Sissy Lauren Pt. 01

Chapter One: Adjusting To Prison Life

On a cold day in September, Freddie Jones sat on a bus on his way to prison. He had been caught four months ago and had recently been convicted to five years' imprisonment on a charge of armed robbery. He was not your typical criminal. He was just a scared young, 23-year-old man who had not wanted to risk upsetting his so called friends, who had all traded shorter sentences in return for telling the court that Freddie had been the mastermind behind the robbery.

From a young age, Freddie had simply tried his best to go unnoticed. At 5'5" and weighing only 120lbs, Freddie didn't possess the physique for standing up to people. Because of this, Freddie had developed a very submissive personality and seemed to rarely have any say in activities him and his friends participated in. That is how Freddie found himself with a gun in his pocket standing in a bookmaker's whilst his friends attempted to rob them blind. It's also how he found himself being charged as the main conspirator in an armed robbery charge when in fact he had been too scared to even withdraw his gun.

As the bus drove through the country side, Freddie stared out at the fog rolling over the hills, thinking about how he had never been more scared in his life. He had no idea how he would cope on the inside. Hopefully he could get a single cell and go just as unnoticed as he has once gone through high school. The feeling of fear grew as the prison came into sight and it seemed to peak as the gates closed behind the bus and the armed guards flocked around, ready to take control of the Freddie and the men around him.

As the men stepped off the bus, they were cuffed together and escorted into the main building. The men were then lined up and unchained. The chief guard called the names of the men and one by one, they stepped forward and assigned a wing. Freddie stared at the floor, a million thoughts running through his head.

"Jones, Frederick", boomed the voice of the chief guard, snapping Freddie back into the real world. He slowly edged forward. The chief guard looked down at his clip board and back at Freddie. "Block E".

Another guard then escorted Freddie off to his left where he was stripped and hosed down. The guards teased him about his smooth body and small penis. Freddie had not been teased much on the ride in. it seems as though every man on the bus was focused on their own attempts to over-come the fear and figure out how to survive life on the inside. Freddie was able to ignore the guards teasing as he had become used to such taunts throughout his life. He struggled however, to ignore the taunts of the prisoners as he made his way towards his cell. These taunts cut deeper than those of the guards and were threatening in a sexual way. The men inside seemed to be keen to take advantage of Freddie's small frame.

For the first week, new prisoners slept in single cells and were only allowed to integrate with the rest of the prison during meal times. Freddie was pleased about this, as it gave him a chance to figure out a survival technique. By the time the new prisoners made it to their cells, it was time for lights out. Freddie barely slept that first night. He was unsure whether it had been the occasional noises emanating from the rest of the wing, the bed that was not his own or the fear that had been further encouraged by the threats of the prisoners as he had entered. Whatever it was, it made that first night a very long one for Freddie.

The first week seemed to fly by and before he knew it or wanted it, it was time for Freddie and the rest of the new prisoners to move into their new homes for the duration of their incarceration. Freddie was moved into a cell with a prisoner named Filipe. Although bigger than Freddie, Filipe was not a big man. He was only a few inches taller than Freddie and can't have been more than 20lbs heavier. Filipe was openly gay and informed Freddie that that is how he got by in prison, by giving himself to a group of larger men who protect him. He suggested that Freddie consider a similar arrangement as he was worried that he may not make it on his own.

During the first meal since the move, Freddie sat with his cellmate eating the tasteless slop that the prison tried to pass off as food. Just as Freddie was trying to imagine himself eating a nice, juicy, medium rare steak, a well-spoken white man sat down next to Freddie and introduced himself as Lewis. Lewis told Freddie that his boss, Ronnie, wanted to see Freddie the first chance he gets. Lewis handed Freddie a piece of paper. "Be here as soon as free time starts at 3pm today."

The fear that had eased away during Freddie's first week in prison came flooding back. Who the hell is Ronnie and what on Earth could he possibly want with him Freddie thought. These two thoughts consumed most of Freddie's day leading up to the rendezvous. Shortly before 3pm, Freddie asked Filipe, "Who is Ronnie?"

"Ronnie runs E wing," Filipe told him.

"So he is tough? Is he violent? Is he going to beat me up?" queried Freddie in a panicked frenzy.

"I doubt it," replied Filipe. "He's pretty calm. More like the godfather, you know? He tends to have other guys to do the physical stuff. But they won't beat you up either. Not yet anyway. He never orders and unprovoked attack and you haven't done anything that could have pissed him off, so relax. He probably has a business proposal for you. Or he may just want to welcome you to prison life. After all, you're one of the few men in this wing doing his first stretch.

