Weekend Slaveboy

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Serves you right slave for even thinking of getting an erection in my presence without my express permission. Come here so I can remove your collar and cuffs. Time to get you cleaned up. Since you didn't complete your chores, yes it is now 2 p.m., I am going to break you!" So saying Mistress Ruth roughly took off the collar and cuffs and then put the key in the padlock on his chastity device. "Remember that you are not to touch your cock unless I order you to do so." As the cock cage came off, his cock did what was only natural in his mind and began to swell immediately. After all what could she expect he thought as she was still standing there naked.

Handing him a bottle of hair remover she barked, "Now step in the shower and rub this hair remover all over. I do not want one single hair left below your neck. I know you shaved your body before you came over yesterday, but I want you hairless and very smooth for what you will have to endure later today. Yes I will be watching your every move, or else you might be tempted to play with your cock and you know that would be a most heinous offense for which you would be severely punished!"

Doing as ordered the slave stood in the shower stall motionless as he felt the hair remover doings its job. After the required time according to the label that Mistress read, she finally ordered him to take a shower. "You need to wash that off completely boy, but not hot water, just cold. I am not wasting money on hot water for a slave! And maybe that will help your little problem hanging between your legs!"

So standing under the cold water spray, slave did as he was told and scrubbed himself clean, and then repeated the entire scrubbing down process twice more as his Mistress stood there laughing at him. "Get out now and dry off. And be quick about it, I have lots to do to prepare you yet."

As he dried off he realized he was shivering, although he wasn't sure if it was from the long, cold shower or the fear he felt as she mentioned having lots more to do to prepare for whatever she was planning. After he finished, he smartly knelt there and waited for her to return but the longer he pondered his shivering the more he truly began to believe it was being caused by fear.

When Mistress Ruth returned she had gotten dressed, if you could call it dressed. She wore a black bustier that just covered her nipples with garters attaching her stockings, a black thong that barely covered her shaved pussy, and black 4" high heels. The mere image of her again caused his cock to want to swell which was immediately noticed by his Mistress. Quickly buckling a heavy black leather collar on his neck, she snapped a leash to it and literally pulled him down the hallway to her bedroom. Leaving him in the middle of the room, she went to her closet and returned with heavy black leather cuffs for his wrists and ankles and strapped on tightly. Then she hooked a 12 inch chain between the ankle cuffs, which added to his rising apprehension.

Reaching down and grabbing him by his balls she demanded he stand up which was awkward with the chain connecting his ankles. But with a painful pull on his balls she got him upright with what seemed to the slave to be little effort. "Bet you didn't know how strong I can be when needed, did you slave?" queried his grinning Mistress. "That little ball tug seemed to deflate your slave cock as well. So let's get that useless thing locked up again before it becomes more of a nuisance!"

Nervously he stood there waiting as she dug through the bottom drawer of the dresser, allowing him the pleasure of seeing the nearly naked cheeks of her rounded bottom. But when she returned, she showed him the new cock restraint that she intended to use.

"Now notice the lovely features of this new device I bought just for you. It is rather small in diameter which won't be a problem for your cock!! And see how it folds open so it is easier to put on you. Then you just snap it closed and add the padlock that also locks the strap around the back of your balls so it cannot come off. Oh and I almost forgot, let me hold it close so you can see all the lovely sharp spikes on the inside of the tube. Now these won't be a problem with your little cock unless you try to get erect and then, well, let's just say I hope it will be quite painful!" And with a huge sadistic grin on her face, Mistress Ruth quickly installed the new cock restraint on his now really useless cock. As she snapped the lock shut her grin became an evil laugh. "Oh, what is she planning on doing to me" was the thought that raced through his brain.

"Almost ready! Now turn around and bend over so I can hook your collar to the end rail on the bed." As he assumed the position, she wrapped the leash tightly around the rail, leaving him bent sharply at the waist with his ass fully exposed, in a position that at the moment made him very uneasy.

