My First Year in Prison - Chapter 01 (Patreon)

Tyler is happily engaged when his life takes a turn and he ends up in California State’s Prison. Surrounded by bad boys, hot guards, and a lot of testosterones, is Tyler going to manage to keep himself out of troubles?

This story is a sequel to “My First Year in College”. The action takes place 9 years later in a whole different setting. You don’t have to have read the first book to enjoy the story but I do think it will better your experience.

This is purely fictional and all characters featured are above the age of 18. Enjoy.

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My First Year in Prison

Chapter 1: Inmate #328

“Take off your clothes, inmate.”

It was surreal. Being called an inmate. Being there.

I was looking at the dirty floor, doing everything I could to avoid the creepy eyes of the guard.

Guard Falcon was bald, had broad shoulders, a furnished grey beard – he was only in his forties but he looked much older than that -, and he was holding his baton against his large thigh.

He kind of looked funny, like a Pornstar from the 90’s, but still, he was scaring me.

“Are you deaf, inmate?” He barked at me.

“No… Sorry… I…”

What was I expecting? A changing room or something? Of course, I would have to get undress right before the guard’s eyes.

I can imagine your surprise my dear reader. You are probably wondering how the fuck did nerdy Tyler Braxton end up in prison? Well, I have asked myself the same question for a long time.

I will have time to go in full details on why I ended up stripping in this cold room in front of guard Falcon later in this tale, but as you can probably guess if you have read my previous story, my arrest had a lot to do with a hot guy crossing my path.

In this case, his name was Will Torres, he had tattoos all over his left arm, and he was actually a patient of mine. He also turned out to be a drug dealer.

I did end up becoming a therapist in Los Angeles (lot of neurotic people there!) a few years after I left Creepside College and the East Coast. Too bad I did not get to practice for long though. I guess sleeping with your patient would do that to your career…

Anyway, there I was, about to be locked up for about a year and I had no choice but to obey the guard.

Still avoiding his gaze, I took off my sweatshirt and put it on the single chair in the room.

I was more comfortable with my body now. At 28, I had managed to find a good balance between my fiancé at the time, Griffin, my patients, and taking care of myself and my body.

Griffin was not much of an athlete but he was a runner and he got me to jog as well. It helped us both to stay fit. At first, I hated it. I reluctantly joined him - mostly to watch his cute bubble butt bouncing in his tiny green shorts -, but with time, running became part of my daily routine.

I would often recommend to my patients to exercise so I tried to follow my own advice for once.

Griffin was quite hairy and generally very masculine. His grandparents were Irish on both sides and he had come to live in the US after her mom moved here when he was a kid.

Not only my Irish fiancé was handsome but he did seem like the perfect match for me. He was caring, affectionate, and funny. Sexually, he was a top and I had found out years prior that I was definitely a bottom. His dick was not that big but he was certainly good enough at using it – it was not rare he would give me multiple orgasms a night. We would often end up cuddling, his cum in my ass or in my throat, my head on his furry and comforting chest.

He asked me to marry him the night of my 28th birthday. I said yes.

On top of that, Griffin was a realtor and we had just purchased a great apartment in San Francisco together.

How stupid could I have been to mess this all up and end up in California State’s prison? Long story short: very stupid.

Back in the cold room of the Prison, I removed my shoes and painfully took off my jeans. I did not wear a belt; I knew it would be seized from me as soon as I would enter the building. I was wearing some generic grey boxers and socks. I thought it would be a bad idea to bring my Andrew Christian or ES Collections briefs in prison. Smart, right?

I felt so ridiculous standing there in front of the guard. Wearing socks and boxer briefs is just not a good look.

Falcon sighed heavily.

I finally looked at him, trying to appear more self-assured, not so intimidated. I had ideas on what could happen in prisons to so-called “pussies” Griffin had briefed me on being more assertive so I would not get into troubles or get bullied by the other inmates. Not sure I was cut off for this though.

“Damn. Another stupid one!” The guard complained. “What do you not understand in the phrase “take your clothes off”, inmate?”

All my fears were coming true. Falcon really expected me to get naked before him. Worse than that, he actually was in capacity to MAKE me get naked before him.

I was so nervous.

Although, maybe my stress was not such a bad thing in that very moment, at least, I would not get any unwanted erection in front of another man.

For obvious reasons, I had quickly made up my mind on the fact that I would be better off if no one knew about my sexual preferences in jail. The stories about gay guys in prison were just too chilling. Even Janice, my best friend, advised me to keep a low profile. She was working in a rehabilitation centre and she had heard stories.

It had been so hard to come out of the closet, and there I was, forced to lock myself in it again.

