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…

CROSS DRESSER ENSLAVED

A Fictional Account Of A Cross Dresser’s Fantasies

Day 2

       Because of the pain from the torture I had received and the plug inside me, I didn’t sleep well at all that night. Even though she had allowed me to lay down on my stomach, my arms were still pulled back behind me by the rope tied to the ceiling and my shoulders were really hurting. My jaw was also aching from the large ball gag that was in my mouth. Finally, I suppose exhaustion finally took it’s toll, because I fell into an uneasy sleep.

       The next morning my mistress crept quietly into the room and hooked her finger through the loop on the plug.  As hard as she could she pulled the plug out of my ass and rammed it home again. I awoke immediately, moaning long and loud. Apparently, I was still very tender inside from the raping I had received from her the night before, because the feeling was just as intense as it was just before I had cum the second time.

She kept pumping it in and out of me and started to spank my ass. It was still red and covered in welts from the whipping I had received the night before and what had finally faded to a dull ache became red hot fire once more and I started screaming again. When she was satisfied that I was fully awake, she stopped, giving my ass one last swat as she stood up.

“How do you feel this morning Leann?” my mistress asked me.

There was no way I could answer her with the gag in my mouth. The pain I had endured and the frustration of not being able to speak was too much. I began sobbing uncontrollably as tears poured down my face.

“I’m glad to hear that, slut.” She told me, laughing. “I hope you’re ready to continue where we left off.”

She pulled on the rope that ran through the hook in the ceiling to my wrists and pulled me up with it. The pain in my shoulders was immense. I thought my arms would be pulled out of their sockets. Finally, I was in the position that my mistress wanted; bent over, my ankles tied to a hook in the floor, and my wrists tied behind my back with my arms extended and stretched toward the ceiling, bending me over.

She didn’t waste any time but picked up the cane from the night before and began whipping me again, listening to my screams. She was incredibly calm about it unlike the night before when she had been so driven. It was almost as if she were pursuing a hobby like most people would pursue stamp collecting or scrap booking. The whipping went on for a long time using both the cane and the whip, leaving me in so much pain I thought I’d pass out.

Finally, the torture my mistress was enjoying putting me through stopped. She left the room leaving me with tears running down my face and came back a few minutes later with a folding chair and a bowl. She put the bowl to the side and set the chair in front of me.

“Now you’re going to do something for me.” She said, stripping down. She sat down in front of me, took out my gag, and put her legs on my back, causing even more pressure to my sore shoulders and burying my face in her pussy. “Lick, slut!” she commanded.

I did as I was commanded, running my tongue up and down her slit and teasing her clit. It wasn’t long before her moans filled the room and she was grinding her pussy against my face in ecstasy. I licked her pussy as fast as I could, finally concentrating just on her clit and felt her juices spray down my face and into my mouth as she let out a scream of pure lust.

I swallowed her cum while she just sat there, rubbing her pussy on my face slowly and panting as she waited for the glow of her orgasm to fade. Finally, she stood up and put on her strap on.

“That was very good, Leann.” She told me. “I think that deserves a little reward.”

I knew what was coming and realized that I couldn’t wait. Just the thought of that large dildo pumping inside me was making me hard.

“Oh, I almost forgot.” My mistress said and picked up the bowl. She placed it on the floor directly where my cum had landed the night before then walked around behind me. Once again she didn’t bother being gentle. She just yanked the plug out of my ass and shoved her strap on inside me hard. “Let’s try for three orgasms this time with no hands.” She said and started pumping the strap on inside of me.

It didn’t take long for my first orgasm to come. My mistress handled her cock like she had been born with one. With each thrust inside me, I began to feel the build up of what I knew was going to be a wonderful release. Finally my orgasm came. My body shuddered and with a moan of lust my juices shot out and right into the bowl between my legs.

Even though I needed to rest a moment to let the last tremors of my orgasm to work themselves through, my mistress wasn’t about to be that merciful. She knew that before long, the amount of pleasure I was receiving would be too much for me and would just become another form of torture. Soon I would be begging her to stop even for a moment and she was going to enjoy it.

I know that there are a lot of you who are reading this and wondering how something that felt so good could be torture. The only answer I can give you is to allow yourself to have the most wonderful feeling you know to be forced on you non stop for a long, long time. Then maybe you can understand what I mean.

It wasn’t long before I was begging her through my gag to stop. I was so tender inside from the raping I had received last night that it felt like every movement and every thrust of the dildo inside me was magnified ten times over and I didn’t know how much more I could take. My mistress didn’t care, though. She just kept pumping away as hard as she could, laughing whenever I tried to beg for mercy.

