My First Year in Prison Ch. 17

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A bachelor's party in prison: things are bound to get wild!
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Part 17 of the 24 part series

Updated 06/11/2023
Created 05/02/2022
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Tyler is happily engaged when his life takes a turn. After a couple bad decisions, 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? (Erotic Drama - sequel to My First Year in College).

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My First Year in Prison

Chapter 17: To love and to cherish you...

With age, I have learned to always listen to my guts. I have found that those were always right.

The day of Xander's wedding, my morning literally started with multiple pukes in our shared toilets. That should have been a clear sign.

For the first time in months, we had been authorized to drink the night before and we were all feeling like shit. I thought this was the reason I had this strong feeling that I would be better off, just staying in bed all day. I did not want to get up or do anything.

Something was wrong. I felt it. I knew it.

But this was Xander's big day and I ignored my guts.

Would things have turned out differently if I had stayed in bed? Maybe they would have, maybe not.

Writing these couple of chapters will probably be the hardest thing I will ever have to write. Going back into the worst day of my life, to the fear, the pain, the trauma. But as I thought it was important to retell the day when I came out in college (in the worst possible circumstances) and got hit by a freaking car, I have to tell this story too.

Both events shaped me into who I am today.

It had all started so well. It was even strange how the previous night had gone almost perfectly!

Xander was unanimously liked in the prison and the guards had accepted to let Ralph and I organize a big bachelor's party in the cafeteria.

Of course, this was nothing fancy, but we all had been authorized to drink a couple of beers each and, in order to appease the tension between the groups (not to say, the "gangs"), everyone had been treated the same way. Friends of Xander or not, all convicts were invited and could enjoy half of a pizza and a beer.

I was expecting it to be chaos but somehow, it just worked. Well, it was chaos for sure, but the good kind!

Some of the guys did not actively participate, Romano, his bitch Kim, as well as Bianchi, left early, but that was ok, they let the others have their fun. Of course, I learned later that they were busy elsewhere, they were finding new channels to get drugs inside the prison's walls, but I will come back to that.

Tension had been building up for a few months but that evening, it was like everyone needed to have one night off, a truce if you will. We had planned various surprises but I was particularly excited for the act I had been preparing with Ralph for the past few weeks.

It all started when Xander complained that the real downside of getting married in prison would be no stripper at his bachelor's party. Ralph and I made it our mission to change that.

And just like that, unknowingly to Xander, we approached some of the guys to convince them to form a strip band, Magic Mike Style. I may have been a little more excited than Ralph by this prospect but the bodybuilder happily went along. He was way more convincing than me to get our mates to participate.

Seven guys from our little group actually volunteered and we had a lot of fun planning the "show". I just had to ignore the constant homophobic jokes and banters during our secret meetings to plan the surprise. I mean, as long as I had my eye candy and could assist to the training sessions, I was good.

The guards Davis, Falcon and Foster were aware of our plan and were there to make sure things would not get out of hands. But in fact, deeper in the night, Davis and Falcon were the ones encouraging things to get even wilder!

Once we had drunk our beers and everyone had already loosened up a bit, we sat Xander on a chair in the middle of the cafeteria. Roughly a hundred inmates were standing or sitting, forming a huge circle around him.

Guard Davis was our main accomplice and he came with a stereo. We blindfolded Xander with a t-shirt, he was getting kind of nervous. Once he could no longer see a thing, seven guys walked in the middle of the circle, giggling like children: Fernando, Pope, Ray and his son Trevor, Ralph, Big Pepe and Kurtis. The other inmates were applauding and hissing. The guards were laughing too.

My role in all of that? Well, I was supposed to be the host, presenting the "Magic Seven" to the crowd and to Xander.

"Welcome to the biggest show of the year!" I said, trying to sound confident but failing miserably. Most of the guys did not hear me or pay attention, people were shouting and yelling too much. Kurtis who was standing next to me came to my rescue.

"SHUT THE HELL UP, GUYS! SHOW IS ABOUT TO START!"

Someone shouted one last "woo woo", but it worked, the crowd calmed down. Will had stayed within the audience, he winked at me. I cleared my throat.

