Thirteen

Hello, and thank you so much for all the sweet comments you guys have been leaving, they make my day and thank you for all the patience and support with the last two parts😅

You guys are so incredibly sweet and I read each and every comment, I hope you guys enjoy this one☺️☺️

Also warning, there maaaay be some sexual themes in this chapter

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•Aaron•

As the night dragged on I stayed awake in my bunk, biting my lip and looking at the ceiling. The two lovebirds were fast asleep below me and I couldn't help but to let my mind wander.

Jackson.. the little one. He was really something. A smirk tugged at my lips and I wondered exactly how much I could get for a kid like him.

I saw that guy, Henry walk down our row of cells and we made eye contact a split seconds before I looked away and scoffed. I didn't like the looks of him.. he was too chummy with loverboy 1 and loverboy 2 beneath me. Don't get me wrong, they seemed like okay people, but that was the problem.

I couldn't stand their goody two shoes attitude and I was practically clawing at the walls. A thought made it's way into my mind and I bit my lip.

"Ay, patrol guy."

I sat up in bed and I slipped myself off the top bunk, walking over to the cell bars.

"Pst, over here!"

Henry turned around and waltzed over to me, arms folded across his chest, a dominant look in his eyes.

"What do you want?" His voice was stone cold, much different than how he talked to the two knuckleheads I slept with.

"When's the next visitor day?" I started with that, and it took me a while to register what I should say to him and keep to myself.

If I could get a handle with my men on the outside I could be bailed out, roughly the same time as the kid got bailed out and once we were on the outside I could hunt him down and get a pretty penny for him.

I smirked to myself.

Wonderful idea, I just needed time and information..

Henry's eyes narrowed and he leaned against the wall behind him.

"What's it to you?"

I growled. I didn't have time for bullshit like this! Calm down, calm down, I could probably find out through someone else..

"Family," I spat out on impulse. "Gotta know how they are.. when is it?"

Henry's eyes softened momentarily before getting that same stone cold look to them.

"Two weeks.. need me to read you a bedtime story while I'm at it?"

This fucker..

I kept my cool and nodded, thanking him bitterly and crawling back up to my bunk, looking at the ceiling again. Sleep didn't find me easy.

•Jackson•

Early in the morning Henry came to pick me up from the cell to bring me to the infirmary. As you would expect, it was a prison infirmary and it wasn't the greatest but there were some nice nurses. I sat down on an examination table with Henry at my side, watching over me to make sure the nurses did their job.

I looked up at him for reassurance when the nurse told me to strip down to my boxers before the doctor came in to check me out and Henry gently tousled my hair, helping me get undressed once the nurse left.

"It's alright, little guy." He reassured gently, slipping my shirt off over my arms.

I unbuttoned my pants and got them off myself only because I'd be much too embarrassed if Henry did that for me.

A couple moments later the doctor walked in, smiling softly at me.

"Hey kiddo, how have you been feeling?"

My face reddened a little and I played with my hands.

"Pretty okay.. my skin is still really sensitive but um the cotton sheets and clothes have helped a lot. And um.. I I think most of the rashes have gone away."

The doctor, an young man probably in his early 30's was one of the only people I trusted here. He nodded and listened intently at everything I said, asking my permission before he gently looked over my back and arms and where I usually broke out.

He nodded and smiled.

"And has the lotion been helping any?"

I nodded and blushed.

"A-a lot actually, thank you!"

He smiled and wrote something down on his board. "And how have your eating habits been?"

I bit my lip.

"Um.. they've been okay.."

Henry gave me a stern, dominant look and all of my lies immediate crumbled.

"Well um.. n-not so great.. I've been skipping breakfast because it makes me nauseous and I usually don't have much for dinner.."

The doctor frowned a little.

"How about.. we try something small and bland for breakfast and see how that goes?"

I nodded timidly and Henry gently tousled my hair, smiling down at me.

I felt a little shy to have Henry with me but he usually came with me to my infirmary visits.

I awkwardly tried to cover up my boxers and my bare thighs with my wrists and hands, wishing I had a little more to cover me.

"Now, I just want to check up and see how you're doing from a few weeks ago. Have you been sexually active recently?"

My face burnt bright red and I shook my head.

"N-not since Santiago came."

The doctor nodded and chuckled a little.

"Don't be so bashful, this is your health, not the 9th grade."

I nodded timidly and I honestly wished Henry hadn't placed a reassuring hand on my lower back because my dick took it another way.

I covered myself up even more and died on the inside when I heard the doctor say,

"Alright well, I'll need to do some routine checkups just to see if your sexual health is in perfect condition. From when Jonas was handling you I just want to see if you've healed. Please, bend over the exam table and remove your boxers."

