This story is a work of fiction and contains descriptions of explicit sexual acts between two consenting adult males. If this type of content offends you or you are under the age of 18 do not read it.
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You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored.
White Boy in Prison
By
Wolf
This story started a little over thirty years ago. I grew up knowing there was something different about me I just didn't know what. I was a late bloomer and didn't lose my virginity until I was twenty-years-old. I had started drinking a lot to help me feel more comfortable around people. I finally got a girlfriend my age.
One of the older women I had been having sex with wouldn't stop coming over to my house. She used to spike her husband's drink with the drug xanax so we could fuck. She told me: "They only had sex about once a year and he only had a 3-inch-dick.
He woke up one night and I don't know for sure how long he had been watching. I was doing a pretty good job of making it last as long as possible before cumming in her cunt, before I noticed him. It was dark but my eyes adjusted enough to see him just standing there watching. I stopped moving and she started yelling at me to keep going. I didn't move and just started shooting my load into her. He turned the lights on and I scrambled for my clothes and went out the front door and dressed on the way to my car.
I have a decent sized dick at about 7.5-inches but don't last long normally. So, most of the time she'd get mad at me for not lasting and then straddle my face and I'd eat her pussy. When she got close to cumming she would fuck my face. She would jam her large hairy cunt into, my chin or nose or between her sweaty ass cheeks. When she finished my face was covered with a mix of my-cum and her pussy juice.
I tried to tell her I had a girlfriend now but that didn't matter. She told me shut the fuck up, and strip! I could eat her pussy if I couldn't get it up.
When I was 22-years-old I wrecked while drunk and ended up with a 3-year prison sentence. The first few months went just about how I'd expect. Two-man cells and only left the cells for meals, We had one hour in the yard a day with showers twice a week. It wasn't that bad but I had to use a stainless-steel toilet in the cell except for the smell. The group showers and regular strip searches were the worst part. It still felt safe as there was always a guard nearby. I let my hair grow long and some facial hair. I thought if I looked kind of rough people would leave me alone. I was about 5'11 and only 125 pounds so not really capable of defending myself.
Then I got transferred to another prison where I would spend the bulk of my time incarceration. A nice minimum-security prison where inmates had their own key to their rooms. No more toilets in the cells and you can go shower whenever you want. You could walk around all day as long as in the cell for counts and after 9:00pm until breakfast call.
I got to my room right at lunch time. The bus ride there made me miss lunch, so they gave me a sack lunch. I wore an orange jumpsuit when I arrived, but learned that my family could send me regular clothes but that would take a couple of months. The room was empty and I wondered what my cellmate or cellie was like. He worked the morning shift in the kitchen and showed up a short time later. His name was Ken, he was married with a couple of kids. He was an older black guy I'd guess he was in his early forties which seemed old to me at the time. I didn't think I was a racist, but I had grown up in a rural neighborhood that was a white community. I had never interacted with any black people before. I wondered if we'd get along with each other.
He was well built and kept his head shaved. I had the top bunk and stayed up there as he introduced himself and he started taking off his work clothes. Even though I had gotten somewhat used to nudity it still seemed odd how normal he was with just getting naked as if it was nothing. He had been in prison now for 5-years with 2 more left to serve. His dick was soft but pretty good sized. His balls were most noticeable. He put on a robe and grabbed a towel and said after he showered, he'd give me a tour.
When he returned, he took off his robe and touched up shaving his head. There was a nearly full-length mirror built into the cell wall. So, I was looking at his butt facing me and seeing the reflection of the front side inv the mirror. I tried not to stare, but he was talking to me so I felt I should look at him while he did so. He'd turn to talk directly from time to time and it was hard not to look at his dick flopping side to side as he turned. It had shades of purple and pink near the head. Very short wiry pubic hair like steel wool.
While I had always told myself I wasn't gay. I knew growing up with older brothers with larger dicks I liked to see them. If one of my brothers asked if anyone was awake, I'd be quiet as I knew they were going to jackoff and I liked to watch. I hadn't jacked off or had sex in nearly four months and was worried I was going to get a hard on while looking at Ken's cock. With just a jumpsuit and no underwear it would not be good.
He got dressed and called me down, he said the sack lunch I had was pretty-small. He had snacks stored up from the commissary and gave me some. He also had real cigarettes which everyone called tailors, while I had been rolling tobacco since I got in as the price was far cheaper. We went out for a smoke. He said: "I looked like a scrub!" Which was a term I hadn't heard before.
He said: "I'll check out the barber equipment and give you a good haircut. People would respect you. He seemed like he knew what he was talking about and I trusted him and met him back in the bathroom. He had me strip and sit on a stool while he started cutting my hair. I kept my hands over my privates hoping I wouldn't get aroused. When he finished, he had me stand up and finish shaving my face. He had kept the hair long and just styled better.
