Panty thief's paradise
Most boys dream of girls, but Jacob wants to be one! He seems normal but secretly enjoys crossdressing but will he continue, or get caught?
This is my first story cut me some slack please! Enjoy!
There it was just what he had waited all night for. Jacob a 14 year old arctic fox he was a small lean fox his feminine physique had forced him to be very anti social and didnt talk much to his family or friends. He had been staying up all night in his room till 1:00 AM to sneak into the bathroom it wasn't that there was a long wait inside the bathroom his sister kept some makeup under the sink for when she needed it the good stuff she kept in her room. Jacob liked it when he wore makeup and loved it when he wore it with his sisters dresses. It all started with a pair of pink panties back when he was younger he had shared a room with her ,which caused them to separate and not talk anymore, he was curious and he had wondered what it was like to wear them she left them all over the room anyway she wouldn't notice so he slipped them on. After that he couldn't stand to wear anything else, but he needed more he would steal a piece of clothing here and there the more girly the better.
Jacob knew what he was doing was bad and if his family found out it would never be the same. But it felt so good against his body the soft fabric against his small member was exciting and felt right. since he had to share a room with his brother it wasn't easy to wear all that he wanted. He would put on a pair of panties and a sports bra underneath his clothes but he had to wear jackets and hoodies to hide the straps. All the clothes he got were just what his sister hardly wore. This night though his brother was gone off to some party, he didn't care. He breathed heavily and checked his watch 1:17 his nails clacked on the floor as he creeped down the hallway towards the bathroom. Luckily his night vision was good and a full moon was out ,he hid himself in a black sweatshirt and black pants with a pair of panties underneath,his usual attire, He slipped into the bathroom and moved for the sink but bumped the door instead, damn he muttered , pulled out his penlight and started to loot the cabinet only some of the basic items he didn't want to be greedy.shoving them in his pockets except the lipstick and mascara he pulled out his pocket mirror and started to freshen up and admired his work since he had gotten very good. just when he was about to leave he noticed his sister walk past. He didnt expect this and shrieked out just a little too loud (much like a girl) and hid in the shower behind a curtain. "whats she doing up he wondered* after a good 15 minutes he scurried back to his room.
Whew that was close one he thought at lunch as he sat with his friends (mostly girls) that found him cute and tolerated his presence. He wished he could ask them to help him, dress him up, show him how to look pretty, do a girls night, but he knew it would never happen.Later that day...Jacob sat in his room finishing up his homework, his brother was out for the weekend again with his friends he always got to do what he wanted. His sister was also out which meant that he had the perfect opportunity to get some new clothes his old ones were all cumstained and dirty. he finished up his homework his parents were in the living room watching the same TV show they always watched. and creeped down the hall it wasn't long their house was small, he knew he had to make it quick he opened the drawers quietly and started to look. Much to his disappointment it was mostly socks and sports underwear his sister wasn't too much of girly girl but he was. He knew he couldn't get anything that she wore often or just bought which really limited his choices.
Just as he was about to move on he felt something soft "bingo" he said underneath his breath. Out he pulled out a pair of light pink silk tight panties. This should he good but he wanted more he needed more, he bored of the cloth panties and undershirt he had taken. He started to look through closet for something more. as he looked through the sweaters and jackets something caught his eye in the back.He gasped, there it was a a a white dress with pink frills with sleeves but a skirt that was quite short. He knew he shouldn't take it a dress like this would surely be noticed if it went missing but this dress was perfect. Just for tonight he thought. He grabbed his favorite pair of heels ,due to his frame he could wear just about all her clothes with ease, and a pair of pantyhose to help. No more no more he had to tell himself. Shoving it in his pants and under his jacket he snuck back to his room unnoticed.
Whew! He exclaimed as he put all the clothes on the bed."Oh boy!" he giggled as he thought of all the fun he'd have tonight. He started off with putting on the underwear the silk panties and a white bra and moved on to makeup.He was going full out tonight painting all his nails, pink strawberry lip gloss, blush, heels , and the dress. "Damn I look cute" he said as posed in his mirror.Already there was quite a bulge and dampness in his panties this only added to how horny he was and started to stroke his cock. He plopped down to his computer and went to his favorite femboy's gallery. He couldn't hold back before he even got to the 3rd picture he came and harder than ever before splattering the dress and his face and ate it all.
He layed in bed and hadn't taken off any of it he liked how it felt even if the heels were a bit tight. This is the best jacob thought he whimpered a little at the thought that he couldn't wear it all the time. As drifted off to sleep he dreamed of what it would be like to be a girl so nice so feminine his name would be julia and pink would be his favorite color.
"jacob...jacob...JACOB!" eek he shrieked. His sister was standing over him next to his bed with a camera pointed on him and his blanket was removed.
oh shit the dress! But when he tried to moved he couldn't "what the hell!" he barked, his paws and legs had been tied to the bed posts.
"don't worry I know about the dress and all the times you wore my clothes" his sister,sarah, said.
"h-how l-long did you know" he stammered nervously. "oh quite a quite a while now from all the times I found cumstains in my panties, I put up hidden cameras to find out who it was."
Jacob gulped it was his worst nightmare come true. He started to whimper and sniffle "please don't tell anyone I'll do whatever you want, please!" he begged.
"Whatever I want?" sarah asked tentatively.
"yes yes just don't tell mom or dad" He cried
"and ruin the all the fun come on jacob." sarah said jokingly "sides you do look pretty cute in that dress your going to be my little sister now"
"h-huh?" He was so confused his sister had was always disgusted by him now he knew why.
"tsk tsk and here I thought you'd be happy this is what you want right to wear whatever clothes you want and you won't have to hide them either it's your little pervert fantasy right?"
"I-i um thank you sis what do you mean though?" he wondered
"that's the good part I'll get to dress you up all I want and you'll get beat off in them and choose whatever fetish you want and I'll video tape it, I won't show anyone it'll just be our little secret sissy"
"do I have to do it on tape?" jacob asked
"not all of them don't worry but you try to back out of this and I'll show mom and dad these pics of you in that dress."
"ok ok" What could he do she had the evidence?
"But before I let you go for now you have to jack off in front of this camera for stealing my good dress,don't worry you're already pretty hard" she laughed and undid the bondage. Sarah flicked on the camera "time for you to go to work faggot, get on your knees"
Jacob obediently followed his sisters commands and started to masturbate "now finger yourself sissy" sarah barked. And in went his two digits causing him to pant in the ecstasy and heat. "good girl"
"now tell me what are you?" sarah asked slyly "a sissy" jacob said as he pawed himself off harder. "And what do you love to wear?" she asked "girly clothes" he said as he added an extra digit to penetrate his tight femboy hole and moaned loudly. "oh you're such a dirty girl what's your name sissy?"
"Julia mistress" jacob panted
"good girl julia now cum for me!" sarah ordered
Jacob didn't need the order he was already at the edge of his climax and came all over himself and the bed "now lick it up bitch" sarah ordered
Jacob thought to himself. "I could get used to this"