Purty Prison Guard

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Wholemanz
Wholemanz
214 Followers

"On the bed now my pretties," the two women hopped onto the bed with me, one on each side, as Mistress Callie ordered. "Now, as sexily as you both can, strip one another."

Katie and Lillie started kissing and slowly undoing each other's clothing, right over my tightly bound female body. As things proceeded, the sight of them stripping was making me crazy, but when they started brushing against my boobs and tiny little body, they had my cunt drooling like one a Pavlov's dogs.

"Use your discarded clothing to tantalize our victim," Mistress Callie ordered, having taken a seat across the room and began rubbing her own crotch as she watched.

Katie placed her D cup bra on top of my much larger breasts, rubbing my nipples through the lacy fabric, and tickling the sides of my mountainous mammaries with the straps.

Lillie took her silky panties and rubbed my face with them, and then moved them down around my breasts and tickled me all the way to my toes and back upwards to my vulva, where she concentrated on driving me wild, slipping them between my legs, and sometimes my labia.

I was so, turned on that I was trembling all over, straining at my bonds, and moaning loudly.

"Very good girls. Lillie, I believe that our little Hor here would like to have sex with you. I think, since she was always looking for some pussy, you should feed her yours," Mistress Callie snickered, and started pulling at her own nipples. "Katie, I want you to use your fingers on Hor's cunt. Go slowly and teasingly, and not more than one finger in her at a time."

Lillie straddled my face and brought her sweet smelling pussy down on my mouth. I was, so crazy with sexual energy I willingly began tongue fucking her. She was moaning and caressing my boobs. With every lick, she would reciprocate by twiddling my nipples and moaning herself.

With Katie finger fucking me with maddening slowness, even so, I screamed an orgasm into Lillie's vagina, well before I brought her to her own trembling, face dowsing, orgasm. I swallowed at least two mouthfuls of her pussy juice before she lifted off my face allowing me to breathe freer.

"Wonderful Lillie, now you know what to do next. Katie, you now have boob, and face duty. I want to see her lips trembling, before Lillie returns," Mistress Callie ordered, with a steamy satisfied look upon her face.

Katie nibbled my ear, nuzzled my boobs, twisted my nipples, and then she stuck her tongue down my neck, tickling my tonsils. She started licking between my breasts, and sure enough, my lips were trembling in no time.

"Ah, you're back, Lillie. Crawl into position," Mistress Callie ordered and I felt the mattress move with her presence, jiggling my massive breasts, "You may begin when ready."

I felt Lillie's fingers play with my labia, smearing my pussy juice all over and next... Oh GOD NO! I felt a hard blunt object sliding up and down between my lips. I flexed my pussy muscles trying to deny entry to the invader, but I was way too wet and didn't have enough strength in my cunt muscles to deny its entry.

I felt my lips stretch around the invader and my resistance dwindle rapidly. It felt... it felt like... I felt... well... whole, is the only way to describe it. The invader plugged the vacancy between my legs and I wanted more of it. I wanted her to ram that thing into me to the hilt, and when she started backing out, I clenched my muscles in an effort to keep it within me. I had no reason to worry, since she started another stroke before she came out. I tried to grab hold of her, tried to cling to her, but my bonds were preventing that, so I concentrated on kissing Katie whenever she was near my mouth.

I orgasmed in a torrent, loudly screaming, "Oh god... oh GOD... OH GOD!"

"Keep going Lillie," Mistress Callie ordered then she stood up and walked over to the head of the bed, bending over so that she was close to my ear and face. "Hor, do you like being fucked? Do you enjoy being, filled by that big dildo? Tell me that you want to be fucked. Tell me you want to be fucked a lot."

"Oohgloo," I replied to her demand, my mind lost in the incredible ecstasy I was experiencing.

Mistress Callie held her hand up to Lillie indicating she should stop, "Hor, now I want you to say, 'fuck me. Make me your whore. Fuck me hard, please!' If you don't, I won't let her continue."

I wanted more. I wanted her to keep going, I needed her to keep going.

I was taking too much time, so Mistress Callie waved Lillie to start backing out of me.

"Nooooo! Fuck me. Make me your whore. Fuck me hard, please!" I screamed, trying to scoot my butt toward the retreating dildo.

Mistress Callie signaled for Lillie, to start stroking forward again, "That's better Hor. Lillie needs to know that she's, appreciated. She needs to hear you ask her, to fuck you. So now, every time you stop asking, she will stop fucking."

