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.

“Stop teasing it and get to sucking, you fucking whore. Wrap those giant dicksucking lips around my cock.” He said to Sindy.

Sindy took this as her cue to get to work. She took his entire shaft down her throat. Lucy had been teaching her to deep throat for the last year or so with bigger and bigger dildoes. She could successfully deep throat a 10 inch dildo, but it wasn’t as thick as Master’s cock. She felt a little pride as her nose hit his stomach that she had taken all of him.

She let her tongue go out of the bottom of her mouth and lick his balls. She heard Lucy orgasm violently as she did this and could see out of her peripheral vision that Lucy continued to finger herself, going for another one. Sindy pulled her head almost all the way off of Master’s cock, just leaving the head in her mouth. Then she went all the way back down to the hilt again.

She heard Master moan, and she knew that he must like it. She continued her assault on his cock, varying up her suction, speed, and even twisting her mouth some as she went up and down. Her manicured fingers were gently caressing his balls, occasionally one of her fingers roamed to tickle his ass. He was really getting into it and his cock was amazingly hard.

Master grabbed her pigtails and started fucking her face. He would push his cock all the way down her throat and then pull it almost all the way out. Then he would ram it forward, back down her throat. He was picking up the pace and really fucking her face hard now. She knew he was close, and could taste more and more precum with every thrust.

“Are you ready to take your Master’s cum, you slut?” he asked.

Sindy couldn’t say much with a giant cock being rammed down her throat violently. And besides, she had always been taught not to talk with her mouth full. She heard Lucy orgasm again, this time even louder.

Master was really fucking her face hard now. He had a death grip on her pigtails, and she couldn’t move off his cock, even if she wanted to. He pulled her all the way down on his cock as she felt the first blast of his cum shoot down her throat.

He pulled back a little, so that his cock was not buried in her throat and she felt the second, third, and fourth blast of his cum on her tongue. Then he pulled out of her mouth entirely and shot the remaining two blasts onto her face.

“You better swallow all of that, you fucking cunt.” Master said.

Sindy showed him the cum in her mouth by sticking out her pierced tongue. There was definitely a mouthful there. Then she closed her mouth and swallowed it all, opening it back up to show Master that she had indeed followed his orders.

Lucy had gotten off the couch and was standing next to her. Lucy scooped the copious amounts of cum off of Sindy’s face with her fingers and told her to lick them clean. Sindy greedily did so, sucking Lucy’s cum covered fingers with abandon. Soon, all the cum was off of her face.

“Now, lick his cock clean, you slut.” Lucy said.

Sindy leaned forward and gently licked and sucked every inch of Master’s sensitive cock clean.

“Look at her little sissy clit, Bob. It is trying its best to get hard in the cage. She must really love sucking your cock.” Lucy said.

Sindy didn’t think it was her place to say that her little sissy clit attempted to get hard when the wind blows these days. After being in chastity for three months, constant porn viewing, daily edging, and being plugged almost 24/7, what did she expect? But she kept quiet, as she knew it would be futile to argue.

“Well, she is going to be getting a lot of it. That is one hot sissy you have there. We will fix the sissy clit in a few moments so that it won’t be trying to get hard again. Once I am done tonight, that thing will be a useless piece of flesh in less than three months. Then she will be 100 percent sissy. I take it that you have a bondage bench somewhere in here?” Bob said.

“Yes, of course. I have to strap her down every day when I edge her. I don’t want her getting any ideas when I take the chastity device off of her.” Lucy said.

“Well, go get her strapped in, and I will make us more drinks.” Bob said.

Lucy led Sindy into their bondage room. She saw Sindy about to say something and cut her off.

“Not a word. I have been telling you this was coming for a long time, and you thought I was bluffing. As you can clearly see now, I am not.” Lucy said sternly.

Sindy was clearly scared now, but also very aroused. She had always been very much turned on when Lucy talked about hormones, but this just seemed so sudden. She laid back on the bench and put her legs up in the stirrups.

