In Prison with My Idol

CS, I hope the way I wrote your story follows the spirit of what happened.

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When I was 5 years old, my biological father realized having a family was not for him. He disappeared without leaving a phone number or address. All that was left of his existence were a few pictures, debts, and... me. Mom struggled to raise a child while working full-time at the local Walmart. Our financial difficulties continued until I became a junior in high school and found students who needed tutoring. The supplemental money was helpful.

In high school, I was a B-average student. Nothing interested me until our teacher started telling us about famous criminals: John Dillinger, Clyde, and the Mafia bosses. I was fascinated by their ability to achieve their goals through crime for years. After learning about these personalities, I went to the library and read their biographies.

Our neighborhood was not a nice one. Drug dealers, prostitutes, and other low-life people roamed the streets, and the police were helpless to make a dent in their illegal activities.

The most notorious guy was Tony 'The Bucher' Bianchi. Everybody knew he was the boss, and nothing was done without his approval. The law tried to catch him multiple times, but it was futile. He was the envy of many kids like me. He had a shiny, bulletproof black Mercedes and used to stop by when we played basketball. He would get out, joke, and give us candies or dollar bills.

When I turned 17, I saved a little money and bought a used Toyota Corolla. I loved driving. At the same time, I read everything about cars and made up my mind that I wanted my future to be around cars - Either as a mechanic or a driver.

By 18, I was already a good driver and acquired some knowledge about fixing mechanical problems. I liked to show off my driving skills before my friends. Most were taller and stronger than me, but nobody was a better driver.

One day, as I was displaying my abilities controlling my car, Tony stopped by. At first, I didn't see him and was talking proudly as if I was Lewis Hamilton. Tony listened to me quietly and then approached me, put his hand on my shoulder, pulled me to the side, and said, "You are Larry, aren't you?"

I mumbled, "Yes, sir."

"My car driver is in the hospital with a severe lung infection. According to the doctors, he'll have to stay there for weeks, if not months. I need a driver. Would you be interested?"

I gazed at him admiringly, "Yes, of course, sir. I'll be honored."

He chuckled, "Can you keep a secret? I mean, you should NEVER mention anything we do to anybody, including friends or family."

"I promise!"

He stared at me and said, "Remember your promise, boy. I am sure you've heard about my reputation. Anybody who ever crossed me regretted it, if he was still alive..."

"Sir, on the life of my mother..."

He cut me off, "That's good enough for me. Tomorrow at 10 am, come to Joey's Cafe, and I'll introduce you to my buddies."

...

On time, I approached Joey's front door and was stopped by 2 massive guys, "Where do you think you are going?"

"My name is Larry. Tony asked to talk to me."

They looked at me with mocking eyes. I didn't blame them. At 5'7" and 155 pounds, I was hardly the guy Tony dealt with. One of the guards went inside and chatted with Tony. He returned, checked that I carried no weapon, and let me inside. Tony introduced me to 3 big guys who sat at his table and mentioned I'd be their new driver. One of them laughed, "Do we have to trust this tiny cucumber with our lives?"

Tony grinned, "Enzo, it's a fair question. Tomorrow morning, bring your car and I'll give him mine. You two are going to drive 3 miles through the city streets, reaching where I'll be. If you win, Larry is out. However, if he wins, you'll shut the fuck up. Deal?"

Enzo smiled, "Yes, boss."

To cut the story short, I arrived a minute and 22 seconds before Enzo.

I became their driver. Unbeknownst to me, the first mission was a test. They told me they were planning to rob a Jewelry store the following day at 7 pm. I arrived on time and drove expertly. Tony was happy. He handed me $200 and told me it was a mission to test my loyalty and ability. Since I passed it with flying colors, I became the official driver.

...

Growing up, I noticed early I was different from the other guys my age. I was never interested in any sports. I loved to read and watch TV. Later, when my classmates began whispering about girls, I was not interested. At 18, my friends, and later the gang members, loved to talk about the ladies they were fond of or had sex with. I attempted to fake interest, but the truth was that a relationship with a girl was never on my mind. Seeing tits or women's butts and muffs simply did not do it for me. Deep down, I suspected I was gay because when I masturbated, my muse was a headless, unidentified, muscular body. However, I did not do anything about it.

