Cobra's Moll

Cobra’s Moll
A Short Story
By Maryanne Peters

I was prepared to be sentenced to prison for my crime, but the truth is, I was totally unprepared for prison. My whole life I had lived in comfort. My parents had raised me in comfort. I boarded with an aunt through my college years, in comfort. Even from my early years employed in a law firm I had more than sufficient to live in comfort. And latterly self-employed, I had lived in comfort and for comfort. My taste for comfort had led me to take the money, although the truth is that I had always had a slight inclination to deceit. What a reversal for me prison was.

There is no welcoming committee when the door slams, no orientation procedure. You must fend for yourself – start swimming at the deep end. And the water inside is deep. The truth is I was a clear victim. Small, slight, clean, and perhaps a bit of a mommy’s boy, I was clearly earmarked a some ruffian’s bitch. I was not so naïve that I did not recognize that. I knew that I needed protection and that I would have to pay the price for that.

So I sought out Cobra Miles. I had learned from a guard that he was the best of the powerful men in the wing where I was to be housed. From the moment I arrived I told people that I had a message for him, which was a lie but which did keep people off me until I did actually meet him.

That meeting took place about 3 days after I arrived. Two large white thugs collected me from my cell and escorted me through various corridors to a room marked “Art Therapy”. This room had in fact been converted to a large cell for Cobra Miles and his inner circle. There were curtain partitions separating sleeping quarters, similarly separate kitchen and sleeping areas, a large meeting table with chairs, comfortable sofas and against one wall what can best be described as a small grandstand in the center of which sat Cobra himself surrounded by henchmen,

Corrin Bateman Miles was no ordinary thug. Outside prison he was rumored to have been a large drug dealer and loan shark, who had personally murdered 7 men, but he was in prison for a relatively minor “road rage” assault. He was caught on camera only a short distance from the airport where he had stepped off a scheduled flight, so his usual network of alibis and stand ins were not available. That relatively minor attack still caused major injury and he would remain in prison for another 3 years with good behavior, longer than I was expected to stay.

In appearance I was a little surprised. He was tall and athletic, with strong and not unattractive features. He was clean shaven with dark hair and penetrating blue eyes. There was clearly a streak of violence in him that was plain to comprehend, but there was also an intelligence. In a word he was intimidating. I started to wonder if the message I had would be enough. My message was simply that I was available to assist him with legal advice in connection with further charges that were being prepared against him to keep him inside. This was no message at all of course, and I could easily have been expected to be thrown to the wolves, but Cobra Miles looked me up and down and accepted my offer.

“It is this simple”, he said, “Be my bitch or somebody else’s. If you are my bitch then I need never lay a hand on you, but as long as your ass belongs to me no fucker touches you. Do you understand? If you do legal work for me you do it as my bitch. I have only two kinds of people here working for me – gorillas and bitches. These here are gorillas”, he said motioning to the collection of thugs around him. “You ain’t one of them. You will join my bitches.” And he then summoned out from an adjoining area a weird group of people that came as a total shock…

Into the middle of Cobra’s parlor-like cell walked four women. Not women as it turned out, but inmates dressed as women - Cobra’s harem of transvestite girlfriends. But so convincing. If you had not known the circumstances it would have been so difficult to believe that these were men. They had bodies of female appearance, long hair (not obviously wigs), pretty faces, they wore feminine clothes and walked with true grace right up to me, two of them taking me by each hand.

“You see, I am no queer my friend”, Cobra explained. “I like my bitches to be women. If you ain’t a gorilla you join these girls … or you take your chances in the real world.”

And I said: “Forgive me Mr Miles. I am no queer also. If I am going to get fucked by you, is that any better than being fucked by someone else in this place?” It was a bold statement. Instantly I wondered if it was a not a little too bold. But he smiled and replied: “Truth is getting fucked by me is better. But as I said I never need lay one finger on you if you serve me in other ways. Just ask Jonelle here.”

The one identified as Jonelle simply leaned over to me and whispered (in a girlish voice): “Just take his offer and join us. You will not regret it.” So I did join them. The truth is that my options were limited. I was not prepared to risk the real prison and total protection even if it came with a costume, sounded better.