Lucy proceeded to strap her legs and feet into them, and then moved up to her arms. Once her arms were secured, Lucy pulled the strap across her chest and buckled it, and then ran a strap across her stomach and buckled it. She was now completely helpless, and in the position she always was when Lucy edged her.

“I don’t want to hear one word out of you, or else I will use the biggest ball gag we have. You know the one, you always complain about how badly it hurts your jaw when I use it.” Lucy said.

Dr. Cornelius walked into the room carrying the drinks and his bag.

“Here’s your drink Lucy. Here’s to a long lasting friendship.” He said as he raised his glass in toast.

As they clinked their glasses together, Sindy felt as if her fate was sealed. She was petrified, but her sissy clit was betraying her. It was as hard as it could get in the CB3000. Lucy came over with the key and took the CB3000 off of her. Sindy’s sissy clit stood at full attention now.

“Well, I can see why you sissified her. There really isn’t much there anyway. I can’t imagine that this little thing ever satisfied you in the first place.” Bob said as he fondled Sindy’s sissy clit.

Sindy almost came off the table when he touched her extremely sensitive clit. She wanted to cum so badly. Maybe if I behave, they will let me cum, Sindy thought.

“Do you have somewhere I can wash up before we get started? Let me just lay out what I will need here.” Bob said as he laid out a surgical pad on the table near Sindy’s feet. This was followed by several instruments placed on top.

“Sure thing. Let me show you the bathroom.” Lucy said as they both left the room.

A few minutes later, they both entered the room. Bob had on surgical gloves and Lucy was finishing her drink.

“Ok, Sindy. This will only take a few moments and then we will be all done. You will be on your way to being a true sissy.” Bob said.

Bob pulled out some alcohol wipes and began swabbing down Sindy’s ass at the incision point. Sindy’s legs were high in the air, and she couldn’t move a muscle. She had never felt more vulnerable. Meanwhile, Lucy was busy fondling her sissy clit—which was as hard as a rock. She began to slowly stroke Sindy’s clit up and down. It didn’t take long before Sindy was about to explode. Lucy stopped all stimulation.

“Now, I am just going to give you a light local anesthesia so that you won’t feel a thing.” Bob said as Sindy felt the needle go into her right buttocks.

Lucy had resumed stroking Sindy’s sissy clit and was talking dirty to her.

“Don’t tell me you don’t love this, you fucking whore. Your little clit has never been harder.”

Sindy was almost to the point of exploding again, and again Lucy stopped stroking her. Sindy could feel her right buttocks going numb.

“While we wait for the anesthesia to fully take effect, I think Sindy should provide a little oral service to me just to pass the time. Lucy, could you help me take my cock out of my boxers? I don’t want to ruin our sterile environment.” Bob said as he laughed.

Lucy pulled Bob’s cock out of his boxers and placed it in Sindy’s mouth. Bob began fucking her mouth in earnest as Lucy resumed the torment on Sindy’s cock. Lucy edged Sindy to the point of orgasm another 15 times before she heard Bob announce that he was cumming down this slut’s throat. Lucy couldn’t remember the last time she had been this aroused.

She could literally feel her juices running down her thighs. She helped Bob put his cock back into his boxers as he walked back towards Sindy’s feet. Lucy could feel Sindy trembling from being so aroused and went back to work on stroking Sindy’s sissy clit. Meanwhile, Bob had picked up his scalpel and the small plastic hormone device and was sterilizing them both.

“This will only take a few more seconds, Sindy. Then you will be on the way to permanent sissyhood.” Bob said.

Bob made a very small incision in Sindy’s right buttocks and slowly inserted the plastic device into the incision. Once the device was all the way in, he cleaned the incision point again with alcohol and closed the small cut with Dermabond.

He then placed a bandage over the cut. Lastly, he pulled out another syringe filled with liquid, wiped down Sindy’s bottom with alcohol again, and injected the liquid into her buttocks. He then declared that he was done. Lucy had been edging Sindy through the entire procedure and she had managed to drive Sindy crazy for another 4 edges. Sindy was shaking in frustration.

“All done now, Sindy. The plastic device inside her will release the maintenance dosages daily. I just gave her a massive dose of the cocktail to get her started on the right foot.

