The Softening of Jessie - Part 19

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"Ouch! Try to be gentler," Jessie cried, although he found Scott's touch surprisingly comforting.

"Okay, I'm just rubbing your leg to see if I can lessen the pain. It looks like you may just get a small bruise from this," he replied as he caressed her nylon covered leg. Her soft skin coupled with the silky feeling of the pantyhose was enough to send Scott over the top. "Those pantyhose you have on must be bulletproof! They saved you from any broken bones," he joked.

Just then Jessie realized that this boy had found out that he was wearing pantyhose. What must Scott think of him? Oh crap! The pantyhose were not noticeable from afar but up close they were apparent... especially since Scott was touching them! How was he going to handle this? A boy wearing pantyhose??? What if Scott got the wrong impression that he was gay? Was Scott going to kick his ass or treat him like Jason did?

The Softening of Jessie

Part 19

By AshleyTS


 
"Here Jessie, let me help you over to that bench," Scott said as he sent the elderly couple on their way.

"Good thing I was walking by here... I was just in the nick of time!" he joked with Jessie.

"Scott right? Thanks for stepping in there. I was about to go off on those two. The old guy should feel lucky I didn't pound him into the pavement!" Jessie emotionally replied.

"Well you do have spunk, that's for sure," Scott stated. He found the whole feisty, tough girl thing a turn on.

"Now where did the cart hit you?"

"On my right knee area. It still hurts pretty badly," Jessie said as the tears still flowed from his eyes.

"Where? here?" Scott placed his strong hands on Jessie's knee. "Yeah, it seems a bit swollen."

"Ouch! Try to be gentler," Jessie cried, although he found Scott's touch surprisingly comforting.

"Okay, I'm just rubbing your leg to see if I can lessen the pain. It looks like you may just get a small bruise from this," he replied as he caressed her nylon covered leg. Her soft skin coupled with the silky feeling of the pantyhose was enough to send Scott over the top. "Those pantyhose you have on must be bulletproof! They saved you from any broken bones," he joked.

Just then Jessie realized that this boy had found out that he was wearing pantyhose. What must Scott think of him? Oh crap! The pantyhose were not noticeable from afar but up close they were apparent... especially since Scott was touching them! How was he going to handle this? A boy wearing pantyhose??? What if Scott got the wrong impression that he was gay? Was Scott going to kick his ass or treat him like Jason did?

"Ummm, the whole pantyhose thing is...well...ummm...I don't know why," Jessie stammered as tears began to flow heavily.

"Hey don't cry...stop those tears okay? I was joking about the bulletproof thing. I think your legs look great in them."

"Really? So you don't think it's weird for me to be wearing them?" Jessie wondered, as his mind did not grasp the reality that he was fully clad in women's apparel and not just pantyhose.

"No. Why would that be weird? Maybe it's not pantyhose weather right now, but I think your legs look incredible," Scott replied. His hand had not moved from her thigh as he gave her leg a little squeeze. He wondered why on earth it would be weird for a girl to be in pantyhose.

"Well thanks. You are a cool guy unlike some boys I know," Jessie replied as he referred to his former friend Jason. Scott seemed just so much more mature. He could see himself hanging out with Scott and doing guy stuff. Ashley was cool, but he also needed a fellow guy to hang out with sometimes. Scott had something going for him too... was it his attitude? Perhaps it was those strong hands...and he did have very pretty eyes.

"Oh, man trouble huh? Do you have a guy in your life?"

"Well, I did have one. He started being mean to me though, so we don't hang out anymore," Jessie replied as he thought of his best bud Jason and what a jerk he had become.

"I've got an idea, I'll be your new guy and I promise not to be mean," Scott promised in a playful way.

"Really? I admit I do need to stop hanging out with a girl all the time. I miss having a guy friend to chill with and talk about guy stuff." Jessie gleamed at his new hope for a guy friend. He could play hoops with Scott, watch football with him, and play wrestle mania with him. Jessie found himself feeling a little hot and bothered as he imagined Scott's strong frame pinning him to the ground.

"Yeah? I'm cool with that for sure," Scott replied seeing that the girl was interested in hanging with him to talk about guy stuff. It was always a plus when a girl was interested in guy's things. Football maybe? He imagined her in a football jersey...and nothing else.

"Hey, did you just get your ears pierced?" Scott asked.

"Yeah, like 5 minutes ago. It's funny because it didn't hurt at all until those old people ran into my legs."

"Well they look very pretty I must say," Scott complimented.

"Thanks!" Jessie gushed.

"And I see you went shopping at my favorite store," Scott said as he noticed the Victoria Secret's bag.

"Oh you like it too?" Jessie replied. "Do you shop there often?"

Scott had to be careful with his reply. If he said yes then she may think he has a few girlfriends.

"No not really, but I do like the store. What did you buy?" Scott asked hoping she would open up and let him know.

"Ummm, I bought some different panties," Jessie replied. He didn't divulge that he also bought some bras. He didn't want his new friend to run away if he found out that he was wearing a bra. The pantyhose thing was shocking enough, but a boy in a bra would be too much.

"Wow, you have my full attention. I wouldn't mind giving you my opinion on them if ya want," Scott teased as he kept his fingers crossed that Jessie would show them off.

Jessie thought it was a little odd that Scott wanted to see the underwear that he bought, but they were both guys, so what difference did it make?

"These are my boy shorts and these are some mid cut panties. I like them because they have a little bit of lace on them," Jessie explained as he held up the delicates.

"Lace is good. Those are very nice," Scott replied as he felt himself getting very excited. His hand, which was still on Jessie's leg, tensed up a bit.

"And these are my thongs. I like the little decorations they have on front...oops!" Jessie exclaimed as one of his bras was hooked on the panty. He quickly shoved the bra back in the bag.

"I see you went bra shopping as well?" Scott excitedly discovered.

Jessie was embarrassed once again. What will Scott think of him now?

The way Jessie's brain was wired led him to believe that panties where normal to wear, but a bra was something only girls wore. He decided to fess up and tell it like it was.

"I'm only wearing a bra until these dumb bumps go away. Then I won't have to wear one anymore," Jessie explained hoping that Scott would be as cool about this as he was the pantyhose.

Scott admired Jessie's sense of humor no matter how strange it was.

"Well I'm in no hurry for those bumps to go away, so wear your bra as long as you have to. It's alright by me."

"New friend?" Ashley asked as she interrupted the two. She was surprised to see a boy with his hand on Jessie's knee.

"Oh hi Ashley. Yeah, this is Scott. We met earlier today, then we sort of ran into each other again."

"Nice to meet you Scott."

"You too. Well, I should get going then and let you two girls enjoy your shopping."

Jessie got that strange feeling once again that something was not right with that statement but he could not place it.

"Thanks for your help Scott. It was nice talking to you," Jessie said. He felt a connection to him but felt shy about asking for his phone number.

"It was great seeing you again Jessie. Do you think I could get your cell number? Maybe we could hang out some time if you want to?"

"Yes!" Jessie replied. He was so happy to have a guy friend again.

The two exchanged phone numbers and promised to call each other soon.

"He's very cute," Ashley remarked as they watched Scott walk away. "I wouldn't mind hanging out with him."

"Hey now, don't go stealing my friend. It's gonna be nice spending time with a guy again. Watch out Ashley! With him around I may go back to my old ways and get into trouble."

"Yeah, I'm sure you will. He's gonna want to get into a whole lotta trouble with you!" she grinned.
 


To Be Continued...

 

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