The Softening of Jessie - Part 28

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"Really? Jason was actually nice to me today and Ashley said that it was because I had breasts. I don't know what the big deal is. Some boy's have breasts some boys don't," Jessie said matter-of-factly.

"No dear, only girl's have breasts. Boys have pecs which are hard and girls have breasts which are soft."

"But I have breasts and I'm a boy..." Jessie said as he became incredibly confused. He couldn't put two and two together and found his mind very clouded when he tried to figure it out.

The Softening of Jessie

Part 28

By AshleyTS


 
After a long day of shopping Jessie returned home just in time for dinner.

"Perfect timing Jess. Dinner is served," his mom said.

She noticed that he had a couple bags with him.

"What did you buy dear?"

"Oh, Ashley likes to buy me things," he replied as he pulled three garments out of the bag. One was a jeans mini skirt, the other was a white colored top made of a stretchy fabric with short sleeves that puffed slightly. The last piece of clothing was a black cocktail looking dress which had thin spaghetti straps and looked like it would fall just above the knees.

"Those are pretty Jess. So I take it you like wearing skirts and dresses?"

"Yeah mom, I can't believe I didn't have any in my closet. I guess I just never paid any attention to what's in style out there."

"Did I tell you how pretty you look in that dress dear? You look like an absolute angel," his mom gushed.

"Thanks! It feels so light and airy...I love it!" he replied as he did a little twirl.

"Oh Honey, you have a run in your pantyhose," his mom said and she admired the feminine creature.

"Yeah, I know. Some woman gave me some nail polish to stop the run. Did you know that a little polish prevents the run from getting any larger?"

"Yes, I know that. It was awfully nice of her to give you that tip."

"I know...she even complimented me on my cool dress when I was in the restroom."

"The restroom? You went in the ladies room right?" his mom asked. She hoped that Ashley would guide her son to a proper bathroom.

"Yeah mom. Ashley told me that I had to use the Women's room since I was wearing a dress. I thought it was real weird to be in the same bathroom that women are in since I'm a guy, but it made sense since we were all wearing dresses."

With that they had dinner.
 
 
"How about modeling you new clothes for me?"

"Cool. I'll be right back!" Jessie said very excited.

He ran upstairs and took his new clothes out of the bag.

He tried to remove his dress but found that the zipper in back was beyond his reach.

"Hey mom! Can you help me unzip my dress?" he asked.

Amanda ran upstairs and helped her son unzip his dress.

"Ok, you can leave now mom. I'll come outside when I have the outfits on."

"Oh don't be such a shy boy, I think I am OK with seeing you in your underwear aren't I?" his mom asked.

"Mom, it's embarrassing! You're my mom and I'm a boy... you're a girl... get it?"

"No I don't get it sweety. I think that since you are wearing dresses and skirts that I could provide valuable pointers. I think you could use your mother's help. So if you want me to leave I will, but like I said I've seen it all before dear."

"Ok, this is all kind of new to me I guess. Just promise you won't laugh at how swollen my chest has gotten or how out of shape my butt has become."

"I promise dear."

Jessie let his dress fall to the floor. His mom was awestruck at the teenage girl that stood before her. There really wasn't any sign of boy left. The "out of shape" butt Jessie was referring to was a feminine curved girl's behind which was fully encased in pantyhose.

"I'm gonna try on the black dress first."

Jessie stepped into the dress and pulled the spaghetti straps over his shoulders.

"Yeah Jess, that bra doesn't work with that dress. You can see the strap since the back of the dress is so low. We are going to have to find you a bra to wear with this one. Why don't you take off the bra then try the dress on again so we can see how should look."

With that Jessie pulled down the straps, unhooked his bra and laid it on the bed.

"What's wrong mom?" Jessie asked as he saw his mom's face. She had tears running down her cheeks as she looked at him.

"Nothing dear, everything is perfect. You look so amazingly beautiful," Amanda replied as she fought tears of joy. Her son had blossomed into such a lovely young woman. His breasts were so beautiful and she found herself so very proud of him.

"Ummm, thanks. See you're embarrassing me now," he said as he covered his chest with his hands.

"Oh Sweety, don't be embarrassed. I have breasts too. They are something you should be proud of and there's nothing wrong with showing them to other women. You want to keep from showing too much of them to boy's though."

"Really? Jason was actually nice to me today and Ashley said that it was because I had breasts. I don't know what the big deal is. Some boy's have breasts some boys don't," Jessie said matter-of-factly.

"No dear, only girl's have breasts. Boys have pecs which are hard and girls have breasts which are soft."

"But I have breasts and I'm a boy..." Jessie said as he became incredibly confused. He couldn't put two and two together and found his mind very clouded when he tried to figure it out.

"Why don't you try on you shirt and skirt Jess?" Amanda said as she quickly changed the subject.

"Ummmm, yeah, Ok," Jessie said as he brushed off his confusion and put the white top on. It was a very clingy material that snugly formed to his feminine curves.

He pulled up the skirt and zipped up the zipper in back.

"Wow, very sassy dear," his mom said.

"You are going to definitely want to wear a bra with that top though," Amanda added as she could see just about all of his breasts tenting the front of the shirt.

"How long do you think I'll have to keep wearing a bra for mom? I know I started wearing one because my chest was swollen and it doesn't look like the swelling is going to go down any time soon."

"Sweetie, I think you are going to be wearing bras for the rest of your life. Your breasts have developed they are going to need support. Does that bother you? I mean do you mind having breasts?"

"Well they are a little weird. I can't really run the same as I used to because my chest really bounces. They also seem to get in the way a lot and I have to change the way I'm used to doing things."

"Well those are all things you will get used to. Then everything will become second nature to you."

"Yeah, I guess your right. I really don't mind wearing bras that much. It would really suck if bras didn't exist. I'd be jiggling all over the place," Jessie joked.

The two shared some laughs and bonded in the way mothers and daughters do.

The phone rang the next morning.

"Hey Jess, wanna go to raging waters today? I got some free tickets!" Ashley asked.

"Awesome! I'm sooo in!"
 


To Be Continued...

 

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