The cane came down hard across the back of Cindy’s thighs, giving a fresh burst of pain. At first the pain was unbearable and she just wanted everything to just stop. But that didn’t last long. As soon as she felt that incredible pain, it was just as soon that it was not enough. Another whoosh as the cane came down, hitting slightly higher on her thigh. A squeal escaped past the ball gag. The obvious juices running down her leg added to her humiliation and excitement. The next one was slightly higher again. Cindy gasped as the cane hit again. The man with the cane must have realised Cindy could take more. Whether it was because of the sound of her panting or he noticed the pussy juices leaking out like a torrent, but the next stroke came down harder than the others. Her body leaped like an electricity bolt tore through her body. Tears ran down her face and she moaned. To anyone who listened carefully, or even cared, would hear her moans were more of relief than pain. This was what she had been searching for.
The cane resumed up Cindy’s thighs with a more even and less severe stroke. Cindy seemed to relax and let out low gasps after each stroke. She was losing her fear and started to take some weird pleasure in the situation. She thought to herself “I could take anything he could do, maybe even a little more”. Without thinking she arched her back down. She had always been self-conscious of her big puffy labia, but maybe God had given her them as a gift for such a situation. By arching her back down, her lips were as far out between my thighs as possible and exposed. Cindy’s body had betrayed her and her captor new it. The cane stoped.
The male captor exclaimed, “I have never seen such a thing. Look penny, she is not covering her pussy at all. It is like she wants the cane over her pussy. “
The husky voice of the female captor replied, “Well, I don’t think you would be a good host at all if you didn’t give her what she wants.”
“Hey girl, if you thought putting your pussy out like that would make me think twice about caning you, you better think again. Do you know I am going to cane you there?
“Are you going to keep it out for me?
She nodded again.
The captors gave a short disbelieving laugh.
Without warning there was a short whoosh and a crack as the cane came down square across her pussy and thick labia. Cindy saw stars. She was already so turned on there was almost no pain at all. Her pussy spasmed into massive contractions and felt like a million angry ants exploded from her pussy. For an instant the world was vivid, bright and sparkly.
“Did you see that? She squirted all over the table,” giggled the male.
“Look Tom, her pussy is still twitching. I think it is safe to take the ball gag off.”
“Wait. Let me. Girl, look at me.” As Cindy started to gain her breath back she looked up at the woman. There was comprehension in her eyes as she had seen her so many times from a distance. Up close though she was more sexy and more intimidating than expected.
The lady smiled, “You were very naughty to be sneaking around here. But you have taken your punishment well like a good girl. We think we could come to some kind of arrangement. But first I want to know… will you scream if I take out the gag?”
Cindy shook her head.
The female captor turned to Tom, “I think I believe her.” She turned to Cindy again and said “if you do scream, I will gag you again and use a cattle prod on your clit until you pass out. Would you like it if I did that? Huh?”
Cindy just looked at her captor. She wanted to say no. But the use of a cattle prod on her pussy was something that had never occurred to her. She became so absorbed in thinking about whether it would be too much that she forgot to answer. Instead she was truly considering it. Her clit had always been very sensitive. It never took her too long to cum as long as she had a really dirty thought to think about. Right now she was more turned on than she had ever been in her life. What would repeated shocks from a cattle prod do? All of these thoughts crossed Cindy’s mind. The hesitation obviously confused her captors.
The female bent down so that her face was an inch away from Cindy’s, “I said we would torture your clit until you pass out if you scream for help. You don’t want that do you?”
Cindy looked at her in the eye so she knew I wasn’t ignoring her and did her best to shrug in her confinement.
“What do you mean?” frustration was clear in the lady’s voice.
Tom laughed and said “would you like us to use the cattle prod on you?” Cindy gave an unsure nod.
But if we don’t want you to, will you scream for help?” At that Cindy gave a quick shake of her head for no.
He laughed again, “Just as I thought. You have to ask the right questions Penny. We are dealing with a rare find here. You threatened her with the wrong punishment. Look she already said she wouldn’t scream, but let me try something out.“ The man move Penny out of the way and stood in front of Cindy.
