Another Day, Another Dollar

This last summer, I had just completed my third year of college and rather than going home, I kept my apartment and ran an add in the local town paper looking for work as an interior painter. Having worked for my uncle every summer since high school, I knew I could do the work and make good money. The catch was landing some business. Uncle Sam, yeah that’s his name, was disappointed that I wasn’t going to be working for him, but gave me a great referral. A friend of his had a brother in the town where I was, who had just purchased an older Victorian. The house had six bedrooms, as well as all the other rooms that come along with a home like this, and they all needed serious painting.

My name’s John. As I said, I’m going to college trying to figure out my major. I’m 21 years old, a little over six foot, have bleached blonde hair that I wear somewhat long, weigh about 160 and pretty much look like a surfer dude. I’m not bragging, but most girls, and I have to say guys also think I’m cute. I’m too skinny to be a hunk, but I get hit on pretty often, again by both girls and guys. I’ve always been straight. I mean I’ve never even thought about doing anything with a guy. On the over hand, I’ve never really been repulsed or turned off by the idea. I’ve just never thought about it. I know I’m not gay though. It’s a pretty good indicator that just the thought of a nice set of tits gives me an immediate hard on while I’ve never gotten one thinking about, or looking at a guys ass.

Well, to skip ahead, I called Milo, the brother of Uncle Sam’s friend, quoted him on the business, and got the job. Milo was a nice guy, in his early 40's. He’d spent a number of years as a software developer in California. While as he put it, he wasn’t that good at software, he was good at picking up stock in a number of tech firms, before they made it. He was also astute enough to have gotten out of the market while they were at top dollar.

Milo was probably as well off as anyone I’d ever met, and he was also, and while I know this isn’t a the correct way to put it, about as queer as anyone I’d ever met. He was blatantly gay and didn’t care. I knew better than to think I got the job based totally on my resume, after all, I didn’t have one. But, I thought at the time, based on what he was paying me, he could stare at my ass all day long! What I didn’t know was how much I’d get into having him stare at it. Well I guess it kind of proved the old play with fire bit, but I’m getting ahead of myself.

All my stuff was in the dinning room, paint, drop clothes, ladders, and I was set to start on the living room. Knowing why my bread was being buttered, I chose to wear a new pair of bibbed painters overalls with nothing on underneath. No shirt. No shorts. No socks. Just overalls and shoes. I was a gay guys wet dream, or at least I thought I was. Milo was in love. He made me lunch, brought me drinks, and spent as much time as he could sitting in the kitchen where he had a clear view of me at work. What I hadn’t realized beforehand was that all the sexual tension I was creating was having it’s own effect on me. Most of the time he was watching, I was sporting a hard on that was difficult to conceal, especially in baggy overalls.

This soft-core play acting went on for 2 days. If I needed to open a can of paint, I always made sure my ass was pointing in Milo’s direction as I bent over. At about nine am on the third day, Milo came over to where I was working. “You know,” he said, “for a guy who’s supposedly straight, you’re the biggest cock-tease I’ve ever met.”

“Uh, sorry,” I responded not knowing what to say. I knew I was bright red. It was obvious what I’d been doing, but I didn’t expect to have to own up to it. I even thought that he may figure it was unintentional . . . yeah right.

“Well,” Milo went on, “since you know what you’ve been doing, not that I’m not enjoying it, I’d like to make you an offer. I’ll give you an extra $2000 if you finish the job baby assed naked.” That’s just how he put it, “baby assed naked.”

“What do you mean,” I intelligently responded.

“What I mean,” Milo replied, “is that you finish the job wearing only your shoes. If your going to parade around here half naked, you might as well parade around completely naked.”

Two grand. Man that was a lot of money. Without even thinking I blurted out, “sure.” I stood there staring at him, red faced, not believing what I had just agreed to, but 2 grand . . . Jeez.

Milo walked over to the living room windows and lowered the blinds.

The immediacy of the situation struck me. “Now” I questioned? Reality was sinking in. Answering my own question I softly said, “I guess so.” I sat down on the floor and took off my the old skater tennies that I used for my painting shoes. Standing up, I looked at Milo and asked, “can I wait just a little while?” The problem was that I had a raging hard on.

Milo looked down and smiled. “Don’t be embarrassed. You’ll be giving me my monies worth.”

Unclipping my bibs, I let them fall down, only to have them get hung up on my hard cock.

“All the way John,” Milo responded with a laugh. When I just stood still, he reached over and pulled my overalls, freeing them from hard cock, letting them fall down around my ankles. My dick sprang free, pressing against his wrist. Milo slowly pulled his hand away, curling his fingers and gently tracing the underside of my hard penis. My knees nearly buckled and Milo quickly grabbed my arms steadying me. Sensing little resistance on my part, he reached down and gently stroked me. I started to protest, but instead let out a soft groan as the sensations took over. I was so hard I thought I’d break. Milo guided me to an over stuffed chair covered in a drop cloth, and maneuvered me down into it. My legs were spread and my cock stood hard and erect. He knelt in front of me. I’d never had a blow job before and I nearly blew my load as his lips approached my dick.

I felt the hot warmth of his mouth envelope my cock head. He cupped my balls as he sucked me. He did me with the intensity of someone who not only knows what they’re doing but also loves it. When he scraped his tongue along the bottom of my cock head I couldn’t hold back. I tried to pull his head from my cock, but he grasped my ass in both his hands and held me tight. Milo knew I was on the brink and sucked me as if he were trying to suck the cum out by force alone. I exploded shooting jet after jet of hot cum deep in his mouth. Milo held my ass tight, his fingers spreading my cheeks and pressing against my virgin asshole. My head was pressed against the seat back, my hips thrust in the air.

I felt as if I was pumping myself inside out. Milo eased up, rolling my dick head between his cum coated lips. With one last body shaking shudder, I collapsed down into the chair. I couldn’t move. Milo slid his mouth from my dick, sending another tremor through me. I felt numb, and in a state of shock. Less than 5 minutes ago I had been painting his living room, wiggling my ass, being a real cocktease. There was no way, at that moment, I could have imagined that 5 minutes later I’d be prone in this chair, completely naked, my cock sticking up, hard as a rock, slick with my own cum and Milo’s saliva, having just had the most intense sexual experience of my life . . . with a man.

As my mind attempted to sort out this rather sudden change in my life, Milo stood up and moved to the side of the chair. Bending over, he took my right nipple in his well lubricated mouth and flicked his tongue across it. Once again my body shuddered. Milo smiled and planted a cum sloppy kiss on my forehead.

“Don’t worry,” he said, “it’s just sex.”

“Uh yeah,” I replied. “Uh, thanks,” I said, not knowing what else to say.

“Well, you’re welcome,” Milo answered, looking me in the eyes and smiling. “Anytime.”

Milo walked towards the kitchen. The bulge in his jeans was obvious. I lay naked and prone in his over stuffed chair, on top of my own drop cloth. I heard the water run and Milo came back carrying a warm wash cloth and a towel. My cock had just started to droop as he started to gently wash me off. The warmth and soft abrasion felt so good. God, I was getting hard again. Milo changed his motions to a gentle up and down, pumping my cock with the wash cloth in his hand.

Continuing his jacking of my dick, he bent over and started to suck on my nipple. Stopping for a moment, he turned to me and said, “When I said anytime, I had no idea.”

I was already lost in the sensations and merely moaned my reply.