Fresh Meat At The Prison Pt. 06

All characters are above the age of 18.

*

We were out of prison. We were free but restricted. Even so, I wasn't looking a gift horse in the mouth!

I was supposed to meet weekly with a probation officer.

Since Drake works in the system, he came to my first appointment with me. It probably looked good to show I had someone like him helping me out, and Drake wanted to assess the probation officer assigned to me.

Drake went to Gavin's first meeting, too. He had a different PO and went alone after that. I offered to go with him for company, but he said he didn't want other convicts in the waiting room to get their eyes on me.

Anyways, I wanted to make a good first impression with my PO. I had worn relatively nice clothes Drake had bought me, but honestly, I pretty much looked the same as always.

When it was our turn to go in, Drake led the way with a hand on my back, soothing me and providing much needed confidence.

The PO wasn't like I expected. He seemed young, maybe mid 20s or even younger.

Drake introduced himself and me. The PO shook Drake's hand and gave him a head nod but didn't take his eyes off of me.

I smiled shyly. He seemed welcoming, and I didn't get any creepy vibes from him. He held out his hand for me too. When I met his, he seemed to hold my hand a little longer than necessary.

"Umm..."

He flushed and took his hand back. Gosh, he was cute. He said his name was Jessie and was awfully friendly. I checked in with Drake. His eyes were pingponging between me and the PO in amusement.

Jessie asked if I wanted anything to drink. I politely declined. He hadn't asked Drake, but he politely declined too, looking like he was holding in a laugh.

The rest of the appointment wasn't bad. Jessie, a little less flustered now, fell into giving information about what our visits would like that he had probably repeated a million times.

He said he looked forward to seeing me next week and gave Drake a goodbye headnod.

In the car, Drake pulled me on top of him in the driver's seat. "You did such a good job, Rory boy. I'm very proud of you, and it looks like someone has a crush on you."

"I don't think-" He kissed me bruisingly.

"I don't blame him." He kissed down my neck. "Who could resist you?" I forgot what we were even talking about.

Upon returning home, Drake recounted with laughter the PO's "instant love and infatuation" of me with embelishment to Gavin, who was intrigued.

Gavin accompanied me to the next appointment and declared to Drake later that I was the young PO's first love.

In the meantime, Gavin found an online CPA job. He made a face at the salary, while I bulked at the 6 figures! He said it was fine for now, since it provided such flexible hours.

We cracked open drinks and celebrated all together that night!

......

Because Drake was working, Gavin accompanied me to the next PO visit, too. He said Jess seemed fine but that he wasn't going to take any chances with me, so he or Drake had to go with me each time.

It was a normal visit with Jessie doting on me.

He caught me on the way out and quietly asked, "Are you okay? With both of them? Do you need any help?" His hand landed on my hip.

My jaw dropped, and my mouth made an O shape from surprise. Gavin did look pretty scary if you didn't know him, and I almost forgot that my relationship with the guys wasn't conventional. That was sweet, I guess, that he was checking in, but I didn't quite like his thumb brushing against my skin between the opening of my shirt and pants. I don't think he noticed he was doing it.

"Th-thank you for asking, but I'm happy and love both of them." I slightly ducked my head and blushed. I can't believe he was the first person I told and not one of the guys! Why did I tell him that?

Gavin stiffened in the doorway. I hope he didn't hear.

"Love? Both of them?" Jessie asked, his tense body relaxing a bit. His expression morphed from concern to confusion.

I nodded my head and pulled away from his embrace.

"Okay, that's... good." He patted my shoulder and also looked a little disappointed. Gavin would definitely be making fun of him for his crush later! "I'm glad you're safe. Let me know anytime if you need something, okay?"

"Thank you, but they take really good care of me."

He smiled and stepped back. "See you next week!"

......

Jessie was becoming a running friendly joke at our dinner table, but Gavin was pissed anyone thought I needed protecting from him and Drake.

In other news, I had been accepted into an accredited veterinary technician school at the local community college! It was a two year program. My classes were to start in a couple months. In the meantime, I started volunteering at an animal shelter walking distance from Drake's house. The other volunteers were in similar age to me, and Gavin somehow approved its safety, so I could go whenever I wanted.

