The Softening of Jessie - Part 16

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In Jessie's clouded head, he assumed that all these men who were looking him up and down were trying to size him up to kick his ass, since he was with such a pretty girl - a pretty girl they wanted for themselves.

"What are you talking about? I just want to chat with you a bit, if that's cool," the boy explained.

"Really? Yeah, that's cool. I'm surprised you aren't like the rest of the guys in here. They keep looking me up and down like they want to kick my ass or something," Jessie expressed.

"Well, I'm sure they want to do something to you, but you can rest assured that it's not kicking your ass. I apologize for my gender...men can be dogs a lot of the time. I'm Scott by the way."

The Softening of Jessie

Part 16

By AshleyTS


 
"What are you thinking Ashley?" Jessie asked. He knew she was always full of great ideas.

"Well, seeing that you enjoy wearing your pantyhose so much, why don't we just buy you some shorts? Then you can keep your nylons on?" Ashley plainly stated. She knew it would not be hard to convince her feminine friend to take this leap.

"I don't know. Are you sure you that people won't be able to tell I'm wearing pantyhose? I don't want to take the risk and look like a sissy, cause boys don't wear pantyhose after all."

"Listen silly, you're wearing 'nudes' which means that when you have them on it looks like your legs are nude, which means you can't see the pantyhose. Get it?"

"Yeah, I got it. I just wanted to make sure. Ok, I will try on some shorts then."

The two headed into Charlotte Russe and Jessie found himself surrounded by nothing but womens clothes.

"What do you think of these?" Ashley asked as she held a short pair of plaid shorts against Jessie's waist.

"Hey, those are girl shorts. In fact, everything in here is girl's stuff. Let's go to Old Navy or something."

"Absolutely not Jess. You can't wear boy's shorts when you have pantyhose on. That's just dumb! Think about it Jessie... when is the last time you saw a boy in pantyhose wearing boy's shorts?" Ashley asked, not really knowing where she was headed with this one.

"Ummm, I don't think I've ever seen a boy in pantyhose? Or girl's shorts???"

"Exactly! So make a decision. Either wear the girl's shorts, which don't even look like girl's shorts cause they are plaid, or take off the pantyhose, so we can go get some boy's shorts. Personally, I think you are being ridiculous and am a little hurt that you don't trust my judgment," Ashley emotionally replied trying to tug at her friend's heart strings.

"Hey, don't get upset sweetie. I guess I could try them on...I mean they really don't look that girly."

"Great! Here, go into the dressing room and come out to model them."

Jessie went into the dressing room. He felt a little awkward being in a girl's area and figured the sooner he got his shorts on the better. He closed the door behind him and pulled his jeans off. They were a struggle to get off, being as form fitting as they were.

Jessie quickly tugged and pulled his pantyhose back up and stepped into the shorts. Once again he was amazed at just how well the shorts contoured to his body. The hips fit snug but the waist did as well.

"Dang, these are really short," Jessie thought as he surveyed the shorts. They were a white, yellow, and peach plaid design with two mini pockets up front and none in back. The bottom of the shorts ended several inches above the knee and exposed a lot of leg.

"Are you coming out or what?"

Jessie reluctantly stepped out of the room and into the store.

"Well well well, look at you. You look fantastic babe!" Ashley showered Jessie with praise. He looked amazing. Since when did he develop such nice legs?

"You don't think the shorts might be too short?" Jessie asked with a concerned tone.

"Not at all. At least you won't be hot right? I'm glad to see that you have on sheer pantyhose as well...good call. Hey Jess, have you been shaving you legs or what?" Ashley asked with a giggle.

"Ummm, yeah. I shave them every week, but the hair doesn't really grow back. So I look okay then?"

"Yep, I already paid so let's go eat!" Ashley said as she grabbed his hand leading him out of the store.

"Thank you ladies!" the salesgirl said as they exited. Jessie turned and wondered who she was speaking to, only to find her looking directly at him. That was odd. "The poor girl is probably just used to saying that, since mostly everyone that comes in the store is female," he thought.

As the two headed over to the food court Jessie once again became uncomfortable with the fact that men seemed to be staring at him. In fact the problem had grown much worse all of a sudden and he noticed some men who would turn around and follow him and Ashley for a while.

Ashley on the other hand was finding the whole situation very amusing. She glanced a stare at him and could plainly see why he was getting so much attention.

