Blackmailing the Cross Dresser
By BMAN.
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It was the beginning of a new year in the large suburban neighborhood where 17 year old Mason lived. It had been a good Christmas because Mason got a new telescope as a present. Mason was somewhat of a nerd, into science and astronomy more than anything else. He was also gay, but he kept that hidden from almost everyone except his best friend David.
Mason was busy setting up his new scope on new years day; when he noticed something. Across the back yard and over on the next street. He could see right into this bedroom. There was a man laying almost naked on the bed. He was wearing a red corset, a garter belt with black lace stockings. His legs were open and he was using a dildo. Mason quickly put the camera adapter on the scope and mounted his digital camera.
Over the course of the next week, Mason took about fifty photos of the man in many compromising positions. He was always dressed like a woman; wig; fake boobs; makeup and lipstick. He had a closet full of women's clothing. He was completely shaved; arms; legs; chest and crotch. Sometimes he would tie himself up, including his cock and balls. He wore a leather studded collar around his neck and a ball gag.
In the corner, there was a pole with a large dildo attached. Mason would see him kneel down and suck on it. Also a chair with a dildo attached to the seat. He would lower his ass over the dildo; bounce up and down as he masturbated. This was very arousing for Mason and his friend David. They would wank each other off as they looked at the pictures. Mason found out the mans name was James Crawley.
It was then Mason and David hatched their plan to blackmail him for sex. What could be better for two gay boys than having a sex slave? Mason placed some pictures in an envelope and placed in his mail box along with a note. It contained an email address Mason created on his computer. The instructions were to make contact. Mason warned him that he had many more pictures and he could put them on the internet with just the push of a button.
That evening there was a message on the email.
"Please tell me what you want. I'll give you whatever it takes. Please don't show any of these pictures. Please. Tell me what you want."
Mason had an astronomy club meeting Friday night. He replied.
"I'll come by Friday evening after 8. I'll knock once."
He replied.
"No, please. I don't want you to come to the house."
Mason replied.
"It doesn't matter what you want. Wait for my knock."
He replied.
"Alright."
The astronomy meeting was over by 7:30. Mason parked his car at the end of the block and walked to the house and knocked once. The door opened and James stood there with a shocked look on his face. "You left the pictures?" Mason pointed. "Let's go inside."
He closed the door and started at him. "How old are you?" Mason took offense. "Seventeen. There are two of us. And we have a lot of pictures of you in women's clothing." James shook his head. "What you're doing is against the law. It's called blackmail. It's a felony! You can go to prison for a long time. Do you want that?"
Mason smiled. "Only if we're caught." James took a deep breath. "How much money do you want? I have some saved up. Just tell me how much." Mason shook his head. "No money. We want sex." James pushed back in the chair. "Sex? Are you serious?"
Mason adjusted his glasses. "I'm very serious. Sex or I send all the pictures over the internet." James shook his head. "I'm twenty three years older than you. Do you realize I'm old enough to be your father?" Mason laughed at him. "My father doesn't look anything like you. And he don't dress in women's clothing."
James shook his head again. "I don't care. I'm not having sex with a seventeen year old! That's a bigger crime than blackmail!" Mason stood up. "Ok. I guess we're done. I'll send you the site where I uploaded your pictures tomorrow."
James quickly jumped up "OK! Wait! I'll agree to giving you oral sex. In exchange for all the pictures." Mason unfastened his pants. "Start sucking." James got on his knees and began sucking Mason's hard cock.
It had been a long time since James had a real cock in his mouth. He almost forgot the feeling. Suddenly, Mason squirted his mouth full of sperm. James wiped his face clean with his shirt sleeve. "There. I kept my end of the bargain." Mason pulled his pants up. "I didn't agree to anything. I just said start sucking."
James stood up. "Look. I can give you money. I have a good job. I could even pay you every week. Just give the pictures." Mason laughed. "Sure. When I do you quit paying. Do I look stupid? You think one suck and it's over? I told you there was two of us." James sat down again "Ok. Just tell me how long do I have to give oral sex before I get the pictures?"
Mason stared at him. "I was thinking more along the lines of a sex slave." James sat up straight. "Are you serious? A sex slave? I'm too old to be a sex slave." Mason had a big grin on his face. "That's what makes it so thrilling. Two teenagers having an old man as their sex slave. Exciting!"
James stood up. "I think you've gone too far with thing. I Think you're bluffing." Mason headed for the door. "Then we're back to the web site with all your pictures. I'll have them posted tonight." James quickly replied. "OK! I can't afford to have those pictures seen by anyone."
James hung his head as he sat back down. "Tell me what you want me to do." Mason turned around an looked at him. "For now this would just be on the weekends. When me and David are not in school. You would be our weekend sex slave. All day Saturday and Sunday."
Still staring at the floor, James took a deep breath. "What is a weekend sex slave expected to do?" Mason smiled, looking down on James. "Glad you asked. David and I have given that a lot of thought. Usually sex slaves are kept naked. But we like you dressed as a female. You look more sexy."
Mason sat down. "Some rules. David and I will only be addressed as Sir. You speak only when asked. You obey whatever we say. No questions or rhetoric. Only yes Sir." James interrupted him. "Why don't you just come over and have your sex and leave. Wouldn't that be the same?"
