Sissy Lauren Pt. 02

Chapter Two: A New Girl

It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie.

Lauren had now learnt how to apply her make up to the style of most of the instructional videos she was shown back when she was first transformed. This pleased Ronnie, as did her now impressive range of clothing (all female of course). Ronnie had even managed to get her two pairs of shoes; a pair of four-inch pump stilettos, clear like a stripper and a pair of knee high, three-inch black leather boots. Lauren was progressing so well over such a short period of time that she could walk fairly confidently in both pairs. Although, there isn't much else to do in prison.

Lauren had grown to love her position. There were so many perks. She never got picked on. As a weak, small framed man, Freddie would have been a punching bag every day, for sure. But as a sissy, more specifically, the boss' sissy, Lauren was the envy of every prisoner in 'E' wing. Of course, there were down sides. As promised, a week after her first night with her boyfriend, Lauren's cock was locked away in a chastity belt. This was a stroke of genius from Ronnie as it made Lauren hornier than ever and incredibly eager to please her man.

Ronnie was a great boyfriend too. He always made sure Lauren had anything she wanted. If she wanted a book or a food of some kind, within 28 hours, she would have it. For Christmas, Lauren asked Ronnie for a pair of diamond earrings, which Ronnie was unable to procure. He instead released Lauren from chastity and allowed her to cum. Twice. He didn't even make her lick up the second load. The biggest surprise to Lauren though, was that she was never forced into sex, as she feared she may. Ronnie only ever fucked her if she was willing. Which, in her chastised state of arousal mixed with her joy of safety in prison, she was nearly always willing.

Today was a special day for Lauren. She had been given an incredibly special task. A new prisoner was being transferred to 'D' wing. Ronnie had decided recently that he wanted to make peace with the inmate running 'D' wing, a man named Kyle 'smiles' Stanton. Stanton had earnt himself the nickname, along with a 10-year stint in jail for carving a smiley face into the abdomen of anyone who betrayed him. Ronnie and Kyle had been rivals shortly before being locked away.

Lauren was to train the transferring prisoner into a fellow sissy. That sissy would then be the olive branch extended Kyle's way. Lauren wandered into her cell, beaming with excitement. She stripped off her short, denim mini skirt and white spaghetti vest. She was now standing alone in her cell wearing nothing but blue silk brief panties and a matching bra. Lauren laughed to herself for a moment. She would never have thought, from her first, sleepless night here, that she would end up in this position. Even more so to consider that she felt safe enough to leave the door wide open whilst she stood there, so seductively dressed.

She picked up a pair of opaque, black, seamed stockings and rolled them up her smooth legs. She then picked out the black cocktail dress that had been one of Ronnie's first gifts to her. She needed to look a touch classy today, as it was her first day meeting and training the new sissy. She looked in the mirror as she reapplied a coat of red lipstick before heading off to the prisoner's cell.

As she approached the cell door she spotted Ricky, one of Ronnie's guys, outside the door. "Hey sexy, you here for me?" he asked.

"You know Ronnie would disapprove," she told him as she reached the door.

"Shit," replied Ricky. "I'd let all the guys in here beat me up for a piece of that ass."

Lauren blushed and made sure to shake her ass as she entered the cell. She closed the door behind her to be alone with her project. On the bed in front of her sat a black male, who had a beautifully feminine face and gorgeous, plump lips. She could see why he was chosen. The man stood up and was about the same height as Lauren when she wasn't wearing her heels. He was young too. Probably a teenager, Lauren later found out that her trainee sissy was incarcerated not long after his 19th birthday.

"Hi, I'm Nathan," came this camp voice from the sissy to be. He held his hand, which Lauren shook. She was so used to her sissy role that her handshake was now limp, weak and incredibly feminine. Nathan stayed standing with a nervous grin on his face. Lauren got the distinct impression that perhaps unlike other prison sissies, Nathan had volunteered himself.

"Sorry hunny," said Lauren. "Nathan doesn't exist anymore. You need a new, more appropriate name," she giggled. "Do you have a girly name?" Lauren asked him. He shook his head. Luckily Lauren had been thinking about this for a while and had already prepared a few possible names. It was just about deciding which one felt right when she saw her trainee. She had it. "From now on, your name is Brandi, with an 'I'. It's sluttier that way," Lauren winked at Brandi who was visibly excited at landing a new, sissy name.

Lauren then handed Brandi a gift. She lifted up the hem of her dress and removed her panties, revealing her caged clitty. Brandi's eyes were immediately drawn to Lauren's cage and for the first time, there was an element of fear in Brandi's eyes. Lauren noticed this. "Don't worry sweety. It's really not that bad. You hardly notice it after a while. And it lets us sissies do things we might normally bail out of," she informed Brandi. "Here," continued Lauren. "Put these on," she said as she handed over her lacy pink thong. This brought back the excitement for Brandi who wasted no time in sliding them up her legs and over her semi erect cock. "That's my gift to you," said Lauren. "So, let's get started."

