The Pines

The Pines

Disclaimer: This story is fiction. It deals with interaction between males including oral and anal. Any person under 18, or anyone living in a state or province where reading these stories is illegal should leave this site now. Adult gay content.

Chapter 2

Gerry arrived at 0830. He walked inside and stood waiting.

"How was your night Gerry?"

"It was okay Sir, but some of the boys called me stool pigeon. I don't know what that is Sir."

"A stool pigeon is someone who spies on other inmates for the guards."

"I would never do that Sir."

"I would never ask you to Gerry. Now I see by your records that you finished grade ten and were a good student. Would you like to continue school while you are in here? You could get your grade twelve."

"Oh yes Sir. I like school."

"Okay Gerry, I'll have a correspondence program set up for you. You can access here while you are with me and in your cell via the computer."

"There isn't a computer in my cell Sir."

"Actually there is Gerry. It is embedded in the wall above your desk. It is another privilege that can be earned in here. Eventually you will also be able to send messages to your Dad or friends."

"I got no friends Sir and I never want to talk to my Dad."

"Very well Gerry. Would you like something to drink? Coffee, tea or maybe a coke."

"Can I have a coke Sir?"

I got up and walked into my den part of my office. I showed Gerry the refrigerator.

"Gerry you can have a coke, beer or anything else you want anytime you want while you are here."

Gerry grabbed a coke.

"Thank you Sir."

"Gerry because you were in school I know you know how to operate a computer. You can use this desk. You can bring up the inmate list and order the boys here I want to talk to."

I showed him how to do it and the first boy was on his way to my office.

When ever I got near Gerry he'd start to plump up so I knew he had more than a passing interest in me. That was fine, because I really wanted him.

"We will interview four boys today Gerry and this afternoon I'll show you what you didn't have a chance to see yesterday."

"Okay Sir."

The four young men that I interviewed that Saturday morning were not really remarkable. All were adjusting to the rules and regulations. None I was interested in. Neither was Gerry. I asked him after each interview.

I had a feeling Gerry was only interested in one person, Me."

After the last for the day had left, I took Gerry on a tour of the administration building. I told him after lunch we'd go outside. Last place I headed for was my bedroom. Not to do anything, but to take a big crap and piss. I left Gerry in my bedroom while I did my stuff.

When I came out, Gerry was sitting on the side of my bed. I took off my uniform and pulled on shorts.

"Sir, can I suck you off again?"

"Do you want to Gerry?"

"Yes Sir."

I removed my shorts and underwear. Walked to Gerry and pulled him up. Then I tossed him on my bed. He got a real scared look until I lay besides him in 69 position. My cock was in front of his face so he just started to suck me. When I took his cock in my mouth, he stopped and moaned. He then went back to sucking me harder. I did notice he was taking more of me.

Gerry was one very horny boy and didn't take very long to blow. He also got very sensitive. I contented myself with licking his balls and butt as he sucked me. Gerry had that nice boy smell. Soap mixed with his sweat that turned me on so much. It didn't take long before I let him have my load. Like before he just swallowed and then licked me clean. We sat up beside each other.

"No one ever did that since Benny Sir." "Well you taste real good Gerry and I will be doing it lots. Now let's have some lunch."

"I'm almost full now Sir." He giggled.

We had lunch and then I took him outside. I showed him everything and then led him to the recreation center.

"Do you like swimming Gerry?"

I don't know how to swim sir."

"Well you can get taught here too. Once you have that privilege you can swim here when ever you are off duty."

We went back to my quarters. I mixed myself a drink and told Gerry to help himself to what he wanted. He then sat beside me. I put my arm over his shoulder. He just snuggled up close to me.

"No buddy hugged me since Benny Sir."

"Well I'll hug you lots Gerry."

Gerry was definitely having an effect on me and that might or might not be a problem. I did have options. I could leave it the way it was with him sleeping in his cell each day. The other inmates might still be calling him a stoolie, but I doubted they would go any further.

