The Cocksitter's Club- 1

(This is a short story that takes place in my 'Steel World' universe, broken up into 4 parts.  It is also required reading for students of my "Writing Better Femdom Fiction" class, lessons 1 and 2.  Enjoy!)

The smiling teenaged girl stood by the front door, notepad and pen at the ready.

"And when's his bedtime?"

The mid-thirties woman rolling her suitcase down the hall stopped to put on a light jacket.

"Oh, I don't know, nine, ten. Whatever's the standard nowadays."

"Nine it is," the teen giggled, writing it down. That her cut-off tee bared her flat belly and her jeans seemed painted on her curvy legs were not lost on her new charge, sneaking peeks at her from the living room. The girl winked at him as she asked: "And is he allowed any sugar after dinner?"

"I've been trying to get Robert to lose a few pounds for years!" the woman laughed. "If you can get him down to just one slice of cake a day, I'll double your tip!"

The teen smiled.  

"I've had lots of experience instilling discipline, Mrs. Lewen! I bet I'll have Robert doing push-ups and running a mile a day by the time you're back!" she said, smiling at him before turning back to the older woman. "Oh, and if I need to relax him before bed, is he allowed to look at any sexy images? And if so is he allowed full nudity, or just PG-13?"

"I don't need a babysitter!" Mr. Lewen roared, stamping his foot. "I'm forty-two for god's sake!"

His wife smiled, fingering the gold chain around her neck. "Robert, would you rather I leave this little key in a lock box at some other bank while I'm gone for a month? I bet Sharon over at First National would just love to have you come begging her for relief!"

Robert clamped his mouth shut, even as the hardened steel cage around his cock seemed to grow just a little bit tighter. The wife laughed at her suddenly subdued husband.

“No pornography for him, Lori,” she told the sitter. “But you may read him a bedtime story if you like.”

The young girl laughed as well. "I've got the perfect one, Mrs. L. That reminds me- what's his normal release schedule? I wouldn't want to forget the whole reason I'm here!"

"I usually let 'little Robert' out for playtime every three to four days,” Mrs. Lewen chuckled, opening the front door to spot the waiting taxi. “But if he gets release depends on how his attitude has been. Once I locked him back up without any relief at all, so he's gone a whole week without cumming!"

The girl hid her smile behind her hand. "Oohhh. A whole week!"

"I know, it's harsh," Mrs. Lewen said, missing the sarcasm as she hurried down the steps with her luggage. "But sometimes I feel that's necessary, just to teach his ego a lesson. Use your best judgement, dear."

And then Robert watched his loving wife unclasp her necklace and hand the only key to his government-mandated, inescapable chastity belt to a giggling teen girl he had never met before.

"Don't worry, Mrs. Lewen!" Lori laughed, putting the chain around her own neck and making sure that Robert saw the small key nestle between her budding breasts. "I’m an official member of the Cocksitters Club! You can count on me to keep him on his toes while you're gone!"

"Thank you dear," Martha said, giving the babysitter air kisses as she stepped into the cab. "Now I can enjoy my vacation without worrying! Kisses Robert!" she yelled at the blushing man still standing in his doorway. "Be good for Lori!"

Robert swallowed as the teen waved after the departing cab, then turned and skipped back up the steps to him.

"Now, Robert," she said, closing the door, "we're not going to have any problems this month are we? Are you and I going to get along, even though I hold the key to your wee-wee?"

Her tone was one a grown woman would use on a schoolchild.

"Now look here, young lady! I am forty two years old! I am the executive vice president of the third largest bank in this city, and I will not be ordered around my own home by some teenage girl! Now give me that key and you can go right on home. I'll see that you still get your full payment at the end of this month."

Robert drew up to his full height and stuck out his hand with a glower that had closed multi-million dollar mergers in record time and sent lesser executives running from his office in terror.

The eighteen year old girl just broke out into laughs.

"Oh, you are so cute! You're going to be a fun one, Mr. Lewen!" she said, walking right by him to plop down on his couch and turn on the TV.

Robert stomped in front of the couch and turned the TV off again.

"I'm not kidding, young lady! Give me that key, right now, and I'll tell my wife you were the best house-sitter ever. And I'll even double your tip! But if you refuse, I'll call Martha right now and tell her to fire you, and you'll get nothing!"

For a moment, she didn't speak, and Robert almost believed she was considering his offer.