After a short walk to the library, Lauren sat Brandi down at the desk where she had been sat some months ago. The computer and makeup set were both set up and waiting. Lauren explained that she would be there if Brandi really got stuck, but it would be best if she learnt it all herself from scratch, the same as Lauren had done.

After a couple of hours, following a few failed attempts, Brandi emerged. She had opted for the Cleopatra style eyeliner, with green eye shadow, bright red, sissy lips and a bit pf rouge to colour the cheeks. "Wow, hello sexy!" Said Lauren. This made Brandi blush. "I think Brand needs to come with me and learn how to be a sissy." They headed back to Ronnie's cell and he was immediately impressed. Lauren spoke quickly, "before you say anything, I'd like to ask you to be unlocked sir. I would like to teach Brandi properly."

"Ok. Not sure how much teaching you can do with that little clit but give it a go. Damn! Kyle's a fool if he doesn't find you attractive. Brandi, was it?" Ronnie asked.

"Yes sir," she shyly nodded.

Ronnie pulled the key from the chain around his neck and unlocked and removed Lauren's chastity belt. "As soon as you're done, you clean up and put it straight back on. I'll leave it here," said Ronnie, placing the chastity device down on the window sill. "I'll leave you two gurls to it." And with that Ronnie left the cell, closing the door behind him. They were alone.

Brandi shyly looked at Lauren, hoping to one day be as beautiful as her. "Let's get to work," said Lauren excitedly as she pointed at her clit. Brandi wasted no time in dropping to her knees and holding Lauren's growing dicklette. She looked up into Lauren's eyes and Lauren smiled down at the sissy in training and nodded, encouraging her to go ahead. Brandi kissed the tip of Lauren's cock. "Good girl," Lauren was impressed, "not many people instinctively kiss the cock. It shows real submission and gratitude. Well done. Let's see what else you're a natural at." Brandi then licked up and down the shaft. Lauren's cock was now fully erect and she noticed that it had shrunk down to 3.5 inches. That was ok, she thought. She had grown to enjoy her lifestyle and saw it simply as the price she paid for a safe time in prison.

Brandi's lips sunk over the head of her cock and she sucked hard. This excited Lauren and Brandi could tell, the moaning had taken away Lauren's poker face, not that she was trying to conceal her emotions. Brandi was pumped with lust and the moaning had encouraged her further. She placed her hand on Lauren's shrunken ball sack and began to fondle it. This was too much! Lauren had not cum in a long time and she was very sensitive. Brandi felt the twitching in Lauren's cock and leant her head back, stroking the shaft all along. Lauren aimed and let go. Two drops of cum spurted out and into Brandi's mouth. Brandi licked her lips, smothering her sissy tutor's cum all over. Lauren knelt down, "sissies share," she winked and proceeded to French kiss Brandi. They both swallowed once the kiss was broken. "Now for the rest of your training. And if you do well, I'll play with you too." Her seductive tone drove Brandi wild with lust. She moved her body, unable to contain her excitement.

The snowball kiss had done enough to ready Lauren's little member for another round. She went over to the draw where she knew Ronnie kept the condoms but decided against it. If she managed to produce anymore cum, it should be used to give Brandi her first cream pie. She didn't need any lube, her clitty was nice and wet from what had just happened. "Assume the position," ordered Lauren, excited to have some power for the first time since she had been arrested.

Brandi knelt down by Lauren and Ronnie's bed and lent forward, sticking her gorgeous chocolate ass in the air. Lauren couldn't wait, the power play was enough for her to regain some masculine feelings of lust. She gently eased the tip pf her cock into Brandi. It was tight, but it slid in fairly easily. Lauren was now understanding more and more why Brandi had volunteered for the position. Lauren slowly pushed the rest of her cock into Brandi's sissy pussy, enjoying every little inch. Once her member was fully engulfed in the new sissy's pussy, Lauren paused to enjoy herself. She wanted this moment of power and masculine lust to last just a little longer. Whilst she had come to love everything about her sissy lifestyle, she did not know how much of her old life she missed until this moment.

Brandi moaned in anticipation and ground her ass onto Lauren's body. She didn't want to keep the trainee waiting any longer. She pulled out most of the way, slowly, before easing back in. This went on for a few minutes, the pace slowly building. Eventually Lauren was thrusting as hard as she could, moving Brandi in the process, who was keenly meeting each thrust with a counter thrust of her own. God this sissy is amazing, thought Lauren. That Kyle is one lucky man. Lauren was fucking away her own masculinity, knowing that once this was done, she would be chastised again, probably until her birthday, which was another four months away. She was going to enjoy this. She rested, fully inserted in Brandi's pussy. "Roll over," Lauren requested. Brandi complied, and without ever letting Lauren's clitty leave her body.

