"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

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Jessie grabbed the phone and gave Ashley a call.

"What's up Ashley?"

"Hey, I wanted to see if I could spend the night at your house. Jason is having some of his friends over and I don't want to be here with those boys."

"Jason invited friends over for the night and didn't include me huh?" Jessie replied. He knew that his friendship with Jason was strained but it still hurt to be not included.

"Yeah...sorry, but I'll hang out with you tonight. I promise I don't snore. Besides we could have lots of fun together," Ashley responded.

"Yeah, there's no way. My mom would never let a girl stay over with me all night. She'd be too freaked out that I'd get into trouble...you shouldn't trust me either. I'm pretty much a magnet around the ladies," Jessie half joked.

"Oh I see...I think I can handle you. Ask your mom," Ashley responded holding back a laugh. Jessie's masculine traits were all but gone and she didn't care for girls.

"I'll ask but I already know what the answer is."

Jessie called out to his mom.

"Mom, Ashley wants to know if she can come over for the night."

"She wants to spend the night?" Amanda asked.

"Uh yeah. I told her that it's a dumb idea."

"Well I think it might be alright. She's a nice girl."

"Really? But she's a girl mom...and I'm a boy...do you follow me?" Jessie asked rather dumbfounded.

"Yeah, I know. Just keep the door open then," Amanda replied to her very feminine son.

Jessie scratched his head and picked up the phone.

"She said it's cool. You can come over."

"Awesome! I'll be by around 5 and I'll bring stuff to play with. We are going to have so much fun!"

Ashley arrived at 5 with her duffel bag. The two ate dinner and chatted with Amanda and Susan for a while. Before long the two decided to head up to Jessie's room and get ready for bed. Jessie went into the bathroom in the hallway while Ashley used his bathroom to change into her pajamas.

Ashley quickly put on her blue plaid sweats and yellow tank top and chilled on Jessie's bed. Jessie came in the room shortly after.

"Wow, I'm stuffed from dinner. I think I could eat dessert still though," he stated.

Jessie was donned in a light yellow nightgown made of nylon that came to rest just above his knees. It had a white lace trim around the shoulder straps and around the skirt. For all intensive purposes it was a dress. Ashley was amazed at what he was wearing and the fact that he didn't even realize that he was in such a feminine outfit.

"I like your pajamas Jess."

"Thanks, it's comfortable to sleep in."

"Do you wear pantyhose to bed too?" Ashley asked noticing that his legs were still encased in sheer nylon.

"Yeah...I just like the way they feel. Plus they keep my legs warm at night."

"Yeah, you'll get tired of wearing them sooner or later."

"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."

Jessie thought about her statement and gave in to her request.

"Good, now sit back and let me do my work. First thing I want to do it trim your eyebrows a little. They are way too bushy girl," Ashley stated using the feminine pronoun.

"Don't make me look silly ok?"

"Oh I won't".

Ashley pulled out the tweezers and had Jessie lay his head on her lap. He looked so cute in his nightee she thought. Jessie wasn't sure what to think. One part of him knew he should be in heaven to be so close to such a pretty girl, but the other part just felt very comfortable and relaxed.

PLUCK. "Ouch," Jessie yelled.

"Oh calm down ya big baby...no pain no gain," Ashley replied.

PLUCK PLUCK PLUCK

"That hurts Ashley," Jessie stated grimacing in pain.

PLUCK PLUCK PLUCK PLUCK PLUCK PLUCK

The plucking went on for what seemed like an eternity. In fact it was quite a while. Ashley's finished job resulted in very thin, highly arched brows which were unmistakably feminine.

"Can I see?" Jessie asked.

"No not yet, we are only getting started. You have to wait until I am finished," Ashley replied. She was amazed at how the plucked eyebrows made him look completely different...completely girly.

Ashley opened up her makeup case and sat Jessie up.

"I'm going to do your face up ok?"

"Like what? A clown?"

"Yeah, sort of...only not really...promise not to move ok?"

"Ok, I can have a sense of humor about this."

Ashley opened up her bottle of foundation and placed a bit on her sponge. She blotted it all over Jessie's face and smoothed it in with the sponge.

"That stuff smells funny but good," Jessie stated.

"I'm going to apply some powder now. It will give you skin a porcelain finish," Ashley replied as she used her brush to gently cover his face with the delicate powder.

"Now I'm going to make you eyes look pretty. Close them please."

Jessie reluctantly closed his eyes. He felt a brush sweep across his right eyelid and then his left. The brush then went back to his right eyelid and was brushed over it several times. The same was done to the left.

The he felt what seemed like a wet felt tip pen trace over his upper right eyelid. The same was repeated on his left.

"Open you eyes now," Ashley said as she used the eyeliner pen to line his lower eyes.

"Now I want for you to look up at the ceiling and don't flinch...it's important that you don't move ok?"

"OK."

Jessie looked up as he saw a black wand with tiny bristles on it come close to his eyes and brush his upper eyelashes several times. It was uncomfortable and he wanted to move but did as Ashley requested and stayed still. She then took the brush and did the same to his lower lashes.

Jessie somehow felt weird about what was happening. It didn't seem quite right but the more he tried to think of why it wasn't normal the more he drew a blank.

"Perfect."

He then saw her pull out what looked like a dark pencil. He felt the pencil trace his eyebrows.

Ashley grabbed her red lip liner and began tracing Jessie's lips.

Jessie was amazed at how good Ashley was at this. She seemed very confident and self assured. .

As soon as Ashley traced his lips, Jessie saw her pull out a tube and pull off the top. She then twisted the base and a lighter red cylinder came to the surface.

"Open you mouth a little....just like that"

Ashley carefully but deftly applied the lipstick to Jessie's lips.

"Now move your lips back and forth to smooth your lips over then blot them on this Kleenex."

Jessie did as instructed and saw the red lip prints that were left on the
tissue.

"Wow, you look amazing!" Ashley said. She choked back a tear as she was stunned at how pretty and downright girly Jessie looked all made up.

"You OK Ashley?" Jessie asked noticing her emotions.

"Yeah, I'm fine. It's just that you look really great is all."

"Now for the hair!" Ashley excitedly stated as she plugged in her curling iron.

"You're going to curl my hair?" Jessie asked.

"No, it just adds some volume and a few twists."

She took the iron and curled his hair in several places then brushed it out.

There was a lot of room to play with. His hair was beautiful and down to his shoulders. Ashley brushed out his hair and applied some hairspray to hold it in place.

She stood back and admired her work. Jessie was all girl without a doubt.

"Ok, go look at yourself Jess."

Jessie got up and went to the bathroom and he momentarily lost his breath.

"Wow, is that me?" he asked. He was amazed at how different he looked.His eyebrows were pencil thin...his lips red...his eyes outlined in black with a blue green tinge to his lids.

"Yes, what do you think?"

"I look really different," Jessie replied. There was something that wasn't right...what the heck was it? He couldn't place it... "But I like it!"

"Really?!? I am rather good at makeup I have to admit," Ashley replied.

"Yeah, I think it looks cool. Can you show me how to do it too?"

"Yeah. I'm glad you like it. I can show you lots of cool tricks. Makeup is a lot of fun."
 

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To Be Continued...