Purty Prison Guard

"I'll take you up on that offer later, after you get more familiar with your body though, for now why don't you let Katie help you learn more about yourself?" she suggested, with her hand stroking my hair on the back of my head.

"Does she want to fuck me too? She's pretty. She can fuck me too," I offered.

"Okay, it's a date, but only if you are a good girl and learn what Katie is going to show you. Do you think that you can do that for your mistress, Horatia?" Mistress Callie asked now staring deeply into my eyes and holding my hand.

"I'll try really hard Mistress Callie," I promised, in the high sweet voice I was hardly aware that I now had.

"That's a good girl Horatia. I have to leave now, so you be nice to Katie while I'm gone," she ordered, with a sweet smile on her face.

As she got up to leave, (I still don't believe I did this), I said, "Can I have a hug before you leave, please?"

"That is so sweet of you. You sure can honey," she hugged me tight, squishing my boobies' way out to the sides as she did.

I started panting like a bitch in heat. Wow! I was, inundated by pleasurable sensations coming from my chest. I really liked how my boobies felt when someone touched them, I almost orgasmed just from her hugging me.

"Oh, so you like that, do you? Well sweetie, I'll be back and hugging you a lot over the next few weeks, so keep that motor running honey," Mistress Callie kissed my cheek and I orgasmed.

Not like... so hard to think... anyway, I came harder than, I think I have ever orgasmed before. Whether I have orgasmed that hard before or not, I want to do it again, a lot.

"Perfect! Everything is working out just as we planned," Mistress Callie announced and then kissed me right on the lips, sending me into another magnificent orgasm, only this time she held it for a couple minutes, I kept squirting and squirting lubrication, until I was sitting in a veritable puddle. She patted my cheek again and ordered, "You be a good little sissy girl for Katie, and I'll come back and kiss you again later." She walked out of my room leaving me with a satisfied smile on my face.

"Well that makes my decision for me, as to what I teach you first," Katie giggled and went on, "bath time is what you need the most now. So let's get you to your feet and into a nice hot and soapy tub full of bubbles."

Katie helped me to my feet, well to my stiletto heels to be more precise. Her strong hands supported me into the bathroom and she placed me onto the water closet, while she filled the tub and squirted bubble bath into the hot water, saying, "While you are there you might as well go sissy, it will be a little while until the tub is full."

I stood and pulled down my pink silk panties, and then sat down again, and let loose the stream of urine from my butt. I wiped my hairless pussy and started to pull off my top in preparation for my bath. Katie came over and helped me get the gossamer fabric over my gigantic breasts.

When the tub was full she supported my, oh so weak, feminine frame all the way into the blissfully relaxing bubble bath. At least it was relaxing until Katie started washing my boobs for me. My legs went straight and rigid, the muscles tightened up so much my legs were shaking. My hands kept grasping the water at the bottom of the tub and I was moaning as if I should be looking for Scrooge.

"I think you are going to need help getting washed, at least for the foreseeable future," she giggled.

I on the other hand could do nothing but twitch.

"Okay, now your mountains are cleaned, why don't you wash your arms and legs," Katie handed me a wash cloth and I automatically took over washing myself as I had been taught by the training tapes.

I ran into trouble when I started to clean my vulva, one touch and I nearly drowned. My back arched hard and my head went underwater as I did. Lucky for me that Katie was there to save me. She pulled my head up into the open air while I orgasmed.

"My, you are easily satisfied sweetie. How about, we wash your hair now Horatia?" she wiped the bubbles off my face, which had covered it.

"Why am I orgasming so much Katie?" I asked her as she supported my head out of the water.

"You are just a horny slut, Horatia. You always have been. It's okay though, everybody is used to it. In fact the girls on the cell block miss you terribly," she giggled, and I was wondering why that would be funny.

Katie showed me how to pat myself dry. Then she powdered me all over, telling me, "I kind of envy you Horatia, not ever having to shave your legs, underarms or pussy. The way you can casually walk around wearing stiletto heels, which are so high that they are nearly ballet boots. You are incredible girl. Your breasts are delightful as well. I wouldn't have the courage to have my breast augmented to the extent that you have," she lightly caressed my nipple, making me quiver all over.

"Do your breasts, make you do this?" I barely managed to ask.