The girl slipped out of her flip-flops to cross her bare feet on his handcrafted walnut coffee table.

"Four times my tip. Up front."

Robert balled his fists. This little teeny-bopper was shaking him down? The King of the Hostile Merger? But as he watched the way her fingers played with the tiny key around her neck, Robert had second thoughts.

"Fine! Four times! I've got some cash in a safe upstairs-"

"And you go on-line right now and give me a five star review. With a full paragraph description."

He ground his teeth. "Fine. Now hand over that-"

"And I want a new car. And a pony."

"What?!" he sputtered. "That's insane!"

"And I want a date with the lead singer of Soul Bomb. And a trip to the moon!" she giggled at the confused man. Lori picked up the remote and turned the TV back on. "Once a member of the Cocksitter's Club takes a chastity key, she only gives it back to the woman who handed it to her. Club rules. And there's nothing on earth you could offer me to change that."

Robert cursed and stormed off, feeling the weight of the steel belt around his tight, three-day-full balls with every step.

Lori called after him. "Oh, and order some pizza, could you? If I'm going to be here all night, I'm going to need some pizza!"

***

Robert broke down and ordered the pizza a half hour later.

He had reviewed his options, and they weren't great.

Martha didn't have a spare key as far as he knew. Ordering a replacement for a "lost" key would take almost three weeks at the Chastity Office downtown and required Martha's signature. And while Robert could probably just yank the key off the hundred and ten pound girl's neck, he couldn't stop her from crying assault to the police afterwards, and then he'd be in a much larger world of hurt.

He knew had to try and befriend this stupid babysitter. He couldn't go locked up for a month solid!

"Pizza's here," Robert growled, coming into the living room after paying the delivery boy. He swallowed. "And look, I'm sorry I yelled at you, earlier. It's just a big change for me. To go from thinking I'd be on my own this month, to suddenly being told that's not the case."

Lori laughed as she opened the box. "No problem, Mr. L! Most men I sit start off that way. But we all reach an understanding." She glanced at his crotch as she bit into a slice. "Eventually."

He swallowed, feeling the ring around his balls. "So, uh, would you like to eat here or in the kitchen?"

"Here's fine," she said, fighting to get all the cheese strands into her mouth as her attention turned back to the TV again.

She pulled up her legs to sit cross-legged on his couch and Robert tried not to think about how tight her jeans were around her toned legs- his belt was feeling too small for comfort already!

He coughed, then said, "So… this Babysitters Club you're part of-"

"Cocksitters Club," Lori corrected, eyes glued to the TV. "The Babysitters Club is something totally different."

"Sure, fine," he said, mentally rolling his eyes. "This club, how many girls are in it?"

"About seven right now."

How cute, he thought. "And does it have a president or anything? Who runs it?"

There had to be an adult in charge. Maybe someone he could make a deal with. Because if there was one thing Robert knew how to do, it was broker power deals.

"Oh, I do!" she said. "I started it about a year ago."

He groaned. This ditzy eighteen-year-old was in charge? Maybe he could call her mother to make a deal. But it wasn't looking good.

Lori rattled on. "It was because my mom was saying, how she had no one to watch my little brother when she flew to Chicago. Like, some normal young babysitter couldn't really help him with his... locked up parts you know?" she giggled, and Robert shifted uncomfortably in his seat.

He tried to adjust his pants to get more room. But the problem wasn't in the tailoring, it was in the steel below!

"I said just take the key with her," Lori continued, "but Mom was all like, 'Oh no! Bobby can't go two whole weeks in the cage, he'll go crazy!'" The teen rolled her eyes, then swallowed another bite of sausage. "So whatever, I told Mom I'd hold Bobby's key while she was gone and make sure his little hot dog got stretched every few days. And I'd be there with the key if a real emergency happened." Lori threw down her crust and started on a second piece. "Well, when Mom got back, she loved how well-mannered Bobby was compared to before, and I guess she told all her friends. In like two months I had more appointments than I could handle so poof- the Cock Sitter's Club was born!"

Robert's jaw was hanging open, his pizza untouched.

"But... he was your brother!"

Lori was totally focused on the TV. "So?"

"And you... helped him? With that?"

