Cuckolding Sindy Ch. 02

Sindy listened intently over the intercom as Lucy was in the other room with her dates. The moans and groans were constant as her Mistress orgasmed repeatedly. It always turned Sindy on immensely to hear her Mistress with other lovers. She sat in front of the computer with her largest vibrating plug inserted in her ass and watched the sissy on the computer monitor serving 5 really well hung men simultaneously. Mistress always chose what porn Sindy was forced to watch, and it was always designed to make Sindy's chastity torment worse. This particular video was performing as designed, as Sindy was very, very, aroused.

Mistress had allowed Sindy to cum two weeks ago on date night, and cumming was all that had been on Sindy's mind the entire time. Prior to that, she hadn't cum in over 7 months—she had gotten to the point in her chastity sentence where she had successfully been able to not think about cumming anymore, or only thought of it very rarely. However, with the recent cum, it was all she could think about and it consumed her every waking thought. She had previously thought her Mistress was devious, now she knew it even more than ever. She thought her Mistress had been allowing her to cum out of generosity, but now she knew that it had been done to reinvigorate the torment of chastity. Her porn watching requirement had been increased to 2 hours per day instead of the one hour requirement before. She had been edged to the point of cumming for two hours per night without allowing release. It had only been a two weeks and Sindy thought she was going to lose her mind with a desire to cum.

Her mistress had told her that Sindy was not going to cum again until she had 100 men for her date nights. The men could be the same men, or different men—but the rule was that they had to have at least 8 inch cocks or bigger. The other rule was that Sindy had to line the dates up. Sindy had been frantically searching the internet trying to line up dates for her Mistress because she had done the math. She knew that even with two guys per week that it would be a year before she could cum again. Last week she had arranged three men for her Mistress, and Mistress was currently enjoying herself with a different three men as evidenced by the sounds coming through the intercom. Sindy was always required to perform clean up duty after her Mistress' dates, and sometimes was required to serve the men if they were interested. These three guys had not been, so her Mistress had chosen the required porn, inserted her plug and turned on the intercom so that Sindy could listen. The porn, the edging, and listening to her Mistress getting pummeled had Sindy so aroused that she could not think straight. She was leaking precum onto the towel she was sitting on.

It was then that she made a very poor decision. She was so aroused and consumed with the thought of cumming that she looked over at the Hytachi magic wand that her Mistress used frequently to cum. She listened very intently to the sounds coming from the intercom. It didn't sound like they were anywhere close to finishing and she grabbed the Hytachi, turned it on high, and placed it against her CB3000. The feeling was heavenly. Sindy immediately started feeling the effects of the intense vibration. Precum started flowing out in more copious amounts as the minutes wore on. She heard orgasm after orgasm coming from the intercom, so she knew there was no danger of Mistress walking in on her. However, what she did not know was that Mistress had rigged a camera in her room and was watching Sindy's every move as Mistress was being pummeled. In between being pounded by her dates, Mistress would glance over at the camera periodically.

"That little bitch." Mistress thought. She made a mental note to deal with this as soon as her festivities were done.

Sindy was in rapture with the vibrations being channeled through her CB3000, but even she knew better than to cum. With a force of willpower even she didn't know she had, she stopped the Hytachi. She looked at the puddle of precum on the towel and realized that she would be in huge trouble if Mistress ever found out that she had even attempted this. She quickly cleaned everything up and put it away and went back to watching her sissy gangbang porn on the computer monitor. She tried to put the thought of cumming out of her mind, but it was very difficult based upon her level of arousal.

Sindy heard the ending of the "date night" in the other room and tried desperately to focus on her video. She knew Mistress might quiz her on the video's content later, so she refocused her efforts on the video. She heard the door close as Mistress' dates left and shortly thereafter, Mistress entered the room.

"Hello Sindy. I want to thank you for introducing me to those three gentlemen. They performed as advertised. Now I need you to perform your duties."

Sindy had plenty of practice in this, and knew exactly what was expected of her. She went to her place on the bench and lay on her back. Mistress came over and climbed on the bench and straddled her face.

"I want you to start with my cunt tonight. It is more sore than normal. Tyrone's cock was the biggest one I think I have ever encountered, and Maurice and Demarcus were no slouches either. I need your velvet tongue to clean me out."

