My First Year in Prison Ch. 24

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 24: Room 403 (EPILOGUE)

I knocked at room 404.

I expected to see Kurtis but Austin was the one to open the door. He was shirtless and visibly drunk. I mean, we were all wasted at this point. The day at the beach, the night at the bar, the shots...

"I thought Kurtis was in this room." I told him, confused.

"He is!" Kurtis replied, showing himself behind Austin.

Kurtis was shirtless too. Fuck, they were really going to make this difficult for me!

"I... I don't understand..."

"Dude, we were about to go to our respective rooms. Waiting for you to make your biiiig decision." Austin stopped talking to refrain a burp. "We did not know if you were picking him or me. We sort of laughed about it, I mean, quite funny the dilemma, is not it? And Kurtis said we could use the minibar while we were waiting for you... We did."

Great, I thought, more alcohol!

"We absolutely did." Kurtis confirmed.

They were both laughing awkwardly while they were talking. I have to admit this whole thing was a bit ridiculous and I even wondered if they had not been fucking with me with their love declarations earlier. Was it all a sad prank?

I had rehearsed a speech in my mind in the elevator. I had a clear course of action and everything. They were supposed to wait for me, separately!

"Wanna join in?" Austin asked.

I was still standing like a moron at the door.

"Sure..."

The hotel room was quite spacious with a King Size bed in the middle. There was a tray with chips, some beers and vodka flasks on the bed. I entered the room unsure of what was meant to happen next. Did I really think it would be like in a movie? I would go to one of the rooms, choose either Kurtis or Austin and that would be it.

Life is never that simple.

"Don't make that face, Ty. It's all good." Kurtis said, sitting on the large bed.

"I'm sorry, I'm just... I'm confused, I guess. To be honest, maybe I'm more drunk than confused." I replied, looking at them both.

Why did they have to be so hot on top of everything?

Austin sat on the bed as well.

"Ty, what we said earlier. That was not the alcohol talking. Fact of the matter is, we both want to be with you. Kurtis is a great guy; I mean for a prisoner." He chuckled at his own joke and Kurtis rolled his eyes. "And I'm a great guy too, I mean, for a soon-to-be divorced man."

I took a sip from one of the beers.

"Ok, so, you both want to be with me. Can you maybe not be best buds then? Cause that's weird!" I said in my most sarcastic tone.

Kurtis stood up again and got closer to me.

"Today was perfect, Ty. For fuck's sake, it literally felt like a dream. And I owe it all to you. You got me out of jail. Without you, I would be rotting there for another year. I don't want to share you with Austin or with anyone else. But I also don't want to finish that perfect day sad and miserable. You knocked at my room. I have no idea if you came in here first or if you tried to go to Austin's before. But right now, I don't even want to know, at least for a few more hours."

As he was speaking, he got even closer until he was whispering in my ear.

Austin joined us. He was standing on my right. I felt shivers going through my whole body.

"Ty, maybe that's stupid, but Kurtis and I thought that we could just enjoy our evening and then tomorrow, we'll go on with real life. I don't want to share you either, but if you choose him, I would rather have this one night with you rather than anything at all."

I was starting to get where they were going with this but I could not really fathom it. I was tired of making mistakes. Would entertaining this crazy idea be yet another one?

"Guys, I don't want to play with you, to make things weird..."

"What if we want you to?" Kurtis asked, slowly grabbing my chin so I would turn my face towards him.

He kissed me.

Kurtis was on my left; Austin was still on my right. I felt their warm bodies both leaning against mine. After an intense kiss with Kurtis, he nudged my face towards Austin. I looked at my former college roommate in the eyes.

For a second, I thought it was over. Austin seemed apprehensive, almost scared. But then, he grabbed my face and kissed me also.

That kiss with Austin was overdue but never in a million years I could have guessed it would happen this way. But it did, in this hotel room, while Kurtis was caressing my neck. In a way, it was fucked up, in another, it was perfect.

I knew I was living one of those rare "once in a lifetime" experience and I let go. I let go of my fears, nerves, frustration, stress, thoughts... I let myself enjoy the moment and this was the start of the most erotic night of my entire life.

Kurtis lifted my top while I was kissing Austin. It became more sensual, our tongues got mixed with each other. My dick was already hard under my pants.