I took off my socks first. The tiles on the floor were cold. I looked at my feet, Griffin enjoyed to lick them sometimes. When he was in a dominant mood, he would make me sniff his. I loved his kinky side.

Without a word, I slid down my boxers. It won’t be the first nor the last time I would undress in front of another man.

The guard was smiling, what a creep!

Was all of this really part of the procedure or was he abusing his powers? I could not tell. I hid my genitals with my hands but he stared right at my crotch. I could feel I was becoming red.

A few months before, I would have gladly jerked off to this situation in a porn, but now, I was not sure there was anything exciting about this at all.

“Relax boy, we are all men here.” Falcon spoke.

His satisfied smirk was too much. I looked at the floor again.

“Now, turn around.”

“Is this really necessary?” I dared asking.

Bad idea.

Guard Falcon quickly walked up to me.

He was only a few inches away from me when he whispered in my ear, I smelt his bad breath:

“I think it is, inmate. Now, turn around.”

There was a camera in the ceiling. It made me uneasy at first but now, it reassured me, if I was being recorded, the creepy guard was too.

“Put your hands against the wall.”

I had seen the exact same scene in movies a million times, I could not believe it was happening to me in real life.

I obliged. I put my hands against the wall which made me arched my body a little.

I was so exposed, so vulnerable.

Seconds later, I felt the guard’s large hands on me. First on my shoulders, but then on my waist. That’s when I started to feel a tickle in my groin. Shit! Maybe a part of me was finding this situation exciting after all?

The man’s body is really annoying at times. I was not supposed to get turned on. Griffin literally had fucked me just a few hours before as we knew we would not be able to have sex for a long time. Still, my body had to react at the slightest - even unwanted – human touch.

After my waist, the guard went down on my thighs and ass. He was palping me, feeling me. What the hell was he looking for? A knife between my ass cheeks?

I was still facing the wall when I heard someone else coming in the room behind us. I could not see who he was.

“You wanted to see me, Chief?”

“Oh, Foster, you’re here.” Falcon let go of me.

I calmed down.

“I thought it would be good for you to assist me in this inspection. Have you ever done one?”

“Only during trainings, Chief.”

“Well, take these gloves Foster, it’s time you lose your virginity… If you allow me the expression.”

Guard Falcon laughed grossly but the other guy did not say a word. He seemed as nervous as I was. By the way he was speaking, I also got the idea that he was younger than me.

“Come on, take the lead Foster, run the inspection.”

“Of course, Chief.”

The other guard, Foster, addressed me for the first time:

“Inmate, turn towards me.”

Finally, I got to see the newcomer’s face… and body.

That man was young indeed, certainly in his early twenties, fresh out of school. He had beautiful blue eyes, dark hair, a sharp jawline. His face looked very innocent though, not what you are expecting from a prison guard. The uniform did not fit him. It was a bit too tight; I could see that Foster was very athletic.

Big biceps. Nice pecs. Were they his nipples that I could see poking through his shirt?

My eyes wandered onto his thighs.

*Damn Tyler, when will you stop having a crush on every guy you meet?!*

I know you are waiting for some steamy moments, but that was definitely not the right time, nor place, for eye candy. Should I remind you that I was still stark naked at that point?  I focused myself to remain calm… and flaccid.

“Inmate, you are required to go through an inspection before we let you enter the facilities and assign you to your cell with the other inmates. I will inspect your body for any potential injury and I will check that you are not transporting any drugs or any other illicit item inside the premises. Is this clear?”

Foster was reciting his speech; he must have learnt it in “trainings”. I thought it was almost cute. It was also a much better way to handle this than Guard Falcon’s rudeness.

However, his superior did not seem too happy. He was looking severely at his younger colleague. Probably he was thinking that he was too soft with me.

“It is clear, Sir.” I spoke.

The young hunky guard actually smiled, a real smile, showing all of his white teeth. What a waste having in there, that man should have been an actor in Hollywood, the studios were right next door to the prison.

“Don’t smile like an idiot, he’s not your friend!”

Falcon was not one to encourage friendly, or even courteous, exchanges between guards and inmates. Foster changed his face instantly; he shut himself off and took a light out of his belt.

He cleared his throat:

“Open your mouth, inmate.”

I did although I wished he would have asked me this question in other circumstances. He pointed his light right on my face, it blinded me for a second, then he aimed at my mouth.

“Stuck out your tongue.”

Again, I obliged. What choice did I have?

He took his damn time inspecting my throat. Maybe he was making sure I would not gag when he would fuck my mouth. Wishful thinking, but eh, sarcasm had always been my coping mechanism.

He then checked my body.

“Move away those hands, inmate!” That was Guard Falcon talking, or rather barking.

