The Ugly Duckling
  • Author - Dick Redding
  • Rating -   
  • Site Rank - 2682 of 2955
  • Story Codes - M-f, consensual, non-consensual, analplay, bondage, slavery
  • Post Date - 1/21/2013

Author's Note: This is my first story. Please be kind.

English is my first language so grammar errors are my responsibility. However, be aware that for dramatic effect I have intentionally ignored certain sentence structure rules.



"Guilty!" reported the judge as she banged her gavel.

No! Can't be. What? Were the first thoughts that cascaded through my head.

It's funny what you think about when you go into a type of shock.

For me - I thought about how this would have appeared by one of those courtroom artists - you know, when they can't take a picture but "artist's" renderings are allowed. The picture of the judge up on her stoop, tall, statuesque with her neat blond curly hair and flowing robes contrasted by me, the defendant. The one time I had ever worn heels it got me up to almost 5 feet and my hair was short, lanky and deep black.

"The court sentences the defendant, Pat Canard, aged 18, to a term of 6 months less a day to be served at the County Rehabilitation Facility"

What few friends I had over the years had talked about "Late Bloomers" and how my time would come. Well, my period had arrived 2 years ago, but nothing else did. In a time where everyone seemed to consider a C cup as average, I was an AA. Friends referred to me as plain. In grade ten French class, the class got great merriment when they found out that my last name meant Duck in French. After that, I was the Ugly Duckling and even my friends found it a nickname that was hard to avoid. It wasn't unusual for little kids to call me Sir. Life had apparently decided that femininity wasn't to be mine. And now that I was judged guilty, apparently freedom wasn't to be mine either.

I looked to the defense attorney to my left. I think he said something like "Surprised" and "Appeal" but I really didn't hear him. In a daze I was taken out of the courtroom for processing where I was given my new clothes - all in prison orange. I didn't think much of the fact that I was only issued a pair of boxers but followed all instructions and left all my old clothes, undies included, behind in a cardboard box.



It might have been days for all I noticed what was going on about me but it was probably about eight hours later when the prison van pulled into the facility. I was the only prisoner led out of the van and brought through a series of doors leading into the jail. If this was a movie, doors would have slammed shut behind me, sealing my fate. Instead, I was led into a room marked "Intake". There I was met by what I guess was a senior guard. My legs were weak and I would have wanted to sit down but there weren't any chairs. The guard said "Welcome to Monroe Prison. Your home away from home for the next six months. Keep your nose clean, do as you are told, and you will survive"

The guard stared down at me at asked "Understand?"

"Yes, Sir" was my timid response. A part of me wondered why a male guard was handling the introduction but who knows, this could be the usual process. I was new to this whole "Jail" thing.

"Our other *guests* are all watching a movie - I think it is Home Alone tonight. I will bring you right to your cell - you can meet your new roomies later."

At this point, I followed the guard as he walked me to my new home. Through my fog, I saw rooms and cells and cells and more cells and bars upon bars as we walked what seemed like forever. Eventually the guard stopped, opened a door, and pointed inside.

I turned the corner and looked inside. Two upper bunks, two lower bunks, a toilet, a sink and a girlie poster on the wall. My mind thought "Shawshank" and then the door slammed behind me, driving home that I was a prisoner and under the control of the state. The lower left bunk seemed unused so I crawled in, curled up, and started to cry. Eventually I heard doors open, sounds of others entering, bunks being crawled, and squeaks of mattresses. Oblivious, these might have been on the moon for all I cared. Sometime later, lights went out and sleep followed.


I awoke as I felt myself being moved. As I opened my eyes a hand slammed down over my mouth. "Keep quiet".

I had been on my back and my head had been dragged over the bunk end. My head was dangling towards the floor and when I looked up in the dim light all I could see was some inner leg, balls and part of a penis. A penis that seemed to get larger as I stared. Someone else was sitting on my stomach holding me down as another pair of hands tied an arm to the bunk side. The same whispered voice repeated "Keep quiet. Co-operate and we let you keep teeth. Bite or yell and we turn you into a gummy worm. Capice?"

