My last year in high school, I was eighteen now it had been almost four years since mom and dad got a divorce. Dad moved away from the city to another town. My uncle John, dad's younger brother still lived in the same city. He had a condo in the suburbs. He also had a divorce a few years ago but he handled it pretty good. I always drove by and see him several times a week. Actually I thought he was a handsome guy.
I always wondered if John knew weather I was gay or not. I thought maybe the way I looked at him sometimes might have tipped him off. One day after basketball practice, I decided to swing by his place and maybe let him in on my secrete.
I got out of the car let myself in through the garage door. The house was quiet except for some music that was coming from John's room. The door was open so I just walked in. That was when I got the shock of my life. There was John all dressed up in women's clothes I mean wig, high heels, stockings and everything. He was dancing in front of the full length mirror.
By the look on his face I could see he was more surprised than I was was. He quickly turned off the music. "What. What. Are you doing here?" He muttered.
"I was coming home from practice. Thought I'd just stop by. What the hell is all this?"
"Please, Shawn. You've got to promise me. You'll never tell anyone what you saw here. Please, Shawn. No one can find out about this. If they did I'd be ruined."
That was when all the wheels in my head began to turn and spin. What an opportunity I had there. The big letters "Blackmail" came to light. Hell, I was a horny gay teenage and even if he was my uncle. Hell, I realized I had the upper hand. "Well that depends on what you can do for me."
John stared at me. "What's that suppose to mean?"
"You do what I want or I expose your little secrete."
"Shaw, why are you doing this?," John asked.
"In sports it's called opportunity. If you don't seize it then you loose."
"I don't understand."
"When I got a hot guy like you under my control. I'm not going to pass that up."
"I think you've taken this far enough."
I stood up and started to leave the room. "Guess I'll have to spread around the news. Might start with some of the guys down a school. Things spread fast down there."
John quickly stood up. "OK! OK! What do you want from me?"
"First we better start with who hold all the cards. ME! I want complete control. You do what I want. Otherwise I tell all."
John looked really hot standing there in that brown shoulder length wig wearing all that lipstick and makeup. "All right. Agreed."
"Good," I slapped my hands. "I always wanted to see you naked. Strip those clothes off for me!"
Reluctantly, John began unbuttoning his blouse and skirt. Then his bra, thigh high stockings and high heels. Last to go was his blue panties with the cock cup.
John's body was completely shaved no hair anywhere. His cock and balls, chest, arms and legs slick as could be.
"Put your high heels back on." I pointed to them. "Now parade back and forth for me."
"Please, Shawn. Don't make me do this."
"I like to see you cock swing when you walk."
My cock was rock hard as I watched him naked. My next test would tell me if he had accepted his fate or not. I stood up and dropped my shorts. My hard teenage cock sprang into view.
"I think I need a little sucking action here."
"Please, Shawn. Just because I dress in women's clothes doesn't mean I'm gay."
I smiled at him. "No. But I am."
I saw him take a deep breath. "Your dad was right. He told me a couple years ago. I said he was crazy."
"My cock is waiting. Get on your knees and suck!"
Reluctantly, he once got down between my legs and took my cock into his mouth.
"Move you head in and out over it! Let it rub on the top of your mouth."
By the time I was ready to cum he was getting the hang of it.
Quickly I pulled my cock out of his mouth and shot my load of sperm all over his face. "Now, go get yourself cleaned up," I told him.
I was watching television when John came in. He was all dressed like a man now. Green shirt Levi pants and a new pair of Nikes.
After that first day of awkwardness and John coming to grips with his situation, we began to get along. There was that age gap John had problems dealing with. He was forty-two, I was eighteen and I was giving him orders. John was humiliated easily and when he was humiliated he was very submissive. He was also very submissive when dressed in women's clothing. I knew that and used it to my advantage.
He never cross dressed that much before just some times when he was alone at home and feeling horny. I made him dress every day before I got to his house. Then I made him strip it all off down to his wig and high heels. One day I got the idea to put a little spanking into the mix. He had just finished stripping.
"Turn around," I ordered. "Put your hands behind your back." I buckled them together with a small leather belt from his skirt.
"What are you doing, Shawn?"
I picked up his panties , shoved them in his mouth and duck taped his mouth.
"You've not been that good of girl. You don't shake your ass for me enough. So I've decided to give that little ass a good whipping."
His first reaction was to start shaking his head because he couldn't talk. I was really enjoying this now. I bent him over the arm of the sofa so his ass was fully accessible.
I took a found a large hair brush in the bedroom and a nice leather belt. "We'll have to see which of these works the best," I said, pinching him on the ass.
The hair brush made his ass red after about ten strokes. I grabbed his cock and balls and pulled them up between his legs. "I sure hope I don't hit these with the belt." I gave him ten more whacks with the belt and his ass was good and red. I could tell he felt every smack because tears were coming from the corners of his eyes.
I knew the time was right to fuck him. I poked his pucker with the head of my cock, easing it in a little each time. His body flinched and the head popped in and it was good to go from there. I dreamed of this day, fucking my hot uncle. I gave his ass a real work out before I ejaculated in it.