Since I did not join the group during their raids, the only information I got was when and where to wait for them, and then drive fast, avoid the police, and reach the gathering spot. I did it for almost a year, and Tony compensated me handsomely. I brought the money home to Mom and told her I was working as a mechanic in a car shop. She was happy I was doing well and never bothered asking questions.

It all fell down one evening when the gang decided to rob the biggest pawn shop in the area. I was not privy to the details. I only heard talk about a pawn shop and that the owner offended Tony. I drove them and waited in a small street nearby. Ten minutes later, I saw Tony running in my direction. As he opened the car door, 4 police cars surrounded us. Later, I heard 2 other members were captured while Enzo ran in the opposite direction and was more successful escaping.

At the police station, I called Mom and told her that I had driven a passenger who got into trouble and I'd be away for a while. She began crying. I reassured her everything would be OK.

In short, it wasn't OK. Tony got 10 years in prison, and the other 2 accomplices got 3 and 5 years, respectively. My trial was 2 months later. I thought I'd get out on probation, but the judge decided to lock me up for a year. Mom was devastated. I said that with good behavior, I'd be out in 8 months.

...

My first day in prison proved to be tough. One of the guards mocked me, and a prisoner threatened me that if I didn't give him my burrito, he'd stab me the following day. I was hungry and refused. The next day, when we were free to roam on the court, I saw the guy coming in my direction. I ran away, but he chased me. I fell to the ground, knowing I was doomed. Suddenly, I saw a strong hand grabbing his neck and pulling him away. It was Tony. I didn't know he was here... He held the guy and smiled at him, "Johnny, this new guy is with me. If you have issues with him, come to me. Capisce?"

"Yes, Tony, but he refused to give me his food."

"Johnny, you didn't clean your ears for too long. Larry is my buddy. He owes you nothing. Leave him alone, or you won't be able to eat YOUR food tomorrow."

"OK, sir, but it's not fair."

Tony ignored him. He hugged my shoulder and whispered he'd talk to the head honcho to place me with him in the same cell. Indeed, the next day, I was moved to be with Tony. I was super excited: I'd be with the guy I admired more than anybody!

I took the opportunity he was out to talk to the warden, cleaned the cell with my bare hands, and arranged his bottom bed better. He arrived back 20 minutes later, saw the result, and smiled, "We'll be good mates."

Whenever we were allowed to go in the yard, he usually conferred and played with other prisoners. I was mostly alone, sitting down or exercising mildly. The good news: Everybody knew I was under Tony's protection, and nobody dared approach me.

One evening, Tony invited me to sit with him on his bed. He said he missed his girlfriend. He showed me a picture of her in a bikini. She was a blonde beauty with a seductive smile, big tits, and long legs. He sighed, "Imagine that rather than you, she was here with me. She is a hungry bitch and loves our sex. When she is around, her only request is to be fucked nonstop. Whenever I am not in the mood, she sucks me to a happy ending. I have been here for 4 months already and miss her, especially her sweet mouth."

A crazy idea crossed my mind, but I could not verbalize it, so I inquired, "What do other prisoners do about it? I mean, some of them have been here for years."

"Many prisoners masturbate, mostly during the night. The groups' leaders usually find 'bitches' among the wimpiest prisoners."

"You didn't try to force me into sexual things. Does it mean you feel sorry for me, or I am not attractive?"

He grinned, "You were my most loyal employee, and despite my bad reputation, I hurt only those who betrayed me or stood in my way."

I whispered, "Tony, I like you."

He laughed, "Don't be a softie on me now."

I hugged him, "I mean it. Before you asked me to join your group, I admired you from a distance. When you called me, I was the happiest man ever. I want you to be happy."

"What are you saying?"

I didn't answer. My hand descended to his groin and began a gentle caressing of his covered member. He gasped, "Larry, don't tempt me!"

I glanced at his face and pleaded, "Let me help you..."

He stayed silent. My fingers fumbled with his fly and slowly opened it. I noticed his penis started growing while I unbuttoned his pants. He sighed and leaned on his back. His underwear showed a large tent. My breathing shot up - His organ was much bigger than I thought. I knew his tool would be bigger than my 5" when erect, but his was already about 7" and not at full mast yet!

I lowered his boxers and, for the first time in my life, ogled another man's cock. It was long, thick, dark-colored, veiny, and with a large mushroomed head. It was an awesome monster. I wished to feel it in my hands... and mouth, but I doubted I could handle such a huge pecker. I began bobbing the shaft with both hands, enjoying the velvety feeling. It stiffened rapidly. He lifted his head and stared at me, "Do it!"

