(Re-edited version of a story from the archives)
Jenny had been visiting her boyfriend in prison for the past two months. He’d been convicted of drug possession and was serving his penance in an upstate prison. It had been a long haul for both of them. Even though he was due to be released in three days, Jenny just couldn’t stay away until then. She made the three-hour drive to the prison, just as she had every Saturday. They weren’t given any privacy during their meetings, but they were allowed to hold hands.
“I really miss you,” Jenny said, as she rose from the chair.
“Only three more days, baby.” Her boyfriend smiled, releasing her hand.
Jenny watched as the guard escorted him back to his cell block. She couldn’t wait to feel his touch again, his hands running through her curls as he kissed her. It was all she thought about as she exited the visitors’ area.
Jenny stopped to use the ladies’ room on the way out, not thinking she could make it back home without going, despite her anxiety over public restrooms. She carefully laid toilet paper over the seat and closed the stall door, lowering her jeans and panties.
Just as she was finishing, she heard a commotion outside the bathroom. The outside door to the restroom swung open, the bells and buzzers fading into the background as the door swung closed again. There was someone in the restroom with her, obviously out of breath, their panting growing louder. Jenny reached up to lock the door, but it was too late, the door catching her fingers as it swung into her. A woman in an orange prison jumpsuit eyed her intently, she was sweaty and wild-looking.
“This is soooo perfect!” Said the prisoner. “We could be twins”
The incredible likeness wasn’t lost on Jenny. As jenny tried to squeeze around the woman, she was pushed roughly backward, landing on the toilet with a huff.
“Take off your clothes, quick!” The woman revealed a homemade knife and held it out to Jenny’s face. “QUICKLY!!”
Jenny jumped off the toilet, whipping off her jeans and panties, which were still around her knees. “Everything! Hurry up, I don’t want to cut you, but I will!”
In no time at all, Jenny was standing completely naked. She watched as the woman slipped out of her jumpsuit and into Jenny’s clothes. She grabbed Jenny’s purse from her hands and casually walked out the bathroom door, leaving Jenny naked and shaking.
Not knowing what else to do, and not wanting to be seen naked she hesitantly slipped on the jumpsuit. Just as she was about to push through the door it flew open, a flurry of hands grabbing her roughly and whisking down the hall.
Everything was a blur as Jenny was dragged past door after door with a lot of banging and crashing. Tears wear streaming down her face at this point, but nobody seemed to care. She realized that the top of the orange jumpsuit was torn open, and her breasts were flopping in and out of the hole. Only a few seconds later she was thrown into the darkness, a steel door slamming behind her.
Jenny was in a dingy little room with a single cot and a metal toilet. It smelled awful and the only light seeped through the small window in the door. Jenny realized what had just happened and started to weep. How was she ever going to convince these people that she was not their prisoner? Jenny’s virtual twin was probably long gone by now.
She heard keys rattling in the lock and the door swung open. A short matronly-looking woman stepped into the cell and closed the door behind her. There was another woman standing behind her with a baton pulled.
“Stein? How many times are we going to have to do this? You know you can’t get out of here.” The woman seemed more disappointed than angry. “Ok, Sweetcheeks, you know the drill. Loose ‘em.”
“Maam, please there’s been a mistake, I’m not th…”
“Look, Stein. I have five other prisoners to deal with, now take ‘em off.” Jenny couldn’t believe she was being forcibly stripped for the second time in an hour. She removed the jumpsuit sobbing. “Get over it, Stein. You’ll be back in general circulation in three days. You goin’ soft or something?” The woman grabbed the jumpsuit from Jenny’s arms as she walked towards the door. “By the way, we found your socks and shoes in the restroom where we caught you.” She snickered “They’ll be in your cell waiting for you.”
The door slammed shut again and with the rattle of a few keys, the silence descended. Naked and cold, Jenny sat and pondered her situation. She laid on the filthy cot and cried for hours. Every once in a while the room darkened, and she could see a face peering through the window in the door. There was nothing to cover herself with and she knew that all the male guards were amusing themselves gawking at her nakedness.
