Tom and Serena

“But please! Tell me why you won’t go out with me. I love you,” Tom whined.

 “You don’t know anything about me. How can you love me?” Serena asked. “You just like to look at me.”

 Thomas did just that. He looked at Serena, and was struck again at how attractive he found her. Serena was not very tall, a bit heavy, and was hardly a beauty. But she had something that Tom found irresistible. He had known and liked her since the first day of orientation at college, and even gone out with her a few times. But it was not till his French class, during an interactive language drill where the instructor had flashed scenes of French life that it all clicked for him. Serena looked just like the women of southern France, olive-skinned and freckled, large breasted and slightly rounded. Exotic and sexy. Now, three semesters later, he was hooked. Serena represented the opposite of everything he was: Midwest, conservative, and boring.

 “You’re right about one thing, and wrong about another. I do love to look at you. I think you are gorgeous. But I also know about you. Your parents came from France...”

 “Grandparents,” said Serena.

 “And you speak it like a native.”

 “A native what?” Serena said.

 Tom ignored her. “You love coffee, books, jazz, and modern art.”

 “And that’s why you love me? Because you like coffee too?”

 “No,” Tom said. “Its... I just do. I like everything about you. I can’t stop thinking about you. I would do anything for you. Anything you asked.”

 Serena looked evenly at Tom, not speaking for a while. “Anything is quite a lot. Ok, I will make you a deal. If you can do everything I ask, I may change my mind about you. Come to my apartment tonight around eight o’clock.”

 “Fantastic. I’ll be there. God, thank you!” Tom said.

 Serena reached out, and grabbed his shirt near the collar. She twisted it, and looked him in the eye. “I am serious about this. You do as I say, and maybe we will be spending time together. But the minute you screw up, you are gone.” Twisting his collar harder, she said “You got that?” 

Looking at her evenly, Tom answered, with a bit of shake in his voice, “Yes. And I am serious too. I will do anything.”

 Serena let go of his shirt, and turned to walk away. Looking back, she said “Eight. Tonight.” 

At eight Tom was at Serena’s house. He did not quite remember what he did between the time she had left him and his getting there. He remembered a shower and a shave, and not much else. But here he was, about to knock, looking at a note taped to the door.  

“Tom,” it said. “Come around to the back door.”

 Tom stepped back and looked at Serena’s apartment. It was a typical college town conversion: an old two story house converted to an apartment on each floor. There was a whole row of identical houses, each one converted to student apartments. The back door was reached by going down the driveway shared with the house next door, and up the step. He looked for a name to be sure it was the same apartment, and not one that had been divided again on each floor. What he saw was another note.

 “Come inside the porch.” Inside the porch there was another note. “Take off all your clothes. Put these on. Kneel down. Wait” The “these” were a pair of handcuffs. A real pair, heavy, and made of chromed steel . With no key in sight. Tom thought for just a moment before beginning to take off his clothes. But he imagined Serena watching him through the window onto the porch, and started to undress. He carefully folded his clothes and put them onto the floor, then put on the handcuffs. He then kneeled down, and waited. It was several minutes before he heard anything from inside, long enough for a person to wonder if this was all a risque college prank. Oddly though, Tom was certain that this was real, and he began to be more excited than he had ever been in his life. Suddenly there was the sound of the inner door opening, and Serena was framed in the doorway.

 “Get up and come in,” she said. Tom followed her into what turned out to be the apartment’s kitchen, and was shocked to see that Serena had a roommate. “Are you going to stick around for this Anna?”

 Anna was a tall, thin, very attractive blonde. “No, I promised my study group that I would help work through some calculus problems.” She looked Tom up and down in the way Tom had seen men look at pinups. “But send him to me when you are done with him. IF you decide to keep him.”

 “Deal,” Serena said, as Anna got up to leave. “I guess it’s just you and me lover.” Serena grabbed the handcuffs, and led Tom to a door that led to the basement stairs. “Careful. I would hate for you to fall and hurt yourself,” she said, then laughed.

 At first Tom did not get the joke. Then he looked around the basement, and began to understand. He saw a huge X of wood against the far wall; hooks, some with ropes hanging from them, on every exposed beam; coat hooks along one wall filled with every conceivable type of whip, chain, and leather restraint.

 Serena waited until Tom completed his survey in stunned silence. “I certainly don’t want you to hurt yourself. That’s what I want to do.”

 Tom turned and looked at Serena. As if in answer to her next question, he said, “anything.”

 “We’ll see. Get your ass over there and raise your hands,” she said, pointing to a spot in the middle of the room. Tom walked over to the spot, and  noticed that he was under one of the hooks that had a rope strung through it. He raised his hands, and Serena hooked the end of the rope to his handcuffs, pulled it tight, and tied off the end. “Spread your legs,” she said. Tom spread them, and Serena tied first one, then the other to a rope that stretched from a post on either side of him. Standing up, Serena looked Tom in the eye and said, “Don’t put any weight on your hands. The cuffs have no give in them, and they will hurt you.”

 Tom stood in shocked silence. Serena took both her hands and ran them over Tom’s body from shoulder to thigh, then walking around behind him, she kept her hands on him as she felt his body from ass back up to his shoulders. “You can leave at any time. Just tell me you don’t want to do something, and I will stop and let you go. But that will be the end of it. I won’t see you again.” Walking back around in front of him, Serena grabbed each of his nipples between a thumb and forefinger. She suddenly twisted them while pulling up. “Do you understand?” She asked.

 “YES!” he squeaked through gritted teeth.

