It all started when Sebastian Hale had his eyes on his new assistant. With him being a ladies man, and to add to that, he was rich, single, owned a luxurious condo and a red Ferrari, so there wasn’t a woman he couldn’t get. He was tall, had dark black medium length hair which stuck out at many places, dark green eyes which many women admitted they can't resist, and a very muscular tanned body.
He eyed her through the glass windows as she was arranging her new desk just outside his door. She was small sized, short, thin with brown blondish hair. She had perfect b cups which complemented her body. Her ass stuck out to give her body this perfect curve. He watched her as she was talking and laughing with the copyboy, she had hazel eyes, perfect ebony skin, and dark red lips he was now urging to taste. He felt a bulge in his pants as he thought on and on about the things he wanted to do to her.
He snapped out of it when suddenly she walked towards his office, and knocked. He straightened himself on his chair, "Come in", he said. She slowly walked in, looking as perfect as ever, "Thank god I let bill choose my assistant..." he thought. "Hello Sir, my name is Latonya; I'm your new assistant" she said, breaking into his thoughts. Her voice was so soft, she seemed so innocent. He sat still for a minute, just looking at her, "snap out of it!" he told himself, "I've always got who I want, she's just like all the others". He then smiled confidently and decided to work his magic now rather than later, he got up from his chair and went up and stood in front of her, putting a hand out, "My name is Sebastian Hale" he said as she shook his hand. "And you are the most beautiful woman I've ever seen" he went on. "Umm thanks I guess." She replied uninterested. He decided to try again, "you know if all the other assistants were half as beautiful as you none of the guys would ever stop working". He waited for a response but she just looked at him as if he had insulted her.
He was shocked, this line always worked on girls, he didn’t expect her to do anything but just at least fucking smile!
He decided to get straight to the point, "look, your too beautiful alright? And I'm an okay looking guy too, and this place doesn’t have anything against employees dating each other, so what do you say you and I go out tonight?"
"I don’t date." She said coldly. "Hahahah, baby everybody dates!" As he said this he tried to softly touch her face but before he could she put her hands on his dick and squeezed his balls tightly. Even though he was wearing breifs and pants she had a pretty good grip over them.
"OOOOOOWWW" yelled Sebastian. "Listen you" she now said in a cold voice. "Don’t ever try to fucking touch me again! You can't handle a night with me, yet alone a date, you can't even handle this for fucks sake!"
"LET GO" he yelled again, unable to bear the pain as she squeezed harder. She then finally let go while he fell to his knees, holding his balls. He looked up at her; she took a step back, smiling at him. He was too ashamed, so he decided to get over the fact that she just abused him and try to keep what's left of his pride.
"Oh yeah?" he said, "Try me then!" She looked back at him, still smiling; he was still on his knees, holding his balls, she bent down so she was face to face with him. "Wanna bet?" she said. He nodded, he didn’t know what she really meant by can't handle, but obviously his ego didn’t make him think that it might be something he really can't handle. "Me? Can't handle? She must not know me at all!" he thought.
"Okay" she said. "if I win, you wear nothing but a pink thong to work tomorrow, and if you win, you can have me after tonight, whenever, and wherever you want, agreed?"
He didn’t even need to think, "Is she fucking serious" he thought, "She's willing to be my bitch as long as I want? We both know I'm not gonna lose this"
"Agreed!" he said as he got up with a cocky smile on his face.
"Alright then" she replied as she got up too. She then went to his desk, and bent over it; he looked at her ass as it came in full view in front of him. The thought that he could have that ass after tonight turned him on.
She took a piece of paper and wrote something on it, she then walked back towards him and stood in front of him. "This is my address, don't chicken out" she said, and then she unzipped his pants, put the paper in his briefs' and turned to leave, "be there at 10" she said just as she closed the door behind her.