I knew that another orgasm would be long in coming since I had climaxed once already, but I didn’t realize how long. I lost all track of time and wasn’t aware of anything but my raping. There was nothing but the feel of the strap on sliding in and out of me. Finally, I felt my orgasm building up again even though it took forever for my climax to come. I thought I would lose my mind by the time I came again. Finally my orgasm came and tremors of pleasure made my body tremble as another moan escaped through my gag.

My mistress still didn’t stop. She just kept thrusting away at my ass. I couldn’t believe that she was still going. Surely she was getting tired by now but she wasn’t showing it. After awhile, through the mind blowing haze of pleasure that had me praying for rest, I began to think that another orgasm was never going to come. Just as I began to think that the fucking would last forever, I felt the build up of my orgasm once more. It must have taken ten times longer to come than my second orgasm, seeming to stay just out of reach of glorious release, but it finally did come. As the last waves of my orgasm flowed through my shaking body, I felt my mistress rip the strap on from my ass and shove the plug back inside me with one fluid movement.

       “I want you to get on your knees.” Was all my mistress said as she picked up the bowl between my legs and loosened the rope that bound my wrists to the ceiling. As she gave the rope more slack, I levered myself onto my weak, trembling knees and she came around in front of me and sat once more in the chair directly in front of me holding the bowl. She sat there a few minutes, obviously out of breath. As I looked at her, I noticed that her legs were trembling almost as much as mine.

       Finally, she leaned forward and took the ball gag out of my mouth. “Open.” She said as I tried to work the ache from my jaw. Knowing what she was going to do, I opened my mouth wide and tilted my head back slightly as the put the bowl with my cum in it to my lips and emptied it into my mouth. The smell of my own cum filled my nostrils as the salty taste of it washed over my tongue. We sat in this position until every drop that would come out went into my mouth. “Swallow.” She said as she put the bowl down. I did as commanded and felt my cum sliding down my throat.

       She leaned over and lifted my chemise exposing my nipples. She pinched my nipples with her fingers, tugging and twisting them gently. Not enough to cause me to cry in pain, but enough to know that the pressure could be increased any moment. “I’m going to untie you now, Leann.” She told me as she kneaded my nipples, a slight smile on her face. “We’re going to begin the next part of your training. You’re going to learn how to act like a woman. You’re going to learn to apply make up to your face, and how to walk and move like a woman. You will not speak. You will only listen to my commands and obey them. Tonight, we are going to go out and you are going to show me how much you’ve learned.” I nodded my head to show that I understood, and she moved behind me and untied the ropes that bound my wrists and ankles. After having the ropes digging into my skin since yesterday evening, it actually hurt when the ropes came off. Soon the pain in my wrist and ankles faded but I noticed, as I followed my mistress into the living room, that even the slightest movement caused the welts that covered my body to flare into pain. It was as if they didn’t want me to forget that they were there.

       Over the next several hours my mistress taught me everything she could about acting like a girl. When ever I made a mistake, she used the cane or the whip to correct me. She showed me how to walk and carry myself feminine. Everything from the slightest arm movements to the way I should move my ass as I walked. I concentrated on her every command and found that some things were starting to come naturally surprisingly fast. Next we moved into the bathroom and I learned how to put on make up. I learned how to put on everything from foundation and blush, to mascara and lipstick.

       “Okay Leann,” my mistress finally told me, “that was very good. Now I want you to take out the plug and take a shower. After that we’re going to get dressed up and go out. Just a couple of girls enjoying a night out on the town.” She turned to leave as I slid the plug out of my ass then turned back as if she forgot something. “Oh, and don’t forget to shave your body again. I want you perfectly smooth tonight.” She told me then walked out.

       I bathed and shaved myself as directed even though it was extremely painful when I got to the areas of my body that had been tortured. When I had finished drying off, I walked out of the bathroom to find my mistress. As I walked toward the bedroom I though how odd it was that when I thought of my wife, the first word that came to my mind was “Mistress”. In just two days I had stopped thinking of her as my spouse and started thinking of her as my owner.

       When I walked into the bedroom, I saw my black spaghetti strap dress laid out on the bed. Next to it was a garter belt, stockings, and another pair of heels exactly like I had been wearing earlier except black to match my dress. My mistress told me to put on the everything but the dress which I did with enthusiasm. Women’s clothing was already beginning to feel more natural than anything else I had worn as a man. Next my mistress had me sit in front of a mirror while she gave my short hair a style that was more feminine.