Sindy could see the reddened lips of a well fucked pussy presented above her face and she went to work frantically on Mistress' cunt, lapping and sucking as if her life depended on it.

"I must compliment you on your selections. These guys were the real deal. They didn't even need Viagra, and they could keep going and going. I am glad for your sake that you asked them to abstain from cumming for a week prior to our meeting. There is plenty of cum for you to lap up now and I know how much you love it, you little cumslut."

Sindy continued lapping as her Mistress talked. Normally at this stage her Mistress' juices were all over her face, as well as globs of cum that dripped out of her. Sindy was confused because all she could taste was her Mistress' juices, lube, and a slight taste of latex.

"I know you are confused. But these guys wore condoms. Don't worry. I have saved all of their delicious cum for you."

Sindy continued licking until Mistress had several more orgasms.

"Now let's move to my ass." Mistress said as she adjusted herself accordingly.

Sindy dove into Mistress' ass with her tongue. She continued licking and could tell that Mistress had been fucked repeatedly there as her asshole was quite distended.

"Gently, cumslut. I am a little tender there. These were real men with real cocks, not like the little sissy clit that you have. Tyrone really gave it to me good. Are you aroused right now? I bet you would like to fuck me, wouldn't you? That's too bad, baby. We tried that, remember? I couldn't even feel your little sissy clit inside me. No, all you are good for now is being a fuckhole cumslut and for your well trained tongue. Besides, you know the requirements before you are released from your cage again. It wouldn't be fair to allow you an orgasm prior to you fulfilling those obligations, would it?" Mistress taunted as she came to yet another orgasm.

Mistress climbed down from the bench.

"Before we get started, I have to give you your reward for being such a good cunt lapper. I know that you have been craving your normal dosage of cum and you didn't get it out of my cunt or ass." Mistress said as she retrieved the used condoms from earlier. Mistress had 9 of them hanging from her hand, and each of them had the reservoir tips of the condoms completely full of cum. Mistress then took them one by one and squeezed the cum into Sindy's waiting mouth. Sindy knew she couldn't swallow until she was given permission, so she lay there as Mistress filled her mouth with load after load of cum. When Mistress had squeezed the last one into her mouth, Sindy's mouth was very, very full of thick globs of semen.

"There. Now close your mouth, but don't swallow yet. I want you to swish it around and savor the flavor. Then I want you to gargle with it."

Sindy followed Mistresses instructions to the letter. Swishing and gargling. The taste permeated her whole mouth. The smell was so strong. Her Mistress had conditioned her to be aroused by the flavor, and she could feel herself leak out just a little more precum from the CB3000.

"ok, you can swallow now." Mistress said.

"Let's get you in position for your nightly edging session, shall we? I have a new toy that I want to try out as well."

Sindy flipped over on the bench and got on all fours, with her knees on the shelf and her chest flat against the bench. Her B cup breasts rubbed against it and gave her even more tingles that added to her level of arousal. Mistress started attaching the straps, locking Sindy in place. First over each ankle, then each wrist, then a strap across Sindy's back. Sindy was completely immobilized and couldn't move off the bench even if she wanted to.

"We can't have you moving around. I know sometimes you like to buck your hips to try and orgasm. And we can't have that can we? You know that any attempt whatsoever to try and cum prior to completing your obligations is punished most harshly, correct?" Mistress asked.

"Yes, Mistress I do."

"Good. I am glad we are on the same page as far as that is concerned." Mistress said.

Mistress removed the CB3000 from Sindy's hormone shriveled clit. Precum had filled the end and was leaving a long strand dangling as Mistress pulled it away.

"My, someone has been excited. It must have been all the sounds coming from my room, right? Or maybe it was that sissy gangbang porn you were watching? Or maybe the giant vibrating plug in your sissy pussy?" Mistress asked.

"Yes, ma'am it is all of those things." Sindy replied.