 “Good,” said Serena. “Now let’s begin.” Serena walked over to the wall, and came back with a leather cat-o-nine-tails. “This hurts, without doing any real damage. It’s a good way to start.” Serena swung her arm back, and let it come forward in a wide ark. Tom screamed, and leaned forward to try and avoid the blow, rising up onto his toes to try and get out of the way. Serena sighed, and then, hit him again. “Now lets get serious,” Serena said, and started to hit him quickly, and hard. Tom began to yell, and squirm out of the way. As the force of the blows became harder, and more frequent, he began to gasp, and then beg.

 “Please stop....Please!”

 “Do you want me to stop? Do you want to go?”

 “Yes, please stop! But not if I have to go. It hurts, but I won’t go.”

 “Good answer,” Serena said, putting down the cat. “I was about done anyway.” Walking around in front of him, she again played with his nipples. How does this feel?


 “How about THIS,” she said, as she pinched his nipples and twisted them.

 “Oh God, that hurts. Stop!”

 “Oh no lover. Not stop. Say, “I want to go now.” SAY IT!”

 “No! Not go, just stop! I won’t go unless you kick me out!”

 “You may change your mind before the night is over. I am certainly going to try and change it for you.” Serena let go of his nipples, and walked to a shelf against the wall. She came back with a pair of alligator clips. Then, pulling out on his nipples, one at a time, placed them on him. “Let’s see how long you can stand that,” she said. Serena then walked behind him, and grabbing him around the neck, as if hugging him from behind, pulled him close and spoke into his ear. “This is who I am. How do you like me now, baby?”  

“I love you!” Tom said through gritted teeth. “Do your worst. I will still love you!”

“If I did my worst, you would not be alive. But, you are doing fine so far.” Sliding her hand down to his ass, she said, “I should have had you clean yourself out. But I did not want to give you any warning. Next time, if there is a next time, I want you clean. Until then I will just have to use something other than my hand.” Going back to the cabinet, she returned with a butt plug, that had a pump attached to it. “Open wide!” Serena said, then quickly pushed the plug up Tom’s ass. “I think you will enjoy this. I know I will,” she said, then began to pump up the plug.

 At first the feeling in Tom’s ass was just uncomfortable. But then it began to hurt, and when the cramps began, it started to hurt a lot. Tom began to twist himself in his restraints. “Please he said!”

 Serena gave it a few more pumps, then let out some air. “Very good. I am impressed. I can’t wait to use my cock on you now. And I will...later.” Going to where the rope holding his handcuffs was tied off, Serena unwound the rope, and lowered his arms. “Bend over love. I want another shot at your ass.” Serena pulled the rope down and tied it to a hook in the floor. “Stay on your hands and feet, or else,” she said. Walking over to the wall, she came back with a riding crop. “This will hurt a lot more. Say whatever you want, but I won’t be listening until I am done.” With that Serena again pulled her arm back, and this time swung the crop at his ass. Tom let out a screech, and tried to pull away. Serena laughed, and swung the crop as fast, and as hard as she could. As she swung, Tom began to cry and scream, and begged her to stop. Serena continued to hit, harder and faster, until Tom’s legs gave out and he flopped on the floor. Serena, almost as if his falling were an act of defiance, only hit him harder.

 When Serena finally stopped, Tom’s ass was covered with a mesh of thick, red welts, some of which were bleeding. Throwing the crop down, Serena fell to her knees next to Tom’s head. Leaning down, she whispered in his ear, “How do you like me now?”

 “”said Tom, in broken sobs.

 Serena pulled Tom’s head into her chest, and said, “Oh!” almost like a child, surprised with a special gift. As she pulled his lips to hers, he fainted.

 Tom remembered, vaguely, being helped up the stairs, being cleaned up, and being tied to the bed. He remembered much more vividly Serena sitting on his chest, and stripping off her top. He remembered Serena cuming again, and again as she rode his cock, twisting his nipples, and squeezing his balls. Then nothing for a bit, as he fell asleep, or maybe passed out. Early the next morning, he woke on his stomach, with Serena sitting on the back of his legs. He tried to roll over, and discovered that his hands were tied behind him. Serena got off of Tom, rolled him over, then helped to pull him up to his feet, and said, “That was the most fun I have had, maybe ever. We are definitely picking up where we left off later. But now I have a promise to keep. I told Anna she could have you when I was done. And since I am going to keep you, you have a job to do.” Serena pulled Tom close, kissed him, and then spoke directly into his ear, “Don’t embarrass me. You will not like what I do if you don’t please her and do everything she says.” Then before letting him go, Serena gave his left nipple one more hard twist. She pushed him out the bedroom door, then down the hall to Anna’s room. Anna was waiting, wearing a pullover that came to just below her ass.

 “Come on in lover. I was kept up all night by your screams, and now I am a little pissed. Did Serena tell you how horny that makes me?”

 Serena watched Anna close the door, and then turned to crawl back into bed. She was just beginning to doze off, when the noise started. A thumping sound, punctuated by screams of joy, and pain. Serena closed her eyes, listened to the sounds, and waited for it to die down so she could get back to sleep.

 It was almost noon before she gave up, and went to get something to eat. “Now,” she thought, “I’m getting pissed”. She finished her meal, she began to plan how to take it out on Tom.

Anna was leaning against the door jam as Tom was propelled into her room. “Hurry up, Tommy boy. You don’t want to make me madder than I already am.” She stopped him when he got to the foot of her bed by putting a hand on his shoulder. “On your knees!” she said, kicking him behind the knee. Tom fell onto his knees, and almost toppled over, unable to control his balance or stop his fall with his hands tied behind him. “Stay up straight!” she said. Walking in front of him Anna added, “You have not learned much have you? When you are told to come, you come, and kneel. You say, “How may I serve you?” And you wait for a response. Got it?”

 Tom said “yes.”

 SLAP! Anna slapped Tom full across the face. “I did not say to say “yes”. Anna slapped him again, “Now lets try this again.”

