Date: Thu, 24 Apr 2014 11:02:28 -0400
From: Richard Dule <dickydoo2@gmx.com>
Subject: Jail Times 1

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 that`s 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...