The buzzer rang and the cell door rattled open. It was free time. Freddie nervously picked up the piece of paper Lewis had given him and started to make his way to the second floor. He walked along the corridor looking up at the cell door numbers. The piece of paper read 'cell 234'. Freddie was already passing cell 231. He slowed down to an almost stationary pace as he passed cell 233 and moved in front of cell 234. He gingerly knocked on the door and was immediately met with a reply.

"Come in," came a deep voice from inside. As he entered the cell, Freddie realised that Filipe was not kidding when he said that Ronnie ran E wing. This cell was three times the size of the other cells and even had its own en-suite bathroom. It was decorated like the kind of bedrooms you may see on MTV's cribs. Although, despite the size and decoration, it was still clear that this room was a jail cell.

On the bed, a handsome black man was reading a book. He was probably only in his mid-thirties despite being completely bald. The book had a plain leather cover, so Freddie was unable to make out what this man was reading. He finished the book and placed it on a table on the other side of room then picked up a magazine before returning to his seat on the bed. As soon as he got up, his 6'4" frame towered over Freddie. "I'm Ronnie," said the man.

"Freddie," Freddie replied shyly.

Ronnie invited Freddie to take a seat next to him on his bed. He opened the magazine and began going through it with Freddie. He stopped at a page and pointed to one of the models. She was a young woman in a pink teddy baby doll, with fluffy edges.

"Do you like that?" asked Ronnie.

"Yeah, she's nice," said Freddie.

"But what about her outfit?" Ronnie enquired.

"It's nice," Freddie told him.

"What would you wear with it?" Ronnie pressed.

"I don't know, maybe some stockings," Freddie replied. Ronnie gave Freddie a look suggesting he wanted him to elaborate. "White stockings, fishnet ones." Freddie continued.

Ronnie nodded in approval, "good, I'll order some".

"What?" Freddie asked.

"For you to wear," Ronnie informed him.

"What?!" said Freddie, avoiding eye contact.

"I like you, but not like this. I'm not gay you see. You're going to get eaten alive out there. But I'm willing to protect you. All I ask in return is that you become my girlfriend. I'm not saying you have to like it but I have a feeling you may grow to anyway."

Freddie was speechless. He couldn't believe what he was hearing. But Ronnie was right, he would be eaten alive and if there was one man you wanted protecting you, it's Ronnie. "You'll need a new name," Ronnie told Freddie. "From now on, your name is Lauren. Your role is sissy. You are sissy Lauren. Repeat that back to me if you accept my offer."

Freddie wasn't sure if this was a good idea but an offer had presented it and he had to act fast. "I'm sissy Lauren," Freddie said, accepting Ronnie's offer. Ronnie smiled, pleased with his latest acquisition. Lewis appeared in the doorway and took Lauren away to the library.

In a private corner of the library was a chest next to a table. On the table was a mirror, a make-up case and a laptop. Lewis opened the laptop and told Lauren, "Lauren, on here are several make-up videos, guiding you to different looks. Within six months you should have learned to apply each of these styles to yourself. For now, pick one and learn it by tomorrow morning." Lewis opened the case and pulled out a pair of pink, frilly brief panties, a pink padded bra and a long platinum, blonde wig. "Wear these until Ronnie tells you that you can wear something else," Lewis informed Lauren. Lewis left the library and as Lauren finished adjusting the wig and her bra, Freddie took a back seat as Lauren took control and began scrolling through the tutorial videos. She settled on a very simple look that was classy, with a hint of sluttiness. She first applied a layer of foundation before adding a second layer in a slightly darker shade. She then applied some rouge and some black eyeliner. Her eyebrows were luckily shaped in quite a naturally feminine shape. Lauren applied some black eye shadow and added a touch of blue eye shadow to make it pop. Lauren picked up the dark red lip pencil and outlined her lips before filling them in with a nice shade of red. Lauren was shocked when she looked in the mirror to see a somewhat attractive woman staring back at her. The wig was kind of cheap and the make-up needed a lot of practice but she still looked like a woman.

After some admiration, Lauren returned to her cell, taking the make-up bag and the mirror with her. She got the odd wolf whistle passing through E wing but word must have spread that this girl was Ronnie's. Back in her cell, Filipe was full of compliments both on Lauren's arrangement and her physical appearance.

