CAUGHT, Part 2-Training

The next Thursday evening I was promptly on her doorstep at 7 PM. She opened the door with "It’s about time you little sissy. Now get over to the couch and sit down and be quiet."

"Yes Mistress." I replied and immediately went over to the couch and sat down while she closed the front door and followed me into the living room. She sat in a chair opposite me and just stared at me for a time. Finally she began to address me.

"First off my sissy you must learn to sit properly. You seem to think you are a man the way you sit but that is so far from the truth as to be laughable. From now on, you sit with your legs crossed knee-over-knee, your back straight and pushed back to the back of the chair or couch you are sitting in. Next, I expect you to demurely cross your hands over your knees and look attentively at me when sitting in my presence. Never take your eyes off of me when I am in the room. You wouldn’t want to miss something would you?"

"No Mistress, I would not." I replied as I shifted myself to sit as she had instructed me to. Evidently I did it right for she smiled and sat back in her chair. She took out a cigarette and lit it.

"I left my drink in the kitchen. Go get it for me."

I immediately got up and went out to the kitchen to fetch her drink. I noticed it was in a pretty messy state but did not linger over that. I found the drink and took it back to her. I sat back down and she nodded to me.

"You were adequate last week. It is clear you will need a great deal of training to become truly useful as my servant. You do show promise, which makes it worth my time to train you properly.

"To begin with, after you came back with my drink, you sat down. I don’t recall saying you could do that. In the future, ask.

"Next, from now on, when you arrive here, you will go directly upstairs to my room. Against the wall next to the closet there will be a trunk. You will stand in front of it, take off all of your clothes, fold them neatly and lay them on the floor beside the trunk. Then stand there, facing towards the trunk, until I can get to you. Clear?"

"Yes Mistress, very clear."

"Good. Then get your little, sissy ass upstairs and undress."

I immediately got up and went upstairs to her bedroom. As she had said, the trunk was on the floor by the closet door. It was a standard trunk with a locking mechanism on the front. I first took off my shoes and socks carefully rolling and placing a sock in each shoe. Then I took off my pants and folded them and placed them on top of the shoes. After that I took off my shirt and folded it and placed it on my pants. Finally I slipped off my underpants and laid them on top of the small pile. By then I was developing a weak hard on and as I stood up I could see it pointing to the wall which only seemed to excite me more. I briefly rubbed and stroked myself with my hand then stood at attention waiting for her entrance.

After ten minutes’ wait, I heard her coming up the stairs. From the corner of my eye I saw her enter the room and before I could even think about it, she was beside me and suddenly she smacked me soundly on my butt with the palm of her hand. It stung mightily and I started. My hard-on wilted immediately.

"Just want you to remember who is in charge here. I just know you were playing with yourself while I was downstairs. If there is any pleasure to be had, it’ll be mine-not yours!"

She went over to a chair and sat down. "Alright, in front of you is a trunk and it contains your ‘things.’ Each time you come here, you will be going to it, stripping down and standing in front of it waiting for me.

"Now, squat down and open the trunk."

I did as she ordered and the first thing I noticed was taped to the underside of the top was one of the pictures she had taken of me while I was tied up in her bed the week before. It sort of turned me on again to see myself spread-eagled on the bed in her lingerie.

"The picture is to remind you that I own you. Remember, there are two others…Somewhere!"

I nodded and gave her my "Yes Mistress." response. Then I noticed some of the things laying in the trunk. There were a number of lacy panties and bras in both white and black. I saw a few packages of hose and thought there were some garter belts too. I could also make out some kind of dress in a black satin fabric trimmed in white lace. Beneath all that were some lumps I couldn’t quite figure. But I knew my mistress would explain everything I needed to know. So I just stayed there and waited her further instruction.

"As you can see, I have provided you suitable attire as my servant. I know you will recognize the panties, bras and garters and hose. But as a servant, actually my maid, you should wear the appropriate uniform of your station. Therefore you will be wearing a French Maid’s uniform when you are here serving me. I have also selected a pair of black patent high heels and a nice brown wig to cover up that too short hair on your head. And lastly, there is some make-up in there to complete your transformation.

"I will instruct you in all these things after which you will be expected to take care of them yourself. But before all that, we have one more thing to take care of. You are fortunate in that you have little hair on your legs and chest. However, it is still too much on your legs and frankly, I think your pubic hair has to come off too."

