Keyholder's First Week

It all started with a letter. Beth got a letter in the mail. She opened the enveloped and a pair of keys fell on the table. Her fiancé lived a few towns away and with work and kids, they didn't always get to see each other as often as they would like. Due to busy work schedules, she knew that it would be a full week until they could get together again. Just thinking about how long it would be made her want to reach for the magic wand in her nightstand.

They sex they had was amazing and recently they had been exploring each other's fantasies more and more. It was fulfilling in more ways than one. Recently, she had seen Jason's toy chest. It was expansive to say the least. It would be an understatement to say that he had an interest in BDSM. There were all sorts of restraints, from ropes, to handcuffs, to metal spreader bars, as well as other toys that might come in handy. The vibrator and the strap-on both got thorough workouts on a regular basis. There was one other item that caught her eye. It was a chastity cage. They didn't talk about it specifically that much, but Beth was nothing if not thorough. She had looked up what it was and why some people were into them.

Damn, she thought, looking at the keys she knew were to the chastity cage that must at that moment be confining his penis. Can he really go a whole week without coming? Why would he want to? She bit her lip and took out her phone.

***

The previous evening, Jason had hatched a plan. He normal 5-minute shower took nearly 45 minutes as he tried his best to shave around his cock, his testicles, and his ass. He took his time, not wanting to have a cut if it could be avoided. He liked the way it looked. Beth was always perfectly clean-shaven. He loved the way that it felt on his hand and especially on his tongue. He hoped she would like it, but wasn't sure. More than anything else, having his pubic hair shaved made Jason feel submissive and he had resolved to make this a week where he felt submissive.

Getting out of the shower, he walked naked to the toy chest. He tried to think about work tomorrow intentionally. Since he had bought the chastity cage, he had only worn it to get the sizing right. He had realized that there was a bit of a catch-22 with chastity. The idea of his fiancé being in complete control of his most private part was extremely arousing. The problem was that when he tried to put on the cage, he would think of her and get an erection that made it very difficult to put the cage on. The manufacture said that it was made of bio-sourced resin and was supposed to be nearly indestructible. It was clear, so he could still see what he couldn't touch. He slowly pulled his balls through then ring, only 1.5 inches in diameter, one at a time and then his penis. He managed to make his erection go down enough to get into the tube. Normally, he was about 6 inches when erect and the tube that would be his prison for the next week was only 1.75 inches long.

Finally, he took a deep breath, turned the locked, and then sealed the keys in an envelope. He needed to move quickly before he lost his nerve. It was near midnight, but he was so turned on he knew sleep wouldn't come easily. He got in the car and drove the 30 minutes to Beth's house. He knew she was sleeping. In fact, that was part of the point. If he had to ask her in person he might back out. He lowered his car windows, opened the mailbox, and took a minute to say goodbye to something he had always been able to do without a second thought. For the next week, at minimum, he wouldn't be able to masturbate or touch himself in any way. There was no guarantee Beth would want to have any part of it, but he had an idea she might.

***

Jason's phone lit up as just as he was leaving a morning budget meeting. He saw Beth's name pop up on his watch, but waited until he got back to his office by himself to read the text. He didn't want his face to give him away to his colleagues. I guess she checked her mail, he thought.

Beth had thought for quite a while before texting. Her mind was racing with questions. She realized after a few minutes though that she shouldn't be uncomfortable. She wasn't wearing a cage and it didn't have to affect her if she didn't want it to. She decided to go simple and let him squirm a little bit. She just texted "Why?"

That's it? He thought. He had expected more questions or maybe even outage, but this was so open-ended he was caught off-guard and not sure what to write.

"The keys are for my cock cage. I was hoping you might be willing to hold onto them for me?"

"Why?"

Damnit. I have no idea what she's thinking. She could be pissed, she could have her hand rubbing her clit, or she could be doing her taxes. I'm not sure if this is a sext, a conversation, or a negotiation. Jason's mind spun, a condition that would become all too common over the next week.

"I've never gone more than 2 or 3 days without an orgasm and we're not going to see each other for a week. I really want to save coming for when I'm with you, to focus all of my sexual energy on you. I'm not sure I trust myself to do that on will power alone though."

