Jesse in a dress, silk stockings -and high heels!

TG FICTION by Debbie Sweetreet
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"Jesse in a dress, silk stockings -and high heels! "

Jesse sat primly, as been instructed, gracefully crossing his smooth, shapely young legs reveling in the sensation of the light-taupe silk stockings, sending yet even more flurries of butterflies through his tender tummy.

He gently d****d the flaring of the soft pastel-yellow floral summer dress over his "pretty, little knee-caps," as his Aunt Melissa called them. The dress was so light and feminine, ruffled sleeves that lay off the shoulders high-lighted the boy's slender, rather girlish figure. Jesse had always been a dainty and slender boy, further enhanced by the fact that his mother let him grow his strawberry blonde hair long and now down his beautiful back.

But now his hair had been restyled into flowing locks of sprightly curls, an adorable daisy hair-clip accented the delicate femininity of his now very, girlish appearance. This was truly going to be the most remarkable summer ever for Jesse! From the very first few moments of arriving at his Aunt Melissa's he was lovingly informed that he would be spending the next several weeks together as a "sweet niece and her adoring auntie." Melissa explained, leading Jesse into his bedroom for the summer where everything that he could ever dream about was ready to help him become a beautiful girl!

Jesse's boy clothes were immediately discarded. Pretty little satin panties with tiny daisies on them were the first thing Jesse put on. They clung to his smooth skin causing his perfect, young cock to stiffen instantly. He reached around to caress the sleek fabric across his tender, rather girlish behind, his fingers shaking with excitement.

A matching, small bralette was next, and with a little help from Auntie Melissa, it was securely fastened to his pretty, smooth chest. His nipples, sprouted stiffly beneath the satin fabric, pink and so sensitive to the wonderful feeling. In just the panty and bra, Jesse looked down at himself then into the full-length mirror and gazed excitedly at the vision of budding ladyhood he was becoming.

But the silk stockings were the most captivating of all! Jesse had been told on more than a few occasions that he had such shapely, feminine legs that most women would envy. Not yet a hair on them, Jesse's legs were sleek, smooth and absolutely made for a pair of silky stockings! The cooling sensation as the stockings caressed his pretty legs was heavenly. When Aunt Melissa placed the lace-topped band delightfully around his creamy, sweet upper thighs, Jesse blushed like an adorable school-girl.

"Now, 'Jessica,'" his Aunt Melissa began, "that's your name from now on, sweetie. You do look like a very cute and precious young lady, so let's put on these shoes now and have you practice walking like a graceful girl." Sliding the small, strappy 3" pumps on his silken clad feet, a playful daisy adorned the top complimenting the lingerie and daisy hair-clip Jesse wore, Melissa helped him to his feet and positioned him before the mirror.

"Jessica's" dick throbbed hotly at the sight of himself so almost completely transformed into a gorgeous young girl. From the cascade of curls falling over his dainty shoulders, to the satin and lace bralette and that amazing matching bikini panty encasing his super-sensitive "boi-clitty,' to the seemingly glowing silk stockings made even more enticing with the daisy-pumps on his feet; Jesse was nearly the example of feminine perfection.

"A lovely and feminine girl always likes a little make-up," Aunt Melissa instructed her 'niece' deftly adding a tad of blush to his rosy cheeks, some mascara to enhance his already thick and fluttery eye-lashes, to a nice coat of glossy-pink lipstick to his pouty, cherubic lips. "A dose of some nice, sweet perfume to make you smell nice and girly,' she said with a smile as she sprayed his neck and shoulders with a mist of SunFlowers perfume. "Now, let's get this dress on and head out for the day, just us girls, what do you say?"

"Jessica" was as thrilled as he ever had been in his entire life. He looked and felt just like a real, cute and lovely girl and couldn't wait to go out and see if maybe he's attractive enough for any boys to notice. He certainly hoped so.
Well, there was only one way to find out, as he took his Aunt Melissa's hand and sashayed out the door...

Published by Sweetreet
2 years ago
Comments
28
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wingaling
wingaling 6 months ago
ooo this is your best one yet~
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glendaa 1 year ago
i will dress for you like this in black stockings with the reinforced toes and high heel open toe !!
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LeslieLesbianLover
I love this!!  I can so relate to it!!!
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slavecum33
slavecum33 1 year ago
thank you for this so erotic story. i love it, Madam Debbie
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LeslieLesbianLover
to Sweetreet : Thank you so Much!!  I would have loved being your sweet girl, Debbi!!  Still would!! 
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Sweetreet
Sweetreet Publisher 1 year ago
to LeslieLesbianLover : Thanks so much for your sweet words, Leslie! You must have been such a charming girl whose hair would be so cute in pigtails and bows! :heart:
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LeslieLesbianLover
love the things you write, Debbie!!  I think I'm in love!!
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LeslieLesbianLover
omg!!!  This story was soooo wonderful to read!!  The dress sounds almost exactly like one I once wore when I was so young!!  I love love love wearing stockings!!  And with lace tops too!! Omg!!!  You won't hardly believe this, Debbie, I had such looong blonde hair and it was soooo curly ( natural curls ) it would have astonished you I bet!!
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Sweetreet
Sweetreet Publisher 1 year ago
to tooljoe : 💋That's nice of you to say...thanks a billion!!!🌈
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tooljoe
tooljoe 1 year ago
so yummmyyyy....just imaging where they were off to....i have some naughty ideas but would love to hear more :wink:
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jerkofffan
jerkofffan 1 year ago
to Sweetreet : My cock is hard!
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Sweetreet
Sweetreet Publisher 1 year ago
to jerkofffan : Thanks so much! :grinning:
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jerkofffan
jerkofffan 1 year ago
Mmm,hot visual.
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Sweetreet
Sweetreet Publisher 1 year ago
to phillymark1 : Thanks so much!
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phillymark1
phillymark1 1 year ago
Fantastic transformation and erotic too.
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May i please be next aunt Melissa???
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redclay56
redclay56 1 year ago
Look out world!
Sweetreet
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Sweetreet
Sweetreet Publisher 1 year ago
to Isisbane : That's so adorable to hear! I'd love to have helped you with your girly things! :heart:
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Isisbane
Isisbane 1 year ago
First started playing dress up as Susan is 8 and then afterwards I was taught how to act and move as well so I started to feel more and more intense pleasure when I'm dressed and ready to play Susan
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zeenacd2
zeenacd2 1 year ago
exciting
Sweetreet
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spontaneo333
spontaneo333 1 year ago
I enjoyed it thoroughly, specially it's narration appeal. One can't help to wonder how would it be like to feed the author a rosey, creamy and silky smooth femme boy from time to time.
Sweetreet
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trannydee1
Brilliant writing well done saw some of myself there getting dressed♥️♥️♥️
Sweetreet
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Julian069
Julian069 1 year ago
Wunderbar! I would like to have a ant Melissa! Kisses 
Sweetreet
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oldjacker67
oldjacker67 1 year ago
More please😋
Sweetreet
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Tomgirls
Tomgirls 1 year ago
Oh nice..wish someone would have dressed me up when I was young with so much care and loving.  I can't wait to read more.
Sweetreet
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Nicolefetish
I enjoyed your the sexy intelligent words because English is my second language, I has been a long night of live show for me, xx
Sweetreet
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JakeKay88
JakeKay88 2 years ago
I could have used an Aunt Melissa when I was that young.
Sweetreet
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tvslut69
tvslut69 2 years ago
It is the dream of every femi man who is aware that he is living in the wrong body.
Sweetreet
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