I had gone from an exhausted sleep to wide awake in a moment flat. I nodded my head. I felt my jaw being wedged and then a warm round item hit my tongue and inner mouth. The voice - "Now suck cupcake". I sucked. I blew. I licked. Again. And again while desperately trying the keep my teeth apart. I didn't care. I had never done a blow job but it didn't matter. The whole universe was the need to suck, to lick, to blow. It seemed to be a long time but probably wasn't. Then the universe was the need to breathe as my throat filled with the warm, sticky, and incredibly salty jism. I swallowed.

My eyes saw the body above me relax as his body released. I heard "good job cupcake" as his penis was withdrawn and I could breath normally again. I maybe got in two breaths as the bodies on top shifted. The new penis above me seemed to be closer still, as if looked at through a magnifying glass. Not a pretty sight and such hair. Ugh. I felt my jaw being pried open again and the different penis was inserted. "Again cupcake. Don't become a gummy worm."

My world returned to the need to suck and lick and suck and lick as I felt the various ridges of the penis along the tongue. This penis was shorter than the last and my tongue seemed to be all over the head of the penis. History repeated itself as again my throat was filled with the intruder's jism. It became all my will to avoid biting in startlement as the body on top of me slid sideways and another took its place. During this momentary change, I had time to become afraid. Would I be raped? What would come next? Would I be raped? Would I be killed? Would I be raped? All raced through my head.

My third cellmate slid in and once more I felt a hand reach for my jaw. I opened the jaw wide and waited. Another dick was inserted into my mouth - and I was immediately surprised. The previous two dicks had been large, swollen and dry as they entered. This one was soft, small and already wet and tasted, well, stale. By then I did know what I had to do and resumed my tongue work, licking the flaccid member. I kept licking, wanting this to be over. I could feel my saliva roll around my mouth but nothing seemed to happen. I started to try to get my soft lips but not the teeth, never the teeth involved. It seemed to take forever but the dick began to put pressure on my tongue. A few more minutes of action and I could taste more salt and I felt him try to pull out. I opened my mouth as I saw legs, balls, and a now tired dick withdraw to be replaced by the image of a dark grey prison wall. I felt my arm being untied and the body sitting on me slide off. A different voice whispered "Welcome to Monroe cupcake" and I became the only occupant of my prison bunk. I shimmied over towards the wall and rolled to face it. As I did so, I could feel wetness soak through my clothes onto my chest. I thought "Oooo" and tried to think about anything but what had just happened. Maybe I slept, maybe not. I now had the pictures of three penises burned in my brain but had yet to see a face. No how did I wonder just where these penises had come from.


I awoke to the sounds of crashing and banging as the prison woke up to its daily routine. I just wanted to stay curled in the bunk forever but that wasn't going to happen. A hand touched my shoulder, shook, and said "Get up cupcake - we gotta get in line to shower and chow. The bull guards like to thump anyone late, especially a newbie. Then you'd be in the hospital and we won't have anyone to play with. So get the fuck up!" I turned over and looked into one of the most beat up faces I had ever seen. Someone, sometime, had beaten the crap out of this guy, probably more than once. His jumpsuit said Mortensen with the letters MMP below them. I hadn't known my clothes were labeled.

Looking around the cell, I could see my other two cell mates. One pretty tall, big, like a football player and the other one short, squat, chubby and round everywhere I could see. Their prison garb said they were Biggs and Cyr respectively. I wondered which order they had forced themselves on me the night before. I pushed that thought and a wonderment why they had stopped at forced oral as far in the back of my mind as I could. It never occurred to me that my first thought should have been "Why the fucking hell did they put me in a cell with guys".

I could see prisoners lining up outside their cells and followed my cell mates outside the cell. I ended up in line between Biggs and Mortensen. As Biggs was about a foot and a half taller than me, I couldn't see much beyond Biggs' backside. I did notice a guard walking along the catwalk. I started to raise a hand to draw attention from the guard when I felt a jab to my kidney from behind. A prison whisper said "Are you a fucking fool cupcake? Open your mouth and it won't just be your teeth you will lose." I stood still.

