"Wow Jessie, you were such a brave girl! Your earrings look incredible too!"

"Thanks Ashley and I'm sorry for being such a cry baby."

"It's quite alright. First piercings are always rough. You were a brave girl!"

As Ashley paid for the earrings Jessie wandered out of the store in deep thought. Something wasn't right, but he just couldn't place his finger on it. What could it be? He was picking his brain trying to figure out where this deep rooted uncomfortableness came from, when suddenly... WHACK!

The Softening of Jessie
Part 18
By AshleyTS

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"So you want to know about different kinds of panties, do ya?" Ashley asked her inquisitive friend.

"Yes, you might think it's kind of weird, but I seem to have forgotten. I know I wear panties everyday, but I guess I never paid attention," Jessie replied. He felt a little odd not knowing about something he felt he should have.

"Okay, let's see...these are called boy short panties. They are just like the boring old underwear boys wear, but they are frillied and lacied up a bit," Ashley stated as she held up the almost see through panties, which were basically interwoven purple lace.

"I like those. The design on them looks cool!" Jessie said as he admired the feminine lace pattern.

"Yeah, it does look pretty cool. Now these are similar to what you are wearing, only they are sexier," Ashley said as she held up some mid rise peach colored panties which had tiny flowers stitched across the top and tiny flower patterns dispersed around. "These are for when you want to feel sexy and if you get lucky they will really turn on your ummmm... girlfriend."

"Yeah, I could see myself in those. I'd have to beat the ladies off me if they saw me sporting those babies," Jessie modestly stated.

"Oh yeah sweetie, the girls would just love those panties giggle. These my dear are called a thong," Ashley stated as she displayed the pink thong panties which had a white teddy bear eating a lollipop imprinted on the front.

"Wow, those don't look very comfortable. Isn't that like a giant wedgie all day?"

"Yeah, but you get used to it. You will probably be wearing thongs a lot. The last thing you want when you are wearing tight pants or whatever is to be showing a panty line. A thong is the best of both worlds...you have the comfort of wearing a panty without the lines," Ashley informed Jessie.

"I get it I guess. I like the bear on the front though...it's fun."

"So how about I buy you two pairs of each panty then?" Ashley offered her effeminate friend.

"That's very generous of you Ashley. I couldn't ask that much of you."

"It's alright Jessie. I want to do it. I have really grown fond of you, so please let me spoil you a bit."

"Ok, you twisted my arm. Haha," Jessie replied as his new close friend paid for the bras and panties and handed him the pink Victoria's Secret bag.

"Have a great day shopping ladies," the salesgirl said as the two left the store.

Jessie gave the woman an odd look for a moment. He felt that what she had said was not correct, but couldn't place why it was wrong. He picked his brain for a second trying to figure out why her statement didn't feel right, but couldn't find an answer. Maybe it was just her tone or something. He smiled back at her acknowledging her farewell and the two went on their way.

Ashley noticed that Jessie was taken aback a little by the salesgirl calling him a lady, but saw that he let it go as well. She wondered if he was becoming desensitized to the feminine pronouns being thrown at him as well.

"So I have an idea...tell me what you think. What about getting your ears pierced?"

"My ears pierced? No way Ashley! I think guys who have their ears pierced look gay. I'm no fag so I'll pass on that one. Any other ideas?" Jessie adamantly replied.

"Oh come on Jessie. Don't be so old fashioned grandpa. Tons of guys have their ears pierced nowadays."

"I said no... do I look a little loose in the loafers to you???"

Ashley almost burst out laughing at his question. He didn't look loose in the loafers, he looked like he should be completely out of the loafers and in a nice pair of heels!

"I'm upset Jessie. I thought you trusted my judgment. I even bought you some new bras and panties and you're going to treat me like this? I thought we were friends?"

"We are friends...it's just that...well, you think I wouldn't look too gay in earrings?" Jessie asked giving in a bit.

