firm in my town. We met online because I was feeling very bi-curious. He was a gay male, and there was something about the way he spoke to me that made the fantasies I had been having seem less threatening. He was about six feet tall, black hair and green eyes. He had a strong body and was fit without being obnoxious about it. He had an easy personality and a lovely, disarming smile. I felt very comfortable with him and turned on by his masculinity.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had met once before at a pub for a “get to know you” drink and felt comfortable about meeting again for sex. We were both very open about that. I wanted to be fucked and he was interested in fucking me. We agreed to meet at his house after work on a Friday afternoon in July.

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? It was summer in the South, and I was working construction for the summer, so when I got to his house, he asked if I wanted to shower. I did, and he gave me a nice robe for after. When I had finished showering, I put on the robe and went downstairs. I found him in a similar robe, and saw he had also showered in his own bathroom. We had a glass of wine and made small talk for a while before he asked if I wanted to go upstairs and watch a movie. We went into his room and he put on a dvd, and I was laying on my stomach on his bed. After ten minutes or so he began to stroke my leg and asked if he could kiss me. This made me tremble and I said he could. I rolled over onto my back, the way my female partners did for me and he moved on top of me and kissed me. It was my first time kissing a man, and I was unprepared for the difference from kissing a woman. He was more aggressive than I was used to, and used a little too much tongue for my taste. I admit, though, that having him over me and feeling our legs against one another was sexy. As we kissed, I stroked his back and ass under his robe and hooked my legs over his, pulling him into me.
He asked me if I wanted to suck his cock and I said yes, so he took a kneeling position on the bed and removed his robe. His body was very nice, and his cock was bigger than mine, though not freakishly large. He pulled my robe off of me and I began to suck his cock. I immediately knew that I liked it! He stroked my shoulders and neck as I sucked him and told me little things to do to make it better for him. After a few minutes he lay back and I resumed sucking his cock and licking his balls. He produced a lot of precum and I was very excited by the taste of it, and the smell of his body. I swiped my tongue across his ass once or twice and I knew he liked it, but I felt kind of uncomfortable doing it, even though I love rimming women.
Eventually he put me on my hands and knees and began to use his tongue on my ass. I’d never had a rimjob before and as he did it he slowly stroked my cock. He took his time and opened my ass with his tongue and fingers, using just enough lube that it was not just comfortable, but extremely pleasurable. When he determined I was ready, he got up behind me and put a condom on. He pressed the tip of his cock against my ass and the head slid in without pain or even discomfort. It was one of the best feelings I’ve had sexually.
I completely lost my nerve at this point and jumped up off of the bed. I apologized profusely and dressed as quickly as I could and basically ran out of the house and into my car.

Did you have an orgasm? Did your partner(s)? Neither of us did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed it in detail, and he used a condom.

What were your REASONS for having this hookup? I wanted to have sex with a man. It was something I had been fantasizing about for years.

Were alcohol or drugs involved? If so, how much? We each had a glass of wine.

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? I never saw him again and changed my phone number. I felt both profound guilt about what I had done and how much I enjoyed it–because I really enjoyed it a lot. I also felt extremely guilty for not going through with it and how he probably felt afterward. Now I regret not letting him fuck me, because he’s a great guy and would have been perfect for my first time.

To whom did you talk about the hookup? How did they react? No one, ever. This is the first time I have written or spoken of it.

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

Do you regret this hookup? If so, why? I regret the way it happened and letting myself chicken out and not have the experience.

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? The best thing was how gentle he was and how much I enjoyed all of it.
The worst was that I didn’t finish it and left us both unsatisfied out of, I suppose, fear.

It definitely opened my mind to future experiences with men and taught me how to make my partners enjoy anal sex by taking the same care he did with me.

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup or anything else? If you’re reading this, and you know who you are, I’m sorry.

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