Small town boy turned out by big city boss

[heyzeus]

Crystal and I didn't fit in in our hometown of 3400 in west texas. She was chubby and awkward and really into invader zim for some reason. I was gangly and nerdy and could not relate to my peers in the least.

 

It was less that we gravitated to one another than we were forced into a corner together. But we made the best of it lol. We commiserated and, even though we didn't really have much else in common, we were certainly horny enough to fuck each other and coupled up.

 

In the 11th grade, we made a pact that we'd move to houston as soon as we graduated. Both of us dutifully saved as much as we could from our minimum wage jobs.

 

We got out of there the day after graduation and got a crappy place near a bus line in the Montrose section. Our new landlord seemed charmed by use, and suitably impressed by how much we'd saved as high schoolers. Extracting much of that, we paid first and last and a deposit.

 

Whatever. We were thrilled to be here and hit the classifieds, Craigslist, etc. 

 

I wanted an office job and applied far and wide. I didn't get much of a response, 18 and having only fast food experience. But got a few interviews and as luck would have it, I found a position just a couple miles from our new place. I could bike there!

 

I was to be a secretary and assistant for this guy who was an independent investment advisor, Chuck --. He was middle aged and also from a small town. He said there was a good chance I wouldn't work out but was willing to take a chance. That plus $15/hr (!!) sounded good to me.

 

The gig seemed pretty great. I say in the small reception of the office, answered phones and ran small errands (in the boss's bwm!). Overall he didn't seem too busy, and I was often left to kill time (at $15/hr!!).

 

One day it was past noon and he wasn't in yet. I was bored and went into his office. I told myself I would straighten up but really I wanted to snoop.

 

Everything was very orderly. I snuck a look into his desk drawers but only saw the expected office supplies. 

 

I walked over to his TV stand and popped open the doors. I pulled out a drawer and whoah! It was full of gay vhs movies. 

 

My cock got immediately hard. Was I gay? I pulled out a tape--the bigger the better?--and put it in the player.

 

I couldn't believe what I saw. I pulled out my dick and jerked a huge load onto my hand and the floor, but I kept watching, rapt.

 

This was so much hotter than anything I'd done with crystal. I got hard again and was close to coming when the office door opened.

 

Fuck! Chuck walked in, took a deep breath, laughed and said, I thought you were a fag too. 

 

I couldn't process what was happening. He strode over and pushed me against his desk. Then he pulled down my pants and underwear and flipped me over so I was grabbing his desk.

 

He pulled lube from a drawer I didn't check and squirted some in my butt. He slid in me quickly. It was amazing and painful and confusing.

 

"Fuck you're tight. Are you a virgin?"

 

"No!" I said, like a lunatic, misunderstanding the question. "I've been having sex for 2 years."

 

He thrust in me deep calling me a slut as he came. He stayed in deep while the rest of his cum dribbled into my hole. He squeezed his softening cock up from the base and withdrew from my now sore hole.

 

He gave me a kind of pep talk, saying that the sex was amazing and that I should come to terms with my sexuality sooner rather than later. 

 

I burst into tears lol. He helped me calm down and then took me upstairs where there was an apartment with a shower and I got cleaned up, using finger to pull as much cum as I could from my asshole. I dressed in my work outfit of dockers and an old navy button down. 

 

I came out to find Chuck and 2 other guys naked and watching porn. The others were mid 40s like Chuck but rougher looking, kinda like bikers. Chuck looked at his watch and said "2:30? Not quitting time yet. Come here."

 

I protested but weakly. Soon I was naked with a finger in my cummy asshole. 

 

Chuck held a bottle of what I later learned were poppers in front of my nose and told me to inhale. As I did I was penetrated by one of the strangers. What the fuck was I doing?

 

In the half hour that followed I had anal sex with all three men and each of them ejaculated in me. 

 

****

 

I headed home and took the longest shower of my life. Crystal and I had a terrible conversation and I guess she'd internalized more homophobia then I realized. 

 

Everything I told her was on Facebook by morning. 

 

Before long, i was trading Chuck sex for a place to stay...

 

[negchaserlooking]

hehehehehe Think Chuck and his mates have found themselves a new toy

[Mvillebottom]

Nice start looking forward to reading more

[bottombehr]

Nice start. More please!

[austin_submale]

Nice start!  Hope to read more!

 

[pozpopperpig]

Great start!