On Her Terms Ch. 03: The Descent

To say Dale was confused by his new lifestyle arrangement would be an understatement. Over the past few weeks, his entire life had been turned upside down in a series of events that had escalated faster than he could even adjust to. And that was exactly the way Sam wanted it.

Sam was Dale's ex-girlfriend's lesbian lover. And now Dale's Mistress. Or should it be "Master"? Dale wasn't even sure of that little detail. Over the past few weeks Sam had manipulated Dale into becoming her personal sex slave by using Dale's ex-girlfriend Laura as bait. And even though Dale knew he was being manipulated, and had been able to watch his own descent into depravity, he was powerless to stop it. In fact, he was enjoying being used, and deep down he even looked forward with anticipation to submitting further and further to Sam.

In return for his submission, Dale was occasionally allowed to have sex with Laura, although never as frequently as he had hoped. But it wasn't just that reward that kept him coming back to Sam. He was also extremely attracted to Sam. Sam was short and curvy, but extremely athletic, with thick strong legs and buttocks, a thin waist, and large pert breasts. Dale enjoyed being made to worship her magnificent body. He was a natural submissive, and took intrinsic pleasure in serving Sam and Laura.

After their first session, Dale returned to the girls' apartment on an almost daily basis to serve Sam. The very next night was an example of a typical night:

Dale arrived around 7:00 in the evening. He had been instructed to walk to Sam's apartment, about a half mile from his own. Sam answered the door wearing tight work-out shorts and a sports bra. "Well, well, I wasn't sure you would actually come," said Sam teasingly. "I guess you like being my bitch, don't you?"

Dale flushed and looked at the floor sheepishly. Sam lifted his chin with her finger and looked Dale in the eye. "Well," she asked, "Did you enjoy being my bitch last night?"

"Yes, sir," answered Dale, quietly. He looked around self-conscious of the fact that they were still standing in the front doorway of Sam's duplex.

"Yes what, bitch?" demanded Sam loudly. "Are you going to be my slutty bitch again? I want to hear you say it."

Dale swallowed his pride and gave in. "Yes, sir! I want to be your bitch!"

Sam laughed and ordered him inside, slapping him hard on the ass as he passed her. She ordered him to strip naked as soon as she closed the door.

Dale looked around, wondering if Laura was home. He didn't know whether to be disappointed or relieved when he didn't see her. He slowly began to undress. "If you don't move faster, then next time I'm going to make you strip outside on the porch," said Sam. Dale picked up the pace, removing his boxers and handing his pile of clothes to Sam. She turned and walked down the hall, tossing the clothes in the bedroom and locking it behind her. "You'll get your clothes back when I'm done with you, slut," she said to Dale. "Now get over here and get on your knees."

Dale spent the evening massaging Sam's feet and sucking on her toes, licking her to several orgasms, kissing and licking her ass, and fellating a medium sized pink strap-on dildo. Dale was thankful she didn't use the dildo to fuck his ass that night, since it was still sore from the night before. But, she did finger his ass and insert a medium sized butt plug. She teased him when his cock began to get hard as she fingered him, and made him admit he liked it.

As he sucked her silicone cock, giving it head as if it were real, Sam humiliated him about his own cock which was still hard, and which was slightly smaller than the dildo. "I can see you like sucking cock, don't you slut?" she teased. "You're a natural at it. If you keep practicing, maybe you'll get to suck a real cock someday. Do you want me to find you a real cock to suck, slut?"

"No, Sir," he said looking up at her in alarm.

She laughed down at him. "Oh, you're just being shy. When I get through with you, I'll have you begging to suck cock. Now keep practicing on mine!" Dale went back to work, worried what she had in store for him.

Dale never did see Laura that night. She was at work the whole time. At the end of the night, Sam pulled the plug out of his ass and replaced it with a slightly bigger ball-shaped one. Then she gave him back his clothes, except instead of his boxers she gave him a pair of pink satin panties. Humiliated, Dale put them on and dressed. He soon realized why she wanted him to walk over. The entire way home he felt the satin fabric swishing across his butt cheeks and he felt the plug moving inside his ass. The sensations gave him a hard-on which lasted the whole walk home. When he got home, he immediately began jerking himself off, leaving the plug in until after he had finished.