"Hmmm. Well, I really don't like the idea of you masturbating. I might be able to get onboard. Is that the only reason?"

Jason squirmed in his chair, feeling his cock hanging heavier than normal between his legs.

"I really am turned on by the idea of you being in control. This gives you as much control as you want. I can't even touch myself without your permission right now."

"You're not afraid I might lose the keys? 😉"

A winking emoji! If she can joke, she's not mad.

"Oh god, please don't!"

"I tell you what. I'll hold your keys, but I decide when you get them back. Monday was your idea not mine. Maybe I'll unlock you on Monday, maybe not. Deal?" Beth hadn't told Jason that she was naked in her bed with the vibrator on low. Just because he couldn't have fun didn't mean she had to do the same.

Jason gulped. This seemed like a dream come true, but it was a bit intimidating. He started to wonder what he had gotten himself into; if it would be too much. It wasn't the last time he would think that this week.

"Absolutely! Thank you so much."

"lol. It's not like you have much of a choice. I'm holding your only way out. Remember that later if I send you another message." With that, she turned her phone off. Chuckling a little, she closed the laptop that had been open to a website on male chastity. She turned the vibrator up thinking of what the next week would bring.

***

Beth's mind raced with possibilities. Her research, always thorough, had given her a lot to ponder. Working from home, she didn't have to worry about what she looked up on the computer. This gave her plenty of time to think about what to do. She knew that Jason could still get aroused; he just couldn't do anything about it. In one sense, it was like a week-long edging session and she wanted to keep him on edge as much as possible. She had recovered from her first orgasm of the day. It didn't take long to recover as an hour of research was not dissimilar to reading erotica and she pictured her fiancé in every story. She took a picture of her ass in a tight, lacy, dark green thong that hugged her ass in all the right places. She took another of her cleavage in her matching bra. By the end, she had 10 pictures in all. They started with lingerie but ended with her fingers in her pussy, massaging her clit, and pinching her nipples.

Beth set a timer. She sent one picture, starting with the least racy, every fifteen minutes for two and a half hours. She had a newer iPhone, so they were "Live" photos. The last picture was animated and showed her hand rubbing her clit. She heard her phone ring very soon after the last picture was delivered.

"Those pictures are amazing, but you're killing me." Jason moaned in the phone. His voice was a lot huskier than normal.

"That's the point. How are you handling your confinement?" Beth asked, keeping her voice intentionally light.

"I have my lights off. Someone knocked on my door and I had to pretend I wasn't here because I can't stand up."

"Oh, that's too bad. You didn't like the pictures?" Beth asked jokingly.

"You know I loved them. You just might be a little distracting. I've gotten nothing done all day."

"Well, I'm glad you like them. It's your turn. Send me a picture in the next ten minutes to show me you really are in your cage." Beth's voice was suddenly more commanding than he was used to hearing.

"I'm at work...?" He stuttered confused.

"That's not my problem. You have 9:30 left. If you don't play the game, then I won't unlock you on Monday. 2 more things. 1 - Make sure you are completely naked in the picture. 2 - Take a sharpie from desk and write the date and time on your chest. That way, I know the picture isn't already in your phone."

Jason heard the line click and go dead. His face flushed and his heart race rose. Normally, being told he had to take a dirty picture at work would have given him an erection, but that couldn't happen today. He walked to the bathroom, much more quickly than normal. He wasn't making eye contact with anyone in the hallway. Suddenly he was convinced that everyone knew he was in chastity. They must, right?

When he got to the bathroom, he let out a breath he didn't know he was holding. He splashed some water on his face. He took out his phone and sharpie, then put them on the counter. Thankfully, it was a nice office so the bathroom was private instead of a stall where someone could see something. He stripped as quickly as he could and hung his clothes off the wall hook. He carefully wrote the date and time (3/26, 12:15PM) over his heart and above his chest hair. As he was about to take the picture, a knock on the door made him drop the phone. Thankfully, he caught it before it could hit the floor and make a noise. He mumbled, "One minute," then took the picture and got dressed as quickly as possible. 'This may be a long week,' he thought.

