Sam walked into the house, checking from room to room to make sure no one was home. Today was the day. Today he would finally act out on his fantasies. The idea of cross dressing turned him on. To be 'sexy'. He was only sexually interested in women, but the idea of being sexy like a woman turned him on.
After he was sure no one was home, he went up to the bathroom with his goody bag. In it were all the things he needed. Some things were easier to get, body lotion, bandages, razors and shaving cream, and body grooming materials. Those you could just act like you were really prissy about your appearance to buy. Other things were more difficult. To be specific, clothing. It's hard to buy girls clothing as a guy. He blushed, placing the items on the counter, mumbling about how they were, 'for his girlfriend'.
He walked into his bathroom and locked the door. No one was supposed to be home for hours. Taking a deep breath he wrapped his arms around his body, holding himself. He ran his hands down his chest to the bottom of his shirt, lifting it over his head, arching his back ever so slightly. He tossed the shirt to the floor and felt his skin. So smooth and warm, his nipples erect. He ran his fingers over them, gently playing with them.
Sliding his hands further down, he undid his belt and slid his pants and boxers to the ground. He was completely naked now, and was shivering from excitement. He ran his hands over his legs. He had a petite frame. His body was small, arms thinner than most men, his legs defined. His stomach was smooth as was his chest.
Reaching into his bag he removed the razor and shaving cream. He sprayed a good amount into his hands and, putting a leg up on the toilet, lathered it up. He slid the razor up his legs carefully, shaving the hair off of them to reveal smooth, sensual legs. When the one was done, he moved to the other. Next his lathered up his chest, shaving off the few hairs that were there. Finally the big one. He had never shaved his genitals before. This was a big step for him. He closed his eyes and lathered up the sensitive area, slowly shaving the hair off, not wanting to get razor burn. He looked down at the finish product.
His body was now bare. He ran his hands all over himself, feeling the smooth unblemished skin. Opening the door to the shower he stepped in and turned the water on. It was steaming hot. He took out the body wash, a sort of floral smell, and washed his smooth body from top to bottom. He took the hair wash and closed his eyes, rubbing it in gently, massaging his skull. Then the conditioner.
He stepped out of the shower feeling refreshed. Water dripped off of his body onto the floor. He grabbed a towel and dried himself. He squeezed lotion onto his hands in a little ball and coated his body in it. He was so smooth, like a baby. He smiled at himself in the mirror, feeling sexy already. His body was slightly red after the hot shower.
He retrieved all of his stuff and walked naked over to his room where the rest of the change would happen. There he closed the door, making sure it was locked tight. He lit candles, turning off the harsh light, and sealed the curtains on the windows to make sure no one could see him but him.
He grabbed his favorite Jazz album and put it in the record player. The scene was perfect. There he was, beautiful lighting, great music, and a tight naked body.
He reached into his bag and grabbed a little pouch. This sort of covered up his penis. There was a lot of pressure, but it was pleasant, not painful. He slid on a pair of black lacy panties, arching his back and looking over his shoulder at himself in the mirror. He had an amazing ass. Perfectly proportionate with his body. Not to big, but not flat like most guys. He stuck his ass out, which worked with the way he had arched his back. It was an image no man could resist.
He grabbed the skin colored bandage out of his bag and covered his chest with it firmly. Every layer he wrapped it he would add a bit of extra bandage on the front. This raised out his chest, without raising his back out any. On top of all this, he put on his black lacy bra. Now he was beginning to look very feminine.
His hair was only the length of a pixie cut, so he did it like most women in magazines did it. The results looked nice with his body.
He grabbed a pair of solid black tights out of his bag, pulling them up his smoothly shaven legs. They felt amazing on him. How could girls wear these and not be turned on all the time? His erection swelled up to it's full size, but the covering just compressed against it, refusing to raise out against his black panties, that were smooth all around. This turned him on even more. His legs looked amazing. They were small and girl like already, but now that they were shaved and dressed up they looked even better. His feet were the perfect size for a girl as well, about a size 6 in women's shoes.
He grabbed the gray skirt from his bag, a sort of school girl skirt that rode up just above his knees. It went well with the tights and his almost bare upper body. Right there he wanted to take a step back and have sex with himself, but he couldn't, the only draw back to his fantasy.
