Richard had been following Dr. Cornelius’s research for months now. He had been one of the 20 endocrinologists in Orlando on his list when he started this quest, and he seemed to him to be the most likely candidate to help him with his goal. He had ruled out almost all of the others after delving into their backgrounds. From what he could tell in his research, Dr. Cornelius seemed to be the perfect person to help him in completely feminizing and sissifying his live-in sissy, Jersey.
Richard already had Jersey living in 24/7 sissification:
- Wearing nothing but female clothes
- Fingernails and toenails painted in hot pink paint
- Piercings
- Ears
- Nose, bullnose hoop
- Tongue, for his pleasure
- Nipples
- Prince Albert to prevent chastity removal
- Guiche
- Female tan lines
- Chastity
- Hairless from the eyebrows down from laser hair removal;
- Eyebrows plucked into a thin arch
- Tattoos
- “Anal Slut” tramp stamp on her upper butt
- “sissy clitty” above the locked chastity
- Permanent lipstick
- Permanent eyeliner
- Permanent eye shadow
- Collagen lip injections
- Plugged daily with monstrous butt plugs
- Receives daily hypnosis to reinforce sissy slut status
- Fucked multiple times per day with an enormous fucking machine that would make any hooker cry
- A litany of daily exercises that were so humiliating that Jersey thought she would die from embarrassment.
- Placed on birth control to induce female hormones
However, Richard wanted to take it up a notch. He wanted Jersey to start female hormones and anti-androgens, and Dr. Cornelius was part of his plan to help achieve this goal.
Through the course of his investigation, he followed Dr. Cornelius for months and he 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. he 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 he found this out through months of painstaking investigation.
Tonight, he watched him across the bar of the Blue Martini. he had already decided that tonight was the night, and he wanted to get to him before he took home one of those bar sluts he had seen him talking to over the course of the evening. Richard was dressed in a business suit, much like the happy hour crowd that was assembled. He made his way around the bar and chose a stool about 4 down from the doctor. He had just caught the bartender’s attention and was ordering a Stoli on the rocks with a splash of cranberry when he felt his presence on the stool next to his.
“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,” he replied.
They exchanged the typical bar pleasantries, talking about jobs, these people at the bar, etc. for the next 25 minutes or so.
“Can I ask you a question?” Richard asked.
“I enjoy some of the more non-traditional things in life,” he said.
“Well, now you have me intrigued. Do tell.”
“I wouldn’t want to scare you off.” he said as he 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.” he said. he was enjoying this game of cat and mouse, one that he never lost.
“Well, I do enjoy an occasional foray into BDSM. ” he said.
“I take it from your forward personality that you are dominant?”
“How did you ever guess?” he asked.
“It takes one to know one.” he laughed.
“You are dominant as well? 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,” he said.
“Oh really? Male or female sub?” he asked.
“Somewhere in between,” he replied.
“You have a transgendered sub?” He asked.
“Well, that isn’t 100 percent accurate. He started out as my bi friend. 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 in him. He, or should I say she, is in chastity all of the time now with a device that I welded on.”
“Have you started him on hormones yet?” he asked.
“Not the real ones. But she knows it is coming. She has taken about 5 months of 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?” he 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 his training.” He said.
“Oh, well, you definitely should meet my sissy slave Jersey then. She is definitely being forced further than she ever thought he would go. I have just done it a little at a time, while 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 slave.”
“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?” Richard stated, “I would love to make her blow random men and get used as a true sissy slave. She has really gotten to be quite the accomplished cumslut.” Richard 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.
Richard was excited, he had known Dr. Cornelius was into the wilder side of life, but he had no idea that he had trained sissies before. This was turning out far better than he could have ever imagined!
He drove slowly to his house so that Dr. Cornelius could easily follow him and then pulled into his parking spot at the house and Dr. Cornelius parked next to his. He could see him pull out a bag from his car and they walked to the door of the house. he unlocked the door and went inside as Dr. Cornelius followed him up the stairs.