I was able to get a student loan, actually with Jessie's help. Drake and Gavin were upset that I wouldn't let them pay. While I appreciated their thoughtfulness, I didn't want to be completely dependent on them.

......

For some reason, I mixed up my dates, and completely forgot about my PO visit one day. Gavin came barreling outside during my yoga session to grab me. I asked to change, but he said we didn't have time, threw me over his shoulder, and tossed me in the car.

It wasn't until we were almost there that we noticed I'm only in short spandex shorts and a tight fitting athletic top. There wasn't anything we could do about it now.

At least, because I was a few minutes late, I didn't have to wait in the waiting room with others and went directly into Jessie's office.

"Hi Jessie. I'm sooo sorry for being late! I mixed up the date and almost forgot to come."

Jessie's eyes ran all over my body. "No problem." He swallowed audibly. "I'm glad you're coming, I mean, here for our date, I mean, appointment. Please take a seat."

Gavin turned to hide his silent laughter. He winked at me.

On my way over, flustered, I accidentally dropped my bag and its contents fell out. When I bent over to pick them up, Jessie gasped then tried to cover it up with a fake cough. Was he... checking out my butt?

Gavin strolled behind me, caressed my ass cheek, then pulled my backside to his groin!!, and "helped" me collect the rest of the items.

Jessie watched unblinking.

We all finally sat down. Jessie's eyes were still roaming my body. Did they seem to get stuck on my chest?

"Rory baby, you're being inappropriate today," Gavin jokingly admonished me.

"Huh?"

"You're wearing such a tight shirt, and your nipples are hard and poking out."

He reached over and flicked a nipple. "Ah!" I slapped a hand over my mouth, looking at Jessie. His eyes had darkened. Gavin flicked my other nipple. "Mh!"

Gavin, ignoring what he just did, got us back on track. The rest was a mostly normal visit, with Jessie's eyes eating me up like dessert.

Gavin rested his hand on my knee. A few minutes later, he moved further up my leg. The heat from Gavin's hand and Jessie's gaze burned into me. I couldn't help wiggling in my seat. Gavin moved his hand further and further, until he got to the hem of my short spandex shorts, teasing the edge. He slipped his fingers under, and Jessie stopped speaking mid sentence.

"And?" Gavin asked innocently.

Jessie started speaking again, distractedly.

Gavin rubbed my inner thigh. He was so close... Jessie's labored breathing matched mine.

When Gavin removed his hand, I whined!

"Well, thanks again, man. Your next appointment's probably waiting," he said and pushed me out of the room. He even made me wait until Drake got home to give me release!

......

The next visit, Drake told me to wear comfortable shorts. I didn't know why, but I wore loose, white sports shorts.

He also drove us over earlier than usual. He dragged me to the waiting room bathroom. Going to a stall, he pulled my shorts and underwear off me! He had a lube square packet that he ripped open with his teeth - so hot - and fingered me.

"Oh mhmm!"

His finger massaged my canal and rubbed all over my walls and, yes, my sensitive spot.

He jacked my dick, making it really hard. His lubed fingers filled me up, the wet sounds echoing off the tiled walls. I was leaking. Just a little bit more...

"I'm close! Yeah!"

He stopped!!!

"No, Drake!"

"I'm sorry, pretty boy, but I promise you'll enjoy it."

"Please, Drake... let me at least suck you off. I'll be really quick. Let me come with my warm mouth around you."

He groaned. "We're going to be late. Come on." He kissed me briefly. I tried to follow his mouth when he pulled back.

He pulled my shorts back on but tucked my underwear in his bag! Ah! In the mirror, I could see my dick jutting out obscenely.

"I can't go out there like this!"

Drake handed me the papers Jessie had wanted me to fill out from last week. I used them to cover myself. I thought my desire might ebb with the prospect of being seen, but I forgot my own heat at being watched. I only got more turned on, even if I was simultaneously embarassed. I entered the office and sat in my usual chair across from Jessie.

