Fresh Meat At The Prison Pt. 03

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Tempting twink loses his virginity.
4k words
4.85
11.3k
18

Part 3 of the 6 part series

Updated 02/23/2024
Created 10/09/2023
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All characters are above the age of 18.

*

"I have to make it sound like I'm beating on you, or others will think I'm going soft again." Gavin could tell I was panicking. "Don't worry, pouty lips, I'm not actually going to hurt you"

"Are you sure?"

"We just need the sound of skin on skin. How about a spanking?"

I yelped!

"It's the best place I could hit you. Everywhere else would hurt."

"That'll hurt too!"

"We'll see... Okay, grab on to the top bunk's board. There we go."

Gavin went to pull my jumper down when I tried to twist away. I was nervous.

"Come on, I said we need skin on skin."

Oh yeah... he undressed me then pulled my shirt off too.

"Why did you take off my shirt? I thought you were only going to hit my butt?" I asked.

"That is for my viewing pleasure."

I blushed!

He spread my legs, and I arched my back, popping out my butt, which earned me an appreciative moan.

I was happy he was getting into it, but my flacid dick swung underneath me. I was not into pain.

Swat! The sound echoed loudly.

"Oh!"

He palmed each cheek then brought his hand down with consecutive hits. I moaaaneeddd. What was happening? This felt good! Electricity zapped from where he hit me to my dick and balls and hole.

He continued to caress me, and I pushed back against him.

"Mhmm you want more?" He pulled off, paused until I thought he might stop, then came down hard!

"A perfect handprint on your smooth ass. I better even it out."

Swat! "Ugh!!" I couldn't hold my head up anymore and when I hung my head, I noticed my dick was rock hard and throbbing! A pearl of precome built at the tip. The next swat knocked my hard dick against my abs and left a trail of precome on me.

I felt hot all over and started meeting his spankings. He carried on and on until he was breathing just as hard as me.

All of a sudden, he shoved a finger in me. I wasn't expecting it, so it shoved in without much resistance, but it was mostly dry with just some spit as lube, so it burned a little. He spanked me again. Oh wow it was even better with him in me! He twisted and turned my insides.

He added a second finger. My hole stretched more, and the spankings only added more sensation. He barely traced over my prostate, and I blew! Ohhh!

How did every orgasm he gave me seem more intense than the last?

I tried to reciprocate with a blow job, but he said later, because we were late to dinner.

During dinner, Gavin and I got our trays and sat at our usual table. When I went to sit next to him, my ass was on fire on the hard bench! I immediately stood back up and shifted foot to foot. I didn't know what to do. Gavin understood, wrapped an arm around me, and pulled me to his lap! A few of the prisoners murmured about it, but mostly nothing happened.

"Is this better for your cute red bottom?" he whispered. It still burned but definitely not as bad as the bench. I smiled and nodded. I could feel his cock swelling against my sore ass. I wiggled a little, and Gavin swatted the side of where my red skin was under my pants. "Naughty boy, stay still," he ordered.

Then he fed me! Every few bites of his own - he was a fast eater - he'd hand feed me. I think to others it looked like a control thing, but for me, it made me feel cared for. Towards the end of the meal, I closed my lips over his fingers longer than necessary and sucked. His outward appearance didn't change, but I could feel the tension in his body. I sucked more and more with each bite, until he said, "Enough. We're done."

He brought us back to our room and fucked my mouth relentlessly. I came in my pants hands free!

......

The three of us were playing cards when Drake stated, "I want Rory to learn some self defense."

"That's a great idea!" Gavin was rarely so excited. "Pouty lips?"

"I'm definitely open to learning, but how much do you actually think it'll help?"

"Whatever amount of time it buys you in a dangerous situation is a bonus."

"Oookay, but all the other guys in those courses taught by volunteers are kind of scary, and I don't like anyone but you two touching me. I guess I'll bear through it..." I was acting sulky even though I knew they brought it up for my own good.

Drake flipped his cards upside down on the table, "Pretty boy, you don't have to worry about other filthy men. I'm going to teach you myself!"

"Why didn't you say so from the beginning!"

"It was implied."

Gavin sighed, "You still don't get it do you? Others touching you isn't even an option."

"When do we start?"

"How about tomorrow in the multi-purpose room? There's almost no one there at certain times. I'll reserve it for us."

......

I'd been wondering for a while, and that night, cuddled up in bed with Gavin, I thought it was as good of a time as any. "Can I ask you a silly question?"

"Of course."

"I'm yours right?"

