Sindys Undoing

Lucy had been following Dr. Cornelius for months now. He had been one of the 20 endocrinologists in Orlando on her list when she started this quest, and he seemed to her to be the most likely candidate to help her with her goal. She had ruled out almost all of the others after delving into their backgrounds. From what she could tell in her research, Dr. Cornelius seemed to be the perfect person to help her in completely feminizing and sissifying her live in sissy, Sindy.

She already had Sindy living in 24/7 sissification, always wearing nothing but female clothes, finger and toenails painted; ears , tongue and nipples pierced; female tan lines; constantly in chastity; speaking in feminine voice and lisp; fully hairless from the eyebrows down from laser hair removal; eyebrows plucked into a thin arch; a tattooed tramp stamp that said "sissy cumslut"; plugged daily with monstrous butt plugs; permanently tattooed lipstick, eyeliner, and eye shadow; collagen lip injections; received weekly hypnosis to reinforce sissy slut status; fucked multiple times per day with enormous strapons that would make any hooker cry; and a litany of daily exercises that were so humiliating that Sindy thought she would die from embarrassment. However, Lucy wanted to take it up a notch. She wanted Sindy to start female hormones and anti androgens, and Dr. Cornelius was part of her plan to help achieve this goal.

Through the course of her investigation, she followed Dr. Cornelius for months. She found out that in addition to being a top rated endocrinologist that specialized in helping transgendered patients transition into womanhood, he was also a bit of a deviant. He frequented BDSM clubs and gay clubs. She found out that he was not only bisexual, but was also a top notch Dominant in the BDSM community. This of course was not listed on his practice's website, but she found this out through months of painstaking investigation.

Tonight, she watched him across the bar of the Blue Martini. She had already decided that tonight was the night, and she wanted to get to him before he took home one of those bar sluts she had seen him talking to over the course of the evening. Lucy was dressed in business suit, much like the happy hour crowd that was assembled. However, she had replaced the top with one much more revealing than for which the suit was originally designed. Her ample cleavage was on display—which was completely her goal since she had witnessed over the months that Dr. Cornelius was definitely a boob man. She made her way around the bar and chose a stool about 4 down from the doctor. She had just caught the bartender's attention and was ordering a Stoli on the rocks with a splash of cranberry when she felt his presence in the stool next to her.

"Hey there, I don't think I recall ever seeing you in here before." He said.

"I come in here occasionally. I don't live far from here." She replied.

They exchanged the typical bar pleasantries, talking about jobs, other people at the bar, etc. for the next 25 minutes or so. Both were very good with the light sexual innuendo. Every time she vaguely referenced sex, he gave it back to her as good as she gave. After they had finished their third drink, their inhibitions were down and the light sexual innuendo turned to that much less thinly veiled.

"Can I ask you a question?" Lucy asked.

"9 ½ inches." Was his response.

"Well, that isn't what I was going to ask, but that is certainly useful information." She replied with a gleam in her eye. She had heard this response before in her life, so it didn't catch her totally off guard.

"Do you think you can handle it?"

"Oh, I can handle it. I just don't think you can handle me." She said.

"Why do you say that?" he asked.

"I enjoy some of the more non-traditional things in life." She said.

"Well, now you have me intrigued. Do tell."

"I wouldn't want to scare you off." She said as she laughed.

He laughed back.

"There isn't anything you could tell me that would scare me off. I have probably done far worse than you could ever dream of." He said.

"I doubt that. But let's hear something that you think would scare me." She said. She was enjoying this game of cat and mouse, one that she never lost.

"Well, I do enjoy an occasional foray into BDSM. " he said.

"I take it from your forward personality that you are a dominant?"

"How did you ever guess?" he asked.

"It takes one to know one." She laughed.

"You are a dominant as well? You look so innocent. Are you into the Orlando BDSM scene?"

"I haven't ventured into the scene much..yet. I have a live in submissive that I want to expose to it." She said.

"Oh really? Male or female sub?" he asked.

"Somewhere in between." She replied.

"You have a transgendered sub?" He asked.

"Well, that isn't 100 percent accurate. He started out as my boyfriend. When we started experimenting with BDSM, he was just my male sub. Over time, I developed a taste for forced feminization. Now he lives as my sissy full time. I am feminizing him a little more each day, and there is hardly any male left. He, or should I say she, is in chastity all of the time now."

