The Softening of Jessie

----------=BigCloset Retro Classic!=----------

The tale of a rough and rowdy boy out of control who finally drove his desperate mother to trick and outsmart him, with the help of her friend, and showed him a future of living life as the opposite sex and along the way to learn a better way to be.

The Softening of Jessie

By AshleyTS

Copyright  © 2008, 2017 AshleyTS
All Rights Reserved.

This story has controversial content containing
mind manipulation that some may find troubling.
If you do have problems with it,
then this story is not for you.
This story, despite that, has a unique theme that
does deserve a reading and caused me to think
hard about the issues within...
which is why I retroed this. ~Sephrena.

Jessie was a friend,
Yeah I know he was a good friend of mine.
But lately something's changed that ain't hard to define:
Jessie's turned into a girl and I want to make her mine.

As she's watching me with those eyes,
she could be loving me with that body, I just know it.
Wish I was holding her in my arms late, late at night.

You know, I wish that I had Jessie as a girl,
I wish that she was Jason's girl!

How'd she become a woman like that?

(Apologies to Rick Springfield) ~Jennifer Brock. (Part 39 comment)


Stricken Pt 11

The tension and uncomfortable feelings dissapated as the day went on. Ryan felt a little ambivalent about what was happening to him. He knew that his last change was pretty dramatic, but he felt a sense of calm about it. He attributed it to his resiliance to remain true to himself no matter what changes occured physically to his body. He was in charge here...not the virus.

Stricken Pt 9

The first thing Ryan became aware of was that he was aware. It seemed as if he had regained a train of thought and that his brain started working after a long rest. Everything was jumbled though as he tried to piece together what was going on. Something weighed heavy on him, but he couldn't nail it down. In an effort to clarify his thoughts, he tried to structure what had transpired that would give him that stressed feeling. He thought back about school, his girlfriend...his condition!

Ashley's Magical Summer

----------=BigCloset Retro Classic!=----------

Ashley's Magical Summer
By AshleyTS

Copyright  © 2009 AshleyTS
All Rights Reserved.

“Well do you want me to be your boyfriend tonight?” The boy asked giving Jeffrey a wink.

“Umm, no thanks.” He quickly responded as he began walking again to get out the situation.

“Ouch! Dissed!” the other boy teased his friend.

Oh my gosh! They really did think they were talking to a girl! He passed!!! He closed his eyes for a moment and made up his mind to be at ease. He looked like a girl and he had to act like one to if this was going to work.

Stricken Pt 8

Ryan settled into his life and classes over the next couple of weeks. He was so accumstomed to his newer self that he seemed to forget about how he used to be.

He hadn't seen his father at all since he left the family. It was tough on his mother which really pissed Ryan off. How could his dad leave her to care for the entire house? It was very selfish of him and Ryan felt alot of anger towards his dad.

Stricken Pt 7

Ryan felt good about how his day at school went and was full of energy as he met Christina at her locker to walk home.

"Hey babe", he said as he gave her a kiss on the cheek.

"Oh hi Ryan. How was your class?"

"It was alright...", Ryan began replying when he was interrupted by a couple of his buddies.

"Whoah dude, Ryan is that you?"

"Yeah, what's up Paul?"

"You're like a miniature version of yourself. Damn, sorry about that bro. You must be like totally bummed.", Paul rudely stated.

Stricken Pt 6

As lunch rolled around, Ryan found out a definate perk of being in this class.  
Lunch was catered to the room!  

"Bon aptetit all", Ms Jacobs cheerfully said as the cart of food was wheeled in.  
It was the basic cafeteria lunch food plated up already for them.

"Why do they deliver lunch to us?", Ryan asked Todd.

"We are kept sheltered from the rest of the school as we go through out  
transiton. It's supposed to ease our social strain as we go through all of  
this.", Todd explained.

Ryan was still thrown off by Todd's feminine voice, but sort of understood why  

Stricken Pt 5

The next day Ryan woke up feeling great. His energy had returned and he felt like he could conquer the world. He took a look at himself in the mirror and almost forgot that he was a changed man. He went down for some breakfast and on his way back up his mother pulled him into her bedroom.

"Ryan, how do you feel about attending Ms. Jacob's class today?"

Ryan had decided to keep calm and play this new class as no big deal. He had developed a somewhat convoluted sense of power over his virus and going to some stupid class wasn't going to phase him.