"Yes, that was a ridiculous question." His hands tightened around me so tightly it made it a difficult to take a deep breath, but I liked it.

I smiled warmly even though he couldn't see it. "No, that wasn't the actual question. Sooo why, um, how are you okay with our, uh, relationship with Drake?" I exhaled and took another breath. Gavin waited patiently. I just didn't know how to ask this. "Why don't you mind, or, you even seem to get off on it when he... touches me, but you hate others touching me."

"Does that bother you?"

"No!!! I like it a lot, like a lot a lot, but... why do you like it?"

"Hmmm..." He nuzzled my neck. "I didn't plan on it. It started out as the best course, and it worked out. I love watching you fall apart and lose yourself in the moment. Finding your kinks and adding fuel to the fire gives me imense pleasure."

"What? I- I don't have kinks! You're the kinky one!"

"Yes, my Rory." He kissed the top of my head. "Anyways, I like that you like it. That's probably what makes me the happiest. There's also the added sense of security, mainly physically at first and now emotionally too. It makes me more comfortable knowing there's another person who can help protect you and cares for you. And Drake seems to fit in with us. We all get along."

"You mean he follows your orders too."

"Well, he certainly has a dominant side, but yes, I do prefer to have the final say. That's not so bad is it? It seems to work well for him too."

I twisted up and gave him a lingering kiss, then settled down for the night.

......

The first self defense workout session, I hadn't known what to expect, but it was a difficult hour! Drake's hands were aaaaall over me. He was so close to me and feeling me up and his breath was on my neck. It was tortureeee. By the end of it, I was a horny, shaking mess, but Drake just thought it was from the exersion of working out! Though some of it probably was, because he also worked me hard! He had official work to do right after, so he left quickly when we were done.

I barely made it to my room before shoving my shorts off and taking my dick in hand while pumping myself full of my own fingers!

That's how Gavin found me. "Oohh, baby boy, what a nice surprise. Let me help you with that." He took over, and I finally came!

......

The second session, I didn't wear underwear beneath my detention center provided work out shorts. I wanted Drake to know, and I wanted Drake to use me. My dick was slowly tenting my front, but he couldn't see yet. He had his arm around my neck in a fake hold, and I subtley pushed my ass against his growing bulge. He seemed to shift his hips back to give me room, but I followed. I asked a question to distract him, so it didn't seem like I was doing it on purpose! He started shifting his hips against me slightly as he showed me where to put my arms. He gave me instructions in a low voice, his mouth brushing against my ear. My jaw slackened, and I earnestly grinded my hips back against him. His other arm wrapped around the front of my waist as his hard cock slipped between my cheeks, just covered by the thin material.

"Oh yes!" I cried as he rubbed against my hole.

"Are you not wearing any underwear?"

"Nu huh!"

"Roryyyy," He moaned my name with a few last thrusts. "I can't believe I'm putting a stop to this, but this is serious. I'm trying to teach you skills that might end up saving your life. I care enough about you to take this seriously, so you should too."

He seemed so stern about it, and I felt like I was in trouble at school or something. "I just wanted to have some fun with you..." He opened his mouth, probably to lecture me again, but I continued. "But I get it. I'll wear my underwear from now on," I mumbled and glared at him. He booped my noise and mumbled something about me being cute.

"Alright, back from the top."

......

Day after day, every training session made me hornier and hornier. I always returned to the room with a big itch to scratch. A few afternoons, Drake stopped by and ravaged me like I needed, but most of the time, I had to wait for Gavin.

And Gavin was so good to me! Though, sometimes he still pushed me way out of my comfort zone.

It was the end of another day, so I stripped as soon as I got back to our room and folded my clothes on the shelf. I was perpetually half hard these days.

Gavin entered shortly after, sat on the bed, and patted his thighs. Without hesitation, I went to sit on his lap sideways, facing the door. I kissed him with enthusiasm, sucking on his lips and tongue. He always really liked that. His hard cock pressed into me, and he moved my ass against himself.

He reached under the mattress to pull out some lube. I smiled brightly and put my arms around his neck, kissing the side of his face and neck. He held the bottle above me and generously squirted lube on my dick standing straight up at attention, already fully hard without being touched. The lube tantalizingly dripped down my erection and onto my balls. Gavin capped and hid away the bottle again. One of his arms wrapped around my waist and the other stroked the side of my thigh.

"How was your day?" He asked.

I was wiggling on his lap, rubbing against his thick cock poking up. The anticipation was killing me.