Sebastian was eager to find the house, thoughts of what would happen when he reached there was a total turn on, he touched and rubbed his cock as he drove, his eagerness growing more and on, finally, after 30 minutes of driving, he finally found it. It was a small house, almost looked like a cottage since it had a chimney with smoke coming out of it. He sat in his car for a minute, checked whether the condoms were in his pocket, sprayed some breath mint, and got out of the car. He even bought some chocolates, hoping that it would at least loosen her up a bit. When he reached the wooden door, he knocked twice and waited. After a couple of minutes the door opened a bit, it was dark inside and he couldn’t see anything, "Come in" he then heard her sweet angelic voice say from inside the darkness.
He stepped inside the house but obviously he couldn’t see a thing, he then saw her shadow next to him. She walked forward and he felt her put something in his pocket, "If you feel like you can't handle, just read the words on this paper to me and I'll stop" He was quiet for a minute, "Are you fucking kidding me?" he then finally said, "Do you even know who I am? I once gave a girl four orgasms in an hour and you're telling me I can't handle you?"
She replied by only saying "Follow me". He did so without even touching the paper and went after her. They then reached to a door which apparently led to the basement, while she was walking down the stairs, it got brighter, "She lit candles for me" he thought. As they reached the bottom of the stairs, he saw her clearly. She was wearing this tight black leather outfit that made her look like a sex god. Her curves were just perfect, she was wearing a black bra only, so she was bareback, and leather pants that looked like they were going to burst from how tight they were around her ass. He couldn’t help it, he was already a little turned on from rubbing his dick in the car, but the image of her in that tight outfit, showing the curve from her waist to her ass was too much. He started to rub his cock again and was starting to get hard.
He took his eyes off her for a second to look around the candle lit room, horror struck his face when he saw what the room contained, there wasn’t any candles, but a fireplace instead, now he new what the chimney was for, but that wasn’t the thing that horrified him, it was the shelves that were next to the fireplace, shelves and shelves of toys, sex toys, toys that look painful. And there were these black like chairs and tables with straps on them. Without thinking, he threw the chocolate box on the floor and put his hands in his pockets for the piece of paper but before he could grab it, he felt two set of strong hands hold either sides of his arm and lifted him up towards one of the tables.
"LET ME GO" he yelled, trying to fight back, but the arms holding him were too tight. They threw him on the table; he turned around, and finally saw who was holding him. They were two men, huge muscular men, maybe each were double his size, bald, and also wore leather shorts. There was a hole in each of their shorts so their dicks could be clearly seen coming out of them. They were huge, maybe 14 inches each. His dick was only 7 inches and he took pride for it, but this was just huge. Before he got time to react, they moved forward and stripped him off his clothes, he tried to resist but his attempt seemed pathetic, when he wouldn't let them slid down his pants or life up his shirt, they just tore it off, and threw his clothes towards the corner of the room, with the piece of paper, his only way out, in one of the pockets.
He was sitting with tight briefs on the table, unable to move from fear, finally managed to find his voice and said "Who are you people? Why are you doing this?"
Latonya stepped forward from the shadows, he almost forgot she was there, "We're here for the bet aren't we" she said with a sick smile on her face. Before he could answer the two men grabbed Sebastian again and forcibly tied him to the table in a way the he was on his knees, legs spread wide apart, with his head also strapped on the table, so his brief wearing ass was stuck out in the air. He felt so vulnerable and weak being in that position, he was helpless. Latonya lit up a cigarette, but didn’t smoke it, she went behind him and before he knew it he was screaming in pain, "OOOOOOOOOWWW YOU BITCH, YOU CUNT". She had burned the cigar through the front of his briefs so the end of the cigarette burned his dick. "Cunt? From now on you call me mistress understood? Otherwise there will be consequences" She said coldly. "YOU’RE A FUCKING CUTTING" he said, still screaming. "Boys, strip him, I'll show this bastard who's the cunt" she replied fiercely. One of the men moved forward and tore off his briefs so now Sebastian was butt naked.