"Not to your degree honey. I love it when mine are, caressed, but I have never orgasmed when someone played with them. You were just made special Horatia, created to be a sex toy," she smiled as she told me this.

"Time to get dressed girl," she informed me. "I'll hold your bra while you step into the cups, and then I'll make up the clasp in back, while you situate your boobs in the cups," she directed, as I did just that.

"You might just have to get some bigger bras soon, this one is almost too small," she told me as she hooked me tightly in the back.

She handed me a crotchless pink thong to pull up my legs, which I did, enjoying the sisterly help she was giving me. She had me pull up rose colored stockings with lace roses woven into them, to attach to the matching garter belt I put on, and then she had to straighten them for me, since it was so hard for me to see them with my huge boobs in the way. Next came a pink see-through silk blouse with elastic woven into the lower half, so that it would cling to my tiny waist, before flaring out to hug my breasts and display them in a deeply scooped neckline.

The silk fabric, hugging me so tightly, and sliding around my torso was sending wave after wave of pleasure signals directly into my brain.

Katie then helped me into a sweet silky pink half-slip, she rested on my wide flaring hips, before slipping up a scarlet silk skirt and fastened it in the back for me.

I was seated before a mirror, Katie helping me to rub conditioners into my face, and then she showed me how to outline my lips with a lip liner, before helping me apply my lipstick.

I found myself wondering why I didn't have to put on blusher or eye shadow until I noticed that I really didn't need it. I already had a violet and pink eye shadow and dark eye liner on, and my cheeks were in a perpetual blush. For that matter I really didn't need the lipstick or lip liner, I had applied the same colors that my big soft lips already were. I think she had me do it to protect my lips from chapping, yes that must be it.

She brushed out my long thick wavy strawberry blonde hair and fastened it into a cute ponytail, which hung midway down my back.

I looked at my tiny slim hands and appraised my nail polish, it was immaculate as always, just the perfect shade of pink and an inch longer than my fingers.

I was smiling at the sight of them when I heard Katie say, "You know you don't have to worry about your fingernails or toenails, Horatia. Remember, Doctor Mannatter replaced your nails with enameled titanium implants, after the accident made you loose a couple nails on each hand, she thinks you are real special and wants you to always be beautiful."

I was grinning broadly, knowing that what she told me must be true, since my nails were so beautiful.

"That should do it Horatia. Now, you and I have an appointment to keep with the warden," she led me through the security areas into the warden's office, where I took a seat across from Mistress Sterndackle, Mistress Callie, and Nurse Goodbody.

"I see you have finally recovered from your accident Horatia. Do you think you are ready to go back into the general prison population again?" Mistress Warden Sterndackle asked me, her hands clasped together on her desk as she leaned closer to me.

I cleared my throat and answered in my sweet, high, little girl's voice, "I feel all better Mistress Warden Sterndackle. I'm sorry to be so much trouble. I can go back in with the other girls again now, and I promise to be a good girl."

Ms. Sterndackle looked at Dr. Callie and said, "Impressive work Dr. Callie. You are, sure that she can perform her trustee duties now? The duties that we discussed earlier?"

"Most assuredly warden, I will personally acquaint her with her new position as a trustee," she replied with a devilish grin, knowing what awaited me.

"Excellent, make sure I get copies of the first day's training films. You may take your charge to her cell again and begin. I'll finish up the paperwork transferring her back to her cell," Mistress Sterndackle told her, picking up a sheaf of papers and glancing at them. Then she whispered to Dr. Callie, "Harry's sister, who works for the county records department, has filed the fake records for Horatia. She is now officially here on repeat offender charges of prostitution. Many, many charges of prostitution," she snickered deviously.

"Perfect," Mistress Callie and Katie stood, took my tiny hands, and led me back to my special pink cell.

Right away, I noticed they had redecorated. There was a new King size bed with pretty pink sheets and a ruffled pink comforter on it. All of the plain curtains had been, replaced with ornate pink hanging draperies. There was a new cabinet against one wall. The bathroom now has a big mirror. They replaced the small shower with a huge bathtub and shower, in pink. There was a walk-in closet filled with pretty, pink clothes and lingerie, even a section with latex outfits hanging there. My pink dresser was double the size it was when I last saw it, I opened the drawer and saw scads of lingerie. There were different colors and styles aplenty and none of them looked at all like ordinary daywear, it all seemed to be out of Victoria's Secret or Fredericks of Hollywood.