Tom paused for a moment, then said, “How may I serve you?”

 SLAP, SLAP! Anna gave Tom two quick slaps across his cheeks, one with each hand. “That was for the delay. I can tell I will have to do some training before you meet my standards.” Anna walked to the table beside her bed, and put on a pair of fingerless gloves. “These are so I don’t wear our my hands working you over. So far you seem pretty dumb, and will need a lot of correction.” Anna ran her hand over Tom’s head, then grabbed his hair and pulled his head back so he was looking up at her face. “Or maybe I just kick you out now, and tell Serena I don’t find you acceptable. She might castrate you before she kicks you out, but either way you won’t come back here again. Is that what you want?”

 “No Mistress.”

 “Better. Now lets see what Serena has been doing to you.” Anna walked behind him, and looked at his back and ass. “Cute tush. I am surprised Serena didn’t put the moves on you. Then again, she said you were hooked. And since you’re here, she must have had a plan.” Anna looked closely at the marks that lined Tom’s ass in every direction. “Boy she did a bang up job on your ass. Bend over and put your head on the floor!”, Anna snapped. Then, kneeling on the floor next to him, she began you knead his ass with her hands. “I bet that hurts! I can feel how deep the bruises go. And still you stuck around. You really are hooked. I am proud of that girl! We will have to see how much you can take. But that’s for later. Now I have something else I want to do. Get on the bed!”

 Tom scrambled up, as best he could with his arms still tied, then leaning forward he plopped on the bed. “Move forward!” Anna said. I want your knees under you, legs spread, and your head down on the bed!”

 Tom moved to comply, and realized how open and exposed his ass was. He though that Anna was going to get a belt or some such thing and start beating him. And though he did not know how he could handle more abuse of his ass, he had long since given himself over to his new role. The pain and the abuse was secondary. What really scared him was that he might be told to leave, and never come back. He felt Anna get on the bed, and tensed for the first blow. Instead he was startled by her finger, cold and slick, probing his ass crack.

 “You had better relax, or this will hurt even more,” she said, as she slipped first one, then two fingers in his ass. “Nice. Tell me, did Serena fuck your ass last night?”

 “No, Mistress. All she did was inflate a plug in my ass.”

 “A virgin, no less,” Anna said. “Well, after today, you won’t be a virgin. You’ll  be a slut, and a whore, and my personal bitch.” Anna moved off the bed, and walked around in front of Tom. “Look up, bitch!”

Tom looked up, and saw that Anna had on a strap-on dildo that looked more than twice as large as his own cock. A groan escaped him before he realized it. “Impressive, isn’t it! Its my ‘Kong Dong’, over nine inches long, and three inches wide! I want you to imagine this rammed up your ass! Last chance to run, bitch. Once I rape you with this, we’ll own your ass, inside and out! So, what do you say?”

 Tom could not look away from the fake cock. As close as it was to his face, it looked larger than a horse’s cock, and he began to shake with fear and humiliation. Still he could not face the idea of being forced to leave, and never seeing Serena again. “I’ll stay.”

  Anna grabbed Tom’s ear and twisted it hard. “Not good enough, bitch! I want to hear you beg for it! Beg me to rape you!”

 Tom said, through a voice strained with fear, “Please Mistress. Rape my ass. I beg you.”

“That’s what I am going to do bitch.” Ann got back on the bed, and positioned herself between Tom’s legs. “How does this feel bitch?” she said as she ran the head of her cock up and down the crack of his ass. “Does this feel good?”

 Surprisingly, it did. Tom began to wiggle his ass in response. Anna held his bound arms in one hand, and used the other one to stroke his body. “That’s right bitch. Wiggle your ass. Show me what a slut you are. Beg for it!”

 “Yes Mistress. Please fuck my ass. Please!”

 “Not fuck. Rape,” Anna said, and grabbing his arms with both her hands, she rammed her cock into Tom’s ass as hard and fast as she could. Tom let out a shriek and tried to crawl away, but only succeeded in pulling Anna down onto his back. “That’s it bitch. Move for me. Let me know you feel it!” she said, as she began to pump in and out of his ass.

 Tom’s screaming was continuous now. He screamed and begged for Anna to take the dildo out of his ass, thrashing about and trying to get away. Anna rode him, and continued to pump the fake cock in and out of Tom’s ass. The combination of his screams, movement, and her excitement had caused her to cum almost immediately, so she was ready to settle in for a long fuck. “Yee-Ha. Ride’um cowboy. Keep moving that ass bitch. This is great!” she said, and continued to rape his ass. “I can do this all day, and you had better too!”

 Eventually Tom began to tire. His cries became less loud, and his movements less violent. “What, is that all you have bitch? I bet I can make you buck some more!” Anna said. She reached under Tom’s chest with both hands, and grabbed both of his nipples.” Get ready bitch,” she said, and dug her nails into his nipples. Tom’s screamed again, and tried to buck Anna off of him. Anna pinched harder, and ground her cock into his ass.

 Anna began to moan as Tom’s violent bucking caused her orgasm to build. She twisted harder, and dug her nails in deeper. Tom’s screams climbed the scale, louder and higher until it was a high pitched shriek, and his bucking under her became a rapid fit of gyrations. Finally, with a scream of “Oh God!” Anna came and released his nipples. She collapsed on his back, breathing heavily. Tom too could only breath and try to recover, uttering small cries whenever Anna rubbed her forefingers over his sore nipples. Eventually she pulled her hands out from under him, and pushed off of him. There was a sucking sound as she pulled the dildo from his ass, and Tom responded with a groan.

 “Very nice. We will be doing that again. But now its time for more training.” Anna untied Tom’s hands. “Get off the bed.”

