Cyber Sissy Ch. 04

Megan rested for a moment, still recovering from her climax. After a bit, she stood and while making sure the butt plug was still deep inside me, closed the zipper in my panties. I was once again trapped in the silken caress of the purple panties, with my "pussy" filled. Megan kissed me gently on the lips while stroking my cheek. "Sleep well my pet, for tomorrow will come all too soon." With that said, she left me and went to was now her bedroom. Obviously, with my ankles and wrists still bound to the posts of the bed, I had no option but to try and get some sleep. By this time my body had accepted the butt plug and there was no longer any discomfort, only a constant reminder of my submission to Megan.

As I drifted off to sleep, I realized that my submission was not a physical exercise, but a mental one. Obviously, I was physically much stronger than Megan and if I really didn't want all this to happen, I could easily have stopped it. This left me with the conclusion that I was born to serve a woman in this manner. I reflected on how lucky I was that Megan discovered my secret. Obviously, she really enjoyed her dominance of me. My wife was now my Mistress, and to make things even better, a caring and gentle one. She had never done anything to me that caused anything more than momentary discomfort, and then only when absolutely necessary.

As I grew more drowsy, my thoughts moved to what was to happen the next day. I must confess to a slight feeling of anticipation mixed with a little dread. What would it be like to spread my legs and accept Megan's strap-on dildo inside me? How much would it hurt? Would I start to enjoy the feeling of another person invading my most secret place? My reverie was cut short with the realization that my thoughts were those that had to have gone through the head of every girl ever confronted with the impending loss of her virginity. My last thought before drifting off was that I hoped I wouldn't disappoint Megan when the time came.

Sunday morning came all too soon and I awoke a few minutes before Megan came into my room. She untied the ropes from the cuffs and allowed me to visit the bathroom instructing me, "I want you to remove the plug and wash it thoroughly. You may then relieve yourself. Let me know when you are finished."

I hurried into the bathroom and to my consternation, the moment I pulled down my panties, the butt plug fell out! My body had adjusted to the point that unless I made a conscious effort to hold it in, it would slip out. I was about to put it back in before Megan could see that it wasn't where it belonged when I noticed her standing in the open doorway.

She noticed my look of consternation as I vainly attempted to put the plug back. "I rather thought something like that would happen. You poor girl! It's obviously too small for you now. Finish going to the bathroom. When you are finished, I want you to remove your pretty lingerie and join me in your room. There is no need to put the plug back in. I have something else in mind."

It took but a few minutes to complete my morning toilet and I presented myself to Megan as instructed. She was sitting on my bed with a package at her side. "Come here girl and stand in front of me, facing away," she commanded.

I did as she instructed, slightly nervous about what might be in the package at her side. "

Now bend over with your legs spread as far apart as you can manage and grab your ankles. Since you have obviously outgrown last night's toy, I'm going to have to use another type to prepare you for your deflowering."

I assumed the proscribed position and soon felt the cool moistness of the lubricating gel being applied to my backside. Megan took a moment or two to explore my pussy with her fingers, massaging my prostrate until I was erect.

She reached around me to feel my erection. "Would you look at that?" she exclaimed. "The minute I start to play with her pussy, her clit gets all hard and excited. It's almost as though she's starting to associate having her pussy filled with sexual fulfillment. I suppose I shouldn't be surprised, eventually all girls do. You're going to love what I'm about to do to you. This will feel so good. You're may never want me to take it out."

I felt a slight pressure at my opening and relaxed, allowing Megan to insert her new toy inside me. Because I had just spent the last eight hours with the old plug inside me, this one went in with no difficulty whatsoever. To my surprise, it was much smaller than the previous one and I wondered what Mistress had in mind. If I had problems with the last one, wouldn't a smaller one create even more of a dilemma for me?

