Keyholder's First Week

"Yes, Ma'am." Jason's breathing quickened as he tried to simultaneously read her mind over FaceTime and listen hard enough to try to discern what exactly she was doing with that vibrator.

"Take out the plug. Get the strap-on dildo and stick it to the wall even with your cock. It'll work like a suction cup. If I remember, that dildo is almost identical in size to you, but it's not stuck in a cage. Your balls look pretty swollen, though, and almost the same color purple. I wonder what color they will be by the end of the week? Now, handcuff your hands behind your back and get on your knees."

"Yes, Ma'am." He knew it was all he was allowed to say. He gingerly dropped to his knees, feeling the cold steel of the cuffs lying near the top of his ass. He thought he heard the buzz from the phone get louder.

Beth had been brainstorming all day. She wanted to make him feel as submissive as possible. If his current state, she thought she could make him do anything. She tried to block out the pulsing of the vibrator.

"Suck it."

"What?" Jason was confused.

"The words you are looking for are 'Yes, Ma'am' if you want to have any chance at coming this week. We could always wait a second week."

"Yes Ma'am. I mean no, I mean I'll do it, just please don't make me wait a whole two weeks Ma'am."

"Then let's see what you've got. Try to touch the wall with your nose."

Jason nodded and moved as quickly as he could until his lips were pressed to the unfeeling dildo. He couldn't believe he was about to do this. He couldn't fathom another 12 days like this without being able to come. He had never had tried to take anything like this in his mouth. He opened his mouth and was surprised he could only get the first third in his mouth.

"Try getting it wet," Beth suggested helpfully.

Jason spit on the dildo and licked its length up and down, top and bottom, trying to lubricate it as much as he could. He took it in his mouth again and bobbed up and down. He made a little more progress.

"C'mon. You're never going to get there at this rate. Push that cock down your throat."

Jason pushed his head forward until he started gagging, his eyes watering. He had managed to get it almost ¾ of the way in his mouth. He tried to hold it and breathe through his nose, but couldn't last long before he backed off, heaving and trying to catch his breath.

"Not bad, but I think you can do better with a little training." Jason smiled at the almost compliment, trying to blink the water from his eyes and hoping he had done enough to stay in Beth's good graces.

"Time for part 2, are you ready?" Beth asked, the vibrator getting louder again.

"Yes Ma'am."

"Slide the vibrator down the wall and lube it up. Then I want you to fuck yourself on it."

"Yes, Ma'am." He could tell by her tone she wasn't kidding and he was not going to test her again. He heard her laugh as he struggled to move the dildo and then put the lube on it with his handcuffed hands behind him. He saw the position pushed out his neglected cock and gave Beth and unobstructed view.

Once the cock was slick and at the right height, he found he still spread his ass cheeks with his bound hands. His forehead touched the floor.

"Ooh, face down, ass up. This is a good view," Beth encouraged.

The dildo was larger around than the plug that had been in his ass, but his hole was already somewhat prepared and it was easier than it normally would have been. After a few moments of pressure and concentration, he felt his asshole expand and the slick cock was suddenly 2 or 3 inches in him. He let out a guttural moan.

"You have a greedy asshole, don't you?"

Jason groaned and nodded as he leaned forward and back again, slowly taking 4 of the dildo's 6 inches.

"I can't hear you. If you want to see those keys again, look at me and answer."

Jason turned his head, his chest still on the floor and his ass swallowing the purple cock over and over. "Yes, Ma'am, I have a greedy asshole. This would only feel better if you were behind me wearing it."

"That's better. Now, speed up."

Jason managed a faster rhythm than he had ever been able to solo. "Faster, hit the wall with your ass."

The timbre of Beth's voice had been rising. He knew she was close. If he was going to be what she masturbated to, he wanted to make it good for her. He slowed to bottom out on the purple cock, gasping as it went all the way down. He started slamming his ass down with vigor and Beth could hear it thumping against the wall. "Don't stop," she whimpered. He heard her lose control, then the buzzing stopped and she went quiet. He didn't dare stop, because she hadn't told him to. He was definitely going to be sore tomorrow. He had no idea how much time passed when she came back.

