tagTranssexuals & CrossdressersWhen Curiosity Fills

When Curiosity Fills


I sat in alone in my office at 11:00 p.m. on a Thursday night in April, preparing an important motion in a multi-million dollar malpractice suit. After editing the final draft I sat back and took a deep breath. I was exhausted, and, oddly enough, pretty horny. The wife was out of town and somehow I couldn't stand the thought of spending the night with just my hand. Shaking off the sordid thoughts that were roaming through my head, I stood up and began the walk down the empty hallway to my secretary's office. I dropped the motion on her desk and headed for the elevator.

I was a little shocked to see one of the nerdy kids from IT standing in the atrium with two laptops in one hand and a large open top briefcase in the other. I nodded hello and we made some stupid small talk about the new laptops the firm was buying. The elevator came and we both went to step in at the same time, bumping each other slightly. In an effort to avoid dropping the laptops, he let go of his briefcase spilling its contents into the elevator. As I bent down to pick them up I was shocked to see a copy of the LAXpress, a local paper notable only for its extensive escort advertising. The paper was folded open to a page full of adds, but one particular add caught my eye. It read "Sexy TS Mistress Waiting for Your Call." Below was a picture of an incredibly gorgeous woman , "Miss K", and a phone number. I stumbled for a second and then pushed all of the papers back into his briefcase. There was an uncomfortable silence on the remainder of the ride down. I am sure he was wondering whether or not I had seen his paper. I however, could not get my mind off of the goddess I just saw. Her phone number was stuck in my head. The whole ride home my mind was running through a hundred different fantasies. I knew what the "TS" meant in the add, and although I had never even considered the option, now all I could do was envision myself looking down at that gorgeous woman as she performed all kinds of sordid acts on me.

When I got home, I figured I better get my mind off of Miss K and back into the real world. I called my wife and chatted for a few minutes before she begged to go back to sleep. There I was, sitting on the couch with a phone in my hand and a phone number racing in my head. Honestly, I thought "maybe I will just call her, listen to her voice, satisfy myself, and then go to sleep." No harm no foul. So I made the call. An incredibly sexy voice answered the phone. Somehow I was surprised at how feminine her voice was. Feminine yet firm. She had to say hello twice before I could respond.

"Hi, may I speak to Miss K please?"

"This is she. . . who is this?"

"My name is Joshua" I couldn't believe I gave her my real name and started to hang up, but I couldn't force myself to take my ear from the phone. So I just sat there, my cock in my hand. A few seconds ticked by and then from the other end I heard, "Joshua, I know you are thinking about rubbing that cock of yours tonight. . . don't. It is now exactly midnight. For the next 24 hours, I own you. You will do exactly what I say."

I responded, "you know that is not really what I am into, but . . ." She cut me off, "Don't ever speak to me again unless I ask you a question."

I thought about hanging up, but something about the way she spoke to me, firm, yet there was something very comforting in her voice.

"Here are the rules. You address me as Mistress. Under no circumstances are you to bring yourself to orgasm before midnight tomorrow night. You will call me at 1:00p.m. tomorrow. One minute late and you will never talk to me again. Do you understand?"

All I could muster was a weak "yes.

"Yes. . . what?"

I responded before I could think "yes Mistress."

The line went dead.

Needless to say, I was incredibly turned on. Of course there was no way I was going to call her tomorrow, but it was one hell of a fantasy. I turned on some straight porn and proceeded to rub myself. Somehow, though, I just couldn't get Miss K out of my head. I don't know why, but I went to sleep without finishing.

The next morning I woke up late and rushed to get ready and ran out the door. When I got to the office there was one catastrophe after another and I spent the whole morning putting fires out. A little after noon, everything died down and I finally sat down at my desk. Miss K crept into my mind. I felt that familiar stirring in my pants. I picked up the phone, and called my wife. When she answered, we talked for a while. Suddenly I found myself making up a lie. I told her that I was going to a client meeting in Orange County and that I was going to try and catch a movie afterward. Before we hung up, I told her that I would try to call her tonight, but that if the movie got out too late, I would call her tomorrow. We said our goodbyes and hung up.