I stared at her in horror. I began to protest, thought better of it and nodded helplessly at her.

She smiled at my obvious distress. "Too bad sissy, but rules are rules and hairy legs and crotches are not for you. Into the bathroom right now!"

Numbly I walked into the bathroom and waited by the tub. I noticed a towel laying on the floor in front of the toilet with a razor, bowl of water and shaving cream on it. She came in and went over to the toilet, lowered the lid and sat on it. "Come over here and stand at the edge of the towel facing me." She ordered.

I did so. Mistress then took a wash cloth and soaked it in the bowl. After that she used it to wet down my pubic area thoroughly. Then she filled her hand with shaving cream and liberally applied it my pubic hair completely covering it in white foam. With some care and caution she began to shave off all of my pubic hair. It tugged a little here and there and hurt a bit. I think I began to cry silently as she made her short strokes. I felt so completely humiliated, so emasculated that all I wanted to do was crawl into a black hole and die. Yet the operation continued. As she got close to my cock and balls, she grabbed my shaft and held it out and away from my body. Suddenly I found myself turned on again and an erection forming. This seemed to tickle her as she laughed quietly to herself. "You really are a little sissy aren’t you? You don’t even have the balls to stop me from this do you? You’ll just take it won’t you? And you know why…"

Shortly, she was finished and I was shaved like a prepubescent little girl. She reached over to the faucet in the tub and began to run the water adjusting the temperature. "Get into the tub, sissy and sit down."

"Yes, Mistress." I managed to reply as I got into the tub. The water, at least was a comfortable warmth. As it rose it washed away the remaining foam from the shaving cream revealing the true extent of her efforts. It was as if I’d never had pubic hair. She pointed to it, "You’d better maintain that too. Understand?"

I nodded and she turned off the water, handed me the razor and cream and said, "Alright I’ve done quite enough for you. It is time you learned to take care of yourself as well as me. Shave your legs and be careful. I don’t want a lot of blood, you understand."

Slowly I began the process of shaving my legs. I lay back in the water and spread the shaving cream first on my right leg. Then I took the razor and gingerly began running it up and down the top of my leg. With a minimum of nicks, I then moved to the sides and finally, with some struggle, got the back of my leg. Finished I let back down in the water and rinsed it off. Then I repeated the process on my left leg. When I was done I sat there and waited for her instructions. She had me stand up, release the drain and then turned on the shower to completely clean me off of soap and bits of hair. Finally I was told to get out of the tub and towel off. With that, she marched me back into the bedroom and to my trunk. Where once again I stood.

"Okay sissy girl, time to get dressed. First get out a nice white garter belt and a pair of hose and put them on."

I did as she asked getting out the garter and hose. I slipped the garter belt up to my waist. Then I rolled the hose and slid it up each leg and it felt really sexy and smooth as they went up my freshly shaven legs. I was regaining my hard-on again. Then she had me pull out a pair of the white, lacy panties and a matching bra. I pulled them on and began to feel like the sissy I really was.

"Alright, now you must get into the maid’s uniform. There is zipper in the back and you will have to learn how to zip yourself up because I am not about to zip up my maid’s uniform. So get it out of the trunk and while you are at it, get out the high heels and the wig. Put the wig on first, then the heels and finally slip into that uniform. And do it with a little grace."

With trembling hands I got out the uniform, shoes and wig. The wig went on easily. It was a brown one, close match to my natural hair, cut with bangs and slightly longer than shoulder length on me. It made me feel really feminine for some reason and I found I could hardly wait to get the shoes and uniform on. Luckily the shoes fit fairly well, just a little tight. In time they’d stretch out and be comfortable. But I did feel a bit unsteady on them and had to pay attention to keep my balance. Finally I got into the uniform by stepping into it and pulling it up. The satin fabric felt very sexy against my skin and for the first time I felt like I was becoming the woman I always wanted to be. Subservient and helpless before my Mistress, ready to do anything she asked. I had worn a dress some time in the past and had managed to figure out the zipper in the back. Nevertheless, it was still awkward for me to try to reach behind and pull the zipper up to the neck. I struggled with it for some time before successfully getting it done. When I looked at her she was clearly annoyed with my too-slow response. She frowned sternly and said, "You are far too slow dressing. Especially with all the ‘experience’ you have had. To the bed and assume the position!"

