"Come here pretty girl and let me see your pretty pretty panties!"

They wrestled back and forth a little and Jessie was stunned at how strong Ashley was. He had a hard time believing it, but she overpowered him as she wrestled him to the ground.

The two rolled around for a minute and Jessie grew even more embarrassed as his skirt kept flipping up around his back.

"Aha, those panties look mighty sexy Jess!" Ashley teased as she pinned Jessie down on his back holding his arms to the ground.

The Softening of Jessie
Part 33
By AshleyTS

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"Okay sweetie sit down and let's do your makeup. I'm thinking of something smoldering with your eyes."

"Cool. Don't do anything too drastic though."

"Don't worry Jessica. You are in good hands."

"Before I start I'm going to put your hair in some rollers. It will give you some added volume and really enhance your appearance."

Ashley deftly rolled Jessie's hair into several curlers and marveled at how he didn't bat an eye at being put into curlers. He just took it with stride like it was just an everything thing. He looked ultra feminine sitting there with his legs crossed in such a cute outfit.

She began with a silky foundation which she blotted all over his face and smoothed with her sponge.

"Now close your eyes Jess."

Ashley artistically painted Jessie's eyelids a smoky smoldering charcoal which really accented his pretty eyes.

"Look up pretty girl."

She crimped Jessie's eyelashes then gently brushed the mascara wand over them several times to create long, thick lashes.

"Your eyebrows look fantastic but I'm just going to use this stencil to
make them flawlessly shaped."

Ashley penciled in Jessie's eyebrows to create a supermodel-perfect arch.

"Your lips will look amazing after I'm done with them."

She used a cherry red lipliner to trace Jessie's lips then brushed in the lipstick and finish with a shimmery gloss.

"Wow! Your lips look so kissable Jessica!"

"Are you coming on to me Ashley?" Jessie half-way joked.

"Nope, just admiring my work. Now let's get you out of those curlers & finish your hair."

Ashley removed Jessie's curlers and brushed his hair using hairspray to style it into a curvy, wavy mane. He looked a lot like Mylee Cyrus she thought finding herself just a tad jealous.

"Take a look!"

Jessie stood up and looked at himself in his full length mirror. His makeup was definitely dramatic. He hardly recognized himself. He looked so grown up he thought.

"I can't believe how different I look. My eyes look amazing! What do you think Jason will say? Is it too much?

"Jason will love it. I guarantee it 100 percent."

"Do you do help Jason with makeup as well?" Jessie asked obviously a little cloudy & confused.

"Honey, Jason doesn't wear makeup. Jason is a boy & it would look silly on him."

"But I'm a boy also so why am I wearing makeup?" Jessie asked trying to focus on his train of thought. Something wasn't right about this.

"Do you think you look silly with makeup on?"

"Ummm, no. I think it looks good on me. But I'm a boy...I don't get it."

"Jessica, you are a boy who has breasts. The same thing that has given you breasts has also changed certain aspects of your body. You don't just develop breasts & that's that. Let's take your face for instance, it has softened and rounded a little which is why makeup looks so good on it."

"You like the skirt I let you burrow Jess?'

"Yeah I do. Very much so."

"Well whatever caused you to develop breasts has also given you beautiful curves. Look at how your waist is so tiny then your hips and butt flair out and then your legs gently curve down to your knees. "

Jessie admired his rounded butt and how curvaceous his legs were.

"Jason could not wear a skirt because he would look ridiculous in it. Boys do not have curves & their knees are knobby and too muscular. "

"So Jason would want to wear a skirt if he looked good in it then?"

"I don't think so. Boys don't like to wear such girly things."

"But I'm a boy Ashley!" Jessie stammered.

"Sweety, you are a boy but your body is more suited to wearing girl's clothes. They don't make boy's clothes to accommodate breasts or wide hips. You couldn't even fit in your boy's underwear anymore which is why you have to wear panties. You don't really have a choice in the matter. You are a boy with a girl's body so just enjoy it baby."

Jessie tried to take in what she was saying but once again found the mental block he always ran into.

"Listen Jess, just enjoy the fact that you get to get all dolled up. I mean I let you burrow my prettiest pair of panties so cheer up!"

Ashley reached under Jessie's skirt and pinched his nylon covered butt.

Jessie brushed her hand away feeling embarrassed as he held his skirt tightly against his legs.

"Hey Ashley, that's not nice!"

"Come on Jess, let me see your panties. Just a peek."

"No way! You're embarrassing me."

"Oh come on...let me see!" Ashley replied as she jokingly started to lift Jessie's skirt.

"Hey!" Jessie cried just like a girl as he batted her hand away and squealed.

"Come here pretty girl and let me see your pretty pretty panties!"

They wrestled back and forth a little and Jessie was stunned at how strong Ashley was. He had a hard time believing it, but she overpowered him as she wrestled him to the ground.

The two rolled around for a minute and Jessie grew even more embarrassed as his skirt kept flipping up around his back.

"Aha, those panties look mighty sexy Jess!" Ashley teased as she pinned Jessie down on his back holding his arms to the ground.

"Hey, let me up! You're going to ruin my hair & if I get a run in my pantyhose your dead."

"Oh is poor Jessica worried that she's gonna get a run in her silky, sheer pantyhose? We wouldn't want our little girl to cry would we?"

Jessie tried to force his way up but couldn't budge. How the heck did Ashley get so strong?

"Yes, now stop!"

"Ok silly. Here get up. I was just having some fun."

"Yeah, lots of fun...ha ha." Jessie griped.

"Come on Jessica. I'll fix your hair and then we'll get out of here. Still upset about having a girl's body?"

"Why would that upset me?"

"Yeah, good question."
 

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To Be Continued...