"Ok, ok, ok." She was still catching her breath. "Stop and sit up, but leave the dildo in your ass."

Once he did, Beth continued. "Wow. There is a puddle of pre-cum under you. You're lucky you're handcuffed or I might make you try some. Maybe we don't need to unlock you if you can come that way. What do you think?"

Not being able to see her, he couldn't tell if she was joking. What did she want him to say? "I need to come like I've never needed to come before, Ma'am. You're torturing me, in a good way I mean. I'll trust you. Whatever you want me to do."

"Good boy. That's what I wanted to hear. I'm going to take a hot, relaxing bath. I suggest, once you get the cock out of your ass, you take a very cold shower. Goodnight."

"Goodnight Ma'am. I love you. And thank you."

"I love you too."

The line went dead and Jason had to extricate himself from the dildo and the handcuffs. He wondered, cleaning the toys and getting into the cold shower, if someone could record a FaceTime call.

***

Wednesday dawned for Jason with a faint ache in his balls that wouldn't go away. His ass was sore too, but not as much as he had anticipated. He could see that he had gotten a message while he slept. Beth had sent an email around 2 in the morning. First, it told him that she was going into the city to meet a friend for the day and likely wouldn't have time to play. He was somehow both disappointed and relieved. If they kept up yesterday's pace, he thought he would explode or just pass out from overstimulation at some point.

He kept reading. She had a checklist for him designed to keep him stimulated all day long. There were fifteen stories from http://tags.literotica.com/chastity. This was his favorite erotica website and it looked like all of the stories involved his predicament in some way. Beth instructed him to read one every hour from 6am until 8pm and text her what turned him on the most about each one. 'Wow. That's devious. She's going to use my own fantasies against me.' Second, after the last story, he needed to spend 20 minutes trying to deep-throat the dildo with a plug in his ass (she said he needed to practice with all of his "holes filled up, like a good little slut") and send her a pic of his progress.

'It's going to be a long day,' he thought, wondering when she could possibly have had time to not only read, but curate all of these stories. He browsed the stories for a few minutes and saw that they all were rated 4.5 out of 5 or higher. Only a small percent of the site got rated that highly. She picked out the good stories that had a lot of details. He groaned a bit, surprising himself. He loved this stuff; had gotten off on it many times. That was precisely the problem though. Usually his cock was hard by the third paragraph. A conservative estimate of 15 minutes spent reading each story meant he was in for nearly 4 hours of his cock straining hard against the cage.

He read the first story over breakfast, taking a break halfway through because his balls were too sore to go on. He opened his messages app and wrote, "The part that turned me on the most was when she fucked him with a strap-on with his cage still on," before he got ready for work. The reply? "1 down, 14 to go."

Work was interminably long. There were things in some of the stories that he was not precisely into, but he didn't really notice anything that he would outright refuse to do. He only had few red lines, probably fewer with his cage making him think about Beth and sex and nothing else for 3 days straight.

He spent the rest of the day sending texts like:

• "The part that turned me on the most was when she tricked him and didn't release him like they planned."

• "The part that turned me on the most was when she made him beg."

• "The part that turned me on the most was when she finally unlocked him, but she made him wear a cock sleeve so he couldn't feel it."

• "The part that turned me on the most was when she threatened to show her friends his chastity cage."

• "The part that turned me on the most was when she was able to ruin his orgasm by letting go at the last second, so he could watch the cum dribble out with getting any satisfaction."

• "The part that turned me on the most was when she was able to milk his cock dry without taking the cage off, using her fingers in his ass, then a vibrator on his prostate, then a wand on his balls."

• "The part that turned me on the most was when he got to tie her up and tease her, but she had left the keys at home. He could make her beg and he could get her off, but he couldn't do anything about himself."

• "The part that turned me on the most was when they had amazing sex. There was nothing kinky about it, they just ravished each other after time apart."

• "The part that turned me on the most was when he was tied spread eagled to the bed. She got off sitting on his face, then rode him until he was begging to come. Then she whispered, 'beg me to lock you back up.'"

