u/Silent-Society483

Ian thrashed against his naked body against restraints trying to figure a way out of his problem. On her knees right in front of him was his stepmother Allison, masterfully stroking his cock.

It was all moving so quickly. Just a week ago he was in a normal relationship for her and then he stumbled onto that damn chastity cage. His curiosity cursed him to a week of denial where he had edged himself enough into thinking that submitting to her games was the smart play.

He naively thought that somehow all his lewd fantasies that he had shamefully stroked himself to were going to be filled right away if he just pulled along. Now no matter what choice he made, he was going back in that damn prison that had put him in this place.

"Please...please just let me cum"

The masterfully skilled hands slowed down allowing some of his brain function to return so he didn't focus everything on what was going on between his legs. "You get to cum right now baby, unless you don't want to..."

"I don't want to go back in the cage. I just want to cum."

"Aww baby, it's too late for that. Look at where you put yourself. Don't you like your step mommy stroking your cock?" Her cadence picked up slightly.

"Yesss" He hissed, trying to thrust his hips to get more traction but with no success. The more he thrusted the less pressure she applied with her fingers.

"Well, you can enjoy that and so much more. However, if you want to spend as little time in the cage as possible then you really have two options. The first is that ruined orgasm. I will stroke you right up until you can't stop from cumming and then-" She let go of his cock.

"I watch all your cum drip out and you have a ruined orgasm." He whimpered and kept trying to thrust his hips for traction.

"The other option is you beg me to lock you back up and then next week you get this"

Ian thought he got good head some of his prior girlfriends, but what Allison instantly erased that fiction. With no hesitation she slipped his cock into her mouth and sank effortlessly down his well-endowed member until the entire thing disappeared in her mouth. She then equally as casually withdrew, letting the tip slip from her lips with an audible pop. "You get that."

Her hands gently cupped his balls and began to gently massage them, keeping him nice and primed. "it's up to you baby, now make your choice before I do."

A moment was given to allow his internal debate, but it did not last long before she began to stroke him once more. With one final application of lube it became clear this was the final few seconds he was going to have.

Ian writhed and moaned, his cock throbbed and protested in her hands Equally desperate to spill his load as fill her mouth once more. He simply could not get it back out of his head.

"Please...." He pleaded. She offered no mercy or reply and continued stroking him.

He closed his eyes and shivered, trying to come to terms with what he knew he really wanted. "Please - Please lock me back up."

No sooner did the words leave his mouth then all the friction on his cock. His body did its best to try and cum despite what he asked but all he managed to do was pathetically thrust and bob into open air.

Before he could recover though he felt Allisons lips smash into his with mixture of passion and lust. Her tongue dover into his mouth and he welcomed it. He tried to move his arms to embrace her, fuck her, he didn't know anymore but they remained bound at his side.

"I knew you were special. Good boys get rewards from mommy. But let's get you locked back up first like you want me too."

Before he could conjure protest she was out of the room, only to return with a damp cloth a moment later. She wiped him down and then slowly compressed the cage back into his cock with a satisfying click.

"Now for your reward" She went over to the closet and retrieved a blindfold and a very life like dildo that was not dissimilar to his own size. She took away his sight and then shortly after she heard the rummaging of clothing being peeled away.

She leaned her body up against him. Her large breasts with erect nipples pressing into his chest as she seductively cast into his ear "You have not earned the right to see me naked, but what you just did for me was so hot I just need a good fucking. I hope you don't mind as I make myself cum a few times."

A firm hand grabbed hold of his encased cock "Be quiet and enjoy the sounds I am about to make. I will leave your imagination to fill in the gaps."

Sounds a vibrator took over and then he began to hear heavier breathing. The reality of the situation of knowing his stepmom was masturbating right Infront of him, looking at him was torture.

His hips tried to roll and thrust as if he wasn't locked in place, as if his cock wasn't locked in a painfully tight prison, as if he could fuck her.