The next night he was instructed to put the plug back in his ass before walking over again. The large plug was difficult to get in when his ass was not already loosened from the smaller one. He walked over to Sam's apartment feeling the plug moving inside of him the whole time. When he got there and undressed, his hard-on was plain to see and Sam laughed and teased him, calling him a slut. Since he had not been given instructions on what to wear, he had just dressed in his normal clothes with boxers on. Sam said nothing about this, but again sent him home in a pair of panties, and the same plug. After a few nights of having his boxers confiscated and replaced with panties, Dale decided to wear panties on his way to Sam's house. When Sam saw this she laughed and walked over to pat his satin covered ass. "Wow, Dale," she said. "You wore panties without being told to. You are officially a true sissy slut now. I knew you were a sissy deep down, you just needed me to bring it out." She smiled a wicked smile and laughed as his cock grew from her taunting.

Most of their sessions together were the same. He would give her a massage or a foot rub. She would often make him suck on one of her dildos. He would often eat her out. He always had to kiss or eat her ass, sometimes for long periods of time. Sometimes Laura was there and he was ordered to massage her, and eat her out or worship her ass, too. These he did gladly. Although at first he hated being humiliated and used like a slut in front of her, eventually the discomfort wore off. Besides, Laura seemed to get off on watching Sam bend him over or make him beg. Sam would often fuck Dale with one of her strap-ons, especially if she wanted to humiliate him in front of Laura. When she wanted to punish him for something, then she would use one of the bigger ones, stretching his ass wide open. Getting fucked in the ass became easier over time and he began to enjoy it in spite of himself. Sam laughed and taunted him endlessly the first time he came on the floor just from having his ass fucked. Sometimes she made it her goal to make him cum just from pegging him, so she could humiliate him some more.

After a couple of weeks, they had settled into a routine. By this time, almost all of Dale's reluctance was gone and he was really embracing his role as a slut, eagerly accepting whatever Sam had in store. Inwardly, Sam was pleased, but she wanted to see how far she could get him to go.

At first, he got to have sex with Laura about once or twice a week, always being made to clean her up with his mouth afterwards. But more often, Sam would fuck Laura right in front of Dale, leaving him blue balled. Sam teased him for being a cuckold. Dale had to watch on many occasions as Sam made love to Laura's ass, although he was never allowed to. Laura genuinely loved, even craved, anal sex, often begging Sam to let Dale fuck her ass. But Sam insisted that Laura's ass belonged to her alone. As a compromise, Sam went out and found the most realistic feeling dildo she could find. It was a little bigger than Dale's dick of course. She would shove it up Dale's ass and make him keep it there until it was warm like a real cock, and then she would use it on Laura. That seemed to satisfy Laura for the most part, and Dale resigned himself to the fact that he would never get to experience Laura's ass again.

One day, Dale came over and stripped down naked as usual. He was surprised to see Sam dressed only in a thong as she came out from the bedroom. The tight thong accentuated her short hourglass figure. His cock sprang to attention immediately. Sam walked over to him, smirking mischievously. She stopped in front of him and tugged on his erection. "Well, it looks like someone's happy to see me," she said. "What is it with you boys, you just can't learn to control these things. I guess I'll have to control it for you." With that she turned on her heel, and waved her hand beckoning Dale to follow her. "Come," she ordered, and began walking toward the bedroom. Dale followed with his eyes glued to her magnificent, round, firm ass, which was swaying from side to side as she walked. His cock only became harder and twitched as he imagined his face buried between her cheeks.

She led him into the bedroom where the chair from Laura's vanity was pulled out into the center of the room. She ordered Dale to sit. She then cuffed his hands to the back of the chair. This was new, thought Dale, wondering where this was going. Sam walked into the bathroom and Dale heard some water splashing in the sink. Same came back in holding a towel which was dripping with water. She held the towel over Dale's lap and let it drip onto his crotch for a few seconds. Dale cringed in shock as the drips of ice cold water hit his skin. Sam ginned wickedly and dropped the towel onto Dale's raging hard-on. Dale sucked in a breath and yelped as the ice cold towel covered his lap. The cold immediately caused his erection to deflate and shrink down to nothing. Sam pulled the towel off and took a look. "That's more like it," she said. Then she produced a plastic cock cage, slipped it over Dale's flaccid member, and clicked the lock into place. She sat back and admired her handiwork, and the look of shock on Dale's face.

