Memoirs of a Keyholder

Note from the Author

This story contains themes of chastity, denial, femdom, and humiliation. If those don't appeal then I'd suggest trying out a different story.

Age 18

Miranda stands across the room from twenty, naked teenage males. The boys are looking at the ground, fidgeting uncomfortably, their thumbs ziptied behind their own backs.

Next to her, fully clothed, her female classmates eye up the males like lions observing a pack of nervous antelope. Some giggle and point, others try to conceal heavy breathing. Hairs stand on end in the charged air, as if an electrical storm was circulating overhead.

When the teacher says it is time, Miranda crosses the room almost lackadaisically, standing next to her friend Joshua while other girls scramble for preferred partners.

You might think that the handsome or athletic boys are snatched up first, but some of the girls are bullies and they have other things on their mind.

Joshua seems simultaneously relieved and terrified at Miranda's choice. He does his best to conceal any feelings on his face, though his partial erection gives some indication of what's on his mind.

"Stop being so nervous," she whispers in his ear. "I'll make sure you have a good time."

The teacher guides them through various exercises. Icing down the genitals, putting on and taking off a chastity device, applying lubricant, attaching cock rings, sleeves and other sex toys.

Finally the teacher announces thirty minutes of "unstructured play". She says this with a wink.

Left untended with their prey, the girls go a little wild.

Miranda can hear the girl next to her whispering to her charge, "Do you know what a ruined orgasm is? No? You're going to find out soon."

Miranda surveys the class, and sees another boy squirming as his giggling partner inserts a finger up his anus.

She turns back to Joshua.

"You said it's been three weeks since your mom let you out, right?"

"Yes." Joshua's reply is barely audible.

"Well let's make the most of this then. Maybe we can squeeze out an extra round. Just tell me what feels good okay?"

Through trial and error Miranda learns what makes Josh happy. After only a few minutes he's warning her that he can't last much longer.

Surreptitiously she leans in and presses her breasts against his arm.

"Does that feel good too?"

He glances down and sees her breasts mashed together against his arm, piled up high in the confines of her tank top. He'd always seen her as a bit frumpy, his nerdy friend. Now he can barely contain himself.

"Oh my god" he whimpers.

Miranda doesn't have time to grab the tissue box on the desk next to her before the barrel in her hand fires off an errant shot. She manages to catch the second and third slugs of cum in her free palm and by then Joshua is more leaking than shooting and she does her best not to let anything overflow.

Unconsciously she rubs her thighs together and then stops herself when she realizes what she's doing. She doesn't know any girl who has a shorter fuse than her. She's had orgasms from simply sitting above the wheel on the school bus, and doesn't want to get carried away just yet.

Calmly she inspects the swirling white elixir in her palm, wondering what it would feel like to have the rapidly cooling liquid inside her.

"Do you think we have time for one more round?" she asks.

Joshua nods yes.

***

Miranda is being led by Ms. Stevens down the hallway. They stop outside of the old male changeroom where Ms. Stevens pulls out a long device with a plastic head, exposed wires and a basic motor.

"Do you know what this is, Miranda?" Ms. Stevens looks at her with disapproval.

"It's a toy I made in my electrical engineering elective."

"Do you want to explain how it came to be found in Michael Davenport's backpack?"

Miranda sighs. "I lent it to him. I thought he could use it."

Ms. Stevens doesn't wait before continuing. "Well he was caught using it in the male bathrooms. Luckily before he finished. You do realize it is illegal to make a vibrator, especially for male satisfaction? All government approved vibrators have known frequencies which can be detected by chastity devices to alert the authorities. This monstrosity qualifies as a black market good."

"Yeah, I get it, that's why I made the thing. Michael's mom is a bitch. She hasn't let him out in three months. The poor guy is going crazy."

"I'm sure Michael's mom is more than capable of making decisions for him, Miranda. And this isn't the first time I've heard complaints from teachers about your behavior regarding male chastity. You are being manipulated by these boys and it's high time that someone intervened. Come inside."

They walk through the door together.

Miranda bursts out laughing when she sees the room.

"Sweet Jesus, what the hell is this?"

