AshleyTS

The Softening of Jessie - Part 31

"It's up to you Jess. Do you want to wear a skirt?"

"I think I do...what do you think Jason will be wearing?" Jessie asked finding himself confused about skirts, dresses and pants. Would Jason be wearing a skirt too? Jason is a boy so he can't wear a skirt. Wait...I'm a boy too but I am going to wear a skirt? Jessie's mind clouded.

The Softening of Jessie

Part 31

By AshleyTS

The Softening of Jessie - Part 30

"He wants to hang with me again? I'm shocked. I mean I thought he didn't like me anymore."

"Uh yeah. He really likes you. You don't want to hang with him though do you? I mean after how poorly he treated you?" Ashley replied playing along knowing that Jason really liked the new Jessie...the girl.

Jessie thought about it for a minute. Sure Jason was mean to him. He was downright evil to him when he was going through tough times awhile back. People change though right? Jason must have changed! Was his friend truly back?!?

...As she's watching me with those eyes, she could be loving me with that body...

The Softening of Jessie

Part 30

By AshleyTS

The Softening of Jessie - Part 29

One thing that made him uncomfortable however was all the strange looks he would get from boys. Girls didn't even seem to notice him but the boys kept staring him down. They did seem friendly though so he didn't feel threatened.

"Looking good" "Like that suit on you" "Hey girls, looking fine today" where some of the remarks from the boys who passed.

Jessie began to feel very good about himself. He wasn't used to all the attention and he found it nice. His step had a little more bounce in it...his ass gained a little more wiggle when he walked. He found that he enjoyed the attention.

The Softening of Jessie

Part 29

By AshleyTS

The Softening of Jessie - Part 28

"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

The Softening of Jessie - Part 27

"We had lunch and are just walking around and shopping a bit," Ashley replied when it struck her. Her brother didn't recognize Jessie! It made perfect sense! Jessie had changed so much in the last few weeks that he only looked like a pretty shadow of his former self. Jason was nervous because he was attracted to Jessie!

~*~

"Time to go...see you later little bro...Tata!" Ashley replied as she whisked Jessie away. The fact that her brother was openly flirting with his former best friend...who was blossoming into a beautiful girl was priceless!

...We're talkin' About Jason's Girl!...

The Softening of Jessie

Part 27

By AshleyTS

The Softening of Jessie - Part 26

She then brushed Jessie's hair and pulled it back into a ponytail tying it with a light blue ribbon.

"Amazing! How do you feel Jessica?" Ashley asked her unmistakably feminine friend. She decided to throw out the name Jessica to see if it would stick.

"I feel great...this dress is so airy and comfortable! Why did you call me Jessica though?"

...Jessie's a Girl, and I Wanna make her Mine!...

The Softening of Jessie

Part 26

By AshleyTS

The Softening of Jessie - Part 25

"Ok, I was wrong I guess. Thanks for letting me borrow one of your dresses Ashley."

Jessie gave her a big hug. He was so lucky to have such a great friend.

"Damn you are sexy!" Ashley replied as she reached under his dress and pinched his ass.

"Hey! Stop that!" Jessie yelled embarrassed and a little surprised at how easy it was for her to reach up under his skirt.

The Softening of Jessie

Part 25

By AshleyTS

The Softening of Jessie - Part 24

"Hey you two, time to wake up. You're going to sleep your life away," Amanda said as she walked into Jessie's room. She observed the two "girls" looking so sweet as the slept on the same bed. Her son had really blossomed into something very special.

"Mom! I can explain..." Jessie quickly replied knowing that he was in trouble for sleeping in the same bed as a girl.

The Softening of Jessie

Part 24

By AshleyTS

The Softening of Jessie - Part 23

"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

The Softening of Jessie - Part 22

"So what do you want to do?" Jessie asked. He felt a little uncomfortable being in the same room with such a pretty girl. He always thought of himself as the man but his nerves were getting the better of him.

"Well I think I should give you a makeover," Ashley replied as she pulled out her makeup box.

"A makeover? What do you mean?"

"Well you have to trust me ok? I want to have some fun with you."

The Softening of Jessie

Part 22

By AshleyTS

The Softening of Jessie - Part 21

"What's wrong?!?? What's wrong???!? What the hell is wrong with me??!!? Why am I dressed like this?!?? What...What the hell!!" Jessie frantically screamed as he noticed he was wearing a bra...He did manage to pull down the straps and get it off, only to be floored by what he saw...the visual site of two fleshy mounds protruding from his chest!