She may feel some nausea and cramping tonight and tomorrow morning, similar to a pregnant woman’s morning sickness from all of the hormones that will be raging around inside her, but that will pass with time. You can discontinue the use of the herbals, because she certainly won’t be needing them anymore. ” Bob proclaimed.

“That is excellent news, Bob!” Lucy said.

“When can I use this sissy’s cunt?” Bob asked Lucy.

“No time like the present. But for now I need to cum, so her mouth is going to be occupied for a bit.” Lucy said as she laughed.

Lucy straddled Sindy’s face and started grinding her soaked pussy onto Sindy’s tongue. Meanwhile, Bob had retrieved the can of Crisco and was lubing his hands thoroughly. Lucy immediately reached her first orgasm, and it was so strong that she squirted a huge stream of cum into Sindy’s mouth.

Bob had removed the enormous plug from Sindy’s ass and was probing it with three fingers, then four. Then he had his fist inside Sindy. Lucy was coming down from an extremely intense orgasm, but seeing Bob’s fist in Sindy’s sissy pussy got her going again almost immediately. She ground her pussy back into Sindy’s face.

She saw Bob begin to work the fingers from his other hand into Sindy’s ass alongside his fist. She had gotten two fists into Sindy before, but it took a long time and it almost sent Sindy through the roof. Bob’s hands were almost twice the size of Lucy’s and she could feel Sindy start to shake again. At this point, Bob had one fist and four fingers from his other hand inside Sindy.

Lucy was so turned on that she came again. Her orgasms were coming in waves from all the excitement. Bob was trying his best to get both hands inside Sindy, and Sindy was moaning uncontrollably onto Lucy’s clit. When Lucy saw Bob’s other wrist buried in Sindy’s ass, she couldn’t believe it. Sindy’s sissy clit was leaking fluid like crazy and a medium sized puddle had formed on her stomach. Bob was working both fists in and out, and it was milking the sissy cream out of Sindy.

This sight (and Sindy’s talented tongue) caused Lucy to orgasm yet again. After about 10 more minutes of this, and 5 or 6 more orgasms for Lucy, Bob announced that he thought that was all the milk he thought he could get out of the sissy. There was a large puddle of cum on Sindy’s stomach. Sindy had been milked before, and while it felt good, she still had a desperate need to cum.

“Why don’t you feed that to her while I go wash up?” Bob said to Lucy.

“Excellent idea.” Lucy said as she got off of Sindy’s face. Lucy picked up a spoon from her bondage kit and began spoon feeding Sindy’s sissy cum into Sindy’s mouth. Sindy gobbled it up greedily and swallowed every drop. Sindy was so aroused from the whole scenario that her sissy clit never went soft the entire time.

Bob came back in the room and asked where the condoms were. Lucy threw him one from her kit and he put it on his cock, which had remained rock hard the entire time.

“Do you have another one? This hot little slut has me really worked up, and I want to put two on so that I can fuck her longer. I don’t want to cum too fast and ruin the moment.” Bob said.

Lucy threw him another condom and said, “You can certainly fuck her as long as you want, but remember that you will always be welcome to fuck her anytime you like. And your friends too.” Lucy said.

Bob put on the second condom and positioned himself at Sindy’s sissy pussy. He rammed his cock all the way in, none too gently. Sindy squealed, as she was very sensitive from the double fisting already. Bob did not hold back and fucked her with abandon. This, of course, got Lucy aroused again and she climbed back onto Sindy’s face and started grinding again. She reached down and began teasing Sindy’s sissy clit again as Bob fucked her harder and harder.

Lucy had lost count of how many times she had cum already, but she managed to cum again another 5 times and edge Sindy another 10 times. Lucy got off of the table and just watched Bob plow Sindy like a wild animal. He had been fucking her for a good 20 minutes or so at this point, when he pulled out. He walked to the head of the table and pulled off both condoms.

“I think all sluts should always taste their Master’s seed. It is just wasted if it is shot into a condom.”Bob said.

“I agree.” Said Lucy.