I sat there in awe of myself. I had just made up an excuse for being out of touch until tomorrow morning. Why? It was just a fantasy. I wasn't going to call her. I looked at the clock. . . it was 2 minutes to 1:00. A wave of panic ran through me. Almost instinctively I reached for the phone. Ok, let's let the fantasy go a little further. After all, what would it hurt? I picked up the phone and dialed. She answered in one ring, "Don't say a word Joshua. Be at my house in 45 minutes. Bring one thousand dollars. If you are one minute late, the door will be locked." She gave me her address in a luxury apartment building in West LA and hung up. I was hard as a rock. I had to take the next step. I had to see this woman. Maybe I would just pay for a blowjob or something and then leave. I looked down at the clock. . . I only had 30 minutes. I picked up my briefcase told my secretary that I was going to meet a client and left. I was flying down the freeway and pulled in front of her building with 8 minutest to spare. I valeted the car and walked briskly into the building. She was on the 18th floor.

Standing outside her door, I was shaking. I couldn't believe where I was. My curiosity, and that constant erection between my legs, had brought me too far. I thought briefly about how much money I had. . . 12 . . . maybe 13 hundred. I knocked. As if she was knew I was there, the door swung open immediately. We stood there for what seemed like eternity. She was amazing. Not just sexy. Many women are sexy. She exuded a confident sexuality and elegance that honestly took my breath away. She stood before me in 4 inch heals, black thigh high stockings that ran up and under a tight, yet elegant, black leather skirt. Her top was a tight, yet conservative, red spaghetti strap number that revealed a hint of her gorgeous breasts. She stood about 5'9" in her heals and had reddish hair with green eyes. I was entranced.

As I gained my composure, I took a step back . I had gotten myself in too far. I knew I would do whatever this Venus asked of me, and that scared me.

I started to turn, saying "I'm sorry. . ." But before I finished, she slapped me firmly across the face.

"You already forgot the rules. . . that will cost you." Then she turned and walked into the apartment. "Shut and lock the door, Joshua" Something about the way she said Joshua. Like you would speak to your dog when he was in trouble. Not mean, but demanding obedience.

I whispered, "Yes Mistress."

I walked into a lavish, yet tastefully decorated, apartment. She proceeded into the bedroom, the centerpiece of which was a massive rod-iron canopy bed. Proceeding into the bathroom, she announced "I have an appointment at 2:30. . . that means you have a lot of work to do in very little time."

She pulled a small key out of her pocket, walked over to a large chest that sat at one end of her large bathroom and unlocked it. She lifted the lid and said "Take all of your clothes off and place them in here." I don't know why, but I did as I was told.

When all of my clothes were inside the trunk, she reached into my pant pocket, pulled out my ID, closed the lid and locked it.

Inside, I started to panic a little. I knew I could get the key away from her if I wanted to, but something about standing there in the nude with my clothes locked in a trunk sounded several alarms in my head. It also made me incredibly excited.

She looked up at me and, with a coy smile on her face, dropped down to her knees grabbing my cock firmly. The alarms were silenced. She looked up at me with incredible green eyes and slowly lowered her head, her mouth slightly open. A wave of warm anticipation came over me as I waited to feel her wet mouth engulf me. But the feeling never came.

Instead, I heard a soft click and she stood up. She gave me a soft kiss on the lips and said "Wait here, I will be right back."

About a minute later, she walked back into the bathroom and stood before me. "Kneel down." Eager to get back into the position we had just left, I knelt quickly. She walked around behind me and opened up a small chest. I couldn't see what was in it, but as she came around behind me, she wrapped a soft leather restraints around both of my ankles. Next she pulled both my arms behind my back and wrapped the same restraints around my wrists. Then I heard a sharp click. That click sent me back into reality, she had just hog tied me. I started to explain to her that this was not really my thing. As I opened my mouth, she was there, pulling my head back and kissing me slowly and deeply. She was pure sex. My body relaxed. As it did, she slipped a soft ball into my mouth in place of her tongue. By the time I thought to protest, she had tied the silk ties behind my head, gagging me.

She stepped in front of me and her whole demeanor changed. "I am not sure you understood me when I said that you were mine until midnight tonight. Let me make myself clear. You are mine. You will do anything and everything I say and you will do it without question. I will not ask twice and you will not get a second chance. You will respond to me only with 'Yes Mistress' and 'No Mistress'"

She continued "if you disobey me, this picture will be sent to your wife and to your office." She turned, pressed button on a remote control, and an LCD screen over her bathtub came on. There I was, nude with a gorgeous girl kneeling before me. The look on my face of absolute pleasure was unmistakable. I panicked and tried to stand up. It was impossible. I tried to speak. . . not a chance. Finally I looked up at her.

