Cyber Sissy Ch. 03

I was able to mimic her motions fairly well, but she still insisted I do it several times until at last she was satisfied that I had it mastered.

"Now take us to the freeway and head north," she ordered. "I'll give you directions from there." For the next hour and a half, my mind was kept busy with just the chore of learning to drive while wearing heels. As we approached the outskirts of the next large city to our own, Mistress Megan told me to take the next exit. From the bottom of the ramp, I could see the mall she had in mind. Without being told to do so, I drove into the large parking lot, managing to find a spot fairly near the mall entrance. Megan got out first, coming to my side to see if I had truly learned how to exit a car gracefully. As I did, she clapped her hands to show her approval. "That's much better my pet. Come with me, we have some serious shopping to do."

The rest of the afternoon was a blur of shops. First, we went into an upscale lingerie store. We spent considerable time picking out panties, bras, garter belts, stockings and several pretty nighties. The styles ranged from demure to naughtiest of crotchless panties and open cup bras. Megan took great delight in holding these most feminine of garments against me while she oohed and aahed about how good they would look on me. All the while she did this, she wore an incredibly mischievous grin. At one point as we were looking at several full length nightgowns, she made me hold a lacy lemon yellow number against myself while she stood back to get the full view. I saw the clerk smirking in our direction, a knowing look on her face. I was mortified to say the least. Megan thought this to be hilarious, and made several more remarks about how hot I'd look in some of the more risqué choices.

By the time we had made all our selections Megan paid for them with her gold card, teasing me in front of the sales clerk. "What sort of woman goes shopping and leaves her purse home, you're such a ninny. It's a good thing you have me to take care of you."

As we left the lingerie boutique, I could feel how aroused my panty trapped cock had become. Megan noticed this and whispered in my ear, "You certainly seem to be enjoying yourself my pet. Try to contain yourself though, we don't want any nasty bulges giving away what you keep in your pretty panties, do we?"

I whispered back, "I'm sorry Mistress, but this is getting me excited. I don't know what I can do." "As usual, your Mistress has the solution," she replied. "Come with me, and we'll powder your nose."

She led me into the ladies restroom. Thankfully, it was empty, leaving us alone. She led me to the furthest stall and once inside, latched the door.

"I must accept part of the blame for this, she said. "I should have known how excited you were and taken care of this before we left the house. Pull your dress up for me pet, and Mistress will try to do something about your problem." I pulled the hem of my dress to my waist, exposing my panties. Megan pulled them off, commenting as she did so, "I'm glad you had the foresight to put your panties on over your garters. It makes it so much easier to get them off." Once they were off, she wrapped them around my cock and began to stroke it. In no time at all, the beginnings of my climax shook my body, causing my legs to tremble.

"All right my pet, let your Mistress do all the work," she whispered. "You have my permission to cum now. Fill your panties for me."

To ensure my compliance, she reached down with her free hand and cupped my swollen balls, massaging them gently. My cock erupted, filling the silky panties with juices. When she was satisfied that she had milked the last drop from me, she used a tissue to wipe the last of it away. She took a new pair from the bag and after removing the tags handed them to me. "Here put these on. It's a good thing we bought a new pair or you'd have to go without for the rest of the day."

I put on the clean panties and pulled my dress down. Megan led me from the restroom, depositing my soiled panties in the trash can at the door.

We finished our shopping with stops at a shoe store and dress shop. We bought only two dresses and three pairs of shoes there. By the time we were finished, it was late afternoon and time to go home.

As we walked to the car, I commented, "Mistress, we seem to have purchased an awful lot of lingerie, but not much in the way of dresses or other outer wear."

"You won't be going out that much just yet, my pet. You will however have to wear your pretties any time you are with me. That's why you need so many."

"But Mistress," I stammered. "What about when I'm at work?"

"I should think it obvious that since you are at work, you will wear your pretties under your suit," she replied frostily. "Even though to the people at the office, you are the boss, we know better, don't we? Your panties and whatever else I decide to dress you in will be a constant reminder that you belong to me. You really have no choice in the matter. I'm sure you remember the pictures I took last night and what will happen if you disobey me."

She then changed the subject, asking, "Are you as famished as I am my pet? That's a silly question of course. You must be starved! I know how much shopping can tire a girl out, lets stop at a little restaurant I know on the way home."

Dutifully, I got in the car and began the drive home. About half way there, Mistress directed me off the freeway. After a short drive, we were at the restaurant where we were immediately seated.

Megan ordered for both of us. We both were going to have the Chef's Salad with oil and vinegar dressing. "A girl needs to watch her figure and you're no exception," she explained. I felt as though every eye in the place was on me, that everyone there knew I was really a man in women's clothing. Megan dismissed those thoughts, explaining that perhaps the only reason people were staring was that I had not taken off my sunglasses. I still didn't take them off, figuring it was better to be stared at than recognized.