Once they reached the top of the stairs, they could see Jersey 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 pigtails and her permanent eyeliner was accentuated with coral pink permanent 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 tan lines 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. Jersey looked up from the computer screen to see Dr. Cornelius and Richard—and although she didn’t look surprised to see a man standing there, it was obvious that he 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.
“Jersey, I would like you to meet Dr. Cornelius. He has offered to assist me in your sissification training. Come over here and meet him.” Richard announced.
Jersey stood up from the computer desk and walked very daintily over to Dr. Cornelius. Her Mico-CB6000 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 pleased to meet you Sir,” she said in a very breathy, very sissyish voice as she extended her right hand to Dr. Cornelius with the wrist bent.
Dr. Cornelius 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.
“Jersey, why don’t you fix us some drinks? The usual for me. Dr. Cornelius, what will you have?” Richard said.
“Scotch on the rocks, please.”
“Jersey, you can make yourself an appletini. Dr. Cornelius, why don’t we get more comfortable on the couch?” Richard said.
Richard and Dr. Cornelius sat on the couch as Jersey minced over to the bar to make the drinks. Dr. Cornelius noticed the massive butt plug inserted in Jersey’s ass through the sheer panties.
“Do you always let your sissy slave watch porn when you are away?” Dr. Cornelius asked.
“Well, I won’t let her. I require it. She is required to watch at least two hours per day on the weekdays, and eight 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 he has sourced hot enough, she gets punished. I have found that it makes his 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 nine months now. She gets punished if she fails and accidentally cums.”
Jersey returned with a tray of drinks and was clearly embarrassed by the subject matter being discussed. he gave Richard and Dr. Cornelius their drinks.
“Jersey, please show Dr. Cornelius what your punishment was the last time you failed during an edging session.”
Jersey placed her appletini on the coffee table and turned around. She lifted his sheer pink nightgown and slipped his manicured fingernails into the strings on the side of her sheer pink panties. She slowly lowered them as she bent over. There was a tramp stamp on her ass, which read “Anal Slut” in six-inch red and black cursive letters that became visible to Dr. Cornelius.
“Excellent work, Richard! That is so hot. May I?” Dr. Cornelius said as he reached towards Jersey’s ass.
“Absolutely. Be my guest.” Said Richard.
Dr. Cornelius rubbed his hand across Jersey’s tramp stamp and lowered her panties even more. He was caressing each of his ass cheeks and his hand made its way to the monstrous plug in his ass. He felt the vibrations coming from the plug as he pushed it deeper into Jersey’s ass. He could hear Jersey 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 ass with. She also loves to be fisted. She loves having his hole filled because that and her sensitive nipples are currently the only forms of pleasure she is allowed. The last time we got to the nine-month point, I think she would have fucked a horse if I had let her, just to try and get off. Between the nine 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 Jersey and letting it slide out a little each time. Jersey was pushing back onto the plug, just short of bucking wildly at this point. Her groans were becoming more insistent.
“Jersey, stop being such a slut and go get Dr. Cornelius and I another drink,” Richard said.
“Please call me Drake. Your sissy slave can call me Master.” Dr. Cornelius said.
Jersey 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. Richard was always more strict and dominant when he had been drinking. The tramp stamp on Jersey’s back had been as a result of one of those evenings. And this guy he brought home seemed to be even encouraging this more—he kept mentioning hormones! Jersey was worried but also aroused. She felt a big glob of precum slide out of his Mico-CB6000. 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!” Richard yelled.
“Once you start her on hormones, she will stop trying to play with themselves so much.” Dr. Cornelius said.
Jersey heard this and trembled, but she knew she better get the drinks to them soon or risk Richard’s ire.
“Well, Drake, that is precisely my intention. I just need to obtain a supply and I will get them started as soon as possible.” Richard 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.” Richard 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.” he said.