I could move him her to my quarters permanently. None of the guards would have a problem with it and neither would ISSI. What I did here as Warden was my concern only and no one else's. The problem with moving him here was he could never go back to a block. The inmates would definitely take action against him when they found out I was fucking him and he was fucking me.

The other problem was there were other boys I wanted in my bed. I doubted Gerry would like that much.

While I was thinking about it all I hadn't realized I was playing with Gerry's butt. I actually had a finger inside him.

"That feels good Sir. Will you fuck me now?"

When he said that I realized what I was doing.

"You like that Gerry?"

"Yes sir, but I really want you to fuck me."

"Gerry, if I fuck you, you will be in pain for a long time."

"I know sir, but it hurt real bad when Benny did me the first time. It felt real good after a while."

I knew I was going to do what he wanted, but not right away. I stood up with him in my arms and walked to my bedroom. I think he thought I was going to do him right then because he got a big smile on his face. Instead I walked to a door off my bedroom. I used my thumb print to open the door and walked in. I set him down.

"Gerry, I'm going to explain something to you first."

"If I do what you want, you won't be able to return to your cell for a while and maybe not ever. You would have to stay in here."

"You mean this would be my cell? This is nice Sir."

It was a real bedroom, with a real double bed, desk with computer, an easy chair and its own bathroom.

"You also must understand that there are other boys I want as well. So when I had them over, you would be alone in here."

"That's okay sir. I think Jerome is one boy. If I was bigger I would like him too. He told me in the hallway he'd never hit on me again unless I wanted it."

That I did not know. So maybe Jerome did have a change happening. Well I would see.

"Come along son and I will explain everything. Don't worry, you will get your wish later, although I think you might just regret what you wish for,"

We went back out to my living room and I gave him a beer.

"I never had beer before sir. My Step Dad didn't like alcohol in the house."

"Well you might as well get used to it Gerry."

"Okay Sir."

"Gerry, while you were in the Sacramento holding Center, did you get abused lots?"

"Well I had to suck off lots of guards and even a few boys in the shower, but only one guard fucked me. He wasn't very big and it felt real good. He did me three or four times a week. Boys I sucked almost every night in the showers."

"Gerry, later after I have cleaned you out I will fuck you as you want. Because you want it to happen it is not classified as being forced. Now if Jerome had fucked you and you didn't want him to, it would have been called Rape. He would have been charged with Rape and immediately transferred to Edmonton for trial. The recording of your rape would have been used and Jerome would probably receive 20 years in a class 1 facility. If you had died, Jerome would end up on death row and be executed less than six months later. There would be no appeal."

"If you did the same thing you would end up the same as Jerome."

"I understand Sir, but I would never force anyone Sir."

"I don't think you would either Gerry, but like I said you are asking me to fuck you, so you can't come back and say I raped you."

"I would never do that Sir."

"Gerry, you have sucked me off twice. Now you want me to fuck you. The next time you want to suck me you have to suck all of me."

"But you are real big Sir."

"No matter Gerry. You want all of me in your butt so you have to take all of me in your throat."

"I'll try Sir."

"Okay Gerry." I pulled him onto my lap and wrapped my arms around him.

He almost purred.

I reached over and keyed my intercom.

"Yes Sir."

"Sgt/Major. Transfer Watson's records from cell block A to my quarters."

"Yes Sir. I was wondering how long before that would happen."

"Have you found someone Sgt/Major?" "Yes Sir."

"Good for you. Notify all personnel they don't need my permission to accept a boy into their service."

"Yes Sir and thank you Sir."

I turned to Gerry and he had a big smile on his face.

"So now you are here permanently Gerry."

"Thank you Sir."

"You might not thank me later Gerry."

We ate dinner in silence. I'm sure Gerry was thinking of the consequences of his agreement to stay in my quarters. I am also sure he didn't know exactly what I would require from him. He would become universally hated by the other inmates. That I was sure. When we went outside on my tours he would be wearing shorts and a t-shirt, no coveralls for him. He'd also have to service me anytime, even when other inmates were present. I'm sure he didn't know that. In Reality he'd become my suck and fuck boy toy. It was simple. Rule number one.