As it turned out Jonelle was Cobra’s cook. She sourced all kinds of fresh ingredients through arrangements with the guards and made some special meals. Cobra had some fine tastes in food although his favorite was goulash. Jonelle was in her (I say her because she was obviously female to me) mid 20s, slight and dark haired. Like me she was no queer but had chosen this path for survival. She insisted that, true to his word, Cobra had never asked for sex with her, but he did insist that she act as a woman at all times, in his presence and at all other times.

Maple and Sassy were definitely on the queer side. They had both been queens before prison, and Maple had even had some kind of operation. They played the ditzy blondes. Both were proud to say that they had been impaled by Cobra Miles. They were both dressed in sexy outfits and sat attentively near to their master at his call. Sassy was quite a large person, and (unlike the others) had a face that might have appeared like a man in drag. But the body was impressively female, and her copious blonde hair was real, and tied in a high pony tail, it was gorgeous.

The fourth member was older. She had red hair cut in a long bob and she had a quiet demeanor. Dolly (as she was called) was the bookkeeper. Before sentence he had been an accountant, and by reputation a good one. Child molestation had seen him sent to prison. Child molesters in prison can expect the worst treatment from fellow prisoners. As he explained it becoming Dolly served as protection and also allowed him to submit to physical castration, something he had sought in an effort to suppress his perverted desires. As he told me later, he had a wife and two daughters (whom he had abused). They would never contact him again and all other contacts (friends and family) were lost. He saw himself as totally alone and sexless, but in women’s clothing. When I was able to put aside thoughts of his/her crime (which I found particularly disgusting) I found Dolly to be a good person. She was intelligent and good-humored. The truth is that she was not as isolated as she thought she was - Cobra Miles had given her a place.

It was Maple and Sassy who took me in hand to effect the necessary changes.

Firstly, I was taken to the bathroom that adjoined the room, where I was stripped naked and had all hair removed from my body – except a small area of delicately trimmed pubic hair. My beard was left and the first stages of removing it hair by hair was undertaken by both of my attendants, working one on each side. Sassy had a collection of beauty manuals and told me that she intended to set up business as a beautician when she was released. As she was inside for drug dealing, that would not be for some time.

Then came the injections. Androgen suppressants and strong female hormones were available and administered. Apparently the presence of these drugs in prison was illegal but tolerated by prison authorities on the basis that they had a positive effect in reducing violence. The presence of testosterone and muscle building drugs such as those used by Cobra’s gorillas was less popular with the warden, and despite his maintaining a cordial relationship with such a key kingpin, he occasionally subjected Cobra’s quarters to searches for these.

In addition to the injections and regular boosters I took pills. My diet was adjusted, and I joined the other girls in an exercise programme designed to promote a proper female shape. Certainly, it appeared to work for them.

I should say that when I agreed to go down this route I had not expected the hormones. Agreeing to dosed had the feeling of taken a move that there was no going back from, but the girls assured me that the effects could be reversed. Only “The Operation” was irreversible, and nobody was talking about that.

I learned quickly that my primary purpose was to be “eye candy” for Cobra and his boys. As such I was expected to act in an overtly feminine fashion at all times. Any dropping of this persona even for a moment, would be punished with loss of privileges. The ultimate punishment would be to be cast out, either forever or merely for a day. Given my evolving condition that would most certainly result in my being gang raped, or possibly killed. These were strong motives to keep in line.

What I needed to learn was made easy by the fact that we “girls” were all working together. Maple had some video tapes about ladies’ deportment, and we also watched endless “chick flick” videos to pick up actions. The truth is that it was huge fun. We were “in character” and we would giggle and carry on talking about clothes, make up, hair and girly stuff.

Even though I remained totally heterosexual in outlook, as did Jonelle and Dolly, we would also talk about some Cobra’s gorillas as “hunky guys” and discuss their relative merits as potential boyfriends. Again, it was just pretending and was a wonderful way to pass the time.

And time did pass. I found my feminine behavior becoming increasingly automatic. I found myself gasping at tales of violence, throwing my hands up at the sight of a cockroach, giggling at silly things, and increasingly losing the ability to do simple male tasks. Most of all I found that my new focus on my appearance made me constantly check myself, primp and preen.

At the beginning I had worn a short bob cut blond wig, but as my hair grew out fed by female hormones and treated by hair preparations, it developed as thick and lustrous light brown, adjusted to a honey blond in Sassy’s makeshift hair salon. One of our activities was experimenting with hairstyles. Even Jonelle and Dolly joined in. Dolly in particular had developed a special skill in French braiding and putting hair up. Sassy had a collection of curlers and hair tools and we would regularly submit to a shampoo and set. It may sound odd, but in prison such amusements become the closest thing you can get to having fun.