The three days passed slowly for Jenny. She was either crying or pacing for almost all of it. Jenny hadn’t eaten anything that had been slipped through the slot in the door. She knew she must look hideous. She also knew that her boyfriend was being released today. There would be no happy reunion, no first night in the sack. Nothing. She was apparently ‘Stein’, whoever she was. She didn’t even know what crimes this person had committed, or what her sentence was.
“Oh, God!” She thought, “What if she’s a murderer?” Jenny began to weep again, but just as she did the door opened and the matronly woman appeared.
“Ok, Stein, out you go.” Jenny had been naked for three days and it seemed to slip her mind as she walked out into the hallway naked. “I was about to give you your jumper, Stein, but we can do it this way if you want.” She threw the jumpsuit to the other guard and led Jenny down the hallway, passing a lot of guards and other prisoners as they went.
Jenny knew it was futile to argue with these people. They had her. She was taken to a shower room and told to shower down because she smelled bad. The lukewarm shower felt good and stronger than hers at home, the jets stinging just a little.
“Okay, Stein, spread ‘em. It’s lice season you know.” She was pulled out of the shower stream and a younger guard approached her with a safety razor. Without any fuss or ceremony, Jenny was divested of her pubic hair. She had never shaved down there before, and it felt strange to be so exposed. “Okay, rinse off.” She was pushed back into the shower and rinsed her now bald privates, the last remnants spiraling down the drain.
The guard threw her a towel and her jumpsuit, ordering her to dry off and get dressed. Jenny slipped on the jumpsuit and followed the guard down some more corridors and into another room.
“Might as well get your hair cut while we’re over here, Stein. I think you’re overdue anyway. Look at this mop.” Jenny grasped the ends of her blonde curls and more tears started to flow. “Oh, come on, Stein, what’s with you? It’s just a haircut, for crying out loud!”
In the middle of the room was a standard barber chair, and Jenny was terrified that she was going to get one of those prison haircuts that she had read about. She sat down in the chair and a cape was thrown around her and fastened at the neck. The guard roughly pulled Jenny’s hair out of the clasp and let it fall over her shoulders.
“How the hell did your hair get so long? I’m going to have a chat with those guards in B-wing, they’re not following hair protocol. This is the third one this week.” The matronly guard complained.
A short little man emerged, and without so much as a by your leave, started in on Jenny’s beautiful blonde locks. There was no style at all, just a blunt off the shoulders bob. Jenny breathed a sigh of relief, realizing that she wasn’t getting a crewcut.
“You wait here, Stein, while we get your paperwork in order.” The door to the little barbershop was closed and locked. A large window with bars was the only light in the room and Jenny looked through it, down over the parking lot where she had parked three days earlier.
Jenny knew her car would be gone but couldn’t resist looking for it. Strangely enough, it was there. Then Jenny realized that it wasn’t where she had parked it. Her car was much closer to the gates. What was going on? She couldn’t understand why it wasn’t where she left it.
There were some people at the gate as it swung open. “Oh my God, Brian!” Jenny banged on the window, but there was no way he could have heard her. Then Jenny got the shock of her life. Jenny’s jaw dropped open as she saw the woman from the restroom get in the car with her boyfriend and drive away.
She felt faint and had to sit back down in the barber chair. She was so shocked by what she had just seen that she didn’t even cry. Jenny couldn’t believe that even her own boyfriend couldn’t tell her imposter from herself.
An overwhelming sense of despair crept over her as she sat, a chill running through her. Jenny slipped the cape from the back of the chair and wrapped it around herself for warmth. A few moments later the door opened, and the barber and guards stepped back into the room.
“Well, well, well! It seems our standard prison cut wasn’t sufficient for Miss Stein here.” The matronly guard mused. “She’s all caped up for more.”
The barber clipped the cape back into place and reached for his scissors. Jenny kept trying to say something, anything, but she was lost for words. It seemed the shock of seeing her boyfriend with her imposter had left her speechless.
“Don’t worry about those, Don. Let’s give her what she wants.” The younger guard sneered.