Jessie was all legs in his short plaid shorts and unbeknownst to him, it was very apparent that he was wearing pantyhose. Ashley could see the glossy shimmer from the nylons, which encased his silky smooth legs. His open toed sandals showcased his rosy toes, which peeked through their nylon veil. The stitch, which ran across the front of his toes, was indeed a dead give away that those pretty legs were nylon clad.

That, however sexy it was, was not the highlight. It was the way he carried himself that was making the men stumble over themselves. He was unaware at just how feminine his gait had become. He walked in long strides, with one foot before the next, and a nice little sashay to his ass. He would be ready for the runway before he knew it.

"Have you noticed that a lot of guys seem to be staring at me Ashley? It's making me very uncomfortable. Why the heck are they doing that?" Jessie asked, being rather confused.

"They are staring at you cause you are with the prettiest girl in the mall silly. They all wish they were in your place," Ashley replied with a wink.

"Wow, is this what it's like being with you? All these guys want to kick my ass then?" Jessie countered feeling nervous about his well being.

"I don't think you have anything to worry about sweetie. I'm going to hop in this store for a minute to say hi to my friend. You can wait out here. I'll be right back."

Ashley disappeared into the store, leaving Jessie to fend for himself. He noticed that every guy that passed him by looked at him. Some tried to be inconspicuous, with a little glance here or there, while other obviously stared at him up and down.

"Dang, every guy in here is jealous of me since I am with Ashley. I'm so gonna get my ass kicked today," he thought.

"Are you ok? You look worried," a strange boy said. He appeared out of nowhere, but now was right in Jessie's face.

"Umm, I'm fine. Look, I'm just friends with her ok? We just came here to hang out and stuff, but that's it," Jessie nervously explained to the stranger. He really did not want to get a whuppin'. In Jessie's clouded head, he assumed that all these men who were looking him up and down were trying to size him up to kick his ass, since he was with such a pretty girl - a pretty girl they wanted for themselves.

"What are you talking about? I just want to chat with you a bit, if that's cool," the boy explained.

"Really? Yeah, that's cool. I'm surprised you aren't like the rest of the guys in here. They keep looking me up and down like they want to kick my ass or something," Jessie expressed.

"Well, I'm sure they want to do something to you, but you can rest assured that it's not kicking your ass. I apologize for my gender...men can be dogs a lot of the time. I'm Scott by the way."

"Oh hi, I'm Jessie."

"Jessie, is that short for something?"

"Nope, just Jessie," Jessie replied, wondering what Jessie could possibly be short for.

"What school you go to Jessie?" Scott asked the very pretty girl.

"Northern High. You?"

"No way, I go there too. You sure you go there? I certainly would have noticed you walking the hallways," Scott replied feeling a bit hard thinking of her and the way she carried herself.

"Well I've been out of school for a little bit, cause I've been sick, but I'll be back soon."

"Are you Ok? What was wrong with you?" Scott asked in a concerned tone.

"Long story, but to put it simply my chest had an infection and it kind of swelled up and stuff."

"Well your chest looks perfectly fine to me Jessie. I don't have any complaints," he replied in a flirty tone as he glanced at her beautiful bosom.

"It's getting better I think and thanks," Jessie responded and found himself blushing a little for some odd reason.

"Alright Jessie, let's go have lunch!" Ashley said as she came out of the store and grabbed his arm.

"Err, ok. I'll talk to you later Scott," Jessie quickly yelled as Ashley pulled him away from his new friend.

"Bye...I guess we'll meet again at school maybe," Scott replied as he watched Jessie walk away. He couldn't take his eyes off her butt as it swished from side to side as she vanished in the crowd.

"Damn, now that's one piece of ass I'd like to get my hands on," Scott thought.
 


To Be Continued...

 

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Comments

I think that was very cruel

I think that was very cruel of Ashley, as she set Jessie up by leaving her outside the store, which allowed her to be accosted by Scott. Now knowing where Jessie goes to school Scott can make life very miserable and dangerous for Jessie, just by mentioning his meeting of her in the mall, as no-one will know who the female Jessie is, jsut the male Jessie.

Jessie

I am really enjoying this story. Just wondering how it will end.
May Your Light Forever Shine

    Stanman
May Your Light Forever Shine

jessie is so lucky

wow i also think that this segment of the storey is unfair, not to jessie , i would give any thing to be living his life soooo lucky . it is unfair that the next chapter is not here to read today !!! God i luv this storey thanks for sharing

Patty