"Your phone number is 555-4236, your office is 555-8129." Next she rattled off both my home and office address. "I have emailed your name, phone numbers, and this picture to a very good friend of mine with instructions to send the picture if she doesn't hear from me by 1:00a.m." She paused, then, as if reading my mind, said "don't think you can force me to make the call sweetie, we have a code word that I must give her to call off the transaction and you will never know whether I gave her the right one or not. Trust me, you can't outsmart me on this. I will always be one step ahead of you."

She stood there looking at me with a deviant smile on her face. "I have six appointments tonight. That is too much work for one woman to do alone. That is why I chose you. You will be my assistant. I will not hurt you unless you make me. I think you are gorgeous, and I know you will serve me well."

She walked around behind me and whispered in my ear. "This could be the greatest night of your life, or it could be the worst. It is up to you." I heard a click and the tension on my restraints was released. She left the restraints on, but removed the connecting chain. Then she untied the gag and pulled it gently out of my mouth.

My heart was pounding. . . my mind racing through all the possible ways I could get out of this mess. But they all ended up with one of three unacceptable results; jail, fired and divorced, or obedience. For now, I would accept the last of the three evils.

Suddenly, my thought were interrupted as she opened the clear glass shower door, reached in and turned the shower on. Facing away from me, she began to undress. First, pulling her tight skirt down over her hips and letting it fall to the floor, revealing a sexy red g-string and a smooth tight ass like none I had ever seen. As she stepped out of the skirt, she turned to look at me.

"Joshua, I know you are new to this, but please don't let my $500 skirt sit on the bathroom floor."

"Yes Mistress" I muttered. This might not be so bad. I started to get up move over to her when I got a sudden firm slap across the fact. As I looked up at her, she stared at me firmly, "Never stand before me. You may stand to follow my orders. Otherwise, you will always be kneeling."

"Yes Mistress"

I took the skirt and folded it over the arm of the bathroom loveseat. Next, she stepped out of her stiletto heels. I took them with care and placed them next to the loveseat. She pulled straps of the red top down and began to slide the whole top down, over her hips and let it drop. I caught it before it reached the floor. "Very good" she said, leaning down and kissing me on the forehead. Presenting me with her incredibly natural 36C breasts. "You are a quick learner."

Next, she turned and faced me. "Take off my stockings please Joshua." Who was I to argue. I carefully unclipped each of the stockings from her garter then rolled them carefully down her long legs. As I ran them past her feet, I couldn't help but notice how small and delicate they seemed. Perfectly manicured with deep red polish. I laid the stockings on the small table next to the loveseat.

"Finish the job please." I looked up to see that all that was left was the garter belt and her panties. Using a little discretion, I first removed the garter belt, laying it next to the stockings.

I turned toward her again. I felt short of breath. I knew what I would find beneath those panties, but I just couldn't imagine how it could be in there. Part of me hoped that it wasn't. . . only part of me.

Apparently I waited too long. She grabbed me by the hair and forced my head back. She bent down and got right in my face; "I am a very busy woman. I do not have time for you to sit and think about what you must do. You do not have a choice about what you will be doing tonight, the only choice you have is whether it will hurt or not." She flung my head back, reached down and slid her panties off. As she stood up I found myself face to face with a soft, cut, perfectly shaven, 6 1/2 inch cock that was incredibly thick. I gasped.

She grabbed my hair and backed me up to the loveseat, sitting my back on my heals and pinning the back of my head against the padded edge. Still holding me firmly by the hair, she stared me straight in the eyes; "I told you I have a 2:00 appointment and I will not keep him waiting. You see, he likes to think of me as all girl, never wants to see my little cock. The problem is that he is very attractive and it would not be very ladylike to get an erection while he is fucking me. Do you understand?"

I stumbled "Yes Mistress"

"I don't think you do." She retorted. "Open your mouth."

I thought about fighting her off. This is not what I had in mind. I did not come here to suck a cock. I wasn't a fag. Then, out of nowhere, she slapped me firmly. "Are we having a hard time understanding the rules." She squeezed my lips together and I opened my mouth.