The more he struggled, the, closer Allison seemed to get. Soon he heard verbal cries of pleasure that he knew to be the sound of her receiving her first orgasm. 3 more soon followed, each louder and more intense sounding then the last before finally the vibrator went silent.

"Mmm, that is just what I needed. You make a great visual tied up and desperate like that."

"For the next week, I do not want you pestering me with your needs. If you beg me for release I will just postpone it as much as I deem fit."

He felt one of hands being freed up and then heard her walk away. It took him longer than he cared to admit but eventually he freed himself from the device and went to his room. He collapsed down onto his bed and the totally of the night took hold and he quickly fell into a deep slumber.

He didn't need an alarm clock to wake him up the next morning. A dull ache between his legs rose him from his morning slumber. It took him a moment to process why the sensation was only for the prior night to leak back into his memory. He let out a soft tired and sexually frustrated grown as his denied erection attempted to rub itself against the soft sheets. All he managed to do after a few minutes was leave a wet spot on the bed but no closer to orgasm.

Allison paid him no mind like nothing had ever happened. He wanted to pester her with a million questions, but she seemed not remotely interested in talking about. Not wanting to push his luck he resigned himself cleaning up things around the house, often at her request.

As he lay in the bed tossing and turning at the end of the day though he masochistically activated the remote teasing functions on his cage and edged himself twice to an orgasm before giving up and trying to catch some weak sleep. He swore he woke up late in the night, hearing the quiet hum of a vibrator from the shared wall.

The next day however things picked up speed. She called him over to the living room where she was relaxing on the couch with a glass of wine in one hand and her phone in the other.

"Take a seat on the ground" She gestured the ground in front of him.

"I have been busy on my feet all day and I could use a nice long relaxing foot rub. Are you interested?"

"Yes" He quickly responded. Eager for any opportunity to get his hands on her.

As he began to work on her feet, she let out a little sigh. "I could get used to this."

A few taps later on his phone his cage began a very subtle vibration causing him to jump a little in surprise and look at her. He had forgotten she could do that. "Do you not like it when I do that?"

His cheeks flushed with a bit of color, and he quietly whispered, "I like it."

"Tell me, what do you like."

His face turned crimson. forcing him to build up courage before answering. "I like it when you make the cage vibrate."

"You like it when your step mommy plays with your cock?"

The mixture of shame and lust left his stomach in knots. Unable to say yes, he vigorously nodded and tried to keep his focus on her feet.

The foot rub lasted a total of 30 minutes before she eventually turned off the vibrations on his prison and casting him off to leave her alone for the rest of the evening before calling it a night early on and retreating back to her room.

The next two days featured no activity much to the mercy and torment Ian. She seemed impossibly capable of turning her sexuality on and off at the drop of a hate much to his frustration. At least that was the act she kept up with him.

On the fourth day she came roaring back onto her desire, perhaps unable to hold it back.

No sooner then he came down for breakfast then she beckoned him over. "Have you been enjoying yourself so far this week?"

"it's been very hard, but I have been really enjoying it."

She placed her hands on his hips and leaned in giving him a kiss. "Good."

"You have no idea the things I have been thinking about doing to you...the things I will do to you if we continue after the end of this week." His heart fluttered at the words and his cock filled up every millimeter of space it was provided.

She leaned in and kissed him again. This time her hands slipped forward and undid his pants. Seconds later his cock as free and in her hands. As their lips parted, he looked down and watched the cruel lust cement itself upon her lips. "It looks like you are excited for what may come as well. However..."

She released his cock leaving it bobbing in the open air between them. "Today is chore day."

"You are to clean the kitchen, bathrooms and the living room today. I want them spotless. Also, I want you naked while you do it. Take it all off."

He stripped down to the already exposed cage, leaving her to drink him in from head to toe like a tasty snack.

She fought back the urge to praise his magnificent body and just jump him right then. Her cunt ached to be serviced but she stuffed the urge back down knowing she had to break him in proper. Unlike his father which was given free rein to be a selfish lover just like so many men before him. He was going to make up for each and every single one. He had no idea the things she had planned for him.