He asked: "Do you like it?"
I hesitated because it looked like a girl's haircut.
He sensed this and told me: "Lots of guys have haircuts like yours and you have such nice hair a lot of guys would kill for it!"
I felt embarrassed about the compliment but figured he knew a lot more than I did so I trusted him. Then he had me get into the shower and he used a high-quality shampoo on my head, (I didn't think at the time but wondered later why he had fancy shampoo when he had no hair.)
He just stood at the stall door which was about waist high and watched me. He joked and asked if my ass had ever seen the sun. Then he said: "With a peach of an ass like yours, lots of guys are going to go after it!"
That freaked me out and as I got out and started drying off, I said: "I thought this was a safe place!"
He said: "It's not as if there are no guards around. They're not as many as in the higher security prisons. I then noticed that I hadn't seen a guard since my strip search when getting off the bus. In the prison I had just come from there was always a guard nearby.
He told me: "Not to worry I wouldn't let anyone mess with my cellie."
I felt a little relieved. He had a robe for me, but said: "With hair like mine, if I did this after every shower your hair would be even better. I want you to bend over and let your hair hang down and brush from the back of the neck down 100 times."
That was awkward with him behind me with my bare ass up in the air as I started brushing. He put his hand on my lower back to help steady me. He said: "When I'm not here with you, you should wait to do this in the room or someone's going to take your peach."
I felt some fear again and hurried through the hair brushing. When I got to 100, he slapped me on the butt. I got worried as this seemed to cross a line but he just laughed. I thought maybe it was just like baseball players who slap each- others butts often and that's not gay.
Back at our room he offered me a pair of sweat pants and t-shirt, so I wouldn't have to stand out as a newbie waiting for my clothes. He said his underwear was too big for me but it was still better than the orange jumpsuit without underwear. After I changed, he told me to turn around and he stuck his fingers into a hole in the butt of the sweats, far enough in to touch between my cheeks. I jumped away and turned and blushed. He said he just wanted me to know there was a small hole in the back so I'd be careful no one took advantage of me in the hallway. He seemed to keep telling me things that scared me and didn't calm me down.
Now we headed back outside and met with a group of his friends. Ken pulled out a joint and lit it up and passed it around. I could not believe thast I was smoking pot. Ken made a comment about needing to put some weight on my ass and gave me a hard smack and everyone started laughing. I was stoned by that time and started laughing as well. The rest of the day went great. But Ken was always real close and putting his hand on me which I wasn't used to but there was something about him that just made me trust him. He deep voiced baritone that sends vibrations through you.
After 9:00pm time to stay in the room unless using the bathroom. Ken pulled out a partial joint and got on a metal desk built into the wall. There was a vent and if you took a hit and exhaled into there you wouldn't smoke up the room and get caught. I went up next and he held onto my leg to help me while I took a hit. I was ready by then to climb up into my bunk.
Ken said: "I want to show you something!" He pulled out a deck of cards That had photographs of naked women performing sex on each other on the face of the cards. I was like 'WOW' this is cool! He told me to flip through some and he was right behind me commenting on the girls. I felt kind of awkward and tried to hand them back to him but he told me to keep going. There were some great ones. So, I did and I moved forward as it felt odd as he was right up against me. He just followed when I moved and there was only so far, I could move. I got to a good one that he liked and he took a hold of my hips and thrust against me. I dropped the cards and moved away and turned and he had his dick out. I couldn't speak and he moved closer to me and asked what the problem was. I couldn't speak and stuttered a little bit.
He pointed at his dick and asked: "Are you going to leave me hanging like this?"
I would guess that his cut black cock was about 9.5-inches. I finally said: "I'm not gay!" and headed for the door.
He stopped me and said: "If you tell on me. I will get sent to a higher security prison and will lose my upcoming release that is about fifteen months away.
I said: "I just have to go to the bathroom."
He said: "If I get sent away, everyone would know it was your fault and they will see you as an open game."
I left for the bathroom and probably spent about twenty minutes there. That was the closest I had ever been to a hard dick and tried to get the image out of my mind. I decided to just go back to the room and go to bed. He seemed too nice to beat me up and rape me. Maybe if he started to try it a guard might come along and then I wouldn't be ratting on him.
When I came back into the room, he had his sweats back up and stood up so I couldn't just hop up on my bunk. He apologized and said: "I had misread you. but I thought that I had led me along."
Thinking back about the day maybe I had.
He said: "If you continue flipping through the cards some more, and let me rub against you then I'll still-keep others from bothering you! I will stop as soon as you say STOP!"