I walked over and bounced onto my back on the bed and only then did I notice the huge mirror on the ceiling.

"Beautiful isn't it Horatia?" Mistress Callie asked, as she had been watching me look around from the doorway with Katie.

"It's wonderful!" I squealed enthusiastically.

"Well, not everyone has a nice cell like this one Horatia, and if you want to keep this one, you have to work for it. You do want to keep it, don't you?"

"Oh yes," I replied.

She closed the cell door and began stripping off her clothes, as did nurse Katie. I was confused and started to remove mine as well when Mistress Callie said, "Stop! We will do that ourselves in a minute."

They both walked into the closet and when they emerged, Mistress Callie was wearing thigh-high black leather, high-heel boots, a leather thong, and a leather shelf bra, which left her nipples exposed.

Katie was wearing a soft, frilly baby doll with a leather collar that had a leash attached, and the other end firmly in the grasp of Mistress Callie, "That's more like it. Now my lovely slave girl Katie, I want you to prepare our special guest."

Katie came toward me with an evil grin on her face.

I was so frightened I began to tremble all over, which made Mistress Callie laugh evilly.

Katie veered off toward the new cabinet, opened it, and brought out some restraints, which she promptly affixed to my wrists and ankles. I knew that both women were bigger than I am and that the crop that Mistress Callie had would be able to quickly subdue me, so I didn't resist.

Katie laid me down on the bed and tied me to the four corners. My legs were, spread wide and painfully. Katie then put a tight collar onto my neck with a small box attached to it.

"The collar you have on will emit a painful shock if you cry out or start saying inappropriate things. Do you understand Horatia?" Mistress Callie told me holding the remote control in her hand.

"Yes," I replied.

ZAP!

"That is, 'Yes, Mistress Callie!' Don't forget it. Note also that what you just felt was the lowest shock level. I have four higher levels. Now say it again properly WHORE," she yelled.

"Yes, Mistress Callie."

"First lesson learned. That is good Hor, you don't mind me nicknaming you Hor, do you?" she demanded, hand on her hip, the other firmly hovering over a button on the remote.

"N... No, Mistress Callie," I hesitantly replied, afraid to be shocked again.

"Good, because that is your new job, Hor. You are the prison whore. You will be trained on how to please a woman in many ways, and will become proficient in all of them, since you will be having so much practice," she turned to face Katie, "Make her ready Katie."

Katie splayed opened my blouse and scooped my breasts out of my bra, leaving then standing high on my tiny chest. She hiked my skirt up around my waist, and then cut my panties off me.

"She is helpless and ready Mistress Callie," Katie stated, taking her place standing behind and to the left of her mistress.

"Key phrase, Harry Ass Buttman," mistress Callie stated with a smirk on her face.

Suddenly the haze in my mind lifted and again I was 'the me', that I should be, "What in the fuck is going on! Where in the hell did these fake boobs come from and why am I tied to this bed?"

"Those are not fake boobs Harry, those are your tits. You are tied to the bed to begin your training as the prison whore," she left it at that, and just stood there smiling.

"Gigolo maybe, but only girls are whores, and I'd have willingly fucked as many of the inmates that you want me to, without having to be tied down," I replied.

"Katie, go ahead and start tongue fucking her," Callie ordered.

I could feel the bed bounce while she climbed on, especially since my enormous boobs jiggled all over, sending strange sensations all through me.

The next sensations were unbelievable, she spit on my crotch, and I felt it run down... the crease in my crotch? Before I could come to grips with that, she gently spread my vulva with her slippery tongue. I was unprepared for the intense pleasure her tongue was inflicting on me. My head went back into the pillow hard, my toes curled up and I started trying to buck my hips into Katie's face.