That was my first time playing around with bondage. I was surprised how much fun it was.
Two days later I stopped by John's. He had improved on his stripping ability. He pranced back and forth, wiggling his ass and he made used of his hands to rub his cock and balls.
"Put your hands behind your back," I ordered.
"But didn't I do everything right?"
I quickly strapped his arms together, put the panties in his mouth and duct tape.
"You did do everything just great," I said. I slapped his ass hard with my bare hand.
"I'm just going to spank you because I feel like it."
I looked down at his face. When the tears formed at the corners of his eyes, he had enough. His red ass was very tempting. I dropped my pants and gave him another hard fucking.
I stood him back up and untied him. "Get your ass dressed! I want you to strip for me again. I made him strip two more times that night before and suck my cock once before I left.
I could tell uncle John was enjoying his new found domination. Before there was only himself and as everyone know that gets very boring. He was now becoming what you might call "my bitch" but I never called him that. He never knew what I was going to do and I think that was the arousal part for him. I came over Friday he was waiting for me in a beautiful dress flower dress with black stocking and black high heels. As usual his wig and makeup was perfect.
I walked in and glanced at him. "Show me you cock!" I could tell I caught him off guard. He started to unfasten his dress.
"I said show me your cock! Not strip! Now get it out!"
He quickly pulled up his dress and pulled down his yellow panties. He held the dress up with his left hand and held his cock in his right hand.
"Good. Now go get me a beer from the kitchen."
He returned with the beer and handed it to me. "Show me your cock again."
This time he did it much quicker. He held his dress up with both hands and his panties were down to his knees. I reached over and played with him until he got an erection. Then I played with his balls.
"I think it's time we call you Joan. From now on that will be you female name."
He looked down at me and smiled. "Now, Joan. Turn around and show me your ass!"
I knew she was waiting for the belt to strike. Instead, I rammed my finger up her tight ass. She gave out a yelp and jumped forward. "We're going to call that your pussy from now on."
I just sat there laughing. I shoved an ash tray to the end of the coffee table.
"Fill it with your sperm!"
She held her dress up again with her left hand. Her right grabbed her cock and began masturbating. She spread her legs out wide over the coffee table and tried to aim her cock at the ash tray. She almost got it all except for one drop.
"I see you failed at that. You know what that means? Your ass needs a good whipping!"
The next day was Saturday and I had a great day planned. Aunt Joan and I were going out shopping. Joan wore this colorful summer dress withs a big white sash. I made Joan drive so I could play with her cock under her dress as we drove along. It was a lot humiliating fun. Our first stop was the adult shop downtown. We needed to get a ball gag, leather cuffs, dildos and some vibrators. I made Joan pay for them because I know how humiliating that was for her.
Next we drove to the mall. In a pet store, I found some really neat leather collars. Black, pink and red. Then we ran into some friends of mine from school.
"I'd like you to meet my aunt Joan. My dad's sister."
I noticed a lot of guys at the mall checking her out. She had some great legs and a great figure.
When we got back home I told her the news. I had decided to move in. I told her if she wanted to keep her dark secrete, she had no choice in the matter. Mom was already dating some guy and I didn't want to be around that. I had already told her uncle John said it was fine to stay with him. I gave her the freedom to dress in whatever she liked. She could look a sexy as she wanted that just meant I was going to fuck her harder.
There were only two outfits I ordered her to wear. The maid uniform which was a real turn on for me and her. The whore uniform which was high heels, thigh high stocking and a wig. Nothing else. Those uniforms usually ended with her being tied up, milked and fucked. I think by this time she forgot about blackmail and was enjoying the servitude.
Then came the next test for aunt Joan. I was not sure how she would react so I tied her up first. There was an old piece of exercise equipment in the den that had a t-bar across the top. It was perfect to hold her arms above her head. The rails below were perfect to tie her ankles so her legs would be parted. She was dressed only in high heels, wig and ball gag.
I would sometimes tie her like this when I wanted to milk her. Her cock glans were sensitive. This way she couldn't get hurt because she was not able to move around much. I know she thought it was just another night of sexual fun. She was right she just didn't know there would be others. I had invited two of my gay friends from high school.
The look on her face was that of sheer terror and humiliation. Carl and Frank were team mates of mine. I knew I could trust them that was why I had invited them over for some fun. Carl ran his hands up and down aunt Joan's naked chest.
"She is really fine. I like the soothe no hair anywhere look."
Frank quickly made his inspection of Joan's shaved cock and balls.
Frank smiled. "She's hung pretty good. She must be big when she's hard."
Carl, who was now rubbing Joan's soothe ass cheeks. "We'll see later on."
Frank stepped back to look at her. "I like the bitch look. Wig, makeup and the high heels. Real sexy!"
Carl smiled, "yeah. Makes me hard!"
That Saturday evening was one I'm sure aunt Joan would never forget. The guys spent almost two hours playing with her. Finger fucking him and pinching his nipples made him hard every time. They got him hard several times just to let him go soft again. Carl fucked her once as she hung from the t-bar. Then Frank got down and sucked her cock dry. Later we untied her then made her suck all our cocks, one at a time.