 Tom rolled off the bed, and immediately fell to his knees, and said, “How may I serve you?”

 “You are learning. Maybe I won’t have to beat you to a pulp after all.” Anna stood close to Tom’s face, swinging her fake cock under his nose. Tom began to fear that she wanted him to suck on the dildo. “Get a good look at it Tommy boy. You are going to become good friends with Kong here. Serena’s is not quite as thick, but its longer than mine, and I am sure she will want to show you how good hers feels too.” Grabbing his hair, Anna turned Tom’s face up to her. “Take this off of me and put it by the door. You can clean this later. Then come back over to the bed.”

 Tom carefully unhooked the strap holding the dildo harness, and slowly lowered it off of Anna.  For several second he had a clear view of her body from the waist down. She was slim, with a slight swelling at her hips, a small patch of curly blonde pubic hair, and what could only be described as a gorgeous cunt. He could see her juices dripping from her lips, and smell the mix of sweat, cunt juice, and a hint of latex from the harness. “You’ll be getting an even better look in a moment, bitch,” she said, as she stepped out of the harness.

 Tom carefully set the harness down next to the door, at once terrified and fascinated by the size and shape of the cock Anna had used to rape him. Turning back to the bed he saw her leaning back against the pillows propped by the headboard. “Up here bitch. Crawl between my legs, and clean me out. I want to cum at least five times in the next hour.” Tom got down on his hands and knees, and crawled to the bed, then up between Anna’s legs. Beginning at her knees, he began to kiss up her leg, pausing to give a slight lick with his tongue between each kiss. When he got to her cunt he first kissed across it, and back down to her other knee, then moved back and planned a big kiss in the middle of her cunt. “Very nice. Keep that up, and I may not let you go back to Serena. Now do as I say....”

 For the next hour Anna gave explicit instructions on how she wanted to be licked, sucked, and tongued by him. She showed him how to slowly build her to a huge orgasm, and how to bring her off quickly so that she could enjoy a long, slow session. He was amazed at how much juice her cunt could produce, and at times it seemed like she could ejaculate like a man when she came. Twice she squeezed his head so hard with her thighs that he almost passed out. Once when sitting on his face, his tongue deep in her cunt, she reached out and pinched his nose closed so that he DID pass out. When he came to, Anna was riding him, bracing her hands on his chest, telling him to fuck her harder. Tom raised his hips to meet her downward thrusts, and kept pace with her as she fucked him faster and faster. Finally, as she came, Anna reached down and twisted Tom’s nipples again. Tom screamed, and froze with his hips arched in the air, while Anna ground her pussy onto his cock. Releasing him, they collapsed together, both catching their breadth.

 “Oh Tommy boy. You bitch. You definitely have your good points. It is going to be fun having you around. I think I had better return you before I decide to keep you for my own.”

 Tom felt dizzy as Anna helped him stand, and pushed him down the hall to Serena’s room. Noticing that she was not there, Anna pointed to the rug at the foot of Serena’s bed and said, “Down boy!” Tom literally fell to the floor, and was asleep before Anna had left the room.

 Anna went looking for Serena, and found her in the kitchen.

 “Have fun?” Serena said. Anna grinned as she sat down.

 “That is one nice fuck toy you have there. Are we going to keep him?”

 “I think so. He’s the same year as me and in the same program, so we should be able to keep him for a few years if we want,” Serena said. Looking at her friend, she asked, “so what did you do to him? I thought I was going to have to help you bury the body a couple of times.”

 Anna smiled and said, “I introduced him to Kong. The slut loved it. You know his nipples are very sensitive. Pinching them really gets him going.”  

“Really? That gives me an idea. Where is he?”

 “I left him in your room. He’s sleeping on the floor.”

 “Cool. I want to go to the hardware store and get some stuff for later. And one special toy I want to make to hurt his nips.”

 “You and your toys. If you make any more, we won’t have room for them in the basement.”

“If we run out of room, I’ll start hanging them from him. In fact, lets do that now. I want to make sure he does not go anywhere while we’re gone.” As Serena headed for the basement, she said, “I want to try that portable X-frame again. The last guy we used it on cried like a little girl, but I think Tommy is made of better stuff.  

Anna followed Serena down to the basement, thinking about the look that Tom would have on his face when he woke up. Already she was getting wet...


 Nancy knocked on Anna’s apartment again, and was surprised that there was no answer. When they had finished doing calculus the night before, she had told Anna she was coming by to pick up the extra assignment that she had missed. But it looked like no one was home. Thinking that everyone must still be asleep, she let herself in, and looked for a note.  

“Hey, anyone home? Anna, its Nancy. I am here for the homework!” Nancy waited, but still heard nothing. “Darn.” She decided to wait, and sat down in the living room. Glancing about for something to read, she picked up a music review magazine, and looked up reviews of new releases. Listening for some sound of Anna coming home, she heard instead what sounded like a dull thumping from down the hall. Curiosity got the better of her, so she decided to check it out.

 The noise was coming from Serena’s room. Pushing the door open, she was startled to see a young man bound and gagged on the floor. Startled, but not shocked. Everyone knew of Serena’s likes in sex, and Nancy had seen much worse at Serena’s invitation. There was that time when the frat pledge broke into Nancy’s sorority, and what Serena did to him! Nancy tried to push the image out of her mind, but instead remembered how hot it had made her. Looking down at the captive, Nancy said, “Caught in the spider’s web? You should be more careful.”  

Squatting down, Nancy examined Tom. He was on his back, with both his hands and legs crossed under him. Bars held both his legs open, and his elbows apart. She could tell that somehow the contraption kept both his hands and feet together at one point under the middle of his back. “Gosh, that looks like it hurts. You must be trussed up so they can eat you later. Tell you what, why don’t you help me pass the time?” Standing up, she said, “Be right back. Don’t go anywhere!”