"Get to work unless you want to be at it all day." A quick and playful swat on his exposed butt cheeks send him on his path. This power was intoxicating and the thing she craved above all else was more of it. His suffering would be legendary if it was going to satiate her appetite.

Ian stood at the bridge between his bedroom and the spare. His cheeks still flush as he felt the eyes of his stepmother burning a hole in the back of his head, awaiting his choice.

A week ago, he had accidentally stumbled onto a smart chastity cage. What had started as a curious sexual exploration, turned into a week of self-torment.

Unknown to him, when he placed the device on it was still connected to his stepmothers' phone. He had tried to seize back control of the device assuming no one was on the other end, it was a weeklong process. During it he both edged and teased his cock in that tight prison. It left him hornier than he had ever been in his life.

Now at the cusp of his much-awaited freedom, his world had been turned upside down. Allison knew the entire time that his cock was in the cage. It was embarrassing but also incredibly arousing. To pour fuel onto his sexual fire, she had given him an offer. To put an end to this embarrassing situation between them so they never had to speak about it again or he could step blindly into the rabbit hole.

On one side lay the road to certain freedom. A return to normal. He had never been into tease and denial kink before this and had always been the traditional role in a sexual relationship. He was young and his libido was high. His cock yearned for freedom. It yearned for release. To be able to penetrate something solely for its own pleasure.

As he thought about all of the holes that he wanted to fuck though, his mind flashed to Allison. That plunging neckline was forever burned into his brain already. He would never have admitted it to a soul but he certain had fantasized about her before. She was an absolutely smoking body for her mid 30's that any man would have been eager to call his.

The week of denial caused his brain to rot and spoil as it circled the drain thinking about her more and more with his cock driving all of the thoughts. This was going to be his only shot to live out all of those fantasies he had racked up over the years he had known her.

His cheeks stayed flush with an even mixture of embarrassment and arousal, but his mind was made up. He turned and walked into the spare bedroom. He didn't have the confidence to look back at Allison but if he had, he would have seen her grinning like a cheshire cat.

The wait in the spare bedroom was brutal. His heart was racing and it seemed to never end. He felt like a virgin awaiting his first time. Eventually Allison sauntered in very casually with a happy but not over eager smile upon her lips. "I thought so."

Facing his choice caused Ian's heart to race in his chest, his mouth felt dry and for the first time in a long time he didn't seem to know what to do next. That didn't stop his groin though from aching with desire. Words failed to escape his lips as he didn't know what step to make next.

"Let's get to know each other and our...interests a little bit more. Why don't you go and sit on the bed" Allison instructed him.

He sat down at the edge of the bed. She approached and stood in front of him now positioned higher despite her short stature. "Good boy." The words caught him off guard and zapped right through him like lightning.

"Now, is this your first time you have locked yourself up?"

Ian's stammered out a yes trying to avoid eye contact.

"Oh, I love a good chastity virgin. I bet for a young man like yourself it must have been torment to last a week. I still couldn't imagine waiting that long myself" She teased him playfully.

His eyes shot up and looked at her imagining her pleasuring himself. His cock pulsed with his heartbeat as he drank in the images in his mind. I

"Have you enjoyed your time in your Cage? It seems like you have both edged and teased yourself quite a bit in it.

"I-I was trying to be able to orgasm with it on." It was a lie he told not only to her.

"Of course, I bet you were quite desperate" She smirked knowingly. "Are you familiar with any of other devices in here?" She gestured to the various odd looking furniture bits.

A quick look around before their eyes locked once more. He shook his head. "No."

"Would you like to get to know one of them more?"

As he looked up to meet the question for the first time he could see the hunger on her face, for him. The question didn't matter at that point. It could have been anything; the answer could only be one thing. "Yes"

She hooked her finger and gestured him to follow. She walked over to what looked like a pole sticking up from a platform with various mounting points along its length. The pole ran almost all the way up to the ceiling. "I think you are really going to like this one. You will probably want to take your shirt off though."

