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Request by TheMarioGamer!

Caption text:
"Please Tom, this college assignment is really important to me and I need a model" Jolene begged her brother.
"Can't you get one of your friends to do it?"
"I was going to but she bailed at the last second. Come on I'll even pay you. How does $300 sound?"
"Wait really? $300?" Tom responded in a bit of disbelief.
"Yes I need to make sure this assignment goes well, I'm desparate" Jolene pleaded with a teary look in her eye.
"Fine I'll do it" Tom gave in to his sister's demands.
"Yay! Let's get you dressed up then" Jolene exclaimed excitedly.
Tom then spent the next hour getting made over by his sister. She started with his face, using tons of makeup to turn it into that of a pretty girl. Black eyeshadow and thick mascara helped create a sultry smokey eye while nude lipstick put Tom's lips into a sexy pout. This was followed by a medium length brunette wig that beautifully framed Tom's made up face. Jolene then stuck a pair of breast forms to her brother's chest, giving the illusion of his own boobs. With that out of the way she could get to the outfit. A black tank top covered Tom's 'breasts' while leaving his stomach on display. Black latex pants followed, being extremely tight and emphasizing Tom's ass. Lastly was a pair of tall black 6-inch platform boots that forced Jolene's feminized brother's feet into a slant. Now that Tom was all dressed up, Jolene took her brother to her car for a drive.
"So where are we going again?" Tom questioned as it seemed like they were driving quite far.
"I need a few photos of you in the city and we're going a little farther out so nobody will recognize you"
Tom silently accepted this as he sat back.
"Alright we're here. Now go lean up against that wall, that should make for a good shot" Jolene said with a grin. Her plan was working perfectly.
Tom obeyed, walking up to the wall and posing against it. However when he turned around, he saw his sister revving her engine.
"Have fun getting home 'sis'! And by the way those clothes are glued to you so don't think about taking them off!" his sister shouted before speeding off.
Dressed up as a girl with no phone or money, Tom started his journey home, one high-heeled step at a time.

All characters are 18+

Description
If you want to get early access to captions, view exclusive bonus captions, and even request your own captions, you can support me on Patreon!
www.patreon.com/shabla

Request by TheMarioGamer!

Caption text:
"Please Tom, this college assignment is really important to me and I need a model" Jolene begged her brother.
"Can't you get one of your friends to do it?"
"I was going to but she bailed at the last second. Come on I'll even pay you. How does $300 sound?"
"Wait really? $300?" Tom responded in a bit of disbelief.
"Yes I need to make sure this assignment goes well, I'm desparate" Jolene pleaded with a teary look in her eye.
"Fine I'll do it" Tom gave in to his sister's demands.
"Yay! Let's get you dressed up then" Jolene exclaimed excitedly.
Tom then spent the next hour getting made over by his sister. She started with his face, using tons of makeup to turn it into that of a pretty girl. Black eyeshadow and thick mascara helped create a sultry smokey eye while nude lipstick put Tom's lips into a sexy pout. This was followed by a medium length brunette wig that beautifully framed Tom's made up face. Jolene then stuck a pair of breast forms to her brother's chest, giving the illusion of his own boobs. With that out of the way she could get to the outfit. A black tank top covered Tom's 'breasts' while leaving his stomach on display. Black latex pants followed, being extremely tight and emphasizing Tom's ass. Lastly was a pair of tall black 6-inch platform boots that forced Jolene's feminized brother's feet into a slant. Now that Tom was all dressed up, Jolene took her brother to her car for a drive.
"So where are we going again?" Tom questioned as it seemed like they were driving quite far.
"I need a few photos of you in the city and we're going a little farther out so nobody will recognize you"
Tom silently accepted this as he sat back.
"Alright we're here. Now go lean up against that wall, that should make for a good shot" Jolene said with a grin. Her plan was working perfectly.
Tom obeyed, walking up to the wall and posing against it. However when he turned around, he saw his sister revving her engine.
"Have fun getting home 'sis'! And by the way those clothes are glued to you so don't think about taking them off!" his sister shouted before speeding off.
Dressed up as a girl with no phone or money, Tom started his journey home, one high-heeled step at a time.

All characters are 18+