Now she wants me to beg to be fucked... but it feels so... I don't want to say it, but I need it! I started quietly saying, "Please fuck me Lillie. Please keep fucking me. Fuck me Lillie! Fuck me... Fuck me... Fuck me... Fuck me...Fuck me, fuck me, fuck me, fuck me," I kept screaming louder and louder, until, "Oh god... oh God... OH GOD!"

"I think it's Katie's turn to fuck our little whore," Mistress Callie announced loudly at my side.

Katie donned the strap-on and Lillie started work on my boobs and head.

"Don't forget to encourage Katie, my little whore, she likes to have a cheerleader. It's easier to hurt her feelings though, if you stop begging, she pulls out and goes home," Mistress Callie whispered into my ear.

"Oh beautiful Katie, please fuck me. Please fuck me hard," and so on... until I came in another mind numbing torrent. By then I was sitting in a puddle of my own vaginal fluids, the sheets soaked all the way up to my shoulder blades, but I didn't care.

I was exhausted, but reveling in the afterglow of all the sex.

Mistress Callie had the girls untie me and change the sheet underneath of me, and then she left, having Katie and Lillie sleep next to me, cuddling.

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

I awoke in a bathtub full of bubbles, with Katie and Lillie washing me all over using plenty of soap. My breasts and vagina as well were being, washed. I had never even heard of a penis shaped sponge, until I had one used to clean out my pussy, especially not one with a tube up the center that douched me out as those wicked women made me orgasm into our bath water, and of course, I'd pleaded to be fucked throughout the whole thing.

When I got out of the tub and they dried me off, Lillie, jabbed a syringe into my left breast and deposited half the contents in the syringe there, then she put the rest in my right breast. While I was recovering from that, Katie jabbed a syringe full of something in my left butt cheek, I grabbed to rub the spot and felt her nail my other cheek with a shot. A warm soft feeling enveloped me and I smiled.

"I know that you don't really care right now Hor, but you just received your Morphine, oxytocin, estrogen, Prozac, and Lady Viagra TM cocktail shot," she kissed my cheek, making my knees tremble.

They dressed me afterwards in a pink leotard and tights, which clung to me like a second skin and showed off my vulva quite dramatically through the thin fabric (Due partly to the fact they pushed the seam up between my labia.). Whereupon I was, escorted to an aerobics class, led by Mistress Callie, and by the two women who had a leash attached to my collar on each side, with me also wearing handcuffs and hobbles.

It's not as if I could put up much of a fight, without the boobs I couldn't weigh more than 90 lbs. If I thought I was small before, now I'm a waif. I have, pipe stem arms, thin legs, hardly no waist, and they tell me that I was bed ridden for six month after my last accident. These trustees were going overboard with the security for me. Heck, with the stiletto heals they make me wear I can't even walk at a normal pace, let alone run. I'm just a weak little girl after all.

How do they expect me to do aerobics with these shoes on?

When we entered the room, I saw that there were already thirty or so women present, all of who were dressed somewhat as I am. The ladies escorted me to the wall where a bench sat, amid the giggles and titters, of the other students. They removed my leash, hobbles, and handcuffs, and then proceeded to take off my high heels, which they were replacing with high heel wedge/sneakers.

"Do I have to wear high heels? Can't I just go barefoot?" I whined.

Mistress Callie heard me and came over with an evil smile on her face, "Lillie, Katie, I think we need to educate little Hor here..." she was standing with her hands on her hips watching us, "leave the shoes aside for a bit."

They did as they were, told.

"Alright now Hor, I want you to wiggle your toes for me," she smiled as I did so, "now wiggle your feet up and down," which I did as well, "see girls, they feel quite normal to her, but you saw how her feet move?"

The two ladies nodded that they had.

"Perfectly designed to function as well as they do in the designated footwear. Now help Hor to her feet, so that she may walk around barefoot for us," she instructed, with more than just a hint of sarcasm in her voice.

My two escorts helped me to my feet, but my feet wouldn't work right. When I relaxed my calves all the way, my feet were still, pointed down in almost an 80-degree angle, my heels, far from contacting the mat we were standing on.

"Now Hor, up on your tippy toes," Mistress Callie ordered, motioning with her hand as well.

