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


 
During breakfast Jessie kept drifting off the conversation. His mind was very pre-occupied with what was going on. He was surprised by how calm he was under these circumstances. He knew his nature. He should be up in arms right now flipping the table over, verbally abusing his mom and grandma, storming out of the house and returning when he damn well felt like it… but he wasn’t. He remained very composed and controlled in his emotions.

“Well thanks for breakfast. Come on Jessica. Let’s go get dressed for the day.” Ashley stated pulling Jessie up from the table.

Susan eyed her granddaughter as she followed Ashley out of the room.

“Amanda, did you notice anything odd about Jessica?”

“No mom, she seemed fine. I think she had a great day yesterday and is a bit worn out is all.”

“I don’t know. Not wearing a skirt? No pantyhose? It is so unlike her. It makes me worry.”

“Mom, if she doesn’t wear a skirt everyday that’s quite alright. She has been over-the-top feminine for a while and maybe she is pulling it back a little now. She’s a teenage girl for crying out loud. She shouldn’t be wearing pantyhose every single day.”

“I suppose you’re right. I may just be drawing too many conclusions.” Susan replied. She still had her concerns no matter how much Amanda tried to rationalize.
 
 
Once in the bedroom, Ashley let it out.

“That was freaky Jessie! I was so nervous that they were going to find out that your memory had returned.”

“Something’s changed about me Ashley. I really wanted to get upset and freak out but I just couldn’t. I had no desire to. I look at what they have done to me…I look at my body and I want to scream, but I don’t. It’s scary! It feels like I have boundaries that I cannot cross.”

“I don’t know sweetie, but maybe you will become more yourself the less you listen to those tapes.”

“Tapes?”

“Every night you put on those headphones and listen to tapes that affect you mentally. You’ve been on them for months.”

It made sense to Jessie. The tapes controlled his mind. They gave him the thoughts, they brainwashed him. Once again, he was way too chill about finding out this information. He realized that it was not right but had no control over it.

“Can we just get away for a while Ashley? I just want to go somewhere and think things over.”

“Okay, but we gotta do a couple things to get by your grandma though. I hate to say it Jessie but you’re going to have to put these on.” Ashley said as she held out a pair of nude pantyhose. “You can take them off as soon as we get out of the house I promise.”

“Man, what have I become??? “ Jessie replied as he slipped his shorts off. He then bunched up the nylons and donned the pantyhose as naturally as any woman would.

Ashley watched in wonder. His memory seemed like it was back. He knew that he was a boy, but there were some definite lingering effects from the tapes. The male-female line seemed very blurred.

As soon as Jessie had pulled the panty up over his waist, he felt an electric surge run through his legs. He looked down at his nylons encased gams. He knew that what he was looking at was the antithesis of masculinity, but there was no denying how fantastic they felt against his legs. I’m a boy! I AM A BOY! He felt deflated.

“We should put you in a dress too. We just have to show your grandma that you are the same Ashley she knows. I’m packing your shorts in my bag. As soon as we get somewhere for you to change you can change. Are you ok with that?” Ashley asked. She really didn’t want to hurt his male ego. Did he still have a male ego??? She saw the look in his grandmother’s eyes though and knew that all questions needed to be squashed asap!

Being in the daze from all that was going on, Jessie agreed. He knew for sure that he would be out of that dress as soon as he could. 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.

Jessie slipped his feet into some matching heels and followed Ashley downstairs.
 
 
“My my my Jessica, that’s the girl I know.” Susan said as she admired her pretty creation.

“Thanks! We’re going out for a while”

“Ok, have fun girls!”

As they left the house, Jessie thought about his family. His mom and grandma seemed so happy with his transformation. How could they be so cold? They didn’t give any thought to his feelings and desires. Well he hoped that they were happy since his life would never be the same.

Ashley glanced at Jessie as they walked. He put on those heels without second thought. It was almost as if he didn’t realize that he had done that. He still carried himself in a very feminine manner. His hips sashayed, his heels clicked, his arms gently and elegantly swayed.

“You doing alright Jessie?”

“No. I can’t control my thoughts. They are all mixed up right now… Look at my shoes!” Jessie said as it just dawned on him that he had put on the heels, “I put on high heels???”

“Yeah, I thought you knew.”

“I had no idea! I just did it without thinking!”

“Just give it time Jessie. You can’t expect everything to be normal so soon. You have to have time to adjust.”

Jessie thought about what had transpired. His last full memories were of him as a boy. Being on the soccer team, playing video games, getting into all kinds of trouble lol!, hanging out with Jason... Huh? What the heck was that? He felt flush and what the heck were the butterflies in his stomach for? He thought about Jason and there it was again! Butterflies in the stomach! He felt flush! That didn’t make any sense did it?
 
 
They approached the mall and Ashley directed Jason to the restroom.

“Ok, so you need to use the women’s room, but go in there and change. I put a t-shirt, shorts and sneakers in the bag. That should make you feel more comfortable.”

Jessie grabbed the bag and reluctantly entered the women’s restroom. He found a stall and opened the bag. He lifted the skirt of the dress and reached to remove the pantyhose. Maybe he should keep the pantyhose on just in case? No! of course he shouldn’t. Why would he need to keep the pantyhose on? I mean they did feel super nice on his legs and all but he’s a boy. Dang it! Okay, gotta get this dress off. Put on the shorts and t-shirt…much less feminine. Pantyhose, dresses, skirts? He was a boy and all of a sudden he was thrust into this woman’s world. He was not going to tolerate this.

After several minutes of fighting with his demons, Jessie emerged from the restroom feeling more at ease with his clothing.

“Jessie, you didn’t change? You saw the shorts and t-shirt???” Ashley asked being confused.

“Yeah Ashley. I thought that maybe I should wear the dress just in case someone sees me that expects me to be the girly girl.” Jessie rationalized. As girly as his outfit was, he found himself uncontrollably drawn to the feminine get-up.

“Oh Jessie, those tapes are awful. You have no control do you?”
 


To Be Continued...

 



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