Stricken Pt 4

Ryan was nervous. His girlfriend was on her way...what would her reaction be? He desperately wanted to appear strong and masculine. His skin had changed and he now stood a bit smaller than he used to, but he was still the guy she fell in love with. He remained the quarterback of the football team and could still be her man after all right?

The knock came. Ryan took a deep breath and swung the door open.

There stood his baby girl looking very happy to see him...with a bouquet of flowers?

"Hi baby!" she said giving her boyfriend a big hug, "I was so worried about you"

Stricken Pt 3

Ryan pried open his heavy lids. His vision was blurred as he tried to focus his sight. Blinking several times and rubbing his eyes, he found his surroundings slowly come into sharpness. Oh, it felt like he had been hit by a truck. His whole body ached. His thoughts were a little confused as he tried to think about what had happened to him to cause such soreness. Suddenly it snapped! His first fever had hit...he quickly sat up and surveyed his body. Oh crap! He wasn't ready for this.

Stricken Pt 2

by AshleyTS


Part 2


It was a restless night. Ryan drifted in and out of sleep. So much was engulfing his thoughts. The results of the test meant either life as usual or a a dramatic, world-altering change. There is no way that this could happen to him. That kind of stuff happens to other people right?


Ryan lay in bed once again. This was the third day in the last 4 weeks that he was not feeling well enough to go to school. He didn't mind missing school. What kid does? The relentless fever he felt however was disconcerting. His pajamas were drenched as was his hair.

To say Ryan was stressed is the understatement of the year. He was downright petrified. Looking at his mom and dad, he could see the sheer concern on their faces as well. Even his little brother and sister knew something was up.

The Blossoming of Billy - Part 14

“So your Mom told me that she discussed the test results with you.”


“So I’m baffled right now and that’s why we want to perform a couple more tests to see if we can discover what is causing the hormones imbalance. Could you lie back? I want to look at your genitals and make sure things are ok down there.”

The Blossoming of Billy

Part 14

By AshleyTS

The Blossoming of Billy - Part 13

Billy took a deep breath and slowly lifted his t-shirt.

“How long has your chest looked like that?!?” his mother drilled him. She beheld two small mounds on either side of his chest. That gentle swelling was a telltale sign that breasts were on their way.

The Blossoming of Billy

Part 13

By AshleyTS

The Blossoming of Billy - Part 12

“Well good. Have you noticed any changes good or bad in your strength or skin in the last month?”


“You are quite the talker today.” The doctor joked. “How about we take a look and see.”

Billy’s heart dropped into his stomach. He was going to be discovered. Crap…maybe he was just making too much of his chest. Maybe it would go unnoticed and he could just get out of here.

The Blossoming of Billy

Part 12

By AshleyTS

The Blossoming of Billy - Part 11

“Oh my gosh Billy!” Jenna said with a sense of shock.


“Your chest looks like mine…I mean not mine right now, but that’s how my chest looked when I started growing breasts.” She replied keeping her eyes transfixed on his chest.

The Blossoming of Billy

Part 11

By AshleyTS

The Blossoming of Billy - Part 10

“Shut up!” Billy angrily replied as the damn broke under the tremendous pressure. His lower lip quivered as his eyes filled with tears. He wiped his eyes but the waterworks had begun.

“Oh no, you are not crying. Unbelievable!” Eric stated. He couldn’t believe that his brother was being such a baby.

“I’m really trying and I’m just not strong anymore” Billy whimpered.

“I don’t know what’s up with you but you better shape up Billy. You’re really turning sissy on me and Dad would freak if he knew the crap you were trying to pull.”

The Blossoming of Billy

Part 10

By AshleyTS

The Blossoming of Billy - Part 9

Billy’s mind was set at ease, at least a little. The doctor would be able to tell him what’s wrong but what if it came out that Billy was taking hormones? Would the doctor be able to tell? What would he say? What the heck was wrong with Billy?

The Blossoming of Billy
Part 9

By AshleyTS

The Blossoming of Billy - Part 8

“I know. I don’t know what's wrong with me.” Billy replied with a sense of relief.

“It might be a hormone imbalance. Have you told your mom?”

“No. You are the first person I have mentioned this to. What if my mom tells my dad? I would be dead.”

“No you wouldn’t. That would explain a lot. This is probably why you are having so much trouble with your exercises. Billy, I’m not joking. Your skin looks and feels exactly like mine.” Jenna stated as she grabbed his arm and rubbed it against her arm.