Showing him a butt plug that Mistress described as the biggest one she had used on him previously, she used that soft sensuous voice to tell him, "Now I am going to ram this in your asshole boy and you are not under any circumstances to let it slide out. Now you know why I have made wear your various plugs for hours on end before, use that training to keep this big one in your little fuckhole. It will help stretch you out for the ass fucking I plan on giving you later. It will be with a much bigger strap-on than you have taken previously. I imagine it will be quite painful, so I would really concentrate on keeping that plug in to loosen you up! Now I will be back in a little while...don 't run away like a scared little boy now!!"

Leaving him bound like that to the end of the bed with his mind starting to race out of control with fear, Mistress Ruth made her way out to the living room where she warmly greeted Laura and Claudia. "Thank you so much for making the trip to help me out."

"This is going to be our pleasure dear. Claudia and I discussed on the trip out what we might like to do with him this evening if you don't mind" replied Laura.

"Ladies, you are free to do whatever you like with him tonight! He thinks he has limits, and one of his greatest fears is for me to expose him to anyone else. Well we are about to blow that limit all to pieces, so anything you want to do is fine with me. And if it breaks another of his limits, well that is all the better!" was Ruth's reply. "Now let me go fetch the boy before he pisses himself with fear worrying about what I have planned!"

Returning to the bedroom, she observes her slave with his plug firmly in his soon to be violated fuckhole. And several lovely red lines across his ass from the caning she gave him earlier. Picking up the razor strop, she explained to him that although he had some nice cane marks on his ass, she wanted it to be fully colored. "Don't you agree slave, that it would make the cane marks look even better?" But before he could even think of an answer, his Mistress laid the first hard stroke across his ass. Then a second and third stroke that he deemed to be full force strokes bringing a cry of agony from his lips. The sound only encouraged Mistress Ruth to deliver another nine strokes, bringing the count up to an even dozen.

"There, there, now that looks so much better!" exclaimed his Mistress. "Now let's release you and have you back on your all fours like a good slave." And with that she released his leash from the bed rail and he dropped to the floor as she wished. But them she approached him from behind pulling his head back. "Now open wide, I have this lovely three inch cock gag to keep you quiet!" As she stuffed it fully into his mouth and buckled it behind his head, she once again used that sensuous voice to inform him, "there now we don't have to worry about you opening your mouth when you shouldn't tonight. I am so going to enjoy what is about to happen to you!"

And grabbing the leash she started out the door and down the hallway toward the living room.

Part 3

Pulling hard on the leash, the slave was forced to crawl along behind her although the short chain hobbling his ankles made the task much more difficult. As they entered the living room Mistress Jerked the leash even harder, pulling him to a stop in the middle of the room. Leaving him with his face to the floor, he heard what he thought were feminine giggles...but he dared not look without his Mistress's express permission.

Then Mistress Ruth demanded he sit back on his haunches, while she used that ever so seductive voice, "Ladies please meet my slave boy. Here is available for anything you wish to use him for, he has no limits, although he thinks he does!"

As Kevin got into the required position, he heard his Mistress's evil laughter louder than ever, and then he saw the two women looking directly at him, grinning like they had just won the lottery. After a few seconds, he realized the women were Laura, the HR director and Claudia, her secretary from work!! He immediately tried to return to a face toward the floor position but a sharp yank on his leash and slash across his ass with the riding crop quickly convinced him that was a stupid idea.

"Now slave, I want you meet your two new mistresses...that's right I have convinced them both to assist me with your further training. As I cannot really tell what you get up to during the week, they have so graciously agreed to help keep you in line while you are at work!"

Kevin had this rapidly rising feel of absolute dread taking over his rational thinking...how could she do this to him, he always had a hard limit against anyone else finding out about his submissiveness. And two women from where he works was even worse! As he looked back toward his co-workers he saw the most evil of smiles coming from them both and again his mind started to race out of control with fear.

"Look at him ladies; I think he is scared silly right now! See how red his face is! Are you feeling humiliated slave?" taunted Mistress Ruth.

Although he wanted to scream out that of course he was, he knew that the question was rhetorical and since he was so effectively silenced with the 3 inch cock gag, he just knelt there in total humiliation. He hardly heard the women as they chatted, with his Mistress explaining some of the training he had been subjected to over the last six months and how she had promised him a special treat for his six month anniversary.

