The Softening of Jessie - Part 44

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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


 
“You really have no control do you? Ashley asked.

“I don’t know what’s wrong with me. My mind’s all messed up! Logically I know that I need to be out of this dress…I need to tear these pantyhose off. I know what you must think of me. I mean you gave me some shorts and a t-shirt to put on and I chose to keep the dress on. I mean you must think I’m the biggest faerie you’ve ever seen. I think I’m the biggest faerie for crying out loud!”

“I don’t think that at all. You have to give it time Jessie. Maybe the longer you are off the tapes the more you will regain your control.”

“I need to be in charge of how I feel. I can’t let this dictate who I am. Give me the bag back!”

Jessie grabbed the bag and stormed back into the ladies room. He closed the door in the nearest stall. In his fury, he kicked off his heels, pulled his pantyhose down and off his legs, and unzipped his dress and let it fall to the floor. He unstrapped his bra and took it off. He wasn’t going to let his urges control him! He pulled the t-shirt over his upper body and pulled up the shorts. They were girly but it was a big step for him. He put on the tennis shoes trying to keep his thoughts focused and clear.

He stuffed the nylons, dress, bra and heels into the bag and marched out the restroom determined.

“You did it Jessie!” Ashley stated. He looked red as a beet and seemed pissed off she thought.

“That’s right! I’ve got this Ashley… I can do this.” Jessie replied with determination.

“Ok, are there any stores you want to go to?”

“Yeah, I want to get some boy’s clothes for me to wear.” Jessie stated as he really gave every effort to remain focused on his thoughts.
 
 
As the two began walking, Jessie felt some awkwardness on his chest. Damn! His breasts jiggled uncontrollably. This seemed so foreign to him. He tried to walk more gingerly to lessen the bounce but the more he tried to lessen the wiggle and jiggle the worse it became.

Ashley glanced at Jessie and noticed that he seemed to be walking very cautiously. Suddenly she figured out why. He obviously wasn’t wearing a bra and his girls were bouncing everywhere.

“Oh Jess, did you take your bra off?”

“Yeah, I was so fired up in there that I decided to remove it.”

“You’re going to draw way too much attention to yourself if you keep it off. I know that it may hurt your ego, but you should put the bra back on. Come on, here’s old Navy.”

They entered the clothing store and headed to the men’s section.

All eyes were on Jessie. Every time he looked around it seemed that guys were looking at him. It made him very self conscious.
Jessie quickly grabbed some boy’s cargo shorts and a navy shirt. He took some boy’s briefs and with determination he went to the dressing room. Ashley stood outside keeping her fingers crossed that all would go well.

“I’m sorry, the women’s fitting room is on the other side of the store.” The male employee stated.

Ashley grabbed Jessie’s arm and led him to the fitting rooms.

“It’s ok Jessie, don’t let it bother you. I’ll wait outside.”
 
 
Jessie entered the women’s fitting room and closed the door. He removed his girl’s shorts and top. He stood there topless in his panties and observed his female form. He knew that he needed to put the bra back on, but if that was the only article of women’s clothing on his body then he could deal.

He deftly donned the bra once more and instinctively inserted his hands into the bra cups to lift his breasts into their holders.
He tore open the briefs and quickly slipped off his panties. He began pulling the boy’s underwear up his legs when suddenly they became very tight halfway up his thighs. He tried pulling them up further but everything about them was too small…the leg openings, the width of the briefs were all wrong. Frustrated he realized that his hips, legs and butt were no longer masculine and therefore did not fit in men’s underwear.

Angrily, he took off the briefs and reluctantly pulled the panties back up. He ran into the same issue with the cargo shorts which couldn’t make it past his child-bearing hips and meaty thighs. He sat there in his bra and panties and started crying. Even with his steely determination to put on boy’s clothes it was useless. He felt crushed. Why even bother with the shirt???

He put the girl’s short and shirt back on and returned to the store. With tears beginning to flow Jessie faced Ashley.

“Nothing fit…”He said choked up.

“Oh sweetie, I’m so sorry.” Ashley replied as she gave him a huge hug and held him as he came to grips.

“Come on, let’s get out of here. Want some ice cream? My treat!”

“Yeah…sure.”
 
 
Ashley took Jessie to the food court and treated him to a double scoop of ice cream. It’s funny how that seemed to lighten the levity of the situation for Jessie. His unbridled determination to not let his feminine urges control him lessened and he found himself relaxing.