"Are you okay today, Rory? You seem flushed."

"What? Oh, I'm fine, really! Thanks!"

"Alright. Did you fill out the papers I asked for?"

"Yes, of course." I looked down at the papers covering my lap. I realized Drake did this on purpose!

I tried to scoot the chair forward. Maybe if I was close enough, I could hide myself behind the desk, so Jessie wouldn't notice. The chair wouldn't budge. I struggled with it for a few more moments.

"They're bolted down to the floor. For when some ex convicts, during our discussions... get upset."

I got up and took the two steps to his desk. Jessie held out his hand. I tried covering myself with one hand, handed him the forms, and quickly covered myself with both hands.

I saw the moment Jessie realized my predicament. His eyes ping ponged between my face and between my legs. Drake was quietly smiling next to me.

My dick was throbbing! It liked the attention. Why was I like this?

Jessie looked over the papers I gave him unseeingly. "Could you clarify something?" He pointed to one of the papers.

"Now?" I squeaked.

"Go on," Drake was enjoying this too much!

Jessie handed me a paper and asked me to point to something, so I had to uncover myself to use my hands.

My dick obscenely jutted out, and we all seemed to catch our breaths.

"You're really beautiful," Jessie commented.

My dick twitched! It basically just said thank you for the compliment!

Jessie groaned and ended our meeting early.

I wonder if he used the time before his next appointment to rub one out to thoughts of me?

When we got back in Drake's truck, he pulled out his own throbbing cock and let me use it to finally fill my aching hole. First he made me lean over the console to give him a sloppy, blowjob to wet his dick. Meanwhile, his fingers poked and proded and stretched my hole. Then, he pulled my lose shorts to the side but made me take my shirt off.

"What if someone sees... me naked through the window?"

"You'd like that, wouldn't you?" He rubbed my nipple. I whined.

I straddled him, and his hands moved my hips agonizingly slowly down his glistening cock that was hard for me. My lubed hole made squeltching noises as I descended on him. By the time I seated all the way down, I was panting. My dick was pointed straight up, outlined in the thin shorts so well that my dickhead was visible. It slightly bobbed while throbbing. I used his strong, secure shoulders for balance to slide up and fall back down on his girthy length. I moaned heartily. My legs were already shaking.

"Did you like teasing your poor parol officer?"

"Drake..."

He held me up, just his tip still inside me. I squirmed, but he held firm.

"Draaake!"

"Did you like it?"

"You know I did! I liked him looking at me... and wanting me... and you watching... I'd also really like your big cock to pound me now! I've waited so long. Please Drake!"

"My beautiful boy." Drake held me in place and fucked into me maddeningly! His huge cock jackhammered up into me. I curled over, my nails digging into his shoulders, my face crushed against his neck. I could barely breathe.

As I used all my effort to hold in place, my legs turning weak, he slipped a hand to my hole, feeling himself entering me.

He pushed a finger to my rim... he - omg! - pushed hard enough for his finger to enter my hole alongside his cock! "Ah! Dra-ahhkeaah!"

Too much! I stretched too much, but I was so turned on and so desperate for release, I made broken sounds and pushed down on his intrusion.

"Fuuuck! Good boy, Rory!" He pulled my rim, stretching me even more.

I bit Drake's neck and came, waves of pleasure washing over my body. My canal squeezed Drake's cock and finger.

"Aw fuck yeah," he stuttered, and I felt his hot come gush deep inside my hole.

......

The next visit, both Gavin and Drake accompanied me. When we entered Jessie's office, I realized there's only 2 seats across from his desk. Gavein pulled me on his lap!

A few minutes into the visit, Gavin whispered in my ear. "Grab the arms of the chair and don't let go." He proceeded to slip his hand down the back of my my pants. His finger ran down my crack, rubbing delightfully up and down, farther each time, until he reached my puckered hole.

I moved my arm, to do who knows what, maybe cover myself or grab him, but his deep voice growled, "Don't let go." I regripped the chair as he teased my hole. He rubbed it without penetrating. I was squirming in his lap.

