Caught, Part 3.

In time with my new mistress, things settled into a routine. Every Thursday night I presented myself on her doorstep. She would let me in and I would head upstairs for her bedroom, undress and wait for her to unlock the trunk so I could get out my "things" and get dressed. At this point, I had become very subservient to her and was willing to do anything she ordered. I was wearing panties all the time now which was not easy since I was living at home. I had to secretly wash and dry my panties and just toss clean pairs of my male underpants in the wash to make it look like I was still wearing them. I also was keeping my toenails polished in red which was not quite so difficult. But I could no longer go around the house barefoot like I used to.

Each week I had to clean her house to her complete satisfaction and each week I always managed to mess up and receive a paddling. It was an especially bad one when I broke a glass. Oh my God, did I get paddled. She heard it break and came storming into the kitchen demanding to know what had happened. In trembling words I told my Mistress I had dropped and broken a glass. With that, she ordered me to go assume the position. As we were downstairs, I went into the living room, stood before the couch, dropped my panties down to my ankles and bent over. I could hear her go up the stairs and into her room. Then I waited for what seemed like forever. I was so scared of how heavy the spanking was going to be. And even at that I could feel my cock grow in anticipation.

She finally came back downstairs and into the living room. She stood beside me and without a word, began the paddling session. She’d never hit me that hard before. I took 25 licks and my poor, little ass was just screaming in pain. I had to bite my lip so hard to keep from moaning in pain and I was just crying like crazy by the time she stopped. I could hear she was breathing a little hard after the effort. She tossed the paddle on to the couch in front of me. Then I could see she’s removed the fabric from it. No wonder it hurt so much!

"Sissy," she said, "I won’t tolerate a clumsy maid breaking things. Next time you are washing dishes be very, very careful or it will be worse for you. Now, pull those panties up and get your red ass out there and clean up the mess and then finish your chores."

After that, I was very careful.

On the plus side, she began allowing me to pleasure her with my tongue. At some point in the evening she would take me up to her bed and lay me out on it, spread-eagled like the first time, tie me up and then sit on my face. I would lick her luscious cunt for as long as she liked until she came and came and came. After that she would take a bath leaving me tied up and so hard. When she would be done with her bath, she would release me and take me into the bathroom. Sometimes she would make me masturbate myself in front of her, sometime she would masturbate me herself. Either way, it always felt so good and I always had to clean all my cum up by licking it up. She once told me it was preparation for bigger and better things but I don’t think I really grasped her meaning at the time.

Things changed radically after two months. One night I arrived at the usual time on Thursday and headed upstairs and proceeded to undress and await my mistress. This night she didn’t make me wait long. She came in almost immediately after I was through taking my clothes off. She sat on the bed and ordered me to turn and face her.

"Tonight, my little sissy, we are moving to a new level. It is time for some ‘advanced’ training for you." She said. "First, you must get dressed. But I only want you in your panties, bra, garter and hose and heels. And, of course, do all your make-up and wig. The trunk is unlocked so go ahead and get ready for me. When you are through, come downstairs and get me."

With that, she got up and left the room. I proceed to transform myself into the little sissy-girl I had become. Of course, this was hardly a bad thing for me and I was looking forward to mincing around in just panties and bra. I got such a hard on just from thinking of it and caught myself almost rubbing my cock before realizing Mistress forbade that without her permission.

By this time I had become very skilled at dressing and doing makeup and my wig. So, it was not but fifteen minutes and I was presentable for my Mistress’ purposes….whatever they might be. I shivered in anticipation and hoped I could please her completely that night. So it was, I left the bedroom and went downstairs.

I found her in the living room on the couch. Beside her was a tastefully wrapped package. As I walked into the room, she looked up and beckoned me to her. Silently I went over and stood in front of the couch slightly to the right of her. Incredibly, she reached out and began to pet and stroke my cock. I began to shake all over in exquisite anticipation. I couldn’t imagine why my Mistress was being so kind and generous to me. She smiled at my excitement.

"Sissy, dear, please kneel down on the floor beside me and hold out your hands."

I did as she asked immediately.

"My dear sissy, it is time we moved beyond the simple mistress/slave relationship we have. You must expand your understanding of just how worthless and beholden you are to me. To do this, we are going to begin with some new training for you. Which is why I have this ‘present’ for you beside me. It will start you on this phase of your training. And I expect you to learn your lesson well. You know the consequences of not learning, don’t you?"

"Yes, Mistress. I do know."

She picked up the package and laid it in my open hands. "Then go ahead and open it."

I relaxed slightly and proceeded to open the package. Under the wrapping was a plain box. I opened it and found within a strap-on dildo. My face must have registered my surprise and puzzlement. She smiled at this and took the strap-on out of the box.

"Where do you suppose This is going?" she asked.