“I need you to be 100 percent sure. This particular device lasts 5 years. Once it is in for about a week, the effects are really irreversible and the device can’t be removed after a month. 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. Jersey 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 Jersey walked over with the drinks. It seemed like her cheeks had constantly been red since this man walked into the house.
“Jersey, please help Drake take his clothes off.” Richard said.
Drake stood up, threw back the drink of scotch, and waited for Jersey to put the other drinks down. He stood there as he 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, Drake?” Richard asked.
“I love it. It is really good foreplay.” Said Drake.
“Well, Jersey 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?” Richard asked.
Drake pulled Jersey’s head towards him and shoved his tongue in Jersey’s mouth. He could tell from her body language that she did not like it. He could feel her tongue piercing against his tongue and thought that it was going to feel very good on his cock in a short amount of time.
“Jersey, 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.” Richard said.
Jersey could hear in Richard’s voice that he was getting drunker and drunker and knew that he better obey. It was hard to concentrate, because Drake was pushing the plug in and out of his as his tongue explored his mouth. his manicured hands roamed Drake’s hairy chest.
“See, Jersey. 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.” Richard said.
Jersey moved her way down, at least happy that she didn’t have to kiss Drake 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, Richard,” Drake said.
“Well, let’s do something about that. Jersey, take Drake’s pants down and start working on his cock.” Richard said.
Jersey unbuttoned Drake’s pants and then unzipped them. She pulled them down along with his boxers and she was greeted with a truly massive cock. It was only partially hard, and it was at least 8 inches long. But the truly impressive thing was its girth. It was probably about 6 inches around and had a massive mushroom-shaped head. Jersey 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, Richard?” Said Drake.
“Not at all. Jersey, let’s see how far you can get your tongue up Drake’s ass!” Richard barked.
Jersey’s stomach turned over. This was by far the thing that she was dreading the most. She made her way under Drake’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 slave and work your tongue in deeper.” Drake said.
Jersey did so as Richard watched. The further Jersey stuck her tongue up Drake’s ass, the harder his cock got. Richard was watching as his impressive cock grew to full mast. It was at least 9 inches long.
“Now, sissy, work your way back to my balls,” Drake ordered.
Jersey was tonguing his balls and his enormous cock was laying on his forehead.
“Now sissy, you get the reward. Beg me to suck my cock.” Drake said.
“Please thir, can I thuck your matthive cock?” Jersey said seductively, the giant ball in his 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.”
Jersey dove right into his work. She definitely wanted to show enthusiasm for 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 his mouth a bit for show, and then licked all around the top of the head. She slowly took the top of the head into her mouth and applied gentle suction.
“Stop teasing it and get to sucking, you fucking whore. Wrap those giant dicksucking lips around my cock slave.” He said to Jersey.
Jersey took this as his cue to get to work. She took his entire shaft down her throat. Richard 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 hang out of the bottom of her mouth and lick his balls. Jersey pulled her head almost all the way off of Master’s cock, just leaving the head in his 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 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. She 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 violent thrust.
“Slave you better be ready to take your Master’s hot cum,” he ordered.
Jersey couldn’t say anything with a massive cock violently molesting her mouth and throat. And besides, she had always been taught not to talk with her mouth full.
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 and 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 getting into her eyes.
“You better swallow all of that slave, you fucking cum dumpster,” Master said.
Jersey showed him the cum in his mouth by sticking out his pierced tongue. There was definitely an entire 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. Richard had gotten off the couch and was standing next to his. Richard scooped the copious amounts of cum off of Jersey’s face with his fingers and told her to lick them clean. Jersey greedily did so, sucking Richard’s cum covered fingers. Soon, all the cum was off of her face.
“Now, lick his cock clean, slave,” Richard said.
Jersey leaned forward and gently licked and sucked every inch of Master’s sensitive cock clean.
“Look at his little sissy clitty, Drake. It is trying its best to get hard in the cage. She must really love sucking your cock.” Richard said.