The room has been renovated into some sort of sex-ed abomination. Posters with anatomical drawings or corny slogans line the room, but Miranda barely notices them because there are six glory holes spaced along the walls and they are fully occupied by erect penises. Standing straight, or curved as the case may be, the semi-disembodied organs look almost like suction dildos attached to the wall, but they are in fact affixed to owners in adjacent rooms.

"This is your punishment Miranda. Before I pulled you from your lesson, I went to a random Grade 13 class and asked for volunteers. The boys were told that they would be released from their cages, and that a female student would be allowed to touch their genitals, but they would be punished if they ejaculated. The reason I only have six volunteers on the other side of these walls is because there was only room for six. Every single boy in the class volunteered."

"Okay, what's your point?"

Ms. Stevens continued. "My point is that boys like to be teased. Their natural station in the world is being denied to the point that they want to serve us. When you release them too often, they forget their place. Of course they protest, but it's up to women to keep them in line. You are failing the sisterhood."

"Okay, well I don't want to tease them. I think it's cruel."

"If it's cruel then why did every boy volunteer to stick their dick through a hole when they had no idea what was on the other side? This is a lesson to you just as much as it is for them. Do you see what's underneath each of the glory holes?"

Miranda rolls her eyes before scanning the room. "Yeah, you have stools underneath and plates are on the stools, I guess to catch their jizz."

"Not quite. Remember they were told that if they ejaculated they would be punished. The plates are already full of liquid. I had our biology teacher extract a dilute sample of resin from a poison ivy plant. If any of the boys become flaccid, their penises will dip into the solution and they're going to experience the most excruciating rash of their young lives."

At this point several of the boys attempt to withdraw from the wall, but it seems that they are restrained in some manner that Miranda cannot see, and their muted protests suggest that they are probably gagged as well.

Ms. Stevens continues, "So for the next hour you need to make sure that all of these cocks stay hard. At 4 o'clock the boys will be released from the other side. I'll just be sitting on this chair to make sure you don't try and cheat."

"What the fuck, Ms. Stevens!? This is psychotic!"

Ms. Stevens only smiles as she sits down and pulls out her phone to pass the time.

Miranda dashes across the room to attend to a member that is already fading below horizontal and threatening to make contact with the liquid beneath it.

"Hey hey, it's okay," she says reassuringly as she grabs the poor boys' fading hard-on and strokes it hurriedly. "All that's going to happen is there's a hot girl on the other side of this wall, and she's gonna play with your cock for an hour okay? Nothing to worry about."

Miranda reaches out with her other hand to simultaneously pleasure the next boy who sighs with relief at her touch.

After a few moments she moves across the room and repeats the process.

Things go well initially until her hand starts to cramp. She has to let one arm rest at a time and contemplates using her mouth, though the stools are too close for that to really be an option.

As the hour passes on she begins making lewd comments for the boys' benefit, describing how turned on she is getting on the other side of the wall. She's panting from exertion and she can only hope that the boys find it convincing.

Then, with twenty minutes left she gets carried away and one of the boys shoots his load without warning.

"Fuck, fuck fuck," Miranda curses as she watches the eruption. "I'm sorry, I'm so sorry," she says to whoever is on the other side of the wall. There is no way that he is going to make it. As best she can, she coats his wilting cock with a thick layer of her saliva, hoping it will act as some sort of barrier, and then abandons him to save the others.

Once his penis makes contact with the liquid he begins thrashing about on the other side and is mercifully released.

As the clock on the wall is ticking down, Miranda knows she has gotten through with only one 'casualty' and spends her time stroking a cock that she has come to think of as her favorite. Straight and polished and leaking rather profusely into the plate of liquid itch below.

"You fuckers owe me you know that?" She jokes to the hidden boys as she patiently strokes the twitching cock in front of her. "I should have each of you on your knees for hours to make up for the trouble you've caused me."

Ms. Stevens speaks up from the corner of the room for the first time, "Miranda, you might be a bit of a nerd, but you're a pretty girl and these boys are in chastity for 24 hours most days. You don't need to play with their cocks for an hour to get them to serve you. That's the point I'm trying to convey."