"That ought to keep your worthless little dick from getting in the way all the time, now," said Sam. "And you better get used to it because you're going to be wearing it anytime you're here, from now on." Dale's cock was already trying to get hard, straining against the cage as Sam began uncuffing his hands. He reached down to touch the cage, turning it back and forth. When he looked back up, Sam was strapping on one of her larger dildos. "Now let's see who cums when I fuck your slutty ass."

She ordered Dale onto the bed and proceeded to fuck his ass with renewed enthusiasm. She rode herself to two good orgasms while Dale's own dick was frustrated by the cage. He still felt the same pleasure he had come to enjoy from his ass being stretched and his prostate being stimulated but with his dick locked up he was unable to orgasm. Now he was truly just Sam's fuck toy.

Over the rest of the night Sam found Dale had extra enthusiasm when eating her out or massaging her legs and ass, and even while fellating one of her many silicone cocks. His constant arousal and frustration made him an extra attentive slave. Sam knew she was going to like this change. At the end of the night, she stuffed his ass with the biggest plug she had used on him yet. She unlocked his cock cage and gave him a pair of tight satin panties that she knew would drive him crazy the whole walk home. She orderd him to leave the plug in when he jerked off that night. And he did, almost as soon as he got in the door. He jerked off three times that night, working out all of the pent up frustration.

From then on, Sam put the cock cage on him every time he came over. Like everything else, Dale got used to it relatively quickly. In fact, Dale had never been more aroused in his life than when his dick was locked in the cage and he was made to serve Sam and Laura. Laura seemed to get a kick out of it, too, and enjoyed teasing him whenever she could. His heightened arousal and frustration, made his orgasms even more intense when he was allowed to have sex with Laura. And Dale was just incredibly turned on by Sam having control over his orgasms. Everything about this new twist made him even more addicted to Sam and made him more willing to be her total slut. So of course, it wasn't long before the first time Sam sent him home at the end of the night with his cock still locked in the cage.

Dale had a hard time sleeping that night due to his persistent arousal and frustration. Luckily the next day was Sunday and he didn't have to work that day. Of course, he wasn't really able to get anything done around the house either. He didn't know how he was going to last the whole day. Then, he got a text from Sam around 1:00 in the afternoon: "How you holding up, sissy?"

Dale texted back: "Having a rough time. Can't focus on anything."

"You can come over here. I'll give you something to focus on."

Dale practically ran over to Sam and Laura's apartment. Sam laughed to see his eager face as he obediently stripped off his clothing. "What are you so excited about, slut? I didn't say I was going to unlock you. I just offered to put you to work. You're going the help me do chores today." She patted him on the ass and grinned at him, reveling in the power she had over him. Dale didn't care what she asked him to do. Somehow, he felt better just being there, serving her. "Boys are so pathertic," she sighed.

She led him into the kitchen and put him to work doing the dishes. She found a short flowery apron for him to wear, and teased him, calling him a sissy and saying it looked natural on him. It turned him on when she taunted him like that. While he was bent over the sink scrubbing a pot, she came up behind him and began rubbing his ass sensuously. He immediately began pushing his ass back against her, craving more. Sam just giggled. She reached down and slowly pulled the large plug from his ass. He grunted as the widest part slipped free. She set it down on the counter and easily slid three fingers into his gaping hole. "You're so loose!" she said. "You're such a little slut aren't you? You'll take anything up your ass, huh?"

"Yes, sir. I'm your little slut."

"Well, maybe I'll find a real cock to fill your slutty ass. Would you like to feel a real cock in your ass, slut?" Sam ask tauntingly.

"No, sir. I just want your cock in my ass."

"Well, I think a slut like you needs a real cock in your ass, to show you what a slut you really are. And since your ass belongs to me, I'll do whatever I want with it. And right now, I've got a new toy I want to try out. Bend over!"

Dale bent farther over the sink and spread his legs. Sam produced a medium sized plug which split and flared open at the tip. She squeezed the tips together and pressed it against his opening. It slipped easily into his well-trained hole. Once inside of him the tip flared open, stretching his anal walls and pressing against his prostate. The sensation was different than a typical plug, making him feel fuller than ever. And the flared end assured that it would stay snug no matter how much he walked around the house. "Does that feel good, little slut? Does that make your ass feel full?" she asked.

