The Prisoner and His Guard
So let me tell you how I, Dylan Scott, fucked up my life when I was only thirty-two years young.
I had it all: a great, but very stressful job; two terrific twin sons, Kevin and Karl, aged six; a spacious suburban home; and a beautiful wife. She was a bit of a nag, so that would be the only flaw in my perfect life. No matter how much money I made, it was not enough for her.
I have an MBA, and I was the CEO of a publicly listed company. At my age that was a miraculous achievement. I had to commute daily from the suburbs to my office. It was an hour on the railroad, but well worth it.
My next door neighbor, Ben Holliman, commuted with me. Ben was a stock broker and financial advisor. When we reached Manhattan, he took a subway downtown to the financial district, and I walked to my midtown office. Occasionally, we were lucky enough to be on the same commuter train going home. As you can imagine we became really good friends.
Ben's life paralleled mine. Like me, he had it all. The difference was that he was two years older than I, and had three young children. He even confided in me that his wife was a royal pain in the ass, always hounding him about one thing or another. It seemed he could never satisfy her, in or out of bed. I confessed to the same problem.
I trusted him with all my investments, and he was my stockbroker. His investment philosophy---for men as young as we were---was to be very aggressive. As a result he was making me lots and lots of money. I never questioned his buys and sells, and therein lay my mistake. Sometimes he had me sign a paper consenting to a buy or sell transaction, and other times, he didn't. I should have wondered about that, but I trusted him completely.
One fine morning, he and I, along with several others, were arrested for insider trading. Ben received ten years, but his clients got two years each. The judge bought our defense that we had left it all up to him, and we were innocent victims. He would have released us with a fine, but we had all signed a document approving the transactions, and so he was required to mete out some punishment.
My wife immediately started divorce proceedings, and she requested sole custody of the kids, and most of my assets. Since I was a felon, her request for sole custody was granted. Upon my release from prison, I would have to begin paying alimony and child support.
Fortunately, Ben and I went to different prisons, or I might well have killed him. I went to a minimum security facility, and he went to a maximum security facility. He had committed a white-collar crime, and as much as I hated him, I thought that maximum security was a bit of a stretch.
I arrived at the prison with one other `guest.' I was shaking in my boots and resisting the urge to shit in my pants. The bus driver handed us over to a very husky looking guard. The guard told us that his name was Joe Garcia, and our first stop was to the supply room, where we were issued our prison garb. From there he took us to our cells. I was delighted to learn that there was only one inmate per cell. The other guy was assigned to a cell directly across the passageway from me.
Joe told us to leave our civilian clothes in the cell and come with him. He dropped the other guy off at the prison laundry, and introduced him to the prisoner in charge. Apparently he had been assigned to prison laundry duty. Next he took me to the commissary and introduced me to the lead prisoner. It appeared that I had been assigned there. My "boss" did not appear to be too threatening and I relaxed some. He told me that my duties would be to assist the cooks, serve the chow line, and clean up afterwards. Cleaning up included both the kitchen and the commissary.
When we were finished with our duties, and had eaten our own meals, my fellow cafeteria workers and I, along with the rest of the inmates, had two hours to play cards or pool, watch TV, or just sit and read. At 9 PM, a bell rang, reminding me of my high school days. That was the signal to return to our cells. After we were all inside, the grille gates closed and locked automatically.
The cell was quite civilized. The mattress on the cot was nice and thick. I had a dresser with a mirror, a commode, a chair, and a sink. The first thing I did was take a leak. Then I undressed down to my boxers. It was way earlier than my usual bedtime, but I reckoned that we would be awakened way earlier than my usual wake up time, as well.
During the "social hour," I picked up a newspaper in the library. I settled down to read it, and much to my surprise, I heard a deep sexy voice call my name. I was startled. I looked up to see a prison guard standing outside my cell. He was holding a clip board, and I assumed that it was his roster. What happened next confused the shit out of me.
The guard put his hand through the bars of my cell. "Hello," he said, "my name is Sam Wright. I'm the night guard. If you have any problems, just push that red button." He pointed to the button, which I hadn't noticed it before. "Also Dylan," he continued, "I want you to know that I read about your case in the newspapers, and I don't personally believe you should be here. I'll try to make your stay as stress free as I can."
I was grateful for that. I reached out to return his handshake, and I looked at him. He was well over six feet. His hair was a sandy blond, and his eyes were brown. He was very muscular. I worked out regularly (used to) and I had a good body, but I envied his. He seemed reluctant to let go of my hand, but eventually he did, and he disappeared to go do whatever it was he did all night.
After he left, I read for a while longer. I shut my lamp and attempted to sleep, but it was much too early for me. I grew restless in bed and I began to worry. I was eligible for parole in thirteen months, but whether I was released in thirteen months or two years, I would be an ex con. Would anybody hire me? I suddenly felt very sorry for myself, so I got up and began to pace my cell. I figured I could use the exercise. Once again I was startled by Ben's voice.
