A Sissy Maker Tale Pt. 08

By late Friday Adam was climbing the walls waiting for any message from Mistress Alexandra. As he sat at his desk mired in another daydreaming episode that had become quite frequent the last two days he was awakened from his stupor by the ringing of his cell phone.

" Hello this is Adam."

"Well sweetie I am a bit disappointed that you haven't added my name into your contact list yet."

Adam tried to breath, let alone speak.

" Please remind me of that while I am disciplining you."

Disciplining? Adam gulped in both surprise and a sudden fear of this woman.

"Saturday morning. Eight am. A cappuccino and a blueberry muffin. Do not forget to bring all of your new purchases along with your homework."

And that was it. Adam didn't even get a chance to say hello. But he was suddenly elated knowing that he would be face to face with Mistress Alexandra in less than a day. Without even thinking he was rubbing the cock cage again and the pre-cum began to seep into his new panties. Frantically he began jotting down a schedule for himself to follow in the morning understanding that there were suddenly many different things he had to do prior to his meeting. One was to make sure he was completely smooth and that there were no errant hairs anywhere on his thin frame. He also needed to decide which panty to wear and had to make time to make sure all of the others were cleanly washed. And of course leaving time for stopping off and getting his new Mistress her coffee and muffin.

There was no doubt in Alexandra's mind that her bitch would be right on time. It was 7:30 am and she was pulling on a stretchy pair of Lycra breeches. She had bought a few pairs during her last trip to London. One of Alexandra's hobbies was equestrian, and these breeches were made especially for that. She decided to not wear anything underneath, knowing that the outline of her pussy would be visible to Adam. He would never see or touch her pussy for the next few months, but would make sure to dress in very dominant looking attire while training him. Her top would come off and her tits would hypnotize him as she emasculated and feminized him. He would never cum like a man again, but she would bring his oh so close as she edged him to near ecstasy.

A pair of black leather riding boots followed the breeches and a tight black corset completed her attire. She had her hair pulled back dramatically in a tight ponytail and she went sexy and sultry with her makeup, accentuating her luscious lips with bright red lipstick. Her fingernails were also a bright red and she had made sure her manicurist had put a little sharpened edge to them. God she thought, "I love this!"

At exactly 8 am, just as she envisioned Adam was knocking on her door. She delayed opening the door for a few minutes, making the bitch wait and wonder, with the added bonus of letting him understand that he needed to be on time but his Mistress didn't give a shit about his time.

"Hello sweetie. Well just don't stand there and gawk, come in."

Gawk indeed. The vision before him was tortuously beautiful and the shivers that were making goose bumps form all over Adam didn't seem to stop. He actually wobbled into the house and it was a miracle he didn't spill the coffee. Everything was moving in slow motion, like when a person has a car accident and time seems to decelerate. He put the coffees and the muffins on the kitchen counter and turned around to take in his lovely Goddess. He was still holding the bag containing his new panties and also his day planner with all of his homework written down.

"Why are there two coffees and muffins Adam?"

He finally found his voice. " Well I figured we could sit out by the pool and enjoy our breakfast together."

It was so swift and calculated he never saw it coming. Her hand exploded against his left cheek with such force that he almost toppled over. He had never been hit that way and as the shock subsided he felt the burning that the slap left on his face.

And suddenly, with a voice and loudness he also had never experienced, Alexandra yelled at him. " Who the fuck do you think you are coming to such conclusions on your own? You are not here to think but are here only to please me. If I wished for you to join me I would have instructed you to do so. And the next time you do not address me as Mistress or Mistress Alexandra there will be hell to pay. Now take the extra coffee and muffin and put it in the garbage bag under the sink. And then get back over here in front of me!"

Adam did as he was told but it was all too much. He was having a sensory overload that was pulling him in all directions and he was just a fucking mess. The days of waiting, the newly found interest in femininity, the God Damn cock cage and the pink thong. Everything was coursing through his mind at once and as he stood before Alexandra he actually began to quietly cry.

Seeing this, and basking in the glory of her training process, Alexandra lovingly took his face in both of her brightly painted thumbs and gently wiped away the falling tears.