Sebastian saw her walk towards one of the shelves and pull out something, it looked like a butt plug. He wasn’t sure, but she made it clear that he was right when she went towards his ass and stuck it into him, he felt pain through his ass, from the burn and from the plug, he had never had anything in his asshole before, "OOOOWWW" he screamed, "I'M SORRY MISTRESS, TAKE IT OUT PLEASE" he went on. "You think that was it?" she said, laughing now. "Baby you haven't seen anything yet", she walked back to the shelve again and pulled out a long black whip, it looked deadly.
"NOOOOOOOO…" he began to scream but one of the men went and held his mouth shut, and before he knew it, he felt the whip hit him brutally against his ass. The pain was unbearable, she kept on whipping him one after another, and she had no mercy on him at all. She hit as hard as she can while saying things like "I'll show you who the cunt is" while laughing cruelly from time to time. It felt like the skin was peeling off where the whip hit. After a while she stopped, relief took over him, he thought it was all over her, but a minute later he saw her walking to one of the shelves again and pulled out a long stick with small leather straps, "ARRRRGGGHHH..UUGHGHGHGH" he tried to scream but the man's hand was too tight around his mouth. And Latonya started whipping him again, this time, it burnt and stung more, pushing the butt plug in his ass more and more, increasing the pain to something he'd never thought he'd feel before.
He didn’t know how long she kept on whipping him; he was almost unconscious from the pain, but as time passed he became almost numb to it, he couldn’t feel anything at all. He had never felt so vulnerable before, so embarrassed and humiliated the way he was. She then finally stopped, and the man removed his hands from his mouth, but Sebastian couldn’t say anything, he felt weak. Latonya came in front of him and bent down to his face, "Now, who am I?" she said in a whisper, "you’re my mistress" he replied weakly. "Good" she replied, moving towards his ass and touching it slowly, he was sure there was permanent damage there, but her touch made it feel a little better. "Now I think young Sebastian here deserves a little reward for learning his first lesson, doesn’t he boys?" she said, speaking to the two men. "Now flip him" she told them, "But before you do, remove his butt plug and replace it with the larger one"
One of the men did so, removing the small butt plug and inserting the larger one, Sebastian's asshole now got used to being stretched, so when the man inserted the larger one, Sebastian actually got turned on by it, he did feel pain but it felt good, he never felt this way before, "Aaaaaaahhh" he moaned slowly, he wanted the man to push it in and out, he needed speed, he didn’t care if it was a man, he just needed it so bad. "I knew you would like that you little slave" sneered Latonya, "Now flip him". The two men came forward and unstrapped his arms and legs, and flipped him over the table like their mistress had ordered. Sebastian didn’t put on a fight, he was too weak from the whipping, his ass was too sore, but he was also very turned on from the butt plug. The two men lay Sebastian on the table, and strapped his arms and legs to it, his legs were bent and also wide open, like the position a woman is in when giving birth.
Latonya came towards the table and grabbed his dick, fiercely yet somehow gently, she then started rubbing and massaging it, he got hard immediately, groaning as rubbed him harder and harder, "you like that don’t you, you little bitch?" she teased, "Y-yes mistress, more mistress" he replied. She started sucking him and licking his dick and his moaning got more rapid she put his whole dick in her mouth and starting sucking him. She worked her tongue around it perfectly; he came so close to orgasm, "I'm g-gona c-cum mistress"
Immediately after he said that, she let go of him and walked away, leaving Sebastian with nothing when he was just about to cum. He realized what had happened and begged weakly, "Mistress p-please, c-come back mistress, please" this was worse than getting whipped; it was just too much torture. He wanted something to release all that cum he had, but he couldn’t without his mistress's help. He then turned to one of the men standing at the edge of his table, "Sir? Could you please pull my butt plug in and out of my ass? Please sir" he couldn’t believe the words coming out of his mouth, in another situation he would rather die then ask a large naked man this, but this was different, he wanted something, needed something.
