True life events, my 2nd encounter

#Gay #Teen

2.8k words | 3 | 4.83560

Hells

This is my true life experience, this is another part of my life that “helped me” understand myself.

This is my true life experience, this is another part of my life that “helped me” understand myself.

If you read the first part this will be a jump from then until I was 17. You can understand from an early age I had some family issues. Those never went away, in fact it followed me right to this point in my life as well.
I became one of those teens that just lashed out in anger at the whole world, and it landed me in more than I care to count incidents with law enforcement. I was currently on probation, sentenced under what is called a YOA ( Youthful Offenders Act). This is where me, being 16 at the time was sentenced for stealing a family members car as an adult, but I was still a minor. That means if I violate my probation in any way I can go to prison not juvenile facilities. Well I think my first violation came the first month in, after that it was just me doing everything other then what I should be doing. School was not working out (and I had to be there per the probation), no job, drinking and fighting.
By the time I was about 9months into probation, I showed up to report they handcuffed me and put me back in front of a judge a week later. I was 17 by then so the judge made sure to tell me “I am going to show you where your life is heading towards”. With that I was off to “Adult” prison at 17.
Now like before I was scared to death, you heard stories of what prison’s are like and I already knew some of what goes on at night. I spent a month in what’s called ” Processing Center” this is where they take your street clothes give you state issued everything, then make you fill out a bunch of papers, sign your name, take pictures and then shove you into a small 1 man cell. Your locked down for 72 hrs off the jump, no calls, no contact with other inmates, and let out for 1 hr a day for Recreation and a shower.
Worse mental mind fuck in my life, isolation with only your own thoughts to contend with. For me this was going over all the ways I let myself get caught, then it was the “WHY”, after that came the regret over and over. When you have to do time inside your own head it’s makes doing time seem like eternity.
I finally got the notice ‘Moving Day”! I was being placed in with the population at the newest Adult Corrections Facility, just built a year ago I was told. Walking in the main area it smelt like new paint, glue and cleaning solution. Once through the main front office you go out the back into a massive open area with several buildings each with a purpose and sidewalks that marked a path to each building and a 15’ double fence with razor sharp wire looped over the top around the whole place.
As we walked past the “Cafeteria” I was told the times we were to come there to eat, if you missed a time it was your lose. Then to the “Commissary”, here I get my personal hygiene once a week if I wasn’t able to buy my own from the prison store. I was also handed 2 extra sets of clothes, sockets and towels and 1 laundry bag with my state ID number on it. Laundry is turned in on Friday and returned Saturday you must pick up your bag.
I was shown the Chapel for worship service, recreation area’s and finally my dorm building. Doors are unlocked at 8AM and lock down at night was 9pm, but you had to be in your room by 8PM. The cell was like a dorm room, 2 beds ( attacked to the walls and floor), a stainless steel sink/toilet with a stainless steel mirror mounted above the sink, and finally a table from the wall and a small stool like also mounted to the wall.
At first I did not have a room mate ( I liked that ), but that lasted only a few days. I met David, he was older then I was by 3 yrs and like me new to this environment as well. I had been reading the handbook and we helped each other with the daily items to pass the time.
After a few weeks went by I started to spread out into the yard area, I got a job in the work shop and was getting paid to work, this helped me get some store items little by little. I was always told ” Never take anything from anyone even if its offered”. I had heard about a few things going on and seen a few too, but as you know on the inside you don’t See anything, Hear anything or Speak/Say anything!
So when i seen a guy get stabbed with 1 half of a pair of scissors, I turned around and went right to my room. Later when told by a Correctional officer I was seen there and they had me on camera, I told them exactly what I knew, NOTHING!