Beth smirked as she opened and saved the picture. She thought, 'This week is going to be a lot of fun.'

***

Jason was usually up long before the dawn, but he was feeling groggy on his second full day of chastity and hit the snooze button again. Before he could lay back down, his phone went off. He shook the cobwebs from his head, realizing it was a text and hoping everything was ok. No one texted him at this hour unless something was wrong.

"Good morning sweetie. Just wanted to check in and make sure you slept ok."

It was Beth. Thankfully she was being nice. She was sexy as hell, but he wasn't sure he could make it to next Monday if every day was as tough as the last. It was only Tuesday.

He took his time. He figured he might have botched introducing chastity, just leaving the keys like he did. He should be honest and owed her the details. "I managed I guess. It took a lot longer than normal to fall asleep. I was so turned on thinking about you and everything you did today. I didn't realize that they body tries to get erections at night. I mean, I knew from reading but I didn't know what is was like. My cock woke me up at midnight and 2 with erections that wouldn't go away. At one point, I had to sleep on my side with a pillow between my legs."

"I'm sorry. I slept like a baby after my second orgasm. It's better than a sleeping pill."

Jason groaned as a second text from her came through.

"That almost sounded like complaining. You don't want to give up after just one day, right?"

"Definitely not. It's a mind trip, but I don't want to back out."

"That's good, since I have the keys. I can't imagine you want to call a locksmith. How much does a locksmith charge to work on a penis?" Beth chuckled to herself, trying to picture her fiancé paying hush money to a locksmith to unlock him.

"Glad the keys are safe and you seem to be having fun..."

"Speaking of fun..." Beth left him dangling for a minute. She knew he had a pack of 3 anal plugs, but hadn't been able to get the largest plug in on his own. I may have to force the big one in for him next time I see him. She shook her head, focusing on the matter at hand. The medium was 3.35 inches long and 1.3 in diameter. "Before you go to work, I want you to put in the medium butt plug. Record yourself putting it in and send it to me. You don't get to take it out for the day unless I give you permission."

'Holy shit', Jason thought, smiling faintly. 'Where did this vixen come from?'

"Yes, Ma'am." Liz shivered at the word "Ma'am." She didn't realize how much she would enjoy hearing that.

Jason went through his morning routine -- shower, breakfast, etc... -- without bothering to get dressed. What was the point? He took out a tripod he kept for this purpose. 'Maybe I hadn't envisioned this exact purpose, but I have sent her a few pics before'. He had never sent her a video and every time they played with his ass, she had been behind him so he could hide, slightly at least, how much he loved it. He got out the plug and the silicone lube. He knew he was going to be wearing if for a while and wanted to make sure he could get it back in if he had to use the bathroom at work. He ran his thumb over the jewel at the end. 'A princess plug?' He thought that was what they were sometimes called in the erotica he read. It was hard to feel macho with a princess plug in your ass, but it did make him feel submissive and slutty.

He pressed record on the phone and sat on the edge of the bed. He knew she wanted a little bit of a show, otherwise a pic would have been good enough. He sucked on the cold steel of the plug, trying to warm it up a little and keeping eye contact with the camera/Beth the whole time. After it was sufficiently warmed, he laid on his back, lifting and spreading his legs. He rubbed his testicles with his right hand while his lubricated left hand put first one, then two fingers into his ass. He thought he was ready, but he enjoyed the feeling and kept going for a little bit. Finally, he picked up and lubed the plug. He wasn't sure how much was strictly necessary for wearing it to work, so he tried to put extra on. He twisted as he pushed, letting his ass dilate and relax a few times before pushing it all in. After taking a minute to recover, his penis still unsuccessfully trying to break free from its prison, he watched the video back quickly. He panicked for a second. 'I look like such a slut. What if someone sees this? What if I don't send it and she doesn't give me the keys back?' After a brief mental tug of war, Beth won out and he pressed send.

