South American Jail

by Bald-and-Proud · November 13, 2022

South American Jail – Shearingly

My name is Alan. I’m the manufacterer’s representative for a heavy equipment company. I’m stationed in a small South American country (which I won’t name because you might all want to relocate there) that’s trying to improve their road system. I ended up living in a city that had a fair amount of tourism. I thought, by doing so, I might get to occasionally see a few of my fellow countrymen. The first three months I worked day and night getting things running smoothly. After that I had a lot of free time on my hands. I might only work half a day two or three times a week and the rest of the time have to myself.

I did all the typical tourist stuff and then started looking for other things to do. I got in the habit of eating lunch at the best and largest hotel in the center of town. It was a good place to run into tourists from America, Canada or England. Scarcely a week went by that I didn’t meet some interesting (and often beautiful) women who enjoyed a friendly contact in a foreign city.

When I arrived in town, I was introduced to all of the important town officials because I dealt with them in my work. My company spread a lot of money around and some of it ended up in the pockets of these officials so they were very friendly to me. After eating at this hotel for a few days I noticed that the chief of police ate there every day also. One day he waved me over to his table and we ate together. He was an interesting man, who could be quite charming, and we developed a friendship.

As we talked one day he offered to give me a tour of the police station and his jail. I was a little bored, so I took him up on it and the next day he was showing me through his personal domain. While I was there a couple of his officers brought in a young, pretty, dark-haired woman, a native of the city. She was being charged with prostitution. I had an idea that the chief wasn’t all that zealous about preserving high morals, but she probably forgot to pay the right people and here she was.

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She was struggling against the officers who had handcuffed her and were pulling her along. “I didn’t do anything. This is a setup,” she said among other things in her fiery dialect. They just laughed and ignored her pleas. When we got done touring the cell blocks we were back in the processing area and I heard a woman scream, “No, No, please don’t.” I looked at the chief and raised my eyebrows.

He chuckled and motioned me to follow him. He took me to a room that had a one-way glass where we could see in, but the occupants of the room couldn’t see out. What I saw quickened my blood. The native woman, young and pretty was tied to a chair and a sturdy-looking matron was running a set of electric clippers all over her head. I pinched myself to see if this was a dream. Big hanks of long black hair surrounded her chair, filled her lap and clung to her dress from the shoulders down.

I knew my blood pressure was rising and I suppose my jaw dropped open because the chief laughed at my reaction. “Do you like this?” he asked. I gulped and decided not to deny it.

“Yea,” I admitted. “I’ve always had this thing about a woman getting her hair cut or head shaved.” He stood there with me and let me watch until the job was done and the thoroughly demoralized woman was led away with her skull gleaming white (she had been buzzed and shaved). I tried to memorize every detail to savor at a later time.

A few weeks later, at lunch, he was particularly excited about something. He couldn’t contain himself so soon it came out. His men had arrested two American women that morning. The charge was drug possession. He told me that they were caught red-handed, no question of their guilt, an open-and-shut case (he liked American cliches). I asked if the American embassy got involved in situations like that. He told me that he had a free hand to deal with these people as he chose. Of course, he came from a very wealthy, influential family and had connections to everyone. No one was going to question what he did. He said the embassy didn’t get involved unless the arrested people were famous or rich.

I asked why he was so enthused about it. He had been drinking freely from the minute he arrived at the hotel and was quite relaxed. He leaned over and in a whisper confided to me that arresting young, pretty North American or European women was a real treat. He said he took charge personally, made them strip off their clothes and performed a body cavity search on them. An idea popped into my head and so – nothing ventured, nothing gained – I dove in.

I asked him if the American female prisoners would be forced to have haircuts like the woman I had seen that day. He said that they normally weren’t and wondered why I asked. I was straightforward with him – man to man. I told him that what excited me involved giving women haircuts that they don’t want. I smiled and winked at him and then offered my services as a barber for the women who were arrested and put in jail. He listened carefully and accepted what I said without a negative reaction. I took that as a good sign. He hinted around about what would be in it for him and I assured him that he would be amply rewarded. I palmed a large denomination bill from my pocket, made sure he saw what I had in my hand, and said, “Shall we shake on it?” That seemed to clinch the deal. He smiled and stuck out his hand to shake.

“Sure Alan,” he said. “Come with me after lunch. I will give you another ‘tour’ of the jail.” He winked back at me as he said that. “Perhaps you will be able to be the personal barber of all North American and European women.”

It was hard for me to finish my lunch, I was so excited, but I did and then walked with the chief to the jail. The women were being held in a special room, separate from the rest of his prisoners. He had talked to the judge (who was related to him – his uncle). who told him to go ahead and put the two in jail – their trial would come up in a couple of weeks or so.

I was shown to where I could see the proceedings inside without them knowing I was watching. I watched as the chief explained their predicament to these two girls. Their faces fell when they heard the evidence that had accumulated against them and that they would be going to jail to wait for their trial. They asked for a lawyer or a phone call. He told them all in good time.