Not even when a guy was playing cards and made a mega bet with his ass to cover what he was short, did I mention I seen the whole thing from my room when asked. He lost the bet, went to the Correctional Officer’s ( CO) and reported the game to get out of the bet. He was found in a hall way in another dorm he had been used with a mop handle.
All this taught me to keep my head down and do my time to get out, I had up to 1-6 years. Working on my GED I met Dennis. He was 34 yo, 6′ 3, Brown hair with military hair cut, Blue eyes and in over all good shape. I was 5′ 11, Hazel eyes, dark brown hair shoulder length, and was maybe 180lbs ( former DT in HS football when I went).
Dennis met with me in the library where I signed up for help studying to take the GED. We hit it off great, we met at the library every other day for a couple of months. He helped me take my practice GED test and then we worked on the areas I was lacking. One day I seen him out in the yard and we got to talking he invited me back to his room for some cookies he just got in from a family member ( you was allowed in other buildings but you had to be out before 5pm).
So I went to his room, he shared the cookies and we talked more about school, why we were locked up, my YOA and he was in for “Delinquency of a minor”. He said he was smoking weed with a minor that said they were 18 but turned out to be 17,16 and 18. All was good in my mind, nothing but being friends and hanging out. It turned into me visiting his room almost every day even up to time to leave at 5pm.
We talked about everything, life, girls, family and how NOT to come back to prison again. With all conversations with guys, when your talking about girls sex comes up. Now I had some experience with girls my age a couple a year or 2 under, and 1 older woman. Dennis told me about being married, some chance encounters with some “questionable” girls. The question was asked about M on M sex. My answer was a quite “No”, and I was not into it. Dennis confessed he had some encounters with a few guys nothing to brag about, but we did not have to talk about it if I did not want to. And the subject died at that time.
Now I had been in for about 11mounths at this point and got a notice I would be able to get out in a few weeks. I had spent most of my time doing my job, getting GED done and hanging with Dennis.
So when I showed up to tell him about my news of getting out he was excited for me, after a few minutes he said ” I got the perfect thing to celebrate with, just got it in a few days ago”. He looks in some stack of books and magazines tells me to sit on his bunk ( nothing new we have sat here before) as he turns around he hits my head with a Hustler magazine and drops it in my lap. He then sits on the bed and kind of leans on the wall with his head.
” Check this out, I know it’s been a while since you seen anything like this”. I see a sweet set of tits on a perfect 10 of a woman, something I have not seen in over a year. I open the mag looking and wanting to see more, and more, legs spread wide open full view of a tight looking shaved pussy, another of her bent over ass spread and then with a guy holding his huge looking cock on her ass.
I got super hard, we all know every guy has his alone time and jacks off, I was one of those more then once guys. I thought about sex and wanted it badly since I knew I was getting out in a couple of weeks it got worse. I am not hung, only 7.5 inches cut, about 2 inches girth, but when I get hard I stick straight out not up like some guys.
Dennis noticed and said he got the same way when he seen her to, as I went through the magazine I was straining to not rub myself. Finally Dennis said ” Fuck dude, IDK how the hell you can not want to just whip it out and rub one out. I know I want to, hell I am, hope you don’t mind.” With that Dennis pushed his sweats down and pulled out his 9in cock and it was hard as hell already had the tip wet.
I said ” Well fuck it’s your room, you can do whatever you want in it, don’t mind me my eyes are full over here”. Dennis leaned back and slowly stroked his cock as I went through the pictures one by one. I am not sure why but I pulled my dick out and started stroking myself, but I was taking glances at Dennis as he played with himself.
Dennis finally asked me if I had ever let a guy jack me off, ” Hell No” was my reply. ” Don’t knock it until you try it” Dennis said. He offered to stroke mine if I would stroke him, a different hand then your own feels better.
I said ,” IDK man, I told you I am not into that kind of stuff, besides you get a rep around here with that and it’s bad all around.”
Dennis, ” I know what your saying but it is just use, you got 2 weeks try it you might like it, if nothing else it’s just a hand job”.