The next day, once she had dolled herself up, Lauren went to see Ronnie in his cell where Ronnie informed her that she would be moving in. He told her that a selection of good quality clothes and wigs were on their way and should arrive within a week. He presented Lauren with a moving in present, a shiny, black cocktail dress and a pair of black, sheer, hold up stockings. Lauren hesitantly took the gifts into the bathroom and put them on over the pink bra and panties she was still wearing.

When she returned Ronnie couldn't hide his satisfaction with the transformation. "Come over here Lauren," he motioned her towards the bed. She sat down next to him and he put his arm around her. She leaned in closer and rested her head on his chest. For the first time since arriving in prison, Lauren felt safe. Ronnie lifted head and looked into her eyes. He leaned in and gently kissed her on the lips. Lauren felt strangely comfortable and kissed him back. Ronnie rested his other hand on Lauren's leg. Having never been in this situation before, Lauren followed his lead and rested her hand on his leg.

Ronnie kissed her again whilst this time removing his cock from his trousers. Lauren broke the kiss and looked down at Ronnie's penis and then back up into his eyes. She wasn't sure whether she was ready to take this step. "Just give it a kiss," said Ronnie. After a brief pause, Lauren moved her hand up Ronnie's leg and onto his cock. Even flaccid, it intimidated Lauren. It looked about four and a half inches long and it certainly wasn't lacking in width. She slowly edged herself until she her face was just centimetres from it.

Lauren looked up at Ronnie, who nodded. She looked back down to it and gave it a kiss. She slowly stroked it a few times before wrapping her mouth around the head. She sucked and lifted her lips until she was once again kissing the tip. She moved back down engulfing more of his cock and sucked up again. He had grown. His impressive member now stood 8" long and 2" wide. She managed to get half of it into her mouth before she started to stroke. "It's okay," said Ronnie. "You'll learn to take it someday. That's good for now. Why don't you give it a lick too," Ronnie suggested.

She continued to suck his cock whilst stroking the base that her untrained mouth could not yet reach. She removed her mouth and licked from the base up to the tip and back down again. Lauren engorged on his cock once more and sucked what she could before Ronnie lifted her head up. "Hmm that's good baby," said Ronnie, "but I want something else too." Lauren gulped. She was scared of what she knew was coming next. Ronnie got up and grabbed a condom and a bottle of lube from the table. He put on the condom and laid on the bed. Lauren crawled up and laid next to him, facing away. Ronnie hiked up Lauren's dress and she removed her panties. She let them drop to the floor as Ronnie applied lube to his penis and then rubbed it into Lauren's sissy pussy. As he applied the lube, he inserted a finger into her ass and Lauren let out an involuntary moan. He finger fucked her ass a bit before slowly entering the tip of his cock.

He slid another few inches into her sissy pussy and Lauren bit her lip as she tried to deal with the pain. As Ronnie pushed the last of his 8" into Lauren's sissy pussy, she yelped. "It's okay," Ronnie told her as he stroked her arm. He slowly pulled out and pushed back in. This went on for a few minutes until he could see that Lauren was no longer in pain and her sissy pussy had adjusted to his member.

At this point, Ronnie picked up the pace and began to fuck her harder. In and out, every thrust began to bring a sense of pleasure and fulfilment that Lauren had never felt as Freddie. Ronnie fucked harder, pushing his cock in as far as he could. He was fucking Lauren so hard that the whole bed moved in rhythm with his fucking. Lauren began to thrust against him, ensuring that Ronnie's cock was pushed in as far as it could go and the all but the tip was removed before the next thrust. As the pace reached a plateau, Ronnie's breathing became heavy and he stopped thrusting whilst completely inside of Lauren. She could feel him cumming and at that moment, came with him.

As his cock became flaccid, Ronnie rolled out of Lauren and removed the condom. He pulled up his trousers and looked at Lauren's cum. "Sissy girl's don't cum. You'll be locked up as soon as your cage arrives."

"Yes sir," Lauren replied.

Ronnie handed her the condom. "Here baby; your first of many treats." Lauren took the condom and paused. "Go ahead; I think you might like it." She winced and emptied the condom into her mouth. She was surprised to find that the taste wasn't that bad. In fact, Lauren liked it. She swallowed it all and even licked up the small drop that was crawling down her chin.

Ronnie sensually kissed Lauren on the lips. "You're my girl now baby," said Ronnie. Lauren smiled. Prison is meant to lock up criminals but it may just have started to free the inner woman in an innocent man.

To be continued...