Some of the prisoners have even asked me for my panties. They love smelling my sex and masturbating. I’ve given a few of my used pairs out to my favorite guys. It keeps them coming back for more, and they usually fuck me really good after smelling my panties.
I know this is like teasing you, just giving you little glimpses at what takes place behind the walls of the prison. Don’t worry: I’ll share some of my favorite nights!
My first time: That’s right, I lost my virginity at the prison. It wasn’t really my choice that night, but I have to admit I wouldn’t change a thing about it.
I had just started the week before. I had yet to be touched by a soul. This night though, it would all change. I was only 22 at that time. I stood around 5’ 4” tall, and weighed 130 pounds. My body was toned from spending lots of time in the gym.
I was small, but not weak. I had to be somewhat strong, just in case problems broke out at work. Though all my training didn’t help this night. I was overwhelmed quickly.
One of the prisoners was especially missing female companionship that day, and he saw me. I have to admit if I was into girls, I would have been just as excited to see me!
So he grabbed me in his strong arms and laid a big kiss on me. Not just any kiss either, it was a soul-binding kiss. I could feel the passion in his tongue as he probed my mouth and sought a reaction from me. I couldn’t help myself and I was soon kissing him back with as much passion. My tongue tangled with his and I moaned loudly as he cupped one of my breasts through my uniform top.
I know I should have stopped him, but it felt far too good. Instead I moaned again and he proceeded to undo my top and pull my boob out of its holder.
He covered my nipple with his mouth and was soon suckling my breast as I moaned more and ran my hand through his dark hair. The tight curls of his afro excited me more. Seeing his dark skin against my pure whiteness made my pussy juices flow more.
I could smell myself and I knew he could too! His hands unbuckled my pants and soon he had pushed his big hand down my soaked panties.
I didn’t hesitate as he lowered my pants and undressed me. I wanted his hardness inside of me, and I wanted nothing more than that. He pulled his monster black snake out of his own pants.
I almost ran, seeing the hard 12 inches in front of me. But a huge part of me also wanted all that hot meat inside of me. I laid on his cot and he pushed his hardness into my opening.
To say I was wet would be an understatement. There was so much moisture that his cock slid to the side and he missed my pussy hole.
“Fuck me,” I moaned as he wrangled his cock to my opening once more and pushed forward. He didn’t take his time, just fucked me hard and fast. It hurt for a second, until he played with my clit and my body shook with an orgasm.
He pushed his huge blackness in and out of my hole as I writhed under him. My shrieks could be heard throughout the cell block. I could hear the other prisoners cheering him on through my own yelling.
A couple of my fellow guards came around the corner and stopped and watched for a moment. They weren’t worried about me; they could tell from my moving and moaning that I was completely enjoying being manhandled by this man.
Instead of help, I soon found another cock out and placed into my mouth. It stopped my moaning, but soon I was trying to suck this just as big white dick that was being thrust in and out of my mouth.
I was choking on the cock of my fellow guard Jim. Hell, I would never have known he was so huge. But I was loving it, every second. As Jim and the prisoner shared two of my holes all I could think about was how lucky I was to have to well-built men serving me their cocks on a platter.
As the black man continued to fuck me hard, I could feel my body head towards another orgasm. I moaned loudly as Jim’s cock jerked in my mouth and felt his warm sperm splash down my throat.
He pulled out his dick out of my mouth and sperm flowed out over my chin and onto my chest. He smiled at me and patted my head.
“Welcome to the prison, honey. I hope you don’t mind the sperm. I think you’re going to see plenty of it while you work here.”
I heard the black man moan and felt his dick as it spilled his seed deep inside of me. I didn’t mind; I was on the pill. Maybe it was foresight, but I was really happy about that choice in the past five years.
The black man helped me up and apologized for being so rough. “I didn’t know you’d never been fucked. Hell, you’re so damn hot I would figure for sure you’d had a dick in you before.”