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.”

As the two sat there Jessie scratched his leg. It was then that something felt odd. It started off very mild at first. They continued talking for a while but the urge kept building. His hand kept reaching for his legs. There was a growing sense of uncomfortableness that was really bugging him. Suddenly it dawned on him. He needed his pantyhose! It was like a drug…he found that he couldn’t find peace with himself.

“Ashley, I’m really feeling like I need to put some pantyhose on. I can’t sit still.”

“Jessie, just take a deep breath and relax. You can do this ok? I’m here for ya. Try focusing on something else.”

Try as he might, Jessie could not stop the building desire to don the pantyhose. It was like an avalanche heading towards him that was unstoppable.

Suddenly Jessie grabbed the duffel bag and quickly dashed to the ladies room. He pulled the pantyhose up quickly and felt a sense of rightness come over him immediately.

He sat in the restroom for a minute and realized that in his haste he didn’t bother to take off his shorts. He had pulled the pantyhose up over them. He found it pretty funny but sad at the same time.

“You ok Jessie?” Ashley asked as she stood outside the stall.

“I’m fine. Be out in a minute ok?”

“Ok, I’ll be outside. You sure you’re ok?”

“Yeah…I’ll see you outside.”

Jessie removed the pantyhose and dropped his shorts. He pulled the hose back up. No matter how humiliating it may be to be wearing such a feminine garment, he knew that he didn’t want to face that urge again.
 
 
A couple minutes later Jessie met up with Ashley.

“Oh no Jessie, why are you back in the dress again? Pantyhose & heels sweetie???” Ashley asked. He was once again wearing the sundress, pantyhose and high heels that he left the house in.

“Just leave me alone okay? It just feels good and I can think clear this way. Look, I don’t know what’s wrong with me Ashley, but these clothes are like a drug and I think I’m addicted. I mean look at me! You’re standing there in shorts and a t-shirt and I can’t think straight unless I’m wearing a dress and pantyhose.”

“I understand, it’s okay that you are wearing them. If I can do anything to help please let me know. I’ll put on a dress and pantyhose if it will make you feel more comfortable.”

“Thanks for offering Ashley but I can handle this.”
 


To Be Continued...

 

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Comments

Still don't understand Ashley

Why is she so concerned about Jessie now? "If I can do anything to help please let me know. I’ll put on a dress and pantyhose if it will make you feel more comfortable.”

Just doesn't seem in character for who she was earlier in the story. Guess she is more compassionate than I'd thought.

Maybe she had a change of heart?

Earlier in the story I believe it said the only reason she wanted to go along with it was to get back at Jessie for being so mean to her. Over the last few chapters I think she really started noticing how wrong it was to change Jessie so profoundly and decided to help change him back. I'm thinking she started feeling guilty for pushing his transformation as far as she did and this is a way for her to mitigate that feeling of guilt. I don't think the turnaround was a complete 180 so she doesn't feel completely OOC to me, but it did still catch me off guard. However, that's what the suspension of disbelief is for. It's a very useful tool when reading fiction. =)

Ashley's heart

Ashley's heart has been in the right place for a long time--she may have been leading Jessie further into femininity, but she's always been protective as well. For instance, she could tease, but she would never humiliate. Jessie's day with Jason, leading to the handiwork, changed that--Jessie was getting into a state where Ashley couldn't offer as much protection. So the only way to protect Jessie was to try to help dial things down. At least that's my take. Looking forward to more.

Arkady71

Ashley

Does care for Jess. It took her final becoming a girl to get Ashley to repent. But will Jess hate her for her part in his change?
May Your Light Forever Shine

    Stanman
May Your Light Forever Shine

Ashley seems

to be repenting what she helped to do to Jesse. I wish he'd wake up and see her as more than just a friend.

Since Jess was hanging around with Jason, I'd suspect that they were two of the same. Is Jason really good for Jesse? Will he turn out to be a macho prick, or a "whan bam, thank you ma'am" kind of guy -- one with a girlfriend in every classroom! Is he taking Jessica for a ride (nothing intended here)?

I might add that Jason seems to need Jesse as a sex object, while Ashley appears to be a helpful, kind, caring friend. Also, "I" wish his parental unit would see Ashley as a future mate for Jesse, and encourage more closeness between them.

My two cents worth!

Annie in PA

Annie in PA