Grinning he said, “If you scream for help, you will never be allowed to come back again. You wouldn’t want that now would you?” If Cindy could smile while she had a ball gag in her mouth she would have. She gave her head as dramatic a shake as she could which produced the expected giggles.
He reached over and released the ball gag. Drool spilled down over Cindy’s chin. She played the part of a submissive and stayed silent. However, on the inside, Cindy was screaming for sexual attention, not this getting to know you crap.
Tom continued, “Good, you’re obedient. I want to know what you were doing down here and how you got in.”
In the firmest tone she could manage she said “I am not saying anything to you until you make me cum and cum hard. I don’t care how you do it, but if you think I am going to do small talk while I am naked, strapped down on a table by known rapists you have misread my priorities.”
“Be careful of what you ask for. We are going to do unimaginable things to you. You are going to wish you were never sexually curious.” It was clear he felt he needed to establish dominance and had resorted to bragging. It was a little disappointing.
“Right now you are making me sexually furious. I am losing my buzz, and if you don’t do something soon I am only going to wish I found someone a bit more hardcore.” She smirked as she baited him. If there was one thing Cindy hated, it was people who talk when they should just do, particularly at this moment. She had lied though. She wasn’t losing any arousal. Begging for sex while strapped on a table in front of scary strangers was more than she had ever fantasied about before. Yet she wanted more.
The first thing that Cindy felt was two cold metallic objects that pressed against either side of her pussy.
“Let’s see exactly how you would have handled the cattle prod” Cindy pushed back against it, daring him.
Snap! She launched forward with the bindings the only thing keeping her there.
“Oh God” Cindy moaned and then started to sob. The others stayed silent.
Penny asked, “hmmn, was that too much dear?”
Cindy looked up with the tears in her eyes, “well, my mother always said that you can’t judge anything by the first time. You have to be open to experiences and give them another go.” With that she gave a reassuring smile and wiggled her bum.
Tom smiled and said, “Maybe later. You came here to get fucked, I think that is what you deserve.”
“Yessss!” called Cindy, and then was immediately embarrassed by her own enthusiasm.
Penny laughed at her and turned tom, “hold your horses big boy. Remember what your friend said about her. She may be a fire cracker waiting to go off, but she may also be a virgin. I know what you are thinking, but we have to check. If she doesn’t have a hymen, then you can fuck her however you want. But if she does, we may need to think about it a bit.”
Cindy was not pleased by this at all. “Oh come on. You cannot be serious. Just fuck me! You can’t tease me like this and think I won’t kick your ass later.”
Tom moved behind Cindy and remarked, “There is no way a freak like this hasn’t busted her hymen at her age. Hell, I bet her bedroom doorknob is slicker than a KFC grease bit.” With that he gently pushed apart Cindy’s labia and started to open up her pussy. Cindy started to rock slowly back and forth. His fingers slowly went in until he felt the hidden little membrane. The man gasped, “Holly crap, it wasn’t a lie. I have never taken a cherry before. All my girlfriends were total sluts before I met them. But I don’t see how this changes the plan?”
Penny stood up straight with her hands on her hips, “It changes things because I say it does. I want it to be the kinkiest cherry busting in the history of mankind. You are just going to have to fuck her ass and play with her clit. Otherwise I am sure she will break the table in half to get to you.” But Cindy was not even listening. There were fingers still in her pussy, and it was more than she had dared have in there before. It was not going to be long for her just with the light movement in her pussy. Then she felt his hot breath on her pussy. She started to rock a faster and pushed back as far as her binds would allow. Tom was very careful not to let her brake her cherry on his fingers. He knew it would be his, and sometimes the wait makes it even better. While Cindy was fucking herself on his fingers and rubbing herself over his face he tried to access her clit with his tongue. As soon as he did he was rewarded with a finger massage. Cindy screamed out her orgasm like she was having a lust demon exercised from her body. Every muscle in her body was tort and sweat ran down her whole body. Yet it was her pussy that was working the hardest as the little muscles in her pussy danced along the man’s fingers, milking and squeezing them for a reward they could not provide. As Cindy was about to be buffeted by waves of pleasure, every sense of her being started to focus on her love button. Her body froze and tighten with the intensity of the orgasm, it was then that Tom chose to put his mouth around Cindy’s clit and suck hard. It was like he was trying to give her a hickey on her most sensitive part at the most sensitive time. To Cindy it felt like he was sucking her soul out through her pussy. Cindy could do nothing about it, but ride the wave of the most intense orgasm she had ever had. Tom kept sucking hard while Cindy screamed and convulsed in her bonds until she went limp and fell forward in a heap.
