The Softening of Jessie - Part 32

"I'm so excited Ashley! I want Jason and me to be just like old times again. I don't know why he thought I was a sissy...I don't know why he called me a fairy...all I know is that I'm going to make sure that I'm the same old Jessica that he used to love to hang out with. I'm the same guy and I'm going to prove it!"

"OK."

"Ashley, please, please, please help me with my makeup?"

Same old Jessie huh?

The Softening of Jessie

Part 32

By AshleyTS


 
"Wow Jessica! I can't believe how great that top looks on you." Ashley stated finding herself a tad jealous at the thought that he may look better in that shirt that she does.

"My bra doesn't look silly?"

"No Sweety, that's how it's supposed to look. That's the style."

"Yeah I know but I really don't want to ruin my chance with Jason. I don't think he knows I wear a bra & if he can see it through my shirt than he may call me a sissy again."

"Honey, you have breasts and that's why you wear a bra. It's a package deal ya know. Boobs equal Bra. Believe me Jessica; Jason knows you have breasts so you wearing a bra will be something he expects."

"Okay, I see your point. I do like the look by the way."

"Now on to the skirt. I think you should wear a different pair of panties & pantyhose."

"What's wrong with the ones I'm wearing?" Jessie asked.

"Well the tennis skirt I'm letting you borrow is pretty short so there may be a remote chance that you may flash your underwear if you bend over or if a breeze kicks up. When I wear that skirt I wear something that kind of blends with the skirt. I would suggest some black panties."

"I don't have any black panties though. All of mine a pretty colorful." Jessie responded.

"Well you are in luck girl cause I brought a pair of mine you can have." Ashley replied. She tossed the underwear to him.

"A thong?"

"Yeah, trust me. If you happen to bend over too far Jason will have nothing but good things to say."

"You think so?"

"I know so. Plus look at how pretty they are." Ashley replied. The panties she had given him were a pair of black thong panties with a pink bow on the upper back side.

"Well they are very pretty. I'll take your advice on Jason since it's pretty obvious I don't know what he likes."

With that Jessie pulled his pantyhose down and off and slipped off his panties.

"Oh my gosh!" Ashley gasped out loud as she saw Jessie standing there bottomless.

"What's wrong?" Jessie asked startled.

"Oh, um nothing Jessica."

"Tell me, what's wrong?" Jessie prodded her.

"It's just, well...your penis is, ummm so small. It looks like a baby's" She replied feeling sorry for Jessie. His manhood was downright man-less. To her best guess Jessie's penis must have protruded  ½ inch from his body. It actually did look like a baby boy's.

"My what?" Jessie asked.

"Your penis dear."

Jessie had a confused look on his face. That word was very familiar to him but he couldn't place it. What the heck was a penis again?

"That Jessica! The thing between your legs." Ashley said noticing Jessie's confused look.

"Oh. Yeah, my penis! Is it supposed to be big or something?" Jessie replied. Now that he thought about it, it did seem a lot smaller than it used to be. He didn't really mind that it was smaller, but he was pretty sure it used to be bigger.

"Well, not for you I guess." Ashley replied.

"Well how big is yours?"

"Sweety, I'm a girl. I don't have a penis."

"Oh." Jessie replied. He was a little cloudy on things. Ashley is a girl and that's why she doesn't have a penis. Yeah, that's right. Jessie was a boy and that's why he had a penis! He knew it would come to him!

"I'm OK now. For some reason I forgot that you were a girl or something. I'm gonna hang out with my old buddy again tonight! I can't wait!"

Jessie stepped into the black panties and pulled them up. He did a little booty shake from his excitement.

"Very sexy Jess! Now I think you need to wear these." Ashley replied as she handed him some black silky pantyhose.

"Black pantyhose?"

"Yep, they will go with the outfit you have on."

"That's kind of a big step Ashley. I mean I wear nudes because no one can tell I'm wearing pantyhose. Blacks would be like me screaming, "Look at me! I'm the boy wearing pantyhose!""

"Yeah. So you are wearing a top in which you can see your black bra peeking through, a black tennis skirt and the most feminine pair of panties I own and your concern if what people will think of your wearing pantyhose?" Ashley replied sarcastically.

"Well yeah, I don't want anyone to think I'm light in the loafers."

"Right. Try on the pantyhose and if you don't like them I won't make you wear them ok? Just try them on though." Ashley replied as she giggled athis cluelessness.

"Ok, I'll do it for you."

Jessie bunched up the nylons and expertly pulled them up around his waist. He then stepped into the skirt and zipped it up in back. It fit him perfectly!

"You look amazing Jess!"

"You don't think this is too short?" He replied concerned at how naked he felt.

"Not at all. You have great legs and you should show them off. Look at yourself in the mirror and you tell me if the pantyhose go or not."

Jessie admired his reflection. His breasts did look great in that top he thought. He loved the little flare of the skirt even if it was short. The pantyhose caused him some concern. It was painfully obvious that he was wearing them and he wasn't sure if he would get flack for being a boy wearing pantyhose. Ashley was right though, they really went well with his outfit. He fought back and forth for a few seconds before he found that his feminine fashion urges were too insurmountable to overcome.

"I love the black pantyhose! I want to wear them!" Jessie gushed.

"I knew you would. Now for the heels. These are another favorite of mine." She said as she handed him a pair of open toe 3" heels with thin straps.

"Cool!" Jessie replied as he slipped them on and buckled them. He did little walk back and forth in the room strutting his stuff.

"Work it girl! Work that runway!" Ashley teased. He had such feminine mannerisms and his walk was very enviable.

"I'm so excited Ashley! I want Jason and me to be just like old times again. I don't know why he thought I was a sissy...I don't know why he called me a fairy...all I know is that I'm going to make sure that I'm the same old Jessica that he used to love to hang out with. I'm the same guy and I'm going to prove it!"

"OK."

"Ashley, please, please, please help me with my makeup?"

Same old Jessie huh?
 


To Be Continued...

 



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