When we stopped, Austin nudged me back to Kurtis and we French kissed each other.

I had both of my arms against their respective bare backs and I moved my hands towards their neck to nudge them closer to each other. Before my eyes, Austin and Kurtis shared a sloppy kiss. I was in awe and I joined them, our three tongues intertwining.

We ended up on the bed, we spilled some beer on the sheets. Fuck, the hotel's deposit.

We did not care about that though; a deposit was a real life's problem. That night was only about pure enjoyment.

The three of us were laying in the bed. I was in the middle, but I did not stay there the whole time, I wanted this to be a real sharing experience. To say the truth, seeing Kurtis and Austin caressing or kissing each other was one the hottest things I had ever witnessed. It was almost as good as kissing them myself.

Almost.

Quickly, the pants fell off and we were playing with each other in our underwear.

It was a foolish thought but I did check if Austin was hard. I mean, I had seen the guy marrying his wife and fucking a lot of girls back in college. I just had to make sure he was enjoying it. He definitely was and his hard cock, proudly poking out of his underwear, was all the evidence I needed.

Fuck, I had forgotten how beautiful his dick was when at full mast. I wanted to stroke, lick, suck, and take it in my ass so badly.

On the other side of the bed, Kurtis was already rubbing his hungry cock against my ass. He was not too bad himself. Think what you want but for me, size definitely matters and both of my lovers for the night were freaking stallions in that department.

The kisses turned into licks on our necks and chests. I bit Austin's nipples and then licked Kurtis' belly button. I stroked both of their dicks still mostly covered by their underwear. They were busy, feeling up my ass. I was in heaven. Austin slid his hand under my briefs or maybe it was Kurtis' hands.

"Mmmmm..."

We took our time. The three of us wanted this to last. I kissed them both some more, the sweet taste of Austin's lips, the firm hand of Kurtis on my thigh. Then, while remaining on the bed, I moved down on them to get closer to their throbbing cocks.

I could no longer wait. Two monster cocks, girthy, veiny, and already leaking through the fabric of their underwear. I had to taste them again.

Finally, we all got naked and I gave them both a blowjob.

I started with Kurtis. I kissed his dickhead first and licked the edges of his meaty cock. I went down on his shaft. So fucking thick and long. Just like I love it! I licked his balls too. We had our routine now; we had been having sex for a few weeks at this point, I knew how to push his buttons.

After this short preview, I went on Austin's. I was so fucking excited to swallow Austin's dick again. Would the sensations that I had experienced in college come back? Not really... They did not. It was so much better than what I remembered!

At 29, I knew my way around a cock. More importantly, I did not wear a wig nor did I have to ploy anything to have access to this treasure, Austin was more than willingly offering himself to me, and that made all the difference.

Once I had sucked the tip of his cock, I could not help myself from wanting to go deeper and swallow the entire thing. Austin was thrusting his hips slightly to push his dick in my throat.

I looked in his eyes and I knew that it was meant to be. He face-fucked me and some tears fell from my eyes. I pushed myself to offer him a sloppy deepthroat, he moaned and I was proud of myself when my nose reached his pubic hair.

After this mouth full, I went back to Kurtis's dick but my two lovers got closer to each other, their legs entangled, I saw two juicy dicks, eager for my mouth and I went for them both at the same time. To be fair, fitting them both in my mouth was impossible.

They were too big, too thick, I do not know how those gay pornstars do it, but I still rubbed them against each other, mixing their precum together in my mouth and managing to put both of their dickheads in, while stroking them. My saliva was a great lube.

They were moaning softly, proof that I was doing a good job.

When I looked back at them, they were kissing passionately. I did feel an ounce of jealousy, reminding me for a split second that real life was not that far away and that this moment of bliss was only temporarily, but I returned to my deepthroat of each of their cocks, and I was back in the fantasy.

Sometimes, Austin would push my head onto Kurtis' dick and reversely. I would gag, spit, choke on their monster cocks, alternating between one and the other, swallowing their balls, sucking up their precum.

It lasted for a good ten minutes until Austin was the first one to lift his legs up and offer his big muscular ass to me. The guy has always loved the rimming, great match, I have always loved to eat an ass.