The barber disappeared into his office, returning with some large black clippers. Jenny was desperate, she had to say something, but she just couldn’t. He plugged them in and approached Jenny with a crooked grin on his face. Whirring to life just as they were placed at her forehead, the little man plunged them into her bangs, the force of the stroke flexing her head backward. The barber had many prison induction cuts under his belt, with the largely male population, and took no time at all in reducing Jenny’s hair to mere stubble.
Thirty seconds after it began, it was over, and the clippers fell silent. There was no mirror in the room, but Jenny managed to lift a hand to her head to feel her almost smooth scalp. What she had dreaded the most had come to pass, and then some. She nearly was completely bald. “Ok, Stein, the fun’s over. Let’s get you back home.” A wicked smile came over her. “The girls are just going to love that haircut, Sweetcheeks.”
As they entered “her” cell block, a loud and raucous noise rose up as the other prisoners welcomed her back. She got a lot of razzing over the haircut and Jenny again ran her hand over her smooth pate in disbelief. They stopped in front of a dull grey door, which was slightly ajar. Inside was another young woman, her appearance quite striking. A tattoo graced the woman’s cheek, the symbol lost on Jenny.
“You two behave yourselves now.” The door was closed behind her, and Jenny was left to the tender mercies of her cellmate.
“Love your head, babe.” The woman smiled. “I know I’ve been bugging you to do it, but I never thought you’d actually go through with it.” She reached out and ran her slender fingers over Jenny’s head. “Thank you.” She mocked, contritely. “By the way, there’s a letter there for you on your cot.” Jenny looked over at the envelope, addressed to ‘Julie Stein’.
Dreading what she might read, Jenny slowly opened the letter:
I am sorry for what you are about to go through, but I fell in love with this girl. She looked just like you, and we got time alone together when I bribed the guards enough to let us sort laundry together. We had this planned for a long time.
Please forgive me, but I really do love her and not just for looking like you, but for doing the things that you always refused to do. You know what I mean, the kinky stuff. Why do you think I kept feeding you coffee in the common room? I knew you’d have to use the ladies’ room before your trip back. You have to admire the plan though, right?
Julie will be taking your place at your job; she knows everything and is well studied for playing the part of “you”. By the way, Julie is in for armed robbery and will be up for parole in 12 years, but now with this escape “attempt” you probably won’t make it even with good behavior.
One more thing, babe. The girl you’re cellmates with is your Dominant lover. Don’t disappoint her if you know what’s good for you. She has nasty friends.
Jenny stared for what seemed like hours at the note, then set it carefully on the table between the beds. “Is that another letter from that boyfriend of yours? I told you I don’t approve of you talking to him.” She grabbed the letter, crushed it in her hands, and flushed it down the toilet. “Time to pay homage to your Mistress, Sweetcheeks.” With that, the tattooed woman stood up and slipped down her jumpsuit, revealing her slender muscular body. “On your knees and worship me, you baldheaded bitch!”
Jenny was so worn out that she complied without thought or emotion. She knelt before the woman, who wrapped both hands around the back of Jenny’s smooth head and pulled her face into her sex.
The strong, musty odor filled Jenny’s nostrils as she forced her tongue out and licked the smooth pink lips. “Now that you’re a bald slave, we’re going to keep you that way.”
Jenny plainly heard the comment, her face buried deeply into her superior woman’s pussy. Suddenly, a wave of arousal swept over Jenny, her humiliation so complete that it overwhelmed her. Jenny’s jumpsuit revealed her moistness as it crept down the inside of her thighs. The woman stripped her, slipping her fingers through Jenny’s sex.
“I think with all that new skin, it might finally be time for that tattoo I’ve been threatening you with.” The woman ran a finger across Jenny’s forehead and smiled.
Jenny laughed inwardly, as her Mistress straddled her face, driving her hips into the task. She had fallen a long way. Once an attractive young working girl, with a good job and loving family, Jenny was now nothing more than an ugly, bald-headed prisoner of the state, enslaved to a tattooed Mistress who was going to keep her bald, ugly, and probably tattooed.
She thought about the imposter, living out her life on the outside, making love to her boyfriend, working her job, driving her car, and taking over her apartment. Another rush of pleasure swept over her as she realized that maybe she got the better deal. “Thanks, Jenny,” She thought.