I cringed and hesitated just a moment. This further angered her and she reached out, lifted my skirts and grabbed my cock and balls and yanked them to drag me to the bed. I cried out a bit because it hurt so much…which only seemed to please her. Roughly she shoved me again and repeated the command, "Assume the position. Now!"

Without hesitation, I did as she demanded. I felt her lift the back of the dress to expose my panty-clad bud. She gave it a quick slap and then slid the panties down to expose my candy ass. I heard her move away to the dresser where she retrieved the paddle. Shortly she was back, standing behind me to my left. Without preamble, she gave me a sold whack that shook me through and though. I whimpered, then bit my lip and just tried to hang on. In short order she’d whacked me four more times. My butt was really stinging and must have been cherry red. I thought that would be it but suddenly I received another whack. And another, and another. In all, I got fifteen that time each one harder than the last, each further reducing me to abject humiliation before her. My little ass hurt so much. I was crying silently, tears running down my cheeks. All of which did not go unnoticed.

"Alright my naughty little sissy. That will do for now. I think you got the message. Don’t disappoint me…ever! Now just remain in that position for a while. I have a few things to do. Don’t move one inch."

With that, she put the paddle away and then left the room. I could hear her going downstairs. Then it was quiet. Slowly the fire left my poor ass. But bent over as I was started to become very uncomfortable. All I wanted to do was stand up and stretch. However, I knew the price of disobeying my Mistress and I remained, as I was, my poor, red butt high in the air.

After a time I heard her coming back upstairs along with the sound of ice in a glass. Evidently she’d gotten another drink. She went directly to the dresser and got the paddle again. Inside I cried out a silent protest, "No!" I couldn’t understand what I’d done now. I’d obeyed her completely. Nevertheless, she gave me a solid whack on the butt and then set the paddle down.

"That is just for thinking of moving my sissy-dearie. I can read you like a book and don’t forget it! Now, you may stand up, pull those panties back up, drop the skirt and face me."

With some amount of pain to my back, I managed to right myself and get my panties back where they belonged. I looked at her expectantly.

"Finally, we need to take care of your make-up and nails. Go to the trunk and get out the make-up bag. Open it and pour the contents on the bed. The first thing I want is the foundation and eye shadow."

I went over to the trunk and withdrew the bag, then went to the bed and emptied it on to the covers. The foundation and shadow were easily identified and I pulled them out of the pile. She took them from my hands and opened the foundation.

"Foundation will hide some of your obvious flaws…like the 5 o’clock shadow you are wearing. As an aside…be damn sure you shave just before you come over here next week. If you don’t, you will be really sorry, believe me."

I nodded my understanding, "Yes Mistress, I will be sure to shave next time."

"Be sure you do." She said as she began applying the foundation lightly to my face. Next she took out the eye shadow and brushed it on my eyelids. Then she instructed me to get her the blush and the lipstick. These she applied in turn instructing me to move my lips in and out to spread the lipstick evenly. With that, she stepped back to examine her handiwork.

"Not bad for such a novice sissy. I may take you out shopping with me sometime! Wouldn’t that be fun?"

The thought scared the hell out of me but I responded with a "Yes Mistress."

She looked at me sternly, ‘Don’t lie to me sissy. I can tell by your voice nothing would upset you more. Right?"

Again I gave her a "Yes Mistress."

"Yes, I thought so. Well, we’ll overlook it this time. But honesty is going to get you a lot further…unless you like the paddle.

Okay, then we must do your nails. A bright red polish is what I have selected and I expect you to keep your toes polished ALL the time…got it, ALL the time?"

"B-b-b-ut Mistress, all the time?" I cried. "What if someone sees?"

"Too bad for you is what I say. The rule stays…all the time. Now, here’s the nail polish. It’s time you began to make yourself up. Start with the toes; apply it smoothly and evenly stroking the brush in only one direction…away from the cuticle. Once the toes are done, then do your fingers."

I took up the nail polish bottle and opened it. I was still standing up and looked at her questioningly. She nodded to the bed and I went over to sit down. I took off my shoes and then my hose and began the process of applying the polish to my toenails. It went quickly enough and soon I turned to my fingernails. This took a little more concentration especially after one had was done. I knew I didn’t want to mess them up in any way. My cute little ass couldn’t take it!

