"Paul I really think we can win this" Laura told me "we have a month to get ready"
"Alright if you think you can do it" I said. I was actually very excited by the idea. Laura had read about a costume ball for Halloween best costumes was $1500. There were sub areas scary and such. But She thought sexy. And thought to change it up I would go as a woman and she would go as a man. But we had to be convincing we both agreed.
"So you will do it? no whining and complaining" she asked.
"Yes, I will give 100%. I would worry more about your end of it" I told her.
"Sounds like a challenge." She smiled.
"Well yeah it is I guess" I shot back
"OK, Your on. We have 36 days from now. Who ever is more convincing in their role wins" she said sticking out her hand I shook her hand.
"Deal, what does the winner get?" I asked.
"No chores, the loser does all the chores for a month" she suggested. I agreed.
We started with her first. I tried to get her to walk like a man. It seemed hopeless after about an hour.
"Well I have no shoes that will fit you, so let's start with shaving" Laura smiled leading me to the bathroom.
"Couldn't this wait?" I asksd
"Trust me you will want to be use to it" she informed me. We used hair remover and a razor it was over an hour be fore I walked out of the shower. Completely hairless except the top of my head. She was right it felt strange. We spent the rest of the day with our normal routine. Laura took every opportunity to correct how I moved. Bending, walking, even how I, oved my arms. Things I had never thought about. I was focused on myself and didn't even think about correcting her. That night we made love her hands roaming over my smooth body. Seemed to stimulate her into taking control. She just pinned me down and got on top.
Over the next week she continued to focus on my movements. Even dancing she would take the lead. Laura had ordered high heels in my size and made me wear them around the house. At first I could barely walk in the 3 inch heels. But got better. I wore them everyday from the time I got home till I went to bed.
Even our friends became invested in our bet. Choosing sides of who would win. Laura was the favorite to win. So I tried harder.
"Are you ready for dress up?" She asked on Saturday morning. We were 15 days in.
"Sure" I told her. She produced a whole outfit. From stockings to a hat. First it was a sexy lace thong.
"No one is going to see what underwear I have on." I told her
"It's a state of mind. You will feel sexy" she told me. She helped me with the bra and silicone inserts.
"We will get you ones that glue on for the party" she told me. Then showed me how to put on stockings. And a garter. Then a low cut short f or fitting dress. I spent the day trying to remember to keep my legs closed. Laura had bought herself a cock. Seriously she wore it under her clothes so she could feel more mascaline she told me. She loved to smack my ass or come up and push her cock against me. Like I did to her so many times.
Over the next week or so I dressed everyday after work. Laura didn't seem to put that much effort into it at all. Other then she seemed to be in control. I tried to initiate sex one night.
"Sorry not into the lesbian thing" she laughed. But the next night she took control and iniated sex. She started to suck my dick. She pulled my panties aside and pushed her finger into my ass.
"Relax all girls need to lose it eventually" she laughed and continued. It felt amazing after the first shock. And she soon worked in a second finger. She swallowed my load but then kissed me I could taste my cum on her lips. The next day she plucked my eyebrows and experimented with my make up.
"I am so going to win this" I teased her.
"Think so? Want to up the bet?" She challanged
"OK double it" I said confident I had it locked. She pushed against me. She was wearing her cock.
"Want to show me how much of a woman you are?" She smiled an evil grin. "You liked me playing with your ass, maybe your mouth likes it too" she asked. I looked in the mirror I looked like a woman. I thought then looked up at her. I noticed her eyebrows where thicker. Maybe she had been preparing for this party more then I thought.
"Go ahead baby suck my cock" she teased. And she pulled out her 6 inch pink cock. I don't know why but I leaned over and took thr tip in my mouth. She loved it
"OH yeah, suck my big cock" she moaned. "Your going to swallow it all" she continued. The more she said the harder I tried. I never took more then 2 inches. The whole thing turned me on so much my cock strained against my panties.
"Get on the bed" she told me. I took off the dress and laid in bed. She was naked a moment later.
"Role over sweetheart, I want that ass" she told me luring her cock
"I don't think" I started and she insisted I rolled over and she lubed my ass. She went slow but soon she was fucking me with her cock. After that I felt more femine, and submissive to her in averting we did. She fucked me several more times before the party as well. We had a dress rehearsal the day before the party. Laura took me out to dinner. Fully dressed. The waiter thought we where a lesbian couple. Calling us both miss.
On the way home we stopped at John and Cathy's. friends of ours to get their opinions. They both thought I was absolutely convincing. But Laura was just to femine looking. Laura was a bit disappointed by it.
"Well maybe I should have fucked your ass more" she said. John spit out his drink in surprise.
"You didnt?" Cathy laughed
"OH she loves it, don't you?" Laura asked me. I had turned beet red and just stared at the floor. Laura rubbed her cock thru her jeans.
"Want to see?" Laura said pulling out her toy.