"Yes, sir!" Dale grunted.

"Good. And that's just the medium size. Over time I'll work you up to the extra-large," she said giving him a wicked smile. Dale just looked stunned. His ass felt so full! He couldn't imagine what an extra-large version would feel like.

"This toy has another nice feature," said Sam looking pleased with herself. She pulled out a small remote control and pushed a button. The plug in his ass began vibrating, creating an intense sensation. "This," said Sam proudly, "is my call button. When I turn this on you will come find me at once, understood?"

"Yes, sir," moaned Dale, his grip tight on the edge of the sink. Sam pushed the button again and the vibrating stopped.

"Now, hurry up and finish those dishes," said Sam as she turned and walked away. "I've got a whole list waiting for you."

Dale went back to work on the dishes, trying to ignore his throbbing dick which was straining against its cage. As he worked, he could hear Sam exercising in the other room. He was just about finished drying the dishes and putting them away when his ass suddenly started vibrating again. The sensation shocked him so much he almost dropped a plate on the floor. He set the plate down and walked into the living room. Sam was still wearing a thong on her bottom half, though she had donned a sports bra to contain her voluminous breasts as she worked out. She had two large hand weights and was doing a series of motions squatting, lunging, and raising her arms over her head, then repeating. Dale stopped in his tracks as he walked through the door to see her bent over with her strong legs and gorgeous ass rippling as she moved. The sight, combined with the vibrating in his ass, was almost enough to make him cry with frustration. Sam saw him in the doorway, but let him watch her through another couple sets before acknowledging him.

"Are you done with the dishes yet?" she panted in between breaths.

"Uh, almost, Sir." Dale's eyes were still glued to her delicious ass.

"Good," panted Sam. "I want you to sweep the kitchen and then start vacuuming the rest of the house."

"Yes, sir," said Dale, staring impotently.

Finally, Sam stopped and picked up the remote to turn off Dale's vibrating plug. He snapped back to reality when Sam's body and the vibrations both stopped.

"Well?" Sam said, impatiently. "Get to work, unless you want your dick to stay locked up tonight, too!" Dale scurried back to the kitchen to comply.

He worked with renewed energy, with the image of Sam's body stuck in his mind. Each time he moved through the living room to vacuum a different part of the house, he would slow down to admire her. Sam knew exactly what effect she was having on Dale in his frustrated state. She waited until she heard him turn off the vacuum after finishing the last room, then she hit the remote again. Dale hurried back into the living room. Sam motioned him over and instructed him to kneel in front of her. He looked up at her to see her breathing heavy from her workout, her body glistening with sweat from head to toe. She slid her thong off and stepped out of it, turning around with her legs spread, presenting her ass to Dale. Dale knew what was expected and eagerly buried his face between her sweaty cheeks and began lapping at her ass. He felt so deliciously dirty and depraved. Sam was impressed with the way he so willingly degraded himself for her. When he had licked her entire ass clean, she sat on the couch and presented her sweaty feet for his attention. As he began to suck her toes without any verbal command, she smiled, knowing she had complete and total control over him now. There was just one final boundary to push him across.

Later that night, when Laura came home from work, Sam rewarded Dale for his faithful servitude. She took the cage off so he could have sex with Laura. He ate Laura out to get her ready. Then right after he plunged his dick into her warm, waiting slit, Sam pushed the button and Dale's plug buzzed to life again. The sensation was so intense, and Dale had been so frustrated, he only lasted a few short strokes before blowing his load in a toe-curling orgasm. Although it felt good to him, it was not nearly long enough to get Laura off. Sam pushed him aside and stepped up with a large dildo strapped between her legs. Dale could only watch as Sam brought Laura to multiple orgasms. Meanwhile, the buzzing plug pressing against his prostate brought his erection quickly back to life. When they were done, he sucked them both clean. Then Sam brought out the cold, wet towel again to shrink his member back down so she could put the cage back on him again. She teased him and admonished him for cumming so soon. Then she sent him home, frustrated all over again, though not as bad as before.