Jersey didn’t think it was her place to say that her little sissy clitty attempted to get hard when the wind blows these days. After being in chastity for nine 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 slave you have there. We will fix the sissy clitty in a few moments so that it won’t be trying to get hard ever again. Once I am done tonight, that thing will be a useless piece of flesh in less than a week. Then she will be 100 percent, sissy. I take it that you have a bondage bench somewhere in here?” Drake 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 his.” Richard said.
“Well, go get her strapped in, and I will make us more drinks,” Drake said.
Richard led Jersey into their bondage room. She saw Jersey 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.” Richard said sternly.
Jersey was clearly scared now, but also very aroused. She had always been very much turned on when Richard talked about hormones, but this just seemed so sudden. She laid back on the bench and put his legs up in the stirrups. Richard proceeded to strap her legs and feet into them and then moved up to her arms. Once her arms were secured, Richard 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 same position when Richard 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.” Richard said.
Dr. Cornelius walked into the room carrying the drinks and his bag.
“here’s your drink Richard. here’s to a long-lasting friendship.” He said as he raised his glass in a toast.
As they clinked their glasses together, Jersey felt as if her fate was sealed. She was petrified, but his sissy clitty was betraying his. It was as hard as it could get in the Mico-CB6000. Richard came over with a bolt cutter and cut the chastity off. Jersey’s sissy clitty 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 anyone in the first place.” Drake said as he fondled Jersey’s sissy clitty.
Jersey almost came off the table when he touched her extremely sensitive clitty. She wanted to cum so badly. Maybe if I behave, they will let me cum, Jersey thought.
“Do you have somewhere I can wash up before we get started? Let me just lay out what I will need here.” Drake said as he laid out a surgical pad on the table near Jersey’s feet. This was followed by several instruments placed on top.
“Sure thing. Let me show you the bathroom.” Richard said as they both left the room.
A few minutes later, they both entered the room. Drake had on surgical gloves and Richard was finishing his drink.
“Ok, Jersey. 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 slave.” Drake said.
Drake pulled out some alcohol wipes and began swabbing down Jersey’s taint at the incision point. Jersey’s legs were high in the air, and he couldn’t move a muscle. She had never felt more vulnerable. Meanwhile, Richard was busy fondling his sissy clitty—which was as hard as a rock. He began to slowly stroke Jersey’s clit up and down. It didn’t take long before Jersey was about to explode. Richard stopped all stimulation.
“Now, I am just going to give you a light local anesthesia so that you won’t feel a thing.” Drake said as Jersey felt the needle go in right below her ball sac.
Richard had resumed stroking Jersey’s sissy clit and was talking dirty to his.
“Don’t tell me you don’t love this, you fucking whore. Your little clit has never been harder.”
Jersey was almost to the point of exploding again, and again Richard stopped stroking his. Jersey could feel her balls and taint going numb.
“While we wait for the anesthesia to fully take effect, I think Jersey should provide a little oral service to me just to pass the time. Richard, could you help me take my cock out of my boxers? I don’t want to ruin our sterile environment.” Drake said as he laughed.
Richard pulled Drake’s cock out of his boxers and placed it in Jersey’s mouth. Drake began fucking her mouth in earnest as Richard resumed the torment on Jersey’s cock. Richard edged Jersey to the point of orgasm another 15 times before he heard Drake announce that he was cumming down her slut’s throat again. Richard helped Drake put his cock back into his boxers as he walked back towards Jersey’s feet. Richard could feel Jersey trembling from being so aroused and went back to work on stroking Jersey’s sissy clitty. Meanwhile, Drake had picked up a very large syringe that had a metal hormone device in it and started to sterilize it. The metal device looked bigger than a large Motrin pill. Jersey wasn’t sure where and how that was going to work.
“This will only take a few more seconds, Jersey. Once it’s in, will not be able to turn back and you will be on the way to permanent sissyhood as a slave.” Drake said.
Drake took the syringe and injected it into her taint at the base of her sac. He then slowly inserted the metal device through the syringe and into the injection point. Once the device was all the way in, it popped out and settled into her sissy sac where it vibrated in three short bursts.