***

Beth had a busy morning. After getting the kids ready for school, she was buried in orders. She didn't have time to think about sex again until almost noon. When she finally got a break, she saw she had a few missed texts from Jason. 'Not very productive today, is he?' She only skimmed them as she went to the video. 'Oh my.' She felt a warming tingle emanating outward from her clit as she watched the porno made only for her. She pressed the airplay button on her phone as she walked to the living room and the video started playing on loop on the television. She laid on her back on the couch, her ass raised up on the arm and her skirt wantonly lifted over her waist. In no time, her fingers were soaked with her own juices. As Jason started masturbating his ass with one finger, she mimicked it. Her other hand was rubbing her clit furiously with just one finger and she inserted a second into her ass. She clenched right as Jason seated the plug in his ass, pushing her over the edge.

It took her a few minutes to come back down from her high. She was definitely enjoying herself, but found she was looking forward to Monday as much as he was. She saw the windows were open and blushed, hoping none of the neighbors could have seen or heard her. She usually wouldn't have let herself get carried away. A knock on the door -- her first customer of the day here to pick up her order -- brought her out of her reverie. She smoothed out her skirt and her hair, hoping there were no obvious signs of what she had been up to.

Meanwhile, Jason had found that he could mostly function with the plug in. He walked a little slower than normal, perhaps, but people wouldn't notice that. In his office, he had a plush chair. He could sit on his leg in such a way that the pressure was lifted off the plug. It wasn't until his meeting close to lunch with department heads that it really got to him. They were supposed to go over budget projections for the next fiscal year. They were meeting around a high circular table with hard stools. As he sat down properly, the plug was pushed as far up as it could go, rubbing against his prostate. He felt his eyes roll to the back of his head and had to stifle a groan. This was going to be a quick meeting. He needed to make sure of that.

***

Around 6 that night, Jason asked if he could take out the butt plug. He got a joking response that he wasn't ready yet. 'Ready for what?' he thought. He was starting to stir. He was so horny, but wasn't able to get any relief. He couldn't seem to go thirty seconds without thinking of Beth. He always thought of her often throughout the day, but this was something else entirely. He was reminded of her and of her control with literally every movement. Something would constantly shift and he would feel the plug in his ass or the cage on his cock and think of Beth.

Finally, around 9, he got a simple text. "Strip. Get the large strap-on dildo, your handcuffs, and your tripod. Wait for instructions." He had that accomplished in less than a minute and had to physically put the phone down to keep himself from replying. He knew that wait meant wait, not pester.

Surprised, he saw his phone light up with Beth's face as she initiated a FaceTime call. "Hey honey," she said lightly. "How are you feeling?"

Jason scrutinized the picture. He could only see her head and part of her upper chest. It looked like she could be naked, but he couldn't be sure. "Hi Beth. I'm ok. I don't think I've ever been this horny, but other than that I'm ok. How are you?"

"I'm great. I can have all the orgasms I want though. But I don't think you really want to talk about the day, do you?"

"No," he almost sounded short of breath.

"No what?" she replied expectantly.

'What is she looking for?' Realizing the predicament he was in, he didn't want to disappoint her. "No, Ma'am?" he ventured nervously.

"Good boy." He flushed at the implied condescension, but in his current state it was just more fuel on the fire. He watched the screen in awe as she had pointed it at the ground and suddenly a sheer white bra and panties set hit the ground. He couldn't wait to see her naked and aroused.

"Now, put the phone on the tripod and point it at the tub. Make sure all your toys are on the counter of the tub, then get in."

Jason quickly followed all directions. He was disappointed he couldn't see her; he really wanted to, but the screen of the phone was facing the opposite direction in the tripod. After the morning, he had an idea that she was going to make him perform, which turned him on in a really submissive way. Jason was also lucky to have a large circular bath that doubled as a hot tub.

"It's too bad you can't see me naked. You haven't earned it yet have you. Do you hear that buzzing?"

"Yes Ma'am."

"That's my bullet vibrator. I have others that would get me off faster, but I want this to last a little while. You're going to put on a little show for me. If you do everything I say, you might get a peek at seeing me naked. If you don't, you losing any chance you have at coming on Monday. Do you understand?" Her voice alternated between husky and stern.