Mistress started the manipulation of Sindy's tiny penis. She stroked her repeatedly, bringing her to the point of orgasm over and over and over again. Sindy was panting from arousal after about the tenth time and by the twentieth time she was going out of her mind. Mistress continued this for about an hour and at least thirty edges. Sindy was completely helpless, completely aroused, and totally drained when Mistress stopped the edging. A steady stream of precum was drooling from Sindy's shriveled penis, and her balls had swollen and developed that familiar ache.

"There, now that we have that out of the way, I want to try my new toy. This is a special toy, so I want it to be a surprise." Mistress said as she fastened a blindfold over Sindy's eyes.

Sindy could hear Mistress moving around the room, moving objects around. This was unusual. Mistress normally didn't blindfold her for new toys. She felt Mistress approach her and start attaching something around the back of her head.

"This is a new penis gag that I bought especially for you. Open up."

Sindy opened her mouth and felt a spongy latex gag being inserted. It didn't seem too daunting, maybe about a half inch in diameter and about 2 inches in length. That was fine with her because she didn't know how long it would be left there and some of the other gags Mistress had were far more severe. She was pleased that this one was much smaller until her Mistress started talking.

"The purpose for the gag is that deceptive little sissy faggots should not be heard during punishment sessions. This is a new inflatable gag." Mistress said as she started pumping the bulb to inflate the gag. Sindy could feel the penis gag start to expand with each pump and soon her mouth was entirely full with the penis gag. It was pushing against the back of her throat and Sindy started to whimper. Mistress gave the bulb one more pump for good measure and Sindy groaned. She was starting to panic as the penis gag had gone into her throat, and her mouth was completely full with latex.

"Now that we have you all situated, I want you to know that I know you tried to use the Hytachi to cum while I was in with my guests. I am not going to tell you how I know, but I do know. Haven't I clearly defined the rules? It is strictly forbidden to even attempt to cum!" Mistress said this as she crashed a blow across Sindy's upturned ass with a neoprene cane. Sindy's whole body screamed as she felt a white hot line across her ass that seemed to emanate pain throughout her whole body.

"Now at first I thought I would just cane your ass until it was shredded to pieces so you would learn your lesson. However, that damages the aesthetic appeal of your ass so I can't charge customers as much to use it. And I also have a new toy that I have been wanting to try out and this is the perfect opportunity."

Sindy breathed a sigh of relief. She hated being caned more than anything, and her ass was already on fire from the one stroke she took. She wasn't worried about Mistress' toys as she felt she could take nearly any size toy in her ass, including the monstrous vibrating one currently inside her. She began to relax a little, as much as one could while being plugged from both ends and with the sting of a cane stripe across her ass.

Mistress then removed her blindfold.

"I want to see your eyes as I tell you what I am going to do." Mistress said.

Mistress held up a device in front of Sindy's eyes. It looked like a pair of pliers, but had three different metal prongs instead of two.

"Do you know what this is you little cumslut faggot?" Mistress taunted.

Sindy shook her head from side to side indicating no.

"This is called an elastrator. It is used by veterinarians across the globe to castrate animals." Mistress said as she picked up a small, thick looking green rubber band and placed it over the three prongs on the device. The band looked like a very small rubber washer.

"I'm told that when put on, the balls will be completely dead in one hour. I am also told that it is extremely painful without anesthesia. "

Sindy looked up at Mistress, shaking her head no repeatedly. She was trying to plead with her Mistress with her eyes, imploring her not to do it. She was also trying unsuccessfully to scream through the gag.

"Good thing we have that gag in place. We wouldn't want to disturb the neighbors. The desperation in your eyes makes me so wet, just so you know. The way this works is to squeeze the clamp like so.."

Mistress squeezed the handle, and Sindy could see the three prongs open up and the small green rubber band open and stretch with the prongs. Then Mistress walked around behind her and out of her line of sight. Sindy started squirming on the bench as much as she could, but was immobilized so much that she could barely move. She felt Mistress start manipulating her balls inside the stretched out band. She felt one ball being placed inside the ring, and then the other.

"Just so you know, this is all your own doing. You knew the rules, and you knowingly violated them. I had no intention of using this before, I just bought it on a whim. But once we get rid of these ugly balls, your panties will fit better and we won't have to worry about you trying to cum again without permission, right? I think this is a win-win all the way around."

