The Detention

by Sheralyn Tiffany Crosse

  

It had been planned for 3 days. It had been a fantasy for 6 months. Angel had finally asked me point blank. And I answered her question truthfully, even though I was gravely afraid of losing her friendship to prejudice. I think somehow she already knew. It would serve no purpose to lie, and possibly lose her trust. So the greatest part of telling the truth was she has no problems with it. She accepts it. In fact, it was to be her idea for us girls to get together.

The plan was for me to get ready and then meet her at her house. She wanted to role-play first, before we went out. But she wanted me to come already dressed. I supposed she didn't want her neighbors to see a man go into her house and two girls come out.

I chose my black five-inch sandals with the thin ankle strap, black, long sleeve, turtleneck leotard, the dark-grey micro mini skirt (which did not allow me to bend over), and my long, wavy, red hair wig. After spending an hour and a half on my makeup, I was satisfied I was ready for my big day out. I took for backup a white and black skort and another pair of shoes, black, five-inch pumps with a half-inch ankle strap and a big silver buckle.

The trick now was to get out of my house without the neighbors seeing me. But, having no clue what their daily schedule, let alone today's, was like, I had to take my chances. This was going to be one of the best days of my life and my neighbors no longer mattered. I didn't even feel I'd have to lie. This was worth it and I wanted this badly.

Role-play

When she answered the door, I thought I saw a flicker of surprise. But she hid it well, if it was there. I was a little disappointed though. Although she had done her makeup, she was still in her sweats. But this did arouse my curiosity as to what she meant by the role-playing.

"Hello. You're early," she greeted.

Oh no. I forgot. Rule number 1, girls are never on time.

"I'm on a tight schedule," I replied. "You know, even in sweats, you look good."

"Oh thanks. You look good. Doing a good job with your makeup. That skirt is a little too short, even for me, though. But I have some things we should try on first."

Is this going to be part of the role-playing she mentioned?

She invited me in and I headed for the dining room table to sit down and wait. Unexpectedly, she said, "Oh no, you're coming with me to get you re-dressed." After leading me up the stairs, she stopped by a bedroom.

"You remember my brother is in the police academy? He brought home one of those blue backgrounds that they use to take mug shots, that shows your height," she began. "And I have an orange jumpsuit for you."

This isn't going to be the proverbial bad-cop, bad-CD is it?

"I know you have the foam breast forms. But I managed to get a hold of a silicone pair," she continued. "But don't ask me where I got them."

"Where did you get them, and why?" I asked anyway. I really was curious.

"I told you not to ask. Besides, you'll see in a minute. Here, change them," she commanded.

As she left the room, I took off my micro skirt and began to unzip my leotard. The silicone breasts were a marvel and a dream come true. I wish I could keep them. They fit perfectly in place of the foam pair. I was glad, though, that I wore my 18-Hour Comfort Strap. It should be able to support them.

As she came back into the room and surprised me, she snapped, "Oh no. I forgot to give you the adhesive. Here, let me help."

Adhesive? How long will I be stuck to these?

Although it was a little awkward, she got the silicone breasts adhered in place. But she made me change out my bra for one of her black Victoria's Secrets.

"This one was a gift. But it is too big for me. Since it fits you, you may have it," she continued.

This is too awesome!

As I was getting the orange jumpsuit ready to put on, I noticed it had a prisoner's number on the back.

"Oh, my brother brought these home for me," she explained as she held up another one.

"How come mine has a number and yours doesn't?" I quizzed.

"I'm not sure. They are supposed to be old and to have been thrown out," she answered. "My brother intercepted them."

As I pulled the jumpsuit on, I noticed I was showing a lot of leg. I might as well have been wearing the micro skirt. "Did you make them into cut-offs? Or are they really are supposed to be like this?"

"No. Wait, yes. I modified them for us," she said.

As I zipped up the front, I noticed real quick it wasn't going to go all the way to my neck. It stopped short and left me with an average revealing amount of cleavage.

So that's why the silicone.

"Those shoes don't go with that," she observed.

So I pulled out the backup shoes and took a moment to buckle them on.

"That's better. Still a little 'sluttish', but I guess that's Okay," she commented.

Good.