Bob was ramming his huge cock down Sindy’s throat again and groaned loudly as he shot his load into her mouth.

“Don’t swallow it yet, you whore. Show it to me.” He said.

Sindy opened her mouth and showed Bob the massive load that was in her mouth.

“Swish it around like you would mouthwash. That is a taste you are going to become all too familiar with.” He said.

Sindy swished the cum in her mouth for 15 seconds before Bob told her to swallow it down.

“I think we are done here, for tonight.” Bob said.

“Yes, I think you are right.” Lucy replied.

Lucy went to the small freezer in the bondage room and took out the item that she knew Sindy dreaded most. The ice pack. Sindy knew that if this came out, that she was not going to be allowed to cum, and was going back into the chastity device. Lucy smiled an evil smile at Sindy as she placed the ice pack on her swollen sissy clit. Bob watched and laughed as Lucy held the bag and Sindy squirmed on the table as much as the bonds would allow. After 2 minutes of this treatment, Sindy’s sissy clit had run back into her body like a frightened turtle.

“Bob, would you mind handing me that CB3000 on the table over there?”

“No problem.” He said as he handed it to her.

She slid the chastity device onto Sindy’s shriveled clit easily.

Bob leaned over Sindy and said, “Just think slut, in about a month, you will have trouble getting that little sissy clit hard. And in three months, it won’t ever work again. It will just be a useless piece of flesh.”

Once the lock was in place on the chastity device, Lucy undid the straps holding Sindy in place and helped her up.

“Let’s get those breast forms off of her and take some before pictures of her breasts. That way, when my hormone device starts really working, we will have a basis for comparison.” Bob said.

“We can take them off so you can look at them, but there is no need for pictures. I have taken pictures of her every day in her transition and will continue to do so. It is for our website.” She said.

“You have a website?” Bob asked.

“Yes, it is www.sissificationofsindy.com I will give you a user name and password for free so that you can view her progress from male to what you see now. I think you will be amazed at the transition. We have lots of paying members, and sponsors—which is why Sindy doesn’t need to work anymore. There are lots of videos on there of me fucking her with a strapon, and her being gangbanged, her performing humiliating tasks in public, etc. Hopefully you and your friends can add some videos too, but the hormones are a home run.” she said.

“Excellent. I don’t know why I am just meeting you now. We could have had this slut way further along by now if I had met you earlier. But today is the first day of her new life!” he said as he was examining Sindy’s tender buds. From the herbal estrogen, she had a large A cup or a small B cup, and the doctor was impressed.

He was rolling her pierced nipples around between his fingers and Sindy was moaning loudly. “These herbals you had her on were working far better than I would have imagined. Wait until you see the results from the pharmaceutical grade hormones we just put in her! I have some nipple stretchers we can put in these piercings too. We will have these nipples stretched to at least an inch so they will show through even the most padded bra.”

They exchanged phone numbers and email addresses. Lucy promised to email a user name and password to Bob and told him to begin preparing Sindy’s next adventure with his friends. Bob wholeheartedly agreed and said he would have a better idea of adventures for her after he had already seen how far along she was on the website. Then Bob said that he better be going because it was late and he had to work tomorrow.

He looked into Sindy’s eyes and said, “Bye for tonight slut. But I promise you will be seeing a lot more of me and my cock in the future.” With that, he grabbed her head and shoved his tongue down her throat. He made her kiss him goodbye for at least a minute before he let her head go.

“Thanks again Lucy. I will be in touch.” He said and turned and walked out the door.

“Well, that was certainly a successful meeting, wouldn’t you agree, Sindy?” Lucy asked.

Sindy nodded her head in agreement.

“Let’s go into the bedroom. All of this excitement has me wanting to cum again.” Lucy said.

Sindy followed Lucy into the bedroom.

“Get the strapon extension to your CB3000, cumbreath. I need something inside of me.”

Sindy retrieved the attachment to her CB3000 and was blushing from the name. It was a reminder of the three huge loads of real man semen and the large puddle of sissy cream she had swallowed that night. The device was 9 inches long, and thick. It attached to the end of her CB3000, which certainly gave her Mistress pleasure, while giving her none whatsoever.