Reluctantly, I exposed my dick and balls. Griffin had helped me trimmed the day before. I already missed him but it was a bad idea thinking about him at that moment, our trimming session had ended in a hot fucking session under the shower. Again, not the time to get aroused!

“Your hands behind your head, inmate.” Foster commanded.

His tone was a bit firmer now.

He aimed his light towards my armpits, my chest, and then my dick and balls. He put latex gloves on. This shit was getting real.

Again, I could not believe I had found myself in this situation. Was it entirely my fault though? I should have found a better lawyer, that was for sure.

As I was formally (and to my genuine surprise!) arrested for embezzlement, fraud, and drug trafficking, I was authorized to call someone. I had no idea who to call and I reached out to my older brother.

The past few years, we had barely seen each other, but Ryan dropped everything and came to help me out, travelling the entire country in one afternoon. He had a lawyer on his side when he arrived at the police station, a friend of a friend.

Ryan was now a surgeon in one of the most reputable hospitals of the East coast. At 34, he was still gorgeous with a hint of daddy that suited him perfectly. He had two boys with Mallory, twins, they were 6 years old at the time of my arrest. He was now wearing black glasses who made him even more attractive in my opinion. He was also fitter than ever.

I know, I should stop drooling over my older brother.

“How the hell did you find yourself in this mess? Drug trafficking? What the actual fuck, Tyler? And this other guy they are talking about, he was one of your patients? You’re going to lose your medical licence! You realized that, right?”

I looked at my shoes. Of course, I realized that!

“I know Ryan… I messed up… As always…”

“Fuck Ty, I thought you got engaged! I thought you had bought an apartment! I thought you had your shit together!”

“I had! I have my shit together! Griffin is amazing… Oh my god, I’m gonna lose him too now. This bullshit happened two years ago… I was stupid… I did one mistake! I thought it was way behind me now! When the cops called me, I had no idea I was actually in troubles.”

Seeing how freaked out I was, Ryan softened up and hugged me. It had been years since we touched. I loved him. His arms were my safe place.

“Tyler, what are we gonna do with you?” He said with a grin, nodding his head.

I sobbed silently in his chest. I was a child again.

“Please don’t say anything to mom and dad, they are already worrying enough as it is.”

“Listen, we’ll find a way out. I have found a lawyer. (Not a good one! But neither Ryan or I knew that at the time). You’ll check things with him. He does not think the cops have a lot of evidence of your involvement (they had!) and clearly you are not a mastermind or dangerous criminal, so this should be fine…”

“Clearly not, I’m just a stupid moron! I had a thing for this guy, we started dating and I realized too late it was not the best idea...”

“Maybe you could have realized things were not normal when he started to use your bank account to launder money? Or maybe you could just not have sex with your patient?”

“Touché.” I spoke.

He smiled at me.

“This looks like a big mess now, but I’m sure it’s not that bad, Ty.”

“Ryan, I’m so glad you’re here. Thank you.” I just said, sincerely.

“You should talk to your fiancé. This whole thing happened before you even met him, right? I’m sure he’ll understand. Anyway, you cannot keep this from him.”

I talked to Griffin. I saw the disappointment in his eyes. But he did not call off the wedding. He stayed by my side, until the hearing and the judgement. Then, he promised he would wait for me. Only 10 months and we would be together again.

I held on to that thought as I was going through the humiliating inspection. I did not want to be in this room, scrutinized by two prison guards, but I had to bear the responsibility of my actions.

Without realizing it, I was once again facing the wall, naked.

“Bend over, inmate.”

An alarm went off in my head. Was Foster serious?

He was. And bending over was not the worst of it. The orders kept on coming.

“Spread your ass cheeks, inmate.”

I exposed my asshole.

“Cough. Again, cough.”

I had never felt this uncomfortable in my life, but at least, Guard Fallon was not directly conducting the inspection. Not yet.

“Now spread your ass and squat. Yes, go down. And cough.”

Jesus Christ! Clearly, I had nothing in my ass! What did they want from me?

“He should spread wider; you can’t see or access anything like that, Foster! You do need to make sure that the man is not smuggling any drug in this prison.”

“Yes, chief, but I did not see anything, it looks clear.”

“Looking clear is not enough! Can you assure me with absolute certainty that the thug did not hide anything deep in his asshole? You should know, those cons are like animals! They are willing to do the most sickening things. Can you take this responsibility? Because this is what we are talking about here, you will be fully liable if anything were to go wrong with that one.”

“I will double check, Sir. Inmate, spread your ass one more time.” Foster warned me. “Now, I am going to insert one finger in.”

Foolishly, I got afraid that he would find some dried sperm up in my ass. Last time we fucked, Griffin had cummed in my mouth (his favourite spot), but maybe there were some old residues. I did not have time much time to ponder about that. Suddenly, I felt his finger coming in. Wow! This was really happening!