“There, it’s in and activated. The hormones will start working almost immediately,” Drake exclaimed.
He cleaned the injection point again with alcohol and closed the small hole with Dermabond. He then placed a bandage over the hole. Lastly, he pulled out another syringe filled with liquid, wiped down Jersey’s sac with alcohol again, and injected the 8oz of liquid into her sac. He then declared that he was done. Richard had been edging Jersey through the entire procedure and he had managed to drive Jersey crazy for another 4 edges. Jersey was shaking in frustration.
“All done now, Jersey. The metal device inside her will release the maintenance dosages daily and will vibrate when it does. It may feel a bit odd to have another object in her sac, but it will become natural like a birth control injection. I also gave her a massive dose of a cocktail directly into her sissy sac 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. ” Drake proclaimed.
“That is excellent news, Drake!” Richard said.
“When can I use this sissy’s pussy?” Drake asked Richard.
“No time like the present. But for now, I need to cum, so his mouth is going to be occupied for a bit.” Richard said as he laughed.
Richard straddled Jersey’s face and started fucking his’ sissy’s throat. Meanwhile, Drake had retrieved the can of Crisco and was lubing his hands thoroughly. Richard immediately reached his first orgasm, and it was so strong that he squirted a huge stream of cum into Jersey’s mouth. Drake had removed the enormous plug from Jersey’s ass and was probing it with three fingers, then four. Then he had his fist inside Jersey. Richard was coming down from an extremely intense orgasm, but seeing Drake’s fist in Jersey’s sissy pussy got his going again almost immediately. he ground his cock back into Jersey’s mouth.
Richard saw Drake begin to work the fingers from his other hand into Jersey’s ass alongside his fist. He had gotten two fists into Jersey before, but it took a long time and it almost sent Jersey through the roof. Drake’s hands were almost twice the size of Richard’s and he could feel Jersey start to shake again. At this point, Drake had one fist and four fingers from his other hand inside Jersey. Richard was so turned on that he came again. Drake was trying his best to get both hands inside Jersey, and Jersey was moaning uncontrollably onto Richard’s cock. When Richard saw Drake’s other wrist buried in Jersey’s ass, he couldn’t believe it. Jersey’s sissy clitty was leaking fluid like crazy and a medium-sized puddle had formed on his stomach. Drake was working both fists in and out, and it was milking the sissy cream out of Jersey. The sight (and Jersey’s talented tongue) caused Richard to orgasm yet again. After about 10 more minutes of this, and 5 or 6 more orgasms for Richard, Drake 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 Jersey’s stomach. Jersey 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?” Drake said to Richard.
“Excellent idea.” Richard said as he got off of Jersey’s face. Richard picked up a spoon from his bondage kit and began spoon-feeding Jersey’s sissy cum into Jersey’s mouth. Jersey gobbled it up greedily and swallowed every drop. Jersey was so aroused from the whole scenario that his sissy clit never went soft the entire time.
Drake came back in the room and asked where the condoms were. Richard threw him one from his 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.” Drake said.
Richard 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, as well as any of your friends.” Richard said.
Drake put on the second condom and positioned himself at Jersey’s sissy pussy. He rammed his cock all the way in, none too gently. Jersey squealed, as he was very sensitive from the double fisting already. Drake did not hold back and fucked her with abandon. This, of course, got Richard aroused again and he climbed back onto Jersey’s face and started face fucking again. He reached down and began teasing Jersey’s sissy clitty again as Drake fucked his harder and harder. Richard had lost count of how many times he had cum already, but he managed to cum again another 2 times and edge Jersey another 10 times. Richard got off of the table and just watched Drake plow Jersey 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 slaves should always taste their Master’s seed. It is just wasted if it is shot into a condom.”Drake said.
“I agree.” Said Richard.
Drake was ramming his huge cock down Jersey’s throat again and groaned loudly as he shot his load into his mouth.
“Don’t swallow it yet, you whore. Show it to me.” He said.