“It’s okay, I liked it,” I admitted.
“Next time it won’t hurt so much,” he said.
“Oh, next time. I can’t wait for it.” I smiled at him.
By the way, his name is Matt, and he is part of another of my adventures in prison. This time it was my first gangbang. I took on four prisoners that night and got the fucking of my life!
This night came about four months after my first time with Matt and Jim. The guys knew by this time that I really loved sex and the taste of sperm.
They even had a competition to get to pick the first four to fuck me in this situation. I found out later that they often argued who would get to have sex with me on any night.
I felt very flattered by so many men wanting me. This helped my self-esteem out a lot.
Chapter Two
This night I was approached by Matt first. “Hey, I know you’re cool with one-on-one stuff. But what do you think about taking on more than one of us?” he asked.
Ever since Jim had shoved his cock in my mouth while Matt fucked me a few weeks before, I had wanted more. “I’d love to have a dick in every hole,” I admitted to him.
“Okay, guys, she’s good with it,” he shouted as three other men came into the room.
“Hey, did you ask her if the other guys can watch?” one of the men, who I knew as John, asked.
“Yeah, but they can’t join in. We don’t want too many of them coming at her. It may lead to something more dangerous happening,” Matt stated.
The room filled up, many of the men eyeing me like I was prime rib and they wanted to devour me. I could feel my juices as they began to flow between my legs. This was something I enjoyed a lot. I almost wanted to tell Matt to let the other guys join in, but later I was happy that I hadn’t said the words.
Matt introduced the other men to me quickly. John was a white man who was around 40 years old. Then there was Manny, a younger Spanish man. Finally, there was Jack, the Puerto Rican who had just been incarcerated.
They already had hard dicks and they were out in their hands. I went over and bent down in front of Jack. His dick was around six inches and I knew it would be fairly easy to deep throat.
As I wrapped my hand around his shaft, I felt the pulse of his blood flowing. He was very excited and probably wouldn’t last long. I swallowed up his full length and looked up into his face.
He smiled down and held my head in place as he fucked my face in a pace that was hard to keep up with. I almost chocked on his cock a few times.
As I was pleasing him I felt hands on my pussy and looked to see John had placed himself to view my pussy and he was pushing his fingers into me. He thumb was rubbing my clit at the same time, and I felt my first orgasm peak and the juices gushed out, covering his hand.
My own pussy juices were used as a lube for Manny as he pushed into my pussy for a few thrusts and then moved to my ass.
I heard Matt warning, “Manny, take it easy. She’s a virgin back there. Don’t hurt her.”
Manny took his time as he pushed inch by inch of his seven inches into my ass. When he was finally in there, the fit was tight. I could feel every pulse of his blood. He began pushing his cock into my tight hole at the same time I felt another cock placed on my lips.
I opened my mouth to Matt’s 12-inch snake and tried to take it all down. I moaned with pleasure from the cock in me and felt another as it slid into my pussy. I orgasmed as I realized each of my holes was filled by man meat!
I felt every inch of Manny’s cock as he pushed in and out of my tight ass. “I can’t hold it anymore.” He moaned loudly as I felt his cock jerk and fill up my ass with his juices.
John was fucking my pussy as Matt pushed in and out of my mouth. John pushed his dick into my well-used ass and pushed in fully. I moaned as I was once again filled up in each hole.
I chocked on Matt’s cock again as he tried to push all of it in my mouth. “I can’t take all of you,” I told him.
“Just keep sucking. I’m going to cum in your mouth.” He pushed into my mouth again. I tried to resist a bit, but knew it wasn’t worth it. I was enjoying being used by these four men.
I could see a few of the guys watching with their dicks out, stroking them up and down. All this sexual adventure in one room made my pussy tighten up around John’s cock. His nine inches had been pounding me for a bit now. I could hear his moan and he went still as his sperm rushed out into my pussy.