The girl finally turned away from the show, her cute nose wrinkled in confusion. "Huh? Oh no! I didn't help Bobby do that! Ick!" she giggled. When she shivered, her young, high breasts shook around his key, Robert noticed. "No, I just let him out of his cage when his balls got really blue, then put him back in afterwards! He never would have put it back on his own."

The man frowned, biting a suddenly tasteless piece of pizza. None of us would. Damn Universal Locking Laws!

But if she followed the same rules with him... being let out whenever he needed it, given time alone to have his fun (finally- by his own hand, at his own pace!), and then have this little hottie waiting to lock him back up... that didn't sound like too bad a month, Robert realized.

And it might be fun, to let her little teenage body figure in to some of his masturbatory fantasies. She had a girl-next-door innocence, but he could already imagine the little blond vixen nude at his feet, covered in baby oil...

It's not cheating if Martha hired her, he reasoned. Martha's was going to flirt with a few cute pool boys at the resort- she implied as much just yesterday! So a little fantasy for me is just as fair!

"So,” he said, swallowing, “how does this work? Do I just call you when I want to be let out, or...?"

"Well I can't just let you out whenever you want, or I might as well just leave you the key!" the teenager laughed. "Let's start with your normal release schedule and go from there. When's the last time you had a nice, big orgasm?"

He started to blush, having to lay out his sexual calendar to a girl less than half his age!

"Well, um, it's been three days since Martha... helped me in that way. So I'm actually due for a release today."

Lori laughed, crossing her bare ankles on the coffee table. “Somehow all the men I sit for say that! So just to be fair, we'll start the counter at zero from today, m'kay?"

And just like that, the orgasm Robert had been looking forward to for three days vanished.

"What?! You can't!"

"Calm down, Mr. Lewen. Or I'll make you wait until the end of the week," she giggled. "Your wife did say your chances for orgasm depended on your attitude."

Three more days! he thought, his full balls already painful in their iron ring. How am I going to make THAT?

"Oh, don't be such a Gloomy Gus," the teenager laughed, taking the pizza box into the kitchen. "We'll still have fun. There's a reason I've gotten a five-star rating from every male I've ever cocksat for!"

Watching her pert ass as she bent over to put the leftover pizza in the fridge, Robert could guess where those stars had come from. But even if she had a perfect ten rear, he vowed right then: he wasn't going to give her a good review unless she let him orgasm at a reasonable rate this month! In fact, if she didn't let him cum this week, he would go online and give her the worst review ever!

"So, what are we going to do all night, then?" he growled, arms crossed, when she returned. "I don't really have anything around here to entertain someone your age."

"You can watch TV for a few hours before bed if you want," she said, plopping back down and getting out her bookbag. "I've got algebra homework to do for tomorrow. Barf."

Robert saw his opening. His aching balls demanded he take it!

"You, uh, don't like math?"

Lori stuck her tongue out. "Ugh. Hate it. I don't even know why we have to take it!"

He swallowed. "You know, I could help you out with that."

She looked up as she was laying books on the table. "Are you sure you can do it? It's pretty hard stuff. It's Algebra II."

"Of course I can do it! I'm the vice president of a bank for goodness sakes! I’ve got twenty people working under me!”

She shrugged. “Okay, I guess we’ll give it a try.” She sidled up next to him on the couch, both of them facing the coffee table as she laid out her homework.

“See, this is what I mean!" she said, pointing at the first question. "Who even takes trains to Chicago any more? And if I wanted to know when the stupid train would get there, I could just Google it!"

Robert sighed, then started to explain the word problem to her. And the next one as well.

It wasn't a matter of intelligence, he soon realized. Lori was pretty sharp, when she wasn’t completely bored with the subject. So he kept breaking the problems down for her, while trying not to think about how the teen's firm leg was pressed against the side of his.

Or how easy it was to peek down her shirt to glimpse the tops of her lacy bra. Or the oh-so-fuckable way she bit her lower lip while he explained long division, or how he could see a hint of her panties over her perfect ass as she bent forward to look at the book while he covered factorials.

She's twenty years younger than you, he reminded himself, then snuck a look at her breasts again. Martha will have your balls if you touch her! Robert thought. Then he remembered.

She has them already.

And she gave them to his girl to hold.  For a month.

He couldn’t stop himself from imagining Lori holding his balls, licking the tip of his freed, iron hard cock with her cute pink tongue and glossy lips-

The pain from his surging cock made him double over.