       “Luckily a lot of women have short hair,” she told me, “but from this day forward you’re not to cut your hair. You’re going to let it grow long so it’s more lady like.”

       When she was finished she instructed me to put on my make up by myself while she watched to make sure I had learned exactly how to do it. As I began, I saw my mistress’s eyes narrow when I almost forgot the concealer, and quickly fixed my mistake before she decided to punish me for it.

       When I finished with my make up, my mistress had me put on the dress and look at myself, complete, in the mirror. I almost didn’t recognize myself. I was used to seeing myself as a man but looking back at me from the mirror was a petite, pretty (if I do say so myself) young woman. Granted I was a little flat chested for a woman but I was still very passable. My dress was just a little tight and hung from my shoulders from it’s two thin straps down to my mid thigh. I had always had an almost feminine body and my natural curves were actually enhanced by the tightness of my dress.

       My mistress shook her head as she looked at me in the mirror. “I can’t believe how well you turned out.” She told me. “You look more like a girl than I would have thought. I actually think you look better like this than as a man.”

       “Thank you, mistress.” I told her blushing.

       “You’re welcome, Leann.” She replied. “Now go in the living room and practice what I taught you until I’m ready.”

       I did as instructed until she came out dressed stunningly in a slinky little red dress of her own.

       “Here, you’ll need this.” She said, handing me a small black purse. “I’ve already put your driver’s license in there just in case you need it. Are you ready?”

       I was about to say yes when I realized exactly what I was about to do. Dressing as a woman around the house was one thing, but going out in public was something else completely. My mistress must have seen the look on my face because she just laughed and, grabbing my arm, led me out the door. As we walked to the car I realized something.

       “Mistress,” I said, “I’m not wearing any panties.”

       “You’re not allowed to wear panties right now.” She told me as she unlocked my door. “Your cock has never been very large so I don’t think you have to worry about showing a bulge but you’d better sit so that people can’t see up your dress.” She opened the door for me and I got into the car. A moment later she slid into the driver’s seat, turned the key in the ignition, and put the car in gear.

       “This is going to be so much fun.” She said as she pulled out of the driveway.

       First we stopped by my mistress’s favorite restaurant, The Victorian Grill, and ate dinner. I was a nervous wreck by the time we got to our table. Even though it was just my imagination, I felt like everyone was staring at me as if they could see right through my dress to what I was underneath. I was so nervous; I couldn’t even read the menu. I just sat there staring at it like an idiot. I looked over at my mistress, hoping for some reassurance, but she just looked over her menu with a smug smile on her face. When our waiter suddenly came over to take bring us some water and take our orders, it was all I could do not to jump out of my skin.

       “Hi. My name is Daniel.” He said. “I’ll be your server tonight. May I take your orders, ladies?”

       “I’ll just have a salad with non-fat ranch dressing.” My mistress replied.

       “And what about you m’am?” Our waiter said.

       I looked up at him for the first time to tell him I would have the same thing and looked into the deepest blue eyes I had ever seen. He was tall, easily six feet, with short blond hair. He wasn’t so much muscular as very well toned and his white uniform shirt was just tight enough to enhance his physique. In short, he was a dream on legs.

       “I-I’ll have the same.” I stammered. I couldn’t help noticing as he walked away, how tight his nicely rounded ass was. My mistress didn’t miss me looking at him either.

       “Mmmm. You like him, Leann?” she asked. “He is pretty yummy. I wonder how you would look with his cock in your mouth.” I just blushed and reached for my water but I had to admit, it was an intriguing idea. He came back a few minutes later with our salads and set them down in front of us.

       “If there’s anything at all that I can do for you ladies,” he said leaning over slightly and looking me straight in the eyes, “you just let me know.” I could have happily gotten lost in those big blue eyes forever. I couldn’t even reply. I just nodded my head and gave him a little smile.

       “Wow, Leann.” My mistress said when he had gotten out of ear shot. “Do you realize that he was actually flirting with you? And you actually flirted back a little.” She shook her head and smiled. “You’re first night out as a girl and you’re already acting like a little slut.”

       My stomach did a flip as I realized that she was right. He had been flirting with me. I suddenly felt very good about myself. I hadn’t meant to flirt back though, not even a little. I just picked up my fork and forced myself to eat even though I wasn’t very hungry while my mistress laughed quietly to herself.

       We finished our salads and Daniel brought the check over.