Jersey opened her mouth and showed Drake the massive load that was in hermouth.
“Swish it around like you would mouthwash. That is a taste you are going to become all too familiar with.” He said.
Jersey swished the cum in her mouth for 15 seconds before Drake told her to swallow it down.
“I think we are done here, for tonight,” Drake said.
“Yes, I think you are right.” Richard replied.
Richard went to the small freezer in the bondage room and took out the item that she knew Jersey dreaded most. The ice pack. Jersey knew that if this came out, that she was not going to be allowed to cum, and was going back into the chastity device. Richard smiled an evil smile at Jersey as he placed the ice pack on his swollen sissy clitty. Drake watched and laughed as Richard held the bag and Jersey squirmed on the table as much as the bonds would allow. After 2 minutes of this treatment, Jersey’s sissy clitty had run back into his body like a frightened turtle.
“Drake, would you mind handing me that new Mico-Nub chastity out of the top drawer over there?” It was smaller than the last one.
“No problem.” He said as he handed it tom.
he slid the chastity device onto Jersey’s shriveled clit easily.
Drake leaned over Jersey and said, “Just think slut, in about a week, you will have trouble getting that little sissy clit hard. And in a month, it won’t ever get hard again. It will just be a useless piece of flesh.”
Once the lock was in place on the chastity device, Richard secured the lock. He then undid the straps holding Jersey in place and helped her up.
“Let’s get those breast forms off of his and take some before pictures of his breasts. That way, when my hormone device starts really working, we will have a basis for comparison.” Drake 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.” Richard said.
“You have a website?” Drake asked.
“Yes, it is www.SissyJersey.me I will give you a free username and password 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 Jersey doesn’t need to work anymore. There are a lot of videos on there of me fucking her with a fucking machine, 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.” Richard 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 Jersey’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 Jersey 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 stretches 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. Richard promised to email a username and password to Drake and told him to begin preparing for Jersey’s next adventure with his friends. Drake 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 Drake said that he had better be going because it was late and he had to work tomorrow.
He looked into Jersey’s eyes and said, “Bye for tonight sissy slave. 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, Richard. 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, Jersey?” Richard asked.
Jersey nodded his head in agreement.
“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?”
“Yes Master,” Jersey 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.” Richard said.
Jersey almost tripped because she was running to get the eggplant and the Crisco so quickly. The eggplant was one of the 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. Jersey returned with the eggplant and the lube.
“Get started lubing that up, and I will be right back,” Richard said.
Richard returned with a small stool and placed it on the floor. he 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.” Richard said.
Jersey 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.”
Jersey’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 he had to accomplish it tonight. She may never get this opportunity again. She was going to do his absolute very best.
Jersey removed her panties. She was already dripping out of the end of her Mico-Nub again. Richard scooped up the drippings from the tip of the chastity device and promptly put his finger in between Jersey’s thick, puffy lips. Jersey 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. Richard was standing in front of her now, his cock just inches away from Jersey’s tattooed and collagen-plumped lips.
“Don’t touch it or lick it. I just want you to smell the cock that owns your pathetic sissy self as you open yourself up for me with the eggplant. Take a deep breath and inhale me. Mmmm. Do you smell that cock? 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?”
Jersey 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 Richard.
“Yes, Master. Please turn me into an even more pathetic sissy than I am right now.”
“Do you want bigger tits?”
“Yes, Master. The biggest money can buy.”
“Do you want me to line up scores of men to fuck your mouth and sissy pussy?” Richard asked.
“Yes, Master. Please line up gang bangs of 20 and 30 real men to cover me in their cum.”
Jersey was leaking profusely out of the tip of the new Mico-Nub now. Richard collected it in the palm of his hand and made Jersey lick it up. Jersey 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. Jersey continued to bounce up and down, grunting and groaning from the monstrous invasion. Richard started slapping Jersey’s locked sissy clit.
“The anti-androgens in your booster shot must already be kicking in, you little cum dumpster. “Remember, you don’t get to cum unless you get it all the way in. Do you want some help?”