"Fine," I answered breathlessly. "How was yours?" The arm around my waist sneaked up to rub my nipples. "Ah hpmh!"

"Better now with you on my lap, naked and writhing." His eyes raked across my body.

"My day would be better if you touched me, Gavin! Come on already!" I whined. First Drake, and now Gavin. They were driving me crazy!

"Ooh bratty Rory is out to play I see." He teased the side of my balls, lightly brushing against them. I gasped. He was so mean.

I leaned in and nipped his lip. He growled and bit my lips back, devouring my mouth, and finally grabbed my pulsing dick and started stroking.

"Yeeesss, thank you, Gavin. You're- ugh - you're the best."

He smiled and watched my face's reactions as he played me like an instrument.

"Hey, Gavin! About the- oh sorry, man, I'll come back later." A prisoner with a clipboard said at the entrance to our room.

"No need, now is fine," Gavin replied. My eyes popped open and he had a sly grin on his face, which he smoothed out to a neutral expression when he turned to the guy at the door.

He kept stroking me! I moved to try to scramble off his lap but his arm around me and his tight grip on my dick kept me in place.

"You ask Gavin ye-" another guy joined at the door and stared at the scene. Which was me! Fully exposed!

"What are you going to ask?" Gavin calmly asked as I was falling apart, a whimpering mess, on his lap.

"We uhhh wanted to ask who you wanted the last person to be on your team for the three on three basketball tournament tomorrow," guy 1 said. He tried to keep eye contact with Gavin, but his eyes kept sliding back to me, trailing all over me, mostly getting stuck on my face and especially my dick in Gavin's large hand. Guy 2 didn't even try to hide his stare and was completely fixated on me.

"Hmm let me think," Gavin said as if needing a few minutes to seriously consider this important thought. He thumbed my head, and I gasped. He picked up the pace going from base to tip. The schlick schlick schlik of his pumping very audible and distracting. Oh no, I was close. I hoped he answered soon, so they'd leave before I blew!

Schlick schlick...

"How about Josh?" Both guys' gazes snapped back to Gavin, confused. They forgot what the conversation was about!

Gavin's eyes narrowed, which instilled enough fear for their heads to clear a bit.

"Sure, great! Josh it is!" Both guys hurried to leave.

"Now where were we?" He turned his attention back to me.

I was slack jawed and sooo turned on but also embarassed!

"I can't - oh! - can't believe you - mhmm - did that!" Gavin twisted at my cockhead on each upstroke. I moaned unabashedly since we were alone again.

"Come for me, my bratty boy," Gavin commanded, and even more embrassingly, I did instantly. I couldn't do anything but hold his gaze as pulse after pulse wracked my body and hot come covered my abs, chest, and his hand. He kept going, wringing me out and milking me dry of every drop.

......

We were quite a few training sessions in when I went to our regularly scheduled time in the multipurpose room, but Drake wasn't there. I waited. 10 minutes after the hour, Gavin strolled in saying Drake had something come up, so he asked Gavin to check my progress.

I told him our regular routine, which he agreed to. I started getting turned on again as usual, and Gavin didn't miss it. He watched me with heavy lids. Maybe Drake didn't miss it either, but chose to ignore it, so he could keep teaching me.

Gavin, however, used the excuse of sweating to take his shirt off. Wow! I was always impressed with the view of his big chest, wide shoulders, and defined abs crunching. He saw me looking and pumped his pec muscles back and forth, woaahh. I giggled. I also took my shirt off. I could tell he appreciated that too.

"Drake's done a good job of teaching you the basics," he praised.

We did a few more exercises, both of us completely hard. His hands brushed over my nipples. "Ughh." His hands brushed all over me! My sides, my abs, my butt, my groin.

"Strip," Gavin commanded. He also started to take his pants off. "We should practice for if you're ever in the showers or changing, right?" I laughed more. I didn't care what silly excuse he made. I always loved being skin on skin with Gavin!

He half-heartedly went through a couple more exercises. Wow, this was so much better naked!

Then he just up and threw me to the ground on my back. He came over me, "Oohhh!!" I moaned as we had full naked body skin on skin contact. I loved feeling every part of him against me. His heavy, muscular weight encompassed me completely. I wrapped my arms and legs around him and kissed him. Our dicks rubbed against each other. He kissed me silly and then some. I felt like I couldn't breath but that I no longer needed to.

"You're so irresistable," he growled.

"Then don't resist me..." I breathlessly replied.

Gavin trailed licks and kisses down the length of my body, avoiding my dick, ugh, to between my cheeks. He licked teasingly around my rim. He nipped my right ass cheek!