"As I was saying, welcome to the biggest and most outrageous show of the year!"

They were some more applause but now, the inmates were listening. It was not like we were having tons of entertainment in this hell of a place, so even this silly strip show felt like the freaking Oscar to us. Shit, this was nerve wracking, but so fun at the same time.

I interviewed my blindfolded cellmate, oblivious to much of what was going on:

"Xander, have you not been dreaming about having a Bachelor Party full of nasty strippers?"

"You damn know that I have!" He replied, smiling like a kid on Christmas' morning.

Fernando moved his pelvis back and forth right next to Xander's face and the whole crowd laughed. Of course, Xander had no idea why. Inspired, Pope pretended he was about to give the bachelor a blowjob. I was flustered but kept going.

"Well, you are in luck, Xan! We have found the best strippers of the country! They are called the Magic Seven and believe it or not, they have agreed to come all the way down to the Southern California State Prison to give you their best performance."

Some more hissing and some more laughter. At this point, the guys were flexing next to me, especially Ralph who was even kissing his huge biceps. They were still wearing their undershirt, dirty trousers, trainers and socks but this was about to change. Kurtis was a bit more reserved than the others but he was there, ready to strip down as well.

Just like the others, it was Ralph who convinced Kurtis to join in. At first, I thought that this was a bit out of character for Kurtis to expose himself in that way but I guess he had always been a team player. Thinking of which, he was mostly shy with sharing his feeling, not his anatomy...

"The Magic Seven, what the hell is that?" Xander asked, semi laughing as well.

"Well, I guess it is time for you to find out!" I announced.

I gave Guard Davis the sign and he launched the notorious "you can leave your hat on" track. Everyone understood what that meant. Let the show begin!

The guys had rehearsed some sort of a choreography but they clearly were not on point. They were supposed to do the same hip moves and took off their tops at the same time but it was just a whole mess. Some undressed, some did not, nobody took off the blindfold from Xander and the guys were dancing more like the Village People than Channing Tatum in Magic Mike. Pathetically hot.

I was surprised to see how Ray and Trevor were comfortable with each other, taking their clothes off next to one another, I would never have done such a thing with my dad but they were having the time of their lives.

I guess that pretending to be professional strippers in a prison facility is one way to bond with family!

I was the one to take the blindfolds off from Xander's eyes while the seven guys were now in front of him, bending over to show their asses. That was a part of the choreography they did remember. The strip had only begun, they were all still wearing their pants.

"Fuck, Hell no!" Xander reacted when he realized that he had seven pair of male bums before him. The hissing of the other inmates was louder than ever.

The music was still blasting off in the background and from this point on, the performance really got naughty.

Ralph ripped out his shirt with his hands revealing his large chest, sweaty pecs and abs. Kurtis took off his top as well and threw it on Xander's face. Fernando and Big Pepe were both already shirtless and did a weird move together, rubbing their asses against one another. Trevor and Ray were at the respective left and right end of the line slowly taking off their shirts not realizing they were doing the exact same move.

Like father, like son!

Pope was already in the process of throwing his sneakers in the air, one almost hit Falcon in the face. Xander was semi covering his eyes, semi pretending to throw bills at the strippers. Fernando got closer and put Xander's hands on his hairy belly and then closer to his crotch. The crowd was going wild!

To avoid disturbing the show, I had moved a bit on the side and was no longer centre stage, but I was still front row and enjoying every second of it. Glenn was practically drooling not far away from me.

The song "Pony" had replaced "you can leave your hat on", and the guys were pretending to hump Xander, or each other, in the lewdest positions that you can imagine. I had gone to my fair share of gay clubs in L.A. and then San Francisco, but nothing can top the sexual energy of straight horny inmates in a constant state of blue balls.

Pope and Fernando were already in boxer briefs (the bulge sported by Pope was INSANE), but too much stuff was going on at the same time and I had trouble to follow.

My eyes were going back and forth between the guys but they did stay a little while longer on Kurtis who was pretending to fuck the floor, grinding like a professional stripper. Of course, he was the best at it.

Damn, I wish I was the floor right at this moment. Fucking grind on me, Kurtis Jensen!