Matt felt my orgasm shudder through my body and it pushed him over the edge. He held my head in place as he pushed one last time into my mouth. His cock buried at the back of my mouth, his sperm flowing down my throat with each of his spurts.
John had cum inside of my ass as Matt was finishing up in my mouth. He had pulled out and I had more sperm on my back than in my mouth!
I loved the feel of all this sperm on my body. I pulled Matt down and told him I wanted a few more guys to come on me.
He looked at me to be sure that I was sane. “They’re going to want to fuck you too,” he said.
“Just a couple more, then. No more in the ass either. I’m really sore back there,” I told him.
He chuckled and went and tapped a few of the guys in the crowd.
There were soon two more cocks in my face, and one in my pussy. The guys almost got into a fist fight as they tried to maneuver their cocks to my holes.
Matt thankfully kept them away from my ass. These guys didn’t last long at all and soon all three had sprayed cum juices over my body.
I noticed by this time that Matt was rock hard again and he slammed his black pole into my wet hole. He was rough with me, pounding my hole like it was the last time he would ever see a woman’s pussy. But I loved it and I came hard as he thrust into me in strong hard bursts.
I raked my fingers down his back as he punished my pussy with his hard thrusts. “Fuck me hard, Matt. Come on, fill me up too. I want you to fill me up so much I can’t hold any more cum in me.” I talked to him dirty.
My pussy was sore from all the dicks I’d had already, and Matt seemed to want to make sure I couldn’t take another one in that hole. He banged me so hard that my eyes began to cross with each of his thrusts. I was pushing back towards him too.
Chapter Three
He pulled me up quickly and soon I was sitting on top of his body. His cock was still buried deep inside of me. I was in control now, or so I thought. Matt grabbed my waist and easily picked me up and slammed me back down on top of his rock hardness. I felt like he was splitting me in two, he was so deep as he drove me down harder with each thrust.
“Oh shit, you’re going to break her in half if you keep that up,” I heard one of the other guys yell.
That made Matt thrust me down even harder on his 12 inches of black snake. I felt my body tense up as the orgasm started. My pussy walls squeezed around his cock. He pushed me down another time on him and held me in place as his sperm emptied deeply into my punished pussy.
I fell down forward on his chest. My hair was soaked with sweat and I was completely drained of all my juices.
Matt pulled me forward one more time and kissed me roughly. “You’ll always be mine, no matter how many cocks you take.”
He was right. Matt has always been my favorite of all the guys. I’ll be upset next year when he gets out. I might just let him come live with me. At the least it will mean I won’t miss out on his black snake. I’m sure he would be alright knowing what was going on at work.
That day I went home and took a hot bath. I was sore all over. My mouth had been stretched wide, as well as every other hole on my body.
It wasn’t the last time I had sex with the men. Hell no, I enjoyed it far too much. The most men I’ve had cum on me was around 10. I couldn’t go over that. They want to fuck me or have me suck them off. My stamina isn’t up high enough for more of them. But I have a feeling that they are trying to get me used to it, so I can pleasure them all in one night.
I would be lying if I said the thought of it hasn’t had me masturbating and cumming in puddles on more than one occasion. Maybe today at work will be the day I take more of them on!
Story Nine
Chapter One
The sun blazed brightly high in the sky down onto the city of Portland. Summers in the Pacific Northwest were dry and incredibly pleasant. It was the opposite of the cold, damp and rainy winters, when there was no sunshine for six months at a time. Bright light entered through the window to Chelsea’s bedroom and its rays shone on her face and eyes. An alarm clock from nature, the rays made Chelsea’s eyelids flutter and open.
Lying in bed, her mind communicated to her what she needed to do first. It was June 29. Friday. That meant no class until Monday. Need to review notes for graduate Anthropology research grant application over the weekend. What else? She asked her mental to do list. That’s it, it answered, morning is free. And, oh yes, tonight you are going out with best friend Christine to Holocene, be ready by nine tonight.