The alarm on Ms. Stevens phone goes off suddenly and someone must be on the other side with the boys because one by one the penises disappear from the walls like mammals retreating into dens. Miranda laughs with relief.

"It's just water on the plates you know." Ms. Stevens gives her a conspiratorial look. "This isn't a prison after all. But if you'd like to have one of the prisoners, one of the boys, sent in here, I wouldn't object. They will be locked up in their cage of course."

Miranda is dripping sweat and her arms hang at her sides exhausted. If she had to be honest she would admit that her underwear are also drenched, though not with perspiration. She would much prefer to pleasure herself right now but she doesn't think she has the energy.

"That boy on the left, I think I recognize his cologne." Miranda says.

"Jason Cartwright?" Ms. Stevens answers. "Shall I send him in?"

Miranda nods, yes.

"Would you like him blindfolded?" Ms. Stevens asks.

"Yes."

"I think he'll be very happy to express his gratitude."

Age 19

Jason and Miranda are not exactly a couple. In the old days they would be called friends with benefits, though most of the benefits accrue to Miranda. At least that is true until one cold night in January when Jason tells Miranda that he has discovered where his mom keeps the spare key to his chastity cage.

They plan to bring the key back to Miranda's place on a night when her mom is working late. Miranda is actually more enthusiastic about this plan because she knows it can work. Jason is less certain.

Male sexual education is limited to female anatomy and practical ways to bring womens' bodies pleasure, but they are kept somewhat in the dark about their own physiology and remain very murky on the details of chastity surveillance. That's the cause of Jason's reluctance - he fears he can't get away with anything. Miranda, on the other hand, is convinced that if he is blindfolded and in a dark room then his memspecs account will have nothing to record and there can be no problems.

And so one night they find themselves in Miranda's room. Jason is sitting on the edge of the bed, blindfolded and naked. It is only the second time she has seen his cock outside of it's tiny jail cell. She is simultaneously drawn to it and repulsed by it. Penises look so unnatural outside their cages, she thinks.

The young couple kiss and pet and Jason is too scared to perform at first but arousal overcomes fear and Miranda does have a small amount of experience getting him hard.

Out of long habit she pushes him to his knees and he warms her with his tongue. Then he is rising, licking her breasts and her neck. When he goes to kiss her lips she turns away, not wanting to taste herself, and he has to settle for nibbling on her earlobe.

Then their hips touch and they begin grinding on one another. Grinding, rubbing and then suddenly he is inside of her for the first time. She finds the experience stiff and almost painfully tight whereas Jason finds it warm, and wet and also too tight, but more in the way that he can barely contain himself. Miranda asks Jason to slow down and he does, but not enough for his own good because all at once he is gasping and quaking and then apologizing and Miranda realizes that it is over too soon.

She is actually angry with him. She allowed him to have penetrative sex with her and he ruined it selfishly. No woman should tolerate such behavior.

She is about to let him know when the door flings open and Miranda's mother enters like a steam locomotive - red and loud and angry. And she hasn't even realized yet that Jason has just ejaculated inside her daughter.

When the two lovebirds disengage, Miranda's mother sees the evidence of Jason's crime streaming down her daughter's leg and she goes apoplectic.

"You filthy animal!" She screams so loudly that she actually spits in Jason's face, and Jason, as soon as he manages to get his blindfold off, looks like he has made eye contact with a Gorgon.

Miranda screams at her mother to get out of the room, but Miranda's mother is having none of it. "Do you realize how much trouble he is in? Do you know what will happen if I press charges?"

Miranda knows that the answer involves two piercings and a steel cage and even though she's angry with Jason she's not angry enough to want that for him.

"You are going to get down and lick every drop of your slimy seed out of my daughter right this instant."

Miranda's mother is from the school of chastity feminism which holds that semen is to be treated like a toxic spill which only men are fit to clean. She pushes Jason to his knees in case he was having second thoughts.

