Ken had been caught by his sister in her room wearing her clothing. There was none of the screaming or threats of exposure that Ken feared Connie would issue. She instead suggested that they talk and talk they did. Ken admitted everything to her. From the jacking off while wearing her lingerie and then cumming in one of her bras.

Ken did not hold anything back. He confessed about coming into her room to learn where all her sexiest clothing was kept and then borrowing some items.

Connie said nothing as he talked. She even encouraged him to continue when he was hesitant to go on. When he finished she gave him a kiss on the cheek and told him it was all right.

"Now there will be some conditions if you wish to continue," she informed him.

"Continue and conditions?" he asked.

"Yes.I don't see you stopping just because I discovered your secret and it would mean trouble if my clothing and lingerie were found in your room. So dressing in here is the only solution," Connie stated.

"That's true," Ken stated." So what are your conditions?"

"You take over doing all my laundry and not just my lingerie," Connie stated.

"That's it? That's not a problem," Ken responded.

"That includes putting them away like Mom did when we were younger. I imagine you know where everything goes. However if Mom and Dad are home just put the basket on the bed," his sister continued.

"Also not a problem," Ken answered.

"No touching my makeup," she added.

" I have my own stash. Anything else?" he asked her.

"Yes. I'd like us to hang out some evening when our parents head out to one of their social events," Connie added.

"Hang out?" Ken questioned.

"Yes. We dress in our sexy nighties and talk about what is on our minds," Connie stated.

"Deal," was all Ken said.

The fear Ken felt vanished. As soon as he relaxed his body responded to being dressed Connie's silky clothing and he got hard.

"I think you better go to your room and take care of that," Connie stated pointing at the bulge under his dress.

Ken headed to his room and locked the door behind him. He took a seat on his bed and then swung his legs over. Once on his back and propped up against some pillows he took in the sight of his body clad in female attire and he like what he saw. He allowed his fingertips to run up his nylon covered legs headed toward his hemline. The sensation sent a shudder through his body and increased the hardness of his cock.

His hands slipped under the hem as it continued to trace his silky covered legs. His fingers encountered the lace tops of the stockings and then the warm flesh of his upper thighs before they finally reached his target. It was the silky thong that was struggling to hold his hard cock inside.

He allowed his fingers to trace the outline of his erection before his hand circled it and he began to gently masturbate. He looked toward the mirror on his dresser across the room and saw pretty girl face in the reflection. He wished he had a large mirror so he could see his whole body.

Finally he felt his heart rate and breathing increase and a small moan of ecstasy escaped his lips as he lost his load in his thong panties.When his breathing returned to normal he carefully slid off his cum filled panties before undressing. He then removed his makeup and showered. Once dressed in his lounging clothes he carried the borrowed lingerie to the basement.

He encountered Connie in the kitchen taking a Coke from the fridge as he headed back upstairs.

"Like night and day," she stated when she saw him as his male self again.

He took a Coke for himself and they took a seat at the kitchen table. She asked more questions about his transformation that he willingly answered.

"You will need to keep a few items in your room for those late night urges," she informed him.

"Fine. You choose the items," he responded.

Later that evening while their parents were in living room Connie presented him with a sexy nightie and matching panties.The days passed without incident and Ken did her laundry as promised without protest. Connie was pleased with the service. School finally ended and that signaled the start of the Summer vacation.

It also signaled the start of numerous fund rasing events that their parents would chair and attend. It was the first Friday in June that their parents announced that they would be heading out on Friday after work and would not return until Sunday. They issued the standard warning of no parties or overnight guests and both brother and sister responded that they understood.

It was after breakfast and their parents had left the kitchen that Connie questioned her brother.

"Did you wash my violet nightie?" she asked.

"It's hanging to dry," Ken answered.

"Good. Wear in tonight and meet me in my room at eight," she added.

The minute their parents left Ken dug out his makeup and began his transformation. At eight he donned the sexy violet nightie and headed to Connie's room and knocked on the door. She invited him to come in and he could not believe the sight before his eyes.

Connie was sitting on her bed clad in one of the sexiest ensembles he had ever seen. A black leather bra was paired with black panties of the same material. A matching garter held up a pair of black seamed nylons. A pair of black silk gloves that extended up her arms to her biceps completed the outfit.

Ken crossed the room and sat next to her. Connie once again could not believe that this sexy girl was her brother. They talked about their first sexual experience and the strides they made since then.

"I hear your hanging out Coleen Chilton," Connie stated.

"Yeah I guess so," Ken responded.

"So how far have you got?" she asked

"Not too far. Just some kissing and touching," Ken responded.

"Sounds like you're making progress," Connie giggled.

"I hope so. I really want to give it to her in the butt," Ken answered.