 Nancy headed for the basement, looking for something she had once seen Serena use. It took her a while, but she found it hanging on a hook with some other gags. Running up the stairs, she went to Serena’s room, and stood next to Tom. “Got it,” she said. Now this will be fun.” Sitting on the floor, Nancy pulled off her shoes and socks, pulled down her pants, then stood up. Then she slid off her panties, and said “I bet you have had a lot of this lately! Want a closer look?” Nancy fingered herself, enjoying the wetness that was making her fingers slick.  Nancy stood over Tom’s head, and squatted down. “Hey, take a look at this.” Nancy held an odd looking device in front of Toms face. On one end it looked like a gag, but the other, it looked like a dildo. In the middle was a flange that obviously was designed to fit over a mouth. Grooves were cut into the side, and the flange had holes in it under each groove. “Ok, lets switch gags,” Nancy said, and unbuckling his gag, pulled it out of Tom’s mouth.

 “Please, I ...!” Tom began to say, but stopped as his head exploded in pain.  Nancy silenced him by slapping both his ears between the palms of her hands, hard.

 “That’s called ‘boxing your ears’. If you say anything, I will do it again. I don’t want to know who you are. Just shut up, and enjoy.” Nancy inserted the new gag in place, pulling it tight around his head. Then, lifting herself up over his face, she lowered her cunt onto the dildo attached to the gag. A low, long sigh escaped from her mouth as the dildo slipped in. “Ohoooo. Nice.” Then, kneeling over Tom’s head, she grabbed his hair, and began to move his head up and down.

 Tom’s eyes bugged out at the pain of having his head moved up and down. He tried to scream, but the gag worked as designed. All that happened was that the dildo end began to vibrate with his effort to cry out. Nancy groaned in pleasure, and pumped the dildo in and out faster. Suddenly she came in a torrent of juices. Looking down, she saw the Tom choking on the fluid, trying to breath through his nose while swallowing her cum.  

Nancy got up, and collected her clothes.

 Anna and Serena came home, laughing and joking about the reaction of the sales clerk at the hardware store when they told him what they wanted. Serena picked up a note on the kitchen table, and gave it to Anna. “Hey Anna,” she said, “what’s this?”

 Anna read, “Anna. Came by for the homework. You were gone, so I will have to get it later, Nancy. P.S. I used Serena’s new toy. See you tonight?”

 “This,” said Anna, “is from Nancy. I guess Tommy boy will have an audience tonight.”

 Anna and Serena looked down on Tom. He was still trying to breath through his nose while swallowing the remainder of Nancy’s nectar. “It looks like Nancy took our boy for a little ride.” Anna said. “God bless her, I did not think she had it in her. I don’t think she has even dated a guy.”

 “I knew she could be a player,” replied Serena. “You should have seen her face when I butterflied that guy at her sorority.” Serena stuck her finger in the still wet juices pooled around the dildo, tasted it, and smiled. “I think we have to have her over tonight,” she said as she scraped up more of Nancy’s cum, and rubbed it inside of Tom’s nose. Tom, for his part, began to turn red with the effort to breath. “I think its time we let Tommy boy loose. I bet his arms and legs must be cramped.”  

Anna helped Serena roll Tom onto his side, and Serena unlocked the small padlock that kept all the restraints locked to a ring behind his back. One by one she unhooked the cuffs on his arms and legs from the ring, and helped him uncoil. Not that it helped. Tom stayed on his side, still in pain, trying to get his muscles to work.

 “I can’t believe that thing does not cut off his circulation. How do you come up with these gadgets?” Anna said.

“I spend damn near every free moment fantasizing about this stuff. You should see the ideas I came up with that didn’t work.”

 “I have, if you remember.”

“That worked just fine,” Serena said. “He never bothered you again, did he?”

 “He never bothered anyone again, I bet. I doubt he can get it up yet. So, are you planning anything like that for Tommy boy here?”

 “No way. This here’s my little toy,” she said stroking his cock. I’ll mark him, and if he tries to leave before I am ready I will give him his nuts as a going away present, but other than that I am not planning anything remotely as bad as that.” Serena playfully slapped Tom’s nuts. “You hear that lover? I am not going permanently damage any important parts. Of course,” she said, while taking one nut between her thumb and fore finger, “I am going to hurt you. But I think you like that,” and squeezed his testicle. Tom began to thrash around of the floor, and screamed into the gag. “There,” Serena said, “that got his arms and legs moving.”

 “I guess the cramps have worn off,” Anna said, and laughed. “Now what?”

 “I guess we get this place, and him,” Serena said, while slapping his ass, “cleaned up for tonight. You want to call Nancy and see if she wants to come over?”

 “Done,” Anna said.

“Cool. Let me get Tommy boy going, and then you can have him.” Serena said. She helped Tom to his feet and unbuckled his gag. Dropping it on the floor, she walked to an overstuffed chair against the wall. “Come here,” she said.

 Tom immediately moved to her, and kneeled down at Serena’s feet. “How may I serve you,” he said.

 “Nice,” Serena said. “Anna did a lot with you in just one session. Then again, you were ready for all this, weren’t you?”

 “Yes my Mistress”

 “You do know that as long as you stay with me, that this is how it will be. You will serve me, and I will give your body pleasure,” Serena stroked his cock with her foot, “and pain,” then kicked him in the nuts. Tom groaned, and fell forward, and Serena caught him by the shoulders. “Tell me now!” she said. “What are you thinking NOW!”

 “How much I love you, and how hot you make me!”

 Serena looked down, and saw what Tom meant. Though she had meant to put some force behind her kick, and had caught him full on the nuts, his cock was hard, and standing straight up. “Very nice.” she said. “Have use for that. But first, suck on my clit.”