Lauren pulled back and thrust in. As she thrust in, she leaned down and passionately kissed Brandi. Her lust was amplified by the fact that Brandi's very erect clitty was now rubbing against her stomach. She fucked her for a few more minutes. Fast and slow. Always kissing every few thrusts. Lauren knew that she would not last much longer and so, in an effort to climax together, began stroking Brandi's clitty. They both moaned and squealed like women, which turned them both on even more. Then it happened. Hey both climaxed at the same time. Brandi threw her head back in exhaustion whilst Lauren rested for a moment, letting her clitty soften in Brandi's ass. Lauren scooped up Brandi's cum and fed it to her, making her suck her fingers. Brandi's clit twitched as she did this, she was clearly born for the sissy life. Lauren got out a fresh pair of panties and pulled them most of the way up her legs. She quickly grabbed a tissue and cleaned her clitty off. Then she fetched the chastity device and as promised, locked herself away. She finished pulling her panties up and pulled down the hem of her dress.

"Oh my god," said Brandi as she got herself dressed again. "That was amazing. I love you Lauren."

Lauren kissed Brandi on the cheek. "And I love you little Brandi, but now you love Kyle. He's your owner in here now. And I know first-hand that you will not let him down." Lauren knocked on the cell door and called out, "we're finished."

A few moments later, the door opened and Ronnie entered. He walked straight over to Lauren and stuck his tongue down her throat. "Hey baby, is she ready?"

"Yes!" replied Lauren. "I wish you could have seen us."

"So do I," said Ronnie as he rubbed his crotch. "I can only imagine how hot my two sissy sluts were." This comment made both Lauren and Brandi blush. "Ok, it's time for you to move in to your new cell."

Lauren quickly rushed over to her draw and pulled out a pair of pink pantyhose. "Wait," she exclaimed. She went to the bathroom and cut out a small strip. She returned, lent down and tied the small strip around Brandi's clitty. "Now you're ready Brandi," Lauren proudly smiled.

Ronnie reached down and swatted Lauren's ass firmly. "You're going to be punished for wasting materials like that. It's a nice touch but you'll still be taught a lesson."

"I know," Lauren did not stop smiling. Brandi walked over and kissed Lauren, passionately, one last time.

"Woah," Ronnie interjected. "Now you're going to have get me off before I punish you. You have become such a hot little sissy. Lauren blushed and winked at Brandi as she made her way to the door. Ricky then appeared in the doorway and led Brandi away. "Once we hear back from Kyle, we'll know if this all worked."

"She won't disappoint," Lauren insisted. "It may have taken me a few months to learn to be a sissy and to learn to like but she was born ready. And you saw her. She is one hot little chica."

Ronnie closed the cell door and sat on his bed. "You won't hear me disagreeing. Now I know said I'd punish you after you satisfy me but I think we can do both." Lauren followed Ronnie's hand gestures and knelt down next to him. She was already well rehearsed in this part and wasted no time in fishing out Ronnie's cock. She immediately began to suck like a pro when she felt Ronnie lifting her ass in the air. He then delivered a hard, swift smack. Lauren mumbled in pain into Ronnie's cock. He delivered another. This one hurt. Lauren stopped sucking and rubbed her sore ass. "Did I tell you to stop? I told we could do both," Ronnie told her. The sissy reluctantly went back to sucking Ronnie's large member for another twenty smacks. Lauren was tearful by the end and Ronnie noticed this. He pulled her off of his cock and looked her sweetly in the eye, "It's ok sissy. It's over now. You've learnt your lesson right?"

"Yes sir," sobbed Lauren.

"Good," replied Ronnie. "Let me guess, you fucked Brandi today, right?" Lauren nodded. "Well let me remind you your place." Ronnie was soft and caring in the way he said this. "You've done a good enough job that I don't think we'll need lube." Ronnie then lifted the small frame of the sissy up in the air and lowered her onto his cock. Once inside, he began to fuck her. Hard and fast, lifting her up and down on his cock, her chastity belt, flailing up and down. Eventually Lauren remembered her place as a sissy and took over the work load, bouncing up and down on Ronnie. She could feel that he was close to cumming and began to leak through her chastity cage herself. Seeing this was enough to finish Ronnie off. Lauren bounced up and down once more on Ronnie's softening penis.

There was a knock at the door. "Come in," called Ronnie.

It was Ricky. "She blew him there and then as a test. He's taken her. You're all good." He seemed not to notice the scene in front of him, or knew it was best to ignore it. Either way, his news had made Ronnie very happy. Ronnie pulled out of Lauren, sliding her panties back in place. He then stood on the bed and fed Lauren his penis to clean, which the good sissy did.

"You did good sissy," said Ronnie, smiling at Lauren. "I might have to get you some more to train. Why don't you have a lie down, you look tired." She was. She had topped and bottomed today and it had taken its toll. Lauren lied down on the bed, dreaming about the day she had just had and about how she hoped to see Brandi again. It was a true highlight of being a prison sissy. Though she wouldn't be a prison sissy forever. The parole board had already decided that she could be out in one year. She would have to be an extra good sissy to make sure Ronnie did not block it. She doubted he would though, he genuinely cared for her. But that would be then, for now, she would remain Ronnie's sissy, sissy Lauren.