The Softening of Jessie Part 2
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The Softening Of Jessie (Part 26) free porn video
Ashley reached into her bag and pulled out a pair of white open toe heels
and presented them to Jessie.
"These will look good with your outfit. Why don't you try them on?"
"I don't think so Ashley. You're not going to get me to wear heels...
those are girl's shoes," Jessie replied. He was taken aback from the
offer.
"Oh come on Jess, you can't wear a pretty dress and sneakers! Get real
sweety. You need to complete the outfit. Besides, these shoes will show
off your pink toes...you want that don't you?"
"Ummm, yeah that would be nice, but I'm not wearing girl's shoes. That's
where I draw the line."
"Hun, you're wearing one of my dresses, so I don't think the heels are
that much of a leap. Fine then, if you're not going to wear the shoes
then take off my dress and give it back," Ashley countered.
"You want me to take off the whole outfit?" Jessie asked. He had grown
fond of his borrowed dress.
"Yep, you can walk around in your shorts and pantyhose for all I care.
You make the choice. I'll let you wear the dress if you put on the
shoes... or else the whole outfit comes off."
Jessie thought about the ultimatum. He really liked how the dress looked
and felt and didn't want to give it back. He decided he would compromise
and wear the shoes. The thought of showcases his well painted toes was
very appealing as well.
"Okay I guess. Give me the shoes," Jessie replied as he grabbed the shoes
and slipped them on. They were very delicate in nature with thin straps
and a high heel in back that made him look tall. He thought it was pretty
cool that he could grow an inch or two just by putting on a pair of
shoes.
"Wow, sexy girl!" Ashley said as she admired how well the heels looked.
"It's a good thing we are about the same foot size huh?"
"Yeah, good thing," Jessie said sarcastically acting like he didn't like
the new shoes he had on. He admitted to himself however that they did
look really nice. He liked how he could see his nylon covered toes
through the open straps of the heels.
"Stand up and see if you can walk in them Jessie."
"Ok, he we go." Jessie got up and proceeded to walk from one end of the
room to another without a misstep. It was as if he had been wearing heels
for years. Ashley was amazed at how gracefully and feminine he sashayed
from one end to the next.
"You are amazing Jess! Are you sure you haven't worn heels before?"
"Positive...not bad huh?" he replied as he did a twirl in his pretty
dress.
"Look at you! You look amazing! Now let me just put a little makeup on
you and then we're done," Ashley said as she got her makeup bag. When she
returned she noticed Jessie sitting on the edge of the bed with his legs
crossed and his back slightly arched back with his hands folded on his
pantyhose covered knee. He had such incredible female etiquette.
"You sure you haven't worn a dress before? You really know how to sit
properly."
"What do you mean?" Jessie replied. He was not aware he was sitting in
any way out of the usual.
"Well keep sitting the way you are now whenever you wear a dress. The
last thing you want is for people to be able to look up your skirt."
With that Ashley applied a little eye shadow, liner and a touch of
shimmery lip gloss to Jessie face.
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?"
"Don't know...that's my new nickname for you though...I think it sounds
cute."
"Yeah, cute huh? Real cute...not," Jessie replied at her strange
nickname.
"Ok, let's go get some lunch, Jessica," Ashley replied as she gave Jessie
a sly wink.
"Hey, I thought you were going to wear a skirt if I put on the dress?"
"Oh yeah, fair enough."
Ashley pulled down her shorts and donned her jeans skirt. Jessie knew
that he should be excited seeing such a pretty girl in her panties but he
just wasn't feeling it.
"Ok, let's go girl."
The two headed downstairs to head out for lunch and ran into Amanda and
Susan.
"Hey mom...grandma, we are going to go out to lunch."
The two ladies stood there speechless at what they beheld. Sure, Jessie
had been growing more and more feminine as the weeks passed, but this was
a shocker. What they beheld was a beautiful young woman wearing a pretty
dress, high heels, a cute ribbon in her hair and shimmery makeup. What
was even more amazing was how oblivious Jessie was to the changes that
had taken place and the clothes he was wearing.
"Honey, that's a very pretty dress you have on," his mom commented.
"Thanks mom. Ashley is letting me borrow it, which is something big since
she says she is so possessive of her clothes," Jessie joked.
"Yeah, I decided I'd be a nice person and lend her it. I even put on a
skirt to make her feel more comfortable with her dress," Ashley replied
freely using the feminine pronoun.
"You're lucky to have such a nice friend Jessie. How do you like wearing
a dress...and high heels even huh?" his mom asked.
"I think I like it mom. I don't think I've ever worn a dress before. If I
have I can't remember. Is that weird...I mean I must have worn dresses
before right? How come I can't remember...did I wear dresses or skirts
when I was a little boy?" Jessie asked rather confused at why he could
not remember wearing any dresses or skirts. He could not connect the dots
that boys do not wear dresses.
"Honey, yes you wore dresses all the time...it's ok if you can't remember
though," Amanda replied. She didn't know what to say to that question so
she decided to change the subject.
"You really fill out the top of that dress Jessie...you may want to be
careful when you lean over," Amanda stated as she noticed his very full
looking breasts which were showcased in the low cut front of his dress.
"Oh...yeah," Jessie said blushing. "Ashley let me borrow one of her
strapless bras. I think it pushes my breasts up more than my usual bras."
"Your breasts Jessie?" Amanda asked. Did he realize and accept that he
had breasts?
"Yeah, my breasts mom. You could see my bra straps, so luckily she had a
better bra for the dress."
"Yeah, I also told Jessica that those boobs are powerful tools," Ashley
butted in.
"Jessica huh?" His mom asked.
"Uhhh, yeah. That seems to be Ashley's new nickname for me...pretty lame
if you ask me."
"I kind of like it and yes your breasts can get you a lot of things
honey. You have to be careful how you flaunt them though because you
don't want to develop a bad reputation."
"I have no idea what you're talking about mom...and I don't want to
know."
"Well you two have fun at lunch then and be careful in those heels
Jessica," his mom replied.
"Hey! You calling me that name too Mom? Yeah yeah yeah, rub it in. See
what you've done Ashley?"
"Yep, get used to it sweety. I think that nickname's gonna stick."
Jerri
- 18.12.2020
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