On with that Dennis reaches over moves my hand away and begins to stroke my dick, I did not move just sat there looking at the wall for an answer. Dennis moves my hand to his dick and I wrap my hand around it, he is hard, hot and feels … nice. I could feel his pulse as I ran my hand up and down then over the head a few times. I turned and was just staring at his dick as I stroked it.
Dennis slides forward and tells me to stand up, still holding my dick and I made sure to get a good feel and stroke of his in my hand. He says ” Got to move over to the sink, cant make a mess in the floor or on my bed”. I let him go and move in front of the sink/toilet, Dennis is behind me still stroking my dick. My sweats are pushed down more, Dennis tells me to move my legs apart a little so he can rub my balls some.
I move and make the adjustment, Dennis reaches around and pulls my balls up and hold them then grabs my dick and strokes it. I am really feeling the hand job, he has my pre cum from the head down to my balls now slick. Then I feel his dick head slide between my legs and push on my balls, each stroke he takes he pushes in and out of my thighs.
Now some where in my mind my first thought was of Travis, and his cock in my ass and how I told him to fuck me that night. I am not sure if I did it out of want , need or reflex, but I moved and Denis’s dick went between my ass checks, right over my ass hole up to my lower back. I didn’t flinch and Dennis noticed, he moved back between my legs and then he let it slip out and run up my ass, as he passed my hole I pushed back a little.
He really noticed that, while still stroking my dick he used his other hand to rub the head of his dick up and over my ass hole a few times. All I could think of was wanting to feel that dick inside my ass, just like Travis did. So I leaned over the sink a little more and pushed back again, this time right at him.
Dennis stops jacking me pushes one side of my ass check over and placed the head of his dick right on my puckered hole, I did not move and felt the head pop into my ass. Dennis stops and waits, I guess he feels me relax then he pushed in some more. It has been several years ( 6 to be exact) since I have had any dick in my ass. I could feel the burn coming back but yet I also felt like I wanted this, maybe needed it or I wanted to make sure I gave Dennis something for all the kindness he showed me.
That’s when I push back taking him all the way in, put my head down and say “Your in now, don’t stop please.” Dennis pulls back and begins to fuck my ass, he gets a nice pace going, I am just holding to the sink. I thought it was 20 or 30mins but it was really like 10 mins and Dennis is picking up pace and I feel his dick swell.
Dennis says ” I am about ready to cum, you want it or what?”
“Yes, please cum inside me I can feel your close it’s so biiiigg”.
Dennis is ramming that 9in dick in and out of my ass as deep as he can with each stroke til BOOOOOOM! Hot liquid magma fills my guts, 1,2,3,4 streams of hot cum. Then his dick just pulses in my ass. He goes to move and I say ” Stop, hold on let it sit for a minute”. I didn’t want to let go of this feeling, I wanted it to last longer.
Dennis goes soft and slides out of my gapping hole. I look down and in the sink where Dennis drove me into as he was cumming, I had unloaded a nice load myself, just from being ass fucked by another man.
We get cleaned up, I sat down on the toilet and let all the cum run out my ass, and wiped up. Dennis looks at me and said ” You lying MF, you said you was not into that kind of thing. Sure looks to me like you like taking it up your ass”. I said ” We need to have a talk about that, but later it’s getting late”.
I went back to my dorm room wondering WTH I had just did and why. I was not sure what caused me to give in like that or allow it. I did know I ended up jacking of thinking about his hot dick pushing deep inside me, a couple of times that night.
Later I told Dennis about what happen at the Boys home and how confused I was. I never let him fuck me again ( was to scared of to many things back then ), but we did jack each other off and I let Dennis give me my first ever blowjob from a guy.
I got out, got my life in order because I did NOT want to go back ever again. YOA is sealed once you turn 18 and so was my criminal life. I chased an education and made more then one mistake with women, but who hasn’t. LOL

True events as best as I remember.

Want to talk dragonheart7032@comcast.net

🔞 Candy.AI 🔥 AI Sex Chat – Roleplay, Erotic Stories, Try for Free 🕹️

Leave a Reply

Your email address will not be published. Required fields are marked *