"Have you started her on hormones yet?" he asked.

"Not the real ones. But she knows it is coming. She has taken about 5 months of my birth control pills in addition to herbal estrogen for about a year. The pharmaceutical hormones are the next step in her feminization."

"You can get some results with herbals, but they are nothing compared to the results you can get with pharmaceutical grade hormones." He said.

"And you know this from experience?" she asked, feigning ignorance.

"Well, for one thing it is my job. I am an endocrinologist. For another thing, I have taken a special interest in sissies and males transitioning to females. The ones that are forcibly feminized are of particular interest to me. I have trained a few sissies in my time and could assist you with her training." He said.

"Oh, well, you definitely should meet Sindy then. She is definitely being forced further than she ever thought she would go. I have just done it a little at a time, where now this is just normal for her. I doubt she would even recognize herself or how far she has come in the last three years. And I would take any assistance that you could offer in helping her to be a better sissy."

"That sounds fantastic. I would love to meet her and help you with her training. The hormones are a necessity though. I have found that they truly help a sissy realize their true nature and they realize there is no chance of ever going back to their male life. There is nothing quite like the thrill of injecting the first dose of hormones into a reluctant sissy."

"That could certainly be arranged. How about tonight? I love to make her blow random men. She has really gotten to be quite the accomplished cumslut." she said with a smile.

"She sounds perfect. Let's get out of here. I'll follow you." He replied peeling off a wad of twenties and throwing them on the bar.

Lucy was excited. She had known Dr. Cornelius was into the wilder side of life, but she had no idea that he had trained sissies before. This was turning out far better than she could have ever imagined!

She drove slowly to her house so that Dr. Cornelius could easily follow her. She pulled into her parking spot at the house and Dr. Cornelius parked next to her. She could see him pull out a bag from his car and they walked to the door of the house. She unlocked the door and went inside as Dr. Cornelius followed her up the stairs.

Once they reached the top of the stairs, they could see Sindy sitting at the desk behind the computer. She was wearing a very sheer, pink ruffled nightgown, pink thigh highs, sheer pink panties, and pink stiletto heels. The shelf bra in the nightgown was struggling to contain the massive EEE false breasts inside. Her bleached blonde hair was styled in pig tails and her permanent eye liner was accentuated with coral pink eyeshadow. Her permanent lip liner was touched up with coral pink lipstick and lipgloss, which looked very nice on her plump, collagen induced lips. Her cheeks were also colored in pink blush. She had a deep tan, which contrasted nicely with the pink nightgown. The pale white skin from her bikini top tanlines was a stark contrast to the dark tan she had.

On the computer screen was a video playing of a large, muscular, hairy man with both of his ample fists buried inside of a sissy's ass. The sissy's screams coming from the computer were permeating the room. Sindy looked up from the computer screen to see Dr. Cornelius and Lucy—and although she didn't look surprised to see a man standing there, it was obvious that she was highly embarrassed. Her pink cheeks immediately filled with more color. One of the aspects of her sissy hypnosis training was that she would always be extremely aroused when in the presence of real men and when forced to perform deviant sexual acts on them, but would also be extremely humiliated and embarrassed by being forced to do so.

"Sindy, I would like you to meet Dr. Cornelius. He has offered to assist me in your sissification training. Come over here and meet him." Lucy announced.

Sindy stood up from the computer desk and walked very daintily over to Dr. Cornelius. Her CB3000 was very visible through her sheer pink panties as she minced over in very small steps, careful not to topple over from the very ample and very heavy breast forms in her nightgown and the ultra high stiletto heels.

"I am very pleathed to meet you." She said in a very breathy, very sissyish voice as she extended her right hand to Dr. Cornelius with the wrist bent.

He took her hand and gently kissed the back of it, noticing the perfectly manicured one inch nail extensions, in coral pink with a French manicure.

"The pleasure is all mine." He said.

"Sindy, why don't you fix us some drinks? The usual for me. Dr. Cornelius, what will you have?" Lucy said.

"Scotch on the rocks, please."

"Sindy, you can make yourself an appletini. Dr. Cornelius, why don't we get more comfortable on the couch?" Lucy said.