We also experimented with clothes. Cobra had arranged for a steady supply of ladies underwear, and to assist us in shape he had also procured some fake breasts, devices to hold in our bits for a flush crotch, and one set of padded pants to give the appearance of a female butt. Jonelle had appropriated these so that when she worked in the kitchen wearing her usual short floral dress and apron, she could flash her bottom appropriately. Maple had a skill in dress making. She had worked in the garment trade in younger days and was able to develop her skills with the sewing machine that Cobra had sourced, and a supply of fabric. She would prepare outfits, sometimes purely from pictures from magazines, and we would parade around.

Sometimes we would arrange fashion shows to entertain Cobra and his boys. Generally these started as sophisticated affairs with outfits and hairstyles lovingly conceptualized and executed, but they usually descended into strip shows with cheers and chants from the gorillas followed bum pinching and breast grabbing, and then everyone collapsing in peels of giggles.

All of this made my time in prison better than tolerable.

Sex – well there was no doubt that Sassy and Maple were getting plenty. It almost seemed as if Cobra had tired of them. He seemed to pay more attention to me, Jonelle and even Dolly. On one occasion when Dolly was running through figures Cobra asked her to sit on his knee and he stroked her hair while she explained things to him. I remember the look on her face more than the look on his – she loved it. She stumbled over her words and giggled a little.

Cobra also liked to put his arms around Jonelle’s waist while she cooked, and sometimes nibble her ear. Jonelle always made a play of pushing him off, but she remained coquettish always, and clearly enjoyed the attention. There was never a suggestion of any more than that in my first two years in prison.

As for me, my first experience of physical attention from Cobra was confusing and embarrassing. Dolly had done my hair up exposing my neck, and I was working at my desk on some appeal papers for one of Cobra’s associates. He came up behind me and kissed the back of my neck. Then he lingered there breathing quietly, smelling my hair. My spine tingled and I found myself smiling and feeling yielding – that is the word. I felt as if at that moment I could lie down and be fucked by this man. It should be clear that this was not a homosexual thought. It was the woman in me (perhaps now subsuming the male part) that might be ready to become complete by submitting to a man’s attentions. So when he walked away I felt disappointed, perhaps even a little hurt. Explain that.

The truth was that Cobra was power. He exuded dominance. For all of us “girls” being desired by him on any level, was important. It made us feel important. And it kept us safe.

Because I was so accepting, the gradual changes in me were never unwelcome. After only a few weeks I ceased to get an erection, but that seemed appropriate – girls do not have erections. The growth of my breasts and behind (which I was told was surprising for hormones only) made me physically attractive to Cobra. The effects on my skin and hair made for better hairdressing and facial sessions. And then there were the effects on my mind. In particular after booster injections I was calm and happy, but also emotional and prone to erupt into tears at the slightest thing. When we had booster shots together all of the girls would sit around hugging and sobbing together. It was wonderful.

But there was work to do as well. I found myself increasingly involved in legal matters for Cobra, in particular when he received notice that he was to be charged for some other crimes committed before he arrived in prison, in fact several years before. Evidence appeared circumstantial and witness briefs appeared to clearer than recollection after time would normally permit. There was room to attack the charges, and I took to this work with a vengeance. In the result the witness recollections were compromised and charges were dropped.

I was a successful lawyer for Cobra as well as being one of his prettiest girlfriends.

I had also helped my girlfriends. I had arranged for a review of Dolly’s sentence, based on her being a transsexual. Actually, she was not really a transsexual but we were able to get her the psychiatric certificate to put her on a waiting list for sex change surgery. Following the operation it was certain that she would no longer present a risk as a sexual predator. She was ready to do it. As she put it, she enjoyed her time as a woman, so why not go full time?

Maple also got on the list for SRS upon release, but not to get parole. She wanted to become a woman. Maple had come to regard her penis as a nuisance if not a deformity. We all understood. In fact we got into the habit of talking about or genitals in the female – our “clits” and “pussies”. We even used sanitary pads for no particular reason other than that they were girly. One of us would say: “Honey, I forgot my tampons, could I borrow?” We lived in our own special girly world. It was a happy place.