"Can't sleep?" he asked. "Everyone has trouble sleeping at the beginning. You'll sleep better when you get settled in."
"On the outside," I answered him, "I don't go to sleep until midnight. I'll have to get used to lights out at nine."
"Until that happens, would you like to play some cards with me? It gets pretty quiet here at night."
"I'd like that," I answered immediately.
He took his keys out and opened my gate. "Do you play gin rummy?" he asked.
"Of course," I replied.
I relit my lamp, and we sat down on my bed. He took a deck of cards out of his hip pocket. He told me that he made rounds every two hours, and if I wanted to, he would like to play with me every evening during his first break. Stupid me, I never picked up on his innuendo.
During the game, I admitted that I was very pleased that there was only one prisoner per cell. "I appreciate my privacy," I said.
Sam started to laugh and slapped my knee. "You'll appreciate it more when some of these guys come on to you. This is a minimum security prison, and I've never heard of anyone getting raped, but I know for a fact that there's a lot of consensual gay sex going on. Even straight guys, who have reached the limits of horniness, will join in the action." All the while he told me this, his hand remained on my knee.
"I'll whack off before I'd do that," I stated a little too loudly and adamantly.
"That'll do you for a while, but believe me, one day you'll want a warm loving body lying next to you." Sam's hand had never left my knee, and it seemed to have moved up my thigh a few inches. He finally removed it, when he had to deal a new hand.
After he left, I finally crawled into bed, attempting to get some sleep. That's when it finally dawned on my thick brain that Sam was hinting that he wanted to have sex with me, but only if it was consensual. I knew I should have been revolted, but it struck me that it wouldn't hurt to have this handsome guard looking out for my welfare. Another reason I wasn't revolted is that I had a few gay sexual encounters in college. I never thought for one minute that I might be gay, but the sex was very enjoyable.
I couldn't concentrate on my duties the next day. All that was on my mind was Sam's hints and innuendoes. I thought that when we played gin rummy this evening, I would subtly let him know that I was interested. Then I began to shiver.
What if I was misreading his attempt to be friendly? What if it was just that, and not a come on? He might hate me, and he could make my life hell. I decided to go very slowly, and pretend I didn't notice his advances.
When he came into my cell that evening, I almost ran to embrace him, but I controlled myself. Instead I used a different ploy. The previous evening I was wearing my boxer shorts, when he came into my cell. The fly clasp was securely snapped in place. This evening, I made sure that the clasp was unsecured. When we sat down on my bed, my boxers would gap, and Sam was sure to get a glimpse of my pubes, if not a little bit of my cock. My pubes are trimmed and my cock is four and a half inches when flaccid, and seven and a half inches when hard. It is uncut and very wide around. The rest of me is worth bragging about also. I am 6'2" tall, and I have a great body. My hair and my eyes are both brown.
When he entered my cell, he handed me two new decks of cards. "Keep them here," he said. "That way I don't have to carry them with me all the time."
"Does that mean that this is going to be a regular game?" I asked.
"You betcha," he answered.
I decided to act on my impulses and I got a little bit bold. "Sam," I asked, "why are you being so nice to me?"
"I'll tell you," he said. "If we were sitting in my living room, I'd never admit what I am about to tell you. You'd pick yourself up and run away. It's different here. You're a captive audience, so to speak."
I knew what he was going to say, so I smiled at him as a way of encouraging him. "Are you ever going to come to the point?" I asked.
"Yes, I have a confession to make. I'm gay. For your information, I'm out of the closet everywhere except at work. I think you can figure out why. The minute I laid eyes on you, I lost my heart. You look exactly like the man of my dreams. You told me that you would jack off before you would have gay sex. I swear I'll never come on to you, but I will come by every day to visit with you. Who knows? Maybe someday you'll have a change of heart. If you do, or when you do, I promise to take you to paradise."
I was so overwhelmed that I reached into him and gave him a chaste kiss on his lips. His smile threatened to break his jaw.
"This is all new to me," I lied. "Let me think about it."
"Once again let me make it perfectly clear," he said. "I promise to take you to paradise."
After Sam left, I turned off my light and tried to sleep. I tossed and turned for quite a while before I finally fell asleep. I have no idea what time it was when I woke up, but for sure, it was the middle of the night, I had been dreaming that somebody was giving me a blow job. My wife never did that, but I knew how it felt from my few college encounters. While I was in the twilight zone, I remember thinking how wonderful it felt. When I awoke completely, I was aware that my boxers had been pulled down, and a real live human being was down on me. I was certain that I knew who it was, but I whispered in the dark, "Sam is that you?"
Sam stopped his labors and slid up to me. That was when it happened. He kissed me. He forced my lips apart with his tongue, and our lips began to tickle each other. As our lips and tongues continued to copulate, it struck me like a thunderbolt. I was in love with Sam. I could only wonder if I had been gay all my life. For sure this was the first time since I met my wife that I was enjoying having sex. How could that be? The answer came to me very quickly. Sam wasn't having sex with me. He was making love with me.