I really did miss my shot with that guy. Sensuality was pretty much exulting out of him 24/7 but that was when he was not even trying! When he did put on a show, it was just extraordinary. The way Kurtis was moving his pelvis, his hips, flexing his biceps and his perfectly shaped body, taking off his clothes... I was hard of course, but I could even feel my ass twitching, as if my hole was recognizing its rightful owner.

Will looked jealous, he could be!

My eyes went back to Xander for a few seconds, Ray was giving him a very lewd lap dance while Trevor was taking Xander's shirt off.

"Guys!!" Xander was yelling while laughing hysterically,

Was it a feverish dream or was it really happening? I thought it was a good thing I was not in Xander's place, I would never have been able to contain my excitement and would have probably wet my pants, stuck in the middle of a sandwich between father and son.

It was at this point that all the pants started to get thrown in the air and Ralph smacked his huge muscular ass (still covered by his boxer though) against Xander's face.

I think I need to point out once again that although we did not have much to drink, for most of the inmates, it was the first sip of alcohol they had in months or even in years, this was bound to get wild! And it definitely did.

It was Big Pepe's idea to lay Xander's on the floor while they were all taking turns grinning on him. Pope took off Xander's pants for good measures, from this point, they were all only wearing their white underwear and then... the "contest" begins.

Also pumped by the moment, I asked the crowd to vote for their favourite stripper. They would be judged by the intensity of the applause. But at that moment, the music abruptly stopped. It was Falcon. Damn, was the show over? Did we go too far?

On the contrary!

"And the best stripper of the night will win...." Falcon got some more beers of the cooler. "Extra beers! Good luck!"

He pressed play again on the music and the inmates were literally going crazy. What the fuck? It was a beer, not 1 million dollars!

Daddy Ray went first, humping against Xander's body, putting the bachelor hands on his ass, he slid down his underwear to reveal his big fat butt. His son went second but did not top his father. He was hot as fuck, a handsome 18 years old guy with six packs abs, a perfect bubble butt and great shoulders but compared to some of the others, he was just too tame to make an impact.

Fernando, Pope and Big Pepe all gave a good show but Kurtis who went after them was clearly better at this. Although I was not sure he was winning in terms of applause, he was clearly my personal favourite. When he slowly slid down his hands in his own underwear, going through his treasure trail and ultimately grabbing his cock in front of the whole crowd, I thought I was going to die.

He then took off his boxer briefs in a classic stripper move, not letting his dick show. He was hiding his junks with his hands - barely, his limp dick was very large.

No surprise, Fernando had already gone full monty and did get the biggest applause for this, but Kurtis' nakedness was something to cherish and worship. His ass looked simply delicious.

Ralph was the last one of the "Magic Seven" to give it a try, grinding on his best friend, pretending to be sitting on his face and finally, removing his briefs in front of the entire crowd. But there was no need for modesty there! Ralph did not hide a single thing and his huge cock was flapping around. He went back on Xander, did the helicopter with his giant cock, and even... stroked his dick, getting a semi-hard-on!

That guy was a fucking pro at this. Although it looked more like a porn than a strip show, he was clearly winning the game at this point. I took a glance at the guards; this was certainly going too far at this point? But no, they were hissing even louder than the inmates!

"There is no reason we should not be eligible to compete and win that beer!" A huge black guy shouted. He was one of the best friends of Pope who was sometimes spending time with us at the gym.

I had not realized he was talking at me at first, as if I was actually the referee of this whole thing. In my capacity of host, I replied:

"I... yeah... go... go ahead! Take your chance."

The least I can say is that the strip show from that guy was straight to the point. He walked to the middle of the room and simply slid down his pants to his ankles to show off his big black cock for the whole crowd to see, holding it with his two hands.

"How much applause does this big piece of meat get?" He yelled to the crowd.

I thought it could not get crazier than this but from this point on, dozens of guys came in the centre of the circle to strip down, most of them completely, in an absurd attempt to get a couple more beers but ultimately, to feel some kind of freedom, bending the rules and throwing their clothes in the air.

Xander was no longer the centre of attention, the whole thing had become a mad circus where everyone was stripping for everyone else, trying to always act more provocatively.