I realized then that she had gotten her jumpsuit on, while I was fumbling with the ankle straps through my long pink nails. She put on a pair of black high-heel pumps too.

"Wait. You're not going to be the 'bad cop'?" I asked.

"No. And I want a picture to remember you by, just like that," she teased.

After taking me into her brother's bedroom and handing me the little sign with the numbers on it, she said, "Hold this and stand in front of the blue height/lineup thingy."

"Is this for a mug shot? Are these numbers the same as the ones on my back?"

"Yes."

Boy, she looks sly.

"This is between us, right?" I anxiously asked.

"Huh? Oh. Yeah. I'll leave you with copies too," she assured.

After taking several different types of 'mug' shots, I asked when it was her turn. Just as she was about to 'pose', she started, "Oh no. We have to go. We'll do my pictures later.

"What? Dressed like this?"

"It's Okay. Where we're going, it's the style. We're going on a tour where my brother works."

"But I look like an inmate!"

"Oh. I knew you'd be a big baby. That's the only jumpsuit that I thought would fit you. So, since I couldn't get the painted number off of the back, I sewed some Velcro to allow me to put this orange patch over it."

As I felt a little chastised, I was apprehensive about asking why the patch wasn't sewn on.

"Come on. We don't want to be late. They are on a schedule, too," she said as she quickly grabbed her purse and keys, pausing only to place the patch over my numbers.

Demonstration

The ride was exciting, mainly because I was with a very beautiful girl who was treating me like just one of the girls, out and about doing what girls do to have fun. It was fun to talk about style, makeup, and fashion. But even as she parked the car at the Detention Center, I was still very apprehensive. I know I would have felt more comfortable in my micro skirt than a jumpsuit, especially an orange jumpsuit. We had a long walk across a very large parking lot. I wished she had parked a little closer. As we entered the foyer, where she was to sign us up for the tour, we had quite the stares. I presume it wasn't so much because of the way we were dressed, but because of what we were wearing.

When the group was called to gather around, Angel allowed me to hold us to the back of the group. It allowed me to see who in the group couldn't control themselves and turned around to stare, even nonchalantly. I was surprised that a young, pretty woman was among the curious. She did stare, not glaringly, but with a friendly smile. She almost seemed to be looking at me, more. I wish. She was dressed in a business skirt-suit, which was much more appropriate than Angel and me. She had on black high heel pumps, a black pencil skirt that semi-covered her knees, and a very feminine red wool jacket that came down only to her waist. And most noticeably, she had bright red lipstick. Although dressed in conservative attire, she still had much sexual allure. I wondered if she would try to greet us, if not at lease me.

After an introduction and history, which was a little longer than my five-inch heels allowed me to feel comfortable in, our guide led us into an area where there were several 'processing' cells. We were asked to gather in a semi-circle so that everyone could see, and be seen by, the tour guide. Angel and I held back to one far side of the group. I could still see the businesswoman; I wanted to keep her in my sight as well. As the guide was talking, he picked up a set of restraints that included the belly chain, which goes around the waist, hinged handcuffs, and the leg irons that had the chain linking to the belly chain via the handcuff ring.

I wish I could be used for the demonstration.

"May we have a volunteer?" the guide inquired.

A bald man off to the other side of the group raised his hand. Then things went too fast for me, clouding my judgment. I'm not sure of what to think of Angel's actions, but she raised her hand and volunteered me.

"Don't worry. He's my brother," she calmly whispered.

Does that businesswoman have a twinkle in her eyes?

Turning to Angel, I whisper-shot, "Does he know about me? I don't want to be embarrassed!"

"Yes, but he won't expose you. Trust me. Isn't this your fantasy?"

She gave me the most innocent look. And, yes, I had told her I wanted a genuine set of restraints. Maybe this was the best she could do, and all for me.

Surprise

That businesswoman was looking expectantly at me. Just when the guide was about to accept the man on the other side of the group, someone shouted, "Pick the red-head." And then all eyes were on me.

But this was a once in a lifetime opportunity. And these people won't ever see me again. Right?

Our Prisoner

As my feet were tiring, I swung my hips just a little more when I slithered to the front and beside our guide. I have found this helped me walk on hard surfaces in high heels. It also made me feel hypnotic and seductive. I'm probably just kidding myself. But at this point, I particularly liked it. Did the guide like it too? Or was that sparkle in his eyes for another reason? Angel did not come with me to the front.