"You know your going to suck it so don't play shy" she told me. "Or would you rather I fuck you in front of them?" I kneeled and took her toy in my mouth. John was obviously turned on by the scene as his bulge grew in his pants. Laura caught me looking
"Do you want to try his? Do you want a real one? She teased.
"Go ahead" Cathy assured me. Laura led me to him. I didn't want this did I. But I knelt and pulled out his cock. I held it in my hand. The heat that came off it he wanted me. I thought as I started to suck his cock. It was longer the Laura's toy but thinner.
"Better make him cum, I don't want to have to finish it" she told me.
"His balls Paul, rub and suck his balls" Laura encouraged
"This is so hot" I heard Cathy say just as John stiffened someone held my head so I couldn't pull away and John came in my mouth. Cum dripped out of my mouth all over my dress. I swallowed some.
"Now your a woman" Laura told me. We left. At home Laura had me ride her cock cowgirl style till my legs cramped.
My ass was sore in the morning but she still shoved a plug into it and had me shave and get dressed. In a pair of her yoga pants.
"You liked last night." She stated. I could not deny that.
"Sucking John's big dick" she added
"I am willing to declare you the winner." She told me. "But then after tonight it all goes away" she explained
"Or you could forfit. And continue exploring this side of you" she said she gave me till midnight to answer.
As we went to get ready for the party. Laura pulled out a new outfit. It was completely pink from a frilly lace thong to the bows for my hair. She helped me get ready. I looked like some kind of little girl fetish. With pig tails. Laura dressed as a old school marm. Complete with a big ruler.
"I changed it up two weeks ago when I knew you where going to win" she told me. Smacking me with the ruler. I felt nervous in this costume I was obviously dressed for kinky sex. But Laura insisted.
When we got there, there was alot of really good costumes and doubted our chance to win. Laura led me to a small table in the corner. An older gentleman was sitting there. He was not in costume.
"Isn't that" I started. Laura walked right over and kissed him.
"Paula you remember Mr Bellows" she said. It was her boss. She pushed me onto his lap. And sat across from us, his hand was immediately up my skirt. Laura put her finger to her lip.
"Shhh" is all she said. I felt him get hard against my ass.
"Are you a good girl, or a bad girl" he whispered in my ear and kissed my neck. I was rock hard and it pushed my skirt up anyone walking by would notice.
I didn't know what to do or say.
"A good girl?" I answered. He kissed my neck again. And stood up making me stand as well. He handed Laura a room key and turned to leave. Laura stood close to me.
"A good girl follows him to his room" she said pushing the key into my hand. I took it and Laura took my hand and led me to the elevator. Mer Bellows entered first. As soon as I entered Laura pushed me against him. And remained downstairs.
Mr Bellows led me to a suite on one of the upper floors. There was a tray of sex toys. And bandage gear. He just started to undress me. He picked up a small velvet bag.
"I would like you to wear this" he told me. I looked inside. The look on my face must have given him a clue.
"It's a chastity cage" he informed me ans showed me how it went on. I hesitated.
"I will double the prize money" he told me. And rubbed my ass. I went to the bathroom and figured it out. I used a towel soaked in cold water to rid me of my erection.
When I came out he was naked sitting on the bed. I knelt and took his huge cock in my mouth. After a few minutes he had me stop. He handcuffed me and bent me over he pushed something very big into my ass. I screamed as he did.
"By the time I am done you will take much more then that" he told me and added a gag. After a few minutes he pulled the device from my ass and inserted his cock. He held me down as he used me. I was in tears when he finished. He immediately shoved a toy back in.
He then tied me face down on the bed. When the first smack came I almost had a heart attack. But then one after the other with a strap or paddle I thought. But soon I was crying I tried to beg him to stop but the gag I couldn't say a word. He tore the plug out and mounted me. Coming a second time deep in my ass. Then again plugged. He told me over and over that I was his now. And would do whatever he wished. He then let me get up and wash up.
"Go lay across the desk" he told me. I did without question hoping he would let me go if I did. He bound my ankles and wrist to the desk.
"You want more" he told me. I had not said a word. Still gagged. This time it was a leather strap that landed on my thighs ass and lower back. He showed me a plug the size of a tennis ball. Then I felt as he tried to make it fit. It wouldn't fit so he used toys and his fingers to lossen me even more till it did.
As it pushed in finally I passed out.
When I came too. My throat was sore and I tasted cum. The ball gag was gone so was the restraints. And plug. It was morning and I was naked in the bed. I got up to pee. And realized I still had the cage but now it had s small lock on it. I made a mess and finally just sat to pee. I took the longest hottest shower of my life. Found my phone and called Laura. She would be down to pick me up. I had no choice but to put back on the pink dress. I found a brightly wrapped present that said Paula on it. I opened it inside was a gold necklace. With a charm that said Nicholas's girl.
Laura came up to the room. She had not bought me any clothes so I had to walk through the hotel dressed like a school girl. As soon as we where in the car.
"I forfit" I told Laura who just smiled. And helped me put on the necklace.
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