I needn't have worried! I heard a strange sound, like the one a blood pressure cuff makes when it's being inflated. With each repetition of this sound, the plug in my "pussy" grew a little larger. Just as I was about to tell her that I was getting uncomfortable, Megan stopped pumping and closed the valve at the base of the plug. "There you are my pet. You are now in the final phase of being stretched and prepared for your deflowering. If you start to feel as though it is about to slip out and needs to be larger, you are to tell me and I will see to it. If everything goes right, when I take your cherry all you'll feel is the pleasure of being made love to by your Mistress. I think today will be an easy one for both of us. I'm going to fore-go your morning exercise regimen. I want you well rested for tonight. Besides, I want to allow my anticipation to grow as well. It's not every night I get to take a girl's virginity."

She walked from the room, calling back to me as she left, "I want you to put on your pale blue baby doll nightie and join me in the kitchen. I'm going to make us a good breakfast and then we'll relax a little."

When she left the room, I stood and while marveling at how good it felt to be so filled, slipped the baby doll nightie over my head. Once again as the slippery fabric caressed my body, my "clit" began to grow. This was even more evident when I pulled the gossamer like panties up my legs and over my privates. I slipped my feet into a pair of white slippers and went down to join my Mistress.

As I entered the kitchen, she looked up at me and smiled her approval. "Very good my pet, you are excited aren't you? I know how much you have to be anticipating tonight. Sit down now and eat the breakfast I've prepared for you."

I sat at the indicated place. Megan had prepared some sliced fruit and a bowl of cereal for me. I thanked her and ate, savoring the flavor of each mouthful. My enjoyment was somewhat impaired by the unrelenting pressure of the butt plug. Sitting had exacerbated the feeling of being completely filled and stretched. Megan noticed me squirming a little as I tried in vain to find a way to sit that alleviated my discomfort.

"You will get used to it my pet. I don't want you to hurt yourself though, so I think when you're finished with your meal and have cleared the table, you had better lie down for a while. You may join me in the living room and I'll make sure you're comfortable before I go out for a little while. I have to do some more shopping in preparation for tonight. While I'm gone, you are to do nothing but rest and think about what is about to happen in your life."

I finished the last of my cereal and quickly set about clearing the table. Once everything was spotless, I went into the living room to be with Megan. She was already dressed and ready to go out, one hand behind her back.

She smiled at me and said, "I know you want to behave while I'm gone, so I have something here that will help you. Pull your panties down a little and I'll show it to you."

Once I had my panties down, she moved her hand from behind her back, showing me the latest device in my torment. It was a metal cock sheath with a strap designed to lock it in place. Megan reached down and slipped the sheath over my cock before fastening the strap around the base of my genitals. Next she produced a tiny brass padlock and fastened it to the miniature hasp in the strap.

"There, my pet, now you won't be tempted to play with your clit while your Mistress is gone. As you can see, you will still be able to use the bathroom, but there's no way you can play with yourself, the sheath will protect my interests in that matter. In fact, I will demonstrate what will happen if you do attempt to diddle with yourself."

She swooped down on the head of my cock, sucking it into her mouth. She ran her tongue over the head, flicking the tip against the underside of the glands. In just a few seconds, my cock was growing, trying to escape the confines of the sleeve. The larger it got, the more uncomfortable I became, until the pain caused it to deflate on its own accord. Satisfied that I had learned the lesson she was giving, Megan stopped and grinned up at me. "You see, if you attempt to play with your clittie, all you're going to accomplish is to frustrate yourself. You will have to behave while I'm gone. If you're a good girl, I will give you a present when I return. There's just one more thing I have to attend to before I leave. As long as your panties are down, I may as well inspect your plug. Turn around and spread your legs so Mistress can make sure you're properly plugged and inflated to the proper amount."

I felt her tug at the base of the plug, checking to see that it was not about to come out. "That's wonderful," she exclaimed. "There has been no air escaping at all. It goes to show that when you buy a quality product, it really pays off."

