Sister Transforms Her Stepbrother

This story starts years before her transformation begins, Clarence (Chuck to his friends) had always felt something wasn't right with himself even at an early age around 8 he would rather spend his time playing with the girls and wasn't into things other boys did. He was called sissy, gay, girly and other things growing up causing his father to move away and try to get his son to, in his words man up. His father made him join boy scouts and try out for different sports teams trying to force him into being a guys guy, Chuck placated his fathers wishes but always knew he felt so much more girlish and always considered his small penis was the wrong genitals for him.

Years passed Chucks father met Beth's (his now new stepsister) mother and they married moving into our house which now filled the 3 bedrooms, the parents on the 1st floor and the two children's rooms on the 2nd. Chuck, now 18, got along great with his new 20 year old stepsister but missed the quiet and freedom he had being on the 2nd floor by himself, before Beth he could check out porn and dress in girls panties, bras and nylons while he dreamed of hard cocks as he imagined them filling his imaginary pussy. Now that Beth lived her those moments dwindled to nary a one.

That changed when on weekend their parents left for 2 days leaving Beth in charge, once they left Beth told, "I'm going to go out with Lisa, Jane & Rebecca for the night, we might stay at Lisa's so will you be alright by yourself?"

"Yes, I will be ok by myself have fun," Chuck said as he thought, "finally I can dress up and relieve myself."

The moment Beth and her friends left Chuck raced upstairs and turned his computer to his favorite porn site and reached into the corner of his closet taking out a box buried under a bunch of other boxes hidden well. After getting naked he wraps toilet paper around his small 4" penis and scrotum, once covered he begins to wrap tape around pulling his tiny cock towards his ass crack finally taping it down. Sliding his lace panties on Chuck got aroused as the silk worked it's way up his legs then pulling the shear nylons on Chuck felt another twinge of arousal, pausing a bit so he wouldn't cum while strapped in he finally put his pink lace bra on completing his transformation. As he stood up looking in the mirror he admired how good he looked in what he felt is his natural body, at 5' 5" he had always had a slight girlish curve at 110lbs, his ass stuck out with a firm bump he always thought the boys might like and his long blond hair that fell a few inches below shoulder length looked so good when he put it up in a pony tail.

Turning to the computer he played a video watching two men with a young college girl being fucked from behind by one while sucking the other. Chuck straddled the bed admiring his ass in the air as he imagined the cock sliding into his imaginary pussy. Chuck could feel his tiny cock trying to rip the tape off but he knew it would hold as he rubbed his pretend clit and began moaning and then saying, "oh yeah fuck me big boy, yes fuck me."

Just then his door opens and Beth said, "I'm home little brother," then as her eyes fixed on her brother dressed as a girl said, "what the hell is going on?"

Chuck stammering up said, "please Beth don't say anything please!"

"Are you gay or something what the fuck," she asked.

"Well you see since I was a little kid I felt I was in the wrong body, could you understand that? My dad always tried to make me into a man and he doesn't know I dress up, please don't tell him." Chuck said.

"I know I have heard there are people that feel that way. Let me see you know you do make a better looking girl than a boy, you got a small natural curve to your hips & that ass, I wish mine was that nice & tight. All you need now is a little bit of boobs here let's try this," she said as she wadded up tissue filling the cups. "There you look good with small boobs probably and a-cup I would say."

Chuck admired himself in the mirror and said, "I've always wanted to buy a dress and see if I could pass but I'm too afraid to do so."

"You know we are almost the same size, I wonder," she said walking out the door and a few moments later returning with two dresses, a low cut lacy red one and a light blue one with much less of a cut to it.

"Let's see," Beth said as she held the red one in front of Chuck. "I think the cut is a little too low for a-cups and if I stuff you more I think they'll be too big for you." Then holding the blue one up she said, "This I think will be perfect and I think it will fit you and probably look better on you than me."

Chuck instinctively held his arms up as Beth drew the dress over his head pulling it down finally zipping it up, the fit was perfection. Beth then undressed and put the red dress on both admired themselves in the mirror wen Beth said, "you know we could both go out and pick up some guys right now we're both hot."

Chuck always admired how beautiful Beth was, dark curly brown hair, green eyes 5' 4" about 100lbs, great 32 b-cup breast that jutted wonderfully to a fine point and smooth soft legs. Chuck then looking at himself now thought he made as beautiful as she was maybe even to be honest even a little hotter.

"Ok 1st thing we need to do is shave your legs, that boy hair got to go. Then tomorrow we try out a new club that opened in the city dressed to kill, what do you say?" Beth said.

"Um I don't know," Chuck stammered.

"Come on nobody will know us there and hey we never partied before, we can't drink there, well I can I have a fake id but unless you have one you can't but that's ok." Beth said.

"Ok let's do it, just you and me no friends right?" Chuck said.

"Just you and me no friends," she said.

"Ok lets get you undressed," Beth said as she took the dress off her new sister/brother.

After taking off his bra Beth unrolled his nylons and then slid off his panties and said, "so that's how you do it?" as she looked at his taped cock.

"Yeah is is," he said as he undid the tape allowing his tiny cock to spring out.

"Oh my that's so cute, can I?" Beth said reaching to touch her little brothers little cock.

Chuck never had anyone touch it but himself was amazed at his sister's soft hand holding him as his cock began to slowly harden growing as if it had a mind of it's own.

"Ok enough of that, don't want you to cum on my dress," Beth said releasing her hand.

Beth undressed and led Chuck to the bathroom, filling the tub she said, "Ok come here."

Pulling an electric grooming razor out she knelt down and removed the long hairs from Chuck's legs. Once done with that she asked him, "do you want to remove your pubic hair, I can trim and then wax you?"

"Will it hurt?" Chuck said.

"Hell yes, if you want I can just trim it really close then shave it," she said.

"I don't know let's not do that today," Chuck answered.

"Ok get in the tub and soak a bit then we'll finish shaving your legs," Beth told him.

After soaking Beth told him to sit on the toilet then got a fresh razor blade and put it in her pink razor, then lathering him with her shaving cream began to slowly remove all the hair from his legs. After she finished and wiped his legs off she oiled his skin lightly and admired how soft his legs were.

Both went to bed, Chuck couldn't get over how amazing his new hairless legs felt so much so his cock required a bit of attention and he fell asleep on top of the covers his stomach covered with cum.

"Oh I can't wait for tomorrow," he thought as he began to drift off.