The Softening of Jessie Part 2
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The Softening Of Jessie (Part 27) free porn video
The two began heading out when Jessie realized that he did not have his
wallet.
"Hey Ashley, how the heck do I carry my wallet? There aren't any pockets
in this dress."
"Yep, most dresses and skirts don't have pockets," Ashley replied.
"I have something that will help," Jessie's mom said.
She left the room and came back a minute later with a small light peach
colored purse.
"Put your stuff in here and carry it along."
"Cool. I could put some cool stuff in here," Jessie replied at the small
feminine purse.
"Yeah, I agree...here ya go, put these in there and let's go," Ashley
replied as she stuck her lipgloss, eyeliner and compact in his purse.
The two headed to the mall to have lunch. Ashley was amazed at how well
Jessie adapted to wearing a dress. It was like he had been wearing one
for years.
"So I take it you will be wearing a lot more dresses from now on Jess?"
Ashley asked.
"Ummm, yeah. I think so. I still wonder if it makes me look girly. I
mean I know it looks better with pantyhose than my shorts do, but I'm
just kind of self conscious."
"It's OK, you'll get used to it...just like you'll get used to the
nickname Jessica," Ashley teased.
"Hey now! That doesn't even make sense, so I will not even dignify that
with a response."
As the two finished up lunch they headed to walk around the mall.
"Don't forget your purse Jess. It will take a while for you to get used
to carrying one, but pretty soon it will be second nature and you will
feel naked without it."
"I have to go to the bathroom. I will be right back," Jessie stated.
"I'll go with you," Ashley replied. She knew she was going to have to
talk him into using the girl's bathroom somehow.
Jessie veered straight for the men's room and began pulling the door
open.
"Hold on a sec Jess. You can't use that restroom today ok?"
"Huh? Why not? Is this restroom out of order or something? Did I miss
the memo?" he asked.
"Ummm, no sweety. You see, you're not dressed properly to use the men's
room."
"What do you mean?"
"Well look at the two figures on the doors and you tell me which one
looks the most like you ok?" Ashley challenged him.
Jessie looked at the symbol of the man with pants on and then he looked
at the symbol of a woman wearing a dress. All of a sudden he got very
confused. He looked down at himself and could see his cleavage showing
through the top of his dress. Looking past that he could see the opening
of the dress end and his nylon covered legs begin. He definitely
appeared to be identifiable with the symbol of the woman.
"I don't get this Ashley. I am a boy, so I need to use the men's room."
"Yeah Jess, but you are a boy who is wearing a dress so you need to use
the restroom that has the dress symbol on it ok?" Ashley tried to
rationalize with him.
"But people will look at me weird if I use the women's restroom. I don't
want people screaming if I walk in there."
"Trust me sweetie, no one will scream. The women's restroom is for
people who wear dresses like the symbol shows. You will get screams from
the men's room if you go in there...that restroom is for people who wear
pants and shorts and you are not one of them."
"Ok I guess. But if I get in trouble I'm blaming you," Jessie promised
feeling very nervous about using the women's restroom although Ashley's
logic made perfect sense.
"One thing though Jess. You are going to have to sit down to pee ok?
Standing is not allowed in the lady's room."
"No worries there. I always sit to pee," Jessie replied.
The two entered the women's restroom and Jessie was surprised at how
well maintained it was. It smelled nice and looked so pretty. He also
noticed that there weren't any stand up urinals but instead there were
more stalls. This is like the perfect restroom he thought. Those stand
up urinals were so useless he thought.
Jessie entered the stall next to Ashley and lifted his dress, pulled
down his pantyhose and panties and did his business.
Ashley heard Jessie tear a piece of toilet tissue and then flush. He was
just like a girl now she thought.
"Now you want to take this chance to freshen up a little if you need to
Jess. Check your make-up especially your lips."
Jessie looked at himself in the mirror. He looked different somehow. He
knew that there was something very odd about checking his makeup in the
mirror of a women's restroom but he couldn't place it.
"I think my lips may need some more gloss maybe?" he ventured a guess.
"Yeah, I think they do. You want to apply it or should I?"
"I can do it I think," he said as he popped the cap off the pink
shimmery lip gloss. He carefully and slowly ran the tips over his top
and bottom lip until his lips were coated with the syrupy gel.
"Well done Jessica! Very pretty lips!" Ashley praised.
Jessie was proud of the taking control of his makeup and showing Ashley
he could do it by himself...although he was a little bent that she was
still rubbing the Jessica nickname into him. He decided he wouldn't get
upset though because he knew she would do it more if she knew it made
him mad.