You will always do exactly as you are told immediately.

After dinner we went and watched the news on my huge 3DHD television.

He had one in his new cell.

As the night wore on he became more nervous.

"Are you scared Gerry?"

"A little Sir. You are way bigger than anyone I had before. I know it will really hurt Sir."

"Not to late to back out Gerry."

He sat for a few minutes.

"Sir. Will you please fuck me." He said.

"Yes I will Gerry. Then there is no turning back the clock."

I stood up with him in my arms and headed for my bedroom. After I undressed I took him in the bathroom and gave him an enema. That cleaned him out inside. After a hot shower we went out to the bedroom.

"On your knees Gerry on the bed."

Gerry was going to be in a world of hurt shortly, but this was what he wanted. Being so small, I knew it would almost be Rape as far as he was concerned. Add to that, that I could be very aggressive when I screwed someone would only add to his misery. I grabbed the tube of super lube and climbed on the bed behind him. His pure white ass was stuck up in the air.

I very much doubted I could get all nine inches of my cock into his short canal, but I also knew before the night was over he would have all my cock in him and he'd have several of my loads in his colon. I just hoped I didn't ripe him open.

Gerry was kneeling with his head in a pillow. I lubed up his hole and even squirted lube inside. He moaned when I did that. It would be a scream shortly. After lubing up my cock I applied a little pressure on his hole. I was surprised when the head of my cock just popped inside him. He gave a little yelp when it happened.

Grabbing a hold of his narrow hips I just rammed my cock in his hole. The banshee scream of pain from him was no surprise. While still pushing I rammed his head into the pillow.

I then backed a little before going in again. Each time my cock went in a little bit more. It was actually hard work. I stopped once while out and shot more lube on my cock. The next time I pushed in my cock went six full inches into him before I hit the end of his canal. His screams just on and on, up and down the scales.

"I'm in as far as I can get for now Gerry."

"Please take it out. It hurts so much."

"Too late for that Gerry. This is what you wanted."

I just stayed in place to give him time to get used to my cock inside his tight hole. I could feel his insides contracting and then tightening and I figured he was trying to eject my cock. His grunts, made the muscles of his entrance loosen a little. It would make it easier.

The movements inside his ass were doing other things to and I was getting close to cumming. I wanted to fuck him a few strokes before I came the first time so I slowly pulled back. I checked my cock. No blood, was good.

I made three deep hard thrusts to his continued screaming before my balls let go inside him. He stopped screaming when I came and just groaned. I think he thought that now that I had come it was over. How wrong was he.

Now slicked with my first load I just started to hammer his hole. I made about 10 or 15 thrusts before I pulled out completely. I flipped him on his back.

His face was covered in tears from his crying. I didn't wait though just lifted his legs to my shoulders. I saw the red puffy lips around his hole, lined up and rammed back inside him. His back arched and he howled at my assault on his tender hole.

Bent almost double I just hammered into him. I didn't slow even as my second load shot into him. He screamed real loud once and I felt my balls hitting his ass cheeks. My cock had finally found its way into his upper bowel. Now I could really fuck him. Soon the only sound was his yelps as my cock hit the top of his ass and my balls slapping his ass. My third load ended it as I immediately went soft. I slowly pulled out to audible pop as I exited his ass. That was followed by a gush of my spent cumm.

I looked at my cock as I let his legs down. All I saw was cumm with a few very small bits of blood. That was to be expected.

"Sit up boy and clean my cock."

He didn't move for perhaps a minute and then slowly crawled around. He wouldn't look my in the eye. He licked my cock clean and then sat back. A grimace crossed his face.

"Well Gerry, is that what you wanted?"

"Yes sir, but I don't think I'll ever get used to you."

"Oh yes you will."

I pulled him into the bathroom and cleaned him out. Then we went out to bed. I'm not sure how much Gerry slept, but I had a great night sleep.

In the morning he seemed to back to his regular self. He also appeared happy. After breakfast we sat with him almost on my lap as we finished our coffee.

"Are you okay Gerry?"