The guide turned me to the side, and facing a little into the group. I hoped no one could 'make' me. I noticed that most were either looking at my breast or my legs. I hoped those looking at my face were admiring my makeup. I tried to keep eye contact with the guide though. I couldn't help but see the businesswoman.

Did she just wink at me?

The guide first took my purse and set it aside, but away from the group.

I should have left it with Angel.

He started talking about the belly chain and how the rectangle end was inserted the through the round end, leaving the rectangle end out in front, as something to hold onto. This reminded me of a choke collar. Then, facing me, he wrapped his arms around my waist, basically hugging me, and brought the chain around me. Getting squeezed up against him and feeling the pressure of his chest on my boobs sent a small wave of butterflies through me. A few in the group snickered. As he was addressing the group, I was glad he wasn't making much eye contact with me. Despite being Angel's brother and knowing who I was, I'm glad he was very professional.

Now he inserted the rectangle end of the belly chain through the rectangle end of the other (vertical) chain, which led down to the leg irons. Next, he opened one cuff of the hinged handcuffs to slip through the rectangle end of the belly chain. I had seen this kind of demonstration before in college. By having the handcuffs on, the rectangle link of the belly chain could not escape back through the link on the leg iron chain and the round end of the belly chain.

Here comes the fun part.

He gently took my left hand to the open cuff, and in that instant butterflies filled in my tummy as he locked the bow around my wrist. I noticed he left the keyhole on the inside, towards me, where I could not get to it even if I had a key because the hinges wouldn't permit me to do so.

I guess I have to trust him now. There's no way I'm going to get myself out of this.

He then gently took my right hand, as if helping me out of a car. He kind of smiled, as if he were about to enjoy this too. Suddenly he brought my right hand to the unused cuff's bow, which slung through the cuff and around my wrist and zipped shut. It was almost perfect. He had only one more click to go. I couldn't help but catch my breath. At that moment I realized the rectangle link was so close and tight against my tummy, that I would not be able to slide the belly chain off of me. It was the perfect size for my waist.

How did he know what size belly chain he needed for me?

Our guide noted to the group, "Notice how our prisoner does not have any access to the keyholes. The belly chain is too tight to bring her hands away from her abdomen." He then used the end of the key with the 'stick' to double lock the handcuffs.

Oh God. This is not a good time for testosterone to kick in.

Someone in the group gave a short, high to low whistle.

Was that Angel? Or the businesswoman?

I stole a glance at the businesswoman. Her eyes were wide and fiery. But she did not wink this time. She did, however, draw in a slow breath. Was I fulfilling some kind of fantasy for her? Was she really here for the tour?

And before I knew it, I realized our guide had moved on and restrained me with the leg irons. I had missed it completely. Where was my mind? But I did not miss noticing the leg irons' keyholes were such that I would not be able to get to them at all with my hands restrained, let alone so close to my belly.

And it is done.

Now I am a prisoner. Now I am dependent. Now I am helpless. Now I had no choice but to trust Angel and her brother. Even with my key in my purse, I would not be able to get out of this. I attempted though to wriggle my hands. Even though I was trying to be unnoticeable, the chains rattled a little. Even though they were a little loose, there was no way to slide them off my dainty wrists and over my thumbs. I was stuck. I peeked at the businesswoman.

Does this excite her too? What does she think of this?

Again, our guide used the 'stick' end of the key to switch the double locks and looked up at me and asked, "Are those too tight?"

Oh boy. Do I have to speak?

I noticed that I would not be able to slip them from my petite ankles and beyond my heel. I just shook my head 'no'.

And again, this is not a good time for testosterone to kick in, especially in an orange jumpsuit. Okay, don't move and nothing extra will bulge out.

Can I have these? Why does Angel's brother look satisfied? Am I concealing my excitement? Can anyone else see? Could I somehow figure a way out of these? Will I have to? I wonder how truly vulnerable I am. How much control do I really have? I really do like this, a lot!