"Mr. Lewen!” she giggled. “Is it making your little chastity belt tight, just from being this close to me?" But she didn’t move away.

He clutched his crotch in shame and pain. "No! It's... it was something else! It will… go away soon!"

She giggled again, and this time did move a little down the couch. “It’s too bad there’s no math thing for, like, how men get hornier and hornier the longer they stayed locked up or something. I’d learn that in a second!”

Robert was taking deep breaths, and the pain in his crotch was receding. Only at the barest erection did it not try to pull his balls off. He had told Martha that the Chastity Office had sized his belt too small, but she had never believed him!

When he could think again, he said, “Well, actually, there is something like that. At the bank we call it compounding interest.”

“Like, a math thing that tracks how something gets bigger over time?”

He gulped. “Yes. It’s the basis of how investing works. At first, the changes are small, but if the investor holds steady and lets the interest compound, over time the changes are quite impressive until-”

Lori whipped out a blank sheet of paper and practically pushed the pencil into his hand.

“Tell me tell me tell me!”

He did, and this time the girl was all ears.

He told her about interest rates, the rule of 72, and exponential growth. The actual exponential equations, however, he decided to leave for another day, even though she begged him to go on, pressed against his side.

“Lori,” he said, carefully moving a few inches away as his belt started get tight again, “I’d love to, but you just don’t have the math to go that far yet.”

“Well okay,” she said, putting her homework away. “But we’ve got a whole month for you to teach me!” She zipped up her bookbag and smiled at him. “You know, you’re pretty smart, for an older guy.”

“Thanks,” he laughed, taking one last good look at her ass as she turned to put the bag away, then pretending to look at the TV just before she turned to face him again.

“You’ve really got twenty people working for you?”

“Yep,” he said.

"Men and women?"

"Of course. Why?"

The teen snorted. "I could never work under a man. Just knowing that, right under his pants, he was wearing a tiny metal cage around his cock and he couldn't even get a boner unless some woman lets him? Don't all the women in your division like, break out into laughs when ever you give them an order?"

He started blushing immediately. The sudden turnabout made him feel about six inches tall. And worst of all, there was truth to it!

Jenny and Angela strut around my division like they own the place. It was never obvious enough to prove, but Robert knew: anytime he gave them an unpleasant task, they would make him pay with their outfits the next day! Those sharks in high heels and stockings were eying his job, and the pressure from his locked up balls was helping them!

He was still blushing when Lori looked at her watch.

"Oh my goodness- it's almost your bedtime! Run upstairs and get into your jammies- I'll be up in a second to tuck you in and read you a bedtime story."

Robert ground his teeth, jumping to his feet.

"Look, I'm a grown man! I don't have a 'bedtime', and I don't need a teenager to watch me during the night! You can go home know, and I'll call you if I want to see you again!"

"Mr. Lewen!" she laughed, crossing her legs and twirling a slim, bare foot in the air. "I'm cocksitting you all month. That means I'm staying here!" She pointed at the suitcase she had brought into the foyer from her car.

Robert groaned. This limber piece of jailbait was going to stay in his house? For an entire month? While he was under lock and key?

"What ever for?" he demanded. But with the pain of his cage crushing his balls, it came out more like a plea.

The cute teen gave him a smile. "In case you wuss out and need to beg me to unlock your little wee-wee in the middle of the night, of course!"

***

Robert thrashed and twisted in bed, his cage about to burst under the sheets.

His sexy cocksitter was sleeping just one room away, in what would have been his daughter's room if Emila hadn't been away at boarding school right now.

Just one room away...

What did that girl wearing to bed? A loose shirt and nylon shorts? A sleepshirt and tiny, cotton panties?

That thought made him clutch his cage. His cock was trying to grow out of all sides of the unyielding metal, threatening to pull his balls off his body!

Maybe she sleeps nude. Maybe he would get up for a glass of water at midnight and see Lori in the hallway, moonlit in all her nubile glory-

Robert bit his hand to keep from crying out, and rubbed his blue balls to soothe them. But his pride wouldn't let him call out to a teenage girl and beg her to unlock his cock, on their very first night together.

***

Robert was awoken before dawn, by Lori bursting into his room and pulling at his covers.

“Wakey wakey, Mr. L! It’s time for our morning run!”

He was barely awake, and the teen had his covers on the floor before he could react. He was thankful that he had worn sweatpants to bed.