I agreed both for the protection and I really wanted to be friends with him. It's no real harm just flipping through cards and letting him rub against me. So, I picked up the cards and went back over by the desk and started slowly looking through the cards. I heard him pull his sweats down and push up against my butt. He said: "You've been teasing me with that peach all day!"
I thought maybe I had, but it wasn't on purpose. He was talking right against my ear, and I realized I had a raging hard-on. I told myself that I'm not gay, It's just a normal reaction to contact because it had been so long since my last release.
He put his fingers in the hole of my sweat pants and started playing with my butt. I started thinking now I should say stop this is more than I thought I agreed to. He then started pulling my sweats down but they were hooking on my hard-on. I didn't want him to know I was hard, so I helped them down and felt like I just messed up and gave him permission to go farther than I had agreed to. He started playing with my nipples with one hand and with the other hand he played with my hair. He started kissing my neck and ears. He turned my head and kissed me on the mouth. I tried to keep my mouth closed but he pinched my nipple causing my mouth to open and he pushed his tongue in. I felt wetness between my butt cheeks, I didn't know it was precum at the time and thought maybe I was sweating. Ken produced a good amount of precum and it was dripping down my butt crack. He moved his hand back to my butt and started pushing his finger in while kissing my ear and neck. I had never had so much stimulation that I was worried I was going to cum.
He told me: "Bend over and spread your cheeks." That was what the guards told you during a strip search. So, I was quick to do as told, instinctually. I thought this was it he's going to fuck me! I thought about saying stop or offering a hand-job or blowjob instead but I just couldn't speak. Instead, he knelt-down and started licking my butt. I almost fell over and let go of my butt and held onto the desk. He grabbed my butt cheeks and pulled them apart and started licking my asshole.
I had never felt anything like it. I also thought this can't be gay! As Ken is not gay, he's married with kids. I'm not gay either. He took my balls and pulled them back between my legs and started licking and sucking on them. I tried not to make any noises as it was embarrassing but that just made it worse when I did finally make a loud noise. I'm I think I even said: "Oh, Ken!"
He stood back up and I did, I realized with the window in the door if anyone walked by, they'd see what we are doing and I asked him to turn the lights off. He finished taking off his clothes before turning out the light. He returned and pulled my hand back to his dick. I just held on to it like it was a flashlight. It was a lot thicker than mine and felt hot. Then he pulled me towards his bed, he had a towel laid out. I figured that he had laid it out when I was in the bathroom. He must have been fairly-sure I would return and he would get me there. I didn't realize at the time but he had mineral oil he used to lube me and himself up. I felt his dick against my hole and it hurt a lot when he pushed in. My hand shot back to stop him and I said: "I can't do it, I'm not gay and it hurts like hell!"
The head was in my ass and he just stopped moving. He pulled my hand away and told me: "Calm down, it would get better. Push out!"
I thought he meant push against him. He said: "No, like you're taking a shit!"
I did and he pushed in a little further and repeated it until he told me that I had his whole dick in my ass now."
My dick was fully soft now and I thought that proves I'm not gay. I buried my face in his pillow to stop any noises I was making. He started slowly pulling out and I felt like I was shitting myself and instinct was to clamp down, but the stabbing pain made me stop that quickly. He liked the way that my sphincter had gripped his cock, and said that my ass was sucking on his dick. I didn't quite understand that. Then he started speeding up and I had to take my head off the pillow and push back or I'd be pushed into the wall.
I didn't think of it at the time but I'm sure anyone who was awake in our hall knew Ken was breaking in a new piece of ass. I'm not sure how long he took. It felt like 20 to 30 minutes until Ken's large balls emptied inside of me. I was numb from the waist down and didn't feel much, just that I could tell that my colon was a lot more lubed up now. I did feel warm fluid running down my inner thighs and it felt like blood as it was warm. I worried he had hurt me but it was just cum. He pulled out and turned the lights on. I could feel cool air going inside of me and warm cum running out of me. I was exhausted and just stayed there while Ken cleaned himself up and then he wiped me up. He slapped me on the butt and said he had to get to bed as he had to get up at 4:00am for work. I crawled out of his bed and could barely stand and I stopped and held onto the desk. More cum was running out of me. The whole room smelled of cum and sex.
I was back to full hard and grabbed my clothes and climbed up into bed. I turned to face the wall not wanting him to see my face. He asked me if that was my first time. Of course, I told him that it was and I'm not gay.
He said: "You're a natural and that my ass was made for his dick." He turned out the lights and went to bed.
I put two fingers in my asshole and it felt like a pussy. There was some of his cum on my balls and I tasted it and then started jacking off with it as lube. I had one of the best jackoff orgasms I had ever had. That was the beginning of me being a white queen for a black stud for the duration of my incarnation. After my parole and time passed, I became a true size queen for black cocks!
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@gmail.com
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