It seemed to Ken that time had slowed down to a snails pace as he watched the events unfold before him. The door to his sister's bedroom seemed to take forever to open and for Connie to step inside. Connie's head was down as she placed something in her purse before it rose up. That act also seemed to take forever as did her eyes growing wide as she took in the scene in front of her.

Ken could blame no one but himself as had been pushing his luck as of late, but never imagined that he would get caught. But caught he was and there was no way he would be able to talk his way out of this mess. It took Connie's brain a second or two to process the scene before her as her mouth hung open in shock and surprise.

For standing there in the middle of her room was her brother dressed and made up like a girl, a very attractive girl. He was wearing one of her shortest and tightest mini dresses, black pantyhose and a pair of her knee high boots. A long brunette wig adorned his head and fell to his shoulders framing his pretty face.

Connie found it hard to believe that this hottie was her brother as his makeup was perfect  From the mascara and blush to the eyeshadow and the false eyelashes, everything was perfect. Connie felt of twinge of jealousy as she didn't think she look that good.

Now Ken braced himself for whatever torrent of curse words and screaming that his sister would issue but nothing happened. She just stood there and stared. Finally a faint smile came to her face as she hung her purse on the hook by the door and then shut and locked it behind her.

She approached him and slowly circled him like a general inspecting his troops. Connie could detect the trace of a thong under the tight dress he was wearing and that told her that he wasn't wearing pantyhose. He had donned a pair of her thigh nigh nylons and his legs looked perfect under the sheer black film.

"Not bad," she said to herself.

Ken stood there with his heart beating so hard in his chest he thought he was having a heart attack. With each passing second of Connie's scrutiny he also feared that she would let loose with a scream of anger. He found himself silently cursing that day so many months ago when he gave into his urge to try on one of Connie's bras.  

He had been doing his laundry in the basement when he found it in the clean clothes basket ready to be taken upstairs. It was a royal blue silk one that was trimmed with black lace. It was cool to the touch and his whole body tingled as he ran his fingers over the cups.

A second later he gave into his urge and tore off his t-shirt and fastened the bra around his chest. The moment that the cool material made contact with his warm skin his teenage cock began to thicken. He ran his fingers over the empty cups again and wished for a moment that he had breasts to fill them.

Ken then noticed a matching pair of bikini panties also in the basket. Without hesitation he lost his jeans and briefs and began to slowly draw her panties up his legs. By the time they reached his balls his cock was harder than it had ever been and the head was glistening with pre-cum.

He continued to pull her panties on until they covered his raging hard on and cradled his butt. The sight of his erection pressing against the nylon of the panties set his whole body tingling. He lowered the panties until his hard cock sprang over the waist band of its nylon prison. He then commenced to jack off while running his free hand over the cups of the pretty bra.

When he felt ready to shoot he grabbed a bra from the dirty clothes basket and let loose in one of the cups. The intense orgasm made his knees weak and he collapsed on the floor. He removed the items he borrowed and placed them in the dirty clothes basket hoping that Connie would not remember that they had already been washed.

He then took the bra that held his semen and shoved it to the bottom of that basket praying that it would dry before it was discovered. He then redressed in his regular clothes and headed upstairs as he needed to think about what had just happened.

'What is wrong with you? Are you some kind of sick twisted pervert?' he asked himself.

Now his childhood and early teen years were quite normal and he did all the things that young men do. Baseball, biking and checking out the pretty girls that watched them play were the rules of the day. He had even stolen a kiss and a feel job from some of those teen hotties.  All that changed the day he burst into the partially open door of Connie's room to ask her something.

That's when he saw his sister standing in the center of her room in nothing but her underwear. Now she screamed at him to get out but he seemed frozen in place. So she placed her arms behind her back and allowed him to get a good look before she screamed again and brought their parents running.

"Connie is no longer a little girl, she is a young lady. Young ladies need privacy when they are in their rooms. Next time you knock before entering," his dad told him when they were alone.

