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Prison Sex

Author: Alex –

From my bunk I could see into the cell across from mine. It was occupied by this cute looking blond kid with a baby face and a sexy bubble butt. He was new to the county lock-up, and judging from the fear in his huge, blue eyes, it was safe to assume this was his first time behind bars. As usual in mid-July, the cells were hot as hell. The dim light from the corridor cast a soft, warm glow over the boy’s resting body. The only thing he wore was a pair of boxer shorts. The rest of his slender body lay exposed. My mind began to wander as I lay staring at the new kid. He couldn’t have been more than eighteen. I could hardly wait for morning to arrive so I could check him out, close up, in the showers. In the mean time, I could only rely on a vivid imagination to fulfill my fantasy, and the lust burning between my legs.

Pressing my naked body against the cool steel, I stuck my eight inch cock between the bars. My man flesh pinged like a homing beacon, lusting for the vibrant, young flesh that lay so near, but was impossible to reach. A generous flow of pre-cum lubricated my hand as I vigorously slapped my throbbing cock. The lewd sound of wet, pounding cockmeat got the kid’s attention. Only his head turned to investigate the seductive sloshing of my jacking off. His sensual eyes widened as he stared down the muzzle of my loaded weapon. “Show me your cock, kid. I want you so bad. This is for you, sweet thing,” I grunted, as I launched long whipping strands of gooey spunk into the corridor. The kid turned away, refusing to acknowledge my gesture of friendship, but I wasn’t insulted. I knew he was scared. His fear would pass, once I took him under my wing. The current population in lock-up was down, there was just me, three other inmates and the kid. It made the job of protecting my prize a whole lot easier. I wasn’t about to share that cherry ass with anyone. He was all mines. The next morning all eyes were on the kid as he stepped naked into the shower. Christ, he had a body that would have given a straight arrow a hard on, and I wasn’t altogether straight to begin with.

It didn’t take long for a couple of the guys to put some moves on the young, fresh meat. They quickly had him pinned in a corner groping his firm, silky, baby smooth ass. “Please stop,” the kid pleaded, attempting to push their hands away. Fortunately my reputation had preceded me. I got the dogs to heal by simply clearing my throat. With his back to the wall, he stood cowering, hands cupped tightly over his budding manhood. Terrified eyes expressed his silent gratitude.

“Don’t worry,” I said, putting my hand on his trembling shoulder. “You can relax. They won’t be bothering you anymore.

“I guess I should thank you,” the kid stammered, dropping his hands to reveal his alluring cylinder of boy meat.

“That’s a start,” I said, admiring his uncut cock. He was the most beautiful person I’d seen in a very long time. “I guess if you want to”…. I put my fingers to his soft, full lips, stopping him before he could finish his thought. His expression was one of naive bewilderment. I wanted him so bad I thought I would burst apart at the seams, but now was not the time, nor the place. “We can talk later. Right now, you’d better get your shower. You’ve only got ten minutes.”

The kid and I stood side by side, lather rippling down our bodies. I couldn’t get over how his smooth, wet skin seemed to glow. To make him feel more at ease, I tried to be discreet in my observations, but I wasn’t overlooking a single inch of his glorious body.

With envious greed, I watched his soapy hand glide down his flat, washboard abdominal to tend his luscious limp organ. I held my breath as his thin fingers retracted the generous flap of soggy foreskin sheathing the crest of his cock. The water cascaded down his satiny torso, washing over his sensitive, purple knob with a cleansing caress that made him shiver. The wispy tuft of blond man fur surrounding the root of his ivory tool lay wet, and matted, against his pubic bone. His tender, young balls hung low in their velvety pouch, weighted heavily with his abundance of succulent boy cream. I was deeply obsessed by the spell this teenage jock had cast over me.

The kid tried to divert his eyes from the thick slab of horse meat rising up between my hairy thighs, but I caught him staring. I sensed the adolescent-like curiosity trembling in his hands as he fondled the slippery mounds of his narrow, round buttocks.

I was met with little resistance as I reached for his hand and placed it on my hot, pulsating cock. “You like dick, don’t you, kid?” I asked. He pulled his hand away, but I knew the truth. I could see it swelling between his legs. I put my mouth to his ear. “Don’t worry, so do I. Your secret is safe with me.”