Jessie was a friend,
Yeah I know he was a good friend of mine.
But lately something's changed that ain't hard to define:
Jessie's turned into a girl and I want to make her mine.

 
As she's watching me with those eyes,
she could be loving me with that body, I just know it.
Wish I was holding her in my arms late, late at night.

 
You know, I wish that I had Jessie as a girl,
I wish that she was Jason's girl!

Comment made to The Softening of Jessie Part 39 by Jennifer Brock. Thanks Jennifer! :) (With apologies to Rick Springfield!)

The Softening of Jessie

Part 21

By AshleyTS

The Softening of Jessie - Part 20

As he looked at himself he remembered at how difficult it was to run earlier. Holy Moly! His ass was huge! He turned and twisted to get a better look, but whichever angle he had ended with, the same result. He had a big butt! Since when did he look like a pear? Hmmm, no wait...it wasn't a pear, he thought. His body reminded him of something else. That's it! An hourglass. He looked more like an hourglass in shape. How odd...he never thought of himself in that way!

He continued to stare, knowing in his gut that something was wrong. He knew that he looked different somehow, but he couldn't make sense of it. Was it his swollen chest? That might be it, but that was only a temporary problem, right? Sure his proportions had changed, but he really didn't have an issue with it, did he? This was getting frustrating. It was like knowing the answer to something and having it on the tip of your tongue, but not being able to remember it.

The Softening of Jessie

Part 20

By AshleyTS

The Softening of Jessie - Part 19

"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

The Softening of Jessie - Part 18

"Wow Jessie, you were such a brave girl! Your earrings look incredible too!"

"Thanks Ashley and I'm sorry for being such a cry baby."

"It's quite alright. First piercings are always rough. You were a brave girl!"

As Ashley paid for the earrings Jessie wandered out of the store in deep thought. Something wasn't right, but he just couldn't place his finger on it. What could it be? He was picking his brain trying to figure out where this deep rooted uncomfortableness came from, when suddenly... WHACK!

The Softening of Jessie

Part 18

By AshleyTS

The Softening of Jessie - Part 17

Jessie looked at the bra he was given to try out. He liked the color for sure. I mean who doesn't like light pink? He also liked the intricate detail on it...the tiny lace stitching, the flowers sewn into the center, the delicate straps.

He took off his top, then unloosed his bra, leaving his breasts dangling.

"Whoah! You have been eating your Wheaties, haven't you?" Ashley joked as she sat there open-jawed. On Jessie's chest hung two well formed breasts swaying gently as he moved. He must have grown a full cup size since she had seen them last!

Jessie quickly put the bra back on, feeling embarrassed.

The Softening of Jessie

Part 17

By AshleyTS

The Softening of Jessie - Part 16

In Jessie's clouded head, he assumed that all these men who were looking him up and down were trying to size him up to kick his ass, since he was with such a pretty girl - a pretty girl they wanted for themselves.

"What are you talking about? I just want to chat with you a bit, if that's cool," the boy explained.

"Really? Yeah, that's cool. I'm surprised you aren't like the rest of the guys in here. They keep looking me up and down like they want to kick my ass or something," Jessie expressed.

"Well, I'm sure they want to do something to you, but you can rest assured that it's not kicking your ass. I apologize for my gender...men can be dogs a lot of the time. I'm Scott by the way."

The Softening of Jessie

Part 16

By AshleyTS

The Softening of Jessie - Part 15

"Now why don't the two of you hug and make-up?" Ashley added.

"No way! I'm not hugging a dude!" Jason adamantly refused.

"Jason, I think you are being silly...I said WHY DON"T YOU TWO HUG?" Ashley firmly asked her brother knowing that she had him under her thumb. She loved seeing him squirm as well.

Jason begrudgingly agreed along with Jessie. The two gave each other a quick hug and that was that. Jessie felt a strange tingle when Jason embraced him. He didn't realize how strong Jason was and found himself blushing a bit. Jason on the other hand could have sworn that his former best friend felt like he had breasts. He had hugged enough girls to cop a feel and was shocked to find that Jessie's body reminded him of a girl's.