Ugh, she sighed, remembering their date tonight at the nightclub called Holocene. It’s a meat market, Chelsea had protested to Christine. No, it’s not. Besides, we’ve been working our asses off. We’re just going out to have some fun, no expectations, no strings attached, okay Chelsea? Okay. But to herself Chelsea said, Okay? Not okay. I’m fat and I have no clothes to go out with that fit me right. Rising, she walked slowly to the kitchen and pressed the coffeemaker button. A moment later she heard water percolating, and a moment later the aroma of brewing coffee. She walked to the bathroom and turned on the water, which would become very hot within minutes. She pulled off the straps of her dark blue teddy, and removed the matching panties. As the water steamed up behind her, she took a good look in the mirror. She saw her large, round breasts protruding from her chest, above them her somewhat narrow shoulders. Her arms looked shapely to her this morning and not fat. Her arms complemented her boobs just right, and as she looked down to her navel she saw her belly. She had lost 35 pounds on a punishing diet that denied her all her favorite foods. But it had worked, for while there was still extra skin there, she could now see how curvy and attractive her shape was. Under her belly were her legs, which tapered down to her smallish feet. Her skin was pale and mostly clear of bumps and birthmarks (there was a minute skin discoloration behind her left ear). She had recently had her hair styled, and she tossed her head and felt the waves of her red hair move against the air. Her hair was short and pretty, and the natural red and orange tint of her hair always attracted attention.
At the end of her review of herself, which came out well, she took a long shower, grabbed a towel and walked into her bedroom to face the mirror and do a reassessment. This time she saw that she was pudgy, too pudgy, what some call curvy but what most considered simply fat. So tonight I go out with Christine to get publicly humiliated, to see what others see, and then drink too much and start to cry and feel sorry for myself. What’s the point?
Looking at her clock, she saw it was only 7:30, too early to call her friend and cancel their date tonight. But, she thought, Christine always sounded excited talking about it this week, Okay, then, I’ll do it for her. Hopefully she’ll get bored so we can leave and walk around the park instead.
She went into the kitchen and poured her coffee and sat down at the kitchen table. Drinking coffee in the peace and quiet of morning before her neighbors in the apartment next to her woke up yelling at each other was her favorite time of day. She closed her eyes and her mind wandered back to when
she was a teenager. Though she had been seventeen less than a decade ago, it seemed to be in the distant past. She’d done well in high school, and gained an interest in anthropology after reading a book by Ruth Benedict, a woman who had gone to Africa and lived there for years studying the social habits of chimpanzees and other primates.
Her friends used to tell her how pretty her face was, her wonderfully soft light skin, green eyes and blazing red hair. Unlike her friends, though, the weight she carried as a little girl remained a part of her through her teenage years and up through the present. It was as if her body was designed for her to carry extra weight. She and her girlfriends used to enjoy going to Lloyd Center Mall to look for clothes in all the big department stores. She liked that she could find fashionable clothing in her size, and a few of her outfits brought out her sexy curves.
As she got older she disliked herself more and more. She would become successful in her field, yes. But also in her future was waking up in the middle of the night in the quiet and deadness of the world. And she would be alone. No sex toys could hold her and kiss her in the dark of her bedroom. She sighed, finished her coffee, and started her day.
Chapter Two
Her phone dinged with Christine’s text that she would be there in 10 minutes. Chelsea checked herself in her bedroom mirror one last time. She wore a white blouse that was tucked into a dark burgundy skirt whose hem fell just above the knee. The skirt was a light velvety material, causing it to glimmer under bright light. The phone dinged again, signaling that Christine was waiting outside. It was a warm night, so she only carried a light sweater in her arms.
She walked out to the car and saw Christine's eyes widen as she approached. She sat in the passenger seat, and Christine stared.
“What’s wrong?” Chelsea said anxiously.
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