I was surprised at aunt Joan. I think the presence of Carl and Frank humiliated her so much she automatically slipped into submission mode. We ordered her to dress sexy then made her strip for our entertainment. We made her stroke her cock and finger her pussy ass. Carl got her hard then sucked her off right there in front of us. Me and Frank bent her over the sofa and fucked her hard.
We even made it easier for aunt Joan to keep in the mood. We never used aunt or auntie or Joan. She seemed to like slave, bitch, cunt and whore so we used those terms only. Carl and Frank became regulars at the house. Carl seemed to be the best at verbal humiliation and Joan responded well to him. She would be dressed in the maid uniform usually. Carl would come in.
"Bitch! Get your pussy ass naked. Then get over here and suck my cock off!"
Joan would immediately react to him, stripping down, darting across the room and gobbling his cock up in her mouth. It was fun to watch.
"Rock your hips while you suck, whore! I wanna see your dick swing."
She did exactly that, rocked her hips in rhythm with her sucking. Her cock and balls swung nicely up and down.
Another thing Carl taught her was hands free ejaculation. He tied her to the exercise machine, legs spread over the bench seat, her arms tied to the back bar piece and a ball gag in her mouth.
"Now, concentrate!" Carl quickly slapped the head of her dick. "Get hard and keep twitching your cock until you cum. It's done all the time. You just have to concentrate on getting your pussy balls to unload."
Occasionally, Carl would go over and slap her across the cock. "Com'on bitch! Get your fucking cock moving! Let's see it jump up and down!"
Joan was twitching her cock for all she was worth. Her hips were even gyrating.
Carl slapped her cock again. "Hurry up! Before I rape your cunt ass!"
Apparently that was all it took some encouragement from Carl.
She groaned once, her cock snapped up and a spurt of semen shot out. She twitched again and another glob came out. Her cock was pulsing now and the sperm was coming at a steady rate. I just sat there with a smile on my face I was totally enjoying this. Carl scooped up the sperm from the bench seat and smeared it all over Joan's face. "Now you look just like a whore! Face full of cum and your cock dripping wet."
We left her tied up there while we went to get some snacks and beer, then watch some television. About a half hour passed and I looked over at her. I nudged Carl. "Her cock is standing straight up again."
Carl smiled. "I think it's time to use the vibrator."
Carl returned with the vibrator which he placed on the seat so she could see it. "Time to see how much juice you got left in those pussy balls. But first a little fun"
He reached out with his thumb and fore finger, then began pinching and twisting her nipples. Her hips and thighs started to shake which made her cock sharply snap up and down. We could just hear her muffled cries through the gag each time Carl pinched her nipples. Carl stopped working the nipples and began slapping her cock up and down "I could do this long enough and she would cum."
He picked up the vibrator, plugged it and flicked the switch. "I'd rather do it this way. I want to see how much her cock can take."
He slowly placed it under her balls and worked it back and forth. We could tell she was trying to close her legs but the bench kept them apart.
"Your balls a little sensitive to the vibrator, bitch?"
She quickly groaned and nodded her head yes.
"Good! Let's do it a little bit more."
Frank and I both laughed. I knew Carl wouldn't her her really. He could have pushed that vibrator a lot harder than he was.
He slowly moved the throbbing machine up and down the stiff cock, first the front then the back, bending it downward thumping the head of her cock with the vibrator. We could still hear the moans and groans she was making through the ball gag. Then Carl grabbed her cock and held it steady with his left hand. Then he placed the vibrator right on top the swollen head and let it thump.
Suddenly, Joan's body heaved forward, then jerked and jerked again. I could see a small amount of her sperm oozing from the cock slit. Carl moved the vibrator back and forth over the head while Joan was tossing her head from side to side. Carl turned the vibrator off, tossed it on the bench seat then slapped her across the cock head. "You fucked that vibrator like a real whore!"
Joan was pretty much used up. Her chest was covered with drool that ran from the ball gag. There was so much sweat on her face that her make up was running together. We untied her and let her go to her room to shower and clean up. I slapped her hard across the ass as she went by. "When you finish. You get your pussy back down here. I want kneeling naked on the living room floor."
She did as ordered, came down stairs naked and kneeling on the on the floor. Frank made her put on red lipstick. He wanted his cock and balls kissed all over so he could see the lipstick. It looked like fun so we all had it done. It was about two in the morning before we all fell asleep. I woke up to the sweet smell of fresh brewed coffee.
Aunt Joan was in her maid uniform prancing around the kitchen getting breakfast ready. She fixed me coffee and placed it in front of me on the table. "Anything else?"
"Just a couple pieces of toast for me."
She quickly dropped two slices and waited until they popped up. She buttered them, placed them on a plate and opened a jar of jam. "Would you like me to put some on your toast?"
I reached under the maid skirt and grabbed a handful of balls. "I guess you like the way things are going?"
She smiled then moved my hand onto her hard cock. "I wouldn't change a thing."
End>>>>>>>>>