So engrossed in his own thoughts and fears, he missed the demand to rise to a standing position. So Mistress Ruth explained, "When he fails to stand it is really easy both punish him and get him into the required standing position." So saying and before it could register in his slave brain, she quickly reached down and grabbed his balls, squeezing hard and yanked him upright.

"There that is better, slave. You always respond so quickly to a little ball pain!" remarked Mistress Ruth as she laughed as how he winced and tried to object, silenced of course by the gag. "Notice how effective that gag is, I do get tired sometimes of listening to him cries, his begging for mercy, and his pleas to stop. I have several gags for him, but this one holds a nice 3 inch long cock in his mouth. So not only does it keep him quiet, it helps get him used to having cock in his mouth!"

"Now turn around I want the ladies to see your nice red ass with the lovely cane marks I put there earlier", demanded Mistress Ruth. "Feel free to touch him however you want and don't worry about being gentle!" laughed his sadistic Mistress.

Both Laura and Claudia took full advantage of her offer and spent the next 20 minutes feeling him all over, slapping at his ass, pinching his nipples. Squeezing his balls, and generally adding to his total humiliation. Then Claudia asked about the plug in his bottom hole.

"Yes dear, I often make him wear a plug in his bottom hole as you call it, although I usually refer to it as his fuckhole! After all that is one of the two holes he has that gets violated often with one of my strap-ons. The plugs remind him of his lowly status as a slave that exists just for the pleasure of his Mistress. The one he has in today is the largest he has had to wear so far, but I wanted to get him stretched out a little for the huge strap-on he will have to endure later. I plan to totally break him this weekend and I am so glad you agreed to help me take to his next level of servitude!"

All this was said just as the slave was gaining control of his emotions. The sinking feeling of despair once again started to overtake him. Just the thought of being made to endure the huge strap-on fucking she planned was bad enough; it seems she was going to have spectators for the event. How was he ever going to be able to face these people at work again? And then he realized what Mistress Ruth had spoken about earlier, having them help her keep him under control at work? He felt a sudden urge to have to empty his bladder!

Claudia was feeling his balls and commented that they rather full, like he had not emptied them for a week or two. Then she started squeezing them and pulling down on them eliciting groans of agony through his gagged mouth, which seemed to please her to no end. This of course just enticed her to do it some more. "How often does he get to cum, Ruth?"

With a huge grin, Ruth answered, "He doesn't! Not once since he became my weekend slave, so that is six months of cum stored up in those slave balls!"

"Oh my God" exclaimed Claudia, "I had no idea a man could go that long with no release. You must so damn horny, Kevin. But I see your Mistress keeps you locked so there is no change of you misbehaving!"

"This chastity device is brand new; I just locked it on him today. Although he has been locked since the very first day he served, this one is special" said Ruth while flashing that evil smile of hers, "The inside is lined with sharp spikes about an eighth on an inch long. There are probably 60 or more of them that cover the whole inside of the tube. It is a little uncomfortable unless of course the silly boy tries to get an erection...then you can only imagine what happens to his useless slave cock!!"

"I am impressed," extoled Laura. "I wonder if we can make him get an erection."

"Well you know what all men love to see don't you, ladies?" inquired Ruth.

Laura and Claudia looked at each other and then at slave Kevin. Then without any words between them, they began removing some of their clothing until they were both down to just garters, panties and stockings. As the slave stared at them, the hoped for reaction started, and he soon had the look of pain on his face as his cock once again betrayed and tried to get erect.

"Oh my, look how easy that was," remarked Laura. Claudia replied, "I know just how to get him even harder." She then leaned forward and took one of Laura's breasts into her mouth and started sucking and licking the nipple. It was obvious that both were enjoying themselves based on the moans from Laura and the look in Claudia's eyes.

"Claudia, you seem to be quite talented with your mouth, dear. I take you and Laura have done this before?" queried Ruth.

"Oh yes, many times. We enjoy woman on woman lovemaking much more than with men, although we both still enjoy a good hard cock on occasion." With that Claudia went back to sucking on both of Laura's generous breast, again enticing the slave's cock to do what was only natural.