When she had the extension attached, Lucy commanded her to her knees and told her to start licking. Sindy could not believe how wet she was. Lucy came almost immediately.

“Now put that cock inside me, slut. I want you to fuck me like your Master fucked you.” Lucy demanded.

Sindy put the tip of the large dildo at the entrance to Lucy’s pussy. She had planned to gently ease it in, to let Lucy get used to it, but it was not necessary. Lucy was so wet that it slid right in. Sindy began to rock back and forth, fucking Lucy with the strapon. She could feel nothing, but she could tell it was driving Lucy wild with lust.

“Fuck me harder, slut.” Lucy growled.

Sindy was really fucking Lucy hard now, pushing the cock all the way in to the hilt, then pulling almost all the way out and ramming it home again. She could tell that Lucy was cumming yet again, but she knew better than to stop until Lucy told her to. Lucy had meanwhile pulled Sindy’s bra down and was tugging sharply on Sindy’s nipple piercings and rolling her nipples with her fingers. Sindy was moaning loudly, as was Lucy. Lucy was cumming in waves now.

“Everything I have done to feminize you so far..Oh God, yes, right there…has turned me on so much…Oh damn, that’s it…But tonight has been the best so far…Don’t stop, you fucking whore…You are now a full fledged sissy bitch…oh yesssss…my sissy bitch…ahhhhhhh…to be used like I see fit…oh damn, there’s another one…with a now useless cock…oh my God, that’s the spot….and your tits growing bigger and bigger…yessssss…and when they stop growing from the hormones…oh, fuck that feels so good…I am going to give you implants so big that you can’t even see your feet…ohhhhh…more tattoos…more piercings…oh, shit…with Bob’s help, we are going to make you into the biggest sissy slut cum dumpster there ever has been…Oh, my God!

Lucy pulled away from Sindy rapidly, her pussy still vibrating from cumming so many times in a row. Sindy had worked up a little bit of a sheen from pounding Lucy so hard.

“Damn that thing is good. It touches all kinds of spots that your little sissy clit never could.” Lucy said.

“I am going to do something tonight that I never thought I would do again. I am going to let you cum. Do you want to cum, you little cum guzzler?”

“Yeth, mithress.” Sindy said emphatically.

“I don’t know why. Maybe I am getting a soft spot, or maybe I feel sorry for you since this probably will be the last time you ever cum again in your life. But regardless of the reason, I am. Go get the eggplant.” Lucy said.

Sindy almost tripped because she was running to get the eggplant and the Crisco so quickly. The eggplant was one of their sex toys that they had nicknamed because of its shape’s resemblance to an eggplant. The top part of the rubber toy was a mere 7 ½ inches in circumference, but it quickly widened to a more hearty 14 inches in circumference at the bottom. The toy was about 11 inches in length. Sindy returned with the eggplant and the lube.

“Get started lubing that up, and I will be right back.” Lucy said.

Lucy returned with a small stool and placed it on the floor. She pressed record on the video camera on the tripod in the room.

“Now, attach your toy’s suction cup base to that stool, you fucking whore.” Lucy said.

Sindy complied.

“Ok, if you want to cum tonight, you have to get that all the way inside you. I want your butt cheeks touching the stool.”

Sindy’s hopes were slightly dashed. She had never been able to get the eggplant all the way in before. She always got almost all the way, with only about an inch or an inch and a half left to go, but could go no further. She knew she had to accomplish it tonight. She may never get this opportunity again. She was going to do her absolute very best.

Sindy removed her panties. She was already dripping out of the end of her CB3000 again. Lucy scooped up the drippings from the tip of the chastity device and promptly put her finger in between Sindy’s thick, puffy lips. Sindy lubed her sissy pussy and squatted over the stool. The tip of the toy easily entered her after the double fisting she had already endured that evening. She gradually lowered herself down on the toy. Lucy was standing in front of her now, her pussy just inches away from Sindy’s tattooed and collagen plumped lips.