He did not need to be told twice and quickly stripped his top off. She drank him in from top to bottom and then nodded approvingly. "Now wait here while I get the rest of the pieces we will need."

She went over to the closet and rummaged for a moment before returning with what looks like a few kinds of restraints and a bar. "Now I am going to restrain you in this device so we can have some more fun, okay?" It was a question in name only.

"Now place your back towards the pole and let me get you ready, you are really going to love this" She guided him into position and then moved in close as she set up the device, her clothed breasts pressing firmly against his chest as she set him up with surprising efficiency.

Soon he found himself with his locked at his waist with a strap keeping him from thrusting his hips. Higher up a collar had been attached around his neck. Both groups of items locking him firmly to the pole.

Allison took a step back and admired her work. "I think that will do, for this time. Now let's see how hot you would like to turn things up."

She positioned herself directly in front of him and sank down onto her knees, drawing her hair up into a pony trail. "I bet you have envisioned me down on my knees in front of you before, haven't you?"

The forwardness of her sexual energy was still hard for him to process "A-a few times."

A smirk crossed her lips "Good, I like honesty. I reward it often. She reached up to his pants and began to undo them. "You can tell me to stop any time you want."

Hell would sooner freeze over then he told her to stop and soon his cage cocked popped free of his pants and into view, throbbing in its prison. Her hands shifted down and began to gently tease his thighs "Oh look at you! Even in that very tight prison I can tell you are quite gifted and those balls look so large and plump. I bet they would love for me to empty them right now. Do you want me to free MY poor prisoner?"

His cock answered before he did and twitched in front of her causing her to let out a little giggle. "Yes, it's been so long."

"Yes what?"

"....Please unlock my cock Allison"

Her face contorted as she mulled something over. "You are new after all, you will learn yet" She quietly said to herself

Allison pulled out her phone and used the app to unlock the device. She pulled the cage off but left the base ring on. It only took seconds and quickly his young, virile and impressive cocked swelled up to full strength.

"Oh, it's so much nicer than I even I hoped. I am going to enjoy that!" she squealed joyfully. She applied a generous amount of lube and began to gently rub it all over his cock and balls.

Soon he was throbbing in her hands, a long week had made him a quick shot, but he didn't care. As he began to get close though, suddenly her hands vanished, leaving his cock bobbing in the air and leaking precum down onto the floor.

"What, no! Don't stop!" He exclaimed exasperated.

She grabbed him firmly but not painfully by his full balls, sending a clear message on authority and causing him to quiet down. "Bad boy, you don't tell me what to do. I tell you. Understand?" He quickly nodded in agreement, and she released his heavy sack.

"Now I am still upset about you stealing my sex toy and if you and are going to start exploring me together you are going to have to learn that you have to make very hard choices and occasionally get punished if you are a bad boy." Her fingers got back to work on his balls but this time gently stroking and playing with them to start working his arousal back up.

"Since you took something without permission I am going to punish you. I am going to start stroking you again in a second and you are going to have to make a very tough choice that has 4 options."

"The first option is I am going to stroke your beautiful cock to a nice full orgasm. I will milk out every last drop of those full balls. When I am done, you are going back in the cage for 2 weeks before I take it out to play again, but we try some other fun things while you are...out of commission."

"The second option is you ask me to ruin your orgasm. I will stroke you until you cum and then let go and let it dribble all over the floor. You will then be put back in my cage for a week before I stroke you again."

"3rd option is you beg me to lock your cock back up in that tight little cage. If you do that, I will do exactly as you ask and lock you back up for another week without letting you cum. Once you are free though I promise a nice sloppy blow job."

"Last of course is you could tell me top stop, and you don't want to do this anymore. If you do that, I will honor your request and lock you back up without orgasm, but you are going to pay for wasting my time and spend the next 3 weeks locked up before you can take the device off."

She applied another generous round of lube to his cock and began stroking. He didn't have a lot of time to make his choice before she took it away from him. He looked down pleadingly for another road not yet offered but the evil grin perched on her lips told him he would be offered no such mercy.