I went up as she ordered, and my feet reacted easily and not only could I support myself on point, but I could see in the mirror along the wall of the exorcise room that my feet were actually even pointed backwards a little.

"Now I want you to walk with me around the room once to show all of the other women your pretty little feetsies," she said in a little girl cutesy voice, and then giggled. She walked along the wall around to the front of the class, with me trailing like a puppy.

When we came to the front of the class Mistress Callie announced, "Class I want you all to meet Hor, short for Horatia. On the other hand, if you prefer you may spell it 'w h o r e', she won't mind. She is walking around the room on-point to show you all her pretty little feet, so I want you all to take a good look. You may comment if you like, she appreciates knowing how you all feel about her appearance. She has had quite a few surgical alterations to her body to make her more attractive, to either sex. She loves sex, and she loves to be fucked, by anyone," she said, concluding my introduction.

"Go ahead Hor, I want you to walk up and down between each aisle. Stay to talk with each of the women as long as they want you to. Don't be rude to any of them or you will be, punished. I want you to let them do anything to you that they want while you get to know them," she snickered evilly, followed by a chorus of more than thirty other giggles.

I seemed to know all of the women, but for the life of me, I couldn't remember a thing about them, all I know is that for some reason looking at them was making me incredibly horny. I was sure that my pussy had soaked the crotch of my leotard by this time (I couldn't see it over my boobs.).

(Out of my hearing, Katie was telling Dr. Callie, "She has so much Lady Viagra TM coursing through her veins I am surprised that she hasn't thrown the whole class to the mat and started fucking them to death," she snickered quietly, along with the Mistress. Then she said, "Three times the maximum dosage... we better keep an eye on the guard dogs.")

I started with the first woman on the left of the classroom as I easily, and quite sexily undulated over to her. As soon as I was close enough, she grinned broadly and grabbed my cunt. I was shocked but I knew that the Mistress would punish me horribly if I did the wrong thing, so I merely moaned as the pleasure exploded in my mind.

"Wow, you are a horny slut, honey," she announced to the whole class, "She's soaked her tights and leotard all the way to her knees." - Giggle-

"Go on and let the next lady have a feel, Hor," she waved me on to the next student.

I walked up to the tiny red head that was, glaring at me.

She reached out and lifted my enormous boobs, and then let them drop and jiggle, while I tottered trying not to fall over, "Well it's a start. Maybe I'll feel better about it in a couple months. Get on with you Hor."

When I walked up to the next lady, a blonde with an impressive rack of her own, I stopped, she went to her knees and started caressing my feet.

Who would have thought that those tiny feet could make a girl so hot? She said loudly, "I can't wait for my turn. These are all mine."

She had me panting like a bitch in heat with what she was doing. How could my feet be making me so hot?

She finished and stood, but not without sliding her hand up my legs and cupping my vulva, while saying, "You loved sex, and now you are sex!" -giggle-

She sent me to the next woman in line who simply planted a lip lock on me that left me gasping for air.

It went basically the same way, woman after woman, by the end of the line I had orgasmed five times, my feet were soaked with my own cunt juice, and there was a dark wet stain all the way up my leotard to within six inches of my neck.

I was relieved that my ordeal was over with, when I heard, "You naughty women! The whole bunch of you got poor Hor all worked up now. The whole class must be, punished. Since you all got her so horny, I think it only fitting that you all fuck her brains out."

My tired eyes flung themselves open in terror! My knees went weak and two of the ladies caught me on my way to the mat.

Dozens of women pounced on me stripping my tiny trembling body like piranha attacking a swimmer. Someone poured a gallon of baby oil all over me and within moments, naked, squirming women covered me using hands, mouths, tongues, and toys on me. I have no idea how long they fucked me. It was at least two or three hours. I lost track of how many times I orgasmed, and I remember Katie and Lillie giving me another series of shots partway through it, making me crazier for sex than you could ever imagine. Those women fucking me insatiably drove me into having ever more sex, no matter how sore my cunt was becoming, just as long as I kept orgasming.

I awoke to hear, "I don't care what she did. I really like her. Can I help you take care of her?" The cute six foot tall blonde was cradling my head in her lap as she pleaded with Mistress Callie.

"We can discuss that privately Darlene, especially since Hor is awake again. Darlene will you slip her gym shoes on her so she can be taken back to her cell?" Mistress Callie asked bringing the gym shoes over to her.

