Ex convict earns his Harley

The whole neighborhood was buzzing. It seems old Mizz Julie's wayward grandson, Cole, was getting out of prison. Even worse? He was coming to live with Mizz Julie. Can you imagine?

Apparently, the neighbors couldn't. Why one would think Armageddon was howling at our doorstep.

His arrest and incarceration happened before I moved in. I'd heard a bit of gossip. Didn't seem like a huge deal to me. He'd stolen a car at seventeen and went for a joyride. Unfortunately, it was a very expensive car and he managed to roll it. The owner wanted blood. Stupid youth prank, that he'd paid dearly for. There had been a rash of adolescent car theft. They decided to make an example of Cole.

Ten years.

I mean, come on. The sentence seemed overly harsh to me. Especially, the whole no possibility of parole. For a car theft?

It's not like he murdered someone.

So, when elderly Mizz Julie came to my door asking for a favor, I was happy to help out. Mizz Julie hadn't driven in years. I often drove her to the grocery store or to various appointments. I'm just that kind of neighbor. Hopefully, I'll bank some Karma and some day when I'm old, someone will help me out.

So, here I was driving her to the men's penitentiary a couple hours away. To pick up her wayward grandson. Wondering why his parents weren't doing it. Wondering why Mizz Julie was the only one who was stepping up to the plate for him.

Luckily, once we'd arrived, it didn't take long for her grandson to come through the gates.

Woof!

I don't know what Cole had looked like as a seventeen year old, but the twenty seven year old version was all man. Tall, blonde, long lean muscles. A tantalizing patch of blonde hair spilled from the throat of his shirt. He had a striking face. Not classically handsome, a more raw boned, sharp edged face.

Julie insisted on climbing into the back seat, so Cole could sit in front. More room for his legs. I kind of wished he'd sat in back. I was incredibly aware of the hardbodied stud just separated from me by the console.

Mizz Julie started chattering away. Like she was nervous and trying to fill a void. Cole responded with one word answers. Other than greeting and thanking me for the pick up, he didn't say much at all to me. Which was fine. I didn't really know what to say to a man who'd been locked away for ten years. The trip back seemed to take forever, the tension was that high.

I dropped them off at Mizz Julie's and relieved the trip was over, went about my business.

The next morning was Sunday and my first glimpse out the front window, nearly had me choking on my coffee.

There was Cole in nothing but a pair of tiny shorts, athletic shoes and white socks, stretching on Mizz Julie's front lawn. He was practically doing splits. Which revealed the cloth of a jock at his crotch. Those shorts must have been left over from when Cole was a teenager. They were obviously about two sizes too small.

Not that I was going to complain about the scarcity of cloth.

He'd found a patch of sun to stretch in. One that illuminated quite a bit of golden hair on his body. He was pale. Well, I suppose he would be. I'm sure he didn't get to sun at he much in prison. An errant thought had me hoping the man had on sun screen.

Then he turned around and bent over, revealing a high round butt. Those little shorts rode up his crack, perfectly separating each cheek. And my coffee almost came out of my nose as I gasped.

I felt perverted, standing there watching his body move through his stretching routine. My dick liked to have poked through my sweats

One evening I was surprised to find Cole knocking on my door. I invited him in and we sat awkwardly facing each other on the couch. I could tell he was ill at ease, and I didn't know him enough to put him at ease.

After a couple of long silences, Cole finally blurted out the reason for his visit. He needed to get his driver's license, but Mizz Julie didn't have a car anymore, and could I take him to take the test and could he use my truck?

I said yes, Hell, I felt like the guy deserved some breaks. Letting him use my truck for his test seemed a good thing to do.

I was actually pleasantly surprised when he passed the test the first time. Would have thought he'd be rusty. Turns out he'd spent most of his time at a Correctional Farm, and had driven most of the farm vehicles. He opened up to me a bit more and I found out getting a job was like finding hen's teeth.

That's when he broached the subject of modeling for me. Mizz Julie had filled him in on my art studio. She'd also let drop that I often paid people to sit for me. He said he really needed some cash.