The Softening of Jessie

Part 15

By AshleyTS

The Softening of Jessie - Part 14

Suddenly a male model was called on the beach to do a take with one of the female models. Jessie's attention unknowingly switched focus from the girl on the beach to the male model. "Wow! That guy must have worked out tons to get that body!" he thought. As he watched the two partake in the photo session Jessie found himself observing an awful lot of the man. Look at those biceps and those abs…he felt himself getting a little flush. As Jessie continued to stare he found himself getting more and more aroused by the sight. His pretty painted hands found their way back to his chest and he began playing with his nipples. Whoa! Something about this felt very right indeed! He continued to caress his breasts as he stared down the male model. Look at how strong he is… amazing smile… what an ass!!!

The Softening of Jessie

Part 14

By AshleyTS

The Softening of Jessie - Part 13

"I think it's just cause your not used to wearing a nightgown and the pantyhose may be feeling different than the tights. How do you like your pantyhose anyway?" Amanda asked trying to change the subject.

"I was a little hesitant mom but I absolutely love them! It's almost like I'm not wearing anything. I like the feeling of the air flowing under my nightgown also. It feels cool especially when I do this."

Just then Jessie twirled around quickly several time as his nightgown ballooned up from the airflow.

"Wow, look at you. Maybe you should be taking up dancing," the ladies amused at his performance.

The Softening of Jessie

Part 13

By AshleyTS

The Softening of Jessie - Part 12

She was right. Ashley knew what she was talking about from her past experiences. If he was going to get better he would have to follow the same path as she.

"Yeah, I agree with you Ashley. I don't look dumb though do I?" Jessie asked being a little self conscious.

"You look fantastic babe. Why don't you put your shirt back on and see how you like it?"

Jessie put his t-shirt back on and looked down at his shirt. It was a little odd because he could see the two distinct bumps pushing out through his shirt very clearly now. They were perfectly formed and protruded slightly. Something in the back of his head told him that there was something not quite right about this but he couldn't place it. "It's probably nothing," he thought.

The Softening of Jessie

Part 12

By AshleyTS

The Softening of Jessie - Part 11

Ashley had to choose her words wisely she thought. Jessie looked so delicate and fragile sitting there with his knees together and hands gently overlapping each other.

"Well they don't make too many things to deal with your problem. There is something that works wonders but you may be opposed. The only thing I can think of that would help is a training bra. It would be perfect for you."

"Oh hell no! What are you insane?!? I'm not some sissy who walks around in girl's underwear for thrills." Jessie was upset. Perhaps a burst of energy from his male side needed to come out for a fight...even if it was a losing battle!

The Softening of Jessie

Part 11

By AshleyTS

The Softening of Jessie - Part 10

"What the hell are you wearing?!?" Jason asked in a standoffish, shocked way. His best buddy was fully clad in a girl's leotard and tights with his hair braided and tied with a frilly scrunchie.

"It's my new workout outfit...pretty cool huh? My mom could tell your mom where she bought it if you want one too," Jessie generously offered his friend.

"No way wierdo! You look like a freakin' girl dude! Are you going gay or what? I mean look at your hair! Did you flippin' pad your chest too, you homo?"

"No Jason...I...ummm," Jessie felt the tears begin to well up. He couldn't understand why his friend was being so mean.

The Softening of Jessie

Part 10

By AshleyTS

The Softening of Jessie - Part 9

"Those are tights Jessie. The kind you see wrestlers wear...I thought you might want to have the whole outfit, so I splurged and got you them," his mom offered.

"Cool! Why don't they have openings in the bottom of the legs though?"

"That's the way they are designed. You don't notice it with wrestlers cause they usually wear boots....and no, I'm not buying you the boots too."

"I guess I will take what I can get. I'll be right back!"

Jessie ran upstairs with his new workout gear. This was pretty cool...he wondered how jealous Jason would be when he saw these?

The Softening of Jessie

Part 9

By AshleyTS

The Softening of Jessie - Part 8

"I talked to Ashley, Jason's sister today and guess what? She had the same sensitivity and swelling like I am having. She said that it would only last for a little while then I would be normal again. If you want to keep me out of school though, I'm not gonna argue, haha!" Jason replied being more than happy to skip out on school.

Amanda and Susan were taken aback.

"Ashley saw you??? With your top off??? What did she say?" Amanda questioned...her heart pounding. What if Ashley turned them in? Is this illegal?

The Softening of Jessie

Part 8

By AshleyTS

The Softening of Jessie - Part 7

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

The Softening of Jessie - Part 6

"So we are in luck Jessie. I found some tops for you to wear under your shirts. They should fit tight so that no one can tell they are there and yet they are very soft which will help with your swollen chest. I also found you some underwear that should fit you better. Here's the fun part though...I was lucky enough to find them in matching colors. I know how you liked your old underwear to be in different, cool colors so I think you may like these," Amanda explained hoping Jessie would be fine with his new undergarments.