I licked the tip and then kissed it. The last time he showered was hours earlier, so it smelled musky, and the taste was a mixture of sweat, musk, and... manhood. I found it extremely arousing, and I felt my dick begin to harden as well. I opened my lips as wide as I could in an attempt to envelop the giant head. Its softness allowed me to engulf the head. I milked it lightly, and a drop of precum landed on my tongue. The taste was very mild.

Next, I decided to pull it into my oral cavity just like I imagined a blow job was supposed to happen. It wasn't as easy as I hoped it would be. Tony's humongous girth made me gag after only 2 inches. I pulled it out and coughed. I tried again. This time, about 4" entered before I started choking. My mouth was full of leaking saliva, and my eyes teared. However, I was determined to repay my debt to Tony. I tried a third time. As 5" invaded my mouth, I felt Tony's hands grabbing the back of my head, and he began fucking my face.

His initial movements were gentle, as his cock gradually dilated inside my mouth. It felt good. Then, suddenly, his body tensed, and he pounded my oral cavity powerfully. I couldn't breathe and tried to retreat, but he was much stronger, and I could not move. Seconds later, jet after jet threatened to drown me. Fortunately, the flood stopped before I fainted. I lowered my head, and a mix of Tony's cum with my saliva spilled on the floor. Tony chuckled, "Larry boy, that's what happens when you play with fire."

I forced a smile, "I was about to lose consciousness, but I am happy YOU feel better."

He grinned, "That's the spirit. I bet you've never given head before. Right?"

"Yes..."

"Well, at least now you know how it feels. According to my girlfriends, the more experienced you are, the easier and more pleasurable it becomes."

I stayed mum and climbed to my upper bunk bed. I didn't feel like talking. I was embarrassed by my less-than-optimal performance and... the fact I was having an erection... I fell asleep half an hour later.

The following morning, I woke up early and needed to pee. After emptying my bladder, I returned to bed and saw Tony asleep, lying on his back with the blanket on his side. He was sporting a giant woodie.

My lips got dry, and I licked them. After doing it, I realized I was tempted to suck Tony again... I didn't want to wake him up. He started moving 15 minutes later. I thought to talk to him, but the morning wake-up alarm sounded and there was no time.

We were alone in our cell after dinner. Tony was in a good mood after receiving a letter from his girlfriend. I saw him laugh and asked why. He grinned and showed me: In addition to the letter, in which she vowed to love him forever, she sent him a picture of her exposed boobs with the writing 'Miss you.' We examined the picture for 30 seconds, and I noticed Tony's prick begin to stretch his pants. I gazed at his face. He looked at me hungrily. I didn't hesitate. I came closer, opened his fly, and took the spongy head into my mouth.

I inserted 2" and began bobbing, each time taking more of him inside. I wasn't sure how much of him was in when Tony warned me his orgasm was pending. I pulled out slightly and sucked hard on his soft head. Once he tensed, I placed my tongue in front of his slit and continued milking him. His seed hit my tongue 6 times before dying down. My mouth was full of his slimy juice, but I did not gag or choke. I was even able to appreciate the taste. It was oily and somewhat salty. Not bad, really... I stared at Tony's face, smiled, and swallowed the thick liquid.

He caressed my head, "Boy, you are becoming a real asset. How was it?"

"You were right. Now that I know what to expect, I can time your climax and prepare accordingly. This time, I was in control and actually enjoyed it..."

"Sounds good to me. I have no idea if you tried to be nice to me or you are a faggot."

"I was never attracted sexually to girls. I like the way you treat me, and I find your physique alluring."

"Larry boy, I think you are gay, but the future will tell."

"Tony, I saw your woodie this morning. I don't know how often it happens, but if you want me to relieve your sexual needs, tell me."

He chortled, "It depends on how often I remember the escapades my girlfriend and I had and crave fucking her again. It happens up to 3 times a day."

"Logistically, I doubt it's possible to do it more than once a day, but I'll be happy to give you head whenever you wish."

"Larry, I think you are gay."

"You may be right. Does it matter to you?"

"Knowing I am not forcing you to suck me and you like it makes me feel better. But if you are really gay, you might enjoy back activity too."

I whispered, "I thought about it, but you are huge and will rip my ass..."

"Boy, consider it, and if you are ready to try it, let me know. In the meantime, an oral job is still an enjoyable experience."