I had been fucked by way bigger things than this finger (including various cocks and dildos) but due to the stress maybe, my ass felt incredibly tight. I could feel that Foster had put some lube on the glove. He was gentle but was digging deep, in search of any hidden drugs in my anus. That thought almost made me laugh. Or maybe I wanted to cry.

Were they really thinking that a professional therapist (who did lose his license, ok) sentenced to 16 months in prison with the possibility of getting out after 10 months would take the risk of bringing drugs into this prison? Or were they just playing with me?

Maybe I should file a complaint. To whom?

To be fair and although I did not want to admit it, a part of me, somewhere, was also enjoying this. A handsome young man, probably straight, fingering me. Back in college, I would have prayed for this to happen every day.

“You’re doing it wrong, Foster! I know this is disgusting but this is part of the job.”

At that point, Falcon really started to get mad, and I really started to get worried.

I was right to be.

The young guard moved away and the bald one took matters in his own hands. Quite literally. Without putting any gloves on, he shoved one and then two fingers up my ass. I screamed. I was shocked. It hurt!

What the fuck?

“Chief!” Foster objected, but the sadistic guard was not listening to him.

There I was, still bent over, in my birthday’s suit, being fingered by this guard and I just could not say anything to stop him. He was actually fucking my ass with his fingers at this point.

After a few back and forth, Falcon finally released me and announced formally:

“Now, I can state that this one is cleared. See how it’s done, Foster?”

I was so stunned. I was sweating a lot too.

I hated the fact that I did not react. Years after college, I was still the same awkward and scared Tyler, not able to stand for himself. But what could I have done?

“Now put some clothes on, inmate.” The guard barked at me, pretending to be grossed out by my naked body. As if!

He handed me tiny white briefs, white socks, a white greyish tank top and a blue inmate uniform. I thought orange was the mandatory colour for new inmates. Maybe I was watching too much TV. There was a number on the uniform, 328.

Foster was no longer looking at me. He seemed very uneasy now. Maybe he would help me out if I were to lodge a complaint?

Before coming in, I was worried of the inmates, especially of what they could do to me if they found out that I was gay, but I did not think of the guards. Maybe I was them that I should have feared. I thought again of the camera in the ceiling. What would happen if there were none? What would Falcon have done to me?

I quickly got dressed, too happy to finally put some clothes on. There were neither comfortable nor fancy, but at least, I could hide my genitals!

“You can go, Foster, tell Inmate Dantons to come here, he will take care of our new Inmate 328. He’ll show him the ropes”

“Will do, Sir.”

With that, the young guard hastily left the room. He had not given me a single look since Falcon had fingered me. He was probably too ashamed of the behaviour of his colleague and superior.

Guard Falcon had a vicious smile on his face.

“You kinda liked it, right?” He asked me.

“What are you talking about?”

“I’m never wrong about these kinds of things.”

He brought two fingers to his mouth, the ones he had just put in my anus. Before my incredulous eyes, he started to sniff, and then lick and suck them.

“You did not like those?” He asked again, kissing his wet fingers. “You’re sure?”

I was panicking. There was no doubt at this point, this was not standard procedure at all. I was getting abused. I needed to find a way out.

I did nothing. Several seconds passed.

“Now, I can be generous with obedient Inmates. I want to show that to you.” Falcon said, keeping a devilish smile on his face.

Stupid bald man, I thought. But I remained silent.

He looked for something in his right pocket. I glanced at it. I realized that he was hard under his pants. A huge bulge was undoubtfully visible. He got a few coins out of his pocket, I was not expecting that.

“Here you go Inmate Braxton, for your obedience. Before we take you in, you get to make one last phone call.”

I did not want to take his money or this phone call. I knew that it would only mean I would owe this asshole. But Falcon did not leave me any choice, he forcefully grabbed my right arm and put the coins in my hand.

“I’m not usually that generous, don’t waste it.”

He held my hand tight. He was so close to me. Again, I felt his bad breath on my neck.

We got out of the room and I was shown a few phone booths right near the facility entrance, in a space usually occupied by visitors. Everything was so old school, it felt like we had gone 30 years in the past.

Falcon was looking at me from afar.

After a few minutes of hesitation, I did use the coins. I did make the phone-call. I was fighting back my tears.

To this day, I still have no idea why I chose to call him of all people. I had memorized his phone number years ago but we had not really talked in years.

I did not want to break down hearing from Ryan or Griffin. I certainly did not want to call my parents. I could have called Janice.

But I called him.

“Hello?... Hi?... Who’s this? I’ve just had a message this was coming from the Correctional Centre of Southern California, is this a joke?”

“Hi Austin… It’s not a joke… It’s me… Tyler.”