“Ughhh. Yes please, Master. It’s too big.” Jersey said.
Richard stood up behind Jersey on the stool and started pushing down on Jersey’s shoulders.
“Take it all you little cunt.” Richard said.
“Ahhhhh….no, too deep, Master.”
“Just a little more, bitch.” Richard said.
Richard pushed down more and Jersey grunted one more time. This time more loudly. She had gotten it all in as he felt her butt cheeks touch the stool. Richard walked around the stool and crouched in front of Jersey.
“Very nice, you fucking whore.” Richard said as he slapped Jersey’s locked clitty. Jersey was rocking up and down on the monster.
“This little clitty won’t even get hard anymore. Those hormones are already kicking in! I love Dr. Cornelius!” Richard said.
Jersey was getting very close to cumming.
“I’m about to cum, Master!”
“Good sissy. Let all of that nasty sissy cum out. It will be your last cum ever so you better enjoy it!”
Jersey’s clitty, although not hard, was dribbling massive amounts of cum. Richard was catching it all in his hand, in disbelief at the quantity since Jersey had already been milked earlier tonight. Jersey was shaking uncontrollably from the intensity of the orgasm and pulled up off of the monster in her sissy pussy.
“here you go, cum dump. You know you have to lick it all up now.” Richard said, holding his hand up to Jersey’s mouth, his palm was filled with the milky white sissy cream.
Jersey 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. I don’t even think we will need the icepack, it’d not even filling the cage you limp dicked little sissy. We will probably have to buy an even smaller chastity device now.” Richard said as he laughed at her and turned off the video recorder.
They cleaned up and got ready for bed. Jersey lay in bed wondering what the future might hold for her—she was worried, but oddly very aroused as she fell asleep
Jersey awoke the next morning with her babydoll nighty completely soaked in sweat. She thought this odd because Richard 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.
Richard entered the room carrying a glass of Gatorade and something else in his other closed hand.
“How are you feeling, sissy slave?” Richard asked.
“Not too good Master.” My whole body aches, and I am so hot.”
“Well, the good doctor said this might happen. That just means the sissy enforcement juice is really kicking in now!” Richard said. “here, take these two Midol. They should help with the cramping.” Richard said as he held out two pills.
Jersey took the pills and was surprised that Richard was reaching to unlock her Mico-Nub.
“And this will help with nausea,” Richard said as he unlocked the device and took it off. he then fastened cuffs to Jersey’s wrists and ankles and connected them to the D rings on the bed frame. Jersey was spread-eagled, with her legs up in the air similar to her position in the stirrups last night. Richard lubed his fingers and Jersey’s sissy pussy and then started probing. He inserted what looked like a large pill into Jersey’s open sissy pussy.
“This is a Phenergan suppository and should help with nausea.” Richard said as he began to massage Jersey’s sissy clit with one hand and massage Jersey’s prostate with the other.
Jersey moaned as Richard stroked his flaccid sissy clitty. It felt so good, as it normally did when Richard stroked her, but her sissy clit refused to harden no matter how much Richard stroked it. Richard continued to roll the soft piece of flesh between his fingers as he 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 even faster. You will be a full-fledged sissy slave girl before you know it. Do you want to be my sissy slave girl?” Richard asked as he continued to stroke Jersey’s flaccid member and massage his prostate with his fist.
“Yes, Master.”
“Yes, what?” Richard demanded.
“I want to be your sissy slave girl.”
“Say it louder then,” Richard demanded.
“I want to be your sissy slave girl.” Jersey said a little louder.
“Louder.”
“I WANT TO BE YOUR SISSY SLAVE GIRL!” Jersey almost shouted.
Richard proceeded to bring Jersey 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. Jersey was a sobbing wreck at this point and leaking precum onto her stomach.
“How are the cramps now, better?” Richard asked, spooning the sissy cream into Jersey’s mouth.
“Yes, Master. Much better.”