When I finished she took the bottle from me and gathered up all the other stuff from the bed and placed it back in the bag when then went back into the trunk. Then she picked up my street clothes and put them in the trunk too. I began to get nervous as it dawned on me what she was going to do. Quickly she closed the top, spun the combination tumblers and then turned to look at me with a smile on her face.

"You do understand don’t you? I’m the only one who knows that combination and I am the one you must please if you ever want to open that trunk again. Every time you are here, you will get all your sissy things out of the trunk and put your street clothes into it. Then lock and spin the tumblers. Understand?

"Yes Mistress, I do understand." I said miserably. I was just realizing how completely she held me as her servant, her slave! I couldn’t even run away now. Where would I go dressed like the sissy I really was? Oh the humiliation and shame I was feeling. I began to cry again…quietly, the tears flowing down my cheeks. She shook her head and laughed at me. "God, you ARE a sissy, aren’t you? Just too pathetic for words. I don’t know why I keep you around. We just better hope you can take real good care of me, won’t we?"

I nodded miserably and sniffed.

"Yes, I know you understand. Now get your hose and shoes back on and get over beside the trunk."

I did as I was told and once again found myself standing in front of the trunk. She sat back down and examined me once more. She nodded to herself and smiled. I guessed she liked the results of our efforts to make me over. I could only imagine what I looked like. And the thought of it began to give me another erection. Which she noticed after a bit. A frown came over her face and she seemed to be considering what was to be next for me.

"I think the only good sissy is a limp sissy. Don’t you?"

I managed a weak "Yes Mistress."

"Of course you do. Which means we must do something about that useless thing filling your panties up. The question is-What? Or maybe more to the point-How?"

She seemed to consider the problem then stood up and turned towards the bathroom. "Follow me." She ordered.

I followed her into the bathroom, heart beating like mad wondering what she had in mind for me. I remembered our last session when she "took care of me." I was hoping for more of the same and the thought just made my erect cock all the harder. I was actually smiling as I went in. She was standing over by the commode, her arms crossed and looking quite stern.

"Take your shoes off, sissy and then step into the bathtub. After that pull your panties down to your knees and stand facing the faucets."

Trembling and sensing things were not as I’d hoped I slipped the shoes off neatly set them beside the tub and stepped into it. I hiked up my skirt and lowed the panties to my knees. My cock pointed straight out and was gently bobbing with the beat of my heart. I stood there waiting her next instruction.

"Alright sissy. Why don’t you just take care of yourself? Take that thing and masturbate yourself…and go ahead and take your time. I’d like to see just how you do it. Now get started!"

Embarrassed like never before, I took my cock in my hand. She seemed to snicker and I felt my face grow warm as I blushed in my humiliation. I just couldn’t believe I was having to masturbate in front of some woman. It was so bad yet I had no choice but to do as she ordered. So I began a slow stroking of my cock, up and down gently which served to increase it’s thickness and length. It also got me excited and very quickly I had forgotten my Mistress’ presence and was lost in the intensity of the feeling. I was seeing myself dressed as a French maid, hose and garters showing to all. As I stroked harder and harder I actually began to caress my tits feeling them through the satiny fabric of the uniform. I groaned a little in the sheer pleasure I was feeling and before I quite knew it I was cumming mightily, letting it shoot to the floor of the tub. Some got on my hands and lubricated them so the feeling was even more intensified as the last of my cum dribbled out. Even then I continued to stroke my slowly shrinking cock savoring the last of the feeling. Then I was done, standing there drained and panting. I opened my eyes to stare directly into my Mistress’ eyes. She smiled.

"Well, aren’t we just something else? That was quite a display you put on. I hope you enjoyed it because I don’t know when I will let you do it again. In fact, from now on, you may not masturbate without my permission. And that means here or elsewhere. Got it?"

"Yes Mistress, I understand."

"Good. Next, you’ve left a mess in my bathtub haven’t you? I don’t think I want to bathe in that. Why don’t you get down there on your knees like a good little sissy and clean it up? I think your tongue will do a fine job so get your ass down there and lick it up!"

Inwardly I groaned. But outwardly I moved without hesitation. I was learning. With a little reluctance I placed my face close to the tub bottom where my cum had fallen and put out my tongue to lick it up. Once started, it was really not so bad. The slightly salty taste was okay even though it had cooled off. I gradually made my way down the short length of the tub and licked up all the cum I had spilled. When I had finished I looked back up at my Mistress and she nodded me back up again to a standing position.