I felt my heart race and my face got bright red.

Of course, of course me.

Thank you universe, right when I pop a boner suddenly my boxers need to come off. Great!

I got up hesitantly and tried to cover myself with the exam table as I slowly slipped my boxers off and leaned over the table, hoping my legs could hide my awkward boner.

"Spread your legs please."

Oh fucking come on!

I shuffled my legs apart and bit my lip, stuffing my face into the exam table's uncomfortable sheet of paper.

Henry chuckled in amusement and gently stroked my hair back and in that moment I noticed the bulge in his jeans, causing my face to heat up even more.

The doctor gently spread my bottom and looked over my hole, humming to himself.

Oh for goodness sake please just get this over with..

"Alright, Jackson I'm going to have to look further, this may be a little cold, I'm going to have to stretch you out a little so I can see better."

I groaned softly and Henry kept stroking my hair back, enjoying the show.

After this I was gonna give him a stern kick in the balls for that little chuckle he let lose. This was not a laughing matter!!

I gasped and twitched a little when I felt something cold at my entrance. Henry's hand left my head and I audibly whimpered.

"Doc, could he be in my lap for this? It might comfort him a little more."

Oh FUCK YOU, you know what this is gonna do to me!!

The doctor nodded and I bit my lip hard.

Henry smirked and got up on the exam table, letting me nuzzle my face into his lap as he held onto my hand and stroked my hair.

"Good boy.." He whispered.

My cock twitched and I wanted so desperately to yell at him to knock it off but I knew that definitely wouldn't work.

I felt something at my entrance and I whimpered softly as it pressed into me and I couldn't help how my cock hardened. I looked up at Henry for reassurance but he just had this hungry, seductive look on his eyes that made me sink down submissively.

This was humiliating but for some reason I just kept getting more and more aroused..

"You'll feel a little bit of pressure.."

The stretching begun and I clung hard to Henry, letting out little wheezes and closing my eyes hard.

"Shhhh, shhh..." Henry stroked back my hair.

"That's it.. relax,"

I tried following what he said but I completely lost it when the doctor's gloved finger was inserted further into my bottom.

"I will have to check your prostate too, just make sure it's not swollen."

I let out a shameful moan when he gently pressed his finger in further. His long, slender fingers would find it easily.

At this point I was panting softly and when I felt him hit my prostate I flinched and some pre-cum leaked out of my already hard as hell cock.

I could tell Henry must be uncomfortable by how hard his cock was straining against his jeans and I could feel his eyes boring into my bottom.

The doctor smiled softly.

"There you go, just relax, I'm going to start moving a little bit just so I can fit something inside you that'll allow me to see everything. First I'm going to check your prostate though. Just relax and you may feel.. a lot of pressure.."

He pressed his finger in further and I couldn't help the moan that escaped my lips as they pressed right into my prostate. The lubricant felt so cold and I could feel the abundant amount he used gently dripping down my bottom.

Henry let out a soft, territorial growl as the doctor gently felt around my prostate, making sure it wasn't swollen or damaged.

His fingers gently gripped my hair and the pain coupled with my prostate being massaged made my thighs tremble with pleasure.

The doctor gently slipped his finger out and I heard him walk to the other side of the room, preparing something.

"This may seem odd,"

Oh you'd be surprised. With how my day was going already? Bring it on.

"I'm going to have to insert this into you,"

I couldn't tell what it was but by the way Henry tensed up I got nervous. I looked back to see the doctor holding a decently sized butt plug.

"Just to stretch you out. I'd like you to wear it all day, taking it out to clean yourself and of course, relieve yourself. I need you to be nice and stretched out and then I'll see you at the end of the day to continue the examination."

I whimpered softly into Henry's lap and bit my lip.

"I'll leave you two here, and I'll give you some privacy to insert this into yourself."

Which basically meant I would have to get Henry to do it because I have no fucking idea how to use a butt plug.

Then it dawned on me.

"S-sir..? Can.. can Santiago come in here too..? J just to help..?"

The doctor hummed to himself.

"I don't see why not."

A couple minutes later the doctor came back with Santiago and he stiffened a little, a bulge hardening in his jeans.

"Baby boy.. goodness, you look.. ravishing..~"

I whimpered and squirmed a little, Henry still soothingly stroking my hair.

"My my, I'd like to know what that doctor's secrets are..~"

He came up behind me and gently stroked a finger down my hole, causing me to shiver.

"Henry, would you like to give me some assistance here~?"

"With pleasure~" Henry's voice had a husky, dominant tone to it and it caused a shiver to go down my spine.

Well😳 This was an interesting chapter

Um *cough*

I hope you enjoyed that

Uh

I assume you can guess what happens next