Ashley reached out and grabbed Jessie's nipples and twisted them hard. She was a bit taken aback as she found his nipples to be larger and easier to grab than she had expected them to be.

"OOOWWWWWW!!!!" Jessie screamed at the top of his lungs. He buckled over in pain as he eyes immediately filled with tears. "That freaking hurt!!!" He yelled as he rubbed his aching chest and wiped away the tears as they flowed from his eyes.

"Dang, are you faking it Jessie? I didn't twist them that hard." Ashley wasn't sure what to think of his extreme reaction.

"No I'm not faking it! I told you that my chest has been super sensitive. That really hurt!"

The Softening of Jessie
Part 7
By AshleyTS

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Jessie sat on his bed looking at the new underwear his mom had bought him. Something wasn't quite right about it but he didn't know what. His mom was so supportive and understanding of his sensitive chest and his sudden weight gain in his lower section. He should be grateful that he has such a wonderful family.

"What the heck. Let's try these bad boys on and see if they fit."

Jessie stripped down and looked at the selection of underwear in front of him. The logical choice, he thought, would have to be the pink set since his nails were a similar color.

"You are a fashion stud," he thought to himself.

He slipped his right foot into the pink panties and then his left. He slid them up his legs and over his hips until they were snugly encasing his ever rounding butt. He thought to himself how great these new underwear fit him. "Mom nailed this one." He thought as his ran his fingers over the pretty lace that fashioned the band of the panties. Something didn't feel quite right about this he thought but his excitement over proper fitting garments superseded those thoughts.

"Well, they are a little lower cut than my old underwear but they are sooo comfortable!" Jessie proclaimed as he relished the delicate, soft cotton fabric.

Next he gently put on the pink camisole being careful not to brush his sensitive nipples. The top fit very snugly and came to an end just above his belly button. Once again, he was amazed at how soft and very comfortable the material was.

"How come I never had mom buy me underwear like this before? This top reminds me a bit of my wife-beater t-shirts."

With that, Jessie put on some sweat pants and shoes and headed to the bathroom to pee. As he was sitting on the toilet he thought to himself that flys on underwear are silly anyways. Who needs a fly when you pull your underwear down to pee? It just seemed like an unnecessary thing. Who thought of putting flys on underwear anyways? Haha!

Jessie headed downstairs.

"Hey mom...grandma. Mom, the underwear fits crazy good and the colors are cool. I'm gonna go see if Jason is doing anything. I'll be back around 5."

Both Amanda and Susan just stared at Jessie in a little disbelief. There he was in his raggy shoes, worn out sweat pants and a very feminine pink camisole with tiny lace stitching and spaghetti straps. Was his chest larger or did it just seem that way since the camisole was so tight? In any case, the snug fabric definitely showcased his budding femininity.

"Ummm, Jess dear" Susan said, carefully choosing her words, "Although that top looks very nice on you, it is an undergarment which means that you should wear a shirt over it."

"Oh, I was just figuring that it was like one of my v-necks or white undershirts that I could wear outside if I wanted," Jessie answered a bit confused.

"Not with these new tops Jessie. These are meant only to wear under your clothes. Why don't you go put a shirt over it and then you can go play. You do look great in pink though Sweety."

"Thanks grandma. It matches my toenails."

Jessie put on one of his t-shirts and headed to Jason's house a couple blocks away.

Amanda and Susan were in awe of what had just happened. "Susan, he was going to go out of the house like that. We need to be careful because he is not aware of what is happening to his body. I'm not sure if I want him going to school like that. I'm afraid for his safety mom." The two thought about the ramifications of what was going on and how to handle the quick changes that were occurring in Jessie's life.

Jessie, in the meantime, was ready to chill with his buddy. He knocked on Jason's door only to have his pretty 15 year old sister answer the door.

"Ummm, is Jason home?"

"Nope, he went out with some of his friends. He'll be back later. Hey Jessie, what is different about you? Did you change your hairstyle or put on weight or something?" Ashley asked, noting that he looked a little different than she remembered although she never paid much attention to that rotten boy. He had always been so cruel to her and her friends. She found it rather funny that Jason ditched him to hang out with some other friends...the little punk deserved it.

"I haven't been feeling great lately is all." Jessie replied. He was a little offended that Jason didn't call and invite him anywhere. "I think I have an allergy or something cause my chest has gotten real sensitive lately."

"Really. Well that sucks for you. Hey, you remember when I was younger and I told you how my chest was sore and sensitive? You remember what you did?" Ashley asked in a rather mean tone.

"Uh, no. What did I do? Maybe it would help for me too," Jessie answered.