Lucy and Dr. Cornelius sat on the couch as Sindy minced over to the bar to make the drinks. Dr. Cornelius noticed the massive butt plug inserted in Sindy's ass through the sheer panties.

"Do you always let your sissy watch porn when you are away?" Dr. Cornelius asked.

"Well, I don't let her. I require it. She is required to watch at least two hours per day during the weekdays, and three hours per day on the weekends. I pick the genre and she has to find a certain number of videos per day of something she thinks I will find hot in that genre. If I don't think what she has sourced hot enough, she gets punished. I have found that it makes her chastity much more unbearable. Additionally, I bring her to the edge of orgasm over and over again for a minimum of 45 minutes per day, never letting her cum. She hasn't cum in over three months now. She gets punished if she fails and accidentally cums."

Sindy returned with a tray of drinks and was clearly embarrassed by the subject matter being discussed. She gave Lucy and Dr. Cornelius their drinks.

"Sindy, please show Dr. Cornelius what your punishment was the last time you failed during an edging session."

Sindy placed her appletini on the coffee table and turned around. She lifted her sheer pink nightgown and slipped her manicured fingernails into the strings on the side of her sheer pink panties. She slowly lowered them as she bent over. Her tramp stamp, which read "Sissy Cumslut" in ¾ inch hot pink cursive letters became visible to Dr. Cornelius.

"Excellent work, Lucy! That is so hot. May I?" Dr. Cornelius said as he reached towards Sindy's ass.

"Absolutely. Be my guest." Said Lucy.

Dr. Cornelius rubbed his hand across Sindy's tramp stamp, and lowered her panties even more. He was caressing each of her ass cheeks and his hand made its way to the monstrous plug in her ass. He felt the vibrations coming from the plug as he pushed it deeper in Sindy's ass. He could hear Sindy moan loudly as he did so.

"This little slut loves to be filled, doesn't she?" he asked.

"Oh yes. You should see some of the dildoes I fuck her with. She also loves to be fisted. She loves having her hole filled because that and her sensitive nipples are currently her only form of pleasure she is allowed. The last time we got to the three month point, I think she would have fucked a horse if I had let her, just to try and get off. Between the three months in chastity, the daily edging, and the constant porn watching, she was a sobbing wreck begging to cum daily."

"Well, you wait until you start her on the real hormones. Her nipples will become even more electric and she will go through the roof when you touch them, much less when you put nipple clamps on them." Dr. Cornelius said, all the while pushing the plug deeper into Sindy and letting it slide out a little each time. Sindy was pushing back onto the plug, just short of bucking wildly at this point. Her groans were becoming more insistent.

"Sindy, stop being such a slut and go get Dr. Cornelius and I another drink." Lucy said.

"Please call me Bob. The slut can call me Master." Dr. Cornelius said.

Sindy pulled her panties back up and minced her way over to the bar with their empty glasses. She was getting worried because she could tell they had already had an ample amount to drink before they got here. Lucy was always more strict and dominant when she had been drinking. The tramp stamp on Sindy's back had been as a result of one of those evenings. And this guy she brought home seemed to be even encouraging her more—he kept mentioning hormones! Sindy was worried, but also aroused. She felt a big glob of precum slide out of her CB3000. She took a napkin from the bar and tried to clean it up before they saw that this was arousing her.

"Stop playing with yourself and bring us our damn drinks! And they better not be as weak as they were last time. Put some damn liquor in them this time!" Lucy yelled.

"Once you start them on hormones, they stop trying to play with themselves so much." Dr. Cornelius said.

Sindy heard this and trembled, but she knew she better get the drinks to them soon or risk Lucy's ire.

"Well, Bob, that is precisely my intention. I just need to obtain a supply and I will get them started as soon as possible." Lucy said.

"What if I told you it was possible right now?" he asked.

"I would say bring it on. And you would certainly have free use of her any time you desired for your troubles." Lucy replied.

"Well, I have developed something in my practice that is not quite FDA approved just yet. It is a device similar to the Norplant birth control device. It slides in right under the skin. I can have it done in just a few minutes. It time releases estradiol, finasteride, and spironolactone daily. 10 days of the month it adds progestin into the mix. What do you think?" he asked.

"Let's do it." She said.

"I need you to be 100 percent sure. This particular device lasts 3 years. Once it is in for about a month, the effects are really irreversible. These are not your typical hormones, they are much more potent than what you can get from other doctors." He stated.