Penny let out a hoot, and gave a standing applause, “Well done. Well done indeed. I think she will be putty in your hands, if her brain hasn’t melted or snapped. I hope your friend gets here soon. I think now would be the perfect time to seal the deal. “
“I heard a car pull up before. That is when I decided to let her cum. I am sure she will be here any minute now. In fact, I think I can hear her upstairs” replied Tom looking up.
Cindy was starting to get her bearings again, but she was content and didn’t really care what was going on. She felt a warm glow envelop her as she drifted off to sleep. So when Tiffany, Toms “friend”, entered the room she saw Cindy strapped face down with her ass high in the air starting to snore.
Tiffany looked confused and then angry, “What is going on? Why is she asleep? Why aren’t you fucking her? ”
Penny put her hands out to calm her, “no no no, it’s not like that, she has just cum really hard. But I do agree, we can’t have her sleeping when we have so many important things to discuss. Tom, I think a gentle butt fucking should wake her up. I want to see how much you can fit in before she wakes up.”
Tom’s wet glistening face lit up with a wicked grin. “Can I loosen her up first or should I see how I go with just my cock?” Tom knew the rules of a challenge where always important. You need to know the boundaries before you can test them.
Penny paused in contemplation and then replied “I will let you decide, but for every inch you get in before she says a word about it, you get to pick a game to play with her.”
That gave Tom an idea. You see Tom liked to think of himself as an amateur proctologist and gynaecologist. With Cindy in her current position and relaxed state, her ass should be opening up. Furthermore, challenge was to get as much in before she said anything about it. If he could just get past the sphincter he could almost ram it in before she even knew what was happening. With plenty of lube it shouldn’t be too much of a pain in the ass for her. With that in mind he didn’t hesitate. He climbed up on the bench behind her and motioned to Penny for the lube. Penny kindly applied it for him, rubbing it up and down his ten and a half inch cock. He had always been proud of the length of his cock but until this moment had wished it was thicker.
Cindy was falling deeper into a sleep. With his fingers, Tom used some of the lubricant on his penis to lubricate the entrance to her anus. Cindy did not react, which suited Tom just fine. He lowered himself and placed his cock against the entrance. He applied only a little pressure with his cock and kept it there. Just as he hoped, he felt the sphincter start open up easily. Feeling encouraged he pushed a little more. Cindy’s snoring became quieter but her breathing started to get quicker. Tom pushed a bit harder and was rewarded by her anus opening up enough to get the head right in. He started to move his cock back and forth, trying to massage the sphincter to further loosen it. Tom became so focused on his mission that he wasn’t aware that Cindy was starting to stir. Tom started going deeper with his thrusts, preparing for the big one that would go balls deep. Then without warning Cindy pushed back hard taking all of his cock in one go.
“Oh God you have a big dick” cooed Cindy, “now fuck my ass you sick fuck!” Not being one to beat around the bush Tom took it for the challenge it was. He pulled back almost taking his dick completely out and then lunged forward. Cindy let out a “whooff” sound as the impact of Tom’s cock almost winded her. Then Tom pulled back and repeated this, fucking her ass hard but with a steady rhythm. Cindy hadn’t completely lost her high from her last orgasm and a new one built quickly. However, Tom rarely got to butt fuck a pretty girls as hard as he wanted, so without warning he shot a load deep inside Cindy’s colon. However Cindy wasn’t finished, she started fucking herself on Tom’s still hard pole. Tom’s penis started to get too sensitive, so he started to back out. Lucky for Cindy, Penny wouldn’t have that.
“Be a gentleman Tom, Let her finish.” Tom, deep down didn’t like to disappoint. So even while the butt fucking turned to agony for him, he continued to fuck Cindy’s eager ass.