Mason chuckled. "There is no fun in that. Think of it as a role playing game you do every weekend. You are conquered by your enemy. You must become a submissive little pussy." Mason stood up. "You can think about it. Send me the email with either yes or no. Tomorrow is Saturday."
The next morning Mason opened the email James sent.
"Yes."
Mason and David were pleased to see James was fully dressed as a female when he answered the door. David smiled. "Very hot looking woman." Mason pointed. "This is my friend, David. He's only seen you in pictures." James quietly closed the door.
At first, James felt a great deal of humiliation. Forced to submit to these two arrogant teenagers. Giving in to their every whim. However, James did like being the center of attention. He didn't even mind the remarks they made no matter how crude they were.
James decided if he was going to be a sex slave; he better make the most of it. After all, in time these teens would get over this phase and move on to something else. Mason and David leaned back in the sofa and unfastened their pants. "I feel like having your hot lips on my cock. Suck us both off before you clean the house."
James slowly got on his knees in front of Mason and opened his pants. He was met by a very hard erection. David watched eagerly while James sucked Mason's cock. James knew what was coming next. It would be David's turn. Mason whispered to James. "In case you haven't figured it out by now. We're both gay."
They made James wear the red corset and black stockings while he cleaned the house. Occasionally they would fondle him as he worked. It was 11:30, James put the vacuum away and went to the kitchen. "What would Sirs like for lunch?" Mason and David plopped down at the kitchen table. "You know, I always like grilled cheese sandwiches and tomato soup."
David rubbed his hand over James smooth ass cheeks. "When you finish. We have a surprise for you." They took James to his bedroom where they found all sorts of toys. He was ordered to dress in the black and white maid uniform with all accessories. Wig; fake boobs; make up; stockings; panties and high heels.
David found a nice leather wrapped ring gag for him to wear. A leather collar for his neck and cuffs to hold his hands and arms behind his back. This was a fantasy come true for James. One that he had lived out many times, but this time it was real. These two teens were in charge and it would not stop until they decided.
Mason found several paddles and a couple small whips hanging in the closet. Mason held the small whip up. "What's this for?" James quietly replied. "A crotch whip, Sir." David and Mason smiled at each other. David snapped the ring gag in place.
Mason clipped a leash to the collar and they pulled him around the house like a dog on a leash. They came to a stop in the living room. Mason bent James over the arm of the sofa. David pulled the maid dress up and tore the panties off. Mason swung the paddle back. "I think it's time for a little punishment!"
James felt the blistering sting of the paddle as it smacked against his bare ass. It was then James realized he would rather be a submissive sissy instead of a man. Mason said it...you are conquered by your enemy...you must become a submissive little pussy. The leather paddle brought tears to his eyes, but also joy to his inner sole.
Mason yanked him up from the sofa. "You like being a sissy bitch?" James grunted and nodded his head yes. Mason quickly bent him back over the sofa and pulled the dress all the way up. He slowly slid his lubricated cock between the red ass cheeks and deep inside James.
Mason fucked him for a short time before making his deposit of sperm. David rammed his hard cock deep inside James and fucked him again. Mason noticed the pool of sperm on the sofa arm and the drippings on the floor. James had ejaculated during his breeding. Mason pulled James to his knees by the sofa.
He shoved his semi-hard cock through the ring gag. "Clean it! Or I'll whip your balls." James licked with his tongue as fast as he could. Next was David and he cleaned his cock just a good. Mason took the cuffs off. "Take that uniform off!"
James was naked except for garter belt, stockings and high heels. Mason cuffed his hands back and made him kneel on the floor with his knees wide open. Mason switched on the TV. "You better stay there and be quiet." After the show, they took James into the bedroom and tied him to the bottom bed rail.
Arms behind his back, legs spread wide open and feet tied to the bottom rail posts. Mason picked up the crotch whip and walked over to James. "I always wanted to whip somebody's cock and balls. I guess you're it." James grunted several times and shook his head.
Mason twirled the whip around in his hand. It made a very distinct whooshing sound. With every strike of the whip, James gave out a loud grunt. David was excited watching and rubbing his own crotch. Within a short time, James's cock was fully erect. His scrotum and cock were red, but he was aroused to no end.
Another strike of the whip and suddenly his cock erupted. The milky seed flowed from the tip of his cock all the way down his red cock to his red ball sac. David quickly reached over and grabbed the spitting cock. James bucked; whined and whimpered as David milked every last drop out of him.
By this time Mason and David were totally hard. The threw James across the bed and took turns breeding him again. James was laying naked on the bedroom floor. Mason took the cuffs off and tossed them next to him. "Tomorrow is Sunday. Hope you're ready for a whole new day."
James became acceptable his circumstances over the next several months. He went to work; came home every night and stood naked in front of the bedroom window as instructed. Mason and David would watch him in the scope. On the weekends, he became the submissive slut they wanted and the one he enjoyed being.
Mason and David loved the control the held over this 40 year old man. Now that the schools were out for summer vacation, they would have more time with James. As for James, his fantasies were being lived out. He could dress like a woman in different clothes every day. Something he loved to do.
Mason and David would undress him; breed him; masturbate him; spank him and generally humiliate the hell out of him. It was the feeling of power that stimulated them. James could only wait and see what they had in store for him next.
END.