 Serena leaned back in the chair, hooking her legs on either armrest. Tom leaned forward and licked her cunt from the bottom, all the way to the top, trailing his tongue up her slit until he found her nubbin. Then using his tongue, he pulled her clit into his mouth, and began the gentle sucking that she had indicated she preferred the night before. “Very nice,” she said. “Very, very nice.” Soon Serena was writhing in the chair, and suddenly, with a scream, she pulled his head into her crotch, wrapped her legs around his head, and came violently.

 Serena relaxed her grip, and pulled his head from her crotch. Tom gasped for air.  “Almost done,” she said. “Now I want you to take that cock of yours and fuck me,” she said as she leaned back in the chair, again resting her legs on the arms.

 Tom stood up, and using the back of the chair as a brace, leaned in and guided his cock into Serena’s cunt. “Yum,” she said. Slowly at first, then faster, Tom began to fuck Serena. So many times, so many ways, he had dreamed of just this. Was it less than 24 hours since he first was invited into her house? And how many times had he done it since last night? He had lost count. Not that it mattered. Each time is was better than before, and each ache, each additional humiliation made him want Serena more. He began to fuck as fast as he could, feeling his orgasm close.

 “Don’t you dare cum without permission,” Serena said. “!” Serena began her own orgasm. “Now, God damn it! Cum NOW!” and Tom came with her, collapsing on Serena’s body. She held him for a moment, then whispered in his ear, “One more thing lover. Eat me out again. I want you to eat your own cum.”

 Tom kept his face frozen as he slid to his knees. Slowly he leaned in, but hesitated to begin. “Do it now, or I guarantee you will be eating more than just your cum. I have a lot of boys like you dogging my heals, and I can line them up if you want, and make you eat me out after each one!” Tom began to lick her cunt, digging his tongue deep into her cunt. “Suck it out, lover boy! You know,” Serena said, “you will have to pay for that hesitation. I won’t tolerate your failure to do what I say, when I say it. And I have to warn you, Anna has a hair-trigger temper, and if you do that to her, what she does to you will make you wish I had punished you instead,” Serena put her hand under Tom’s chin, and lifted his face from her crotch, “and believe me, you won’t like what I do one bit!” Serena let go of Tom’s chin, and he returned to her cunt. “Hurry up. You still have to service Anna before tonight, and you have a lot of cleaning to do. When you finish cleaning here,” she said, leaning back in the chair with her eyes glazed over.

 Tom again found himself kneeling in front of Anna. “All this talk of cleaning,” she said, “reminds me that you never cleaned up Kong. Since it is still dirty, we might as well use it. Get it for me, and put it on me.” Tom went and got ‘Kong’, Anna’s oversized dildo and harness. Returning to her, holding it in his hand, he still could not believe how big it was, fully 9 inches long, and almost three inches wide. Tom held the harness as Anna stepped into it, then fastened it around her waist. Cinching it tight, he looked at the huge cock just inches from his face, and then looked up at Anna.

 “Your choice,” she said. “You can lube it with your mouth, or take it dry. Which do you want?” In response, Tom moved to the bed, lay on his stomach, lifted his ass, and spread his cheeks as wide as he could.

 “Please rape me, Mistress,” he said.

 “Picking pain over humiliation? Good choice. It would have been sick, but I would have fucked your face for all it was worth, then taken you up the ass anyway.” Anna moved behind him. “This will hurt,” she said. “And you know how much I love that!”

 Tom tried to pull his cheeks apart, hoping that the dildo would fit in without too much pain. Anna waited as Tom strained, holding the head of the cock just at his entrance. Shortly Tom’s arms began to vibrate as he strained to keep his ass open. Just as his arms began to shake, Anna leaned into him, and grabbing Tom’s hips, thrust into him as hard as she could. It was a repeat of her earlier performance, and his reaction was the same, though this time his hands were free. Tom tried to crawl away from his tormentor, but Anna just hung on, thrusting with her hips. Tom thrashed under her, screaming and trying to buck Anna off of him. “That’s it fuck boy. Move your ass for me. Grind your ass while I pound you!”

 Tom continued to crawl until his head hit the headboard. “No place to go bitch! So stay there and move your ass!” Tom screamed, but did as he was told. Anna responded by fucking him harder as she approached her orgasm. Anna came much more quickly this time, but even so managed to hold off cuming for over half an hour. By the time she did cum, Tom was crying, and begging her to stop. Anna’s orgasm brought some relief, though Tom’s ass was still stretched and sore.  Anna lay on him for a moment, then turned his head to the side table where she kept her clock. “Less than an hour,” she said. “If we did not have so much to do for tonight, I wouldn’t stop in less than two hours. I guess to make up for it I will have to go for twice as long next time.” Tom whimpered in response.

 Rolling off of him, Anna’s cock made an audible sound pulling out of his ass. “Get this thing off of me, and get it clean,” she said. Tom moved to comply, and walked, gingerly, to the bathroom with ‘Kong’. Serena greeted him when he got in, and surprisingly, gave him a hug.

 “I see you met Kong, she said. I wondered what she was doing to you. Clean that up, then get in the shower yourself. You’re a mess!”

 Tom cleaned, then dried the dildo and harness. He climbed into the shower, and scrubbed himself as best he could while avoiding the parts of his body that were in greatest pain. To help he kept the water a bit cold, and by the time he was done, he was shivering. Getting out he shower he found a clean towel, and a maid’s apron. The apron covered his front from his nipples to crotch, just barely, and nothing in back.

 The girls had him help clean, all the while tugging at the apron, and reaching under to pinch a nipple or the head of his cock. When they were done to the girls’ satisfaction, they had Tom take off the apron and walk downstairs. Pointing to the workbench along the wall, Anna said “down boy.” Turning to her friend, she said, “Ok Serena, what do we have for the slut today?’