Satisfied that I was prepared for her absence, she pulled my panties back in place and turned to leave. "There's plenty of mineral water in the refrigerator if you get thirsty and the remote for the television is in the drawer of the coffee table. I want you to relax while I'm gone, so feel free to make yourself at home."

She kissed me on the cheek and left me to my own devices. I took a moment to examine the sheath around my clit and found it was as sturdy as I had first feared. There would be no hanky panky while Megan was gone. I contented myself with doing just as she had instructed and sat down to watch a little television. There was only one problem. I found that the only thing I could do was watch a tape Megan had left in the VCR. Every time I tried to change to regular television, I got an error message stating that option was not available. Obviously, Megan had intended me to watch the tape, so I got comfortable and pressed the play button.

As the tape played it became readily apparent that it was about the feminization of an unwilling male. The title of the video was "Forever in Panties." The whole thing was taking place in an office setting. The man was an executive and the woman his secretary. The message was quite clear now. Megan was giving me a preview of things to come.

I watched with rapt fascination as the woman in the tape inflicted her will on her unwilling subject. The premise was that she had found a pair of lacy red panties and a magazine showing men dressed in their lacies. He had thought it secure in the top drawer of his desk, but had forgotten to lock it just one time. That was all it had taken for his secret to come out. She explained in no uncertain terms that unless he danced to her tune, the whole company would find out about what she referred to as "his dirty little secret." This woman used none of the subtlety Megan had used in my journey into satin and lace. She pulled a bra, garter belt and stockings to match his panties from her purse and made him strip and put them on. Once he had completed this task to her satisfaction, she made him put on a pair of heels and model the lingerie for her. She instructed him in the proper way to swing his hips in an exaggeration of the typical runway model's walk. Once she was bored with this, she reached again into her capacious purse and pulled out four pairs of handcuffs, the kind you can buy at a novelty store. She made him lay face down on his own desk and fastened his ankles and wrists to the legs. He was now spread-eagle, open and vulnerable to whatever she wanted to do. She walked around to where his head was and raised her skirt to show him that she had taken off her panties just before confronting him with her blackmail scheme. The camera zoomed in for a close up of her brunette pussy, framed perfectly by her mint green garter straps. She grasped his head with both hands and shoved her pussy hard against his mouth, forcing him to give her oral attention until she came, bathing his tongue with her oils.

If this slave thought she was finished abusing him, he was sadly mistaken. She used her previously worn green panties to gag him with, forcing them into his mouth before securing them with his own belt. She then pulled a dildo and strap on harness from her bag and after stepping into it, walked to where his ass was laying at the edge of the desk. He tried in vain to close his legs, but the cuffs prevented it. She slipped a finger first into a jar of petroleum jelly, then into his nether hole, coating it thoroughly. Sensing what was to come, he tried to protest, to ask for mercy but the panties in his mouth precluded anything but a muffled moan. She continued coating both his ass and the dildo protruding obscenely from her groin. When she was satisfied he was ready, she slowly positioned the dildo at his hole and thrust herself inside him with one smooth motion. This shot was taken in such a manner as to show his face as she entered him. The look of pain and surprise on his face was not contrived. I was sure he really was suffering, his ass screaming from the unwelcome invasion. She paid no heed to his pain, continuing to stroke herself in and out until the friction of the dildo against her pussy drove her into the throes of another shattering climax.

Not until then did she relent, pulling the dildo from his ass. She reached beneath him and finding his cock, teased him about how hard it was. She wondered aloud how could his cock stay so hard if he didn't like what she had done to him. She removed the belt holding her panties in his mouth and using them on his cock, stroked and teased him, urging him to fill her panties with his semen. The hapless male was in no position to argue and his body betrayed him yet again, spurting his male essence into the silky folds of the panties wrapped around his cock. The video ended with the secretary handing him a fresh set of lingerie and commanding him to put them on. She let him know that this was not to be just a one time affair, in fact far from it. He was hers now and his life was to be spent "Forever in Panties."