"So, did you get a good look? Did you like what you saw?" she asked in a quiet teasing voice after he had apologized to her.

Ken could only blush in response before he headed to his room. That evening the image of Connie standing there in her shimmering lingerie ran through his mind and got his cock hard. Although his sister was very attractive with a killer figure, it wasn't her body he was thinking about as he jacked his teenage cock. He was wondering what it would feel like to wear such pretty and silky clothing.

It was a week after that incident that he gave into the urge to wear Connie's lingerie. Once upstairs he tried to convince himself that was only a one time thing. He then commenced to masturbate as he recalled how great Connie's lingerie felt against his skin.

However the next day he when he returned to the basement to finish up his laundry he was once again overcome with the desire to try on Connie's lingerie. He recovered the same bra and panties he wore yesterday as the basket had remained unmoved. 

It was almost a repeat of the day before. As he donned her silky undergarments, the feeling got him hard. This time he stuffed the empty bra cups with rolled up socks and was pleased at the sight and feeling as he ran his fingers over the fake breasts. Now instead of lowering his panties to allow his cock to escape he grabbed his hard cock through the thin silky material.

He commeneced to jack off. The feeling of the cool nylon against his hot throbbing member increased his pleasure. As his orgasm approached he reached for the second bra and once again lost his load in one of the cups and his body shook with pleasure.

He continued to do his laundry while still clad in the stolen lingerie. Ken checked out his butt in the mirror of an old dresser in the basement and liked what he saw. He later ran a delicate load to clean the lingerie he had used to avert suspicion. Later in his room Ken finally admitted to himself that he liked dressing in bra and panties and wanted to do it again, but he had to be careful. He couldn't rely on there always being some of her lingerie in the laundry so a plan was needed.

He stole into Connie's room one evening while she and the family were out. He had faked a illness in order to remain behind so he could explore her room and learn where all her prettiest clothing were stored.

Her closet was packed with miniskirts, dresses and blouses. Dozens of high heels were stored in the hanging shoe tree. He also discovered that one large dresser held her most intimate apperal. She had more bra, panties. slips and nighies than he ever imagined. He was pretty sure that with such a large collection that she would not miss a few items.

That was how it started. Soon the bra and panties were not enough and Ken borrowed one of her full slips to wear over his borrowed lingerie. Soon he gave up the slip and tried on a short tight skirt and a silky blouse. He shivered with delight the first time he covered the bra he borrowed with one her silky blouses.

He was glad that he and his sister were the same height and weight because her clothing fit him perfectly. As the weeks marched on, pantyhose and heels came next. Ken was surprised at how quickly he mastered walking and standing in her highest heels, but it still wasn't enough. While his body looked and felt great when he donned her clothing, he still looked like a boy in girls clothing.

An afternoon of web searching provided him with sites that gave instructions of how to wear makeup. He even ordered some makeup online so he didn't have to bother Connie's. As he was always the first one home no one was the wiser and he hid them well in his room.

Early mornings on the weekends would be his time to practice as his family was still asleep. When spring vacation arrived he now had all day to work on his makeup skills. As the days passed his skill at applying makeup became better. A wig was ordered and Ken could not wait until he could wear them all at the same time.

The opportunity presented itself when an invitation to a wedding of a distant relative arrived a month later and his parents gave them the option of attending of staying home.

Ken opted to stay home as did Connie. Connie announced that she was going out with her friends and Ken informed his parents that he would stay in and watch a movie. Ken waited a half an hour before he started to transform himself. He tried to ignore these urges but they were too strong. 

He tried to tell himself that this discovery would spell his doom, he didn't care. Ken didn't believe that he should have been born a female and was never attracted to another male.

"I just like dressing up," he told himself as he applied his makeup. 

He put the finishing touches on his makeup and then headed to Connie's room to dress. He had just finished dressing when Connie walked in on him. She finished her inspection and stood in front of him. Even this close there was no hint of her brother in the girl before her.

Connie could see that he was nervous so she gave him a smile and he began to relax.