I gave him a long look. Asked him if he knew I was gay. He turned a little red, but answered yes, the whole neighborhood knew it. Then I asked if he knew the nature of my artwork? He got a little redder but gave an affirmative nod. Made me wonder just how much little old Mizz Julie knew.

So, I told him my usual prices for modeling. Fifty for partial clothes. One hundred for basic nude. One fifty for erotic nudes,as in hard ons , butt hole exposure, sexual positions. Two hundred for modeling with another model in erotic positions.

His eyebrows launched near his hairline at the last. Guess Mizz Julie didn't know everything.

He said he would be willing to do either of the first two. He said he didn't feel like sitting for the hard core erotic poses. I agreed and asked if he minded sitting right away. He agreed.

After a moment I asked him to go home and put on his running shorts and his jock. He looked startled and I laughed. I pointed to myself. "Gay man.". I pointed to the window. " I won't lie. You've made my morning more than once, doing your stretching routine on your front lawn. ". Cole turned red as a beet.

But. He went and got those shorts. We did the session out by my pool.

He turned out to be a good model. Able to sit still and hold position for long periods. I got one great drawing done of him in his too small shorts.

Me? Not only did I get a great drawing, but got to stare at every inch of his body , not covered by tiny shorts, to my heart's content.

I told him in conversation that the Art Academy was always looking for models. Especially, if he was willing to sit nude. Might be a good way to pick up some more cash. Wrote down the number of the HR department. The person in charge of hiring models was an acquaintance and would likely see him on just my referral.

I also asked him to do a nude sit for me the next day.

The next day, Cole bowed out. The Art Academy was asking him to come in for an interview. I kind of smirked to myself. He was nervous about being hired. If he saw the usual nude models he wouldn't have been worried. They weren't, as a whole, pretty people. I imagine Mrs. Carmichael, the person in charge of hiring the models, would take one look at handsome, fit Cole and sign him up so fast his head would spin.

I mean really. Few artists want to draw the same homely people class after class. Most artists want to do attractive art. Not elderly men or nearly obese women.

Cole was in high demand. From the beginning classes to the last year classes every teacher wanted Cole to sit.

I didn't see much of Cole for about a month. Occasional mornings of stretching before his run.

Then he showed at my door one afternoon. Seems the art classes had moved past the figure drawing stage. Cole needed money again. Could I use a model?

I regrettably had to tell him that unless he was willing to do a hard core session, I just couldn't use him. Those erotic paintings and drawings were the money makers, not the vanilla half dressed or simple nudes.

He hesitated, then agreed to do some hardcore erotic poses.

I escorted him to the studio.

Got down to drawing him in various poses.

What a body. All whip cord lean muscle. Ripped stomach. A long thin dick, low hanging ballsac. Small bubble butt.

I had him pose on his back legs wide. Doggy style, hands pulling his cheeks apart, exposing his tight pink pucker. On his side, grasping a leg and pulling it up.

I was hard for the entire session. It's one thing to stare at a nude body, it's quite another when they are in raunchy poses.

When I was finished drawing him, I went to get his cash. Cole slowly pulled on his clothing.

Apparently, the money wasn't enough for him. He asked if I needed anymore poses. I shook my head no. I could only sell so many pieces featuring one guy.

Even one as handsome as Cole.

Then he threw me for a loop. Said he'd do anything for another couple hundred.

He blushed and then , he offered to suck my cock. Said he'd sucked dick in prison. Which brought all kinds of lurid prison sex scenes into my imagination.

I shrugged. No way I was paying two hundred bucks for a blowjob. Hell I wasn't going to pay two hundred for an ass fuck. And I told him that.

He asked me how much I'd give him for a blowjob. Told him I just wasn't all that into blowjobs.

He paused a moment.

Then told me I could fuck him for a hundred. Said he'd been cornholed a few times in prison too.

I paused in thought.

I could actually see where a pretty young man like him would have been in demand. On the other hand, the thought of taking my pleasure, without him being into it? Not my thing.