"Yes Sir. It really hurt and I thought I was going to die, but I'm okay now. You can do it anytime Sir."

"Gerry, I am going to be doing it anytime or anywhere I feel like it. Even outside with all the others watching. For all intents and purposes, until I say otherwise you are my boy to satisfy my needs."

"I knew that already Sir. I don't mind."

"You are a very strange boy Gerry."

I don't think I am Sir. I saw you looking at me in the mess hall the first day and hoped you would pick me. One of the guards in Sacramento told me if I got on your good side my stay would be better. So I just did everything you wanted Sir."

His slight movements while in my lap were doing there usual thing, I was getting hard.

"You know what you are doing sitting on my lap Gerry. You are going to have to take care of it now."

He just smiled and stood up. He undid my shorts and I lifted up as he pulled them down. He looked at my hard cock.

"Do you want me to suck you sir or do you want to fuck me?"

"That Gerry is up to you, but you remember what I said about sucking me. It's all or nothing."

"Well I know I can't get all of you in my mouth. I wish sometimes there were other bigger cocks I could suck to get used to big ones."

"That can be arranged Gerry."

He nodded and climbed on my lap again. This time with one leg on each side. He lifted up, pulled down my cock and sat down on it. He gritted his teeth and I saw tears stream from his eyes as my dry cock was forced into his hole. Once he was totally seated he just stopped.

"That feels good now Sir."

I slowly stood with him impaled on my cock and carried him to one of the couches. I lay down with him under me. I just started to fuck him. As I watched his face he got a dreamy look and his eyes seemed to roll back. Even before I made three strokes I could feel his hips pushing up to meet my thrusts. This kid may not have had real big cocks in him, but his ass was definitely experienced. I could feel the internal muscles holding gripping my cock on each stroke. It made me come up real fast. I think I only made twenty strokes before I erupted inside him. His deep moan of pure pleasure told me he was one very contented boy.

He quickly sucked me clean and then ran for the bathroom to clean himself out.

He padded back in and sat down beside me.

"Thank you Sir."

"No Son. Thank you."

The rest of the day was pretty quiet. I did fuck him twice and he tried to suck me off. He was very sore and crying a little as instead of just letting him try to take more of me I used both hands to force him to take more. He did get me off and swallowed everything, but was not happy.

He definitely needed more practice sucking bigger cocks. That, like I said could be arranged. I fucked him once before sleep.

After morning ablutions I gave Gerry a pair of shorts and t-shirt, along with his runners, that was all he would wear when he accompanied on my rounds. By giving him clothes, he would make many boys jealous of his new position. He knew what I was doing and was not happy.

After breakfast I started my tour. I did one in the morning and one in the afternoon. It usually took just over an hour.

Sixty five boys had volunteered to work. Six were sent to help in the kitchen. Fifteen were assigned to wash and clean floors. Including all cells.

The rest were sent outside to work at clearing brush and trees for any expansion that might happen.

Only those working outside were given clothes. They comprised of a one piece coverall in bright orange. Work boots, socks, Safety glasses, gloves and a yellow hardhat.

The coveralls were unique to this institution. Because this was classified as a minimum security prison, the coveralls, gloves and socks were completely bio-degradable. After just sixteen hours exposed to outside air they began to breakdown, becoming nothing more than dust in less than twenty four hours. Anyone running would end up nude, but for boots, hardhat and glasses. This was explained to them before they were allowed outside to work.

However even knowing what would happen to their clothes did not stop one of the Native boys and one of the Negro boys from running. It was not noticed by the guards until lunch break, but was noticed by the Computer when they went outside the perimeter. I notified the RCMP that I had two runners. They said they would watch for them and I gave them their transponder codes. Now the RCMP could track their movements. I just forgot about them. No longer part of my population of boys, they passed out of my jurisdiction. I did ask for pictures of their eventual execution. Those would be posted in every cell as a reminder of what happens when you escape.

Only a few boys made comments about Gerry wearing clothes and some even said he was the smart one to have the Warden as his keeper. It dawned on me that these boys would do almost anything to have what Gerry now had. That would make things so much easier for me.