“Don’t touch it or lick it. I just want you to smell the pussy that owns your pathetic sissy self as you open yourself up for me with the eggplant. Take a deep breath and inhale me. Mmmm. You smell that pussy? It owns you. There is no turning back now. I am going to turn you into an even more pathetic sissy than you are right now. Do you want that?”

Sindy nodded as she was trying to get more and more of the eggplant inside her. She had about 2 more inches to go, but it was the most challenging and widest part.

“I can’t hear your fucking head rattle. Say it!” barked Lucy.

“Yeth, Mithress. Pleathe turn me into an even more pathetic thithy than I am right now.”

“Do you want bigger tits?”

“Yeth Mithress. The biggeth that money can buy.”

“Do you want me to line up scores of me to fuck your mouth and sissy pussy?” Lucy asked.

“Yeth, Mithress. Pleathe line up gangbangth of 20 and 30 real men to cover me in their cum.”

Sindy was leaking profusely out of the tip of the CB3000 now. Lucy collected it in the palm of her hand and made Sindy lick it up. Sindy was really close to getting the eggplant in now. She only had about a half inch left to go, the furthest she had ever been. Lucy removed the key to the CB3000 from around her neck and unlocked the lock on the chastity device. She removed the device as Sindy continued to bounce up and down, grunting and groaning from the monstrous invasion. Lucy started stroking Sindy’s half hard, half flaccid sissy clit.

“The anti androgens in your booster shot must already be kicking in, you little cum dumpster. Normally this little thing would already be rock hard.” Lucy said as she continued to stroke. “Remember, you don’t get to cum unless you get it all the way in. Do you want some help?”

“Ughhh. Yeth pleathe mithress. It’th tho big.” Sindy said.

Lucy stood up behind Sindy at the stool and started pushing down on Sindy’s shoulders.

“Take it all you little cunt.” Lucy said.

“ahhhhh….tho tho deep, Mithress.”

“Just a little more, bitch.” Lucy said.

Lucy pushed down more and Sindy grunted one more time. This time more loudly. She had gotten it all in as she felt her butt cheeks touch the stool. Lucy walked around the stool and crouched in front of Sindy.

“Very nice, you fucking whore.” Lucy said as she stroked Sindy’s half erect clitty. Sindy was rocking up and down on the monster as Lucy stroked her even more.

“This thing won’t even get hard anymore. Those hormones are already kicking in! I love Dr. Cornelius!” Lucy said.

Sindy was getting very close to cumming.

“I’m about to cum, Mithress!”

“Good sissy. Let all of that nasty sissy cum out. It will be your last cum ever so you better enjoy it!”

Sindy’s clit, although not hard, was dribbling massive amounts of cum. Lucy was catching it all in her hand, in disbelief at the quantity since Sindy had already been milked earlier tonight. Sindy was shaking uncontrollably from the intensity of the orgasm and pulled up off of the monster in her sissy pussy.

“Here you go, cumbreath. You know you have to lick it all up now.” Lucy said, holding her hand up to Sindy’s mouth. Her palm was filled with the milky white sissy cream.

Sindy gobbled it all up, barely able to stand because her legs were so weak from all of tonight’s activities.

“I think that is enough for tonight. Tomorrow is the first full day of your new sissy life! Let’s get cleaned up and get some rest. But first we have to reapply your CB3000. I don’t even think we will need the icepack this time, you limp dicked little sissy. We will probably have to buy a smaller chastity device now.” Lucy said as she laughed and turned off the video recorder.

They cleaned up, and got ready for bed. Sindy lay in bed wondering what the future might hold for her—she was worried, but oddly very aroused as she fell asleep

Sindy awoke the next morning with her babydoll nighty completely soaked in sweat. She thought this odd because Lucy kept the bedroom at a brisk 65 degrees and the ceiling fan on high. She was also feeling extremely nauseous and her entire body felt like one big cramp.

Lucy entered the room carrying a glass of Gatorade and something else in her other closed hand.

“How are you feeling, sissy?” Lucy asked.

“Not tho good Mithress.” My whole body acheth, and I am tho hot.”