I could just give him the money. Two hundred wasn't that big a deal. Still? The idea of burying my cock inside his pretty little round ass was exceedingly tempting. I also was wondering why he needed the money so bad. If he was in trouble, I didn't want to find myself involved.

So I bluntly asked why he needed the money so bad.

I was sorely relieved when he told me he needed it to buy a used motorcycle.

At that point I offered to just give him the money. He said no. He'd earn his way, but not take a handout. Said he'd hold on to what little pride he had left, after being in prison.

So too proud to accept a gift, but not too proud to sell his ass for money. Men can be so strange.

That's when he upped the ante. For the last two hundred he needed, I could have his ass twice. Once now and one fuck at a time of my choosing.

Damn!

That was enough for me. Not a saint am I.

I went to my petty cash stash. I kept money on hand for my models. They always wanted cash. Got the two hundred. Handed it over.

Cole took the money. Stood. Stripped. Turned and bent over. Grabbed his ass and spread his cheeks, exposing his pucker.

I just shook my head.

"Whoa there ,Tiger!" I growled. " I appreciate the enthusiasm, but I like to savor the moment. After all of this time watching you stretch in the mornings, staring at you nude for hours, while I paint? If I'm paying this kind of dough, I want more than just a quick fuck. I'm gonna touch your whole body. Run my hands over every inch of your skin."

Cole looked surprised. I was guessing, in prison, there wasn't much foreplay. Drop drawers, stick in cock, pump away and finish fast. Before you got caught?

I pushed him over to the big wrought iron bed I keep in my studio. A firm shove had him laying on his back, his body on display in front of me. Even though I'd seen him naked several times over the course of his modeling, this was different. The anticipation of touching him , outside of his modeling, brought a whole new dimension to his nudity.

I reached into a box under the bed. Pulled out condom and lube. Cole's eyes widened. He licked his lips. Nerves or anticipation?

I crawled on the bed next to him. Brought my face close to his. Cole turned his face away. Right. No kissing. Too gay I guess. Had to maintain his hetero image. I rolled my eyes. The dude offered up his mouth and ass for money, but kissing a man was over the line.

Instead, I ran the palm of my hand over his hairy chest. That golden chest hair was incredibly soft. His wiry pecs were a nice combination of soft overlaying steel. My fingers found a pink nipple.

Cole may think he was all straight and macho, but his nipples were all for being played with. Those little buds were standing at rigid attention. The soft moan that escaped Cole's lips were another indicator he liked nipple play.

His plumping dick was another indicator.

This was the first time I'd seen Cole hard. Impressive. Long and thin. I estimate eight, maybe even nine inches. Small pink head.

I reached down to grasp his rod. Gave it a couple strokes. Cole arched into my hand. About half of it stuck out above my closed fist. Guess I needed two hands to cover his length.

I replaced my nipple hand with my mouth. Began licking and lightly nibbling that little pink bud. Cole began fucking into my hand.

At one point, I slid my free hand under his little butt. Felt the soft hair, over firm yet pliant muscle. Wormed a finger into his sweat damp crack. His hip movement allowed my finger to slide over his tight little pucker.

My finger in his crevice, seemed to excite him. He wriggled his hips around, almost as if he was trying to get it inside him.

Hmm? Cole never did say whether he liked giving his ass up in prison. His actions seemed to indicate he must have found some enjoyment in the act.

He certainly seemed to enjoy the stimulation. A big glob of pre um oozed from his dick slit and down to my hand. I used it to slick his rod, letting my hand slip up and down with ease. When another glob welled up I slipped my other hand from under him. Ran my index finger in the wet ooze. Slicked it up good. Reached back under, found his pucker and wet it with his own precum.

That brought another dribble. I used it to really wet my finger. I found his now slick pucker and pushed in the finger, his own cum easing the way. His hole opened up and I slipped all of the way in.

Cole bit his lip, trying to hold back a moan. Pretty sure it was a moan of pleasure, not discomfort.

I crooked my finger, searching for his prostate. Judging from the sudden tensing of his body, followed by a long moan, I found it. He pressed his ass down, trying to get more finger inside.

