Crossing Over, My First Time

In my late thirties I attend a convention in Dallas and stay at a large hotel. I get this idea of putting a note inside a stall in the men's room near the convention center with an honest request. "Straight man wants to experience gay sex" My room number and a request for the person answering to leave a note at the front desk for my mail box. Fifteen minutes later I get cold feet, go into the restroom and the note is gone.

I check the front desk around eleven before heading up and there is a note, text ### x. Back in my room I sit with the note in my hand and decide to ignore it. But the curiosity gets to me and around midnight I send a text. "Hey, it's John". I get a text back, "Hey John, you serious?". I text back "I think I am". A knock on the door and there is a man in his forties, stocky, beard, and he says 'hey John, I'm here to be of service".

He walks me through what to expect, he makes sure I'm totally sure about it, makes sure I've never done anything like this before, wants to know if I want the full experience or I'm just interested in touching cock and maybe sucking cock? I tell him I want the full experience, I've always wanted it but never had the nerve to act on it. He tells me that to start we should take our clothes off and standing naked he gets close and uses his cock to touch mine, then takes my cock in his hand and tells me to take his cock in mine. His hand on my cock is what I am focused on, it feels so good and it's so bad at the same time. I hold his dock but not like he is holding mine. He sits on the bed and puts my cock in his mouth and sucks, I mean sucks using his tongue to work around my glans.

"Now it's your turn", remember to keep your teeth out of the way. Just suck and enjoy it, guaranteed you are going to like it. His cock is big, he is half hard and I put his cock in my mouth and try to suck on it, he holds my head and tells me to take easy, make love to his cock or he won't cum. His cock is big enough that I hold it with my fist and suck on it, the more I suck the more I like it. I notice that my cock is limp and he is hard. After a while he pushes me backwards, shoving me from the forehead, he gets down and sucks me again, this time shoving his finger in my asshole, he finds my prostate and makes me cum. "Good boy, like that?"

We lay side by side, he has me hold his cock in my hand, he rubs me down, pays attention to my butt cheeks and my chest, pinching my nipples and asks me if I want to kiss. He warns, once we kiss I will never be able to claim I'm not gay. We kiss, he's on top of me, I have his hard cock in my hand. He asks me if I want it like a woman or a man. I have to ask him what he means and he says, men take it in the ass, women want it face to face. I ask him what he thinks and he says let's fuck you in the ass.

I get on my hands and knees, he fingers me again, for a while and he rubs the head of his cock against my ass, he tells me to bend my head down and to bite my lip if it hurts, he's going in dry. It hurts, it feels like he is tearing into me, it stings, and he shoves putting his body weight behind it. After a while I feel like I have a baseball bat in my ass, he's shoving in a rhythm, big shove in, little pull out, big shove in, little bit out, he shoves hard and he let's out a moan, "nice tight ass".

It's over. All of a sudden I just want him to leave. I don't know what to do. He lays on his back, his cock like some huge worm, his big harry belly and chest, his thick harry thighs. He tells me a man's go to do what a man's got to do. He tells me there is one more thing for me to be part of the club. We take a shower and go back to the room, he gets on his hands and knees and bends down and tells me to lick his ass, make love to his ass with my tongue, to take his cock in my hand and jerk him off while I lick his ass, not to stop till I make him cum.

I don't want to but I do, holding his hard cock in my hand, I'm licking his ass, sucking on his ass, kissing his ass, I like it in a very sick sort of way, I jerk on his cock, he makes noises and tells me to keep it up, show him I'm his bitch, jerk him off and after a while he starts to cum, his cock jerking in my hand. I stop, he turns on his back and tells me to suck his cock. I do. He tells me he is spending the night and get close to him and he puts his arms around me and spoons me, his cock against my ass.

I got to the convention the next day, he is there, he man's the booth of a competitor. He tells me If I'm up to it he could do it again that night, this time he's bringing lube, won't hurt, just enjoy it. We have dinner, we go to the room, we get naked, I suck his cock for a long time, he jerks on my cock, he lubes me up and fingers me with his finger, massaging my prostate and making me cum again, he climbs on my back and his cock slips in, still big and hard but it feels good. We lay afterwards, kissing and holding cocks in our hands. We shower in the morning, I rim his ass in the shower, this time I'm into it and we go to the bed where I jerk him off again, but this time I don't want to stop. The second night and morning I had experience. And we kissed. Long kisses, his beard against my face, I'm gay I said to myself. I'm gay. I kiss.