With a leer on his face and heavily accented English he told them to strip. “What?” they said.

“Strip!” he repeated himself. “Take all your clothes off.” He actually rubbed his hands together and licked his lips in anticipation.

“Why?” they asked

“Don’t question me,” he thundered. “I’ve got to search you to make sure you aren’t smuggling anything into the jail.”

They began to assure him that they had nothing hidden on them. He said, “Either take your clothes off or I’ll get a couple of guards in here to tear them off.” They started to slowly remove their clothes. The chief got a big thrill out of this, it was obvious. He examined them thoroughly, touching, rubbing or fondling all their private places. He then ordered them to bend over.

Their look of horror as it dawned on them what he was going to do next was a bit of a turn on. He drew out and savored the moment as he poked his fingers inside their bodily orifices. By the time he was done both were weeping and sobbing. They were allowed to put their clothes back on and the two were then handcuffed and left in the examination room. It took most of an hour but eventually they had calmed themselves down and were sitting close together for comfort whispering of their fears and worries.

I knocked on the door and then opened it. They tensed and looked up to see who it was. I smiled at them sympathetically and introduced myself (using a false name, of course). They brightened, “Are you American?” they asked. I told them I was and what city I was from. “Oh, please help us,” they said, almost in unison. “Are you a lawyer? Can you help us get a lawyer?” Their rush of words threatened to overwhelm me.

“Hold it. Hold it. I’m here to help you,” I reassured them. “The chief told me a couple of American citizens were arrested so I came as a sympathetic friend” (I had thought through my “cover” story). “The embassy has been notified, but unfortunately it takes a long time to work through the red tape and beaurocracy here. It will be about a week before anyone from the embassy will get down here to see you.”

“What, a week?” they exclaimed as their faces fell. “That’s right, so just hang in there and everything will be O.K.” I asked them what the charge was and what evidence they had against them. As they explained I made my face grow long and sad. I shook my head and said, “That doesn’t sound good at all.”

The girls introduced themselves – Regina and Tami, from Michigan. Both were very pretty girls with beautiful hair. My legs grew weak at the thought of what was in store for them. Regina had thick dark blond hair that was permed into a cloud of curls framing her face. It wasn’t real long, just covering her collar, but so thick and lustrous – the kind you’d like to plunge your fingers into. Tami had gorgeous auburn hair – very dark, but with enough reddish highlights to make it a delightful auburn color – which ended about six inches below her shoulders in a ruler-straight line across her back. Tami taught kindergarten and Regina was the librarian at the same school. They had been planning and saving for this trip for three years. Now it had all turned into a nightmare.

I talked to them for a while, providing a calming, soothing interlude for them. Then I got down to business. “Ladies, I’m not just here to pass the time. The chief allows me in his jail and to meet with fellow citizens of the U.S. only because I do something in return.” They looked at me expectantly. “Now, let me warn you, your circumstances have started you on a series of very unpleasant experiences.” They looked at each other and nodded emphatically. “You may wonder if I am your friend, but let me assure you that my purpose is to make it easier for you in the long run.”

Now they were looking at me with very puzzled faces. “What do you mean?” they asked.

“O.K., I’ll explain, I just wanted to warn you and I want you to keep it in mind as I explain.” They nodded that they understood. “O.K., the bad news is – all the women who are arrested and put in this jail get their hair cut,” I paused and watched their reaction to that news. They looked shocked but didn’t say anything. “That haircut, before I offered to do it, was done by a big gorilla of a guard – did you meet him yet?” They nodded hesitantly (there were actually two or three who met that description and I knew they had seen one really large, ugly, ferocious-looking guard). “In the past he has been known to pull a girls hair out by the roots, a clump at a time (they both shivered), or cut the hair with scissors and then shave her head with an old, rusty, dull razor that nicked and cut her scalp more than it shaved off hair (again they shivered) and sometimes he used a real strong Nair-type stuff and left it on way too long so it was months before any hair grew back (they groaned). Now when I learned what was happening I asked the chief and he agreed to let me do the hair cutting and head shaving as long as it’s O.K. with you.”

“Why do we have to get a haircut?” they asked almost in unison.

“I asked the chief why he had that rule. He told me something about lice and vermin in the cells and that it was policy. But the truth is I think he just wants to humiliate his prisoners so they don’t give him any trouble. It is certain that you will get a haircut, the thing is do you want me to do it, gently, or do you want a gorilla to do it who gets his jollys hurting women?”

“Oh, sir,” Regina said shaking her head of blond curls, “I don’t want a haircut, but if it has to be done I’d want it done by somebody friendly. I’ll let you do it.”

“Me too,” Tami chimed in.” I smiled at them reassuringly and told them I would go and get everything I needed.