"Out of the tub, get those panties back up to cover yourself and get your shoes on. When that is done, I want the tub cleaned. There’s a ring and anyway it hasn’t been cleaned for a week. You’ll find tub cleaner under the vanity. I’m going downstairs for a refill. When you’re done come downstairs for your next assignment.

With that she left and I got out the tub cleaner and began the task of cleaning it. I had to get down on my knees to scrub the tub and the effort lifted my short skirt above my ass revealing my panty-encased ass. I could just imagine what I looked like and felt the faint trembling of a hard-on just beginning. Very shortly I was finished. I put things away and then made my unsteady way down to the first floor where she was sitting in the couch with her drink and some work she’d brought home.

"Done? Good. Next get out to the kitchen and wash the dishes. When you are through with that I would suggest you do a light mopping of the floor. When you’re done with that, go around the house and collect the trash. You’ll find trash bags in the pantry. By the time you finish with all that, we’ll have some additional ‘tasks" for you." She smiled slightly nastily.

I suddenly felt like the servant I was. I couldn’t quite believe I was going to be doing her housework for her. I mean I hardly did any of this stuff at home and here I was in a maid’s uniform doing dishes and floors and what-have-you. However, she was in charge so I trotted off to the kitchen and did the dishes and the floor. After that I went around the house and collected trash from each of the rooms upstairs and down. When I was done with that I went back to the living room.

"Mistress?"

"Yes?" She replied.

"Mistress, I am done with my chores. What may do for you next?"

"Well sissy, I don’t for a moment imagine you expect ME to take the trash out, do you? And you know I forgot to pick up the mail on the way in this evening. So, why don’t you just tie off that trash bag and take it out to end of the driveway and while you’re there, get my mail. No need to dash out either. Just take your time." She smiled so sweetly at me like she was just asking something that was no big deal.

I was really shaking all over on this. I was supposed to go outside, What if someone saw me. Oh my God, I thought, this is terrible. Even if it is dark out, I might still be seen and recognized. I just can’t go out there.

She was very aware of my hesitation and fear. And was enjoying it immensely too. From the look on her face though, there was no doubt she meant it. But I had to try one time to stop this.

"Mistress?"

"Yes? There’s a problem? You don’t know where the twist ties are, maybe?"

"N-no Mistress. It’s just, well, going outside, someone might see me, recognize me. What would I do? It would be so humiliating, so degrading."

"So? Am I supposed to worry? Listen, you trot your lacy ass out there, drop the trash, pick up the mail and if any one sees you I expect you to curtsey and smile at them. Now get going."

I was almost in tears by now. My heart was just hammering away in my chest; I was so scared and so at her mercy. I knew if I delayed any more it’d be the paddle and then I’d still have to go outside. I turned and went back into the kitchen to get the trash bag, went out to the front foyer and with a lot of fear and trepidation opened the front door. At that moment it was quiet out, no cars moving, no one out walking. I steeled myself and stepped out into the night. Part of me was screaming in fear but part was getting slowly excited despite that fear. I walked down the drive to the mailbox. My heals clicked on the concrete. I could feel the cold air up under my skirt on my ass and my cock. It actually felt sexy to be so exposed. I began to relax a bit and tried to enjoy it. As I approached the mailbox suddenly a car appeared down the street. I turned slightly and its light swept across me. I panicked and felt like running crazily to the nearest bush or tree. Instead, I somehow held my ground, set the trash down and opened the mailbox to get her mail out. The car came down the street. I didn’t recognize it and relaxed just a little. As the car passed by me, the driver, a man of about forty-five gave me a leering look, like he might do something indecent. As my Mistress had instructed, I curtseyed and smiled. Then turned to head back when inspiration hit me. As I walked away from him, I reached behind and gave my skirt a flip revealing my panty-clad ass and freshly shaved legs. He honked and then sped away. I felt incredibly sexy and feminine, like I’d made it as a woman, a desirable woman. Instantly I was hard again. I looked up and realized my Mistress had come out to the front step and had witnessed the whole thing.

As I approached her, she smiled. "So my little sissy, a bit of the slut too? We may have to do something about that in the not too distant future."

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