...

I was in a bind. I knew Tony would love to use my ass, but I was terrified my anus won't be able to take his massive tool. After 2 days of struggling mentally with the subject, I told Tony I had an idea: With his unique connections in prison, he could get almost anything he wanted. I asked him to bring me different sizes of carrots and cucumbers, with the largest one's circumference like Tony's pecker when completely hard.

Tony grinned, "boy, you are smart! You plan to use these as anal training tools, aren't you?"

I blushed and smiled embarrassingly, "Yes, sir."

He embraced me, "I wish everybody was like you: Uncomplicated, trustworthy, and think constructively. Both on the street and here, I need to show others how mean I can be so they are afraid and abide by my rules. You are weak, yet you do everything for me, not because of fear."

I murmured, "That's because I admire and like you."

"Good answer. Do you know you are the only one around here I feel safe turning my back to? You never know who may jump on you from behind and stab you in the back."

The next day, Tony brought me 2 cucumbers of different diameters and a carrot with a pointy tip but almost as thick as my arm at its base. He smiled and pulled a tiny bottle with oily stuff, "It's not KY Jelly, but it may help if you know what I mean."

In the following 3 days, I used the smaller cucumber 3 times a day. On the 4th day, I started inserting the thicker cucumber. In the beginning, it hurt a lot. I continued and learned to relax my sphincter around the large girth. After a week, the pain of passing through my anal ring disappeared. Moving the thing in and out felt pleasurable, and when I pushed it deeper, even arousing. Next, I penetrated with the carrot. The surface wasn't as smooth as the cucumbers, so I rubbed the sides against the wall until it was 'polished.' When it looked better, I began using it. It felt more enjoyable than the cucumbers from my first try, likely because it reached my prostate and pressed against it. On the third try, it made me horny, and I jacked off with the carrot deep in my bowels.

I was ready for Tony on day 11 after our talk.

That evening, when Tony returned to our cell, I approached him, grabbed his prick, and whispered, "Tony, if you want to use my ass, I think I am ready, but start slowly, please."

His eyes brightened, "Be on all 4 on my mattress and spread your legs." I checked, and no guard was around. I lowered my pants and briefs, covered myself with the blanket, and positioned myself on my elbows and knees.

Tony came behind me. All of a sudden, my courage left me. I buried my face in the pillow and prayed to survive the act. Tony began by inserting his forefinger, followed by adding the middle finger. I felt the stretching but no pain. He removed the fingers, smeared the oily stuff on my crack and his cock, and gently pushed the spongy head into my butthole. My sphincter widened under the pressure, and at one point, I felt it was the maximum I could absorb and whispered, "Tony, I can't..." As I was saying it, I heard a plop sound, and the head was inside. It hurt a little, but it was tolerable. I held my breath and waited. Tony was patient as well and didn't move. He added oil and advanced slightly further. It was an additional stretch, but then his shaft invaded my rectum. Tony stopped again, letting my anus adjust to his girth before tenderly progressing uninterruptedly. My butt felt wide open with a huge foreign object stuck at the door. It hurt a little, but his well-lubed movements made it easier and, soon, even pleasant. Tony started bobbing my ass slightly faster, shoving my prostate in the process. Within less than a minute, my penis jolted and hardened like never before. The constant nudging of my prostate made me very horny, and I began countering his actions.

I closed my eyes and felt great. I was ready to ejaculate and blurted, "Tony, I love what you do. Do it faster, please."

I heard him giggle as he intensified his pounding of my behind. I erupted with gallons of whitish goo on his sheet while howling like a wounded coyote. Tony continued impaling my hole for another 10 minutes before growling and pouring his hot lava into my bowels.

When he pulled out, I was exhausted and fell on the mattress. I recovered about 15 minutes later and emptied my colon in the toilet. Sitting on the toilet, it occurred to me I liked the way Tony used me: I liked both sucking him and being fucked by him... If there was one thing missing, I would have liked to be hugged and feel loved afterward.

...

It became our routine: Ten minutes before the morning alarm, I'd suck him to a happy ending, and later in the evening, at least 3 times a week, Tony used me anally. Initially, I was somewhat embarrassed to admit to myself I was enjoying being rammed in the ass, but within 2 weeks, I realized I was right in the first place: I WAS GAY! There was nothing wrong about being a 'homo,' despite the nicknames I heard frequently when I was in the yard and Tony was not watching.