Question answered. Cole had learned to enjoy anal stimulation in prison. The proof? His moans and the humping of hips, as he began riding my finger.

A bigger spurt of cum, had me worried the man might shoot before I had a chance to bury my cock in him.

I pulled out, stood and started stripping off clothes.

When I dropped drawers, Cole's eyes nearly bugged out of his head. He swallowed hard. What can I say, I'm a grower, not a shower. Any unexcited bulge in my pants is mostly potatoes. My dick inflates to almost four times it's resting size. And we're not just talking length. A tall, lean guy like me? A skinny dick is expected.

Not an uncut cave man's club.

This would be a testament to how much Cole wanted the money. He wouldn't be the first man to back off once my fat prick was seen.

My answer came when Cole rolled over on his belly. His pretty little golden haired cheeks in view. Legs spread wide in invitation.

Oh yeah!

I suited and lubed up. Pulled one of his cheeks to expose his pink little pucker. It actually seemed to be twitching in anticipation. Squirted a generous dab of lube right on his little slit.

I knee walked between his outstretched legs. Slid an arm under his lean hips and lifted his lower body. Shoved a pillow under him with the other hand, putting his ass at the right angle.

I spread both cheeks and rested the tip of my cock on his fluttering little slit.

Pushed.

Cole's body tensed as the big head stretched out his ass lips. His hands fisted in the quilt. He gasped.

I paused. Both to let Cole adjust and to enjoy the heady feeling of breaching his hole. There is something I find so erotic about that first pop inside a man's bunghole.

Cole squirmed a bit. Maybe trying to adjust. He stopped when it caused a couple more inches to slide inside his gut. Then cautiously he began to push back. Sliding more of me inside him. Until he had seven inches of me buried to the balls.

God! What a feeling! His hot gut seemed to vibrate around and under me. His tight hole spasming around the base of the invader.

At that point I needed to move.

I began short easy thrusts. My cock must have jabbed his joy button each time. Cole was moaning with each little stab and withdraw. The thrusts lengthened. Soon long slow strokes rocked in and out of his loosening asshole.

Cole got verbal. In between gasps and moans, begged me to fuck his ass harder. Asked me if I liked plowing his hole. Told me how big I felt. How stretched and filled he felt.

I'm not much of a sex talker. More of a growler. But I surely do love a verbal bottom. One that let's me know he enjoys my fat cock reaming out his ass. Gives me a feeling of power. Adds to the whole experience.

Cole didn't want a slow easy love making. He wanted to be used rough. To be taken.

Maybe, mentally, if it was rough and not loving sex, it wasn't gay. I don't pretend to understand why some men want rough and some want gentle. Either way, my dick was happy to be buried inside man ass.

I pounded Cole for a good long time. I don't cum fast. Which has been known to cause multiple anal orgasms in some of my partners. Pretty sure Cole had two or three by his body's responses.

Cole's hand never strayed under to stroke his dick, so I was surprised when he yelled he was going to cum.

Yes! It's so fucking hot when I cause a man to cum hands free. Makes me feel like the best ass fucker in the world.

His body jerking under me, sent my own cum boiling up and out. I growled and pulled his hips back, burying my dick as far inside him as I could. Held his quaking ass tight against my groin. Fired wave after wave inside his hot gut.

I collapsed on his sweaty back. Both of us heaving in gulps of air.

We didn't lay like that long before Cole was wriggling out from under me. Too intimate maybe? I rolled on my back, my still hard dick pulling out with a pop. Watched as Cole dressed. He ran a shaky hand through his hair. Thanked me for the money and he was out the door.

Guess pillow talk wasn't an option!

A few days later, I saw Cole putzing around with a mid sized Harley. I walked over to check out his new ride. Cole sure was happy with his new bike.

Then he asked me if I ever painted a piece with a naked man on a Harley. ( I had actually, but I didn't tell Cole that.)

He had a tell tale gleam in his eye.

And he did owe me one more adventure in his tight little butt.