by jym the bear

Gender: Male
Age: 53
Race/ethnicity: European-American
Current location: Richmond, VA
Highest education received: College degree (eg., BA, BS)
Occupation: supervisor
Relationship status: married
Religious affiliation: Southern Baptist
How religious are you? Somewhat
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Gay dominant Heterosexual.
How many sexual partners have you had in your life (including oral sex)? 13
How many hookup stories have you here posted before? 1

Walk Right In

How long ago did this hookup happen? 3 days 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…)? 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? I did not know this partner at all.  I had “smiled” at him on a gay dating site. He saw that I was online and not having any luck picking someone up at the local cruising site, and sent me a wink. He was very nice and not at all aggressive like so many men online. I got a very positive feeling about him especially since we are both bottoms and he offered to top for me so I could finally experience my first anal sex. He was a large, bear of a man, with a beautiful large belly, and other large sized attributes.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The hookup began online with a chat, and was completely unplanned. I had spent the day cruising different “hot spots” trying to get laid.  My wife was out of town for an extended period, and I knew this was going to be my best chance to finally achieve my dream of having full-on, homosexual, anal sex. He instigated the hookup and gently encouraged me to come over.

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? After only a few minutes of chat, I decided I needed to just go and meet this man and finally have anal sex. He seemed nice and the idea of the random meetup has always intoxicated me. He originally wanted me to just walk right into his house, climb into bed, and anally fuck him. I told him I might not be able to perform that right away, but would try. I got in the car, removed all clothing, and drove to his home.  When I arrived, I got out, still naked, and walked right into his home, up the stairs and into his bedroom. He was laying on his back completely naked, with a slight hard on and I immediately began to suck his dick. The thrill was intense. He became unbelievably hard and asked if I really wanted him to fuck me. I said yes, and he positioned himself to oblige me as I lay on my back with my feet in the air. He gently entered me and then began to pick up speed. I liked It so much I told him to pound me harder and he did. When I said harder, he asked if I was sure. He was so gentle, yet so rough, I felt completely safe in his hands. At that moment, with this large, beautiful man, sliding his large dick inside me, I realized that I felt no shame, or guilt. Instead I felt a sense of such pure happiness that I realized this was who I really am. I am a gay, bottom, man with occasional heterosexual twinges. I watched him as he neared orgasm, and had the biggest smile as he grunted, shuddered, and came inside me. I could feel his dick spasm, and I cannot describe the level of joy that moment brought me. It was a sexual, spiritual, emotional, whirl of satisfaction and peace.  Afterwards he lay down next to me and I spent the next half hour giving him a massage/back rub, and running my hands all over his deliciously massive body. We talked about how I felt, how he felt, how amazing it felt to have a man inside us, and other small talk. I didn’t want to leave, and he wasn’t pushing me out! I felt so perfectly alive and happy, but I knew it was time for me to go. I thanked him for his gentleness, and his generosity, gathered my things and-still naked-walked out to my car and left.

Did you have an orgasm? Did your partner(s)? I did not have an orgasm, he did. Funny thing is, I didn’t need one!  The sex itself was enough of a feeling for me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We talked about our sexual status and “cleanliness” before I arrived.  I was confident in his answers, and I assured him of my own status with reports of my exam, though I really had no actual proof handy.

What were your REASONS for having this hookup? When I was in 8th grade, I had a sleepover experience with my best friend. He reached into my pajama pants and stroked me to orgasm. I returned the favor, then later we ground against each other with clothes on. I spent the next 38 years thinking about it from time to time, and pushing the feelings it brought up ever deeper into the back of my mind.  About 8 years ago I gave up and sought out several hookups for oral sex, with the intent of eventually having anal sex. Though my sexual appetite was a major reason to pursue this action, it was the underlying quest to answer the question from 8th grade…am I gay.

Were alcohol or drugs involved? If so, how much? Totally sober!!

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 hookup I could not stop smiling. I felt such euphoria and happiness, that I wanted to tell someone about it…of course that is not possible. I have thought about it so many times this week, and even reached out to him about a return visit. We may meet again for another round and I am going to try and be top for him. I owe him that. I would never have considered being with this man before this experience. I would have told you he was too fat. Now I have a new and better perspective on looks and sex. His size and his sexuality are one and quite potent, who knew? I want to be with him again, this time for a whole night and other activities.

To whom did you talk about the hookup? How did they react? I cannot talk to anyone about this. I think that is why the fact that he lay there talking to me as I rubbed on him is so valuable to me.

Was this a consensual and/or wanted experience for you? For your partner? Consensual all around.

Do you regret this hookup? If so, why? No!  It is the only hookup I have had that I do not regret in some way. It has freed me internally, at least, and allowed me to consider myself more honestly.

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 about this hookup is that it changed my entire view of myself and my sexuality, indeed my sexual identity itself.  I no longer consider myself a heterosexual man who experienced homosexuality and liked it. I now see myself as a homosexual man who enjoys heterosexual sex mainly for the joy of pleasuring the woman, not for my own pleasure. Although most would call that bisexuality, I would not, though I use the term to avoid arguments. My deepest remaining desire is to someday be able to tell my family and friends who I really am, and how I really feel.

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? On a basic sex level, I would encourage all people to let go of the stigma against anal sex and allow themselves the pleasure. On a sexuality level, I would encourage all those who can to be the person they can be and be happy.
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