Sindys Undoing

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."