I met my senior NCO Sgt/Major Calling sitting on one of the Gators we had. A young blonde boy sat next to him. He too had a t-shirt and shorts on.

"Everything okay Sgt/Major?"

"Fine Sir. I would like to come up this afternoon and talk about one of our more distinguished guests." He laughed.

"No problem. Come up after lunch today."

Gerry and I just wandered watching the work. About lunch we headed back to my quarters. Gerry quickly stripped. After lunch, I told him I would screw him after our meeting with the SGT/Major.

"Okay Sir." He smiled.

The Sgt/Major arrived on time with six hard copy files in his hands. I offered him a drink and Gerry mixed us one. The Sgt/Major never commented that Gerry was nude and in our meeting.

"Sir we have six high profile inmates. Two are the Son's of Senators. Three are sons of high department fathers. One is the Son of the Russian Ambassador." "How the hell did he end up here? I thought diplomatic personal had diplomatic immunity."

They normally do as long as they are inside the twenty five mile radius from their Embassy. Olof was not."

"Ottawa International was closed when he arrived in country. His plane was diverted to Montreal. He was put in the Diplomatic Lounge and told to wait for transportation. He didn't wait."

"He left the lounge, walked outside and stole a car that was idling at the entrance. He then headed for Ottawa. He ran low on fuel so stopped at service station and filled the car. Then went inside and grabbed some food. When he tried to leave the attendant stopped him so he just beat the guy to a pulp and then left. The QPP caught up to him about 30 minutes later. He screamed Diplomatic Immunity. The QPP ignored him and charged him with theft over 5,000 dollars, robbery with intent and assault. All Class two offences. He was looking at ten year when the Foreign Affairs stepped in."

"He got one year in a minimum security institution. We got him."

"Shit and now I suppose he's trying to use his immunity in here?"

"That's it in a nut shell. All the other inmates hate him. He won't do a damn thing and won't even shower. When one inmate told him he was nothing but a pig, he tried to beat the kid up, but was stopped when all the others stepped in. He's already got six demerits. One more and he's in the tank."

I keyed my intercom and ordered Olof brought to my office.

"In cuffs and drag him you have to."

"Time to cut this boy down a peg or two." "Sir, I know it is an unusual request, but is there any way to extend a boys jail term?"

"I take it you have someone in mind Sgt/Major."

"Yes Sir."

"Well under the contract ISSI has with all three Governments, ISSI can without any court order extend a prisoners sentence if they deem that prisoner to be a threat to society. However once a boy reaches eighteen his records are expunged and he is considered a free citizen and can't be held. At that point the only way he could remain with you is if you married him."

"Thank you Sir. I'll let you know."

When I looked at Gerry he had a big smile on his face. I was pretty sure what he was thinking.

The two guards brought in the struggling Olof and they had a hard time controlling him. Once he was standing in front of me a string of what I figured were Russian swear words spewed from his mouth. I let him rant for a while, then got up and walked up to him and slapped him across the face. That stopped his yelling and he just stood.

Olof was a very well muscled young man, overly so I thought. I figured he had been using illegal muscle enhancement drugs and from the size of his balls and cock made it even more probable. He had a wild look in his eyes, almost inhuman look. I think those drugs plus his visions of grandeur as the Ambassadors Son might have unhinged him.

"You can not hold me and I will not cooperate with you. What you do is illegal. I have immunity."

"I don't plan on holding you. I'm going to ship you to the maximum security insane asylum in Yuma. They can decide what to do with you."

"Sgt/Major put him in isolation until the next supply run."

"Yes Sir."

The two guards dragged a screaming Olof from my office.

"He's bonkers." Gerry said.

"Yeah he is. That means I don't need him here."

"Is there anything else Sgt/Major?"

"You might want to talk to Stanton. He's the Son of Senator Stanton of Mississippi. He was convicted of attempted rape of a fourteen year old boy. He is another that believes he is to good to be in here. He got two years less a day."

"Very well I'll do that now."

"Later Gerry." I said as I saw the smile leave his face.