The Blossoming of Billy

Part 8

By AshleyTS

The Blossoming of Billy - Part 7

“Did you boys finally start using that moisturizer I put in your bathroom?”

“What are you talking about mom?” Billy replied.

“Your skin is extremely soft or haven’t you noticed? I figured that you were using the moisturizer that I had bought.”

Billy rubbed his hand against his arm. Wow! His skin really was very soft now that it was pointed out to him.

The Blossoming of Billy

Part 7

By AshleyTS

The Blossoming of Billy - Part 5

“You look mesmerized Billy” Mom stated as she noticed him fixated on what she was doing.

“I just never noticed how at home you look in the kitchen. You are a pro mom!”

“Why don’t you come in a here and help then? I could teach you a few things.” Mom replied. She was sure that Billy would refuse. All the men in the family showed very little interest in anything that wasn’t a masculine ideal.

“Okay!” Billy quickly answered as he jumped up to help his mom.

The Blossoming of Billy

Part 5

By AshleyTS

The Blossoming of Billy - Part 4

The repercussions of someone finding out that Billy was taking hormones were just too great. What would be his dad’s reaction? Would he be kicked out of the house? The shame that would be put on the family would be tremendous. Could he get more hormones once his supply dwindled? So many questions and so much pressure!

The Blossoming of Billy

Part 4

By AshleyTS

The Blossoming of Billy - Part 3

“I don’t know what it is dad, I’m trying my best.”

“Before you finish up son, you need to give me those final 7 push-ups”

“Yes dad” Billy replied as he saved those until the end and pushed them out.

This was becoming a big concern that would have to be addressed. How was Billy going to explain the gradual loss of strength? Was he getting in way over his head? Should he call it quits on the hormones? This may not be the right time.

The Blossoming of Billy

Part 3

By AshleyTS

The Blossoming of Billy - Part 2

“OK, look kid, I don’t want your mom to be pissed off so I’ll make an exception especially if its only paper stuff. I’ll mark this as a “no sign” this time.”


Billy grabbed the package and went through the back gate. He opened the package in a hurry and pulled out the pills. It was almost surreal that he had them in his possession. He unzipped his backpack and hid them at the bottom.

The Blossoming of Billy

Part 2

By AshleyTS

The Blossoming of Billy - Part 1

“Nice dress dude!” some kids yelled as they passed by.

His heart was crushed as he ran back to the bathroom and changed into his pirate garbs. He was humiliated. After all the buildup and fantasizing he had done for this night, it ended in a miserable disappointment. Everything was left in the restroom as he went home without any candy…destroyed.

And so he lay in bed thinking of the immense urge to be a girl that seemed like such a joke

The Blossoming of Billy

Part 1

By AshleyTS

The Softening of Jessie - Part 53 Conclusion

His body was so hard and muscular. Being held in Ryan’s arms made her feel like the safest girl in the world. She pressed her breasts against his chest as their lips met for a brief moment.

Ryan was all too aware of his girlfriend’s boobs pressing against him. His eyes glanced down at them for a brief moment. They were so amazing he thought as he caught a small glimpse of her lacy bra from that point of view.

“Oops, I got a little lipstick on you.” Jessica giggled as she used her finger to wipe his lips.

The Softening of Jessie

Part 53

By AshleyTS

The Softening of Jessie - Part 52

“Jessie?” Amanda gasped as she beheld her…daughter?

“Mom! What? I thought you left!?! I know you left!” Jessie yelped as he jumped up almost losing his balance on his high heels.

“Sweety, is this what you always do when I leave the house?”

Jessie thought about making an excuse to cover this whole situation.

“Mom, this is me. I know I’m your son and everything but I really, really love being a girl.”

The Softening of Jessie

Part 52

By AshleyTS

The Softening of Jessie - Part 51

Jessie wondered if he could still ejaculate. He rubbed the nub for a minute to try to stimulate any growth. Nothing. Oh well, no big deal.

No big deal?!? He remembered the priorities in his life and his penis definitely was one of the tops. He found that he could not get upset of its diminutive size or inability to function. It just didn’t faze him in the least. What did bother him however was how odd the little nub looked on his body…hmm.