Bon appétit!

I did not make Austin wait and I buried my tongue in his slightly musky asshole. Deep in his hole, I felt like I was back home. My tongue worked hard to inspect every part of what was once a familiar place. I was stroking Austin's stiffed dick at the same time; I could feel the precum sliding onto my fingers while I was blissfully blinded against his ass crack.

I was smothering myself in Austin's hole when I felt something in my own ass.

"Mmmmmm..."

A tongue.

Kurtis' tongue was rimming me.

Fuck! My dick throbbed and let go some precum on the already dirty bed. Things were bound to get dirtier.

I kept on licking and servicing Austin's hole until I felt like it was time to reward Kurtis for what he was doing with my ass. I said my first words since we had started having sex.

"Lick his." I spoke to Austin, surprising myself by the tone of my command.

He nodded yes, knelt on the bedroom's carpet and crawled towards Kurtis.

Austin was about to suck Kurtis' cock when the ex-con stopped him.

"Oh no. Not my dick." He said with a smirk, lifting his legs in the air.

Kurtis' ass was way hairier than Austin's or mine. His hair was thick and black. His crack was also sweaty as fuck. I wondered if that would be too much for Austin, but again, I was naïve. My former roommate has changed since college.

Austin went in there like it was his favourite ice-cream while Kurtis was asking him to go deeper with his tongue, always deeper. I was jerking off my cock, enjoying the show, not too much though, because it was way too soon to cum. I had to sometimes look away not to explode.

Kurtis was stunning with his large hairy thighs in the air and Austin was out of this world in this submissive position, preparing Kurtis' ass. It was the best version of the "Toss my salad" series that I could ever have imagined. I wanted to see them fuck. I wanted them to fuck me even more. Damn, this was only the beginning of the night.

While Austin kept on rimming his ass, I took care of Kurtis' cock. Austin was enjoying the cake while I was swallowing the meat. Fantastic team work!

I managed to reach Austin's face and I kissed his lips while he was taking some air from being smothered in Kurtis' hairy ass crack. I tasted Kurtis' ass on Austin's mouth. We smiled to each other.

I spat on Kurtis' cock, adjusted my position on his body and we found ourselves in a 69 position. Kurtis was still lying down and he licked my ass and balls while I was deepthroating his dick. Every time I would go down on his cock, I tried to keep my eyes opened to get to see Austin's face below me.

I was gagging a lot and consequently, drooling and spitting all over Austin's face. He got sick of it at some point and spat back the saliva on my face and Kurtis' dick. We just laughed it off. And then, we kissed.

I had experienced some threesomes in my GrindrR days but those have always ended up disappointing. I guess I just had not find the right partners.

After a few minutes, Austin let go of Kurtis' ass to just watch us, he lied down in the bed again, stroking his cock slowly. Kurtis spat in my hole and he started fingering me.

The moans became more intense. We were all sweating a lot at this point and our bodies were entangled once again with one another. I am not sure how but Austin and I ended up sitting on the bed and Kurtis was on the carpet. He sucked both our cocks while I was in a deep French kissing session with Austin.

Austin pinched my nipples while licking my neck and I lost all control. I cummed in Kurtis' mouth. A ton. I could not stop myself and I painted his throat with volleys and volleys of my cum. Kurtis was not one to be scared of some jizz, he kept my cock in his mouth until I was done and he had swallowed the very last drop.

Better than that, now that mine was deflating, Kurtis was able to suck Austin and I's cocks at the same time. Seeing him with his mouth full of our cocks was almost enough to get me hard again.

We took a minute to drink some water (I think we were all done with alcohol at this point), spitting some on each other's faces and bodies. Again, we had a laugh. Somehow, it was sort of raunchy but it also felt very natural.

"Sorry for cumming down your throat without any warning." I said to Kurtis while sucking his nipples.

"I'm sure you'll find a way to redeem yourself." He replied, reaching my ass with his two hands and stretching my ass cheeks apart. "How does it look?"

He asked Austin who was standing up behind me.

"Like a hole ready to get fucked."

Let me tell you this, my dick did not remain soft for long! I mean, how was I supposed to be calm when the two most attractive guys I had ever met had this type of conversations about my own ass?!

"Fuck me. Both of you." I begged.