That night I made a deal with the guard that would allow me to visit the kid in his cell. My intentions were purely sexual, and the guard knew it, but that sort of thing happened around this place all the time. A few bucks in the hands of the right guard, and you could have any piece of ass in the joint.

When he heard his cell door open, the kid sat up, drawing his knees up against his chest. He didn’t seem at all surprised to see me. He may have been young, and beautiful, but he obviously wasn’t stupid. I could tell just by looking into those baby-blues, he knew exactly why I was there.

The cell door closed behind me and the guard left us alone. “What’s your name, kid?” I asked.

“Patrick. And you are?”
“Simon.
“How long have you been in here, Simon?”
“Six months.”

“I appreciate what you did for me, you know, this morning in the shower.”

I sat down on the bunk beside him, putting my hand on his knee. “Glad to be of service, kid. I don’t think you’ll have anymore trouble with those guys. They know not to fuck with me.”

I felt goose bumps rise up on his hairless skin as my hand crept up his thigh. “I saw you last nigh in your cell,” he said. “I’ve never seen another guy jack off before.” “Welcome to jail, Patrick. You’re probably going to wind up seeing a lot of shit you’ve never seen before.” My hand had nearly reached his crotch when he jumped up from the bunk and put some distance between us. “What is it you want from me, Simon? I’m not gay, if that’s what you’re thinking.”

I shook my head and laughed. “Why is it people think two men have to be gay to enjoy one another’s company? I’m attracted to you. I’m tired of sitting alone in a dark cell beating my meat.”

“I don’t think I can do what you’re asking,” Patrick mumbled.

The sex story posted below was rated the most popular sex story on TheWhack for October, now I want to see if you guys think its worthy enough of being on the top 10 best sex stories of the year, post your comments below or vote here.

My Masturbation:

It’s a balmy 70 degrees outside today in the month of February on Florida’s East Coast. I’m sitting outside overlooking the Atlantic Ocean watching the sea gulls fly off in the distance and hearing the roar of the ocean waves crashing on shore. There isn’t a person in sight for miles as I sit in my lawn chair with no shirt on soaking up the mid-day sun. A nice gentle breeze filters through my hair and the smell of fresh sea air is apparent. As I sit there in a state of complete mental relaxation a totally powerful, incredibly provocative, and alarmingly erotic mental image takes up residence in my mind and consumes my thoughts. I feel strong stirrings beginning to take place in my groin. I look down towards the porch and realize my cock is hanging out of my boxers dangling back and forth with the breeze. Before long I notice my nipples are as hard as pencil erasers. I look down and see tiny droplets of precum drizzling from the tip of my penis and landing on the porch. I start to touch my ball sack. It’s so warm, so soft, and so hairy. Then I run my fingers up underneath my balls and towards my ass to touch that area between your nuts and your hole feeling the intensity, back and forth, back and forth. My cock is now rock hard sticking straight up towards the sky.

I move my right hand slowly in a circular fashion stroking the tip of my cock to massage the precum all around my cockhead. I jerk off faster now and my balls start banging up against the seat of the chair all the while my left hand is fingering my hole in and out with my index finger. At the same time my right hand jacking my cock up and down. I start to feel a tiny quivering inside my groin area signaling the start of an incredible orgasm. I feel it increasing slowly yet steadily rising, gaining power in exponential intensity. I feel my ball juices start to flow into my cock like a stopped up drain fills with water. Right hand up and down, left hand in and out. I look down and see that my nipples are extraordinarily hard right now sticking out as if to pick up something writhing in pleasure. My head falls back in the chair and my mouth opens up gasping for air. My eyes are opening slowly and then closing again, the world seems to dim and fade, spin and stop. I can’t help it; this feeling is so inundating and alive. A rush from a distant dimension of my fantasy caught up with reality. My ball juices have filled up my penis like an overflowing swimming pool.