 Serena laughed, and said to Tom, “We went shopping today. Anna’s comment about your nipples gave me an idea, and I had to try it out.” Serena pulled a plastic box from a bag atop the bench, and held it up, “Ten foot of chain. About 10 lbs.” Reaching back into the bag, she pulled out two small bags, and said “Alligator clips, of the style known as ‘battery clips.’” Setting that down, she held up four paper clips. “And this will make something called “Serena’s Caress. Now watch.”

 Tom watch in disbelief as Serena opened the packages. First holding the chain by one end, she folded it back on itself till she had measured it into thirds. Holding the chain by the middle segment, she bent two of the paperclips so that the formed hooks, and she wired the hooks to the chain. She did the same with the ends of the chain, then picking up the clips, wired one to each paper clip. She spread her arms so Tom could see the result. Suddenly he realized that the four clips  were equidistant. She had made a long chain with four alligator clips spread evenly along its length. Holding up the middle two clips, Serena said, “These are going on your ball sack.” She let the chain drop from her hand, but held onto the ends. It made a clanking thud as it hit the floor. “These,” she said, holding the clips on the end, “go on your nipples.” Gathering up the chain, Serena put ‘The Caress’ on the bench, and pointed to the center of the room. “Go there.” she said.

 Not bothering to stand, Tom crawled to the center of the room. Looking up he could see he was under a beam that stretched between two posts. Eye bolts were spaced up each post and along the length of the beam.  “Stand up,” Anna said. Tom stood, and Anna lifted his left arm into a padded cuff that hung from where the beam met the post. She did the same to his right arm, then stepped back. He heard a cranking sound, and saw Serena turning a mechanism he recognized as a winch for hauling boats out of the water. By tracing the ropes that were being taken up back to where they were attached, he saw that they were attached to him. The ropes were the cuffs that Anna had attached to his arms. Slowly the ropes raised his arms, then the began to lift him off his feet. Just as he began to stand on his tiptoes, Serena stopped turning the winch. Anna then went to one of the posts, and pulled another padded cuff attached to a rope, and attached the cuff to his leg. Repeating the process, she attached his other leg. There was no winch attached to these ropes. There did not need to be. Anna just tugged until his foot jutted out to the side, and tied off the rope. Then she did the same to the other side, leaving Tom dangling from his arms, spread eagle in the air.

 Anna stepped back, only to be replaced by Serena. She held “The Caress” in her hand. “It will be a while before Nancy gets here, and we won’t need you till then. But I wanted to leave you with something, to make the wait more interesting.” Slowly, methodically, Serena attached one clip to is left nipple. Tom yelled as the teeth bit into his nipple, but Serena just smiled. She then attached the first of the middle clips to his ball sack, and the second next to it. She finished by putting the last one on his right nipple. Stepping back, she said, “That will hold you until Nancy gets here. I will come down every half hour to take of the clips and massage some blood back into your nipples and sac. Then,” she said laughing, “I will put it back on.” Tom groaned, and the two woman headed for the stairs. At the stairs Serena turned back. “By the way,” she said, “when Nancy gets here, we are going to offer her a treat. She gets to be the first one to gather ‘The Caress’ up...and drop it!”

 The both ignored Tom’s screams as the went up the stairs.

 Tom watched as the women came down the stairs. At first he thought it was Serena coming down to relieve the pressure from the alligator clips, but then he saw one, two, then three pairs of legs as the came down. They were laughing and making jokes, and taking their good natured time. Last was the woman who had fucked his face earlier that day with the dildo gag. At the time he did not know her name, nor did she want to know who he was. But he guessed this was the ‘Nancy’ they talked about inviting. When Nancy saw Tom hanging, spread eagle off the ground, she put her hand over her mouth, as if to keep from breaking out laughing.

 “Oh, my God!” Nancy said. “How did you get him up there?”

 “We told him to get in, and Serena cranked him up,” Anna said. “He doesn’t seem to mind, do you Tommy boy?”

“No, Mistress.”

 “So your name is Tommy. We meet again, fuck-face. Did you enjoy our little tryst?” What’s with the jewelry?”Nancy said.

 “That’s one of the reasons we invited you,” Serena said. “My boy here has been sporting his new toy for the last hour, and we thought you might get a kick out of being the first to put it to use. The other reason,” Serena said, “was to tell you this.” Serena grabbed Nancy’s arm just below the wrist, her thumb on the back of Nancy’s hand, a hold called a ‘goose-neck come along’. She pushed in with her thumb, and twisted her arm down, forcing Nancy to her knees. “Don’t play with my stuff without asking. Understand?”

 “Oh, fuck YES!” Nancy replied. “Let go of the arm, ok?”

 “Hey, no problem,” said Serena, “end of subject.” She walked over to Tom, and gathering the chain in her hand, said, “Let me show you how this game works. The chain is about ten feet long, and weighs about a lb per foot. As you can see, it has four alligator clips on it, one on each end, and two in the middle. We attached the ones on the end to his nipples, and two,” Serena lifted part of the chain out of the way, “are attached to his ball sac. The idea is to do this,” Serena said, as she dropped the chain.”

 Tom’s scream was so loud that it startled Nancy, which in turn made Anna burst out laughing. Suddenly all three women were rolling with laughter, as Tom swung in his bonds, saying “Please God, no, oh Jesus, no, no don’t do that, oh PLEASE.”

 “Nancy was the first to recover, and turned to Serena. “You have got to be kidding me. How could you do that! God, what did you do, rip his tits off?”