The line eventually started to move and I followed. Where the line went, I went. Eventually the line of humanity reached a change room and I could see something other than Bigg's behind. And I realized that I really did have little choice of view as everywhere else I looked was mostly naked behinds. Male behinds. Fronts too. I was just about the only person still clothed and obviously that was going to draw far more attention to me than I wanted. I could disrobe. As I had mentioned, I was discouragingly flat chested and from the looks of some of the other prisoners, upper body workouts was not the norm. There were a lot of breasts flapping about much larger than mine. Ew. I started to disrobe wondering what I would do about the underwear. There wasn't a guard to be seen and removing the boxers, revealing my vagina, could just cause a riot. I had a mental picture of dozens of instantly erect dicks, all homing in on me like ants on a dropped ice cream cone. I shuddered but realized that 2 or 3 of the men had left their boxers on and were heading for the showers. It didn't make much sense but it seemed to be the way out so I followed suit and joined the scrum for the showers.

In the shower was a press of humanity. I felt two hands grasp my shoulders from above and I was pushed back against the shower wall. Looking up, I could see the face of Biggs, looking at me expectantly. With a look I couldn't quite understand, his right hand reached down and slid under my boxers. I was looking at his face when his probing fingers worked their way through my scanty pubic hair and found the uppermost area of my slit. I could see his look of expectation turn to one of shock and surprise. I felt his hand move upwards for a moment and for the briefest of moments I thought I had gotten a reprieve. Then the finger moved downward and found my clit. Wow. My body seemed to be interpreting the stress of the situation as excitement as when my clit was touched, it sent waves of impulses throughout my body. The impact of *his* finger caused *my* fingers to tingle even.

Biggs finger moved around for a few moments in a circle. Nice. Then it moved further. Deeper and Deeper. Finding interesting and wonderful places. He was moving his fingers in slow circles, deeper and deeper. With every movement, the impulse waves got more intense. Pleasurable. Fun. Then he stopped. I looked at him and his look of surprise had turned into a look of determination mixed with Glee? He said "Well. This is a fantastic surprise. A real live woman in our little prison. Don't worry darling, Biggs and friends will look after you. And you will look after us."

At that, the head guard shouted "Get dressed and head to chow." I followed the herd, toweled, got dressed and joined the line heading out. Biggs followed me everywhere, never more than 2 feet away. If it wasn't for the look on his face, it might have been sweet and puppy dog like. His face was anything but that of a puppy.

The first time he separated from me was after we arrived in the chow line. He quickly left and joined up with Mortensen and Cyr. They both, almost in synchronization, looked at me from head to toe. They lingered at my chest area and positively stared at my crotch. I felt like I was being scrutinized for sale. I was to find out later, in a way I was. They said something else between them and then were lost from sight. I continued down the line, grabbed whatever was offered on the line, and tried to find a seat alone. Within seconds the trio had found me and had filled up all seats around me. Biggs looked at me and said "Just consider us your Guardian Angels. We will make sure that no one bothers you. Well, not more than we want. In return, you just do what we tell you. Listen to us and we will keep you alive to finish your term. Jerk us around and no idiot in the place would give you odds on surviving the day. Capice?" There really wasn't much to say to that but a nod and returning my attention to the tepid sausage and burnt toast that was breakfast.


The day passed more or less uneventfully as one or more of my "Angels" hovered over me, discouraging contact with other inmates and more importantly any guards. By now I had discovered that the MMC I had seen earlier referred to Monroe Men's Prison. Somewhere, something had gone very wrong. The best guess I had was that with my androgynous first name and plain looks, someone at processing had just made an assumption and sent me here. I would have been terribly insulted if I wasn't already terrified. A part of me wanted to find the first guard I saw and tell him my story. However, with my "Angels" around I was afraid of what could happen if the guard didn't immediately believe me. A vivid imagination allowed me to envision any number of gruesome fates, all worse than the immediate present.