Sindy was still squirming frantically, trying to scream through the gag, and trying to make eye contact with Mistress one more time before she made this irreversible decision. It was no luck, as Mistress did not come back into her line of sight. Sindy was hoping that Mistress was kidding about this. It meant that she would never ever get the chance to cum again. She knew that the massive doses of hormones would eventually castrate her, but this just seemed so sudden and painful way to do it.

"Ok, sissy. Here we go. Just remember that you are the one who chose to break the rules and you knew the punishment would be very harsh."

Mistress slid the band off of the prongs right above Sindy's balls. Sindy immediately felt the most blinding pain she had ever felt as her spermatic cords were crushed together amazingly tight under the tightly constricted band. This was 50 times the pain of the worst caning she had ever had. Her balls immediately turned a bright purple color, and even Mistress was astounded at the effect. Sindy was thrashing as wildly as she could in her confines.

"If you think that hurts, wait until I do this." Mistress said calmly.

Mistress swabbed Sindy's excruciatingly painful balls with an alcohol wipe. Sindy groaned even more into the gag as her extremely tender balls were handled. Then Mistress injected the needle right below the band and above the balls and started the saline drip. Sindy could not see what Mistress was doing and instead was trying to breathe deeply through the pain but felt the needle prick even through the pain. Mistress squeezed the saline bag gently to make sure that the flow had started into Sindy's balls and checked her watch. She made a mental note of the time, and watched Sindy's constricted ball sac start to expand ever so slowly. Mistress then walked around to the front of Sindy and looked at her desperately pleading eyes.

"We both know this will be better in the future. Your panties will fit better with no unsightly bulges, and your temptation to try and cum will stop. Yes, this is for your own good." Mistress said.

Sindy could barely focus as the pain was so great. And it seemed to be getting worse by the second. Tears were streaming down her face.

"Now, we will just leave that on for an hour, and then it will all be done! Doing this to you and watching your reaction has gotten me so turned on that I need to take care of it. Besides, we have an hour to kill. And your balls." Mistress said as she laughed and grabbed the Hytachi off the shelf and sat in a chair right in front of Sindy's line of sight. The irony was not lost on either of them that Mistress was using the Hytachi, the very thing that had gotten Sindy into trouble in the first place. Mistress placed the very high powered vibrator on her clit and almost immediately came.

"Holy shit it feels so good to cum. If you had just done what you were supposed to, you could have probably enjoyed an orgasm in a year or so. But no, you had to be a naughty little cumdumpster." Mistress said as she rode the Hytachi to her second orgasm within minutes. Mistress was carefully eyeing her watch as she came. She had no intention of leaving the band on for an hour, but she wanted Sindy to think she was. Sindy was about to pass out from the pain, and it felt like her balls had grown to three times their normal size. She could not believe that Mistress was enjoying herself so much as she was being castrated. Mistress had four more orgasms from the Hytachi, and looked at her watch. Fourteen minutes had elapsed. She had wanted the band to stay on for 15 minutes, so the timing was perfect. Mistress took her finger and wiped Sindy's tears and then tasted them. She put the Hytachi away, and walked behind Sindy.

"Your tears taste so delicious to me. My, how beautiful your balls look. They are such a bright purple. And so big, too!" Mistress said as she snapped several pictures of her handiwork. Sindy's balls had taken 1000 milliliters of saline in addition to the swelling from the band and were quite huge. Mistress could not believe it and immediately got wet again. She removed the needle from Sindy's balls and noted that the entire saline bag was empty.

"Now, do you think you have learned your lesson, or do you think I should leave this band on for another 45 minutes or so?" Mistress asked.

Sindy was deep into subspace, but immediately came out of it as she heard the question. She vigorously nodded her head up and down and was grunting as loud as she could so that Mistress would know that she wanted this infernal band off of her balls.

"Ok. We will take it off then. But I do hope that you learned your lesson this time and we don't have to repeat this exercise. Because next time I will leave it on for thirty minutes, or maybe even an hour. Now hold still. I don't want to accidentally cut your balls off trying to cut off this band." Mistress said as she grasped the fingernail clippers and began to carefully remove the band. Sindy became deathly still as she could still not see what Mistress was doing and imagined in her head Mistress standing behind her with a scalpel.