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The next few days passed like the last few. He had me on my knees at his beck and call. It was usually twice a day. Always with the plug buzzing away. God, it made me horney. A few times, he played with me after or before he blew his load, but I could never be sure. I was getting frustrated.
I had been thinking of ways out, but none of them would work. I was living a crossdresser's dream. Being forced to dress as a woman. Being forced to dress as a maid. A life of 24/7, frilly knickers, skirts, and blouses. Looking pretty, doing women's work. I still felt guilty that I had surrendered my manhood so easily. Was I really that much of a man to start with?
I felt the plug start to vibrate as I washed up. I nearly dropped a plate. I went to the study, but Sir was not there. I found him in his bedroom, naked apart from his dressing gown.
"I need your services, Sarah."
He opened his legs and I knelt on the bed between his legs and licked this balls.
"Oh, you naughty girl. You do love a bit of cock don't you? Soon you'll have even more."
What did that mean? I thought as I took almost the whole length of his shaft. My gag reflex had dulled over the last week. I was getting good at this. As I bobbed my head, he groaned and called me a sexy woman, a good girl, as well as other things.
This did things to me. It made me feel so wanton and feminine. I had the power to please him, and I liked it. He finished and told me to go to bed. I felt frustrated. I went to my room to shower and go to bed. I normally took the plug out to charge it, but I left it in. I changed into a white silk teddy and lay on top of the bed and rubbed myself through the silk.. It felt so much better when my rear was filled.
I closed my eyes and imagined what a real cock would feel like in there. I didn't hear the door open. I was just about to climax when I heard a cough.
"Sarah, you disappoint me. This won't do at all. You give me pleasure, your pleasure is mine to give."
I didn't know what to say. Had I given up that much control? I felt the plug vibrate, then his hand gripped my small, hard cock. The silk and the pressure felt wonderful. He gently masturbated me while the plug pulsed inside of me. I closed my eyes thinking of a real cock inside me, filling me. Warm, hard and real. Then I felt Sir pushing and pulling the plug. Pumping it in and out of me. I screamed a high-pitched girlish scream. Then came like I have never done before in my life. My whole body was shaking.
Sir looked down at me wide eyed.
"Well you did seem to like that. You are coming along splendidly, my girl. Now go and wash and change. Leave your knickers off. "
I went to the en-suite and put my soiled teddy in the laundry basket. I put the top half of a black lace baby doll on and returned to Sir.
He was holding a wire contraption in his hand. I had no idea what it was.
"Come here, Sarah. I can't have you distracted and playing with yourself all day. You will wear this from now on. "
He lifted my babydoll and fiddled with my balls and cock. I heard a click and felf my cock surrounded by cold steel. He backed away as I tugged on the contraption. It would not come off.
"Some men used chastity belts to make sure their wives stayed faithful. Think of it as a token of love. I will release you if you are a good girl"
After he left, I cried myself to sleep. One of the things that made this tolerable was getting off a few times a day. I had little control over my life now. I just hoped he would keep his word.
Three days later I was aching to cum. He kept the plug buzzing on the low setting. He had insisted I wear the French maid outfit. This one has a short skirt with huge layers of net petticoats. The petticoats tickled my legs with every movement. Every time I saw my reflection in the mirror I got so hard my cock ached straining against the bars of my cage.
The plug buzzed at full speed and I hastened to Sir's office.
"Sarah. I just realized I have neglected you for the last few days. I would like to offer you a proposal. You don't have to accept, but if you do I will reward you and remove your cage for a week."
"I would like that Sir. What do you want me to do?"
"I want to take you to the next level, Sarah. You look like a woman. You are starting to act like a woman. You are doing so well. I think you should experience sex as a woman. It will help you so much. You will be a lot more feminine. I will also reward you in another way. What do you say, my girl?"
I was shocked. I knew this was coming, though. It was a line I never thought I'd cross. Giving him a blow job several times a day was one thing, but letting him fuck me? Could I do this? In my mind, the tiny part left of my manhood screamed no. This will mean you're gay. The ever-growing Sarah side of me said, Do it, you know you want to feel a man inside you. Make yourself a complete woman.
I wanted the cage off. Before he put it on I was getting hard all day and wanking at least three times a day. I missed that. Even though I didn't have freedom. I was living a crossdresser's dream. I was trapped living as a maid. I would cum then feel guilty for about ten minutes. Then the feel of the clothes, the taste of my lipstick, and a glance in the mirror would remind me I was many men's wet dream. Long, silky, nylon-covered legs in a short skirt. I would get hard all over again.