The final piece to this outfit, a white dress shirt. He pulled it onto his shoulders, pausing a minute to look at himself in the mirror before buttoning it up. The skirt went up just below his naval, the look of this was so sensual, his little belly button on his tight body was just a slight indent in the sea of smooth skin. He buttoned all of the buttons one by one, working his way up, leaving the top most buttons by his collar bone undone, and tucking the shirt into the skirt. He rolled the sleeves up below his elbows, exposing just enough skin to make you want more.
He inspected himself in the mirror, turning around sensually, moving his hips as much as he could. He wanted to work on his walk and talk. He walked all over his room, swaying his hips subtly moving his legs as best he could. The hardest part was moving his arms. He was so used to tucking his hands in his pockets, or balling them into fists as he walked.
Satisfied that he had the walk down he went to work on his face, using as little make up as possible. He glossed up his lips a little to make them look wet and plump. After this he took his glasses and put them on his face. The image was complete. He was 'sexy'. You wouldn't be able to tell him apart from any other girl out there.
Suddenly an idea came to him. He grabbed his camera and set it up to take pictures of him. He positioned it on his desk so it would take pictures every five seconds. He got on his knees on the floor, putting his hands between his thighs and looked up at the camera with a come hither look on his face. Then he bent over his bed and took a few pictures of his welcoming ass. Then he laid down and closed his eyes, raising his legs up and running his hands over his body. After it was over he looked through the pictures, deleting the ones he didn't want.
He walked down the stairs to get some juice from the fridge. This was tiring work. Big mistake.
He got into the kitchen and bent down to get some juice and someone came up behind him and in a firm tone said, "what the hell are you doing in my house!"
He whipped around and saw his sister there looking furious. He opened his lips to speak but she kept yelling.
"What do you think you're doing here? If you're one of my little brothers sluts you better keep your hands off and go home."
"You you you what?"
Then she looked him up and down, and with a curious look on her face asked, "little brother?"
With this Sam ran up the stairs as fast as his little legs could take him. His sister ran just as fast, and over took him, whipping him around and grabbing his wrists, slamming his body against the wall.
"What the hell are you doing you little perv? I didn't know you were into this stuff too!"
"Wait.... what do you mean too?"
"You have to keep this quiet. I mean it won't come back on me like it would you if you told anyone so I know you will, but I dress up like a guy sometimes. I mean not like that Tom boy that I already am, but I really dress up like one. It's super convincing."
"Why are you telling me this," he said with a quivering voice. He had the girl voice down perfectly.
"Because, you're going to wait downstairs in those clothes while I get dressed, and then I'm taking you out with me."
"NO!" He tried to pull away but she held him firm.
"If you don't I'll tell all your friends just what you do while no one's watching."
He gave into her and walked down the stairs miserable, waiting on the couch.
After 20 minutes down walked his sister, only she didn't look like his sister at all. He shoulders were full, her hips masculine, the way she walked all hinted that she was a 'he'.
"Well what do you think?"
The voice that came out of his sister's body was not even slightly girly. She was absolutely perfect.
"I think you look so... handsome."
"Alright, we're going to Brian's party. You know Brian, from your class?"
"No! They'll recognize me! If anyone finds out..."
"Trust me, no one will find out. No one even knows I'm a girl. Even the girls I've slept with don't know," she winked.
They headed to the party and knocked on the door. Sam was fidgeting with his dress And looked around nervously.
"Relax, will ya?"
He took a deep breath and they walked in. All the kids from his year were dancing around to the music. Boys turned there heads to look at him as he walked into the house nervously. No one recognized him yet. No one was laughing. With that he gained a little confidence and started to sway his hips slightly.
His sister wandered off, grabbing the nearest girl and danced with her. It was so surreal. As he walked he felt something odd. A quick pat to his ass followed by a, "hey baby, what's your name?"
He hadn't thought of that yet,
"Uh, Lily," he said as he turned around. Then his heart skipped a beat. It was Brian.
"The names Brian," said the boy, "but you can call me hot stuff."
Sam thought, 'how the hell does THIS guy get girls. He's such a douche bag it's so unreal.'
"Well it's nice to meet you Brian but," before he could finish his sentence Brian leaned in and kissed her. It was ruff, and gross. His breath tasted like he hadn't brushed in a few days, he pushed his tongue against his lips trying frantically to french.