       “What time do you get off, hon?” My mistress asked as she handed him her credit card. My stomach did a flip and I stared at my mistress. What was she doing?

       “In about a half hour.” He replied.

       “Well, Leann and I are about to head over to Club Danza in a little while. If you like, you can meet us over there later.” I couldn’t believe my ears. My mistress nudged me. “Does that sound like a good idea, Leann?”

       I looked back up at our waiter, panic rising within me. “That sounds wonderful.” I told him. I couldn’t believe how lame I sounded. “We’d love to see you there.”

       “Well maybe I will then.” He replied. “It was very nice meeting you Leann.”

       “You too, Daniel.” I told him as he left. “What are you doing, mistress?” I asked.

       “Oh just having a little fun, Leann.” She told me. “And don’t you question anything I do from now on. Understand?”

       “Yes mistress.” I replied, hanging my head. I knew I was going to pay for my little outburst later.

       We left and my mistress drove us to the club she had told Daniel we’d be at. I had thought she was just messing around. What if Daniel actually showed up? What was she expecting me to do?

       We went inside and there was a nervous moment when I showed the door man my ID. He just looked at me for a sec, rolled his eyes, and let me through. The music was so loud that if felt like you were walking into a wall. The room was dark except for black lights hung all over and the strobe lights on the dance floor. The floor was packed with people dancing and having a good time. We made our way through the crowd of people and found a table near the dance floor where we had a good view of the dancing. I got us a couple of drinks and settled down to enjoy the music and watch the dancing. I lost all track of time as I sat there drinking and trying to get used to being dressed in public. It might have been the alcohol, but I found myself becoming more comfortable as time went on.

       As I sat there enjoying the buzz that was running through my body, I felt someone put their hand on my shoulder and looked up to see who it was. I was surprised to find myself looking into the gorgeous blue eyes of our waiter from the restaurant.

       “Hi.” Daniel said. “Mind if I join you ladies?”

       Wide eyed I looked over at my mistress who just smirked and nodded her head. “Sure.” I told Daniel and he took a seat next to me. The three of us talked for awhile, having to practically scream to be heard over the music, until Daniel looked over at me and asked me too dance.

       “No thank you.” I told him. “I’m not a very good dancer.”

       “Oh go on, Leann.” My mistress said. “Let loose and have a little fun.”

       Taking the hint and getting up, I followed Daniel onto the floor. Every now and then I would practice dancing like a woman in front of a mirror and I was suddenly glad. We danced for a long time and I found myself enjoying it more and more with each song. Finally, we were about to go have a seat when the DJ decided to put on a slow song. I froze up for just a second as Daniel put his hands around my waist and pulled me in close. I got control of myself and nervously snaked my arms around his neck.

       “I can’t believe how pretty you are.” Daniel told me as we danced. “I don’t meet too many women like you.”

       “I bet you don’t.” I said, thinking of what was hiding under my dress. “I’m glad you came here tonight, though.”

       “Me too.” He said and I found myself laying my head on his shoulder as we danced.

       All too soon the music was over and we made our back to the table.

       “Why don’t you get us some more drinks, Leann.” My mistress said as I was about to sit down. When I came back I noticed that Daniel was gone.

       “Where’s Daniel?” I asked, sitting down.

       “He went to the bathroom.” My mistress told me. “He’ll be right back. By the way, you looked so cute out there with him. Especially when you had you head on his shoulder.” She shot me one of those smiles she gave me when she was torturing me. “Very slutty. I can’t wait to get you home and show you what happens to little teasing sluts like you.”

       I found myself both scared of the punishment I knew I was going to receive and blushing at the thought of dancing with Daniel. I liked being pressed close to him.

       “Oh, and Leann,” my mistress said, “just to let you know, I told him all about us.”

       Suddenly I began to panic. “Everything?” I asked her.

       “Everything.” She replied. “He seemed to like the idea.”

       “Really?” I was surprised.

       “That’s right.” She told me. “From now on, what ever he tries to do, you let him. He can touch you however he wants. Just don’t let him take you somewhere and try to have sex. Other than that, anything goes.”

       A few minutes later, Daniel came back and sat down. He moved his chair right up next to mine and put his hand on my knee. “So,” he said, “your mistress was telling me all about you.” He began to move his hand up my leg, gently stroking my thigh. “Just sit still and let me find out for myself.” His hand went inside my dress and I felt him fondling my small cock which became hard almost immediately. “So it is true. That’s a nice clit. Very, very sexy.” To my disappointment, he took his hand out of my dress, but put his hand behind my head, and drew me in close for a kiss.