When I went out the chief was standing by the one-way glass shaking his head in admiration. “That was pretty smooth,” he told me, “but I’m not sure I like the way you portrayed me.”

“Think of it this way, chief,” I told him, “these girls think you are such an ogre, they will cooperate completely. You will have no trouble from them, I’ll guarantee it.”

I brought my satchel back into the room where the girls were waiting. Their hands were cuffed behind their backs and I told them I didn’t have a key and the chief wouldn’t let me uncuff them anyway. I said that I would be very gentle but that I would have to do everything for them. They said it was O.K. with them.

“Let’s start with Tami,” I said. I helped her stand up and moved her to a stool in the center of the room. I steadied her as she sat down on the stool. “You have gorgeous hair, Tami,” I told her. She smiled shakily and said, “Thanks.” I pulled out a brush and began to pull it through the gleaming auburn tresses. It had gotten tangled with the chief’s examination, but soon I had it all smoothed out. “I’ll start by cutting it short all over, then I’ll use some clippers to buzz it down to the scalp. When that’s done, then I’ll shave your head and that will satisfy the chief.” After a pause I said, “Are you ready now Tami? Is it O.K. for me to begin?”

She didn’t trust her voice, but nodded her head and croaked out a, “Yes, go ahead.”

I chattered away, making small talk about things I had seen in South America since I’d been there and about what I knew of Michigan and anything else I could think of to take their mind off what was happening to them. I snipped away at Tami’s auburn locks, putting each long tress into a small carboard box I had brought for that purpose. When I had her lovely head of hair reduced to less than an inch in length, I pulled out the clippers. The soft electric hum didn’t alarm her, but the first touch of the cold teeth on her forehead made her jump. “Take it easy, Tami,” I said. “I’m trying to be gentle and as careful as I can, I don’t want these to hurt you.” She held herself still, but was very tense. The tears started flowing as she felt the clippers roam all over her balding skull. She shuddered and shivered every so often as the vibrating clippers tickled her. When I pulled out the shaving cream and a safety razor, she sobbed, “Is that really necessary?”

“No,” I replied, “I can call the gorilla in here to finish the job.”

“I’m sorry,” she managed to get out through her weeping, “go ahead.”

I finished up with her head and then said, “Tami, the rest of the bad news is that the chief insists that you be totally free of hair, everywhere.” It took a moment for that to sink in and then a fresh wave of sobs coursed through her. I heard Regina’s gasp as she caught the meaning of those words.

I helped Tami stand up once again and with gentle fingers I unbuckled her thin belt and unhooked then unzipped her slacks. They were tailored and fit well, but weren’t too tight, so I was able to slip them off her hips and down to her ankles. There was a table in the room so I helped her hobble over to the table and then half lifted her up on it. She laid back and then raised her hips so I could slide her panties down her legs. She shuddered, thinking of what the chief had already done to her that day, but I spoke soothing, calming words to her as I used a smaller set of clippers (designed to trim a beard) to get the hair between her legs as short as possible. The shaving cream and razor were endured. She turned her head to face the wall and just held herself still, not wanting to admit that all this was happening to her.

When I was finished with that, I wiped her off with a towel and tried to pull her clothes back up. It wasn’t the same as dressing herself and between that and the freshly shaved crotch and accompanying discomfort, she was miserable.

I turned to Regina and asked, “Which do you want me to do first? Head or crotch?”

She glared at me. “I’m not so sure you are as much of a friend as you made yourself out to be. I think you are enjoying this as much as you said that guard would.”

I shrugged and said, “Do you want me to call him in here? At least I didn’t hurt Tami like he would have. He’s been pretty unhappy since I took most of his business away from him. He’d love to take his frustrations out on you.”

With that she closed her mouth and stood up. “Put me on the table first.” She couldn’t bring herself to say the word “crotch.” She was wearing a short, swirl skirt, so I just reached up underneath and pulled her panties down. Then I lifted her up on the table and pulled the skirt out from under her, laying it up on her abdomen, out of the way. It was apparent that she wasn’t a true blond and when I mentioned that she blushed a little. I buzzed and scraped away until she was smooth and hair free there.

She moved, a little weakly to the stool and sat grimly while I flicked the clippers on and plowed them through her thick blond curls, mowing stripe after stripe across the top of her head. Then I pushed her head forward and starting from the nape worked up to the crown of her head, until all the curls were severed. I went over her head again to catch any patches I’d missed, then shaved her smooth. When all of that was done I pulled out a bottle of hand lotion and rubbed it on both of their heads and everywhere I’d shaved. I told them I had done all for them that I would be allowed to do and hoped they got along O.K.

A few weeks later I asked the chief about them. He said that they had been tried and found guilty and sentenced to 18 years of prison. He said the prison warden was surprised to find that they were such meek and compliant women. The chief laughed and said to me, “They gave us no trouble. We make a good team.”

THE END