She knew that he did like his underwear in different cool colors meaning he liked black, grey, navy blue, and forest green. What would his take be on these softer colors? Would he accept wearing panties?

The Softening of Jessie

Part 6

By AshleyTS

The Softening of Jessie - Part 39

Swoosh! The ball went through the net.

“Awesome!” Jessie proclaimed as he jumped up in down in almost a cheerleader-like fashion.

The boys finished up with Jason winning by one. He was pumped and raised his hands in victory.

“Good job!” Jessie stated as he gave Jason a kiss on the cheek. Wow! Where did that come from? It was almost second nature for him. In any case, Jason seemed to like it as his face turned red from blushing.

The Softening of Jessie

Part 39

By AshleyTS

The Softening of Jessie - Part 5

"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

The Softening of Jessie - Part 4

In the restroom Jessie gingerly lifted his shirt. His chest was still very sensitive and his t-shirt felt like sandpaper on his nipples.

"Damn, I bruised ya pretty good on the shoulder, haha! Dude, what's wrong with your chest?" Jason was proud of the bruise he dealt Jessie, but he was fixated on Jessie's chest.

"Your nipples look freakin red and swollen. Do you have an infection or something?" Jason asked.

The Softening of Jessie

Part 4

By AshleyTS

The Softening of Jessie - Part 3

As Jessie stood to his feet though something welled up inside him and he found himself fighting back tears.

"Come on Jessie...come on you wuss!" Jason taunted him.

Jessie couldn't fight it...the tears welled up and he began crying.

"Oh hell no! You're crying dude? What a freakin sissy!" Jason exclaimed.

Panic engulfed Jessie as he ran away bawling uncontrollably.

The Softening of Jessie

Part 3

By AshleyTS

The Softening of Jessie - Part 2

Jessie was different. It may not have been a huge change but there was a definite difference. "I think I may like the new Jessie," Amanda exuberantly told her mom.

"Before you go to school, I need you to take this pill. It has all of your regular vitamins you take to build your strong body but in one pill."

"Why the heck is it pink? Ha, pink is for sissies and girls...but I guess if it saves me from all those other pills...ok, give it to me. Freakin pink pill...whoever made that needs some help." With that Jessie was off to school.

The Softening of Jessie

Part 2

By AshleyTS

The Softening of Jessie - Part 1

"I can't do this anymore," Amanda cried on the way home. Jessie, her 13 year old son, was uncontrollable. She had no idea where he went or what time he was coming home.

"How did I mess up so horribly?"

"You didn't mess up dear," Susan countered. "He is just like his father. It is in his genes. I am not going to see another life wasted though. When we get home I need to show you something. It is something I have been thinking a lot about and something I have been doing hours and hours of research on...and I think it is our solution."

The Softening of Jessie

Part 1

By AshleyTS

The Softening of Jessie - Part 38

“Huh? I’m a boy of course!”

Ashley snickered a little at the pretty girl who still did not have a clue to what was going on.

“So there is nothing wrong with two boys kissing then?”

Jessie thought about that for a minute. Two boys kissing would mean that they were gay. He wasn’t gay was he?

“Oh my! Ashley, am I gay? Is Jason?”

The Softening of Jessie

Part 38

By AshleyTS

The Softening of Jessie - Part 37

Suddenly Jessie was overcome with emotion. It hit him from out the blue with the intensity of a Mack truck. He was helplessly caught in its grasp. His eyes met Jason’s once again…then he glanced down to Jason’s lips. His lips looked so good…so inviting.. They looked undeniably yummy. Jessie couldn’t think straight…he felt a magnetic attraction pull him closer to Jason’s face. Wait, this was not right…was it? He so wanted to feel Jason’s lips on his…he just wanted them to touch for even a brief moment. That would be ok right? It didn’t matter, he had no say in the matter. He felt as if he was not in control of his actions any longer. He glanced at Jason’s eyes once again as their lips got closer. Jason’s eyes had almost a glazed look on them, Oh they were so handsome! Caught up in the moment, Jessie let his emotions fully take over as his lips met Jason’s.

...We're talkin' about Jason's Girl!...

The Softening of Jessie

Part 37

By AshleyTS

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