As he rose and turned his attention back to the group, the guide continued on with the demonstration. "Now, our jumpsuits are not as short as this. They have the full legs. And our prisoners wear socks and comfortable slide-on shoes, like flip-flops," the guide said to the group. "When we put the leg irons on, they go over the legs of the jumpsuit to keep from bruising our prisoners."

"Well, we must move on to the next part of the tour," he continued. "Just one moment while I retrieve my restraints."

Unconsciously, I took a very small step backward, away from him.

No! Their mine! Let me wear them through the next part of the tour!

Angel's brother started padding his own pockets. "Oh wait! Where's the key? Just kidding," he jested. No one else really caught the humor.

Then he turned to me with the key in his hand.

No! This is too soon! Just a little longer? Let me test drive these.

Wait a minute. Does he look smug?

He gently took my left hand and tried to position the handcuffs where he could insert the key. I could see the irony, though, that he couldn't get the key into the keyhole without turning our wrists sharply; the handcuffs were right against my tummy and under my breasts. It was a tight squeeze for both of us.

Are my breasts in your way? Are you distracted?

Although everyone was patient, some in the group started whispered conversations. Angel's brother patiently kept trying to insert the key. Every now and then he'd bump my breast, which would send another wave of butterflies through me. I was beginning to realize how vulnerable I was. I could do nothing to help or stop him. He was in control and I had no password.

After a little time had passed, I sneaked a peek at his progress. And then I felt myself start to pale. I saw his expression was genuinely serious.

If he's just acting, he's really good!

The key wasn't going into the keyhole. It was just that simple. I couldn't tell if the key was too big, or if it wouldn't go down around the pin in the middle of the keyhole. But it wasn't working. I already knew I couldn't get myself out of this. It made me feel even more helpless.

So he then tried one of the leg irons. But I could tell by his expression that it wasn't working either. And I still couldn't tell if he was just acting.

Sometimes wishes come true. But this time, it didn't seem anyone was in control. In my fantasy, someone was always in control. Someone always has to be in control! I was starting to panic.

Am I going to be exposed in the process of getting out of these? Am I going to be publicly embarrassed?

This time, I looked at Angel. She was too busy looking at her nails. Typical bombshell. It was always about herself. She was oblivious to her surroundings or what is going on. And I couldn't say anything. She was too far away. But I needed reassurance. I needed to know he brother wasn't a complete idiot. I wanted her next to me.

Aren't girl friends supposed to stick together?

My panic was growing. I couldn't risk being in the headlines. I could just see them, "Transvestite Captured!" I'd be the laughing stock at work and home and an embarrassment to my family.

Now Angel was touching up her makeup.

I stole a glance toward the businesswoman. She looked hungry. Somehow she looked satisfied too, as if she willed me to be stuck. But she couldn't get to me. Not right now. I felt caught in someone else's trap, facing a hungry lioness. This almost made me feel excited. But even if she saved me, I might still be in her control. And I don't know if I could trust her.

Wake up. Separate yourself from fantasy and come back to reality.

Then our guide spoke again. I was surprised at how calm and professional he seemed. But this time he addressed a nearby guard, from behind me.

"We are on a schedule and I must pass this group on to the next guide of the tour. Would you keep an eye on our prisoner?" He winked at me. "Also, the next bus is due, hence my need to get the tour out of the way. So you may want to take our prisoner into one of the processing cells to keep her safe."

After the guard agreed and our guide thanked him, the group was led out of the foyer of the processing cells. He did motion Angel, however, to stay with me.

Thank goodness!

Angel picked up my purse and followed as the guard led me to the nearest processing cell. The guard helped me to sit down at the table and Angel sat next to me, to my right.

With that, guard walked out and shut the door with a heavy, metal, dungeon ring. Were we safe in here? Or was I doubly trapped?

Transport

Angel put her left hand on my chair, beside my right leg and leaned closer to me. She started teasing me by gently moving her right index finger around my handcuffs and wrists.

Do I have your undivided attention?

Then her finger slowly moved up along the zipper. Then it wandered around just under both of my breasts. Her gaze shifted from idol curiosity to meet my eyes and she moved her hand to my chest to gently wave back and forth and back down to my breasts. I could see her turn sly when she kept my gaze and put her hand on my right knee. It began to slowly move up and to the inside of my leg. She didn't get very far though when she got to the cuff of the jumpsuit. It was a little tight. But she still managed to get a little of her fingers underneath.