I gave in without a fight.
"Yeah,Er yes Sir. What should I do?"
"Meet me in my room in twenty minutes."
My knees were almost knocking as I knocked on the door. The first thing I noticed was what appeared to be a long, padded wooden seat. On top of it was a metal frame with what looked like leather cuffs.
He saw me staring at the contraption.
"I know it's a bit kinky, dear, but the old Sarah used to love it. It will make sure you won't change your mind. Trust me, it will be worth it. You do trust me, don't you?"
What could I say? Part of me was scared, but part felt a wanton need. I loved the idea of being put in bondage, being the "victim".
"Yes Sir. Please be gentle. Please."
He kissed my cheek for the first time. I hadn't been kissed by anyone for years. My wife never liked kissing.
He guided me to the device. The frame forced me into an "all fours" position. My legs spread apart with cuffs on my ankles, fixed them in place. My head was locked in place by a collar supported by the frame. Both hands were cuffed to the side of the frame. I couldn't move. I was now helpless. A prisoner to his lust.
He removed his dressing gown and stood in front of me semi-erect.
"Open wide, my dear."
I lifted my head an left him slip his cock between my lips. I couldn't bob my head, so he fucked my mouth. I felt him fully harden as I used my tongue to stimulated the underside of the head of his penis.
"Good girl. Are you ready? Ready for me to make you a woman? Ready for me to fuck what little that remains of the man, out of you?"
I was ready. I never would have dreamed this would happen a few weeks ago, but I wanted it.
I couldn't see what he was doing, but I felt my dress and petticoats being lifted. I felt my knickers being lowered to my thighs. The felf relief as he unlocked the cage, My cock sprang to life. I gasped as he rubbed me slowly until I though I would cum. He drove me to the edge then stopped.
He carefully removed my plug and I felt empty. I moaned.
"Please, Sir! Please take me. Make me a woman."
I felt the head press into my well-lubricated hole. I cried out as it gradually forced its way in. It hurt, but it was a nice hurt. Inch by painful inch, he slid in. I had never felt so full. Not hard plastic, but a warm, fleshy, hard cock. I nearly came when I felt his balls hit my buttocks.
"Are you alright my dear?"
"Oh yes Sir. I feel wonderful."
I really did. There was pain, but I felt happy. I was having sex with a man as close as I could get to being a woman. I had a man inside my body. I was being passed by him. He was taking me. Using my body for his pleasure.
He slowly pumped in and out. I gasped and cried. He picked up speed and I felt him hit my prostate. A he thrust in hard, I let out little high-pitched sounds.
"Uh, Uh,Uh,"
Then I erupted. I shivered and came harder than I ever would have thought possible. I was passing out, but he was still fucking me. My whole body was shaking. This was the best orgasm of my life.
One last hard thrust, and he cried out. I could swear I felt him pump copious amounts of cum inside me. He collapsed on top of me and whispered in my ear.
"You're my woman now. You're my Sarah forever."
I felt like I was flying. I felt so good. It felt like a dream. I barely knew he was unlocking me. He gave me some tissues to clean up and hugged me. I put my arms around his strong chest. My man's chest. He looked down and kissed my lips. Our tongues darted in and out of each other's mouths.
"I didn't need the frame, did I? You wouldn't have tried to stop me. I knew you needed that to happen."
"I wasn't sure. But now it has happened, I can never go back. I need to be a woman. I realize it is more than just a kink. That felt so right. Thank you."
"Things will change now. Your reward is a day off tomorrow, and I am taking you out to dinner. Sarah, that is of course. Francis is gone forever."
This just got very real. Sarah would have to face the world for the first time. I was scared and thrilled at the same time.
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Comments
Question
I’m really surprised nobody commented this story. This must be probably due to the fact that this setting is one of the forbidden dreams of closeted crossdressers. Or am I mistaken ?
I write for fun and it helps
I write for fun and it helps me with "my condition" Wanting to express my feminine side but only being able to a few days a year. I publish on here, Fictionmania and Literotica. The story is going down well on Fictionmania, but Literotica audiences love it. Some chapters getting 4.77 out of 5.
This platform seems to appreciate pro-trans stories. My sexual stories never do well.I understand that. You can see they way this story is going. Sarah is coming around to idea, and is realizing she prefers being feminine.
Leeanna