“Good. Now, which cock do you want me to use on the fucking machine to fuck you? Do you want Jenna?” Richard 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. Richard knew that Jersey 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 dildoes that had been inside her.
“Please fuck me with the giant black one, Master,” Jersey said, referring to a rather large specimen that was 9 inches in circumference and 11 inches long.
Richard stood up and started hooking up the black monster onto the fucking machine. He always loved fucking Jersey with a fucking machine. He loved making the little bitch submit to huge cocks inside her—it turned Richard on so much.
“Are you ready, you little cum dumpster?” Richard asked as he positioned the tip of the black monster right at the entrance to Jersey’s sissy pussy.
“Yes, Master. Please fuck me as hard as you possibly can.” Jersey said.
“Your wish is my command, whore.” Richard said as he rammed the 11 inches of thick black cock balls deep into Jersey’s eager fuck hole. After three strokes of going all the way into Jersey’s pussy and all the way back out. “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 pussy for days. You want that don’t you, you little bitch?”
“Maybe Dr. Cornelius can bring some of his friends over later so that you can have one cock in your mouth, another in your sissy pussy, and another covering your enlarged tits with cum.” Richard said as he started tweaking Jersey’s pierced nipples with his fingers in between thrusts.
It was all too much for Jersey. She was extremely aroused from the edging, verbal humiliation, nipple stimulation, and pounding. She could feel the sissy orgasm building inside of her, but her sissy clit remained limp as can be, almost hard to tell that it used to be a cock. Richard continued to pound away, even harder than before with the machine.
“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 with cum.” Richard said, turning the machine up and thrusting harder and harder.
Jersey 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 his 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 clitty. Richard continued to engage the machine, but a bit slower now than before, but still pushing the monster all the way in and pulling it all the way back out. He wanted to make sure that Jersey remembered this sissy orgasm for a very long time.
“There you go, sissy. Let all that nasty sissy cream out. It just makes you more girly.” Richard said as he started scooping the cum off of Jersey’s stomach and putting it into Jersey’s panting mouth. “That’s the only way you will ever get relief again, slave. I sure hope you enjoyed it.” Richard said as he pulled out of Jersey’s sissy pussy with the monster. Richard then reapplied the Mico-Nub to Jersey’s shriveled clitty and locked it.
“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?”
Jersey nodded and she did as Richard positioned himself with his knees on either side of Jersey’s face. Jersey could see that Richard was already soaked with precum. Richard lowered himself onto Jersey’s face.
“Now suck, you worthless cum dump. I need to keep you around here for something since that little pathetic piece of flesh no longer works.”
Jersey began sucking on Richard’s hard cock. Richard was thrusting away at Jersey’s face and in no time he was approaching orgasm. It turned him on so much to sissify this little bitch, he thought as he came in a violent orgasm. He raised off of Jersey’s face for a second, to recover his senses. Then he lowered back down into Jersey’s throat.
“You better not miss one drop, understood?”
Richard began to release his morning urine into Jersey’s waiting mouth. Slowly at first, and then building into a much stronger stream. He could hear Jersey gulping to try to keep up, and it pleased him greatly. He had a really full bladder and knew that Jersey’s stomach would be very full when he was done. Richard continued to piss a hot stream of urine into Jersey’s mouth, not slowing up. He somewhat hoped that Jersey would miss a drop so he could have an excuse to spank her for a few hours. As he finished up, he was again aroused.
“Lick it clean, bitch.”
“Now you have me turned on again. Keep licking. I want to cum again.” Richard said.
Jersey’s tongue and jaw were getting tired, but she knew better than to stop. She continued to suck, moving her tongue rapidly. Richard was thrusting into Jersey’s throat now, almost painfully deep into Jersey’s throat.
“Oh, God. Yes, take it, you little sissy slave. Make me cum again!”
Richard 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 four-quart enema bag this morning.”
Richard unlocked Jersey. Jersey got up and ran to the bathroom to get herself cleaned up.
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