Reader Advisory:
Rating: 18+, due to mature content, coarse language, and awesome, kinky, wonderful gay sex. All characters are real, but the fantasies are what the author wanted to do with them...
Jail Times
The Don 1
Along with three other prisoners, the four of us, fresh from local jails, were herded into the ancient Don Jail. And when I entered and looked around at the full range of the varous inmates staring at me, I felt terribly vulnerable and very alone.
My only knowledge of jail being what I had read or seen in the media, not knowing what to expect now, especially from what I had heard about this piece of antiquity.
But first I'd better explain the system for those unfamiliar with it. After being arrested and held in one of those small local police station jails for a day or two for paperwork and attempts at intimidation by the cops, you would be transferred to the Don jail.
It was a larger jail with more facilities, like in-house food, exercise etc. where one would be incarcerated while attending court and to await sentencing. After sentencing, you would then be transferred to an even larger correctional' facility like the East for rehab` (a bit of a joke) and to serve out your sentence.
Oh, yeah by the way, as I think you may have guessed, since this is on nifty.org I'm also gay. Yes in the closet though and more so here, as I didn't think that fluttering my fingers in the shower would be the safest thing to do. But it turned out it didn't seem to be that big a deal.
For instance, as we filed in, an inmate Frank approached me and asked if I wanted to be his cellmate, which was a relief because there were some other pretty tough looking characters watching us. He was 40 and the next day he confided in me he was a closet gay, and must have had good gaydar as he said he figured I was and gave me a knuckle bump.
Also it wasn't long before I eventually befriended another inmate who was openly gay and who was also HIV+. They didn't seem to bother him, in fact he was quite popular and when he was transferred, everyone on the range was at the gate to say goodbye. I guess I was pretty transparent at least to the gays on the range.
But the facility was pretty tolerant as there was a senior tranny guard that the government paid to have a sex change and wore
a skirt. Also, several cute tranny inmates passed through, obvious by their fem appearance and hairdos, and one in particular was special. But that's another story.
So I didn't feel as alone as some weeks passed by, getting used to the regimen. Then one day, a new inmate, Diego, was brought in and he quickly caught our (gays') interest, as most newbies do, especially when you are a chicken and look so young.
But he had to be at least 18, so too old for a juvy (juvenile detention), and to top it off, he was really cute, somewhat on the thin side, a little shorter than me, maybe 5" 9", and a bit Latino with slicked back black hair, full lips, sparkling black eyes, no facial hair and was completely smooth as I was to find out. They put him in with a pretty rough Russian who was in for weapons charges.
The next day about a dozen of us went to court from our jail. There were eventually about 25 of us in that `tank' or holding cell, but as the day wore on, the number dwindled as they left after their appearances, until there was just Diego and I. Around these others I noticed he had seemed pretty street smart, quite friendly and very confident.
Finally we were called up to court and when we got back to the tank, they had put on a special van for just the two of us, it was small, not the usual paddy wagon but a more comfortable.
With just the two of us, we quickly became quite friendly, he could make you feel at ease, was a smooth talker but as we were chatting away he suddenly looked at me seriously, "Are you gay?"
I normally would have freaked, but having spent our day and trip together and with a developing relationship, I was comfortable in replying, "Yep, for sure, and figure you are too. So I guess our gaydar is working good!" and we both grinned, but because we were cuffed to each other, we couldn't knuckle bump, so we had to bump the back of our cuffed hands together.
When we got back to the jail, there were just the two of us to be processed, and a cute young guard took us into a search room for the usual strip search.We stripped and man, when Diego dropped his boxers, one huge hunk of lumber tumbled out.
The guard looked as surprised as I was as we stared at it and when he looked back up, Diego gave him a smirk, which kinda embarrassed the guard who quickly looked away, then turned and smirked back.
Diego tugged on it, then rolled back the skin on the shiny knob and smugly said to him, "Just want you to see I'm not smuggling any pills or anything" and did it slowly a couple times as the guard looked back down and chuckled while he snapped on a latex glove.
"Oh Goody, a cavity search! You are so sweet!" Diego added as he turned around, bent over, spread his feet, then spread his cheeks with his fingers, and looked back overhis shoulder, "Help yourself, and you can put any old thing in there your little old heart desires good lookin'"
The guard put his hand on Vinney's hip then buried the index finger of his other hand in his ass and Diego moaned softly, his head bobbing, then moaned a little louder, "Ohhh... so nice, more..." and the guard quickly
looked back toward the door, then obeyed, giving him a couple more.
Diego looked back over his shoulder again, "...I think you may have missed something... better use... two fingers, K?" and smiled invitingly.
The guard looked over at the door again, then at me so I shrugged and we smiled at each other.
I was sure enjoying it, and I know the guard wouldn't want to admit, but he was too, because he doubled up on his appendages and worked them in several times as Diego bobbed his head while he moaned, then the guard pulled them out.
Diego turned and lazily looked down. His cock was swollen, thick, on its way up and he grasped it and slowly jerked it, rolling his hoody back and forth, "Now see what you've done to it. Woke it up and now it wants some exercise" and took his hand away and it was semi,horizontal and a beauty.
The guard gave me a just cursory glance for a search, and I was fighting a boner too, which Diego noticed and raised his eyebrows when he saw it. The guard tossed us new boxers and jumpers and we dressed, then he led us to our range.
Diego smiled warmly at him before he let us in, "Do you make house calls? I'd sure like you to do some more examining but with that love finger of yours though" and looked down at the guard's crotch which looked like it was stretching down the pantleg.
The guard didn't get angry though and I wondered if he was going to have similar fantasies as the ones I was gonna have later when I had my nightly release.