Finally Cindy pushed back onto Tom’s cock and let out a deep moan. After having cum this time she just stayed still with the cock lodged as deep as it could go.
Having not yet been noticed by Cindy, Tiffany decided to make her presence known. “Well I guess that confirms it Cindy. You are a true nymphomaniac.”
Cindy’s attention sprang towards Tiffany in utter confusion and her mind reeled. Why was her best friend here? Why wasn’t she afraid of these people who had her bound to a bench? Why would Tiffany, the most prim and proper person she knew set her up to get butt fucked? None of this was making sense at all. She wanted to ask all of these questions, but only managed “huh?”
Tiffany stood right in front of Cindy with her hands on her hips and said, “You heard me. You are a complete slut. We are here for you intervention.”
None of this was really making sense, but she knew when Tiffany was getting on her high horse. Cindy spoke slowly as she tried to collect her thoughts, “So let me get this straight Tiffany. You dared me to come down to your neighbours basement so that they would fuck me and you could tell me off for it?”
“You have said it yourself. All day you think about sex. You have never had a boyfriend because you were worried that as soon as you had sex you wouldn’t stop. You have told me some of your fantasies. They are damn well crazy, you will either end up diseased, mutilated or killed. I can’t let that happen.” To Cindy’s surprise Tiffany said all this with a straight face. It wasn’t that it was lies, rather that it was a ridiculous reason to have her bound and butt raped.
Tiffany continued, “I have come up with an alternative for you. I can’t stop you being the depraved cum bucket that you are destined to become, but I can help you be safe and disease free.”
Tom’s legs started to cramp so he pulled his large cock out of Cindy’s ass. It was like her butt was suddenly lonely. She knew Tiffany did want what was best for her. Tiffany was the smart practical one who had gotten Cindy out of many problems in the past. So she sighed and said, “Okay, so what is your plan?”
Tiffany brightened up with pride, “well you have witnessed the very first part of my plan. As you know, these are my neighbours, and as I said, they are a couple of perverts. What I haven’t told you is that they are also porn stars. They have a website dedicated to any kind of kink that you can think of. So remember in high school how you said you would like to be put on a table in the science labs and have each person in the school do whatever they wanted to you? Well you can’t do that, but you could something similar, with pornstars who have large cocks and are regularly tested for VD. Or how about that time how you fantasized about letting a homeless man give you a clit piercing? Well instead, we could have a trained tattooist pretend to be a bum and pierce your clit on video. It is much safer.”
Things were starting to make a bit more sense now, but it wasn’t all clear yet. “So then why didn’t you just ask me if I would do kinky stuff on video?”
“Well there is more to it than that. We both know that you are a complete slut. The only thing that has stopped you from advertising free services in the newspaper is that have limited yourself to playing with yourself. When you told me you had started butt fucking yourself with house hold items I knew it wouldn’t be long before you would slip up. If you just started to fuck on these videos you wouldn’t limit yourself to that, you would fuck anything with a pulse. The Cindy I know would cease to exist. Instead of my fun wild friend I would a greedy vagina moving from one cock to the next. My plan is have you satisfied by the most intense perverted sex acts rather than a mass of regular boring sex. But we have to protect those that are helping you too. If you start fucking strangers then your diseased pussy would get them into trouble. No, you will have to accept our terms completely or go off and fuck yourself.“ Tiffany ended confidently thinking she had her hooked.
Cindy frowned, “Maybe, I don’t know what the conditions are yet, but it sounds like I get told who I get to fuck. I have just felt what it is like to be with a guy, I think I should control all of that. I know you are trying to look out for me. And I appreciate the butt rape, I really do. But it is my life and I am just starting to have sex.”
Tiffany stood stricken. All her planning was coming undone.
