I'd been a very careful bisexual guy for my entire adult life, always using protection, making sure guys were clean, the works. And even then, I rarely actually got with guys. But over the last couple years, girls have been getting less and less attractive to me, and guys the opposite, until eventually I just started calling myself gay instead. And I'd been developing something of a cum fetish besides. After a lot of soul searching, I decided to try barebacking, but each time I tried to arrange something, I ended-up chickening out - until yesterday.
I recently had come out at work as gay at work after a brief fling with a gay coworker that didn't really go anywhere, and ever since I had, my supervisor had been...eyeing me. As a fairly well built black man a good head taller than me, he was totally my type, and there had been some rumors about him. Well, yesterday, he put to work with him on an assignment, just the two of us, in an area of our work without cameras. I didn't think anything about it at first, but as soon as we were alone, he locked the door to the area, turned around, and kissed me. I was pretty much instantly hard, though nervous as hell. After he broke the kiss, he told me he thought I was a 'fag' from the moment I was hired on, but wasn't sure. He told me if I was a good little fag for him, I'd get all the glowing reviews I'd want, just so long as I kept giving my me little white ass. He also said I didn't have to, and he wouldn't try to get me fired, but..well, he'd looked down at my pants and seen how fucking hard I was and was grinning.
Anyway, agreed, though my heart felt like it was about to pop out of my chest. He kissed me again, holding me by my neck, before lowering me down to my knees, and I got to work undoing his pants. His cock was rather nice, not the largest I'd ever had, but as it was between seven and eight inches, and pretty wide around, I'd say it ranks in the top three or four I've encountered.
After giving head for awhile, he told me to turn around and take off my pants. I told him I didn't have a condom on me, and he said he'd do it raw. I'd never been harder in my fucking life. I could feel my heartbeat in the veins in my neck and mouth as I managed to make myself agree before dropping my pants. I'd been gagging on his cock for awhile, so it was decently lubed, the best it could be with just spit and phlegm anyway.
He plowed my ass like a fucking freight train against the wall for around forty minutes total, with a break in the middle after his first load. Two big loads of my boss's cum in my ass had given me one of the best orgasms of my life. I spent the next six hours of work with his cum slowly leaking out of my hole, and he had me again after work. Of course I can't talk about it on the job, but he liked my ass enough to tell me he's happy to make this a long term thing. Apparently he has two other "boys" he fucks, though not at work, so I'm 'Boy Number Three', apparently, 'Boyfriend Number Three', if I'm lucky, I guess. On the other hand, 'Boy-slut Number Three' also works, especially considering that fucking cock of his.
Yeah, this has been kinda long winded and sounds more like a story written for the fiction section than real life, but I'm just naturally kinda verbose, and...well, it happened, and I don't think I'll want to use condoms anymore after this, with my boss or anyone else. I wouldn't quite call it a dream come true, as it's risky as shit regarding my job, but overall I'd say I'm waaaay happier now than I was a couple days ago, and certainly happier than when I spent most of my time trying to date girls.