The man just looked at him, and suddenly Latonya appeared next to him, "What did you say?" she asked Sebastian. He was embarrassed he couldn’t even answer her, "you want it in and out? I'll give you in and out" she said, putting on her fierce tone again. "Bruce" she said to one of the men, "Give it to him". Sebastian saw the man come and stand between his legs, holding his dick. Then the other man went behind him and pushed on a button which made the straps pull Sebastian's legs up so his ass was on perfect position in front of the man's dick. He suddenly realized what was going to happen and screamed like he never screamed before, "NOO PLEASE, MISTRESS, NOT A MAN MISTRESS PLEASE, NOT HIS DICK, MISTRESS PLEA..." the other man tried to shut him up but the mistress stopped him."Let him scream" she said, "It'll just get Bruce harder"
And with that said, Bruce roughly pulled out the large butt plug, the size of it not even being half the size of his cock, and slammed his hard 14 inch dick into Sebastian's asshole, "AAAAAAAAAAAAAAAAAAAAAAHH" screamed Sebastian, "MISTRESS NO, IT'S TOO BIG, MISTRESS, ATLEAST SOME LUBE, PLEASE MISTRESS, IT'S TOO BIG"
Latonya ignored him as he screamed and begged her, she just watched with pleasure as Bruce slammed his cock roughly into Sebastian's asshole, "You'll get used to it eventually baby" she told Sebastian as he let out another shriek. Sebastian felt like his asshole was gona tear open, the pain was too much, the man's dick was just too big, and he just kept on fucking him harder and harder. After a few minutes, the man was going easy on him, fucking him slowly and gently, Sebastian couldn’t believe it, but he started enjoying it, he couldn’t believe that he got turned on by a man, he was even moaning slowly from time to time and started getting hard again.
Latonya climbed over the table and Sebastian saw that she had removed her pants, she stood over him with her pussy in full view, it was clean shaved, and it looked so beautiful, she was so beautiful, she then grabbed his now fully hard 7 inch cock and put it between her pussy walls, Sebastian couldn’t get any happier, he wanted her badly, wanted to cum badly, "Listen you little bitch" she told him, "Whatever happens, whatever you feel, you will not moan or make a single sound, or else you will get punished"
And with that, she went lower so his dick was in her wet pussy, she pushed herself in and out, slow at first, but then faster and faster, Sebastian also tried pushing his dick up and down to keep up with the phase but the straps made it hard for him, as she pushed herself on his dick harder, Bruce also fucked him harder and harder, while the other man was watching.
Sebastian felt amazing, he had never felt so much pleasure before, it was hard to keep from moaning but he controlled himself. He fucked Latonya harder and harder and he was on the verge of cuming, she noticed that and said "Just a little more baby". He tried to hold himself but Bruce fucked him even harder so he couldn’t, he came into her with so much pressure, his body twitching, he almost felt dizzy from the pressure of the orgasm, it was the best one he had ever had, also, he couldn’t help but moan as he did so, "AAAAAAAAAAAAAAAAAAHHH" he screamed out. Abruptly after that both Latonya and Bruce stopped, and she got off the table and wore her pants, leaving Sebastian breathing rapidly on the table. He thought it was over, even though it was painful but yet amazing in the end, he knew it was over until he heard her say,
"Didn’t I tell you not to make a sound?" she told him coldly. That line scared the shit out of him, not because of what she said, but cause of the tone she used with him, she had used that tone twice before, once, right before she whipped him, and then another time, right before she made Bruce fuck him. "What more could she do to me?" he thought. He looked at his clothes lying on the floor in the corner of the room, the paper was in his pants, and he needed that paper. Latonya broke into his thoughts when he saw her walk towards the shelf again, she took a glove and wore it, and then she took down a long, metal rode, which was twisted in the letter L at one end. She then saw her walk in front of the fireplace and stuck the L shaped end into the fire, turning to Sebastian while doing so; she smiled at him cruelly and then ordered the men, "Boys, why don’t you put young Sebastian here in proper position for his punishment"
"Mistress…" Sebastian said in a low voice, his voice was stuck in his throat from fear, he knew what was going to happen, he knew he couldn’t do anything about it, he knew it was coming. Both men unstrapped him again and took him to another table, this one was metallic, all they did was bend him over it and strapped his hands and legs again, so now he was in the position of a man having a prostate exam. While they did so, he tried to fight back has much as he could, but his attempts at it just seemed pathetic. "Mistress I need my pants, I need the paper mistress, you were right mistress, I can't handle you, you win mistress" he said calmly. He didn’t know why he was so calm; probably because he was scared shitless, he was shaking he couldn’t even scream.