"My pleasure Doc, I'll even help take her to her cell if you don't mind?" she gently laid my head onto the mat and crawled to my feet, lifting them and fitting my comfy sneakers on them. "How does that feel, Horatia?"

I immediately fell in love with her. She was the only one to call me by my real name. I think it's my real name...? Anyway, she was nice to me when everyone else seemed to just want to use me.

"Thank you very much ma'am," I told her with as much feeling as I could put into it, while still being respectful.

She picked me up off the mat as if I weighed nothing at all, sending my naked boobies jiggling and undulating every which way.

"Damn, those things fascinate the hell out of me sweetie," she confided.

Since she seemed to be deficient in the booby department, I could understand her fascination so I said, "They're yours anytime you want to use them."

"My, that's sweet of you to offer sugar," she kissed my little cheek.

Mistress Callie cleared her throat to get Darlene's attention, "Darlene please set Hor back down on her feet so that she can be properly bound for her trip back home."

"Heck Doc, with me along she ain't going anywhere. This little lady can hardly walk at all, and I can run the hundred as if my ass was on fire, when I have to. I'll keep an eye on her so she doesn't overpower anybody and run away, he, he, he, as if she could! One titty twister and you'd about kill this one," she joked, as she placed me back upright on my feet.

Mistress Callie gave her an extremely annoyed look.

"It's alright ma'am, I don't want to make any trouble. Please put the restraints on me, as Mistress Callie asked," I didn't like the look Mistress Callie was giving Darlene, and I didn't want my new friend to be in any hot water on my account.

"I'll do it if Doc here agrees to let me come with you..." she proposed.

My eyes must have screamed out my fear because she held me tightly to her, "Don't you fret hon.. I'm here and there's nothing to be afraid of."

Mistress Callie looked up towards the ceiling as if to ask for help, then replied, "Darlene, you may come along, but we are really going to have to have a long discussion later, agreed?"

"Sure thing Doc, hand me those handcuffs and I'll get started," she asked in her simple, straightforward way.

I was quickly, cuffed, hobbled, and we started back on our way to my cell. Of course I was still naked and cum covered, but we didn't get near as many cat calls, whistles, or nasty comments as I expected, apparently Darlene has a few menacing looks of her own.

Mistress Callie was not very happy when we entered my cell, but she held her tongue while Darlene was there.

Darlene removed my hobbles, handcuffs, and sweetly kissed the inside part of my wrist. When she was finished, she looked questioningly at Doctor Callie and waited for her to speak.

"Thank you Darlene, Hor has a date now so we will talk later..." she tried to dismiss the large woman.

"Uh Doc, before I go let's you and me have a little discussion outside," Darlene insisted, motioning her to come with her as she left the cell.

I couldn't hear what they said as I sat on the side of my bed and waited.

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

Outside the cell, a brief and slightly heated discussion was occurring.

"I know that is Harry you have in there, Doc. I also know that she doesn't know that she is Harry as she is, isn't that right?" Darlene started, her fists on her hips looking down at the much smaller woman.

Doctor Callie, somewhat exasperated with the other woman, replied, "Yes, Darlene, she does not know at this particular time that she is Harry, but with what we are doing that is necessary. If he knew he was Harry, she would be fighting tooth and nail every minute, which would make what she must learn more difficult for all of us."

"The way I look at it Doc, she is a girl, she is going to need a friend that she can cry in front of and do all that girly stuff, without worrying about being betrayed. So if you really want her turned into a girl, and a soft submissive one that must rely on all the feminine ways that you want her to have, why don't you let her use me as a crutch, and she will never be able to function without a strong protector?" Darlene grinned wickedly at the doctor, showing a heretofore intensely intelligent gleam in her eye, the doctor was shocked to discover.

"That is a good idea, we'll talk more after dinner tonight," she agreed, "I'll have the trustees bring you to the wardens office and we can work out the details."

"Great Doc, I want that piece of shit to be the most simpering, spineless excuse for a woman that has ever walked the Earth," she concluded vehemently.

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

When the doctor returned to the room, she met only Horatia and Katie inside. Lillie had gone back to her cell.

"Well now Hor, it's time you cleaned up and dressed for your next date, so into the bath with you. Katie, go with her and make sure that she does not ruin my good repair work by falling down in the bath tub," she instructed.

Wholemanz
Wholemanz
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