Robert gripped his waistband with one hand and wiped his watery eyes with the other.

“Let me guess,” he said. “You were a cheerleader.”

“And the captain of the field hockey team!” she chirped, bouncing with energy in her tight workout shirt and tiny running shorts. “And one thing I learned from both, is that you gotta do your cardio first thing in the morning!”

He groaned, sitting up. “I think I’ll pass.”

“Come on Mister L! I promised Mrs. Lewen that I’d get you some exercise while she was away! My tip depends on it!”

“Yeah, but what did you promise me?” he said. “I don’t get less of a tip if you fail.”

The teen bit her lip for a second, and Robert tried not to think of how cute she looked in her tiny running shorts.

“We’re only going one mile to start, Mr. L,” she said. “And if you can keep up with me the whole way…I’ll shower with you when we get back.”

“What?!” he sputtered. He must have misheard!

“I’m not really a jock, I’m more of a princess,” she giggled. “But if you keep up with my slow butt for one little mile… when we get back to the house I’ll strip down and help you soap your back, wearing nothing but this key and a big smile!”

It couldn’t be possible! His cock started erecting, the cage pulling on his balls as it did.

“Lori! We can’t! I’m… I’m a married man!”

“So?” she giggled. “I said I’d still be wearing your key. That means you’d still be wearing your cage, so nothing can happen.” She bit her lower lip again, and there was something else in her eyes. “Your wife knows that I'm going to see you nude sometime this month. She was okay with it.”

He swallowed, hard. “And you’re okay with it? In my day, girls didn’t shower with strange men.”

“Well in my day,” she giggled, “all men’s cocks are locked up tight, so I don’t mind! What are you going to do, rape me with your tongue? Oh no!”

His cock was on fire, straining his cage away from his body and making his balls ache!

“Give me… a few minutes to get dressed.”

***

He fell behind in the first quarter mile.

Robert had been on the football team in high school, but that had been twenty years ago. Even with Lori’s incredible bouncing ass to pull him forward, his longer strides couldn’t keep up with her strong, quicker ones.

“See you back at home!” she laughed, pulling away easily at the half way point.

He was panting, drenched in sweat when he reached his house again, to find Lori waiting on his front steps.

“Too bad Mr. L- you can try to catch me again tomorrow!” she laughed, opening his door. “Now let's get you to the shower.”

He walked in with her, slowing as they went up the stairs. “You... don't have to go up with me,” he said.

“But that was our deal,” she giggled. “You get home first, you get to see me in the shower.” She opened the bathroom door and motioned inside. “But if I get home first... I get to see you!”

Robert gulped. “Come on, that's not fair...”

The teen sat on the bathroom counter, her bare legs crossed. “I'm sure you wouldn't have wanted to watch me shower if you won. You totally would have let me not pay up, right?”

He dithered, unsure.

Lori laughed and slapped the counter. “Come on, Mr. Lewen, I've got to get to school! The longer you stall, the smaller I'll think your wiener is!”

The man blushed, but did turn on the shower, testing the water with his hand. He slowly took off his shoes, then socks, and then shirt. Lori giggled. 

"And now for the big reveal."

He held his breath, and when he couldn't delay any more, quickly slid his shorts and underwear to the floor. Lori  immediately broke into laughs.

"I'm sorry!" she giggled. "They always look so small and helpless, all locked up like that! Look, your whole package can fit in my hand-”

“Lori!” he gasped, jumping into the shower, away from the laughing teenager's outstretched hand, before it closed around his too-small metal cage.

She smiled, swinging her bare feet as he started to shower, just a few feet from her. “You know, you don't look too bad naked. For an older guy.”

Robert's face turned beet red as he lathered his chest and back, knowing this giggling teenager was watching his every move through the clear shower door!

“Be sure to wash under your cage,” she giggled. “Or I'll have to help you.”

The thought of that little blond, snaking her fingers under his bars to tickle his nuts while she wore that tiny little running outfit-

“Please!” he begged as his dick surged, straining his cage and pulling his balls away from his body, right in front of her. “Can't you leave me alone?!”

She jumped off the counter. “Sheesh! Alright! I didn't know you were so sensitive,” she giggled, strutting to the door. She turned back to look at the embarrassed nude man one last time before she left. 

“I'll see you tonight after school!”

***