Cross Dresser Enslaved

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…