Sam staggered back and just walked away as quick as he could, moving out to the dance floor. his heart was pounding against his chest. He had just kissed a guy! He moved through the dance floor and grabbed a drink, guzzling it down quickly to get the taste out of his mouth. He moved back on the dance floor and starting dancing as best he could.
It turned out he was really good at it, and soon most of the eyes were on him. Girls were getting jealous, and guys were getting a cheating look in their eyes. After a while of this he moved off of the dance floor and grabbed another drink. He started getting a little buzzed with that one, and took another and another until he was drunk.
His head was spinning when Brian grabbed him by his hand and lead him up the stairs. He fell back onto the bed giggling as Brian crawled on top of him, kissing him. He grabbed him and kissed back, too drunk to realize what he was doing. Suddenly the door burst open and someone pushed Brian off, grabbing his own hand and pulled him out of the room, down the stairs, and out of the party.
His sister dragged his drunken ass home and brought him upstairs to his room. She helped him get the girl clothing off so that their parents wouldn't see him like this, and threw the blankets over him.
The next morning he woke up without really remembering what happened. He wandered downstairs, feeling oddly uncomfortable in his male clothing. His sister had breakfast all laid out for them, their parents having already gone to work.
"What happened last night Terry?"
"Oh nothing, you just almost got your ass raped, that's all. Other than that no big deal."
"WHOA WHOA, what happened?!"
"Okay so it wasn't rape, but you got trashed last night and Brian got your upstairs, and almost under your dress."
"Okay. I am never going to go to a party like that again. Just as I was getting used to wearing those sexy clothes too..."
"Well... there is another option you know."
"Like what," he asked.
"Well... we could date each other. I mean it would let us both safely get our fantasies out of the way..."
Sam was speechless. He didn't really know how to respond. It was his sister, which made it kind of gross, but it did let him get all of his fantasies out of the way.
"Okay... but we just date like friends, okay? I mean no kissing, no fondling, nothing like that. Deal?"
"Deal," Terry said as they shook hands.
Their first date was to be that night. He was going to wear the same outfit, because he didn't really have anything else to wear at that point.
Three months later and they were still dating. They didn't kiss or anything, they just went out. They would hold hands in theaters and go to dinner together. He felt content doing this. The fantasies didn't go any further until one night when things changed forever.
Sam's sister walked him to his door after the date to say 'goodnight', a ritual that had done since it started. The would say goodnight at his door, go to their rooms and undress. After that they would act like nothing happened. Not this night though.
Sam leaned against his door frame and looked up into his sister's eyes.
"Goodnight handsome," he said, winking. Before he could turn around to go into his room his sister leaned in and kissed him full on the lips.
He staggered back, "what the hell are you doing?" He wasn't mad, just shocked.
"I can't just leave it at this. I know you want to go further too, and since you're my girlfriend it would be cheating if I went after another girl."
"But I'm not your girlfriend. I'm a boy, and I'm your brother!"
"Not when we're like this," and with that she kissed him again, pushing him back into his room, locking the door behind her.
"But, I," She kissed him again, shutting him up.
She pushed him back onto the bed and got on top of him, straddling his legs and pressing her crotch down to his. His covering concealed the massive erection he had at this point, but something was off. He could feel something hard pressed against him.
"What's that," he whispered in a dreamy voice.
"A special treat. It's a strap on, but it looks and feels like real flesh. What's better, my pubes cover up the parts that hold it on, and it reacts to how horny I am. I can actually feel it too. I can feel everything it feels, and when I cum it shoots out a solution that feels and tastes just like cum."
He groaned as he pushed his hips up against his sister's cock. It was so erotic to him.
An idea popped into his head and he flipped his sister over, kissing her neck lifting her shirt over her head exposing her flat chest and sexy abs. He kissed down to her pants and took the belt in between his teeth, undoing it.
"What do you think you're doing little girl," his sister asked sarcastically.
"I'm going to suck your cock, and swallow all of your cum." He said this very matter of factly.
His sister closed her eyes and rested against the pillow as her brother slowly slid her pants down to reveal an almost completely life like cock. Nervously he leaned forward and kissed it. It rose up to full six inches and sort of pulsated. It wasn't super long, but it was thick. He stared at it intensely, so afraid of the work he was about to do.