As if the night could have ended up any differently.

I got in the doggy style position on the bed. I was not sure who would fuck me first. Austin and Kurtis whispered something to each other. When the wet dickhead came into contact with my asshole, I did not know who was about to fuck me. It was only when I started to feel the familiar thickness that I recognized Kurtis' dick.

Austin had been a gentleman and let his new friend go first inside of me.

The fucking was quite rough from the start. We were all feeling the heat and I was not expecting a vanilla fucking. Kurtis pounded my ass hard and I loved every second of it. Well, maybe the first twenty seconds were a bit difficult, but then... the way he was slamming my prostate as waves of pleasure were going through my body...

Best sensation in a world.

Especially, when you are sucking Austin's perfect cock at the same time. They spit roasted me just like I deserved and the three of us were moaning and shouting so loudly that the whole hotel was probably listening to us. Again, who cared?

We were free.

Kurtis started to fuck me in another position, I was lying on the edge of the bed and Austin was holding my legs up in the air while I was still taking care of his cock. He was leaking like I had never seen him, and it was like I was sucking on a dripping slimy faucet.

I have no idea how Austin managed not to actually cum being that much on edge, I guess that he had learnt a few tricks in the past years.

Despite it all, I still wanted more. I was now locking eyes with Austin and I needed his dick in my ass. Shit, I was lubing that thing for more than an hour at this point, I deserved it deep in my hole!

Right about that moment and as if Kurtis had read my mind, he jizzed in my ass. I felt the thick cum pouring in my anal cavity as Kurtis was moaning loudly, almost grunting like a fucking animal.

"FUCK, FUCK, FUCK, take that cum!" He barked, still pushing his dick in and out my hole.

Kurtis achieved to fill me up with his sperm as Austin was watching the whole thing. The type of night you never forget.

Once he had cummed, Kurtis went to sit down in an armchair near the bed. And then he watched. He watched as Austin took his place and fuck my ass for the first time in ten years.

It had nothing to do with all the previous times we had sex or we had played with each other. Now, Austin was fucking me after he had told me he had feelings for me. He lodged his big dick into my hole, well-prepared by Kurtis, and very slowly, inch by inch, he went further inside of me.

"Am I better than the other boys you fooled around with?" I whispered in his ear. I did not want Kurtis to hear that.

"There is no comparison, babe."

Babe. My heart melted as my dick cummed for a second time. I was his.

Austin fucked me and kissed me at the same time. He played with my sperm all over my chest and fed me some. He was also getting to the point where he would not be able to hold off his orgasm but he wanted to cum on my face.

"You love that dick in your ass?"

"Fuck yes... Please, don't stop."

"You like when I'm going hard on you."

"Yeah... Please..."

"I want to feed you my cum, babe."

That "babe" again. Those shivers again.

I gladly obliged, I begged for his cum and he let my gaping hole to get his dick an inch from my face. A second later, Austin sprayed me like he had a fucking hose in his hands. To this day, I had never received that much cum on my face. I was literally drenched. Of course, I was more than happy to lick all of the mess dripping on my mouth.

We were in the middle of the night; it was soon to be dawn and the reality was about to catch on all of us. Kurtis went to take a quick shower while we were finishing off with Austin. I felt a weird weight in my stomach.

We still fell asleep together in the same bed, naked. We barely talked but we cuddled. I was back in the middle, taken in sandwich between the two of them.

I woke up only a couple hours later because someone was walking in the room.

"Kurtis?" I mumbled, while Austin was snoring on my right. Damn, he was so gorgeous, sleeping in the nude.

Kurtis was already dressed. The first rays of the sun were hitting the room which had a beautiful orange colour.

"I gotta go, Ty."

"Where? Why?" I straightened up, confused.

"I know."

I did not say anything. I should have had more courage but I let him figure things out himself.

"You went in room 404 first, right?" He said.

I nodded yes.

"For a second, I thought that you had chosen me but then I figured that you would have gone to the other guy first. The one you would not choose. That makes sense. To close things off before starting a new chapter. And I was the other guy. I mean, I am the other guy."

I started sobbing.

"Kurtis, I... I'm so sorry."

"Don't be. You saved my life."

He came to the bed and kissed me on the lips. One last time.