The Softening of Jessie

Part 51

By AshleyTS

The Softening of Jessie - Part 50

“Well, I used to be fueled by my temper and emotions. I would get so upset with things that I didn’t feel in control at all. All I could feel was rage and I wanted to take that rage out on others. My thoughts and emotions were way out of whack. On the other hand, now I feel very balanced emotionally. Sure I cry a lot more now but at the same time, I don’t feel that anger I used to. It’s like all my aggression has been tamed. It feels really good Ashley! I can think clearly.”

“So you like being a girl then?”

“I don’t know. I do know that I like the way my head is way more balanced now.”

The Softening of Jessie

Part 50

By AshleyTS

The Softening of Jessie - Part 49

Jessie realized how horrible he was. It’s funny how his actions seemed so wrong now that he looked back on them. How could he be so rotten to his mom, his teachers…everyone? He didn’t agree with the action taken by his mom to change him, but he did understand how she could be at her rope’s end.

“I promise you that I won’t deceive you any longer honey. I know that this is going to be difficult but I am here for you now. I will do whatever I can.”

“Thanks mom. I just need time to think about what I want to do…” Jessie replied as he hugged his mom and went up to his room.

The Softening of Jessie

Part 49

By AshleyTS

The Softening of Jessie - Part 48

“Look Amanda, you didn’t listen to me when I told you not to fall for your ex. You didn’t listen to me when I pleaded you not to marry him and you didn’t listen to me when I told you it wouldn’t last. I am right and you are wrong dear. Now listen to me now and sign the release papers. Jessica is a beautiful girl. Jessie is no longer and that’s something that you will have to deal with.”

“I don’t know mother…”

“Do as I say now! Sign the release form Amanda Lynn.” Susan demanded.

The Softening of Jessie

Part 48

By AshleyTS

The Softening of Jessie - Part 47

“This is a real concern Amanda. The conditioning your son has been under has changed him dramatically. This conditioning was essential however. I suggest that you look at this as a starting point with your daughter. Things will not be the same as they used to but that’s the price that is paid with this treatment.”

"There is nothing that can be done to bring back all the good things about my son? Is he lost forever?” Amanda pleaded.

“Yes, I’m afraid so. If he were to remember his former life now it would be deadly. His mind would not be able to cope and he would be irreversibly damaged. That is why the bi-weekly check-ins were so important. The program could have been stopped at any time during the first quarter if you wished.”

The Softening of Jessie

Part 47

By AshleyTS

The Softening of Jessie - Part 46

“Now calm down Jessica…”

“My name is Jessie. I can’t believe that you and mom did this to me. You don’t care about me at all! Did you think I would never find out?!?”

“Honey, you need to believe that we did this for your own good.” Susan replied in a panic.

“My own good?!? Changing me into a girl was for my own good??? I was born a boy and what you did to me was destroy every ounce of my maleness! How can that possibly be good for me???”

The Softening of Jessie

Part 46

By AshleyTS

The Softening of Jessie - Part 45

“What the hell Jessie?!? You freaking fag! You became a girl and thought it was cool to trick me?!? “Jason angrily asked. He was seeing red. What were his friends going to think?!? He told so many of them about the pretty girl who had whacked him off the other day. He would be the laughing stock of the neighborhood!

“You didn’t know??? How did I trick you? What happened between us?!?” Jessie asked confused as much as ever. What the heck did he and Jason do?

Blinded by rage and embarrassment, Jason lost it.

The Softening of Jessie

Part 45

By AshleyTS

The Softening of Jessie - Part 44

As they sat there licking the cones Jessie started to feel at ease. He didn’t even realize that he was sitting with his legs crossed and was postured in an identical way to Ashley.

“Things are going to be alright Jess. It is a huge step that you actually aren’t in such a zombie-like state anymore. Even if your body is different than it used to be, you seem way more like yourself now than you have been.”

“Surprisingly I feel alright right now. It’s really weird that I feel ok, but I do.”

The Softening of Jessie

Part 44

By AshleyTS

The Softening of Jessie - Part 43

Jessie removed his top and Ashley helped him slip the pretty summer dress over his head. She then zipped up the back. A tear fell from Jessie’s eye.

“I’m sorry sweetie. I know this has to be so hard for you.”

“I’m never going to be a boy again. Look at me…it’s too late. My life is over.”

“We’ll get this fixed ok??? We just need to think. Come on, let’s go.” Ashley replied as she teared up herself. This boy’s life was devastated.

The Softening of Jessie

Part 43

By AshleyTS

The Softening of Jessie - Part 42

Jessie stood up and walked to the door mirror. He gasped as he saw the pretty girl looking back at him.

