Little Black Dress

Timmy was always jealous of his older sister. She was the favourite in the family and was always the centre of attention in every scenario. She was so beautiful, and people just loved her - Timmy always wanted to feel that love. He had recently turned 18 and puberty hadn't been kind to him. While all the other boys suddenly got taller and more muscular with deep voices, Timmy just stayed much the same and maxed out at 5'6". His thin frame was feminine and his refusal to cut his long blonde hair was doing him no favours in that department either. One day when he was home alone an urge took him and he found himself entering his sister's room. If he could emulate his sister, perhaps his popularity would skyrocket.

He walked to the wardrobe and opened the double doors and all of his sister's clothes unveiled themselves. Hanging on the left were dozens of dresses and skirts of every style. On the right were cute tops and shorts. On the bottom rack were all manner of high heels, ballet flats and sandals. As he opened the drawers Timmy saw all of the matching lingerie sets, sports bras, leggings and bikinis. He grabbed a matching set of black lace panties and bra. He slid the panties up his smooth, hairless legs and tucked in his insignificant "manhood". The move was effective, and no bulge was visible when he looked down. He then clasped the bra behind his back first try and found some chicken fillets that he used to give the illusion of breasts and cleavage. Then came the dress. It was a body conforming little black dress and it hugged his feminine figure perfectly. He found a pair of four-inch stiletto heels and slipped his feet into them, and they fit perfectly.

He then applied a light coating of make-up, including mascara, black eyeliner, and kiss-me-now red lipstick. He carefully brushed out his long blonde hair for the first time in months and found it tough going through the knots, but several minutes later and he was done. Content with himself, Timmy closed the wardrobe to see his reflection in the mirror on the doors. 'Mission accomplished,' he thought to himself. This makeover succeeded - not to make him a spitting image of his sister but to make him look like her sister. Something stirred inside him and he felt more like himself as he ever did before.

His self-admiration session was cut short when the floorboards behind him suddenly creaked. 'It's the middle of the day,' he thought to himself, 'who could it possibly be?' Heart racing, Timmy turned around to see his sister's boyfriend, Steve, standing in the doorway with a huge smirk on his face. Steve was athletically built, standing 6'2" tall with muscular arms and legs and had short brown hair. Their eyes met and in an instant Steve had crossed the distance between them and taken Timmy into his arms.

"I know that's you, Timmy. Or should I say, Tammy?" Steve whispered into Timmy's ear.

Before he could utter a reply, Steve planted a heavy kiss on Timmy's (Tammy's) lips. Tammy quickly lost himself and relaxed into the kiss. Some minutes later they came up for air, and the rookie in his new high heels lost his balance and stumbled. Without skipping a beat, Steve caught him, carried him over to the bed, and laid him down on his back.

Tammy was lying there, still trying to collect his brain from the void and piece together the situation he suddenly found himself in. He was certainly enjoying himself, but this had to be wrong on some level didn't it? From Steve's perspective, the dumb-founded, mouth-agape look was an unspoken invitation and he unzipped his pants, placed his knees on either side of Tammy's shoulders and put the head of his cock in Tammy's mouth. The invasion of his mouth brought Tammy, wide-eyed, out of his stupor and into the current situation. He initially wanted to resist but the smell and taste of his cock proved too hard an obstacle to overcome. He very quickly grabbed Steve's legs and found himself lifting his head to meet Steve's 8-inch cock with every thrust. Tammy relaxed his throat and the cock slid further and further into his mouth. On the second last thrust, Tammy felt the tickling of pubic hair on his nose, and balls on his chin; then on the last thrust he stuck out his tongue to lick the balls on their arrival. Tammy could feel the sudden twitch of Steve's cock and knew he was close.

Steve felt this but was not done yet. He pulled his cock out of Tammy's mouth and then turned him onto his stomach, lifted his ass in the air and arched his back. He continued to then lift the dress up and over Tammy's ass, then pulled the panties to the side. He leaned into the Tammy's ear and again whispered, "I'm gonna fuck you like I've never fucked your sister." Then instantly plunged his cock into Tammy's ass. Tammy screamed in pain, but the pain quickly turned to pleasure as Steve's cock reached his g-spot on the first thrust. For the first time, Tammy felt his cock straining against his panties for the first time tonight but was not able to let it out. Moans of ecstasy were leaving Tammy's mouth with every thrust and got louder and faster and Steve fucked his ass harder and faster. Steve's balls slapped Tammy's ass over and over again. Then, Tammy again felt the unmistakeable twitch of Steve's cock but this time Steve let himself cum. Spurt after spurt, 5, 6, 7, then 8 times until the cum started leaking out of Tammy's ass. Tammy came with Steve and drenched his panties.

Another creak in the floorboards and both Steve and Tammy looked up instantaneously. Steve was still balls deep in Tammy's ass at the time. This time standing in the doorway was Tammy's sister with her hand in her panties and her juices flowing down her leg. She had clearly been there a while but did not wish to make her presence known. She walked over to the bed and sat legs spread in front of Tammy.

"You will clean me up, sissy, or you will never get Steve's or any other man's cock every again."

And so, Tammy quickly went to work lapping up his sister's juices from her body. When finished he collapsed in exhaustion...

When he awoke, Tammy found himself now with a clean pair of panties and wearing a black negligee. He was sandwiched between a sleeping Steve and his sister, feeling Steve's semi-erect cock pressing against his ass, and a bulge in his sister's panties pressing against his stomach. Tammy didn't know what this would mean but quickly tried to fall back to sleep eager to bring this new adventure around quickly.