"It's up to you Jess. Do you want to wear a skirt?"

"I think I do...what do you think Jason will be wearing?" Jessie asked finding himself confused about skirts, dresses and pants. Would Jason be wearing a skirt too? Jason is a boy so he can't wear a skirt. Wait...I'm a boy too but I am going to wear a skirt? Jessie's mind clouded.

The Softening of Jessie
Part 31
By AshleyTS

---

 
A while later Ashley arrived at Jessie's house. The two had a bite to eat then headed up to Jessie's room.

"So you're serious about Jason wanting to be my friend again Ashley?"

"Yep, he has been asking about you a lot. It's kind of annoying actually."

"I'm sorry but I'm just stunned. I really believed that we would never be friends again. He really despised me for quite a while. I wonder why he has had a change of mind."

"Well you've changed quite a bit over the last month or so. Maybe he has too." Ashley replied knowing full well that Jason was smitten with the new Jessie and had no idea the feminized Jessica was actually his old best friend.

"Good point. I've been wracking my brain about what I should wear tonight. I haven't been this nervous since I don't know when," Jessie stated.

Ashley admired how Jessie had become just like a girl...so indecisive about what to wear.

"Well I brought some clothes too if you want to see."

"Cool. I really want to impress Jason. Last time when he got really upset with me he commented how I looked like a sissy. I need to wear something that will show him that I'm the same old guy he used to like to hang out with."

"He called you a sissy? Why do you think he did that?" Ashley asked.

"I really don't have any idea. It was after I finished a workout and he said I looked like a sissy or a fairy or something."

"Well do you remember what you were wearing?" Ashley questioned Jessie.

"Nothing special. I was just in my workout gear. I had on my white leotard and white tights," Jessie replied trying to grasp why Jason would call him such names.

"Maybe he could see your panties peeking from under your leotard and was just making fun of you?" Ashley teased. She found it comical that Jessie didn't realize that he was called a fairy because he was a boy wearing a girl's workout outfit.

"Haha! Very funny. I don't wear panties with my exercise outfit!"

"Well then I'm at a loss why he would call you names then."

"In any case. I need to wear something that is nowhere near sissy-like tonight," Jessie responded trying to think back to what he used to wear.

"Well what do you have in mind?" Ashley asked wondering what her feminine friend was thinking.

"I was thinking of maybe my new skirt and top. Or should I wear some of my old clothes so that it will be like old times again?" Jessie asked.

"Well I don't think your old clothes will fit anymore dear so we need to wear some newer stuff. What do you think of some of this?" Ashley replied as she emptied some of her clothes unto his bed. She thought it was cute how he didn't want to look like a sissy and yet he was debating about wearing a skirt.

Ashley held up a black tennis skirt and an off white tank top.

"I think this skirt and top would look so cute on you Jessica. With your long legs you would drive Jason wild."

"Oh Wow! That skirt is really short. I like it, but is it too girly? I really can't handle Jason calling me a sissy again."

"Sweetie, the skirt is called a tennis skirt for a reason. Tennis skirts are short. As for it being too girly all I can tell you is that I have worn this same outfit out several times and not once have I been called a sissy."

"But have you worn it around guys? I mean around guys like Jason? He is really critical."

"Jason has seen me in this outfit before and has told me how great I look so don't panic," Ashley replied.

"Cool! So he must like it then. I'll wear that," Jessie beamed. If Jason liked the skirt and top on his sister than he of course would like it on Jessie.

"What are you wearing Ashley?" Jessie asked.

"Oh, what I have on. Just these jeans and this cute top."

"No skirt?"

"No why? I don't want to wear one. Skirts are overrated in my opinion."

"Well I don't know. Should I wear pants then?"

"It's up to you Jess. Do you want to wear a skirt?"

"I think I do...what do you think Jason will be wearing?" Jessie asked finding himself confused about skirts, dresses and pants. Would Jason be wearing a skirt too? Jason is a boy so he can't wear a skirt. Wait...I'm a boy too but I am going to wear a skirt? Jessie's mind clouded.

"Jason will be wearing pants dear."

"How do you know he won't be in a dress or skirt?"

"Because Jason is a boy and boys don't wear skirts or dresses."

"But I'm a boy...I'm a boy, but I wear skirts. Boy's can wear skirts right?"

"No sweety. Girls wear skirts and pants but boys wear only pants."

Jessie got very confused.

"Should...should I wear pants?" Jessie asked as his mental block slowed him down.

"Do you want to wear the tennis skirt Jessica?"

"Yeah"

"Then wear the tennis skirt. Jason will like the skirt on you. Boys like skirts."

"OK. I'll do it!"

Jessie stripped out of his clothes and stood before Ashley in his lavender bra, matching boy short panties and nude pantyhose.

"Well you're going to have to change you underwear if you want to wear this outfit. You need either a white bra or a black bra. The white bra will not really show through, but the black bra will. It looks cool if you can see a hint of the black coming through the white shirt. And yes, Jason will like that look."

"Ok, let's try it," Jessie replied as he grabbed a black bra out of his drawer.

He unhooked his bra and let his mounds hang loose without giving it a second thought.

"Wow Jessica, every time I see your breasts they are bigger and bigger."

"Yeah, this bra is a 34B and I fill it completely."

"What do think of having breasts Jess?"

"I like them. They jiggle around a lot and I can't sleep on my stomach anymore but I think I'm getting used to them."

"Well they sure are beautiful. They're almost as big as mine so I know this top will look great on you."

Jessie put on the form fitting top. It clung to his body like a second skin. The black bra was visible through the fabric providing a very feminine look.

"I luv it Jessica! You look hot!" Ashley replied.

"Cool!"

"Now let's try on the skirt."
 

---

To Be Continued...