"Oh, I am very sure. I have been wanting this for a very long time, and it is just lucky that I met you. Sindy has known for some time that I was going to put her on real hormones. She just maybe didn't know that it would be this soon. When would be the earliest that you could do it?"

"I can do it right now. But I would like to test out her mouth first, if that is ok with you." He said this as Sindy walked over with the drinks. It seemed like her cheeks had constantly been red since this man walked into the house.

"Sindy, please help Bob take his clothes off." Lucy said.

Bob stood up, threw back the drink of scotch and waited for Sindy to put the other drinks down. He stood there as she helped him take his shirt off. He was actually in very good shape, and had an extremely hairy chest.

"What are your thoughts on kissing sissies, Bob?" Lucy asked.

"I love it. It is really good foreplay." Said Bob.

"Well, Sindy does not like it at all. But I make her do it to show her who is in charge. Why don't you give her a kiss or two?" Lucy asked.

Bob pulled Sindy's head towards him and shoved his tongue in Sindy's mouth. He could tell from her body language that she did not like it. He could feel her tongue piercing with his tongue and thought that it was going to feel very good on his cock in a short amount of time.

"Sindy, run your fingers through the hair on his chest as you kiss him. If you don't start showing some enthusiasm, things are going to get very bad for you." Lucy said.

Sindy could hear in Lucy's voice that she was getting drunker and drunker and knew that she better obey. It was hard to concentrate, because Bob was pushing the plug in and out of her as his tongue explored her mouth. Her manicured hands roamed Bob's hairy chest.

"See, Sindy. That is what a real man's chest looks like. Not your hairless body. You never really were much of a man anyway though. I always knew you were a sissy. Now, work your way down his chest with your mouth. I want you to pay particular attention to his nipples." Lucy said.

Sindy moved her way down, at least happy that she didn't have to kiss Bob anymore. But the thought of kissing and licking his hairy nipples was not that much more appetizing to her. She licked and sucked each one, not enjoying the massive amount of hair he had and the feeling of it on her tongue and in her mouth.

"This sissy is making me hot, Lucy." Bob said.

"Well, let's do something about that. Sindy, take Bob's pants down and start working on his cock." Lucy said.

Sindy unbuttoned Bob's pants and then unzipped them. She pulled them down along with his boxers and was greeted with a truly massive cock. It was only partially hard, and it was at least 8 ½ inches long. But the truly impressive thing was its girth. It was probably about 6 inches around and had a huge mushroom shaped head. Sindy had never seen one this big, and this thing wasn't even completely hard yet.

"Generally, I like my sissies to lick my ass a bit before they blow me. Do you mind, Lucy?" Said Bob.

"Not at all. Sindy, let's see how far you can get your tongue up Bob's ass!" Lucy barked.

Sindy's stomach turned over. This was by far the thing that she was dreading the most. She made her way under Bob's balls, licking them and gently sucking until her tongue was at his ass. It was as hairy as his chest, if not hairier. She tried to think of something else as she started licking.

"Very nice, sissy. Now do as your mistress says and work your tongue in deeper." Bob said.

Sindy did so as Lucy watched. The further Sindy stuck her tongue up Bob's ass, the harder his cock got. Lucy was watching as his impressive cock grew to full mast. It was at least 9 ½ inches long.

"Well, he wasn't lying about that part." Lucy thought.

"Now, sissy, work your way back to my balls." Bob ordered.

Sindy was tonguing his balls and his enormous cock was laying on her forehead. Meanwhile, Lucy had pulled up the skirt to her business suit and removed her panties. She began fingering herself uncontrollably.

"Now sissy, you get the reward. Beg me to suck my cock." Bob said.

"Pleathe thir, can I thuck your matthive cock?" Sindy said seductively, the giant ball in her tongue causing her to lisp dramatically.

"Of course. I am glad you asked. But we are going to need to work on your begging skills."

Sindy dove right into her work. She definitely wanted to show enthusiasm to this task so that she didn't have to go back to tonguing his hairy ass. She licked all the way up the enormous shaft, coming to the giant mushroom head. She greedily licked the large drop of precum that had formed at the tip. She played with this in her mouth a bit for show, and then licked all around the top of the head. She slowly took the top of the head in her mouth and applied gentle suction.