The Softening of Jessie - Part 23

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"My boob...you hit my boob...and it hurt," Jessie complained once again. He didn't know why he had to repeat himself...it was pretty apparent that she had hit his breast.

"I really didn't mean to hit your breast...I know how much that hurts," Ashley apologized. She was amazed at how he suddenly was aware that he had breasts but didn't realize that boys don't have breasts.

"I know it was an accident. I was trying to take it easy on you cause you're a girl and I'm a guy but dang you don't fight fair!" Jessie said sarcastically.

"Well maybe I'm not used to the boy's I fight having boobs that get in the way," Ashley responded pushing the envelope a little.

The Softening of Jessie

Part 23

By AshleyTS


 
"Wow, you look so pretty Jessie!" Ashley exclaimed to her feminine friend.

"Thanks. I've never worn makeup before...but I think its Ok to," Jessie replied a little confused.

"Sure it is sweetie. You never want to use too much though. Makeup is only there to enhance your natural beauty."

Jessie nodded his head in agreement. What Ashley was saying made sense in an uncomfortable kind of way.

"Let's do our nails," Ashley suggested.

"I don't know. This isn't what I'm used to doing on sleep overs..."

"That's because this isn't a sleepover silly, it's a slumber party!" Ashley explained. "At slumber parties you paint your nails, play with makeup, gossip and stuff. Besides, I brought a few different colors. Don't you want to see my different colors of nails polish Jess?"

Jessie thought about what Ashley had said. He had been to a few sleep overs with his friends but he had never been to a slumber party. He always thought that slumber parties where something girls did. Hmmm, Ashley is a girl so that's why she is used to slumber parties. Besides, he was awfully curious about the nail polish shades.

"What colors do you have?" Jessie inquired.

With that Ashley pulled out her box and the two sorted through the colors until they found their favorite.

"How about you do my nails first and then I'll do yours?" Ashley asked.

"OK!" Jessie said with excitement.

He carefully, yet deftly painted her fingers the peach hue and followed with her toes. Ashley watched in amazement at how delicate and feminine Jessie's movements were.

"Wow, you're really great at that. Maybe you should work in a nail parlor Jess!"

"Thanks, I practiced a lot to get that good."

"Ok, my turn now...you're going to want to take off your pantyhose though. Polishing nails through nylon doesn't work so well," Ashley joked.

With that Jessie stood up, lifted his nightee and began pulling his pantyhose down.

Ashley noticed the panties he had on from their excursion to Victoria's secret. They were the pretty boy short panties that he so wanted. She also noticed the feminine curve of his hips and butt. One thing she found that was missing though was his penis. All she could see was a flat crotch.

"Jess dear, could you lift up you night shirt again?"

"Why?"

"Ummm, I want to see the panties I bought you...I only saw a flash."

"Ok I guess," Jessie replied as he lifted his nightee exposing his lacy panties.

"Sweetie, can I ask a personal question?"

"Sure."

"Where is your penis? It just looks really flat there," Ashley asked as politely as she could. She wondered if it had somehow disappeared.

"I put it between my legs," Jessie stated matter of factly.

"Why do you do that?"

"Ummm, I don't know. I just do it for some reason I guess. I never thought about it before," Jessie replied. He didn't have a good answer for her...he just knew he needed to tuck it in to be comfortable with himself.

"Can I see your penis?" Ashley asked, hoping to see what had happened to it. The drugs Jessie was on changed his body so much that she didn't know what to expect from his penis.

"No way Ashley! If my mom finds out about this she is going to kill me. That's why boys shouldn't have slumber parties with girls!"

"Don't flatter yourself sweetie. I just want to see how you tucked it is all," Ashley quickly replied trying to put Jessie at ease.

Jessie somehow felt comfortable enough with Ashley to calm down and show her how he tucked himself. He pulled his panties down and let his penis out.

Ashley was taken aback by the size of it. It was the smallest thing she had ever seen. It protruded from his body maybe 1" she guessed. Those drugs were so powerful she imagined. Another thing she noticed was the lack of his balls. He no longer had anything hanging. She could see the embarrassment in his eyes and decided not to pursue the conversation any further.

"Go ahead and pull your panties back up Jess...I didn't mean to embarrass you."

"It's cool. You are the first girl to see my package...pretty impressive huh?" Jessie gloated.

"Yeah sweetie...impressive. Gotta big ego there don't ya?"

"Haha, I was just joking," Jessie replied as he lightly pushed Ashley's shoulder.

"You don't know who you're messing with girl," Ashley said as she nudged Jessie back on the shoulder.

"I may have to put you in your place woman...my momma told me never to hit a girl but I may have to keep you in check, haha!" Jessie joked as he pushed Ashley playfully again.

Ashley moved to avoid him and tried to slap his arm in the process. She missed his arm however and struck his breast.

"Ouch!" Jessie yelped. "That hurt!"

"I'm so sorry Jess!" Ashley replied, realizing how much it hurts when someone hits your breast. "I didn't mean to hit you there. I wanted to hit your arm."

"Yeah, well there is a distinct difference between my arm and my boob ya know?" Jessie retorted as his eyes filled with tears.

"Your what?" Ashley asked again not sure if she heard him correctly. Did he just say his boob?

"My boob...you hit my boob...and it hurt," Jessie complained once again. He didn't know why he had to repeat himself...it was pretty apparent that she had hit his breast.

"I really didn't mean to hit your breast...I know how much that hurts," Ashley apologized. She was amazed at how he suddenly was aware that he had breasts but didn't realize that boys don't have breasts.

"I know it was an accident. I was trying to take it easy on you cause you're a girl and I'm a guy but dang you don't fight fair!" Jessie said sarcastically.

"Well maybe I'm not used to the boy's I fight having boobs that get in the way," Ashley responded pushing the envelope a little.

"I don't know what that means but I forgive ya," Jessie replied even though her statement did not register in his head. Sometimes Ashley didn't make a lot of sense he thought.

"Ok, maybe we shouldn't fight anymore...here, let me do your nails now my big brave girly girl."
 


To Be Continued...

 

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Comments

Interesting, Very Interesting Indeed

Just what is next will be well worth waiting for,
May Your Light Forever Shine

    Stanman
May Your Light Forever Shine

Softening of Jessie

Great story and I was really into it until I came to the end of Chapter 23 and noticed that there is a big gap in the story. Does anyone know how to find the missing chapters ? I would really like to read them before proceeding to the next posted chapter. I realize that it's a lot of work keeping this (and other similar) sites up and running and I just want to say THANKS for those who use their free time so the rest of us can use ours lost in the fictional worlds they create for us !!!!

Drucilla, I'm the One Posting

up The Softening of Jessie for AshleyTS. Im responsible for doing the chapters prior to 37. They are going up usually 2 times a day, sometimes 1. They'll all be up there soon.

 
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