Watching the video had the predictable effect on my cock, and the restraint of the sheath had made me quite uncomfortable, not uncomfortable to shut the video off, just enough to constantly remind me that I was restrained in the most effective manner possible. I knew it would not be possible to attain any sort of relief while in the cock restraint, so I didn't bother trying. The combination of the harness on my maleness and the constant pressure of the inflated butt plug coupled with thoughts of what Megan was going to do that evening and the effects of the video, made me as aroused as I had ever been in my life. To be that excited and at the same be denied the ability to relieve the pressure building in my loins was sweet torment indeed. I found myself looking forward to Megan's return. I was ready to accept anything if only she would allow me some relief from the pressure building in my balls.

I went to the entertainment center to remove the tape and noticed a stack of books and magazines piled on the built in bookshelf. Curious, I picked them up and started reading the titles.

It immediately became apparent that Megan had been planning my submission for some time. Virtually every title had something to do with women putting their men in panties. Some were obviously works of fiction, others more along the lines of a "how to" manual. It was one of the latter that caught my eye and I pulled it down and began to browse through it. It was titled "How to Petticoat your Man". The author took you step by step, all the way from identifying a likely prospect for feminization to the finer points of impressing on your new slave how enjoyable living in panties could be. While the author went to great lengths to impress the reader with the idea that men are here only to serve women, she also was quick to point out that at some point the slave should be allowed his own sexual release. It was also pointed out that at least initially, any form of release must be combined with either some form of bondage or humiliating situation, preferably both. A prospective Mistress was instructed to create a task/reward situation, associating obedience with intense pleasure.

At no point was a slave allowed to climax unless he was wearing lingerie. Furthermore, a Mistress must make sure he was denied the ability to "take matters in his own hands". The only time he would be allowed the pleasure of release was when he was with his Mistress and under her control. The author suggested the exact same harness I was now wearing. This left me with no doubts as to where Megan was getting most of her information. I intended to read further in an attempt to find out what other sorts of training I could expect when I heard the sound of Megan's car pulling into the driveway. I quickly put the book back and went back to the couch. I had barely settled there when the door opened and Megan strode in.

Glancing at the bookshelf, she commented, "I see some of my books are not where they were when I left. Were you doing a little light reading my pet?"

"Yes, a little," I admitted. "I wanted to get some idea as to what sorts of things might be in store for me."

"If our relationship is to flourish, you will have to leave that in my hands. You will have to learn to trust me and my judgement as to what is an appropriate training regimen." Changing the subject, she continued, "I trust you watched the video I left for you before you started snooping in my library?"

"Once I discovered that there was no choice," I replied. "I felt sorry for the man in that film, his Mistress wasn't anywhere as gentle with him as you've been with me."

"That was the primary purpose for my wanting you to see it. I want you to appreciate how easy you have it. Most women in my position don't give a damn about their sissies. In fact, a lot of them only enjoy themselves when their slave is in pain." She reached down and stroked my cheek, continuing, "You are fortunate that I would rather seduce you into your frillies than beat you into wearing them. I want us to share the pleasure of your submission. That can only occur if you are a willing participant in our playtime. I wanted to wait until later to take you to my bed, but I'm too worked up. It's time to begin your final preparations. I want you to go up to the bathroom and remove all your lingerie. I will join you there in minute to remove your plug and clit protector."

With no small amount of trepidation, I climbed the stairs and set about removing my nightie. I had barely closed the lid on the laundry hamper when Megan came in carrying a large rubber bag with a hose and nozzle attached.

"It's time for your next lesson in feminine hygiene. I want you to be able to fully enjoy the feeling as I take you for the first time. Now that the plug has done its work, the final preparation will be to give your pussy a good douche."

She put the bag down and used a small key to unlock the sheath from my cock. Next, she had me bend over and spread my legs while she deflated and removed the plug in my ass.

"Now, I want you to get down on your hands and knees and rest your shoulders on the floor," she said as she began to fill the bag.