With that, Ashley reached out and grabbed Jessie's nipples and twisted them hard. She was a bit taken aback as she found his nipples to be larger and easier to grab than she had expected them to be.

"OOOWWWWWW!!!!" Jessie screamed at the top of his lungs. He buckled over in pain as he eyes immediately filled with tears. "That freaking hurt!!!" He yelled as he rubbed his aching chest and wiped away the tears as they flowed from his eyes.

"Dang, are you faking it Jessie? I didn't twist them that hard." Ashley wasn't sure what to think of his extreme reaction.

"No I'm not faking it! I told you that my chest has been super sensitive. That really hurt!"

Ashley could see the genuine pain in Jessie's tearful eyes and for a moment she felt awful about what she had done. He deserved it though didn't he? Sure he did. He was a thorn in her side for as long as she had known him. Her thoughts, however, were drawn once again to just how much flesh she had grabbed.

"Jessie, I'm sorry. I didn't realize how much you were actually hurting. Ummm, can I see your chest? Maybe I can give you something to help with the pain," Ashley asked hoping to see what the heck was up with his chest.

Jessie never did like Ashley. She was part of the "popular" crowd and he was more of the outcast troublemaker. She did seem genuinely concerned though and he thought that another opinion of what was going on with his chest couldn't hurt.

"Ok Ashley, but you have to promise not to pinch or hit or do anything else to me Ok?"

"Ok Jessie...I promise."

Jessie lifted his shirt and took it off exposing his pink camisole top as Ashley's jaw dropped.

"What are you wearing Jessie??? Where did you get that???" she asked in a surprised tone.

"My mom gave me this top to wear until my swelling goes down. It helps with my sensitivity. Why?" Jessie pondered her odd question.

Ashley quickly came to the realization that something odd was definitely up. Look at him. He's standing there wearing a top that she probably had in her underwear drawer and he was completely oblivious. Should she say something? Did his mom finally lose it? Who cares? Jessie obviously was getting what was coming to him and he did look awfully cute standing there in that pink top.

There was something else though...something very odd indeed about the top...or more specifically the two bumps pushing through.

"Jessie, lift you camisole and let me see your chest," Ashley asked.

Camisole? Why did she call his top a camisole? Girls always had such weird terms for things. Jessie lifted his top to display exactly why he needed his soft undershirt. Ashley's eyes grew big as she witnessed two small mounds on either side of his chest. They were breasts...or budding breasts to be exact, but they were definitely not supposed to be on a boy's chest.

"Who knows about those bumps Jessie?"

"Just my mom and grandma...Jason saw them and now you."

Jessie's mom and grandma must be up to this Ashley thought. Dang! They must really be fed up hehe! Well she certainly wasn't going to interfere with their plans. Maybe this is just what Jessie needs to stop being such a jerk.

"Well Jessie, I had the same problem with my chest a couple years ago so I sympathize with what you are going through and I'm sorry for twisting your nipples."

"It's Ok. I guess I was kind of mean to you in the past. Did you have an allergic reaction or infection too? How long was it until the pain and swelling went away?" Jessie asked. Perhaps she could shed some light on what was wrong with him.

"Well...ummm, one day there was just some sensitivity on my chest and two small bumps developed shortly after. My mom had me wear tops like you are wearing to help. The pain and irritation stopped a few weeks after so just take it easy and it should mellow," Ashley carefully explained. That kept it vague enough she thought.

"Cool, so mom was right about the top then. How about the swelling? Did your chest go back to normal?"

"Well, you could say that my chest ended up like any "normal" girl's so yes, it did become normal."

"Good news then!" Jessie replied. It was awesome to meet someone who had been through a similar situation as he was going through. Her chest turned out normal so he had high hopes that his would too.

Why was Ashley looking at him so weird he thought? She had this odd smirk on her face which made him a little uncomfortable. He pulled his camisole down and put his shirt back on.

"Thanks for all the great information Ashley. You are cooler than I thought. Do you mind if I call you if I have any more questions?"

"Not at all Jessie. I would really like to see what happens with your chest so stop by any time. Are you rubbing it with cream every day? That's important cause your skin is stretching," Ashley advised the clueless boy.

"Yep, everyday. Well, I'm gonna head back home I guess since Jason isn't here, but I‘ll see you later."

"Bye bye cutie."

As Jessie headed back home he reflected on what Ashley had said. It was a relief to speak to someone who had the same symptoms as he had and to see that it was only temporary. He would just have to stick it out and be careful and he would be back to his old self in no time.
 

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To Be Continued...