Cross Dresser Enslaved

CROSS DRESSER ENSLAVED

A Fictional Account Of A Cross Dresser’s Fantasies

PROLOGUE

I am a cross dresser and a slave to my wife and her friends. Let me tell you how I got this way.

Since I was a little boy, I liked being tied up. I had always had a petite, almost feminine body. When I was 15 years old I started dressing in my mother’s lingerie and fucking myself with whatever I could fit inside my ass. I also gave my first blow job to one of my friends. This was my only sexual experience with a guy before my wife’s friends, but it got me hooked. I started to fantasize about being tied up, and raped by men while I was dress as a girl. Eventually, thanks to the internet, my fantasies started to include severe whippings and other forms of torture.

These fantasies remained just fantasies until one night; my wife started asking me about my deepest secrets. It took awhile, but I finally got the courage to tell my wife about my fantasies. She was shocked at first, but the more she thought about it, the more she decided she wanted to try it. We spent the entire next day with me tied up and her whipping me, paddling me, torturing my nipples and fucking me with a dildo. I loved it and so did she. From that day on, I became her slave. She became insatiable. Almost everyday she would tie me up and abuse me. The only thing she would never do was dress me up like a woman. Even though that part of my fantasies didn’t come true, and she wasn’t a man, I was in heaven. 

One day she changed her mind about dressing me up. That’s where this story starts….

Day 1

My wife woke me up one morning before work. This was not unusual as this is when she would give me my instructions for the day if I didn’t have to work. I knew this week was going to be tough because I was on vacation from my job. But her instructions today were unusual.

“Alright dear,” she told me, “listen carefully.” She grabbed me with both hands by my nipples and pulled, causing me to give a short scream. “Are you listening?” She gave my nipples a twist.

“YES MISTRESS!” I screamed.

“Good. This morning I want you to spend the entire morning shaving your body smooth from the neck down. I want you completely smooth when I get home. Oh, and I want you entirely naked all morning too. Understand?”

“Yes mistress,” I told her, confused. “but why?” I asked.” She had never wanted me to shave my body before.

“Just do what I tell you slave!” she shouted and twisted my nipples again causing me another scream.

I just nodded my head and she let me go.

“I’ll call you at noon when I go to lunch with further orders.” She told me, then turned and left

I lay there wondering what she had planned for me until the pain in my nipples subsided, then got up and did as instructed. I wasn’t used to shaving myself so it took me awhile to finish. When I was done, I inspected myself in the mirror to make sure I didn’t miss a single hair then went to watch TV until she called.

At noon exactly the phone rang.

I picked it up, knowing who it would be. “Hello?”

“Are you completely smooth?” my mistress asked me.

“Completely mistress.” I replied.

“And are you wearing any clothes?”

“No mistress.” I told her. “I’m entirely naked.”

“Good.” She said. “Now I want you to go and look under the bed. There’s a black box there. I want you to get it out and open it.”

Once again I did as instructed. When I opened the box I was surprised at what I saw.

“What are these for mistress?” I asked.

“They’re your new clothes, slave.” She replied. “First take out the garter belt and put it on.”

I reached into the box and pulled out a white garter belt with four short straps with clasps on the end. My hands were trembling as I slid it around my waist. I couldn’t believe it. One of my greatest fantasies was coming true. I was going to be her slave girl!

“Good.” She said when I told her I had it on. “Next pull out the stockings and put them on. Make sure you strap them to the garter belt. It’s there to help them stay up.”

I pulled out a pair of white lace top stockings and slid them on, savoring their feel against the smooth skin of my legs, then clasp the straps of the garter belt to them. One in front and one in back on both sides.

“They’re on, mistress.” I told her.

“Now take out the shoes and put them on.” She said. “I’m sure they’re you size.”

I brought out a pair of white pumps with a four inch heel and a strap that went around the ankle. Lovingly, I slid them on and buckled the strap. They fit perfectly.

“They’re beautiful mistress.” I told her. “Thank you.”

“You’ll thank me tonight.” She replied. “Now take out the chemise and put it on.”

I took the chemise out of the box and felt it between my fingers. It felt thin and smooth and my body ached to wear it. I almost moaned as I slid it over my head to hang from two thin straps from my shoulders.

“Now go to the mirror and tell me what you think.” She instructed.