After a long, tiring day, at night call, I entered my cell for night 2 of my state planned 180 nights at MMC. As the lights went out I crawled into my bunk, trying to be as small and inconspicuous as possible. For some reason, I thought that staying awake was best. I listened to the sounds of men snoring, of men coughing, and very occasionally, of guards walking. I did try to stay awake. I did. But eventually I awoke with a start as I was pulled from my bunk on to the hard, cold floor. I started to squeal in surprise but a clamped hand quickly returned me to silence. Almost as quickly as the last time, I felt myself unable to move. Another hand joined the one at my mouth and I felt something cotton being stuffed in, silencing me. I felt another set of hands tie a belt around my body, trapping my hands against my side. Still yet the last set of hands quickly pulled down my pants and boxers below my knees, trapping my feet. Hands pulled my thighs apart as a cool wind tickled my slit. No words had been spoken and here I was, half naked, trapped and mute.

Even an ugly girl can find a boy willing to fuck her once or even twice so what came next wasn't my first time. Close, but not the first. I felt a finger reach in and separate the folds of my vagina. It moved. The finger circled a little bit. It hit some nice spots and my body did what evolution had taught it to do. It got wet. Just a little bit more finger movement around the right spots and my cunt added to the wetness. My sex was as ready as it was going to be as it felt a firm round probe begin to push against it. A little more. More. Insistent. First the head and then the shaft as it entered me. Retreated. Entered. Retreated. And so on. My previous experiences with voluntary fucking had not been satisfactory - quick, messy, and entirely one-sided. And so it was to be here at MMC. Whichever of my roomies had gone first deposited his load of sperm deep in my ovaries in seconds. I could feel the sperm deep inside me as his dick continued to thrust and parry. Thrust and parry until he pulled out.

I had a brief moment to hope that this was a onetime experiment and that they weren't interested in sloppy seconds. My hopes were very short as bodies shifted and a new body was on top of me. I won't detail the experience but the sloppy seconds, and shortly afterward an even sloppier third was much like the initial rape. In the dark, I knew who each of my rapists had to be but couldn't have told you which was which.


The following days were mostly like I would have expected in prison - lots of boredom, lots of time. During the day one of my "Angels" was ever-present. Have you ever tried to lose your shadow on a sunny day? Nights were also consistent - the nightly process of oral and vaginal sex with my roomies. It had become less rough - after all we all knew what was going to happen and that I didn't have any options. What had started as a rude awakening and a slam on the floor evolved to a shake on the shoulder with me removing my own clothes. "Why make it any worse than it needs to be?" became my attitude. One night I was surprised when after having been cunt fucked by Mortensen and Cyr and waiting for Biggs, I heard a murmur of "Ew" and then was flipped over. I suppose this would have been problematic for a larger, better endowed woman, but there really wasn't anything to get in the way. I wasn't expecting the flip and my tongue and lips made contact with the concrete floor which hadn't been cleaned for a long time. While I was trying to spit out the grit I felt my hips being pulled back and up. And then pain. ow. Ow. OW. OWWWW as Biggs' penis penetrated my virgin asshole. Out. In. Out. In. .... and then finally out. Biggs returned to his bunk, leaving me lying on the cold floor, with a soaking wet cunt, a wet ass, and dirt on my teeth. I lay there for a while before deciding that I might as well do the same, but on the softer and somewhat more comfortable bunk.


The following morning I received another example of how little control I had over my life. I had vaguely noticed that there were a number of prisoners who were "different". They had modified their uniform in various ways, kept long hair and wore makeup. Garish makeup, but still makeup. In terms of ugliness, most were my match. Putting blue eye shadow and red lipstick on a plain featured, small framed, weak man does not, repeat not, make him a voluptuous woman. Talk about putting lipstick on a pig. However, I guess that, in here, it is the thought that counts. I had heard them referred to as "gurls". I did find it ironic that, here they were, guys trying to be a woman while I, the only woman here, was desperately hoping that no one else figured out I was a woman, for fear of the consequences. Most nights I had night terrors of being exposed. The dreams were not very clear but they all followed a pattern - accidental discovery in a crowd. Upon discovery, the crowd goes wild, and my clothes are torn off of me. There I am, standing naked in the room, trying to hide my sex with one hand, my breasts with another hand, and my ass with my third hand. This works for a while until in the dream realize I only have two hands. Then the crowd is on me and gang rape ensues. Penetration from the front, from the back, through my mouth with a dick in each hand. In this dream, somehow the guards never notice, and the prisoners have truly amazing stamina and massive dicks. I cringe at the thought.

