I met Chris and liked him immediately. I had no idea about his secret or how it woud affect us.
I was working at a call center doing customer service for a power company. The pay wasn't great but being that I was fluent in Spanish, I was paid an extra $1.50 an hour for it. We also worked 10 hours of overtime a week so it added up. I rode a crotch rocket motorcycle, a Yamaha R6, to work everyday. Several other guys rode motorcycles to work but they were Harleys. Crotch rocket pilots and Harley riders don't ride together. There were two designated parking areas for motorcycles. All the Harleys and cruisers parked in one, my single, ostracized R6 was parked alone in the other one.
One morning, I parked and as I removed my helmet, I heard the four cylinder growl of a crotch rocket pulling into the parking lot. The rider parked his Suzuki 600 sportbike right next mine. I waited for him to remove his helmet so I could greet him. He was my height, 5' 10”. Chubby but in a burly sort of way. He took his helmet off and I was struck by how handsome he was. I am not into guys and never even acknowledge how a guy looks but he bordered on beautiful. It surprised me that I saw him like that.
It was still early. We exchanged names, his was Chris. He took off his armored jacket and I noticed he was wearing a black polo and khakis. There was a gun on his hip. Turned out he worked for the security company contracted to our building. He had been transferred from another site due to a female guard having a baby and going on maternity leave.
We hit it off. We rode together on weekends. Had beers after work. Hung out at each other's place. I really liked the guy.
We had a long weekend come up due to a holiday and planned a road trip. Go out on the road for a couple of days, see a few sights, eat different stuff, maybe get laid. I had noticed that he wasn't really into women. He rarely looked at them. I didn't get a gay vibe from him, though. I assumed he maybe was a prude or not that interested in sex. Me, I was a dedicated horn dog. If it turned out he was gay, it wouldn't matter to me. Not what I was into. Not anymore, anyway. I had a week long fling with a gay dude in college. It was fun, I enjoyed it. Didn't regret it but never really wanted to do it again. Though I really didn't know what I would do if the opportunity presented itself with Chris. I really liked him as a friend, but I found him very attractive.
After riding for most of the day we pulled into a hotel. I showered first. I came out, toweling off, not covering up. I played football in high school and college. I also did 6 years in the Army. Being nude around other men was nothing to me. I laid on one of the beds naked. Chris went to shower.
When he came out he had a towel wrapped around his waist. He had a deep, muscular hairy chest. He also had a bit of a gut but it made him sexier somehow. He had like a powerlifter physique. I felt a bit of desire for him. He was just so damned hot!
“There's something I want you to know. No one knows this. Just close family. I really don't want anyone else to know this. Not right now.”
“You can tell me anything Chris.”
He opened his towel. He had the puffiest, hairiest pussy I had ever seen in my life. I was shocked. I had no idea what to say.
“I've been transitioning for a while.”
“I can see that.”
“What do you think?”
“Chris, that's been there since we met. Why should it make a difference?”
“I'm so glad you feel that way. I'm sure you have questions.”
“Well, duh! How is sex for a guy with a pussy?”
“I don't know. The last time I had sex, I was still a girl girl.”
“Damn!”
“I still get off by masturbating.”
I found that intriguing. “I would like to see that.”
“I don't know. Seems kind of weird. You sure you want to watch?”
“Yes.”
He laid back and started to rub his clit. He seemed a bit nervous and it took him a while to get into it. He didn't notice I had a raging hard on. He closed his eyes and tilted his head back. I made my move. I slid off my bed and got between his legs. “Getting a closer look?” He asked, smiling.
I didn't answer. I just clamped my mouth on his pussy. HIS pussy, seems weird writing it even now. I chowed down on his cunt like I was starving to death. It didn't take him long to cum. He didn't squirt but he got extremely wet, his juices were all over my face. I slid up his body and slid my cock into his pussy. There it is again, HIS pussy. The sensations and thoughts were all over the place. This was Chris. My best friend. For all intents and purposes A GUY! But here I was, balls deep in his pussy and absolutely loving every second of it. I came. The most intense orgasm I ever had in my life. I didn't want it to end. I kept going. Chris came, his already tight pussy squeezing my cock. I came a second time. I didn't want to stop. I kept fucking Chris until I went completely soft then rolled off of him.
I looked at Chris. “What the fuck was that?”
“What do you mean?”
“Was that gay?”
“I have no fucking idea. But I loved it!”
“What now, Chris?”
“I don't know. This just a one time thing? “
“I hope not.”
With that I crawled between Chris' legs and started eating his pussy again.
It's been a month since this happened. We have been fucking like rabbits since. He takes it up the ass sometimes, gives me great cum swallowing blowjobs. Fucking him in the ass is fun and all as are his blowjobs. But it is like fucking that guy in college. When I am pounding away at that pussy though, that is special.