We had a full length mirror in the bedroom and even though I was unsteady on my new shoes, I turned, staring at myself from every angle. I couldn’t believe my eyes. I had never looked like this in my mother’s clothes. Thanks to my small frame, I actually looked like a flat chested woman from the neck down. I knew that it wouldn’t take much work to look like a woman from the neck up either. Just a little make up.

“T-thank you mistress.” I stammered. “I love it.”

“Good.” She told me. “There is also a dress in the box but I don’t want you to put it on yet. That’s for later. Look under the dress and tell me what you see.”

I lifted up the dress and took a quick look at it. It was a small black spaghetti strap dress. I set it to the side quickly. I knew that if I stared at it too long, I wouldn’t be able to stop myself from trying it on. I reached into the box and brought out what had been underneath the dress; a large butt plug and a tube of lubricant.

“Okay, slave,” my mistress said, “lube that plug up real well and insert it in you. I want it to stay inside you for the rest of the day. You’re not to take it out at all.”

I didn’t even hesitate in my answer. “Yes mistress.” Was all I said.

“Good girl.” She replied. I blushed at being called a girl and found myself getting even hornier than I already was. “I want you to spend the rest of the day practicing walking in those heels. They’re 4” heels so be careful. I’ll call again before I get off work with more instructions.”

“Yes mistress.” I said again.

“Have a good day Leann.” She told me, then hung up.

I sat there just staring at myself in the mirror holding the plug and the lube. The name she had called me kept going through my head.

“Leann.”

As it sank in, I knew that no matter what, from now on I would always be Leann deep down inside.

I went into the bathroom and lubed up the butt plug. It was black and easily 6” long with a ring on the bottom for pulling it back out. I inserted it gently, taking my time and enjoying every inch that slid into me. I gave a little moan as my sphincter closed around the base. I couldn’t believe how full I felt. As I hobbled into the living room where I would have more room to practice walking, I noticed that the plug would tickle my prostate just a little every time I took a step. Whenever I sat down to rest, the ring on the plug would cause it to put even more pressure on my prostate. This had the effect of completely turning me on but it wasn’t enough to give me an orgasm. It was a huge tease. I thought about going ahead and giving myself a release but I wasn’t allowed to touch myself so I just kept practicing. I was walking pretty well in my new shoes, by the time the phone rang again.

“Hello, Leann.” My mistress said when I answered the phone. “How are you doing in those heels? Learned to walk okay in them yet?”

“Yes mistress.” I told her. “Thank you so much for getting them for me.”

“I didn’t get them for you.” She replied. “I’m looking forward to seeing how sexy my little slave girl looks. How’s that plug treating you?”

I explained to her about how the plug felt whenever I walked or sat down.

“Good.” She said. “I didn’t expect that but it makes me happy to hear it. I’m going to have to get you a chastity belt just to make double sure that you don’t touch yourself when it’s in. Have you been touching yourself, Leann?”

“No mistress.” I replied. “It’s been hard to control myself though.”

“Well you just keep controlling yourself. You don’t want to make what I have planned tonight any harder on yourself.”

“What do you mean mistress?” I asked.

“You’ll see.” Was her reply. “Now go into my room and look on the spare bed. There’s another box for you to open.”

I did as instructed and found my self looking at two pairs of leather cuffs.

“The small ones are for your ankles,” she told me, “and the bigger ones are for your wrists. Put them on.”

“Now look at the ceiling.” She said when I had finished. “Do you see the hook I’ve put there?”

“I see it mistress.” I told her.

“Good. When I hang up I want you to get the step ladder out and stand on it. Hook your ankle cuffs together then attach your wrist cuffs to the hook. Allow yourself to hang by your wrists, then, kick the step ladder away so you can’t reach it. Have you got that?”

“Yes mistress.” I said and repeated her instructions back to her.

“Good girl.” She said. “There should also be a gag in the box. I want you to put that on too. I’ll be home very soon and we’ll get started. See you soon, Leann.” She hung up.

It was a large ball gag with a black leather strap that buckled behind the head. I put it on and realized that the gag was so large, that with it in, I couldn’t open my mouth any further. We had never used gags before because I had wanted to be able to tell her when the pain was too much.  I brought out the step ladder and stood on it. It was awkward trying to bend over on it with my heels on, but I finally managed to hook the ankle cuffs together with the small clasps on each cuff. I reached up and attached the wrist cuffs to the hook in the ceiling and, letting my self hang free, I kicked the ladder away.