"Well slave boy has had six months of oral training in the ways to please a woman. And if I must say so myself, he does an excellent job getting me with his tongue. In fact it is the only way he gets to service my pussy!" said a smiling Ruth. "I think it's time for some more humiliation of the slave. After all he is here for our entertainment!"

Mistress Ruth then surprised the slave by removing his gag. "Well now slave why don't you tell them how many times you have sunk your cock into my hot pussy. They know you haven't cum, but how many times have I edged with my pussy"

"I have never had the privilege of putting my cock into your hot pussy, Mistress," was his very quiet response.

Laura broke out in loud laughter and Claudia was giggling like a teenager at this revelation. "Well for heaven's sake, "said Laura, "what do you do when she needs to be fucked good and hard? Every woman needs it sometime!"

Kevin tried several times to answer, but he stumbled over the words so badly that finally his Mistress saved him the trouble. "I have a nice gag that has a 10 inch dildo mounted to it and I ride his face as hard and for as long as I wish. He gets a real close up view of me getting fucked, but none of the pleasure!"

"But what I love most" continued Ruth "is using a strap-on on his fuckhole and riding him until I have an orgasm from the dildo on the harness that fits into my pussy. In fact tonight he is going to take a strap-on much larger than any that he has been fucked with before. I'll be right back!"

While Ruth was out of the room, Laura started questioning the nervous slave boy. "So you have never even put your cock in her pussy, she fucks you in the ass like a sissy, she keeps your cock locked up, and has never let you cum even once. She obviously canes, straps, whips and spanks your ass whenever she feels like it. What else does she make you endure?"

"She makes me sleep in bondage when I am here, usually on the floor next to her bed. And she, she uses, she uses me however she wants, even making me drink down her pee" mumbled the humiliated slave.

Both Laura and Claudia broke into uncontrollable laughter at these revelations. They both poked more fun at him for how he lives his life in his Mistress's presence. And they both hinted to him that they had plans for him as well, which again brought rising fear to the forefront of his mind. But before he had much time to dwell on it, he looked up to see Mistress Ruth stroll back into the room, totally naked save for her high heels, and a strap-on around her waist. At second glance he realized that this was really a long, thick strap-on.

Ruth explained, "I told him that today I would be fucking him with a much larger dildo and the time has arrived. This is a full 12" in length and 2" in diameter. The biggest he has had before is only an inch thick and 7" long. So this should be quite a treat for him! I know you will squeal, cry, beg, and sob slave because I will be rough with this dildo, but rest assured I will not fail to drive the entire thing up your fuckhole and then pound you until I cum. There is a lovely 6 inch dildo buried in my divine pussy, you know, the one you have NEVER had the privilege of fucking!" The slave cringed as he heard her loud laughter and saw the looks of delight on her friend's faces.

"Now get up on the table slave, on your back with your ass right at edge. I want to be able to see your face when I forcefully fuck you with this lovely strap-on. Claudia can you please put a pillow under his ass so it is at the right angle for me to penetrate?" asked Ruth.

As Claudia shoved the pillow into place, Ruth unhooked the chain between his ankles, and then ran a rope under the table and secured both wrists to it and cinched it tight, causing his arms to be down at the side of the table.

"Laura and Claudia, would each of please grab one of his ankles and spread him wide, please. Pull his legs back so his knees are back by his head. Now look at me slave, I want to see the terror on your face as break you but good!"

As his Mistress pushed the huge dildo against his tight little opening, he could smell the arousal of Claudia and Laura as they stood on each side of him. His fear was increasing as realized how much they were enjoying this and wondered how much of this new dildo he could actually take.

Part 4

"I can't fuck you with this slave," purred his Mistress.

Hearing this, the slave boy visibly relaxed. Both Claudia and Laura looked at Ruth just knowing she would not let the boy off this easy. "You see I forgot to remove the nice plug in your fuckhole that you have had in for several hours now, just getting your hole ready for the ass raping it is going to get!" The three ladies all burst into hearty laughter as they watched the slave go from looking relaxed to being terrified in just a few seconds.