I was quiet a moment as I considered the possibilities. There weren’t many and I had the feeling my ‘present’ would soon be in me in places I was a little scared to think of. I looked at my Mistress and said, "In me, Mistress?"

"Oh, you are a quick one, aren’t you? Yes indeed, in you. It is time you acted the sissy slut you are. You need to know what it feels like to have a cock thrust into your mouth and then shoved up your candy ass. You cannot become truly subservient until that happens. Tonight, I am going to dildo train you. You will suck this dildo and then I will slam it into your ass until you scream for mercy. When I am done with you, you will be so much more my slave."

With that, she stood up and tossed the strap-on on to the couch. I was still kneeling on the floor beside the couch knowing not to get up without permission. She unbuttoned and took off her blouse. She was wearing a black lace, push-up bra that really made her breasts look delicious and sexy. I wanted to just dive into them and get lost forever. Next, she stepped over to me and turned so her back was to me.

"Unzip my skirt, sissy." She commanded.

I did so and she let it drop to the floor, stepped out of it and ordered me to hand it up to her which I did. It was all I could do to keep from just cumming right then. She had on a pair of tight, black bikini panties, black garter belt and hose. Standing there over me, dominating me completely I just felt so completely her total slave. I wanted to do anything for this magnificent Mistress I was kneeling before.

She stepped back and stood with her hands on her hips looking at me supremely and haughtily. She told me to get the strap-on and hand it to her. Then she stepped into and cinched it tight. Suddenly my Mistress had a huge cock on her that was pointed squarely at me. I felt my own cock tingle in excitement at whatever was to come now.

She commanded me to remain on my knees but to turn and face her. As I did so, she stepped towards me placing the strap-on right at the level of my mouth.

"Take it in your hand and stroke it. Stroke it like you would like to be stroked." She ordered.

With trembling hands I took it and stoked as she had ordered. I felt so lowly, like some slutty little girl. The dildo felt a lot like my own cock and I could picture myself doing this to a real man. Doing so, only excited me more and I found myself enthusiastically running my hand up and down the shaft and fondling the balls. With each movement I was becoming ever more and more feminized and reduced to slavery. Very soon she ordered me to take the shaft and put it in my mouth to suck and lick it. By then I was eager to do this and immediately put it and proceeded to run it in out of my mouth. My tongue played across the surface and my lips made an "O" for it to slide in and out of. My Mistress began to thrust her pelvis back and forth in time with my movements. I could see her close her eyes as she got into the session and started getting turned on herself. She began to caress her tits with one hand while rubbing her vagina with the other. This went on for 10 or 15 minutes until she had a nice orgasm and wound it down.

She stepped back withdrawing the dildo from my mouth. I was panting also and terribly turned on. There were damp stains on my panties from pre-cum leaking through. She ignored the stains and ordered me to stand up. As I did, she walked over to a side table and picked up a tube of KY Jelly I had not noticed before. As she came back over she was unscrewing the top and smiling knowingly.

"Take your panties off, sissy." She said, "and lay them on the couch for now."

I slipped my panties off and put them to the side and turned back to her. She handed me the KY Jelly.

"This will lubricate you and help get you through the next phase. I am going to take your virgin ass tonight and fuck it like you’d like to fuck me. And then you will be totally mine. Got it?"

Shakily I nodded, then followed up with a "Yes Mistress."

"Take the jelly and apply some to the strap-on. You might want to be real liberal with it too."" She smiled evilly. "Then take more of the jelly and lube up around your asshole. When you are done, give me the KY Jelly, and kneel on the edge of the couch with your ass facing me. Spread your legs…wide, I’d advise, and brace yourself against the back."

Nervously, I did as she demanded. I was shaking slightly and not so turned on anymore. She stepped towards me and I felt her hands on my hips as she positioned herself to take me.

"Now sissy, this will very likely hurt. Maybe a lot. So I am going to give you permission to cry and moan. But just this time. Next time I will expect you to take a cock like the slut you are and no crying or moaning. Understand?"

"Yes Mistress" I quavered. "I will try to be good about this for you."

"Good, Just don’t get too loud."

With that, she moved forward and I felt the press of the strap-on against my ass. It was cold and startled me a little even though I was expecting it. I tensed and she must have sensed it. She told me to try to relax my asshole as much as possible. Not an easy thing to do as I found out. But I tried and as she increased the pressure, I could feel the head penetrate me and slide in to my ass. It hurt a little and I tensed more. She stopped for a bit and let me get used to it. Then once again she pushed on me and the shaft began its inexorable slide up my ass. With each fraction of an inch, it hurt more and more and yet at the same time I began to feel more and more excited. My cock got hard again even as I gritted my teeth and began a low moan. My eyes were tearing and I felt torn apart in there. Eventually, she got the entire dildo up my ass.