Is she turned on? Or is she just being a tease?

I couldn't reciprocate. I couldn't move my hands to touch her. I couldn't pet or stroke her in any way. She saw my limits when I tried.

She licked her lips and moved her hand down to my left calf and slowly moved it up and across my kneecap. I wondered if she felt me shudder as her hand came up my left thigh. She had to move in closer, almost cheek to cheek, as she continued her right hand past my thigh, and hooked it around my waist and under my left arm. She stole a downward glance.

Is she looking at my boobs? Or is she accessing how helpless I am?

Her gaze came back to mine. Her lips started to part just a little.

Is she going to kiss me or talk?

Just then the door was being unlocked.

"I like you this way," she said coolly.

When the door opened, she jerked away from me. She looked like the little schoolgirl who had just been caught.

In came her brother, with a folder and a duffle bag. The door slammed shut behind him as he walked over to give Angel the bag. He rounded the table and sat down across from me.

"Did you bring another key?" I inquired.

Without looking up, Angel's brother opened the folder and replied, "There's nothing wrong with the key." The folder contained Detention Center paper work and my mug shots from earlier. One of the papers looked like some sort of prisoner transport document.

Looking up and staring straight into my eyes, he stated, "Angel, the court is pleased you turned yourself in. The bus will be loading soon and you'll be on your way to begin your sentence at the New Mexico Women's Correctional Facility."

With that said, Angel reached behind me and pulled her face close to mine. I felt her left hand on the orange patch that was covering up the numbers. She smiled mischievously; and very slowly she pulled off the patch.

Great Escape

I could only sit there, shackled and stunned. Are they yanking my chain? Angel turned and opened the duffle bag and pulled out her sweats.

Is that how I missed her change back at the house? I must have arrived when she was testing how the sweats would look over the jumpsuit.

She took off her heels, and after she placed them into the bag she pulled out some bobby socks. She put on the socks, the sweats, and then she pulled out and put on some tennis shoes. She pulled up her hair and put on a small, stylish hat too. This was her hip-hop style, and a completely different look. With her sunglasses, she would be unrecognizable if she walked out of here like that.

She then reached for my purse. She retrieved my identification and keys.

"You won't need these."

"Why are you doing this? How far is this going to go? I have a life too," I stated earnestly.

She came over and got close to me, almost face to face.

"I just need some time. When they figure this out, they'll let you go. And I'll be far enough away."

"But why?" I just couldn't understand what was going on with her.

She pulled back and stood, thinking.

"The case went too far and out of hand. I'm innocent. But their 'witness' can't be proven wrong. And they think I should spend some time behind bars."

Her brother interrupted, "Your bus ride will give her enough time. They can't stop the bus even if the transport guards figure you out. They don't have the authority to do anything. They can only transport. But the prison officials will get you back."

I don't think they'd care. What if they are corrupt? They might think it's funny to keep me. They might consider keeping me in Angel's place, tit for tat. Terrific! I don't need 'forced feminization' by some washed up prison doctor. I have a life. I don't want to someone's playmate.

Angel picked up her purse. Her brother scooped up the folder, my purse, and the duffle bag.

Before walking out, she turned and said to me, "I'll catch up with you when the time is right. I hope you'll forgive me. I do want to see you again."

"Yeah. We must do this again."

Her brother signaled the guard to open the cell, and they both walked out.

Again, the door shut with a heavy, metal, lonely, dungeon ring.

My feet are starting to hurt.

But I can't get to the ankle straps to take them off. I'm shackled in handcuffs, leg irons, and now my shoes. I'm stuck behind a secure door, helpless, and with no identification, except the number on my back.

This looks really bad.

And my only hope just got away.

Real Identities

Christine, the in charge of the women's population, was standing in front of the monitor, watching. Angel was led by her brother and joined her.

"She's just sitting there for the most part," Christine started. "She keeps rotating her feet, though. I think her feet are starting to hurt."

"Mine were too," Angel replied. "But she doesn't seem to be in a panic over the new situation, yet. She calmed down when we removed her from the group."

"She seems too stunned and afraid to speak up," commented Angel's brother.

"Thank you for allowing this. It has been fun," Angel said to Christine.