At first it didn’t seem so bad. None of the pain I had expected came. It was only a few minutes, though, when I started to regret kicking the ladder away. My wrists and shoulders started to ache from the unfamiliar weight of my body. We live in an older house with pretty low ceilings. I tried stretching my legs to see if I could touch the floor and maybe take some of the pressure off, but it was no good. No matter how hard I tried, my feet were still inches away from the floor. It was a half hour before I heard the door open and my mistress walk in, and by that time I was starting to moan from the pain.

“It sounds like my little slave is enjoying herself.” My mistress said as she walked in the room. I looked at her, pleading with my eyes to let me down. She just walked around me, inspecting me. Occasionally she would rub my ass or give my nipples a quick tweak through my lingerie. Suddenly, without another word, she turned and walked out of the room. She returned a few minutes later carrying a large black bag.

“I think it’s time we got started.” She said.

She reached into the bag and pulled out a short length of rope. She looped this between my ankles above where my cuffs were connected and tied it to another hook in the floor that I hadn’t noticed before. She pulled it tight before knotting it, causing my wrists and shoulders to hurt even more. I let out another moan of pain.

“This is so you don’t swing too much while I torture you.” She said, standing up and looking me in the eyes. “I guess it’s time I explained what’s going on. You’ve been my slave for a long time now, but at the same time, you haven’t. You’ve had too much control over what I do to you. Telling me when you’d had enough so I’d stop. I didn’t want to stop. I wanted to hurt you more. To see tears run down your face and listen to you scream. From this day forward, you have no more control. I WILL do as I please and you can beg me to stop all you want. It won’t do you any good. That’s what the gag’s for.”

My eyes grew wide and I began to fight against my bonds. This was more than I had ever wanted. She laughed at me while she watched me struggle.

“Fight it all you want, Leann.” She said as she reached into the bag again. “It won’t help you.” She brought out a long thin cane and bent it, testing it’s flexibility. “This is going to be so much fun.”

At the sight of the cane I stopped trying to escape. My body went limp and my eyes followed it’s every movement in her hands. I was hypnotized with fear of what was coming. She moved around behind me and raised the cane above her head. I closed my eyes tight wishing this to be a bad dream and heard the swish as she brought the cane down hard.

Fire blossomed across my ass and my eyes shot open wide as I screamed long and loud even with the gag in my mouth.

“Thank goodness you have that gag in, Leann.” My mistress told me, laughing. “I think the neighbors down the street would have heard that otherwise.”

She raised the cane again and brought it down even harder. This time she didn’t stop, but kept hitting me over and over. I don’t know how long she caned me; all I remember was the pain in my ass cheeks and the sound of my own muffled screams. When she finally stopped, my body was racked with sobs and there were tears running down my face. The pain I was experiencing faded slightly after a few minutes but didn’t go away entirely. My mistress walked back around to face me, slightly out of breath. When she saw my tears she smiled a wide evil smile. I had never seen her smile like that before. I tried to beg her through the gag to let me go, but all I could do was whimper.

She stared at my face for a long moment then suddenly put her hand down the front of her pants. I watched as she rubbed herself to an immense orgasm. Just as she was about to cum, she reached out with her other hand and grabbed my nipple again, twisting it as hard as she could. I screamed and so did she. I screamed from the pain, and she screamed from pleasure.

She stood there for a minute, panting and staring at me. When she had composed herself enough, she reached back into the bag and brought out a digital camera.

“These are going on the internet so that everyone can see what you are now.” She said as she snapped a few pictures. She walked around behind me again and I felt her lift up my chemise a little, exposing my ass, then she snapped a few more pictures.

“Absolutely beautiful.” She said. She rubbed my sore ass, causing me to whimper as the pain intensified again. “You welt up so wonderfully. Well, shall we continue? We’re far from done.”

She went back to the bag and brought out a leather whip. This wasn’t the usual whip you buy at a bondage shop. This whip only had one purpose: causing pain. It was about two feet long and made of braided leather strips. It had a knot on the end with four or five thin leather strands hanging from it.

Without a word, she walked around behind me, raised the whip, and started in on me again. My screams started anew while she concentrated this time on my back and my legs. Once again I lost track of time but I know the whipping went on longer than when she caned my ass. It was as if she wouldn’t be happy until she had covered every inch of me with welts. Eventually, she must have decided that my ass wasn’t sore enough because she worked her way back to it and stayed there for a long time.

The pain was terrible. I didn’t know that anything could hurt like that. With every blow of the whip, my screams became longer and more frantic and I arched my body away from the blows as much as my bonds would let me. This just seemed to excite my mistress more and she started whipping me faster.