Mistress Callie grabbed my hair and pulled my head around so that my eyes opened to see her face closely, "Harry, you are now a woman. You have a uterus, a vagina, and ovaries. Unlike most women though, you have six ovaries, I wanted to make sure that if any were, rejected, you would still have functioning ones. You have three clits, in a cute triangle configuration in the top of your vulva. I gave you a sixteen- inch long vagina, which will accommodate an enormous dildo. You have flexible labia that will stay tight on whatever penetrates you but will still stretch around huge objects. You have six Bartholin's glands, which will make you just the juiciest fuck around, and guarantee that you orgasm buckets of pussy juice. I made sure that those udders on your chest are incredibly sensitive with enormous nipples so that they will send you into quivering submission easily. Each normal woman's breast has 15 to 20 sections, called lobes, you however have sixty per breast, so when I say udder, I really mean that. I removed five of your lower ribs, and shrunk you in almost all directions. Your waist is a tiny eighteen inches. You are almost five feet tall on your toes, which by the way is the only way you can walk anymore. I spread your hips nice and wide, around thirty nine inches. I'm sure that you have noticed that you sound like a six year old when you talk, and I made sure that you're ravishingly beautiful," she laughed long and wildly.

"You look like you don't believe me Harry. I'll prove it, look straight up, and watch as Katie makes you cum in a wonderful, gushing, feminine orgasm," she pointed my face toward the ceiling mirrors.

I saw a sweetly beautiful, tiny, strawberry-blonde girl with her head held firmly by Mistress Callie, staring back at me, buried by a pair of huge boobs and a pretty blonde with her tongue driven deeply up a hairless cunt, attached to the little booby girl.

"Noooo!" I screamed, "Please tell me it's a joke! I... I... I can't be a girl! No one can give a man a cunt that works. It's not possible. You have to be lying," I ranted, Katie licked the three clits in my soft sensitive labia, as she was rapidly bringing me towards orgasming.

When I did orgasm, it was like having an epileptic fit. I thrashed about, bucked, arched, clenched, and gushed a small tidal wave out of my pussy.

Katie didn't stop though, she had me thrashing about three more times in the space of a few minutes, one multiple orgasm after another.

Finally, Mistress Callie told her to stop, whereupon she came around and kissed me. That didn't shock me as much as her sharing a mouth full of my own pussy juice with me, which I had to swallow, or drown.

"It's time for Harry's 'Lady Viagra TM' shot Katie, so please administer it to her, and then inject the oxytocin, I want her to become extremely feminine mentally, so getting her breasts to lactate should help her to be more nurturing," she watched as Katie shot a huge syringe of 'Lady Viagra TM' into my butt.

Katy turned to a table and filled another huge syringe and injected both of my boobies with half it's content.

"You see Harry, you are going to be more of a woman than even Katie here. You should start to menstruate in two weeks. You had better be a good girl or the warden has promised that she will send a male guard in here to fuck you at the proper time, to insure that you are pregnant. Won't that be fun," she giggled at the look of terror on my face.

"Don't worry I'll help you in that area, I'm going to restart your conditioning so that you will be a proper whore, right up to the point when you are so close to the throws of ecstasy that you can't stop. Then and only then, will you be able to remember that you are Harry Buttman, ex-prison guard, rapist, and drug pusher. Oh, and the other leash we have, is your addiction, if you are not a good little slut-whore, we won't give you your maintenance dose of morphine. The withdrawals are impressive to watch, and I'm sure that you will do anything we ask to get your drugs. How do you like being a drug addict whore Harry?" she patted my cheek painfully.

"You Fucking b..." I started.

ZAP!

The pain overwhelmed me, and my jaw clenched.

"Pain and pleasure, I'm sure you will find it an effective combination," she caressed my huge breast sending shivering waves of pleasure to my brain.

"After a few years of our loving ministrations, even the slight remnant of Harry that is left now, will be so thoroughly immersed in Horatia, he'll love what she has become... Harry Buttman, prison whore," she laughed then spoke the key phrase that mentally turned me into a submissive girl.

********************

"Hor, it's time for your next appointment," she announced, as she led into the room a prisoner that I had blackmailed into having sex with me many months before.

"That's really him?" she asked incredulously, her hand covering her mouth.

Mistress Callie gave her a stern look.

"S... Sorry, her... She is lovely! I dressed up. How do I look?" she twirled slowly so that we could see her dress.

She was wearing a chiffon pastel print dress, wispy and gossamer looking, with suntan pantyhose and white sandals.

Mistress Callie replied, "Quite lovely my dear. Hor is prepared, just as you requested. Katie, please go and pick out an appropriate collar for Lillie."

Katie undulated off to the closet, returning with a pastel blue collar that she strapped to Lillie's neck, handing the leash to Mistress Callie.