He examined his face which was downright pretty. His hair had grown so much! Thin, arched eyebrows? He continued in an almost surreal-like state. Breasts. He had breasts. No denying it. He lifted his nighty over his head and just stared. How? He reached to touch them. Red painted, perfectly manicured fingernails? This can’t possibly be real... but it is! His supple breasts gently swayed as he lifted them with his hands. They were real and they were a part of him. His hips curved out so much. If the breasts weren’t enough, the hips sure didn’t lie. He had a undeniable female figure!

This just couldn't get anymore worse!

The Softening of Jessie

Part 42

By AshleyTS

The Softening of Jessie - Part 41

“So you don’t remember anything?”

“Anything about what?”

“About being a boy?”

“I’ve been a girl my whole life Ashley. You and mom are kind of freaking me out with these boy questions.”

The Softening of Jessie

Part 41

By AshleyTS

The Softening of Jessie - Part 40

He felt Jason’s hand brush and then gently grab his upper thigh. As they continued to lock lips, Jessie was very conscious of Jason’s hand which slowly crept higher and higher on his thigh until it was reaching under his skirt. Should he stop Jason? Was there any harm? He continued to passionately kiss him and got lost in the moment.

Suddenly, he could feel Jason’s hand under his skirt and around his backside. Jason was tracing Jessie’s panties with his fingers. Jessie jumped back a little. This was getting too out of control!

The Softening of Jessie

Part 40

By AshleyTS

The Softening of Jessie - Part 36

This was Jessie's chance! He slid back into Jason's lap even further to the point that his rear end pressed firmly against Jason's hard penis. Jessie thought for a second at how gay that was...but wow it felt so right! It felt eerily natural to be drawn to a guy!

Jason on the other hand was filled with a mixed bag of complete ecstasy and total embarrassment. He was so concerned that Jessica was going to be offended that he had a hard on for her. On the other hand, she did slide back into him. He didn't know what to think! She was so beautiful. He wanted to grab her ass...was she wearing panties?

...Jessie's become Jason's girl! And she's turned out fine!...

The Softening of Jessie

Part 36

By AshleyTS

The Softening of Jessie - Part 35

Jason, on the other hand, was going through the roof. He was pressing up against the beautiful girl from behind. He tried to keep his mind from wandering as he showed her what to do. He wasn't very successful as he grew very excited. He quickly tried to show Jessie how to putt to avoid the embarrassment of his growing excitement.

Jason's instruction made sense! He was so cool Jessie thought. Did Jason have a roll of quarters in his pocket or something? Jessie wondered as he felt the hardness in Jason's pants press up against his rear end. He must have those quarters to play in the arcade later Jessie figured.

"Got it?" Jason asked as he quickly backed away hoping his pretty friend didn't realize that she had just given him a major boner.

...You know, I wish that I had Jessie as a girl!...

The Softening of Jessie

Part 35

By AshleyTS

The Softening of Jessie - Part 34

She thought about how unfair it was to rob a man of his masculinity. If only Jessie had been a good boy. He was on such a bad path in life. He did seem so happy now. Sure, it involved taking away any shred of maleness, but it was worth it...right?

"I feel great mom. I'm just nervous that Jason will not like me. I just want things to be like they used to between us. "

"I'm not sure if that's possible but I hope you two can be friends again."

"Me too mom."

...Wish I was holding her in my arms late, late at night...

The Softening of Jessie

Part 34

By AshleyTS

The Softening of Jessie - Part 33

"Come here pretty girl and let me see your pretty pretty panties!"

They wrestled back and forth a little and Jessie was stunned at how strong Ashley was. He had a hard time believing it, but she overpowered him as she wrestled him to the ground.

The two rolled around for a minute and Jessie grew even more embarrassed as his skirt kept flipping up around his back.

"Aha, those panties look mighty sexy Jess!" Ashley teased as she pinned Jessie down on his back holding his arms to the ground.

The Softening of Jessie

Part 33

By AshleyTS

The Softening of Jessie - Part 32

"I'm so excited Ashley! I want Jason and me to be just like old times again. I don't know why he thought I was a sissy...I don't know why he called me a fairy...all I know is that I'm going to make sure that I'm the same old Jessica that he used to love to hang out with. I'm the same guy and I'm going to prove it!"


"Ashley, please, please, please help me with my makeup?"

Same old Jessie huh?

The Softening of Jessie

Part 32

By AshleyTS


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