Most days, my "Angels" discourage interaction with other prisoners. Individually, there are certainly other prisoners who could match any one of the "Angels" in toughness. As a group however, there wasn't much competition. I guess I should feel flattered to have such great "protection". Today was different - during "Free Time" Mortensen brought me to another cell. In the cell was one of the "gurls". She was different than the rest in that she actually did seem vaguely woman like. Her features were soft, her makeup was attractive, and she actually had breasts. B Cups only, but still breasts. For a moment I felt my hopes rise. Was I no longer alone? Mortensen gave me a glare and explained "Danny here is a very special gurl. Unlike the others, she was actually a pre-op t-girl before getting popped for murder and ending up here. She is going to get you set up for us. Listen to her. Capice?" What could I say? I nodded and turned towards Danny as Mortensen took a position outside.

Danny looked at me from head to toe and shuddered. "It ain't going to be easy but we will see what we can do". Over the next couple of hours, Danny fussed over my hair, put makeup on and took makeup off until she was satisfied. Any attempt at conversation resulted in a "Shh" and a slap on the ass. Eventually she told me to remove my top. There I stood, naked from the waist up while a genetic male peered at my breasts, utterly uninterested. She reached in a bag and pulled out a purple underwire push up bra with lots of sequins. "Here, put this on. It is one of my old ones but you will need it". And so I did. I looked down and could see the inside of the bra hanging about 2 inches away from my actual breast. I felt ridiculous. Danny thought it was great. "Perfect. Just what you need for the right look. A couple of pairs of socks are all you need". She held up a mirror and I could see myself. Danny had introduced some curls with purple bows into my otherwise straight hair. Purple eye shadow, rouged cheeks, purple earrings, and the reddest lipstick I had ever seen. Down below, a purple bra peeking out from the prison top. Mortensen stepped back inside, looked me over, said "It'll do" and walked my out of the cell.

I soon discovered just why I had received this "Extreme" makeover. My "Angels" had decided that I was worth sharing with a few of their select friends and acquaintances. Aside from our nightly encounters, I was now the "Angels" whore, to be provided in return for favors, ranging from a pack of smokes to a shiv in the back. If it was minor, I provided hand jobs. Medium favors were returned with a quick trip to my tonsils. For significant favors to well known cronies, my "secret" was revealed and we fucked. Well, technically I was fucked but this wasn't real important to my "Angels". After about a month of this, I was surprised when a guard escorted me to the head CO's office.

The guard walked me into the office, said "Sit", and left, closing the door behind him. I hadn't personally met this CO before but had seen him around. His uniform had Robertson on the name badge. I sat down as Robertson looked at me. "Ahem. I have heard some interesting rumors about you Canard. If true, it will be very, very embarrassing for a lot of people. Heads will roll and that kind of shit. Professionally, I would be very, very happy if the rumors are wrong. However, I also have a daughter about your age. If the rumors are true, I really don't want to think about the results. So I will ask you straight out - Are you, in fact, a woman?"

This could be my chance. I sat there, in whore makeup with a bra way too big for me, with sperm still wriggling around my cunt and my ass from an earlier "favor", looked him straight in the eye, blinked, and said "No fucking way. Are you fucking nuts?" Robertson smiled and called for a guard to return me to my cell. You might wonder why I answered that way, after all I had been through and what I could look forward to. You might wonder why I denied my womanhood when it could have gotten me the fuck out of there. You see, out there I am just one more flat chested, ugly waif. But, in here, I am always the prettiest girl in the room.





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