"Honey, earrings will not make you gay at all. In fact, they will make you even more attractive to the opposite sex. If you don't like them then you can take them out and they will heal over, so you have nothing to lose really," Ashley explained.

"Okay, let's do it then. Hurry before I change my mind."

Ashley grabbed Jessie's manicured hand and led him into Claire's. She showed him the different earrings to choose from.

"I'll buy you whatever set you want Jessie. Try to keep it under $30 though, Ok?"

Jessie surveyed the earrings, admiring the selection. The studs were nice, as were the symbols and animal earrings. The one that stood out to him though was a small gold flower with a diamond for the center. "I like the flower one right there."

"Oh I like that one too. You have great taste Sweetie."

"Can I help you two?" the salesgirl asked the two girls.

"Yeah, I want to get my friend's ears pierced," Ashley answered.

"OK, first time?"

"Yeah, first time for me," Jessie replied.

"Which earrings do you want?"

"The flower ones with the diamond center."

"Those are the most popular. Go ahead and have a seat over there and I'll be right out."

Jessie and Ashley headed over to the chair. As Jessie sat down the magnitude of what he was doing hit him. He was getting his ears pierced by a sharp needle and he began to panic.

"I'm having second thoughts about this Ashley...this is going to hurt."

"It's okay sweetie, it'll be quick and I'll be right here, alright?"

Jessie tried to hold back the tears, but he couldn't stop his eyes from welling up. The tears began rolling down his cheeks as the moment of truth arrived.

The salesgirl noticed the frightened girl as she approached the chair.

"You feeling a bit scared?" the salesgirl asked.

"Yeah, I think it's going to really hurt," Jessie replied as he tried to wipe the tears which streamed from his delicate eyes.

"It will take less than a second honey. I have 3 piercings in each ear and I am the biggest wuss there is, so if I can do it so can you. I have Christina helping me out so that we can do both ears at the same time, okay?"

"Okay."

The girls aligned the earring guns to Jessie's ears as he closed his eyes which still flowed with tears. He was wondering why he had become such a cry baby lately...ummm, because this was going to really hurt?!?

Pop! The guns shot the flower earring through his lobes and in a split second it was over. Did it really happen that fast? Wow!

"You're all done!" the salesgirl announced.

"That's it??? That didn't hurt at all!" Jessie gleamed.

"I told you it wouldn't hurt, girl. Just make sure you sanitize them daily for the next 6 weeks," the salesgirl replied.

"Oh I will!" Jessie promised as he admired his earring in the hand held mirror.

Ashley couldn't help but notice that Jessie didn't even flinch when he was addressed as "girl". First the panties and now this...he was unaware that being called a girl or a lady was not correct. She had to test this further though to insure it wasn't a fluke.

"Wow Jessie, you were such a brave girl! Your earrings look incredible too!"

"Thanks Ashley and I'm sorry for being such a cry baby."

"It's quite alright. First piercings are always rough. You were a brave girl!"

As Ashley paid for the earrings Jessie wandered out of the store in deep thought. Something wasn't right, but he just couldn't place his finger on it. What could it be? He was picking his brain trying to figure out where this deep rooted uncomfortableness came from, when suddenly... WHACK!

An elderly couple pushing a mall shopping cart ran straight into Jessie hitting his right knee, which caused him a considerable amount of pain.

"Ohhh Ouch!" he cried as he bent down to grab his knee. "Why don't you watch where you're going?" he angrily yelled at the elderly couple. They should be glad that they are old, or else he would have pounded the guy into the pavement. As he grimaced in pain the tears once again began to uncontrollably flow.

"We're sorry young lady, but we didn't see you. I hope you're all right dear," the old woman sympathetically stated.

"Hey, are you OK? What happened?" a strange boy intervened. Wait, it wasn't a stranger. But instead, it was the boy who was so nice to Jessie earlier that day. He was the only boy who didn't want to kick his butt for being with such a pretty girl as Ashley.
 

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To Be Continued...