"Oh sweetie you have a run in your pantyhose," Ashley stated as she
noticed him walking out.
"Huh, where?"
"On the back of your right leg just above your ankle."
Jessie turned around and sure enough there was a run that extended from
the top of his heels to the top of his calf.
"Dang it! What should I do?" Jessie asked. He was upset that this was
the second pair of pantyhose he had ruined.
"I have some nail polish if you want to use it," a woman in the restroom
volunteered.
"Oh thanks. That's very nice of you," Ashley replied.
"What's nail polish going to do? My nails are already painted," Jessie
asked, bewildered by the offer.
"Oh girl, this is one of those things every woman should know. Nail
polish will stop the run from getting any larger until you can find
another pair of hose," the woman replied.
Ashley took the polish and applied it to the back of Jessie's leg.
"There a go. Thanks a lot," Ashley said as she handed the woman back her
polish.
"My pleasure. I really like that dress by the way," she said as she was
happy she helped the young woman fix her run.
"Thanks, it's actually Ashley's, but she let me burrow it."
"Well that's what friends are for."
The two left the restroom and walked around the mall for a while.
"Hey sis, you have $5 I can borrow?" a familiar voice said.
Jessie turned around and sure enough it was Jason...his ex-best friend.
Jessie was so hurt by the way Jason had treated him since his breasts
started hurting a while back. The two never spoke anymore and this was
completely due to Jason's behavior. Jessie decided to give Jason the
complete cold shoulder and just ignore him,
"I'm not letting you borrow any money little bro. Did you ever pay me
back the last time I lent you some cash?" Ashley asked him. She noticed
him look at Jessie and was hoping there wouldn't be any problems.
"Ummm, yeah I did. At least I thought I did. I mean if I didn't I'm
sorry," Jason replied. He suddenly found himself very nervous because of
his sister's friend. She was hot! He hadn't seen her before either, but
she was so pretty and those boobs...wow!
"Well well well, do I sense a little guilt in your voice Jason?' Ashley
asked. She noticed him acting a little wierd and he looked at Jessie
very strangely.
Jessie on the other hand felt uncomfortable with the way his former
friend kept glancing at him. I mean how rude was he? He didn't even say
hi. It was obvious that Jason was nervous because he was fidgeting. Why
would he be so nervous? Perhaps it was because he was a complete
jerkoff?
"So what are you two girls up to? Jason asked. He tried to gain his
composure in the presence of the pretty friend.
"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!
"You find anything cool yet?" Jason asked looking directly a Jessie.
Jessie didn't know what to do. Sure he wanted to give Jason the cold
shoulder but he could sense a certain friendliness in his voice.
"Not yet," Jessie replied.
"I'm Jason by the way...Ashley's good looking brother," he stated trying
to act suave.
What was up with him? Was he just being a smart ass introducing himself
after they had known each other for so long? Or maybe he was just trying
to start over from scratch.. Jessie didn't know what to think.
"This is my friend Jessica and we have become great friends," Ashley
replied.
There she goes again Jessie thought...calling me Jessica. He wasn't
going to let her embarrass him in front of Jason though so he didn't
throw a fit.
"Yeah, Ashley is a great friend. She likes me in good and bad unlike
some people I know," Jessie sharply said.
Jason didn't know what that meant but he was glad the pretty girl wasn't
talking about him.
"Well we better get going bro..."
"OK, hey it was nice talking to you Jessica. I think that dress looks
real pretty on you," Jason replied.
Jessie was flattered by Jason's comment on his outfit. This was the
second compliment today on his dress. It mustn't have been too girly if
he received high marks from the woman in the restroom and from Jason.
He found it mildly amusing that Jason had also jumped on the "Jessica"
bandwagon...he was always the joker.
"Thanks...I got a run in my pantyhose which kind of sucks, but what can
you do?" Jessie replied.
"Yeah, well I'm sure your legs look great with or without pantyhose on
if that makes you feel any better," Jason replied as he tried to sweet
talk Jessica.
"Thanks Jason! That was very sweet of you to say. You're not that big of
a jerk after all maybe," Jessie stated as he gushed at how cute Jason
was acting. Perhaps he should give Jason another chance.
"Hey, did you tell her I was a jerk sis?"
"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. She thought it best to leave before something awkward was
said though.
"You and Jason seemed to get along ok today didn't you?"
"Yeah, he was being so sweet to me...maybe he wants to be friends again.
I miss hanging out with him," Jessie replied.
"Oh, I'm sure he would love to hang around with you now...you can thank
your boobies for that one."
"Huh?"
"I'm telling you Jess, breasts are powerful. Now let's do some
shopping!"
Emely
- 10.08.2022
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