"In the butt?" his sister questioned.

"Yeah, I hear she likes it," her bother responded.

Connie said nothing and was aware of Ken checking out her outfit.

"You like?" she asked smoothing out one of her long gloves.

"I love it. Where did you get it?" he asked.

"I was seeing an older guy that was really into bondage. He brought this for me and had me wear it all the time," Connie answered.

"Maybe I can borrow it?" Ken asked.

"That privledged has to be earned," she responded.

"Anything," Ken responded as he visualized himself clad in that leather outfit.

"Let's try something different. Get on your hand and knees and we'll take some bondage pictures and see how well you photograph," Connie stated.

Ken did as asked and knelt on Connie's bed. She tied his wrists to the top of the bed posts using an old pair of nylons and then produced a ball gag. He was a little hesitant when she showed it to him.

"Relax, it's mine," she told him.

He placed the gag in his mouth and Connie secured it. She then took a half a dozen pictures of him bound and gagged and the results were great. There was no trace of a young male in the images, she saw only a very pretty girl.

Ken tugged at his bonds and tried to tell Connie to release him. However the gag prevented him from speaking.

Suddenly Connie appeared at the side of the bed and Ken's eyes went wide when he saw her. Connie was sporting a small cock from a harness she had donned. He tugged harder at his bonds and made noises but Connie just smiled.

"Not yet pretty girl. There is one task left," she crooned in a soft and silky voice.

She then moved behind him and reached under his nightie and slowly pulled his panties down.

"So you want to fuck pretty little Coleen in the ass? Let's see how you like it," she crooned again.

Ken felt something warm and wet being applied to his anus and panic shot through his being.

"If you struggle it will hurt more," Connie whispered in his ear.

Ken felt the tip pressing against the entrance to his little pucker and a second later he felt it entering him. Connie did not ram it in but inserted it very slowly. She kept a constant reminder for Ken to relax as she pushed the fake cock in him. A hundred feelings and emotions coursed through Ken's mind as it happened.

A second later he felt his sister's body heat against his exposed butt and her small hands on his waist. That told him that she was totally inserted.

"I just took your cherry. Now let's see if I can make you cum," Connie stated as she began gently pulling and pushing the cock in and out of him.

Between the sexy clothes and the exotic perfume Ken had gotten hard and he didn't lose it. Even when Connie pushed the phony cock inside him he remained hard as a rock. A second later Connie removed one of her hands from his waist and allowed it to circle his own cock.

"You like that?" she asked as she began to gently masturbate him.

Ken managed a small moan through his nose at this new feeling as he rode the waves of euphoria. Less than a minute he lost his load all over the bedspread. Connie removed the intruder from his butt before she untied and ungagged him. He collapsed on his side with tears streaming down his face.

Connie moved on the bed and took a position next to him.

"Why?" was all he could ask.

"Hurts doesn't it?" she asked.

"Yes," he answered.

"Consider it a lesson. No matter what you hear not all girls like anal. Maybe you'll remember this before you try to push your hard cock into some girls virgin backdoor," she stated as she brushed a lock of wig hair out of his eyes.

Ken had no answer and that allowed Connie to continue.

"No go and retouch your makeup and select a fresh nightie from my collection. Come back here as soon as your ready," she stated.

Ken moved gingerly as there was a slight burning pain in his butt. He selected a black nightie from Connie's collection and headed to his room and retouched his makeup. Sitting was a little uncomfortable but he managed by shifting from one cheek to the other.

Less then a half an hour later he knocked on Connie's door again and was told to enter. Connie had shed her leather and was also  dressed in black nightie complete with thigh high nylons. He sat on the bed next to her and she showed him the video of her fucking him that she had recorded and sent to her laptop.

Ken could not believe that it was him.The girl he had become looked even sexier than Connie.

"Do you have any idea how hot this get me?" Connie stated with her eyes fixed on him.

"Really?" he asked.

Connie responded by taking one of his hands and placing it on the crotch of her panties.He felt that it was soaking wet.

"So you game for something really forbidden?" she asked.

"LIke what?" he responded without looking up from the video.

Connie leaned into him and placed her moist lips on his and then wrapped her slender arms around him. She held him tight as her tongue entered her mouth.

Ken could not believe that this was happening and gently pushed her back.

"What do you want?" he asked trying to ignore his hard cock.

"I thought that it was obvious.I want you to ball me. I have not had a good fucking in quite sometime," she answered.

"But I'm your brother," he responded.

"You don't think I'm hot enough?" she asked with her eyes lit with passion.

"You're very hot," he answered.

"And you in that nightie are also hot. I always wondered what it would be like to make love to another girl," she responded.

Ken just sat there and pondered what to do next..

To be continued....