I push my left index finger farther up my ass massaging my prostate. I feel minor convulsions emanating from inside running all over my body, like a tiny minuscule amount of raw electricity suddenly fused with my essence and started to dance. My chest continues to pulsate and all the muscles in my body flex in ways I never thought possible. My right arm and wrist tighten as I jack my cock up and down utilizing all the excess precum as lubricant. Then I feel the futility of holding back as the urge to cum is thrust upon me. I feel the entire universe penetrating my soul in an instant as my load shoots straight up and hits the top of my forehead as I rock back and forth in the chair. Then the second squirt of cum splashes on the top of my chest and slowly heads down towards my hard left nipple leaving a trail of cum behind it like a drop of water running down a slide. The third squirt lands above my belly button running down and getting tangled within my pubic hairs then falls down to my ball sack. The forth and final squirt drenches my hand and plops down onto my bare feet.

My toes start tingling as the warm substance hits home. The euphoria I feel now as the universe twirls my soul into oblivion is still very much as powerful as it was at the start of my orgasm. All it is that I consciously notice is the world goes dark and time stops. I feel a longing and comfort in wanting to live in that moment forever. Slowly the lights brighten and time slowly restarts……then I go grab a towel.

Author: unknown

…I didn’t see much of them the following day as they all went out at lunch time and didn’t get back until night time, a little worse for wear.

Within minutes I saw the bedroom light switch on so I ran upstairs, sat in what had already become my favourite chair, and looked over to see which of the lads occupied the front bedroom. My heart skipped a beat when I saw that it was the slightly larger lad with the chestnut eyes and handsome face.

He switched on his television set but I couldn’t see what he was watching as the telly was just under his window, but I could see him perfectly well as he sat down on his bed where the headboard was at the far end of the room facing towards me. He lit up a cigarette, opened up a bottle of Becks and drank straight from the bottle, while I drank in his beauty. Once he’d finished smoking he carried on watching the telly, only this time he spread open his legs and started to caress himself between his thighs just below his shorts.

I sat in wonder and amazement not believing my luck. I felt the tightness in my jeans as I started to swell up. Using all my will power I restrained from touching myself, wanting the sensation growing up in me to last for as long as possible. I carried on watching as one of his hands now slipped under his tee shirt and he began squeezing and pulling on his nipples. His other hand rubbed his erection through his cotton shorts. His eyes were glazing over but he never took them of the telly.

Cursing, I realized I needed the toilet so I ran to the bathroom quickly and relieved myself. By the time I’d got back he’d stripped off all his clothes and was lying there stark naked except for a white jock strap that looked ready to rip open any second with the strain of his erection.

Sitting forward in my chair I took a closer look through my binoculars, he was now stroking his balls. I watched as he circled his cock head with his thumb, smearing his juice all over and then to my excitement he put the same thumb into his mouth and sucked off his own pre-cum.

I still refused to touch myself, keeping up my heightened state of arousal. He slipped off his stained jock strap and revealed a thick uncut penis about eight inches long. Slowly he began pulling his foreskin up and down picking up speed as he went.

I almost shot my load in my underpants at what I saw next. Laying on the bed he pulled his knees up and spread them wide giving me a clear view of his tight crack, but not for long as his hand came down and he inserted one of his fingers all the way up to his knuckle without any resistance.

All my restraint and will power went out the window as I watched him insert another finger, I quickly stripped all my clothing off and grabbed my aching hard on and began jerking myself off as I carried on watching.

He was now kneeling on his bed, one hand stroking his hard cock and the other one was around his backside. I couldn’t see what his hand was doing as his front was to me but I could easily imagine that a couple of his fingers were deeply embedded up his hot hole as he began moving his hips from side to side then up and down.

I couldn’t hold back any more and as I felt the first throb of my ejaculation I saw that he was coming at the same time. I watched with curled toes as his cum shot high in the air and splattering his chest and stomach as it came back down. I didn’t stop coming the whole time I watched and I could feel my warm cum dribbling down my own chest and stomach.

For the next two weeks I couldn’t wait to get home and into my favorite chair. Every night the lad with the chestnut eyes would lie in his bed and play with himself and afterwards I would watch him as he slept. One night I came three times as I watched him insert a huge dildo up his backside.

Sadly, this was short lived as they eventually bought curtains, but sometimes I still sit in my favorite chair in the hope that they are left open.

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