I felt someone pushing me, I turned around and Will was there, taking off his shirt, joining the others in the strip show.

"Great night you have organized for us, babe." He whispered while opening the fly of his pants.

"Will..."

He did not let me finish and threw his pants in the air. He then grabbed my crotch.

"Damn, you're hard."

We were literally in the middle of everyone, what the hell was he doing?

"Will, stop! Not here!"

"Come on, I can feel you like it, nobody is paying attention to us." He grabbed my right hand and guide it towards his boxer briefs. "Feel mine."

It took all of my willpower to remove my hand from this warm, musky and sweaty heaven that was Will's boxer briefs. I felt his dick semi hard; I groped his balls but then, I stopped myself.

"No." I said.

No. It was not a word I was using often. That felt weird. Will was about to whisper something again when the music stopped. Everyone turned around to watch Falcon who had taken back control over the evening and was standing up on a table to give his instructions. The bald guard was having the time of his life.

"That's the hell of a faggy night we got going on here!" He stated.

I looked around, half of the inmates were barely or totally naked. Some were still pretending to hump each other. A few of them were hard, either under their pants or explicitly jacking off. I had not realized things had escalated so quickly. I was ready for Falcon to scold us.

In a million years, I could not have guessed what Falcon was about to say next.

"Foster, your turn to show what us guards can do!"

My heart literally skipped a beat as Foster looked astonished.

Davis added:

"Everybody should get his chance at winning those beers. Inmates or guards. Foster is going to represent us in this battle!"

If I thought the crowd had been loud before, it was nothing compared to what was happening at this point. It felt like an explosion. Inmates applauded, banged chairs against the floor, shouted at the top of their lungs.

I initially thought everyone had gone furious and things were about to degenerate but not at all, they were just happy as I was at the prospect of a guard actually stripping down for us!

"That's just classic!" Ralph exclaimed. My cellmate was still wandering the cafeteria naked and hard.

"Guys..." Foster tried.

He clearly wanted to back down at first, that was not his idea. But Falcon had put him in a corner, he had no choice, more than a hundred inmates were now shouting his name:

"FOSTER, FOSTER, FOSTER."

"Calm down, guys." Davis spoke with a light smile. "And move over, let's Foster concentrate and take on the stage."

He pressed play on his stereo, and the song Lollipop from Lil Wayne came on. I could not believe this was actually about to happen.

The atmosphere was the one of an actual bachelor party or of a last night at a college summer camp, there were no guards nor inmates, just guys having fun.

Foster ended up sighing and smiling at the same time and did walk right in the centre of the circle. "If I do that, I'll do it right!"

Lil Wayne was rapping about sucking a lollipop. Foster found back Xander in the crowd and put him back in the chair. Xander was now only wearing a semi torn-up boxer and was sweating a lot.

Foster started by grabbing Xander's hands to make them go over and then under his shirt. Slowly, the guard took off his jacket and then unbuttoned his white shirt, asking Xander for help. The guy who was pretty much hallucinating.

"Woooooooooo" Kurtis shouted standing on the other side of the circle, facing me.

"No homo, Young Moolah baby

I said he's so sweet, make her wanna lick the wrapper

So I let her lick the rapper"

Foster must have done some things like that in his past! Maybe he was a stripper or a gogo- dancer to pay for police school? He could not be so natural at this! The guy was dancing and taking off his clothes like a pro. Only a few people laughed, we were much like hypnotised by his sudden confidence.

Foster took off his shirt completely and started to twerk his ass. There was no question anymore, he would win the contest of most applause. A deserved prize, that little bum looked yummy as fuck squeezed in his tight uniform pants.

Again, he used Xander to help him taking off his belt and his pants. Foster was enjoying this for sure. This is always so exciting when you discovered a side of someone you had never imagined before.

"Shawty want a thug

Bottles in the club

Shawty wanna hump"

When Foster started grinding on Xander in his blue navy boxer briefs, it was clear that Kurtis had a serious competitor for hottest guy in the facility. I looked at him on the other side of the room and smiled, Kurtis smiled back and walked towards me through the crowd.

12