He leaned forward and took the cock in his mouth, sucking slowly on the head as his sister moaned in ecstasy. A strong hand reached behind his head and pushed it down deeper. Half of a hard warm cock was now in his mouth. He could feel it probing him, rubbing against the top and sides of his mouth and poking the back of it. It slid against his teeth ever so slightly as he sucked, and pressed his lips firmly against it. He moved his head up and pulled the cock up to the tip almost out of his mouth, breathed in gently, and plunged steadily down.
He fought his gag reflex and held the cock in his throat. His sister moaned audibly as he pulled up just an inch, and slammed back down on it. He held his breath a long time, pulling out only an inch and slamming down to the base of her cock, his mouth holding a vacuum over it. He kept his eyes shut tightly as he focused on nothing but pleasing the cock. He knew what his felt like. He knew how he liked it pleased, so it came naturally to him what to do. He used his tongue to work on the cock with his lips and cheeks. He hated having a hand used on him, so he left his on the bed.
He worked on it for what seemed like forever before he felt the familiar twitches that let him know she was about to cum. He slowed down to a crawl, using only his lips and tongue, sliding all the way to the top, and all the way down to the bottom. This was the final straw, wave after wave of hot cum shot into his mouth and into the back of his throat. He pulled back, wrapping his hand firmly, but not tightly against the top, and with his spit as lube, he rubbed his hand up and down, pumping more cum all over his face, and into his open mouth. His sister looked at him as he did this with a look on her face that said she wanted more.
He swallowed his first ever load of cum with little difficulty, taking his fingers and getting the rest off of his face. He looked into his sisters eyes and sucked the cum off of his fingers. This turned her on again. His other hand was still working on the cock that stayed hard.
"How can you stay hard after a thing like that?"
"Girls can stay turned on even after they cum. I can go again and again, and this thing has three loads in it before it's spent."
"Really?.... I ... I want you to fuck me." He looked down and blushed.
"Are you serious? I mean are you sure you're ready for this?"
"Yeah... if anyone's going to take my virginity I want it to be someone I trust."
His sister leaned up and kissed her brother on the lips, and the forehead. She rolled him over onto his knees on the bed and kissed his lower back, pulling down the skinny jeans he was wearing, kissing his butt. She pulled them down only to his knees, reaching up to his panties and pulling them down to just barely below his tight virgin hole.
Her cock was already well lubed up from his saliva so she grabbed his hips and asked, "are you sure you're ready for this?"
He let out a soft moan and nodded his head, looking over his shoulder in reply. He was on his knees, his arms locked straight, back arched in a sort of girl push-up position. She grabbed her cock and rubbed it against his hole which made him shiver.
She began to slide it in, barely getting the head in as he bit his lip in sweet agony. She slowly slid it into him as his little ass adjusted to the pain. Finally all six inches were buried in his ass. The feeling is impossible to really describe. He could feel the cock, the heat and pulsating, against the sides of his ass. It was more sensitive than he imagined.
His sister grabbed the top of his foot, which was facing down, and held them in her hands as she fucked him for the first time. In and out the cock went, her balls slapping against his taint. That and his soft panting were the only noises you could hear in the room.
After only ten minutes he could feel the sensation beginning in his ass, traveling up his back and making his whole body shiver. He came harder than he had ever come before. The feeling charged all over his body like electricity causing him to have little muscle spasms everywhere. It seemed to last forever, as wave after wave of pleasure hit him everywhere for over thirty seconds. He collapsed face first into the pillow and just breathed heavily. This sent his sister over the edge, making her cum. Threads of hot sticky cum filled his ass, giving him another little orgasm which made him shiver again. This one only traveled up his back, but was still better than anything he had ever had before that night.
His sister pulled out and fell on top of her brother, kissing the back of his neck all over. She turned him over and he just smiled up at her. He had no words to say. He leaned up and kissed her forehead, and pulled her down so that he could lay his head on her chest. He fell asleep like a baby that night, a new man.
This is an experimental story. I usually write romance, but I'm testing the waters with other stories. I am not personally into cross dressing, or men so it will be interesting to see how this story turns out. Depending on the feedback I get I may try other genre's as well, but this will be it for cross dressing.