It was a tight fit, but the two of us could lie facing each other on my bed. "Please," I begged, "lower your trousers. You can't have all the fun."
I heard a sigh come from his lips. "I knew it," he said. "I knew you felt the same way I did."
He turned around until he was in a sixty-nine position, and he took me into him once again. I screwed up my courage, and I took his cock into me. Why had I ever hesitated or been grossed out by fellatio? Sam tasted like freshly baked cinnamon rolls to me. We got each other off rather quickly and we both swallowed everything, so there was no mess.
Sam slipped out of bed and got dressed. I put on my boxers. He kissed me and said, "I'll see you tomorrow." This time, happy and content, I fell asleep immediately.
For six months Sam continued to visit me after lights out. On our second night together, he brought condoms and lube with him and he taught me how to fuck. To this day I haven't decided if I prefer fucking or getting fucked. I decided to remain versatile, and Sam feels the same way.
One day, he asked what my plans were after I got out. I told him that I had no plans other than to get a job. "I'll try to help you," he said, and I kissed him hard.
We were served a very traditional meal for Thanksgiving. After my crew cleaned up, we joined our fellow inmates in the auditorium. The warden said a little prayer of thanksgiving, and then gave us wonderful news.
"This facility is minimum security. Therefore, those of you wish to do so, can go home for three days at Christmas. But be warned," he said, wagging his finger, "if you fail to return from your furlough, you will be hunted down, arrested, and sent to a maximum security prison. Your sentence will be doubled, and it will start anew."
I learned later on that a little less than half the residents chose not to leave the prison. I supposed that, like me, they had no home to go to. That night Sam asked me if I was going to accept the furlough, and I said that I had no place to go. He got really excited.
"Please," he said, "I have the week off. Spend Christmas with me." He winked at me, and added, "We'll be able to make as much noise as we want to."
Sam had a one bedroom apartment in town, about a fifteen minute drive from the prison. It was small, neat, and clean. When we walked into the apartment, we fell into each other's arms. I actually started to strip, but Sam stopped me.
"I need to talk to you," he said. "I may have a job for you, but it's way beneath your education and your talents. Would you be interested? We can live here together. I'd like that."
I was afraid that nobody would hire me, so I was more than interested. "Tell me more," I begged.
"I have this friend," he said. "He and I went all through school together, and we remained friends even after I told him I was gay. To prove that he didn't care, he asked me to be the best man at his wedding. He owns the only taxi service in this small town. His dispatcher is getting married and is moving to the west coast in June. He's looking for her replacement. I told him about you, and he said he would be glad to train you."
"Next June," I repeated. "I'll be out by then. The whole idea of living here in this pretty little town, and living with you, is just too good to be true. I'd love to relocate. I'm not allowed to see my boys, so I have no reason to go back to New York."
"I prayed that you would say that," Sam said. He grabbed me in a bear hug. "We'll go to his office tomorrow and I'll introduce you. If you don't mind, I'd like to go to Christmas Eve services tomorrow evening. I want to thank God for you."
I smiled and said the same thing.
That night, for the first time, we made love without any restrictions or constraints. We undressed fully and showered together. What bliss. There was not a spot on my body that Sam didn't kiss, and I did the same to him. We had always made love in the dark, but now I could get a good look at him. His cock was about the same length and width as mine, but he was cut.
We agreed to play sixty-nine, but tried to refrain from cumming. When we were both worked up to a frenzy we fucked each other, but no more condoms, just lots of lube.
That night I found out why Sam was delighted that we could now make all the noise we wanted to. He was the noisiest lover I ever heard. When he came, his wailing scared me to death. He actually encouraged me to be noisier. He wanted evidence of how much I loved him. I was happy to oblige him.
I had about a month off between my release and the day I started my new job. I got a lawyer, and he was able to get my alimony and child support reduced to be commensurate with my new salary. This angered my ex-wife, and she wouldn't allow me to see my sons. She actually got a restraining order against me. I determined that I would seek them out on their eighteenth birthday. I wanted them to know that I loved them, and it was their mother who kept me away from them.
She should have expected this. She took all my assets in the divorce, so she knew I had nothing to give her. She should have been smart enough to know that as an ex-con I could never get as good a job as I had. I didn't feel sorry for her in the least.
I loved my new job. Compared to my former career job, the stress was minimal. My union with Sam was also stress free, so different than my life with my ex. And did I mention that the sex was infinitely more satisfying?
I told you that I hated Ben Holliman for what he did to me. Well, I no longer hate him. In fact, I am grateful to him. He forced me to abandon a lifetime of stress, which may certainly have killed me. Now I live with the greatest guy in the world, and he kept his promise. He took me to paradise.