Finally my mistress stopped and I hung there panting for breath. This time the pain didn’t fade at all and I felt each stroke on my body as if it had just happened.

“Oh that was so much fun.” My mistress whispered into my ear. “And we’ve still got so much to do.” I felt her hands gently begin to fondly my sore ass cheeks. “But first, I need to check on this.”

I didn’t realize what she meant at first. I thought she was going to begin whipping me again until she looped her finger through the ring of my butt plug, pulled it partially out, and then rammed it home again, causing me to squeal. She did that three or four more times. For just a moment all thoughts of the pain my body was in were forgotten and I moaned from the feeling.

“We can’t have that right now,” she told me, “can we Leann? Only if you’re a good girl and make me happy.” She went back to the bag. “Right now, it’s time to work on your front.”

She pulled out two pairs of clamps. These weren’t ordinary nipple clamps. They were shaped like pliers, but had a screw on one end for making them tighter. I recognized the vice grips right away and immediately knew where they were going. She raised the front of my chemise up until my nipples were exposed and slowly brought the first pair of vice grips toward my right nipple.

I tried to twist away, but it was no use. Before I realized what was happening, I was screaming again as the clamp bit down on my nipple and was tightened as much as possible by my mistress. Once my mistress was satisfied that the clamp wouldn’t come off, she simply let go, letting gravity pull the clamp down and sending fire through my chest, then attached the other clamp to my left nipple.

I hung there screaming and shaking my body, trying to get the clamps off, but the swinging of the clamps only increased my pain so I force myself to go still. That didn’t really help either. The pain was enormous either way. I finally quit screaming, but couldn’t stop whimpering from the pain, even though I tried to be quiet.

Apparently my mistress didn’t like hearing my screams stop because she reached out, grabbed both clamps, pulled, and twisted, causing my screams to start again. She tortured my nipples for a long time. She would pull one, then the other, then both and I could tell by the look on her eyes as tears poured down my face, that she was loving every second of it.

Finally, she let the clamps go but didn’t take them off. She cranked down on the tightening screw, turning them a few more times then picked up the step ladder. She unbound my ankles and had me stand on the step ladder and unshackle my wrist from the ceiling hook. I was shaking and weak, and as I stepped down from the ladder, my legs gave out and I fell, sprawling to the floor. I hoped she would be satisfied now and stop the torment she was putting my body through but I was wrong.

Laughing, she shackled my hands behind my back and got a longer piece of rope from the bag. She tied the rope to my wrist cuffs then had me stand up. She quickly looped the other end of the rope through the ceiling hook, before I could fall again, and then pulled it until I was bent over with my arms painfully pulled out behind me. Then she tied the loose end of the rope to my cuffs. Now I didn’t dare fall again for fear of what would happen if I did and my shoulders were twisted farther than they were supposed to go. She then reattached my ankle cuffs so that my ankles were bound together and tied them to the hook in the floor so that I could barely move at all.

When I was bound to her satisfaction, she picked up the bag again and moved around where I couldn’t see her. I could hear her moving around behind me, doing something, and when she walked back to where I could see her, she was completely naked except for a large strap on. It was 8” long, thick, and red. My eyes widened at the sight. I had never had anything that large in me before. Even the plug inside me right now had been a new record. I didn’t know what this would be like.

“Now here’s something I’ve been looking forward to giving you for a long time.” My mistress told me. She began to lubricate it slowly and lovingly, as if it was her lover. “I’ve always wanted to rape you, really rape you, but it’s hard to rape the willing. Somehow I don’t think you’re willing anymore, are you?”

I didn’t answer at first. My mind was reeling at the revelations I’d received about my wife since she got home. Angrily she bent down and began pulling on the clamps hanging from my nipples again. She pumped them almost as if she were milking a cow as my screams began again.

“So,” she said after a few minutes, “are you a willing slave?”

I frantically shook my head no.

“Good.” Was her reply.

She walked around behind me and pulled the plug in my ass all the way out, then shoved it back in me hard and kept the pressure on it as if she were trying to force it in me completely. I squealed and tried to pull away to relieve the pressure, but the way I was tied kept me securely in place.

“If this is what this plug can do to you” my mistress said as she pulled it out, “then I can’t wait to see what this strap on does.”

Without another word, she plunge the strap on inside me. She wasn’t gentle or slow with it, instead choosing to force it in me all at once. Thankfully, the plug that had been inside me all day had prepared my hole for this so that I wasn’t as tight as I could have been.