But what of the other world? I did have some visitors, but with the changes in me old relationships died. I had one old business associate and one ex-girlfriend visit me within the first month. My ex-girlfriend noticed immediately that my eyebrows had been plucked. I didn’t need to explain – her look was enough. Neither she nor the old colleague visited again. My father was still alive but elderly and living in a distant state. He corresponded but could not visit until several months after my imprisonment. To say that he was shocked when he met me as a girl, would be a huge understatement. After that even the letters dropped off, although he did send a card at Christmas. Only my aunt visited regularly. She watched the changes and after a few months started addressing me and writing to me as Tiffany. She looked forward to welcoming me when I was to be released.

And that date finally came. I remember that I had spent weeks preparing for it, but when the time arrived and the guard came to collect me, it was hard to believe. Only the goodbyes would be difficult.

The girls fussed over me, but I saw Cobra standing with his bodyguards, trying to avoid looking at me. I passed between Maple and Sassy and walked towards him.

“Thank you” was all I could say.

“We’re even”, he said. “New charges dropped thanks to your efforts.” Then he put a finger under my chin. “Last day as my bitch”, he said, “I never got to take you. My regret”. I felt there was almost a tear in his eye. Or was that just my vanity?

“Thanks to my efforts you’ll be out in 20 weeks”, I reminded him.

He then surprised me by putting an envelope into my hand. “Do one small job for me and I’ll see you when I get out”, he said. “It’s the missing money from the Valdez job. Find it for me, then look after it until I get out.”

He leaned forward as if to kiss me, but he did not. At that point I wanted to throw my arms around his neck and kiss him passionately, then and there. As if I was a woman. His woman. But I did not. The moment was gone, but that unnatural thought stayed with me, that day, and has ever since.

Up until that moment I had assumed that I would walk out of prison in the clothes I wore in – the suit I wore to court almost two years before. I thought that I would cut of my long hair, and have a doctor sort out my hormones so that I could return to life as before. But that life was gone. I was more than a changed man, I was a new person.

As I walked down the passages through the security gates I found that I was crying. First it was just a tear or two but as we reviewed my personal property I found that I was sobbing. One of the screws (an older guy who I knew was kind hearted) said “Cobra gonna miss you too, Tiffany”. Was he really talking to me?

I picked up the suit but I did not put it on. I walked out of that prison in gingham dress and heels.

Which leads me to where I am now. Alone as it happens. Just a little surprising. Just one person waiting outside prison to collect Cobra Miles when he gets out. It is a warm spring day. The car is ready with top down. I am leaning on it. A sexy pose. Resplendent in my gossamer thin red silk dress. My hair has been carefully soft permed and recolored in a natural looking strawberry blonde to match the season. It has been rinsed in a floral perfume wash. Lipstick matching strawberry color and strawberry flavored too. I am expecting to kiss with it. The dress is short and my legs have been shaven and moisturized.

A bell sounds as a series of gates open and close behind Cobra Miles. He walks across the apron area slowly and manfully. God, he is a good looking man – I had forgotten how good looking. A strong look, now with a smile breaking out. What should I do? No. I won’t run over to him. I’ll wait by the car. But no longer leaning now. Up on my toes willing myself not to run. What will he do? He can have any woman now. He doesn’t need some artificial woman. He’ll accept the lift and then find a real woman. My God, he is so close now I can smell him.

“Hey baby”, he says. And then a strong arm around my waist and his hot breath on my face, his tongue in my mouth. There is no better word for it – I am swooning. His arm is carrying my meagre weight. My arms around his neck. A kiss like no other. And when we part – his eyes into my eyes. Surely this is love.

“Three surprises for you”, I say. “Are you ready?”

In the front seat an envelope with 16 share certificates. I tracked the Valdez money and I invested it wisely - $1,947,624.37. In the back seat I lift a cloth from a hamper. French champagne and a picnic lunch for us to enjoy.

“And the third surprise?” he asks with a smile.

I stand squarely in front of him with legs apart. I take the hem of my short dress in both hands and slowly lift it. I am wearing no panties. He stands back to see. There it is, a neatly shaved pubic area above my freshly healed and lubricated pussy.

“I invested a little of the Valdez money down here and on my chest as well. Do you mind?”

“That, my darling is the best investment you could have made for our future”.

The End

© Maryanne Peters 2017



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