 “God, I hope not,” Serena said, laughing. “Look.” Serena un-clipped on of the nipple clamps, and pinched Tom’s nipple. “Red,” she said. She pulled on his nipple, and Tom screamed. “Sore, too. But no blood. Skin is a lot more tough than you might think. And its hard to cut someone with an alligator clip. But I am sure it hurts like hell. Want to try it?”

 Nancy went quiet for a moment, then said, in a subdued voice, “yes.” She gathered the chain up in one hand, and said, “What do I do?”

 “You drop it, you dumb ass,” Anna said.

 Nancy giggled, and said, “You mean, like this?” Again Tom screamed, and pleaded for them not to drop the chain, but this time he bucked in his restraints, causing himself to rock back and forth. Nancy quickly gathered the chain up again, and said, “How’s this? And this!” she said as she did it again. Tom’s screams were continuous now, and his body had begun to sway in and out.

 After the tenth drop, Serena said, “Stop for a while. I want to check his nips.” She quickly removed the clips from Tom’s nipples, and then his ball sac, inspecting each. “Look,” she said, pinching Tom’s left nipple. The women looked at his nipple, red and scraped by the clip. There was obvious thickening of the skin as the area swelled from the abuse, but no evidence of real damage. “The other is the same. His ball sac is even better, though I bet it hurts just as much.” Then rolling his nipple between thumb and forefinger, she said, “Its very sensitive now. That’s what I wanted. Tomorrow I want him crying every time I run my tongue over it.”

 Serena massaged his nipples in her fingers, alternating between gentle rubbing, and vicious twists. “I want each of us to do ten more reps, then we can cut him down.”

 Anna pushed to the front. “Me first.” Picking the chain off the floor, she snapped on the four clips. “Ready for me, bitch?” Tom tried to answer, but before he could say anything, Anna dropped the chain. By the time Anna had done it ten times, Tom was crying. The area underneath the clips was rubbed raw, and the area on his ball sac was red and scrapped. After inspecting it, Serena decided to move the nipple clips to one side, and do the same for the ones on his sac.

 Nancy was next, and this time made each drop a slow, agonizing production. By the end Tom was babbling incoherently between screams. Again Serena examined him closely, and found no permanent damage. Nonetheless, she moved the nipple clips to the other side, and found yet another spot for the ones attached to his sac.

 Nancy mused out loud that there was no point in doing this anymore. Tom was obviously broken, and hadn’t done anything interesting for the last twenty minutes. Serena looked at her with a smile that said clearly, “You don’t know shit,” and walked up to Tom, putting her arms around his neck. She said, softly, but clearly, “we are almost done with this love. Just ten more, and you won’t see this toy for the rest of the night. Just ten more. But you have to ask for them. And I don’t want you making a big fuss when it happens. So do it for me.”

 Tom looked down as he gently swung back and forth. He closed his eyes, and said “Please Mistress, drop the chain.”

 “Oh no, love. Look at me. I want to see your eyes. I want to see your pain. Tom looked at his love, and said, almost in a clear voice, ‘Please Mistress, drop the chain the first time.” Serena gathered the chain, and without preamble, dropped it. Tom jerked, but gritted he teeth, and said, “Mistress please, drop it a second time.” By the time he had asked for the tenth drop, Nancy was almost in shock, and even Anna seemed dumbfounded.

“No way he could do that if it hurt him that much before. He must have been faking!” Nancy said.

 “Would you like to try it?” asked Anna. Nancy looked at her, but did not respond. Serena, picked up a towel and wiped down Tom’s chest. Small streaks of blood were clearly visible on the cloth. Serena untied the rope holding Tom’s feet, then went to lower him from the ropes that held him in the air. Tom swayed as his feet touched, but was able to stand. Serena tied off the rope, and then released his arms. Holding him closely, she guided him to a mat on the floor to rest.

 Serena turned to Nancy, and said, “Would you like to see what we have been doing to my slave?” Nancy came over and kneeled next to Tom. Serena pulled him onto his side so Nancy could see the marks on his back and ass, the oldest of which were from more than a day ago, and had begun to darken, revealing deep bruising. Nancy traced the ugliest with her fingers, making Tom wince with each one. She then ran her hands up and down his back, feeling the scrapes and cuts, and watching Tom flinch and whimper. Serena rolled Tom onto his stomach, and spread his legs. Nancy saw the ugly bruising in his ass crack, and spread his cheeks for a better look.

 “What did this?” Nancy asked.

 “Um. Tarzan meet Kong,” Anna joked.


 “Anna has a dildo she loves. Its rather big, so she calls it ‘Kong’. I am afraid my boy here had several run-ins with it,” Serena said.

 “Kong?” Nancy said. “How big is this thing?”

 “Bigger than any real cock you’ve ever fucked,” Serena said.

 “I don’t fuck real cocks,” replied a blushing Nancy. “I don’t like men much.”

 With a gleam in her eye, Anna said, “If you want, I can show it to you. I keep the beast upstairs. Tommy boy just got done cleaning it for me before you got here.” Reaching out, she took Nancy’s hand. “Come on,” she said, leading Nancy to the stairs. Looking back over her shoulder, Anna asked, “Do you need help with him?”

 “No,” Serena said, and watched them leave. Serena lay down beside Tom, stroking him gently. “Shush,” she said. “We’re done for tonight. Later, after you rest, we can play. And you’ll have some fun too...after a while.”  Slowly, Tom began to breath more shallowly, then, he began to snore. After a bit she heard a thumping, and yells from upstairs. Raising her head to listen closely she could distinguish yells of both pain an pleasure. Laying back down, she continued to stroke Tom as he slept. She pulled a cover over him, and lay down next to him, cuddling close to share the makeshift bed. Her last thought was to try and remember to ask Anna if she had fucked Nancy in the ass, cunt, or both.

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