Penny sat beside Cindy and started to play with her nipples. She spoke to Tiffany and said, “you have to understand Tiffany, Cindy has never had a dud root. She has only had her fantasies and a royal butt pounding by Tom. Tom even let her finish on his cock after he had cum. Not many guys would do that. Also, she is pretty, but once she gets a reputation, which will not take long, who will fuck her. She will still have her own choice, but only from the bottom of the pile.” Penny trailed her hand down past Cindy’s stomach and started rubbing between her thighs. “Cindy has no idea the perverted games we have planned. We have access to the most extreme sex toys and devices available. We have parties where a girl can have every desire or orifice fulfilled.” Penny put Cindy’s clit between her fingers pulled it back out of its hood. Cindy’s juices started dripping down onto Penny’s hand.
In an uneven voice Cindy asked, “So you would seriously have a guy dressed as a bum put a ring through my clit, attach a leash to it, and lead me through the streets?”
Penny’s eyes widened in surprise, “That is your fantasy? Well we could do that. Tiffany didn’t tell us the whole thing.”
Cindy moaned and said, “No, I didn’t tell Tiffany the whole thing. I thought she was a prude.”
Penny laughed, “I think there is more to Tiffany than you realise.”
Through heavy breaths Cindy said, “She may have set this up, but I have never seen her kiss a guy.”
“I will let you in on something then. Her deal with us is that we help you for a year if you agree to our terms, but she had to be a sex slave for a week first. Just yesterday I attached a bull clip to her clit and labia and led her to a party where she was gangbanged by five large black guys. She isn’t that different to you.
At hearing that Tiffany, her best friend, a total geek yet beautiful in her innocent way was treated like a fuck toy, she orgasmed for a third time leaving her feeling completely spent.
In a resigned tone Cindy said, “Okay, I’ll do it. I will be your fuck toy for a year. I will only fuck who you want me to fuck. Where do I sign?”
Penny stood up in her excitement. “Good, we were all hoping you would say that. And we are sure you will do well. But first you will have to have a trial week.”
“What? What are we trialling?” She knew that she was being set up for something. And it had to be something big, because she had already promised to be their sex toy. What more could they want?
Tom pulled a strange device out of a box and said, “we will be trialling you resolve. This is a chastity belt. As you can see it has a modern twist to it. These straps lock the front part over your pussy. It is made of a material that will allow your breath and stay healthy. See this thing at the top, that is a catheter so you will be able to pee. We put this tube down your pee hole and inflate the balloon at the end and it will stay in place. To pee you will just have to pull that little plug. All very standard. But what is special about this is the little vibrator that fits into your pussy. Now it won’t be deep enough to break your hymen, so don’t worry about that. By the way, we will have a great cherry busting party once the week is up, so don’t freak out. Now this vibrator is hooked as you can see, Now it will spin around right where the g-spot is. It also has a vibrate mode. I can see you are excited about that. Now see those three holes? This vibrator has three tubes of liquids. The first one is just Lubricant. The second is a cocaine compound and the third is a chilli extract. All of these functions of course are remote control operated.”
“Why would I want those liquid squirted into me?”
“Well, the lubricant could come in handy, say the person with the control wants to suddenly have the vibrator spin, it would be best if you had a squirt of lube. The cocaine compound will make you pussy extremely sensitive to pleasure for a short time. Now the chilli compound is actually made from the same stuff as Deep heat or Dancorub. It is somewhat diluted but will still give you a kick. That was added because Tiffany thought you were sick enough to get off on it. We said that if she wanted us to do that, she would have to have it tested on her. She cried like a baby, but insisted you would still like it. Either she is a good friend who will suffer to for you, or she is a sadist who wants to see your pussy burn. Either way, we had a Gyno check her pussy out afterwards and there was no lasting damage, so guess what? We wanted to have a chastity belt that could electrically shock you, but the batteries just didn’t last did they Tiffany?” Tom turned to Tiffany expectantly.
“Not the way you used that controller. I could barely walk for a day afterwards.” The funny thing was, that Cindy could not detect a hint of spite in that comments. What did that mean?
Tiffany continued, “The week is to see if you can go for a week without screwing someone without permission. If you try to tamper with the chastity belt so that you can fuck, we will be able to tell. If you do that, there is no deal. But if you do manage to be satisfied by remote control orgasms and by the people that you are permitted to fuck, then we will try to make as many of your fantasies come true as possible. What do you say?”
“Put it on already, geez you people like talk. Are you going to ask permission for everything you do?”