Out of shame, Miranda covers her breasts with one hand and forearm and helpfully uses the other to guide Jason toward the rivulet that has now reached her knee. Her cheeks burn bright red with embarrassment but things are getting worse because according to Miranda's mother, Jason's mother is on the way and she is so furious that she hasn't decided whether to phone the police on her own son just yet.

Jason has by now finished licking up any swimmers who were naturally unselecting themselves by freestyling in the wrong direction. When he reaches the source of the leak, muscle memory takes over and he falls into the old habit of teasing Miranda's outer lips. She moans involuntarily and her mother smirks to herself. But then Jason plunges his tongue inside her, following orders to clean up his mess and Miranda groans like a 20th century porn star. She is now enjoying herself much more than she did at any point during their trivially brief act of coitus.

When Jason is satisfied that he can no longer taste his own jizz, he is at something of a loss for what to do. Wanting to appear appropriately contrite, he continues licking Miranda, but now moves up to her clitoris.

"Mom, tell Jason he can stop now."

Miranda's words are the opposite of convincing.

She is unsure why, but she has never felt this aroused in her life. Perhaps it is the danger of what they were doing. Maybe it is the act of being watched or the knowledge that she is degrading her own friend.

There is no time to consider these possibilities since there is a knock at the front door and Miranda's mother leaves to answer it. Soon Jason and Miranda's mothers are coming up the stairs, making furious mom noises, but they go silent abruptly when they enter to the bedroom.

Miranda is now holding Jason's head, trying to force his mouth against her sex and he is clearly struggling to breathe as she fucks his face relentlessly. Miranda feels exposed, her nipples are hard in the night air and she can sense the gaze of the two women on her body but this only heightens the comingling feelings of domination and vulnerability.

Her first orgasm grips her like a seizure and when it finally crests she smears herself against Jason's nose until a second one rises to take its place. The women in the doorway are speechless. As Miranda's screams weaken she pushes Jason to lie flat on the ground and the onlooking mothers think she is finished but in fact she has only done this to trap his head between her thighs and continues grinding for another minute or two until she is finally satiated.

When she stands she feels like a new woman, an Amazon, unashamed of anything. Some cum which had been deep in her womb is finally shaken out and she feels its coolness leaving her.

Her anger with her mother has passed, but she is still furious with Jason.

"She points to the final trickle of semen and raises her eyebrow, "Are you going to finish that?"

Age 24

Miranda is still wearing her wedding dress when she enters the room, but Tom is in nothing but his cage and tied down tightly to the bed. Men actually learn in school how to restrain themselves without the help of a partner. Such a task is much easier to accomplish with handcuffs, and a pair was already hanging from the nuptial bed when they arrived in the hotel.

"Comfy?" Miranda asks.

"Yes." Tom gulps, nervous and excited.

Following a trend of successful women marrying younger and younger men, Tom is only a year removed from high school. Miranda finds his nervous jitters endearing.

"Let's get you out of there big boy." Miranda straddles his lower body and unlocks his cage with a practiced hand.

"God I have been thinking of teasing this piece of meat all day long." She admires his slowly engorging member as Tom shifts nervously under her hand.

"And I've been fantasizing about being inside of you for months." Tom adds.

"Wait, what?" Miranda is taken aback.

"Well, it's our wedding night." Tom sounds suddenly panicked. "You know, so I've just been looking forward to finding out what it feels like to... to fuck you."

"Baby, I thought you knew. I've tried old-fashioned sex and it didn't do anything for me. We're not going to be doing that."

If Miranda had been plotting to spring this upon him she gives no indication of it. Her face carries only the look of concern and pity.

"I guess I thought maybe it would be different with me."

"Why would it be different? Do you think your penis is special?" She moves it around with pinched fingers like she is looking for some sign of uniqueness. "Did you think it was bigger than the toys I played with in the past?"

"I don't want to think about your past partners," Tom says.

"Oh I'm sorry baby. I thought maybe you kind of liked me teasing you - judging from how hard you get in my hand."

She may be right but Tom looks away, refusing to admit it.

"Well if it makes you feel better, I never enjoyed it. That kind of intercourse always made me uncomfortable. Even my best partners became so selfish. They just wanted to cream my pussy as fast as possible and then forget about me afterward."