“Well, the good doctor said this might happen. That just means the sissy juice is really kicking in now!” Lucy said. “Here, take these two Midol. They should help with the cramping.” Lucy said as she held out two pills.

Sindy took the pills and was surprised that Lucy was reaching to unlock her CB3000.

“And this will help with the nausea.” Lucy said as she unlocked the device and took it off. She then fastened cuffs to Sindy’s wrists and ankles and connected them to the D rings on the bed frame. Sindy was spread eagled, with her legs up in the air similar to her position in the stirrups last night. Lucy lubed her fingers and Sindy’s sissy pussy and then started probing. She inserted what looked like a large pill into Sindy’s open sissy pussy.

“This is a phenergan suppository and should help with the nausea.” Lucy said as she began to massage Sindy’s sissy clit with one hand and massage Sindy’s prostate with the other.

Sindy moaned as Lucy stroked her flaccid sissy clit. It felt so good, as it normally did when Lucy stroked her, but her sissy clit refused to harden no matter how much Lucy stroked it. Lucy continued to roll the soft piece of flesh between her fingers as she talked

“One of the uses of the anti androgen the doctor gave you is to chemically castrate male sex offenders. So I wouldn’t count on this little thing getting hard ever again. The other advantage is that without all of those nasty male hormones coursing through your system, the estrogen will begin to work more faster. You will be a full-fledged sissy girl before you know it. Do you want to be my sissy girl?” Lucy asked as she continued to stroke Sindy’s flaccid member and massage her prostate with her fist.

“Yeth Mithress.”

“Yes what?” Lucy demanded.

“I want to be your thithy girl.”

“Say it louder then.” Lucy demanded.

“I want to be your thithy girl.” Sindy said a little louder.

“Louder.”

“I WANT TO BE YOUR THITHY GIRL!” Sindy almost shouted.

Lucy proceeded to bring Sindy to the edge of orgasm over and over again throughout the next 45 minutes. She lost count at about 20 times, never letting her cum. Sindy was a sobbing wreck at this point, and leaking precum onto her stomach.

“How are the cramps now, better?” Lucy asked, spooning the sissy cream into Sindy’s mouth.

“Yeth, mithress. Much better.”

“Good. Now, which cock do you want me to use to fuck you? Do you want Jenna?” Lucy asked laughing. Jenna was the Jenna Jameson strapon that was the first one they had ever used. It was also the smallest, being only about 6 inches long.

Lucy knew that Sindy wouldn’t pick that one, because she could not even feel it anymore and it gave her very little pleasure. Her sissy pussy had been so stretched out at this point from the fists, cocks, giant plugs, and enormous strapons that had been inside her.

“Pleathe fuck me with the giant black one, Mithress.” Sindy said, referring to a rather large specimen that was 9 inches in circumference and 11 inches long.

Lucy stood up and started strapping on this black monster. She always loved fucking Sindy with large strapons. For one thing, she loved making the little bitch submit to huge cocks inside her—it turned Lucy on so much. The other thing was that the base of the strapon always rubbed against her clit while she was pounding away at Sindy. Lucy was extremely turned on at the moment and needed to cum. This monster would serve that very purpose.

“Are you ready, you little cum dumpster?” Lucy asked as she positioned the tip of the black monster right at the entrance to Sindy’s sissy pussy.

“Yeth, Mithress. Pleathe fuck me ath hard ath you potthibly can.” Sindy said.

“Your wish is my command, whore.” Lucy said, as she rammed the 11 inches of thick black cock balls deep into Sindy’s eager fuck hole. After three strokes of going all the way into Sindy’s pussy and all the way back out, Lucy was already cumming for her first time. However, she did not stop. Instead, her orgasm only made her intensify her thrusts.

“Take my big black cock, you little slut. You feel me cumming inside your pussy? Shooting my hot sticky black cum all inside your cunt? I bet you want a real black dick in there. One that shoots so much man cream inside you so that it is leaking out of your cunt for days.