I ordered Stanton to my office. I told Gerry to make me another drink. When he brought I pulled him close and gave him a peck on the cheek.

"Gerry we have two years to enjoy each other."

"Could it be longer Sir?"

"We'll see Gerry. You might find someone else here you like better."

"I'll never love anyone like I do you Sir."

That was the first time he said he loved me. I wasn't sure if it was lust or love I felt for him, but had lots of time to explore that part.

When Stanton was shown into my office, I heard Gerry's quick intake of breathe. He was one hot looking boy. Almost a miniature David. At 5 foot 6 inches he was proportioned perfectly. He was very well toned but not overly so. Blonde hair and blues eyes. He had a five inch fairly thick cock and low hanging balls. It looked like he might have either shaved or trimmed his pubes before.

He stood with his hands at his side almost posing for me.

"Do you consider yourself Straight, Bi-sexual or Gay Stanton?"

"I'm straight Sir."

"Really! You were convicted of sexual assault of a fourteen year old boy. That sounds very Gay to me."

"I didn't really assault him Sir. He asked to suck my dick."

"Did you fuck him too Stanton?"

"Well I had before, but he had had lots of guys and wanted me to. He was just sucking me when we got caught."

"So you say you are straight and yet you fuck boys up their ass and they suck your dick too. Every returned the favor Stanton?"

"I'm not gay Sir."

"Well you like to screw guys and have them suck you. That sounds very gay to me. Have you ever had a girl Stanton?"

"No Sir." "Stanton a little cooperation in here goes a long way to make your time here better. You don't have much choice in how long you are here. That was decided by the courts. If it wasn't for your Father, you would be in a Class 2 facility. Saying your straight in one of those would not have stopped several inmates from screwing your butt."

Wonder of wonders. When I said he would have been raped in a Class 2 institution he started to get hard. Maybe that's what he was after.

I looked at Gerry. He had his hands covering his crotch. I figured he was hard.

"Sir, it's not that I don't want to cooperate, but all the guys just want to play around at night. I got no privacy and can't do anything with someone watching. I want to get along."

His cock was almost erect as he talked. I figured he had a good seven inches of thick meat.

"Gerry."

"Yes Sir."

"Go suck Stanton off."

"YES SIR!" He bounded over to Stanton, went to his knees and had Stanton's cock in his mouth immediately. Stanton was so shocked he just stood for a minute and then I figured the feelings took over. He put his hand on Gerry's head and slowly fucked his face.

I heard Gerry gag a few times but did a good job. Stanton came pretty quick. He almost fell down when Gerry sat back.

"You taste good." Gerry said.

Gerry went back to the chair he had been sitting in.

"Did you enjoy that Stanton?"

"Yes Sir."

"Now, do you want more privacy Stanton? With just the touch of a button your walls will be opaque and there will even be a door on your cell you can lock."

"What do I have to do to get that Sir?"

"Go over and suck off Gerry."

Now I would see. If he really wanted it he would do it. Also after sucking Gerry there would be no way back for him. Eventually I knew I was going to screw him too.

The young man looked at Gerry. Then he looked at me. He got a resigned look in his eyes, then just walked over and kneeled in front of Gerry. I heard Gerry talking quietly but just ignored them. I did notice Stanton's very nice ass and would have loved to ran my dick into him right then and there. Gerry was definitely going to get fucked as soon as Stanton left.

I watched as young Stanton sucked off Gerry. I heard him gag and Gerry say 'just swallow it' and knew Stanton had just sucked off his first cock.

He stood up and I saw him lick his lips.

"Well, how was it boy?"

"It was okay I guess Sir."

"That is called cooperation. You did as I asked and now I will do as I said. You can tell your cell block guard you are now a level 2 inmate. That will give you full privacy to do as you wish in your cell."

"Thank you Sir."

"I want to see you here in my office at 1400 tomorrow. You can tell the guard the same thing."

"Yes Sir."

"You can leave now."

Stanton left and as soon as he was gone I had Gerry on his back reaming his ass.

TBC.