• "The part that turned me on the most was when she made him come over and over and over, forcing every drop from him until he begged that he couldn't take it anymore and should be locked back up."

By the time 8 o'clock rolled around, he felt stripped bare in a way he hadn't when he was actually naked. She had cleverly pried some fantasies out of him that he had never talked about with anyone. She had only responded with her countdown and some cute Instagram-worthy pics at ice cream shops and vintage clothing boutiques. He was practically writhing and she seemed to be having a lovely time. He wasn't annoyed, per se, he was just horny and desperate. He stripped off and got the medium plug in. He brought the tripod, dildo, and phone downstairs to the kitchen where there was tile floor. He put the dildo's suction cup bottom on the floor so it was pointing straight up. He had set the phone to take pics automatically at regular intervals. After about 10 minutes, he had managed to get his nose to touch the floor and could feel the dildo in the back of his throat. He held it in his mouth as long as he could, his eyes watering. After catching his breath and looking through the phone, he sent 2 pics. The first showed the light shining off the plug in his ass and the full length of the dildo; the second showed his eyes red and watering as the length of the purple cock was in him.

He waited a few minutes and had just about given up on any more communication from Beth when this text almost sent him over the edge: "My friend is impressed. She didn't think you could deep-throat it. I had faith in you though. She wants to see you bounce on it. Send us a video. You have 10 minutes."

'What the fuck?' He looked at his phone for a good 2 minutes. 'Is she serious? Did she show her friend or is she just fucking with me? Will she really show her friend a video of me riding a dildo? If I say no, there's no telling when I will get out.'

It took him only another minute to decide, running upstairs to get the lube as quick as the cage and plug would allow. He pressed record after making the cock as wet and slippery as he could. He knew that Beth liked a show, so he started by squatting over the dildo and taking the whole thing in long strokes. He couldn't maintain that for long. He let his knees touch the ground and rode it as though he were on top during sex. His cock bounced obscenely and there was no beating around the bush. He looked like a whore who was getting off on anal sex. He recovered himself enough before the 10 minutes was up to look directly at the camera, sit all the way down on the cock, wipe the pre-cum off his cage with a finger, and then bring it directly to his lips. 'If I'm giving Beth/them a show, I might as well go all the way.' Hoping it was just for Beth, he got off the dildo and pressed send before he could second guess himself.

On his way to yet another cold shower, he got one last text: "We both thought that we really hot. Love you. Goodnight."

***

Thursday was the first day that they seemed to be taking it easy. They texted on and off all day like they normally did, just talking about their days. Jason had realized that the less the thought about chastity, the easier it was. He couldn't block it out when he was constantly reading or doing erotic things, but when work was busy, it was possible. Thursday was shaping up to be a decently calm day, at least by the standards of the week, until lunch.

A little after noon, Beth got a text notification from Amazon saying that a package had been delivered. She smiled and turned on her stopwatch, realizing the fun was about to begin. Jason had no idea what he was in for.

Jason was in his office when a secretary knocked on his door and gave him an Amazon package. He didn't remember ordering anything. His pulse quickened as he waited for the secretary to leave. He locked his office door and opened the package. There was a large anal plug called the Lovense Hush. He was familiar with the company. Beth had the g-spot version and he had once talked her into wearing it out to dinner for almost 2 hours; it could be controlled from a phone and he had kept her on edge as long as he possibly could. There was also a small bottle of lube and a note, the kind Amazon uses to send birthday messages. It said: "I got a text message as soon as this was dropped off. You have exactly 15 minutes from then to pair this to your phone, put it in, and give me control."

'Shit,' he thought. 'How long did the secretary have it before I opened it?' He opened the box and put the plug and lube in his jacket pocket, then threw the evidence in his bag. He rushed to the bathroom; he wouldn't risk it in his office even with the door locked. Some other staff had keys and it might look suspicious.

