"Why don't you try it on yourself Jessie? If you practice on yourself you will be much better next time I need my nails done," Amanda said amusingly.

"No way mom! Only girls and sissies paint their nails. It would be the end of me if anyone saw me with pink nails," Jessie said firmly.

Amanda thought it was quite funny that Jessie had such low opinions of girls and sissies seeing that he was sitting there is a rather feminine lacy camisole with two small bumps on his chest.

The Softening of Jessie
Part 5
By AshleyTS

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Sunday morning Jessie got up at went downstairs to watch whatever sports were on. He had been a sports fanatic all his life. If it involved anything physical and testosterone laced, he was all over it. He decided to skip his shower today and sat himself down comfortably on the couch.

Jessie flipped to the football game and quickly caught up on what was going on. For some reason though, he couldn't get into the game. He decided to flip the channels some more...soccer, tough man, nothing seemed to attract his interest today. He flipped the channels some more and landed on America Next Top Model.

"What the hell." He thought. "Nothing better on."

He had flipped by this show numerous times before and could not stomach a minute of it, but something drew him to it suddenly. He found himself admiring the women on the show. They were so pretty and graceful...the way they talked, the way they moved...elegance to its extreme. Look at Tyra. She is such a role model. She has it all....beauty, brains and talent.

"Those girls must be under so much stress to make it to the next round," Amanda stated as she walked into the room.

"Oh...hey mom." Jessie quickly changed the channel. "I wasn't really watching that...it was just a commercial break on the other channel is all."

"It's OK Sweety, you can watch the model show if you want...or how about you let me watch it since I enjoy it and we can turn to your sports in a minute?"

"I guess I can bear letting you watch Top Model...but only until my show comes back on ok?" Jessie layed down the rules.

With that Amanda changed the channel back to Top Model. She saw the look in Jessie's eyes...he loved the show.

"Those women are really pretty aren't they?" Amanda asked her son.

"Yeah mom. I really like the way that they move and their makeup looks so interesting."

Amanda had brought out her nail kit with some polish and she began filing her fingernails. She saw that Jessie took short glances at her and what she was doing.

"Nail maintenance is very important Jessie. It says a lot about who you are as a person. Neatly manicured nails are a sign of a well put together person. Let me see your nails." Amanda asked her son.

"Nah, it's ok mom. I'm not trying to impress anyone," Jessie countered.

"Oh come on chicken, let me see your nails," Amanda dared him.

"I'm not chicken. Just don't do anything weird to them."

Amanda gently grasped Jessie's hand and looked at his nails. They were slightly long for a boy and were actually pretty clean. She showed him how to maintain his cuticles and file off and round off his nails. He was very interested and she could tell. He was just becoming so darn cute!

"There ya go. See how much nicer they look?" Amanda asked. "If I saw you my first impression would be that you really had your act together."

"You think so? They do look nice I guess."

Amanda continued unto her toenails and began painting them a rosy colored hue.

"Wanna try painting my toenails Jessie?" Amanda asked after seeing interest in his eyes.

"Umm, I'm a horrible painter haha. Only if you want your entire toes to be pink."

"Go ahead...give it a try. If you mess it up we can always remove it with polish remover."

With that, Amanda lovingly showed Jessie how to properly use the brush and apply the polish. He was awkward at first but after a couple minutes he was getting the hang of it. The focus on his face was amusing she thought. He was so intent on doing it right. She wondered if he realized how much more feminine he had become...did it register at all to him?

After he had finished her toenails, she invited him to do her fingernails. He quickly accepted and did a fine job on her hands.

"Why don't you try it on yourself Jessie? If you practice on yourself you will be much better next time I need my nails done," Amanda said amusingly.

"No way mom! Only girls and sissies paint their nails. It would be the end of me if anyone saw me with pink nails," Jessie said firmly.

Amanda thought it was quite funny that Jessie had such low opinions of girls and sissies seeing that he was sitting there is a rather feminine lacy camisole with two small bumps on his chest.

"Oh come on Jessie. Who on earth is going to see you? Just do your toenails. I mean, when is the last time you went outside without shoes on...ummm, never. The only way you get better at something is by doing it over and over. I won't tell anyone and I know grandma won't either. Besides that, if it freaks you out too much you can just remove it. Not a problem."

His mom made a lot of sense lately. He didn't want his nails painted but he really did want to master the art of painting nails. It would be for the sake of mastering his new interest...yeah...that's the ticket!

"Okay mom, give me the polish. You'll see how good I am...all it takes is a little practice. I will master this in no time."

Jessie practiced painting his nails the pretty rose hue several times. Each time he would finish, he would use the cotton balls soaked in polish remover to clean the nails, and then paint them again. Amanda found it utterly enjoyable to see how intent he was on the task at hand. He was getting very good at it she admitted to herself with a smirk.

"Take that mom!" Jessie announced proudly as he dangled his toes in front of her.

They were beautiful. He had painted them to perfection. Pretty in pink was never quite as apparent as it was at this moment. With his shaven legs and his very feminine looking toenails, Jessie looked adorable.

"Wow, look at you Jessie! Those look magnificent! OK, I have to admit I'm a bit surprised. I wasn't sure if you could do it, but you did."

Amanda leaned over and gave Jessie a big hug and a kiss on the cheek. Jessie couldn't remember a time when he was so proud of impressing his mom.

He told his mom that he would let his nails dry and then remove the polish, but something gave her the feeling that the polish would stay on. She could see the gleam and sense of accomplishment in his eyes.

"How is your chest feeling today honey?" Amanda asked.

"I rubbed some cream on it today, but it is still really sensitive. My top feels good on it though but I think that they are still swelling up though.

Amanda asked Jessie to lift his top and they indeed were continuing to swell. He was definitely budding. Each nipple was slightly raised and the pink area around each nipple had grown to the size of a nickel. The nipples themselves jutted out somewhat, showing some sensitivity to the cold air.

"Yes they are still swollen sweety. Sometimes infections and rashes take a while to go away. The best thing you can do is just be gentle and be sure to wear soft fabrics over your chest. I will get you some more that you can wear under your regular shirts okay?" Amanda assured him.

"Okay mom. I promise to take it easy on my chest. I just want the sensitivity to go away is all. If you buy me some new undershirts though could you buy me some bigger underwear? My briefs are getting really tight and it doesn't help that I'm sore all over so that the tight tension kills me when it digs into my hips and butt."

"Getting a little out of shape sweety?" Mom teased.

"Whatever!" Jessie playfully fought back. "I haven't been feeling very well lately so I have been skipping my exercises."

"I have that packet of larger underwear I bought on accident a while back still in your drawer. Did you try those on?"

"Yeah mom I did. They fit well on my hips but around my waist they didn't. The elastic was too big and loose. I think they were a defect. I want my underwear to be like how it used to...snug around my hips and snug around my waist but not overly tight," Jessie said matter-of-factly.

"Ok, I will look into that too. Underwear tops and bottoms...got it! Anything else your majesty?" Amanda added jokingly.

"That will be all, haha!"

Jessie's pajama bottoms were loose and she had a hard time telling if his hips and waist had grown to more feminine proportions. They must have though. Why else would his underwear fit too tight in the ass and hips and too loose on the waist? She lovingly admired her son as he sat in front of the TV and finished watching his fashion show. His nails really did look lovely as did his whole outlook on life recently. Ok Amanda, time to go shopping!
 

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To Be Continued...