"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

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The "girls" finished up their nails and got ready for bed. Ashley noticed Jessie putting on his headphones. Was that where he received his subliminal messages from?

"Hey Jess, can I listen to what you have in the cd player?"

"Ok, but I gotta have it back before I go to sleep."

"You listen to this every night?"

"Yeah, I can't fall asleep unless I am."

Ashley put on the headphones and pressed play. The music was soft and relaxing, but had jumbled voices throughout the sounds. She listened closely to try to decipher some of the words. The music had an odd and addictive quality to it and she found that she had a hard time taking the phones off. She quickly pulled them off however as she quickly became freaked out.

"You know what those voices say in the songs Jessie?"

"I've been able to make out some of them, but they are just regular words mostly. Nothing really weird or anything."

"What words Jess?" Ashley questioned.

"Let's see...I've been able to recognize "feminine", "girl", "right","soft", "pantyhose", "normal"...stuff like that. Pretty average things."

"I see...so being feminine is normal for you? Wearing pantyhose feels right?" Ashley asked.

"Yeah, of course...why wouldn't it be?"

"No reason. You are a very interesting person Jess."

With that the two went to bed. Ashley asked if she could sleep in the same bed as Jessie. He protested at first, to sure what his mom would think, but decided to live dangerously. How often do you have a pretty girl who is willing to share a bed with you?

It's funny how this moment seemed like it should have been so much different than it actually was. He didn't think of Ashley in a sexual way at all. She was a very cool girl and he was happy to have her as his friend, but there were no sparks. He wondered if she didn't find him sexually attractive. He was a good looking boy he thought and she was definitely a pretty girl.

He thought of how he could make himself look more desirable to her. How do guys attract girls, he thought? He tried to position himself on the bed sideways to showcase his bulging biceps. Dang! His nightee was wrapped around his legs which dug his spaghetti strap into his shoulder. He inconspicuously adjusted the skirt from his nightee and turned sideways. Should he show some cleavage maybe or hike up his skirt and show some leg? His thoughts were incredibly jumbled and he finally rolled over and gave up.

"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.

"Explain what dear? The only explanation I need is why you didn't wash the makeup off your face before going to bed. Look at the mess you made of your pillow. Ashley, you really should teach Jessie good habits."

"Uh sorry," Ashley apologized.

Jessie looked at his pillow and sure enough you could see the lipstick, rouge, eyeshadow...everything on his pillowcase.

"Well why don't you two get ready. It's lunch time so I'll take you out."

With that Ashley hopped in the shower followed by Jessie. Ashley was in her bra and panties when Jessie came out of the bathroom with his towel wrapped around himself in a very feminine way.

"Whoah! I'll close my eyes!" Jessie yelped.

"It's Ok Jess, you wear the same kind of underwear, so I don't mind."

Jessie thought about it and she was right. That was not right though, was it? She was a girl and he was a boy, but they wear the same underwear? He couldn't wrap his mind around it to make any sense.

"Well you gotta turn around until I get my underwear on though," Jessie replied.

Ashley turned around as Jessie slipped on his VS low cut pink panties and the matching bra. She noticed that his boobs were not sitting quite right in the cups and looked a bit squished.

"Jess dear, a bra is meant to flatter your breasts, but you are not utilizing it properly. Can I show you?"

"Ok."

Ashley reached into Jessie's bra cup and lifted his left breast up into the cup, so that it was sitting nicely high. She followed with the other.

"Wow Jess, you are really blossoming aren't you? See how much nicer they look now?" Ashely asked as she was amazed at how much his breasts had developed. His bra was a B cup and his boobs filled it fully.

"Yeah, they look so much bigger this way," Jessie replied looking down at his boobs. He never realized he was so well endowed. In fact he never realized he was "supposed" to be so well endowed in the breast area.

Ashley slipped on a top and a pair of shorts, but couldn't take her eyes off Jessie as he slipped his pantyhose on. He rolled them up as well as any girl she ever saw. In fact he was better at it than she was. He even did the little dance that women do as he pulled the nude pantyhose over his hips and around his waist.

"You really love you pantyhose don't ya? I have to admit you do have some very nice legs."

"Thanks," Jessie replied as he gushed over the compliment.

"Hey Jess, with such nice legs you should wear stuff that shows them off more."

"Like what?"

"Well, why don't you ever wear skirts or dresses?" Ashley asked figuring she could take that leap.

"Skirts? Dresses? Ummm, cause I'm not a girl! That's a pretty simple answer."

"But you don't mind me calling you a 'girl'?" Ashley relied.

"No, why?" Jessie answered a little confused by the question. Why would he care if she called him a girl? All he knew was that he wasn't a girl so he wasn't going to entertain the thought of wearing a dress.

Ashley was dumbfounded. He didn't mind being called a "girl" but he still thought of himself as a boy. She wondered how many more times he would have to listen to the tapes before he gave in. She decided to take a different approach.

"Jessie, you love wearing pantyhose right?"

"Yeah."

"Well think about it. How many times have you seen people wear pantyhose with shorts or pants? Not very many right?"

"Uh, yeah." He actually couldn't think of a time when he saw pantyhose being worn under a pair of pants or shorts.

"Well then what do you see pantyhose worn with then smarty?"

He thought about it but really didn't have to. He knew he was caught.

"Ummm, skirts and dresses."

"So why don't you ever wear skirts and dresses then silly?"

"I really don't know I guess. I never thought about it."

"Well you are in luck cause I have both if you want to try. What do you say? I'll even put on one too if that would make you feel more comfortable."

"I guess it wouldn't hurt to try it," Jessie replied. Her logic made perfect sense in a ridiculous sort of way.

"Cool! I'll grab my stuff!"
 

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To Be Continued...