He barely had the door closed and locked before he dropped his pants. He looked at the plug. There was no way it was going in right away. He wasn't relaxed and he didn't think he could get it in without some preparation first. He lubed his hand and worked his way up to three fingers after a few minutes. He tried to push it in, but it hurt and his ass just wouldn't spread that far. The Hush was 1.75 inches wide. Jason kicked off his shoes and took off his pants. Getting on his knees, he braced the plug between the wall and his ass and pushed. There was a moment of blinding pain; he didn't think it could fit, then he thought he would tear in half, but he made it. As he sat catching his breath, he turned on the phone and connected the toy over Bluetooth. In the Lovesense app, he clicked on the "Long Distance" button and gave Beth control. He finished getting dressed and washing the lube off of his hands.

As he got to his desk, he felt a vibration, but it was only his phone. He really had to struggle not to walk funny with the size of the plug. He answered his phone, "Hello?"

"You're 15 minutes late," Beth said sounding annoyed and impatient.

"I'm sorry Ma'am," he stuttered. "I don't know when the package came in."

"That's not my problem. You kept me waiting and didn't follow your instructions. Do people who don't follow instructions get to come on Monday?" She sounded like a school-teacher explaining something to that one kid in every class who just doesn't get it.

"No, Ma'am, but please don't take away my orgasm. It's so hard already and we're only on day 4," Jason pleaded. He wanted to be stoic, but he just couldn't.

"Here is what we are going to do. I already have plans for today, so I want you to think about what you did and how you can make it up to me. Plan a punishment for tomorrow night. I will call you at 9PM. You will administer it while I watch. If it is good enough, I'll consider letting you come on Monday. Understand?"

"Yes, Ma'am. I'll punish myself tomorrow," he replied resignedly. 'She got me again. That's clever. I might be way harsher than she would be, but I can't go easy in case she tries not to give me the keys back.'

"Good." A low vibration started in his ass and he moaned into the phone.

"Now, now, you are going to have to do better at keeping control. That's only the low setting and this has a 2-hour battery."

Jason closed his eyes. "I'll do my best. I have a meeting in an hour. Will you turn it off for that?"

"No guarantees," she purred. "Now, how far is it to the nearest coffee shop?"

"A mile or two. I can drive in a few minutes."

"Perfect. I want you to go to the main office. Ask the secretaries and anyone in there if they want any coffee. Then, go there and order, but no drive-thru. You have to go in and actually talk to people."

"Oh God. I don't know if I can do that. Ma'am." He remembered to add that superlative just as she inched the vibrator up slightly; it sounded like the vibration trailed off his tongue.

"You can and you will. Don't you remember making me talk to the waitress when you were in control?" Her voice was playful again. That was good; playful was better than annoyed.

"Then get going. Enjoy this pattern. It goes from 5-25%. It won't get any easier from here." The line clicked and the vibrator started going through a looped pattern. Jason let his ass clench down for a minute, using the desk for support. He took a deep breath, stood up, and went to the main office.

As he got there, the vibrator pattern changed, starting and ending slightly higher. A text notification on his watch said 30%. He didn't realize that Beth had put in her Lush vibrator and synced it to his, so they would experience the same vibrations, albeit in different places. The biggest difference is that no one would hear her moan.

Of course, because of Murphy's Law, everyone wanted something and a co-worker insisted on going with him. Jason wrote down their orders while hoping against hope that no one could hear the faint rumbling coming from his ass.

As he and Jack got in the car, Jack asked if he heard something. Jason replied that he should probably have his car looked at and opened the window a bit to mask any noise with wind. Naked in her bed, Beth was enjoying the sensations and the mental stimulation that came with fucking with Jason. She rolled onto her stomach, changed the settings so that the highest spike on the roller reached 50%, and ground her pussy into the pillow between her legs.

When the spike hit 50%, Jason was not prepared. He couldn't anticipate anything without being able to see Beth. As his ass clenched, his foot when down and he nearly crashed into the car in front of him. His knuckles were white on the steering wheel. 'I'll have to talk to her later about vibrating and driving,' he thought.

"Dude, what the fuck? You ok?"

Beth killed the loop and just set it to stay at 55%. These vibrators were a lot stronger than the bullet vibes a lot of people have. The vibrations from inside combined with rubbing her clit, Beth hit her first orgasm and then paused her vibe to recover.