"Oh sweetie", her tone immediately had changed. " I am sorry that I made you cry but you have to learn your place with me. I know it's been a difficult few days for you, but you are here with me now. And remember no matter how hard it might seem at times, everything I do with you is for your own good and eventually you will see that. Now be a dear and hand me my coffee and muffin. Put your bag on the counter and make yourself useful by rinsing those plates off that I left in the sink and put them in the dishwasher in an organized manner. When you finish, take off all of your clothes in the other bathroom, except for the sexy panties you must be wearing, and join me in my office. I will take the bag with me and see if you have been a good boi. Do you understand?"

"Yes Mistress Alexandra", he squeaked.

"Now hurry up and don't dawdle. And make sure you knock on my office door and wait for my permission to enter. Beginning now, I need you to absorb all of the rules that will be put forth by me regarding you. If you do that for me I think any punishment will be minimal. Now off you go sweetie."

"Yes Mistress Alexandra."

The muffin and coffee hit the spot and as Alexandra was examining the contents of the bag Adam brought she heard a soft tapping on her office door. Her first session was about to begin and after looking at Adam's daily schedule she was pleased to see that twice-daily sessions would be applied every day. This was extremely important during the training process. As she finished up looking at the last of the panties, she removed her corset and was now sitting in her office chair with one leg sensually draped over one of the arms and her gorgeous breasts were on full display. A pair of handcuffs were swinging back and forth in her left hand, and her right hand was massaging her pussy.

"Come in sweetie."

The look on Adam's face was priceless. Alexandra never tired of using her sexuality to get what she wanted and looking at the soon-to-be sissy literally drooling at the site of her brought a slight smile to her lips.

"Oh my sweetie. I just love those black panties you have on. They really make you look so sexy. Come stand in front of me and let me have a closer look. That's it, come to your Mistress."

Adam was so happy to hear his choice of the black crotch-less panties was pleasing to Mistress Alexandra. As he stood nervously before her she slowly spun him around and attached the handcuffs behind his back.

" Look at me sweetie and listen closely. Today is the first day of your training, We will be having training sessions twice a day for a long time to come. That means you will be able to see me every single day and eventually you will become very proficient in giving me pleasure and being the perfect pet for me. Doesn't that sound wonderful?"

"Yes Mistress," Adam hesitantly answered.

Alexandra continued. " Now I understand that so much of what I am going to put you through is new to you and there will be times that you might think of quitting. But I will not allow that because by you being here, standing in girl's panties and locked in a cute little cock cage, you are now my bitch. And as my bitch, you do exactly what I tell you without hesitation. As of this moment I will not be addressing you as Adam ever again. Sweetie, bitch, slut.....these are just a few names I will use for you."

Alexandra had learned from the past that taking away a young man's name, along with his body hair and any ability to orgasm immediately diminished the submissive's self esteem and made it much easier for her to turn him into a cock-loving bitch.

"You see bitch. Until you can prove to me that you are worthy of a proper name you will be referred to as the aforementioned ones. Now kneel before your Mistress, back straight and your ass cheeks pressing on your ankles. That's a good slut. Now open your mouth for me."

Alexandra reached over to the side and produced a leather penis gag. It was a small variety but it would still have her slut feeling a cock touching the insides of his throat. As she buckled it in place and tightened it she saw a touch of panic in the bitch's face. She had seen this reaction numerous times. The feeling that the small phallus would continue down the esophagus and choke out the newbie.

" Don't worry little bitch. You will get used to having and sucking much larger things than this. So, let's get started. But first, stand up for me and let me take off that chastity device."

Hearing those words suddenly changed Adam's entire disposition. His fear and nervousness now turned to excitement and a wanton lust that had been building for the last four days. As his Mistress took the key and unlocked him, Adam's small cock immediately hardened and poked out through the hole in the panties.

" Well it looks like my bitch is happy to be free. Look at me bitch! Freedom does not mean you are allowed to cum. Understand?"

A muffled Adam tried to answer "yes Mistress."

