Well, I Took The Plunge...

[CreamMe]

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.

[KindaBasic]

Pussy was nice, but damned if dick isn't best.

[CreamMe]

Update! I've taken loads from my boss every single day since I made my first post, and it has been amazing.

 

The two days after that post, I worked, and while my boss didn't drop any more loads in my ass on I was on the job, but he did insist I frequently suck his cock.  He had me working on my skills at deep throating, an activity I had tried before.  Generally I can keep myself from gagging, but I can't quite manage to get it down my throat, so he's been face fucking me, blowing loads right down my throat or on my face.  He insisted I go down on him twice the first day and three times the second day, if one counts the head I gave him in his car after work.

 

The real fun were my three days off though.  He had me come over to his house, and gave my a dog collar to wear, and told me I had to keep it on in his home if I wanted to be fucked.  And boy howdy, he fucked the ever living shit out of me.  He seemed like a fucking animal.  Oh, and for the first time ever I experienced a no-hands orgasm.  It was both the roughest and best sex I had ever had.

 

The second day was more of the same, with lots of practice in deep throating.  In the evening he had a couple friends over.  The guys were not really my type, but all of them had good-sized cocks, and well, my boss ordered me to service them, so by the time I went to bed that night, my stomach was half full of cum. I had have never done as much before, but I felt amazingly liberated.

 

The third day was a lot more laid back.  I think he needed a rest.  So after waking-up he dumped a load into me, and then called his friends to use both my holes, not merely my mouth.  I know I should be terrified of what I'm doing, and I suppose this all sounds so messed up, but honestly, it just makes me hard remembering it.

 

The rest of the work days were most face fucking and one quickie.  Amazing sex, but not as mindblowing as when I stayed at my boss's house.  I just don't have the words to do justice to that experience.

[crazyascanbe]

as long as you're happy have fun!

[btmforhungtops]

You lucky b'stard! Lol

[Guest yelrom]

you lucky so and so

[chubbybear]

" . . . Two big loads of my boss's cum in my ass had given me one of the best orgasms of my life . . ."

 

Hot story of your first BB encounter. I think your experience is pretty common with guys (especially bottoms) entering the realm of BB sex for the first time. I was careful for years but always wanted to give in to my secret BB desires. I too had a few aborted attempts but when when it finally happened my dick was harder than it had ever been once he slid his raw cock inside me. But, as much as I was enjoying it that little voice in my head kept saying "you shouldn't be doing this" and I was considering making him pull out before he came. Then without warning it was too late -- he started cumming and was pumping his load deep in my ass. That was all it took for me to shoot the biggest load of my life handsfree. It felt amazing and I knew instantly that I had just discovered my favorite way to cum -- with a hot load being deposited in my ass. I haven't had sex with a condom since that experience. 

[tradiemason]

Lucky boy ! I luv bein passed around to service me tops friends

[CreamMe]

Long time, no post.  The past two months have been wild.  I can now deep throat my Boss!    And he has been making frequent use of my new skill.  I also got to play along side some of his other boys, in addition to having had a couple great group nights with the Boss's friends.  Oh, and he officially declared me his favorite boy.  The other two were soooo jealous.

 

We're still on the down low at work, but due to some, shall we say, timing mishaps, I ended up having to introduce him to my family, which didn't know I was gay.  It was initially awkward but after a while were accepting, even if he openly controls me, as he often does.  For instance, he insists I wear a collar all the time outside of work.  Oh, and speaking of work, when I said  now. And at work, well, when I said we were on the down low, I wasn't entirely accurate.  My boss' immediate supervisor also knows, because my boss has shared me with him.  It came to a head when my boss and I were both called into the supervisor's office, and no sooner had the door closed when the supervisor announced "I know what was going on between the two of you."

 

I thought I was fucked, and apparently the look that crossed my face was emphatic, because they both cracked-up upon seeing my expression.  It turned-out the supervisor had known the whole time, and had even shared one of Boss's other boys some time earlier.  After that, well, I can't say I ever expected to be spit-roasted at work by two black guys when I took the job, and I especially wouldn't have expected to be deep throating one of them.

 

Oh, I should add, my Boss read my post on here, and approved it.  He has encouraged me to write some actual fiction.  Considering the responses I've received, I imagine I will try my hand at it soon enough.

[justsexnowatl]

fucking hot post and updates - you're right, it sounds like fiction, but I believe you 100% - lots of times real life is better than fiction!!  Hot as fuck that the boss' boss is in on it too.  Wish I worked where you do - would make the workday go a lot faster!! Also was wondering about the other 2 boys as I read the whole post - glad you guys all got to share