You want that don’t you, you little bitch?” Lucy was really leaning into the strokes now, pulling the monster all the way out and ramming it home again and again. Her orgasms were coming in waves now, so many that it felt like one giant continuous cum.

“Maybe Dr. Cornelius can bring some of his friends over later, so that you can have one cock in your mouth, and another in your cunt, and another covering your tits with cum.” Lucy said as she started tweaking Sindy’s pierced nipples with her fingers in between thrusts.

It was all too much for Sindy. She was extremely aroused from the edging, verbal humiliation, nipple stimulation, and the pounding. She could feel the sissy orgasm building inside of her, but her sissy clit remained flaccid. Lucy continued to pound away, even harder than before.

“Is that what you want, cunt? To be covered in hot, creamy cum? Maybe I will take you to the glory hole, and chain you there for four hours or so—sucking every cock presented to you through the hole. Sucking so much cum out of stranger’s cocks that your stomach gets distended.” Lucy said, thrusting harder and harder.

Sindy couldn’t hold back any longer as she felt the sissygasm release. It was unlike any orgasm she had ever experienced. Every nerve in her body seemed to be firing at the same time. All of her previous orgasms in her life had been focused upon her cock and ejaculating.

This one was more of a whole body orgasm, so much so that she didn’t even realize that a large quantity of sissy cream had dribbled out of her sissy clit. Lucy continued to rock back and forth, slower now than before, but still pushing the monster all the way in and pulling it all the way back out. She wanted to make sure that Sindy remembered this sissy orgasm for a long time.

“There you go, sissy. Let all that nasty sissy cream out. It just makes you more girly.” Lucy said as she started scooping the cum off of Sindy’s stomach and put it into Sindy’s panting mouth. “That’s the only way you will ever get relief again, baby. I sure hope you enjoyed it.” Lucy said as she pulled out of Sindy’s sissy pussy with the monster. Lucy then reapplied the CB3000 to Sindy’s shriveled clit.

“There. Now that we have all of that taken care of, I need to give you something to wash down all of that sissy cream. If you spill one drop of it, I promise to have you tied to the bondage bench for the next two hours while I take the top layer of skin off of your ass with my flogger. Understood?”

Sindy nodded that she did as Lucy positioned herself with knees on either side of Sindy’s face. Sindy could see that Lucy was already soaked from cumming so many times. Lucy lowered herself onto Sindy’s face.

“Now lick, you worthless cunt. I need to keep you around here for something, since that little pathetic piece of flesh no longer works.”

Sindy began lapping at Lucy’s soaked pussy, paying special attention to her clit. Lucy was grinding away at Sindy’s face and in no time she was approaching orgasm. It turned her on so much to sissify this little bitch, she thought as she came in a violent orgasm. She raised off of Sindy’s face for a second, to recover her senses. Then she lowered back down onto Sindy’s face.

“You better not miss one drop, understood?”

Lucy began to release her morning urine into Sindy’s waiting mouth. Slowly at first, and then building into a much stronger stream. She could hear Sindy gulping to try to keep up, and it pleased her greatly. She had a really full bladder and knew that Sindy’s stomach would be very full when she was done.

Lucy continued to piss a hot stream of urine into Sindy’s mouth, not slowing up. She somewhat hoped that Sindy would miss a drop so she could have an excuse to spank her for a few hours. As she finished up, she was again aroused.

“Lick it clean, bitch.”

“Now you have me turned on again. Keep licking. I want to cum again.” Lucy said.

Sindy’s tongue and jaw was getting tired, but she knew better than to stop. She continued to lick, moving her tongue rapidly. Lucy was grinding onto Sindy’s face now, almost painfully to Sindy’s jaw.

“Oh, God. Yes, lick it you little sissy. Make me cum again!”

Lucy came again, also a very powerful one.

“I love cumming this much early in the morning. Now get your ass up. We have a big day today. Dr. Susie is coming over for your hypnosis session, and you have to do your hour long aerobics workout. And maybe Dr. Cornelius and some of his friends might be coming over later. So get your ass in gear. Get into the bathroom, get cleaned up inside and out. I want you to use the two quart enema bag this morning.”

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