Before he could get the words out for her to hear, Alexandra had taken the little penis into her mouth again and was licking and sucking it. Slowly using her tongue she licked the underside over and over again. With one hand she had a firm grasp of his tiny balls and Adam looked down and was breathing heavily at the carnal site of those beautiful red nails encasing his testicles and his Mistress's gorgeous red lips wrapped around his shaft. He was so close and so ready to cum. He tried to hold back but soon realized it was an impossible task.

And then, right before he came to fruition his Mistress squeezed his balls with an intensity that he hadn't felt before. His knees gave out and he fell to the floor.

Laughing now, Alexandra looked down at the little slut writhing before her and calmly stated, "Did you really think I was going to let you cum today? I told you freedom did not mean having an orgasm. Now get your panty-clad up here again so we can begin again!"

And on it went over and over again. Every time Adam was near climax his Mistress would ruin his orgasm. When Alexandra thought the bitch could not take it anymore, she grabbed him by his cock and led him into the second bedroom and tossed him on the bed. She had already laid out a variety of anal toys and the second phase of her session was ready to begin.

Once again she wrapped her lips around his little penis and began sucking him. But this time, as she was pleasuring his cock, she began probing the little cunt's asshole with her fingers. This entire exercise, which would last for another two hours, was meant to condition the new submissive to associate sexual pleasure with anal stimulation. As she sucked and licked him, her fingers, wet with his pre-cum would slip into his tight rosebud and manipulate his prostate. At first the virgin boipussy would clench up and try to expel the invader, but after about thirty minutes of probing the little bitche's ass was soon welcoming the ministrations, Adam was moaning uncontrollably and every fifteen minutes or so Mistress Alexandra would ruin another one of his impending orgasms. After about an hour of this, Alexandra grabbed a small dildo, lubed it up and began anally fucking her new slut while all the time playing with its tiny cock. Throughout the training session, Alexandra was verbally abusing Adam.

The first week was all about stripping away his manhood, and Alexandra was making sure this was done in a well-proven way.

"Oh my bitch likes that does he? Just look at you. You really think that little dick could please a woman? From now on we will call it a clitty. Won't that be nice? You really are a horny little cunt aren't you?

On and on it went, her training session seemingly never ending for the broken boi shuddering before her. He was sobbing with a need to cum and also was beginning to push back on the dildo, fucking himself, never satisfied with the ass stimulation he was getting. There were times he thought he might just pass out but the need for more pleasure kept him going. As another orgasm neared, and at the realization that his Mistress would ruin it again, Adam cried and sobbed, drooling copious amounts of saliva through the gag onto the bed. As she tightened her grip on his balls again, a primitive scream erupted around the cock gag. Even gagged as he was, the sound was piercing and the reaction from her slut was music to Alexandra's ears.

It had taken almost five hours of constant edging but finally the bitch was broken completely. Al least for the time being. Adam had indeed passed out from the last ball crunching, and as he lay there unconscious Alexandra extricated herself from the bed and headed to the kitchen for a much-needed glass of water. She returned with a bowl of ice, and seeing her new slut was again awake, she took the bowl and immersed Adam's genitals in it. The feeling was actually soothing to him.

"You have been a good boi for your Mistress. But look at you. What a mess. Let's get you in the shower so we can clean you up and you can remove that unsightly hair that was hiding under the cock cage. And don't worry sweetie, i will be standing outside the shower watching just in case you feel the need to pleasure yourself. Up you go."

Adam sat up and Alexandra removed the penis gag.

"Thank you Mistress, he croaked."

Alexandra smiled at this. She had just put the bitch through five hours of hell and he was still thanking her.

The shower felt wonderful and Mistress Alexandra watched intently as her slut used one of her razors to carefully remove all of the pubic hair which was unable to be shaved because of the chastity device being in place.

After drying off, Adam once again stood before his Mistress naked.

Alexandra had put her top back on and held the cock cage in her hand.

" Well little slut. Time we lock you up again. We can't have you masturbating when I am not with you, correct? Now be a good bitch, get on your knees, and beg your Mistress to lock you up again."

Adam acquiesced and knelt on the hardwood floor. Looking up into his Goddess's eyes he pleaded, " Please Mistress Alexandra. Please, please lock my little clitty up again in the cock cage. Please allow me to be your chastised bitch."