Then he stuffed his large wet tongue into me! In and out, he pumped. "Yeees yes yes yesss!" I pushed up against him.

He paused and flipped me on my stomach. My cheek was shoved against the workout pad. I reached behind me and held my cheeks apart for Gavin. "More!" I begged him.

His big, wet tongue thrust so good, but I still needed more. I had the urge to be filled up. "Moooreee!"

He pulled up then walked to my front. Huh? Oh!

He presented his cock, and I slurped it down like my favorite treat. "Get it dripping, baby boy," He grunted through my licks and sucks, but it was over too quickly. "Much more and you'll make me come." He pulled out. "Next time I blow, it'll be deep in your tight virgin ass." I groaneddd.

Gavin returned to my backside and spanked my cheeks! Oof! Shaking them real good!

He spit on my hole then spit on his cock. "There's no stopping now, my Rory."

I braced on the matts.

He rubbed his cockhead against my hole. I pushed back against him. "Ask me for my cock."

"Please, Gavin, will you give me your cock? I want it so bad."

He slapped himself against my hole. "Oh! Ohh! Please!" I was so hard and my hole felt so empty. He continued to tease me.

"I want your monster cock to rip me open and fill me up so good! I want you to fuck me until I see stars and can only think of you, because I'm yours, Gavin. I want you to do everything you want to me."

"Fuck yes, you're mine!" He growled and added pressure until I opened enough for him to start slipping inside. I was stretching and stretching. Omg, when was I going to be wide enough to take his thick length? I moved my legs around hoping to make more room for him or adjust better, but it didn't.

What did help was him working my dick with his hand as he pushed his deeper inside me. "I know it might hurt a little at first, but it'll feel better soon, so be a good boy for me and take it."

I did really want to be good for him. He slipped deeper and deeper.

"Fuck, your tiny hole taking my huge dick looks so hot. One day, I'll record it, so we can watch it together as I take you again." It went on and on.

He finally bottomed out. I felt his balls and thighs at the back of mine. We were both panting and sweating from the exertion. I was so full. He was big, too big. I felt past capacity. This is what I always wanted, to be full and overflowing with Gavin in me.

He waited for me to adjust, running his hands up and down my back and sides. He leaned forward and sucked multiple bruises on my neck. He returned to my dick and jerked it.

"Mhmm," the pain subsided to a dull throb and all I felt was pleasure, a pleasure that was building. I shifted my hips, and that's all Gavin needed to start pounding into me. He gripped my hips in his bruising manner. He slid out slowly then rammed into me. "Oh yes!! Ah!" He continued over and over. My throbbing dick swung below me with each thrust. My fingers dug into the mat.

Gavin was grunting through his thrusts. "You're virgin hole is so tight. Shit! You're so good. So good for me."

He rammed into me a few more times before pulling out. "Ohh," he moaned. "You're already gaping for me. Damn, your ass is sexy. Everything about you is sexy."

"I want to see your face." He flipped me on my back, pushing my legs up to my chest and slammed his cock back in me! I yelled in ecstacy! He leaned over me, our faces so close we were breathing into each other's mouths. His tongue licked my lips then started tongue fucking me in synch with his cock. I was on fire and moaned and squeezed my arms around his shoulders. He picked up the pace, and my nails dug into his back. He growled and thrust into me harder. His balls slapped into me. The sound of them heightened my pleasure.

He slightly pulled back and lifted his body. "Are you ready?"

He shifted his angle, and "OOOOMGGG!! Ahhh!! Yes!! Gavin, Gavin!!!" It felt like I couldn't breath from the pleasure. It was perfect, beyond perfect. He was so rough with me. He was so overcome with his desire for me, he was losing it too. It thrusts lost their rhythm, but he slammed into me over and over! His hands were already bruising me, his short nails digging into my skin, almost drawing blood.

"Rory, baby, I'm gonna come," his voice was so deep I barely understood his growls.

"Give me your come! Fill me up, so I know who I belong to!!" I shouted.

"Aaahhh!!" He let out a pained groan, I felt his cock begin to jerk, and he palmed my dick. "Come with me."

I immediately spasmed around him, choking his cock which spilled hot gushes of come deep inside me hmmmm! and come shot up between us from my dick. The pleasure flooding my body was unmatched. He took my mouth in a sloppy kiss as we both rippled with ecstacy. It seemed to go on forever. My vision blacked out for a moment, and I was dizzy. Gavin collapsed on me, his weight crushing, and oh so good.

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