Gavin's other hand slipped under my shirt. Through my half lidded eyes, I saw Jessie watching me with his lips parted. Gavin tweaked a nipple, and I cried out.

"S-sorry! I-"

Gavin bite my ear. I tried to muffle my moans, but they escaped.

Jessie's pupils were blown, watching with rapture.

"Pleaseee," I asked for relief.

Drake quietly checked in with Gavin. "Dick, no hole, like we talked about before?"

Gavin nodded.

Drake saddled up to the PO. "You know, Jessie, Rory here has a soft spot for you."

"He does?" It was the first time Jessie looked away from me, if only briefly.

"Mhm hmm. And as you can see, he needs some help."

"I can help," Jessie jumped on it.

"You don't mind, do you?"

"No, definitely not. What do you need, Rory?"

My mouth fell open.

Gavin lifted me off his lap. My legs were weak, so I leaned back against him. He circled my waist, slooowly undoing the button and zipper of my pants. He pulled them and my underwear down in one go.

Jessie made a choking sound as my growing dick bobbed in the air.

"He's so smooth and tempting, isn't he?" Gavin asked as he ran his hands over my hips and thighs, teasing but not touching where I wanted him to.

Jessie nodded his head.

Gavin fondled my balls. I thrust my hips out, asking. He finally gripped my dick and lightly stroked me.

"Uhh!" My head fell back on his shoulder.

"Our pretty boy needs his dick licked."

Jessie rounded the desk and dropped to his knees. Wow! What was happening... Gavin let go of my swollen dick to hold me up by my hips.

Jessie gripped the base and breathed on my twitching member. "Do you need your dick licked, Rory?"

"Y-yes, please."

Omg! Was this really happening?

He started with small licks to my dickhead, making me jerk my hips again. "Ah!! Ah! Hmmm!" Precome dribbled out, which he immediately ate up, then chased with his tongue dipping in my slit.

"Ooohhhh! Yeah!" My knees buckled, but Gavin held me upright. Drake approached for a frontrow view, jerking his dick while enjoying the show. He intermittently reached out to tweak my nipples, sending electric bolts down my body.

Jessie engulfed my dick. His mouth was so wet and warm. His suctioning lips slid up and down, causing me to shiver. I was overwhelmed with pleasure. I needed to hold onto something.

"Can I?" I placed my hands in Jessie's hair.

He popped off my glistening, hard dick.

"Yeah, pull my hair," he said and took me deeper.

"Ahh!"

He sucked my balls in his mouth. He could fit both of them at the same time! He sucked them deliciously, his hot, wet mouth enveloping them as he tongued what he could. Mhmmm!

When he returned to sucking my dick all the way to the base with a strong suction of his lips, I was close.

Jessie looked into my eyes and slightly scraped his teeth over my sensitive flesh. "Ohh!" He sucked fervently then did it again. "Ooohhh!" I pulled his hair harder, maybe too hard, but he groaned and sucked with his tongue lapping.

Drake growled, "Gavin, I need to fuck him." His hands tugged his cock furiously with a twisting motion.

I felt Gavin's chest rising and falling against my back. "Yeah, me too." He had been rubbing himself against me from behind. He pulled back slightly and slipped a spit wet finger in me and curled it.

"I- Ahh!!!" I came! Jessie moaned around my dick, sending even more pleasure up my spine and to the rest of my body. His eyes were closed, almost blissing on my taste.

When Jessie slipped off me and got up, there was a wet come stain on his pants. He had come in his pants! From sucking me! Wow.

He leaned against his desk with a smile as Gavin and Drake threw some clothes over me and dragged me out of the office.

As soon as we reached the car, they used me hard and thoroughly in the backseat, one after another, again and again. The car windows fogged over completely. Though the car shook, probably giving away our activities. My dick was so spent by the end that my last orgasm was dry but majorly intense.

......

My next appointment with Jessie was weirdly normal. He didn't mention it, and we didn't mention anything. Jessie did have an obvious erection for the entirety of it, but otherwise it was professional.

Then, we had a few phone visits instead of in person, because with permission, I went to my hometown to visit my family for the first time.