She then brushed Jessie's hair and pulled it back into a ponytail tying it with a light blue ribbon.

"Amazing! How do you feel Jessica?" Ashley asked her unmistakably feminine friend. She decided to throw out the name Jessica to see if it would stick.

"I feel great...this dress is so airy and comfortable! Why did you call me Jessica though?"

...Jessie's a Girl, and I Wanna make her Mine!...
The Softening of Jessie
Part 26
By AshleyTS

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Ashley reached into her bag and pulled out a pair of white open toe heels and presented them to Jessie.

"These will look good with your outfit. Why don't you try them on?"

"I don't think so Ashley. You're not going to get me to wear heels... those are girl's shoes," Jessie replied. He was taken aback from the offer.

"Oh come on Jess, you can't wear a pretty dress and sneakers! Get real sweety. You need to complete the outfit. Besides, these shoes will show off your pink toes...you want that don't you?"

"Ummm, yeah that would be nice, but I'm not wearing girl's shoes. That's where I draw the line."

"Hun, you're wearing one of my dresses, so I don't think the heels are that much of a leap. Fine then, if you're not going to wear the shoes then take off my dress and give it back," Ashley countered.

"You want me to take off the whole outfit?" Jessie asked. He had grown fond of his borrowed dress.

"Yep, you can walk around in your shorts and pantyhose for all I care. You make the choice. I'll let you wear the dress if you put on the shoes... or else the whole outfit comes off."

Jessie thought about the ultimatum. He really liked how the dress looked and felt and didn't want to give it back. He decided he would compromise and wear the shoes. The thought of showcases his well painted toes was very appealing as well.

"Okay I guess. Give me the shoes," Jessie replied as he grabbed the shoes and slipped them on. They were very delicate in nature with thin straps and a high heel in back that made him look tall. He thought it was pretty cool that he could grow an inch or two just by putting on a pair of shoes.

"Wow, sexy girl!" Ashley said as she admired how well the heels looked. "It's a good thing we are about the same foot size huh?"

"Yeah, good thing," Jessie said sarcastically acting like he didn't like the new shoes he had on. He admitted to himself however that they did look really nice. He liked how he could see his nylon covered toes through the open straps of the heels.

"Stand up and see if you can walk in them Jessie."

"Ok, he we go." Jessie got up and proceeded to walk from one end of the room to another without a misstep. It was as if he had been wearing heels for years. Ashley was amazed at how gracefully and feminine he sashayed from one end to the next.

"You are amazing Jess! Are you sure you haven't worn heels before?"

"Positive...not bad huh?" he replied as he did a twirl in his pretty dress.

"Look at you! You look amazing! Now let me just put a little makeup on you and then we're done," Ashley said as she got her makeup bag. When she returned she noticed Jessie sitting on the edge of the bed with his legs crossed and his back slightly arched back with his hands folded on his pantyhose covered knee. He had such incredible female etiquette.

"You sure you haven't worn a dress before? You really know how to sit properly."

"What do you mean?" Jessie replied. He was not aware he was sitting in any way out of the usual.

"Well keep sitting the way you are now whenever you wear a dress. The last thing you want is for people to be able to look up your skirt."

With that Ashley applied a little eye shadow, liner and a touch of shimmery lip gloss to Jessie face.

She then brushed Jessie's hair and pulled it back into a ponytail tying it with a light blue ribbon.

"Amazing! How do you feel Jessica?" Ashley asked her unmistakably feminine friend. She decided to throw out the name Jessica to see if it would stick.

"I feel great...this dress is so airy and comfortable! Why did you call me Jessica though?"

"Don't know...that's my new nickname for you though...I think it sounds cute."

"Yeah, cute huh? Real cute...not," Jessie replied at her strange nickname.

"Ok, let's go get some lunch, Jessica," Ashley replied as she gave Jessie a sly wink.

"Hey, I thought you were going to wear a skirt if I put on the dress?"

"Oh yeah, fair enough."

Ashley pulled down her shorts and donned her jeans skirt. Jessie knew that he should be excited seeing such a pretty girl in her panties but he just wasn't feeling it.

"Ok, let's go girl."

The two headed downstairs to head out for lunch and ran into Amanda and Susan.

"Hey mom...grandma, we are going to go out to lunch."

The two ladies stood there speechless at what they beheld. Sure, Jessie had been growing more and more feminine as the weeks passed, but this was a shocker. What they beheld was a beautiful young woman wearing a pretty dress, high heels, a cute ribbon in her hair and shimmery makeup. What was even more amazing was how oblivious Jessie was to the changes that had taken place and the clothes he was wearing.

"Honey, that's a very pretty dress you have on," his mom commented.

"Thanks mom. Ashley is letting me borrow it, which is something big since she says she is so possessive of her clothes," Jessie joked.

"Yeah, I decided I'd be a nice person and lend her it. I even put on a skirt to make her feel more comfortable with her dress," Ashley replied freely using the feminine pronoun.

"You're lucky to have such a nice friend Jessie. How do you like wearing a dress...and high heels even huh?" his mom asked.

"I think I like it mom. I don't think I've ever worn a dress before. If I have I can't remember. Is that weird...I mean I must have worn dresses before right? How come I can't remember...did I wear dresses or skirts when I was a little boy?" Jessie asked rather confused at why he could not remember wearing any dresses or skirts. He could not connect the dots that boys do not wear dresses.

"Honey, yes you wore dresses all the time...it's ok if you can't remember though," Amanda replied. She didn't know what to say to that question so she decided to change the subject.

"You really fill out the top of that dress Jessie...you may want to be careful when you lean over," Amanda stated as she noticed his very full looking breasts which were showcased in the low cut front of his dress.

"Oh...yeah," Jessie said blushing. "Ashley let me borrow one of her strapless bras. I think it pushes my breasts up more than my usual bras."

"Your breasts Jessie?" Amanda asked. Did he realize and accept that he had breasts?

"Yeah, my breasts mom. You could see my bra straps, so luckily, she had a better bra for the dress."

"Yeah, I also told Jessica that those boobs are powerful tools," Ashley butted in.

"Jessica huh?" His mom asked.

"Uhhh, yeah. That seems to be Ashley's new nickname for me...pretty lame if you ask me."

"I kind of like it and yes your breasts can get you a lot of things honey. You have to be careful how you flaunt them though because you don't want to develop a bad reputation."

"I have no idea what you're talking about mom...and I don't want to know."

"Well you two have fun at lunch then and be careful in those heels Jessica," his mom replied.

"Hey! You calling me that name too Mom? Yeah yeah yeah, rub it in. See what you've done Ashley?"

"Yep, get used to it sweety. I think that nickname's gonna stick."
 

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To Be Continued...