After the light lunch, Megan had me detour slightly to a store devoted to sex toys. She made me stay in the car while she went inside, returning ten minutes later with a bag of what she referred to as her training toys. She wouldn't elaborate, simply saying I would find out what she had bought when the time was right.

There was silence as we drove home. As we pulled into the drive, she told me to bring all the packages up to my bedroom. Once everything was in, she spoke, "Take off your clothes and take a quick shower. Then we're going to have a fashion show, I want to make sure everything fits."

The next few hours were a blur of soft, silky fabrics in every style and color imaginable. Megan made me strut and pose in each ensemble, making comments on each one. She was especially partial to the last outfit she had me wear. It was purple with lavish black lace. The bra had black lace trimmed holes where the nipples were and the panties had a zipper from front to back. The possibilities of this outfit were immediately apparent.

Megan took note of my apprehension while wearing it. "Don't worry my pet, there will be times that I want you to be able to wear your pretties without denying me access to every part of you. When the zipper is closed, you will have your modesty, but when I open it, I will be able to tease and use any part of you I want. You will be completely exposed and vulnerable, even though you have a complete set of lingerie on. The other advantage is you don't have to bother putting the garter straps under the panties. I hope you appreciate all the trouble I go to in making you comfortable."

"Oh yes, Mistress, I certainly do," I replied.

"Well in that event, I'm going to allow you to prove it," was her response.

She went to the closet and got a spare pillow. Placing it in the middle of my bed, she commanded, "Put on your wrist and ankle cuffs and lie on your back with your cute little ass on the pillow."

I did as I was ordered and once again found myself bound to the bed. The big difference this time was my hips were elevated by the pillow, forcing my crotch up.

Megan stripped off her clothes and once completely naked came over to where I lay. She began to lightly trace the zipper with a finger tip until she reached the rosebud of my ass. Pressing lightly against it she said, "The time is coming when you will have your virginity taken. Because I care about you, I'm going to do something that is practiced by an obscure South Pacific tribe. When a girl is about to be married, the other women of the tribe use a series of wooden dildos to prepare the maiden for her marriage bed. In this manner the girl gets the unpleasantness of defloration out of the way and is able to fully enjoy the first time she is taken by her husband. I am going to prepare you in much the same manner. Beginning tonight, you will have a plug inserted. The first one will be quite small, the next a little larger and so on until you are completely ready for the ultimate moment in a girl's life."

She went to the bag from the sex toy store and came back with a small butt plug. It was about two inches long and one inch in diameter at the widest point. It had a base to prevent it from getting lost inside and an indentation to prevent it from being easily expelled.

Megan pulled the zipper in my panties all the way down, exposing my cock and ass to her gaze. She took a tube of lubricant and began to coat my ass with it. She coated the butt plug and placed it at my opening, saying, "relax my pet, this is for the best. Soon you'll crave the feeling of having your pussy filled."

I felt her increase the pressure against my ass and began to do as she instructed, relaxing my sphincter muscle. I could feel her inching it inside, the discomfort growing until it passed the widest point and she drove it all the way in. Uncomfortable at first, I soon started to get a feeling of arousal as my body got used to it. This was evident by my penis, which while it was flaccid at first, soon grew as the sensation of pleasure chased away the ache.

"There my pet," she teased. "Doesn't that feel better? Not that what you want is of paramount importance, but it would be nice if you could learn to enjoy the inevitable. I'm afraid you're going to have to sleep with it inside you tonight. By morning, you'll be ready for the next size. By tomorrow night, you'll be ready to become a woman. For now though, I'm going to require that you service your Mistress with your clit. All this shopping and watching you prance around in your dainties has gotten me quite aroused. I think that since you are the cause of my problem, you should be part of the solution."

She straddled me, holding my penis upright while she parted her pussy. When she was satisfied that she was properly positioned, she lowered herself until my cock was completely inside her slippery folds. A look of rapture came over her face and I felt her getting even more wet than before. She began to rock back and forth, grinding herself against me. Her motion increased at an almost geometric rate. All this had the predictable effect on me and just as the first tremors of her climax began, my body arched upwards as my body spewed its hot load into her steaming depths. "YES MY SLUT, JOIN YOUR MISTRESS, COME WITH ME NOW!!!" she screamed. Our juices mingled in a cauldron of hot oil as our passions boiled to a shattering climax together. Megan collapsed against me, crushing her breasts against mine. After a moment of rest, she fingered my hair, twirling it around and around. "You are such a precious find," she whispered. "You make me so happy. I'm so glad I discovered your naughty secret.. I want you to sleep now. Tomorrow will be a big day for you."

To be continued...