Purty Prison Guard

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Wholemanz
Wholemanz
213 Followers

I blushed, "Do you really think so Darlene or are you just saying that?"

"Hor, I have always suspected that the warden was gay, but that is the first time she ever showed that she likes girls, or she wouldn't have kissed you," she told me squeezing my butt, sending stimulating sensations to all of my nether regions.

"So Horatia, are you going to leave us? Head out into the big world and try to make it as a woman?" Darlene looked down at me and asked.

"I think so Darlene, who knows maybe I can find someone who can undo all of what was done to me," I told her not realizing that what I hoped for was even more impossible than what had been, done to me.

When we got back to the cell, Darlene milked me, gave me a clean pair of pink panties, and then tearfully kissed me goodbye.

I headed out toward the main gate, but had to pass by the male guard's ready room, which had a guard present at all times, but as I passed, my feet wouldn't move in the right direction. I found myself detouring into the ready room.

The guard there saw my huge boobs, my pretty face, my outrageous high heels, stupendous figure, he immediately came to attention, and then he stood up.

I couldn't take my eyes of the bulge in his pants. I walked right up to him, unzipped his pants, took his rigid tool out, and knelt down in front of him and gave him a blowjob that almost took the top of his head off.

After he filled my mouth to overflowing with his sperm, and I had swallowed it down like ambrosia, I could finally control my body again.

I fled back to the only haven I knew... my cell and Darlene, retching three or four times along the way, leaving a trail of bile behind me.

When I made it to the cell Darlene was waiting for me. She cleaned me up, gave me a shot to settle me down, and held me while I cried, and started the dry heaves.

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

In the morning, I awoke still in her arms and even when I started bawling again, she comforted me.

After our usual lez workout, even the deep throating of the dildo, she lay with me.

"Darlene, why did I do that, and why didn't you warn me?" I asked in my tiny little sissy voice, timidly.

"I'm sorry sweetie, the warden and the doctor wanted you to know what you would be doing if you ever left this place. They felt it would make a more lasting impression if you actually experienced it. I had no choice, being as much a prisoner as you are, they threatened to take you away from me if I didn't cooperate, and then you wouldn't have anyone to comfort you when you returned," she admitted squeezing me tightly.

"So what you are saying is that if I ever leave here, I'll be sucking a lot of cocks, right?" I verified, realizing the diabolical nature of my prison.

"The other thing I need to remind you now is that you are a morphine addict. If you had managed to make it outside, you would have been in withdrawals within twelve hours, and probably in a hospital shortly thereafter. They felt it only fair, since you were making addicts within the prison, that you become one too. Therefore, you are in more that one prison, Horatia. You are in the prison of your body, the women's prison, and the prison of your mind, and unless your sexual orientation has changed or unless you were already a closet bi-sexual, which I know you are not, living within a community of all women is your only refuge."

"If you will let me, I promise to make your prison stay as pleasant as I can. You also have other admirers here that want nothing more than to please you and fulfill you fondest wish, to have as much sex with women as you can in one lifetime. It will be as a woman, but you are going to enjoy sex more that any woman that ever lived, the warden insisted on that, when this plan was put into motion, almost a year ago," she kissed and hugged me, even though I was still trembling violently.

"There is someone in my room next door that wants to spend some time with you if you will let her," she asked, as she stood and walked towards the adjoining door. "Shall I let her in?"

I didn't want to be alone, so I nodded my pretty little head.

In walked Katie Goodbody, the nurse who had befriended me during my surgeries. Only now, she was a much larger girl. At least her boobs were.

She ran over to me and embraced me, squishing our huge chests together, "Horatia, I'm happy to see you."

"What... wh... Your boobs," was all I managed.

"I loved your boobs so much I convinced Dr. Callie to make mine just like yours. It took her longer to find compatible donors, but she finally did it. Do you like them Horatia?" she stood and pulled her top over her head and bounce up and down to display them for me.

She grasped a nipple and thrust it in my mouth, "Taste me."

I started to suck reflexively, being rewarded right away, with a mouthful of milk, a deep moan from Katie, and a spreading wet spot underneath me.

Darlene whispered in my ear, "Will being a sex toy for hundreds of women be so bad... even if you do have to have boobs and a pussy to do it? I know two hot babes who want you to stay, and fuck their brains out."

Katie added, "So, baby will you please stay and have sex with us?"

I would have gone insane if two women had pleaded with me to have sex with them like that when I was a man.

When Darlene started finger banging me I nearly did go insane... with orgasmic pleasure. However, I retained enough mental presence to deal, "Just promise me I never have to face fuck another male guard ever again, and I'm all yours!"

The End

(At least until Dr. Callie is, released that is)

* * * * *

Purty Prison Guard (Version 1.2)

By Wholeman

Everything else is Copyright (c) 2003, by: Stone on the Moor LTD. Freely archived, copied, transmitted, and redistributed, printed, fantasized about or masturbated to or used to perpetuate marital bliss. (Just don't tell her you read this stuff)

Wholemanz
Wholemanz
213 Followers
1...345678
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
3 Comments
AnonymousAnonymousover 19 years ago
great story, but (s)he needs more punishment

I liked it very much--creative and sexy and weird. I was thinking that what they did to her would have been more like punishment if they had mostly denied her desire to be with women and forced her to suck cocks and get fucked by them, all the time feeling the disgust that her Harry persona would have felt at so doing.

DFWDOMDFWDOMover 19 years ago
The good, the bad and the ugly

The story is great, but there were so many errors that I started noticing them instead of the story. Needs to be cleaned up.

Colleen ThomasColleen Thomasover 19 years ago
Interesting read

Not exactly my usual fare, but it's been a sleepless night and this story has kept me company for a while. The descriptive prose is strong and in places very well done. Dialogue flows well. Good plotline, well defined characters.

Although not what I usually read, throughly enjoyable.

-Colly

Share this Story

Similar Stories

Revenge of the Nerd: Bitch Sister Nerd uses formula to make his sister his submissive slut.in Mind Control
Be Careful What You Wish For Larissa sells her soul and gets more than she bargained for.in Transgender & Crossdressers
A Big Side Effect A girl's medicine causes a strange...growth. And urges.in Transgender & Crossdressers
Goddess Rhiannon Goddess protects abused boy and punishes father.in Transgender & Crossdressers
Tanks For The Mammaries He is being executed for a murder he did not commit.in Transgender & Crossdressers
More Stories