       He kissed me once, twice, three times, then I felt him flick his tongue across my lips and I opened my mouth wide to admit him. As we sat there french kissing, our tongues entwining and exploring each others mouths in the most intimate of kisses, I found myself thinking of what it would be like to spend the night in Daniels arms. We continued kissing for a long time but not nearly long enough for me. All too soon I felt Daniel pull away and looked into his smiling face. “That was wonderful, Leann.” He told me. I had to agree.

       The three of us spent the next couple of hours chatting with the occasional pause for Daniel and I to dance or make out some more. Daniel was very interested to hear about our lifestyle and was surprised to find out that this was only my second night of being a woman. He especially liked hearing about what my mistress would do to me and once, I quickly lifted up the back of my dress so he could see the whip marks covering my ass. Occasionally he would put his hand back up my skirt as he listened and fondle my small “clit” as he called it. As much as I wanted him to, he wouldn’t stroke it or do anything that might cause me to cum. He would just sit there and feel it lightly with his fingers.

       Eventually my mistress looked at her watch. “It’s getting late.” She said to my disappointment. I was enjoying myself. “Leann, it’s about time we headed home.”

       “Yes mistress.” I told her and turned to Daniel. “I had a wonderful time, Daniel.” I told him. “I hope we can do this again sometime.”

       “Me too, Leann.” He replied. “How about giving me your number and I can call you sometime. If it’s alright with your mistress, that is.”

       I looked over at my mistress and was surprised when she nodded her head. I wrote my phone number down on a napkin and gave it to him.

       “Great, thanks.” He said. “You ladies take care now.” With that he gave me one last deep kiss, and winking, walked away.

       “My goodness, Leann.” My mistress said when we got back to the car. “You are something else. That first kiss was amazing. I could tell you were really into it. I had no idea how much of a slut you really were. Letting him put his hand up your dress like that.” I blushed deep red but I knew that my mistress was right. I may have just been following her orders, but I enjoyed every minute of it. When it came to my new lifestyle, I was definitely a slut. “I can’t wait to get you home. Tonight’s session is going to make the others look like a kiddie ride.”

       When we got home she immediately had me take off my dress, leaving me clad only in my garter belt, stockings, and heels, and had me go back into my new room and assume the familiar position of being bent over with my hands tied behind my back attached to the ceiling hook, and my ankles tied together and tethered to the floor hook, and the ball gag in my mouth. She stood in front of me where I could see her and stripped totally naked. She picked up her strap on and started to buckle it on.

       “Don’t worry, Leann.” She told me. “I’m not always going to tie you up like this. I’ve been doing some online shopping for bondage furniture to put in here so that I can put you in different positions. Before long we’ll have this room totally converted to a torture chamber just for you. Won’t that be nice?”

       She picked up the cane and the whip, looking at them as if deciding which one she wanted to start with. Finally she put down the whip and, with cane in hand, moved around behind me. I tensed for the pain I knew was about to come but suddenly the doorbell rang.

       “Now who could possibly be dropping by at this hour?” My mistress asked. Still holding the cane and naked except for her strap on, she walked out of the room. Was she going to answer the door like that? A minute later I heard voices coming from the living room. Who could she possibly be talking too? A few minutes later she walked back into the room. I was more surprised by what I saw than I had been by anything else so far.

       As she walked into the room, she was followed by Daniel. He was completely naked, his manhood hanging out for the world to see, and he was carrying a large wooden paddle. He stopped, smiling from ear to ear, and surveyed the scene in front of him. As he stared at me, tied up and helpless, I watched his erection grow. Completely erect, he was as large as my mistress’s strap on. My eyes widened and I frantically looked back and forth between my mistress and the prime example of manhood that was Daniel. I didn’t understand what was going on.

       “I can see in your eyes, Leann, that you’re confused.” My mistress told me. “Let me explain.” She told me how Daniel had been a friend of hers since high school and how he had always liked cross dressers. He also liked bondage and S&M and had a real cruel streak in him. Maybe even worse than hers. When my mistress made the decision to turn me into her slave girl, she immediately called up Daniel and asked if he would like to take part in my enslavement. Of course, he immediately jumped at the chance, and well, here we were.

       While my mistress explained, Daniel walked over and gently rubbed his erection all over my face, never saying a word or losing his smile. When my mistress had finished talking, Daniel walked around behind me and stood there rubbing my ass cheeks for awhile.

       “This is going to be fun.” I heard him say just before the swish of the paddle flying through the air filled the room.

To Be Continued…