I squealed from the sheer size of the strap on as she started to pump it in and out of me with vigor. Before long my squeals turned into moans as I became overcome with lust. Steadily she pumped it in and out of me, never slowing down, thrusting it in me like an animal. She went on for what seemed like forever until finally, even though it felt so good, I wanted her to stop just to give me a rest.

She didn’t stop, though. She just kept pumping away in me, as hard as possible. I began to try and beg her to stop through the gag in my mouth, but that just made something inside her snap and she raised her hand. She began slapping my ass with ever thrust of her hips, spanking me as hard as she could. The introduction of pain to my already swollen ass trickled through the haze of pure pleasure that was filling me and I became aware that with every slap and thrust she gave me sent the clamps on my nipples swinging wildly and causing even more fire to flash through my body.

The mixture of pain and pleasure began getting to me. I wanted it all to stop. I wanted the clamps off my nipples; I wanted time for the welts that covered my ass, back and legs to disappear. More than anything else, though, I wanted the raping I was receiving to stop. I had never thought that pleasure could become a form of torture but that’s what it was. The strap on in my ass didn’t actually hurt. Quite the opposite. It felt so good that my mind and my body needed time to process it all and my mistress wasn’t about to give me any mercy at all.

It wasn’t long after this realization that I started to feel the build up of an orgasm in my groin. The pain my body was having inflicted upon it kept the build up coming slower than I would have imagined so that I though my orgasm would never come, while the pumping of the strap on inside me kept promising that I would have release. It drove me absolutely wild and I found my self trying to thrust my ass backwards to meet the driving force of her hips.

Finally, when I didn’t think I could take it any longer and I would pass out, my orgasm came in wave after magnificent wave, making me cum harder than I ever had before.

My body went totally limp and my mistress stopped and took a step back to make sure I was still conscious. When she noticed the puddle of cum on the floor between my legs she just smirked and slid the strap on back inside me. She began pumping my ass again and before long I felt the build up in my groin once more. It took much longer for my orgasm to climax but eventually I came again. This time my mistress was ready for it.

Just as my juices were about to spew forth, my mistress stopped and kneeled down beside me. I moaned in disappointment as I felt my orgasm begin to recede without being finished but my mistress took my cock in her hand and began to stroke it, building my orgasm up once more.  She watched me for any sign that I was about to cum, and just as I was on the point of climaxing, would suddenly stop. When she was sure the feeling had faded again, she would start stroking me some more. She did this over and over. She would bring me to the point of orgasm only to stop and let it fade.

I couldn’t believe what I was feeling. This might have been the greatest torture of all. Finally, she didn’t stop but let my orgasm come, sending waves through my body that made me shiver and I let out a primal scream of lust as I came even harder than before.

My mistress caught my juices in her hand and held it up in front of my eyes.

“You’re going to drink this, Leann.” She told me. “I’m going to take your gag out, but if you make one small sound, or refuse to drink any of this, I’m going to put it back in and we are going to start over with the cane. Do you want me to start torturing you again?”

I shook my head no and she unstrapped the gag and took it out of my mouth. My jaw ached from being held open for so long, but before I could enjoy the moment, my mistress took her cum filled hand and held it up to my lips.

I hesitated as the smell of it filled my nostrils but I didn’t want to be tortured anymore. Slowly I lapped my own cum from her hand like a dog from his water bowl and filled my mouth with it. It tasted strange and salty and as I rolled it around on my tongue, I saw the look on my mistress’s face. It was one of pure ecstasy, and I felt something inside me changed. From that moment on, I knew that I would live to see that look on my mistress’s face. I would do anything for her even if it meant taking the same sort of abuse I had received that day. After all, I had always dreamed of being really raped and tortured while dressed as a woman. Now my dream was coming true.

I was Leann, my wife’s slave.

My mistress smiled as I swallowed the cum in my mouth. She took the clamps off my nipples; bringing a pain that I didn’t expect and causing me too scream one more time. She didn’t untie me, but loosened the rope connecting my wrists to the ceiling hook enough so that I could lay down on my stomach. She then put the gag back in my mouth, and the plug back in my ass.

“That was very good, Leann.” My mistress told me as she walked to the door. “I’ve taken the day off tomorrow so we’ll continue then.”

With that she turned off the light and left the room, closing the door behind her, and left me with mixed feelings of euphoria and fear of what was coming.

To Be Continued…