The next day I told my gay friends what happened and the size of Diego's junk and also his story that he relayed to me in transit, being quite casual about it, and not the least bit apologetic. He was in on dope charges but went on to say he was also a `Rent Boy', and with his almost 8" cock, was making good money at it. Like $50 to get blown, $100 to fuck and $200 to get fucked.
We now played closer attention to him. The 3 showers were
open to the range and we were supposed to wear our boxers when we showered.
The first time he showered, he turned away, and seemed to be pulling down the front likea lot do when they want to wash their junk, but instead, he dropped them all the way down and stepped out of them, worked on his joint, then turned with a raging super hardon waving!
He had his head leaned back, the water running over his face, his monster cock waving and the range went silent as a few of us gathered aroun and stared. He dried off as he smiled at everyone and there was no harassing him because everyone was either envious straight, or desirous gay. But with that flagstaff, he was also obviously more man than anyone else too.
He always walked around with the waistband of his boxers down so the base of his cock and smooth pubes showed. Every time he showered though, he sure had an audience, 'showing off his bone and one day our search guard was on his way through and stopped, said nothing, but had a good long look and gave me a small smile.
About a week later, Diego`s celly moved out and he came down to my open cell where I was reading, ``Hey Mitch, wanna be my new celly? Butch, that Russian asshole, moved out"
I liked his soft voice, it was a little higher register which suited his short lean body, "Wanna?" it was a dream come true!
"Hell yeah Diego, sure would, that would be over the top bro!"
"Awesome!" he said and gave me a knuckle bump, "you're hot!" then blushed a bit as he looked away for a moment then grinned back at me, "I like a friend thats a little more mature and experienced and I've been wanting to have some fun, I think you may be up' for it too" and grabbed his crotch.
"Don't have to ask me twice! I'm up all the time!" and I squeezed mine, then we checked in at the guard booth. Our search guard was on desk duty, and he jotted his move down
in the book and snickered as he nodded, "No probs, just uh... not too much noise now" and winked.
I started packing my gear when my celly Frank came in our cell, "Yo Frank, Diego wants me to be his new celly, do you mind?"
Neither of sexually appealed to the other, but liked talking gay talk, so he said, "Hell no, wish it was me, but you gotta promise to tell me what you guys get going, K? And oh, here" and he tossed me several condoms, "I took these off the nurse's cart, they're free, I had them for my last celly, he was a lot cuter than you!" and slapped me on the back.
So here I was, horny as a dog with two pricks, and setting up house with my new stud. What could be cooler?
He was quite neat, bed made tight, and was rearranging everything when I lugged in my property. I dropped my sheet bag
down till he finished, then he plunked down on the fixed table seat, and leaned back against the wall to watch me unpack while we chatted.
"That Russian was a fat dirty pig, like sloppy too, and when he yanked on his pathetic dick underneath me, the bed would rock and he'd squeal like the pig he was. When I'd start to jerk off, his imagewould pop up in my mind and I'd go soft!" and giggled.
I had been listening and was bent over, fixing the bed when he said, "Oh yeah, that's what I need!" and I turned my head sideways and looked back over my shoulder at him. His feet were
spread and the tent in his boxers was bouncing up and down and he was grinning, licking his lips.
I realized it was my ass he was staring at, so I took a quick glance over to the closed door. We were on lockdown for a range repair for an hour or so, so there were no inmates or guards outside, so I stayed bent over, pulled the waistband of my boxers down below my cheeks, reached back and spread them.
"Shit! You hot bitch you! I gotta taste that!" and he went to the door and looked back and forth between the bars, then returned, knelt down, spread my cheeks with his thumbs and started tonguing
me. Man he was good, I snapped hard real quick.
He circled my pucker muscle with the tip of his tongue, then pushed it in and out, then pressed his lips hard around that love ring and sucked hard. Awesome!
He pulled back and stood, "Man I love your taste, I better tease
my buddy with what he can look forward to" and held his waistband
down with a thumb, peeled back his skin and rubbed the damp
knob around my hole several times, then snapped his band back up, "He likes it! Better no turn your back on me too often"
I stood and pulled my waistband back up over my ass and turned, fully tented. He reached down and squeezed the tent, "Shit bro, I gotta taste this sucker too. I haven`t had a cock in my mouth forweeks now and my throat is so dry, I need some lube"
He went over and checked the range again, "There's no one out there and it looks like they will be a little longer, but someone may come up the lane, so I know what we do in case"
The range was a long rectangle, entrance gates at one end, barred cells down one side, showers and toilets at the other end and opposite the cells, across the range, there was a wall of bars about 6' from the cement block wall so it made a hallway or lane where the guards could go down and look into the range or across at us in our cells without going in the range.
The bunks are lengthwise on one side of the cell, so he had me stand beside the bed, back to the door, at the end nearest to our door and I leaned against the top bunk, my elbow on it, my head resting on my hand and my ankles crossed. Casual like.
He then sat on the edge of the bottom bunk almost hidden, so from the range all you could see was my back and just a bit of his side. I was looking down at him as if I was chatting to him on the lower bunk.
He pulled my waistband out and over my throbbing cock and snapped it under my balls. "Oh yasss" he said as he licked his lips, "when I saw this in the search, I just knew I had to swallow it" then furled my hoodie back, "and I'm glad you aren't cut, I love a tender juicy cock, not one of those dry tough and wrinkly ones. Mmmm..."
...to be cont'd if you want...
didkydoo2@gmx.com
Some other stories in young friends like Classy Art, Challenged, Live
Health Club, and others if interested...