Christine turned to Angel's brother. "We will have to make sure it just looks like a simple mistake. Or we will be in a lot of trouble. But you're right, Angel. This has been fun. In all of my years as a, well, in my favorite hobby, I've never been involved in something so public and 'official'."

"Sheralyn couldn't take her eyes off of you," Angel mused.

"Interesting," Christine commented. "I have an idea. But you two need to bring her car and 'stuff' up here and then leave her to me. I want to continue this," she suggested. "We'll see just how much she knows about herself and what she really wants."

At first Angel was reluctant, but she and her brother agreed and left.

"Well, you missed the bus. So I have to take you to another cell for the mean time," the female guard said, point blank. She took me from the processing cell to the jail cells.

The walk seemed it'd never end. I'm sure the guards are used to their restrained inmates walking slowly. Trying to take those steps in heels was much harder than I had ever imagined. The female inmates there did shake me up. The taunts through the jail seemed they'd never stop. One seemed flattering though, 'Daisy Duke'. It must have stuck because even the guard used it.

After we got to a regular cell, which, to my relief, had no other occupants, she unshackled me.

Finally.

"In you go Daisy," she said smugly.

She ordered the cell door shut and strolled away.

I don't know why I never said anything. It was a horrible chance I took. I could have been locked up with someone dangerous. But the guard has probably heard it all. She probably wouldn't be interested in anything but following orders anyway. She also could have taken advantage and made things worse. So I kept my mouth shut.

I sat down on the bed and took off my shoes and stretched my feet and flexed my toes. A few other inmates were still catcalling me, to press my boobs against the bars or stick my legs through. I just lay down with my feet towards the barred cell door, glad to relieve my feet.

I lost track of time. But enough had passed that I was starting to get worried I was lost in the system and forgotten. Then I heard footsteps coming down the corridor. It wasn't the sound of comfortable work shoes or boots. It sounded like heels. And it was only one person. Although there were no taunts, some of the inmates did murmur.

So this must be someone official. Here's my chance to speak up and get out of here. Hopefully, this person will care. Where I go or how I get there doesn't matter. I'm ready to get out here and be done with this fantasy.

Still lying on the bed, I raised myself up on one hand and kept my legs crossed.

Like slow motion, a familiar black high heel pump first came into view. My eyes quickly followed up her leg to a black pencil skirt and very feminine red wool jacket. It was the businesswoman.

"Hello. I'm so sorry to keep you waiting so long. My name is Christine. Are you comfortable?"

Christine nodded to someone out of sight and the door opened. She held up one hand to signal me to hold still as she approached me on the bed. She kind of stooped and ran a finger along my top leg as she walked up and stopped in front of me.

"Okay. You need to get your shoes on," she said finally. She then held open her other hand to reveal a set of hinged handcuffs. "Also, as procedure, I need to secure your hands. I'm taking you to another area, where we'll get to know each other a little better."

You are enjoying this, aren't you?

She handcuffed me behind my back and led me to an area that looked like it was for processing those being released. The taunts and catcalls towards me had resumed. But no one said or did anything to Christine. She met another guard who held a duffle bag just like the one Angel and her brother had. She took the bag and the guard removed my handcuffs. Then she led me into one of the private rooms, where she opened the bag to reveal my purse and the clothes I took and wore to Angel's house.

"I need your jumpsuit, please. You may change in here," she flatly stated. "Do you know how to get those wonderful big breasts off?"

"No," I answered truthfully.

With that, she turned and left the room, closing the door behind her. It felt so good to change back into my clothes. I felt like myself again. The different shoes felt good, too. I even got to powder my face and get the oily shine off and perform other makeup maintenance. After a moment, Christine came back in. She held up my license in her right hand and rested her elbow in her left hand, with her left arm across her chest.

So much for anonymity.

"I know who you are, where you live, and where you work. I know your full alias. I also know you enjoyed yourself today. And I very much enjoyed your performance too. In my recreational spare time, I am known as Mistress Amber. I know how to get you off of those voluptuous breasts. Without help, it will be very painful, and obvious. But first, as my personal assistant, you will do some chores for me."

  

  

  

*********************************************
© 2006 by Sheralyn Tiffany Crosse. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.