"Good slut. Now stand up, put your hands behind your back and let's get you all secure again before that tiny clitty gets excited."

Once again Adam found himself locked in chastity.

"There we go. Now let's pick out a nice pair of new panties for you to wear."

Alexandra tossed the contents of the bag on the table and grabbed a bright red thong.

"This looks so sexy. Put this red one on and let's take a look at my bitch."

Adam did as he was told and slid the red thong up and over the cock cage. even after hours of edging the little slut felt that all too familiar twinge in his clitty while putting the thong in place.

"Oh yes sweetie you look so cute and femme. Red is definitely a good color for you. Now get dressed and run along home. I will expect you back here at exactly 7 pm. We have to continue with your training."

With eyes downcast, Adam replied, "Yes Mistress Alexandra."

It was nearing 2pm by the time Adam was driving his car down the hill. He was exhausted and wondered how he would summon up the energy to return to his Mistress's house so soon. And had he heard right that she would be training him two times a day in the foreseeable future? If Alexandra had allowed him to orgasm, there was probably a good possibility that he might forego the next evening meeting. But he was so utterly horny and craving more of what she had just did to him that he figured a nap and something to eat would prepare him for the next training session.

Alexandra had moved outside to sit at a table under the umbrella. She was munching on some cheese and crackers and had a nice bottle of wine at the ready. In front of her was a thick notebook and she was busy opening up a new section entitled "Candi'. She was a firm believer in jotting down notes following every session with a slut. While fresh in her mind she found it very important to summarize the event and her ability to write concise notes made it much easier to go back and recount the actions and reactions of her future sissy.

She knew from past experience that the process was tedious and time consuming. But the final outcome was always worth it. The prices she had gotten when selling her sissies in the past allowed her to live the lifestyle she now had. But in order to charge such extravagant amounts for her sluts she knew that a year of training was necessary. Alexandra always scoffed at the accounts she read of an Alpha male being turned in three to four days. The notion was simply ludicrous. Perhaps it was the writer's way of keeping the readers interested, knowing that people were in need of instant gratification and that they would tire quickly and their concentration would wane if the story did not end in a fairly rapid time frame. But it just wasn't possible unless the subject was already experimenting and embracing the sissy lifestyle.

As she concluded her writing, she took a sip of the lovely Bordeaux and sat back contently. She was off to a good start with Adam and his reactions and pleading were just what she expected. There would be more of the same tonight and after one week of twice-daily sessions she would introduce her new slut to her vast array of strap-ons. But before the bitch would get the pleasure of her cock, she would tie him down securely and punish him severely with her cane for earlier transgressions. The cane would become an integral part of training and she already could tell that Adam was the furthest thing from a "pain-slut". Just thinking about it moistened her pussy and she decided to move into the bedroom and use her clit massager to get off.

Kicking off her leather boots and peeling off her riding pants, Alexandra laid back on her bed and grabbed her toy from the nightstand. Small in size but powerful as all get up, she loved slowly building up the vibrations on her hardened clit until she exploded in ecstasy. There were three settings on her clit toy and she started off with the lowest vibration. She was already dripping from her training the bitch so she knew it was not going to take very long to cum. Pressing the toy on the top of her clit Alexandra moaned ever so slightly and basked in the sensual assault on her pussy. Her eyes fluttered closed and a warmth enveloped her entire body. Her breathing was becoming more pronounced and she upped the setting on the vibrator.

"Oh fuck" she thought. "This feels so good and I am so fucking horny."

There was always something to be said for Alexandra controlling the pleasure points on her own self. Years of training sluts to eat her pussy correctly had alleviated some of the frustrations she experienced earlier in life, but there were always areas to be improved upon. She decided years ago that a female mouth was much more pleasing eating her pussy and ass. The difference was palatable and she relished the way a woman orally pleased her. But she also relished getting herself off and soon the setting was up to level three. Her moans eventually turned into screams and her orgasm spewed forth like a volcano. She kept the toy pressed against her clit as she came over and over again, drenching her hand and the sheets. It took some time but Alexandra felt the last of her contractions and felt utterly satiated.