She was still standing near the fireplace, burning the end of the metallic rod, "Well I'm sorry Sebastian" she said softly without even looking at him, "but the only way you could leave here is for you to read that piece of paper, didn’t I give you the chance to do so when we were at the door?" she said softly "Plus," she went on "this is what you get for disobeying me"
She pulled out the metal rod from out of the fire; he saw that the end was red-orange. He stayed quiet, but as she started walking towards his ass, he couldn’t help it, he lost it completely, he screamed like he never screamed before, "MISTRESS NOOOOOOOOOOO, PLEASE, MISTRESS I'LL DO ANYTHING, YOU CAN WHIP ME AND FUCK ME, BUT NOT THIS MISTRESS, PLEASE" while saying this, he actually started crying, actual tears were running down his face, this was the most embarrassed he had ever felt in his life, the most fear, he wanted to die right there and then as he begged the tiny woman for mercy. "M-MISTRESS N-NOOOO P-P-P-LEAAAASE" he yelled between sobs.
She was now behind him and he couldn’t see her, he knew it was gona happen any moment, one of them men came and put his hands over his mouth, he tried to resist, he tried to break through the straps, but he just couldn’t.
And then he felt it, he felt the hot metallic rod burn his already bruised ass. Now this was the worst kind of pain he had ever felt. "AAAAARRGGHHH..UURRRGHGHHHHH" he screamed through the man's hands. But Latonya did not remove the rod, it was still burning his ass, he felt like his whole body was on fire, he wanted to die, he just couldn’t handle the pain.
"Give him his pants" laughed Latonya, still not removing the metallic rod from his ass. The man who wasn’t holding Sebastian's mouth went over and got his pants, took out the piece of paper and held it in front of Sebastian's face, teasing him because he knew Sebastian won't be able to say the words unless the other man removed his hands. "GGGRRRRRR…AGHGHGHGHG" Sebastian tried to scream but only muffled sounds came out.
"Hahahaahhh, you can let go of him Bruce" she told the man holding Sebastian's mouth. The second he let go, Sebastian screamed out the words written on the piece of paper, "I WILL N-EVER BE ABLE TO H-HANDLE MY MISTRESS". And with that, Latonya removed the metal rod from his ass and threw it on the floor, she went over to his face and kissed his mouth deeply, "You can go now baby, I'm sorry for all of this, but you've been a bad boy, and now I made you good" she said.
Sebastian just looked at her, with tears all over his face, his asshole was sore and felt like it was bleeding from Bruce's dick, and his ass was not only sore from the whipping, but the burning sensation there was still unbearable.
Latonya went over to his ass and kissed the part where she had burnt him, then ordered the men to untie him.
She then gave Sebastian back his clothes and a small pink bag, "I won the bet, you know what you have to do" she said, pushing the bag which had the pink thong in his hand, "Oh, and thanks for the chocolates" she said while picking that box up too and taking a bite, "it was a nice gesture, you must be such a gentleman"
Sebastian didn’t say a word, he just took his torn clothes and left. "I'll keep my side of the bet" he thought, looking at the bag. "She might’ve won this time, but it's not the end of my story with her" he smiled to himself as he drove away.