She rested for a while and gradually I was able to relax. Then she began a slow, shallow back and forth in my ass. I realized she was pumping me like a guy would, to take my virginity with her hard shaft. This turned me on more than I though possible and I began to move in harmony with her, pulling back and forth with her to enhance the movements. The pain diminished quite a bit and I found myself enjoying getting fucked in the ass. She picked up the frequency and length of her thrusts and I took everything she gave me. I could tell from her breathing she was getting turned on as well and after about fifteen minutes of this she came again…this time very loudly.

After she was through with her orgasm, she slowly withdrew the dildo from my ass. As it finally exited, there was quite a bit of residual pain in there and I sort of moaned and cried again as I tried to endure it. She let me stay that way for a minute or two then commanded me to get off the couch.

I did as she ordered and turned to face her. She still looked so sexy in the black lingerie she was wearing along with the strap-on that was pointing at me.

"Well," she breathed, "you did incredibly well for your first time. You are becoming a first class sissy and servant. I can’t tell you how proud I am of you. And because of your excellent behavior, I have a treat in store for you. But first, remove this cock from me, take it into the bathroom upstairs and clean it up. You know where it’s been and where it will be going again. You will find alcohol in the medicine chest. Better use a lot of it! I will be along in a little while. If you finish before I get up there, just go sit on the bed. And take your panties up with you."

I went upstairs, slowly as my ass really did hurt still. In the bathroom I got out the alcohol and some soap and washed up the dildo really, really well. I figured before it went back into my ass, it would go into my mouth! And exciting thought, I found.

I went back into the bedroom and sat down on the edge of the bed. I felt a little uncomfortable without my panties on. But she hadn’t said I could put them on again. So I sat there, my legs primly crossed, hands one on top of the other on my knee. I could hear her moving around downstairs and then, finally, her footsteps as she came up the stairs.

Upon seeing her as she entered the room, I immediately began getting hard again…she just looked that good and sexy and, well, dominant. About halfway across the room she stopped and looked at me appraisingly .

"My dear, little sissy. You are about to get the gift of your life. Not many Mistresses would ever be this good to their slaves. But tonight you were so good I thing you have earned this reward. Just remember, this will probably never happen again. So don’t get your expectations up…along with your ridiculous little clit!"

I nodded and smiled.

"Alright, lay on the bed spread-eagled."

I did as I was told. She went over to the bureau and opened a drawer and pulled out some short lengths of cord which she used to tie my hands and feet to the four corners of the bed. When she was done, she stepped back to enjoy her handiwork. She then removed her bra and panties and just stood there letting me take in the view of her lovely body. At that instant there was nothing I wouldn’t have done for her just to touch her once. Incredibly, she got into bed with me and began to play with my cock and balls. She even leaned down and gave me brief blow job. By then I was going crazy with wanting to orgasm. Then she played with my little titties. Finally, she swung her legs to straddle me.

"So, sissy, this is it. I am going to allow you the supreme gift. To actually put your little clit into me and cum. But not until I say you can."

She moved back to position herself over my clit, took it in her hand and gently inserted it into her moist and warm vagina. It was all I could do to keep from cumming right then. And she knew it and smiled at my excitement and desire. For the next 5 minutes she pumped me up and down sometimes fast, some times slow and sensuous. I was nearly passing out from the struggle to hold when she said I could let go….which I did with such force. I could feel the cum just gush out into her and I could see her actually in another orgasm. This lasted only a minute or less and then she stopped and just remained there on top of me, me still in her, slowly shrinking down.

She opened her eyes, "Well, that was good, sissy, wasn’t it?"

"Yes Mistress, very, very good. I want to thank you with all my heart. You are the best most wonderful Mistress a sissy slave like me could ever have."

She nodded and began to slowly pull away. "Now, of course, you must clean up your mess. Right?"

"Yes Mistress."

With that, she came forward and placed her vagina above my mouth and sunk down on me. My cum was seriously oozing out of her and dripped all over my face. I immediately began to lick her clit and all around to get every drop I could. The taste of my cum and her musk was exquisite. I just wanted to dive into her forever. But finally I had licked up all the cum I could. She got up and off me. Looking down on me she giggled at all the cum still on my face. She picked up my panties and used them to dry it off. Then tossed them on my clit and left to get a bath.

I lay there in a state of bliss, completely satisfied, happy my Mistress was happy and satisfied too. I could hear the sounds of her bathing and I sort of wished she would untie me and let me wash her. Maybe someday, I thought. I heard her get out of the tub but didn’t hear the water draining. She toweled off and came back into the bedroom. She untied me and told me I could use her dirty bath water to clean up. Then I was to clean the tub…no ring!

Gladly I went in and washed in my Mistress’ bath water knowing she had just been in it. When I was done I cleaned the tub and the bathroom as well and reported back to my Mistress who was lounging on the bed. She told me to return to my street clothes, the evening was over. But next week, we would pick up with some more training.

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