Ken sat there with his heart pounding in his chest. His sexy sister had just admitted that she wanted him to ball her.  Dressed in a sexy black nightie complete with thigh high nylons she was a picture of pure sexy. Her eyes were lit with lust that made her look even more desirable.

Connie had discovered his cross dressing secret and had promised to keep it to herself, providing he agreed to her demands. One demand was doing her laundry. He was to wash and dry her clothing and put them away. Ken had no trouble with that as he had been washing her sexy bras and panties since he first gave into his urge to wear them. Her second request was that they hang out together when their parents were out once he was made up and dressed. 

So on the first night that their parents headed out he reported to her room wearing her violet baby doll nightie and in his full female make up. Everything was fine until he admitted that he wanted to fuck his newest girlfriend in the ass.

Connie had no response. Then using the premise of posing for some bondage photos Ken allowed himself to be bound and gagged on her bed. However once the pictures were taken Connie did not release him. Unseen by him she donned a harness holding a small dildo and fucked him in the ass.

She told Ken to consider it a lesson.

"Not all girls like anal. Maybe next time you'll remember this and think twice before you take try to take some hotties butt cherry," she stated.

Connie then had him freshen up and change nighties before he was to return to her room. When he did return he discovered that she had doffed her leather attire and had donned a sexy nightie complete with thigh high nylons. He sat on the bed next to her and she admitted how hot for him she was.

To prove this she placed his hand on the silk crotch of her panties and Ken discovered that she was very wet. Then without warning she placed her full red lips on his and began kissing him. Just as the day she had caught him in her room dressed in her clothes time began to crawl by at a snails pace.

As he felt and tasted her warm sweet tongue enter his mouth a hundred conflicting emotions ran through his mind. 

"If this is wrong why am I so excited?" he asked himself.

Now Ken was well versed in kissing and this was the best kiss he had ever received. That still didn't stop the nagging conflict within his mind.

"This is your sister," he told himself as she wrapped her slender arms around him.

Now between his silky clothing and hers and her long lingering kiss he had gotten very hard, but still had not returned her kisses. 

"What's wrong?" she asked ending the kiss

"I can't," he responded.

"Why?" she pleaded.

"You're my sister," he answered.

Connie stared at her brother for a moment as the fire of desire grew stronger inside her.

"OK, relax. Let's just relax and talk about it," she suggested.

Ken agreed and stretched out his back and Connie was on her side facing him. A second later Connie sat on his chest and tied his wrists with the bonds she had used earlier. Ken started to protest but was silenced when she managed to place the ball gag in his mouth.

She then slid herself down to his thighs very slowly. The feeling of her nylon covered legs and butt against the bare flesh of his legs turned him on even more. He tugged at his bonds but there was no give. His protests were nothing more than unintelligible sounds due to the gag. Sitting astride him she took more photos and then showed them to Ken.

"See how hot you look," Connie said as she showed the frozen images to him on her smart phone.

Ken stopped struggling and looked. He had to admit that he looked one hundred percent female.

Connie then lifted his nightie hem exposing the see through panties underneath. The tiny nylon garment was struggling to keep Ken's cock contained. She gently tugged the waistband down allowing his hard cock sprang free. She admired it for a second and then leaned over to her nightstand and fished around in the drawer for a moment. Connie then produce a condom that expertly slid it over his rigid shaft.

Ken eventually quit struggling and attempting to protest and watched these events with wide open eyes. Once in place Connie removed her wet panties and positioned herself above his latex covered shaft. Ken noted that she was totally shaved and that was a turn on to him.

She placed the head of his cock against her opening and then slammed herself down on it. The sensation caused both of them to moan loudly. Several time she rose up and slammed herself down hard on his cock. She then leaned into Ken's face.

"If I remove the gag are you going to complain?" she in a breathy whisper.

Ken shook his head and the gag was removed. Connie began to cover his face with kisses before moving to his lips.

"Am I hot enough?" she asked.

"Oh yes. Am I big enough for you?" he asked.

"It's the perfect size for me," she responded before attaching her lips to his.

This time as her tongue entered his mouth he allowed his tongue explored hers. Connie ended the kiss and sat straight up where she commenced to run her hands over her breasts.

"See how hard you made my nipples?" she stated,

She then leaned her torso forward until they were inches from his lips.

"Kiss them and lick them," she begged.

Ken lips planted kisses all over them in between allowing his tongue to flick at her erect nipples. That act caused Connie to moan louder and Ken could feel her internal heat increase .Between the kissing,licking and her thrusting Connie was close to her orgasm.

"Please hold out," Connie begged.

It was with an effort that Ken was able to hold his release. Even when he felt Connie's internal muscles grip his cock and heard her long sustained moan he did not let loose. A minute or two afterwards she climbed off of Ken's still hard cock and tore off her nightie.

She removed his condom and placed his rigid shaft between her full and warm breasts. Connie pushed her breasts together and began to slowly move her upper torso up and down. The sight of his cock between his sister's lush breasts and the feeling of their silky skin against him was too much.

"Connie, I'm going to cum," he managed to inform her and a second later he emptied his load between her soft breasts.

She untied him and laid next to him. He watched his semen dribble down Connie's breasts to her still erect nipples as he listened to her breathing become normal.

"That was fantastic," she said as she wrapped her arms around him.

Ken took Connie in his arms and pulled her closer and they gently kissed for the longest time.

"I think I need to shower and freshen my make up," he commented.

OK," she commented and got off the bed.

Ken was heading out the door when his sister stopped him and handed him a fresh bra, panties, garter belt and nylons.

"After your shower and make up retouch you need to come back here," She instructed.

What's up?" he asked.

"You remember me telling you that not all girls like anal?" she asked.

"How could I forget," he responded.

"Well I'm not one of those girls," she responded with a shy smile.

It was the quickest shower of his life and he set a new speed record in redoing his makeup. Any fear he had about what he had done and would do vanished. In his sister he had found the ultimate partner.  What other girl would encourage his cross dressing? What other lady would want to make love to him while he was dressed as a female?

He redressed and took a moment to admire himself in his dresser mirror. He was 100 per cent passible and sexy. Ken headed to Connie's room and knocked on the door. He was told to enter.

Connie was on her hands and elbows on her bed. She was wearing only a black garter belt and nylons and her perfect ass was high in the air. She looked over her shoulder and smiled.

"It's all yours, pretty girl," she said softly.

Ken got in his knees behind her and starting with her long lock he ran his hands all over her body. He stopped only long enough to reach for the sex lube and the condoms.

"No, I want you to go bareback," she said softly.

Ken could not believe his ears and left the condoms untouched. He grabbed the sex lube and applied a generous portion of the slippery liquid to her back door and his throbbing cock.  He placed one hand on her hip and used the other to position his cock at the entrance to her back door.

Connie's moan as he slowly pushed himself inside her was one of the sexiest sound he had ever heard. Later as the held each other he asked if she would do him in the same fashion and she agreed. It was the beginning of one of the greatest Summers of his life.