"Much better." She said as she straightened herself, resting her soft flesh of her cock on my bottom lip.

I closed my eyes.

In it came, Dry at first, pulling on my lips. She shoved it in firmly saying "I better not feel those teeth." I opened wide to avoid her tearing my lips and curled my lips around my teeth to avoid contact with her soft flesh. She sensed my mouth opening and shoved herself in deep. Her head hit the back of my throat, causing me to gag. She stopped, holding my head tight and leaving her cock bulging in my mouth. My mouth started to water as she pulled out slightly.

"Much better. . . keep it nice and wet." She slid herself back in, this time even deeper, causing me to gag again. She laughed as she pulled it out slightly again. By now, her cock was solid and was filling my mouth. I could barely breath.

"Do you taste that salty flavor" she asked. "That is cum. . . I know it is your first taste, but it will not be your last."

I almost threw up. The thought of having semen in my mouth was almost too much for me to bare. I debated the consequences of throwing her off of me and they almost seemed worth it. But before I could think any further, she shoved her cock back into my throat. Deep this time, letting it rest there for a second as my throat spasmed. She pulled it out. . . then forced it back in. . . beginning a rhythmic movement. I couldn't believe this was happening. Tears were coming from my eyes. Her speed increased and all I could do was relax my throat as best I could. She began fucking my mouth forcefully. I tried to breath between each thrust. I could taste her salty pre-cum in the back of my throat. I tried not to think about it.

Suddenly, her body became rigid and her cock stiffened, the head swelling inside my throat. She stopped her movement abruptly but left her cock deep in my throat. Somehow, in my mind, I thought she was going to pull out. . . that she wouldn't do what I knew was inevitable. That hope collapsed when I felt the first twitch. Nothing came out, but I knew what was next. I wanted to pull away, but she had me pinned to the loveseat. I had no leverage. Then it happened. The first wave was small. Her cock was so far in the back of my throat, I could only feel it. It thrust out of the tip and streamed against my throat. I felt if slide quickly down, heading toward my stomach. When her cock spasmed in my throat that third time, I felt warm cum flood the back of my throat. I could sense it splashing off the back of my throat. Most of it followed the first wave down, but there was too much and some spilled out into my mouth. That is when I got my first true taste of her. It was slightly salty, but that was not the defining characteristic. It was the way her cum made the back of my tongue tighten and curl when it came rushing up around it. I couldn't breath, so I swallowed. The next several waves were a blur as I felt my throat being coated . . . my stomach being filled. . . my mouth being overwhelmed. My head lightened and my body weakened. I heard a soft, almost loving voice whisper "swallow it all Joshua. . . don't leave a drop." In my daze, I did what I was told.

After what seemed like an eternity, the pressure in my mouth slackened and she slowly withdrew. As the head of her now soft cock slid past my lips, I opened my eyes. She was staring at me. She bent down, kissed me softly on the lips and said "Good boy." Then she stood upright, turned and reached in to test the water in the shower. "Come with me boy, I must be clean for my next appointment." I followed her into the huge shower, her aroma still filling my nose and mouth. I knelt before her. Before she entered the water, she turned to face me. I noticed a large drop of cum glistening on the head of her now soft cock, seconds away from dripping to the shower floor. The look in her eyes told me what I had to do. Quickly, I leaned forward, stuck out my tongue and gently sucked the last remaining juice from her. She patted me softly on the head. My emotions were so conflicted. I felt proud, yet disgusted.

"Begin with my back, boy. You may stand. Use the Milk Body Wash and the white sponge. Do not touch me with your hands."

I took the body wash, poured it into the sponge and began washing her back. With great care, I scrubbed her softly, moving slowly down to her incredible round ass then down her long legs. When I reached her feet, she turned and I began my way back up again, lathering her thoroughly as she rubbed shampoo in her hair. Finally I reached her breast which I washed with slow, soft circular strokes. Despite my prior humiliation, I found myself growing once again. She held out one arm at a time and I scrubbed them well. When I was finished, she turned and bent over. "Now wash my pussy well" she said. I complied, amazed at how clean and smooth her "pussy" was.

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bychasen© 12 comments/ 182332 views/ 60 favorites

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