The Price of Admission Part 4

When Roberts finally returned a week later, we took things slow. He looked haggard, tired, even though he’d only been gone for two weeks total. His normally tight-fitting clothes looked a little baggy on his skinny frame. He was sitting on my stoop as I pulled into the driveway after work. I gave him tea and sandwiches. He didn’t say much, except to ask, in the sweetest, little voice, for me to remove his enforcer before he showered. I made dinner too, and when we went to bed, I touched him only to hold him close and cuddle.

He woke hard as iron, unconsciously rubbing against the bedsheets. With slender, delicate fingers, I teased his head while my other fingers raked softly through his hair. “Did you miss me?” I asked. When he gave me the right answer, I brought him to climax in seconds.

For the next few days he was very quiet. His youthful excitement had been dampened, I could see. Something in me felt guilty, though I don’t know why. It seems that my involvement, as slight as it was, burned in my head every time I looked at his expressionless face. I never meant for him to get hurt, not really, but of course I couldn’t tell him about my involvement now. It would only hurt our relationship with no benefit to anyone. There was no sense in lingering on the past, so I focused on the future. I took a few days off of work so that we could spend time together. I took him to the department store and spent hours dressing him up and showering him with compliments. As we shopped, I got into the cheerful spirit as well. I saw that a few well-chosen words of encouragement could shape his tastes twice as effectively as months of admonishment. I restrained myself, only buying him a few new outfits, but I realized that I could have his whole skater boy wardrobe in the trash in just a few months. That night I helped him cook dinner and the next morning I helped him clean the house. It wasn’t work I enjoyed, or felt obligated to perform, but spending time in his world seemed to make him happy. By mid-day he was back to his usual self, asking stupid questions, making silly jokes.

I took him out for a date that night, a proper date. Not to a fancy establishment where he would blush at the pretty waitresses, but a rustic-style smokehouse. Roberts felt more comfortable here, where he could make snide jokes about the trashy patrons and tell stories from his childhood. I guess his mom loved this sort of place even though his dad hated eating with his fingers. The more he talked, the more comfortable he became, until he was heatedly recounting all of his childhood fears and aspirations. He wanted to be an astronaut, I learned, and then after that a hair dresser. Eventually he settled on research assistant, but didn’t have the grades or drive for college. I realized that, for all my desire to shape and improve him, I had spent little time inside his head. In truth, he only wanted to be useful, like most boys. I couldn’t, and shouldn’t, continue this game of whack-a-mole, where I was trying to quash each of his pesky vices. I needed to work with his natural inclinations, use his wonder and naivette to both of our betterment.

When we got home, Roberts was flush with laughter and red meat. He was singing the songs he sang in choir, dancing around the room, whipping around the curtains, first like a sash on a beauty queen, then a bullfighter’s cape. “I am Fernanda, the fastest lance in the west,” he explained, whipping the curtain back and forth.

I gave him a look that startled him for a moment before he let out a giggle. I put my forefingers to my forehead and let out a snort, scraping the carpet with my feet. Him being behind the sofa, I had to vault the furniture to charge, hitting him in the middle with my shoulder as I wrapped my arms around him. The force drove him into the wall, where he let out an involuntary “oof.” I pulled him to the ground with my weight on top of him.

Roberts laughed, “You need to be careful. I just ate.”

I snorted again and licked his face. “I don’t do careful. I’m a bull,” I explained, my hand traveling the length of his body from his sensitive armpit to his more sensitive ass. I shifted a little to get my hand under my body, feeling for his already-hard cock trapped up against me. I felt it up and down. It wasn’t a large cock, or a wide one. In fact, it wasn’t particularly superlative in any way except for hardness. “I like it when you wear skirts for me,” I said. “They make your legs look great. And there’s easy access.” His panties were new too, with tight, snappy elastic and bright, vibrant colors. His partially freed cock pulsed in my hand. “Good boy,” I whispered. He closed his eyes and smiled.

I fished the pre-lubricated condom out of my pocket and pulled it over my fingers, my nails longer than what’s probably ideal, but it was too late now. I dragged the latex down his cock, over and under the scrotum, down his perineum, to the warm hole they wanted to invade. “Hey,” he breathed, but did nothing to stop me. He gasped when I entered him, his inflating ribcage outlined by his tight, clingy green shirt. I worked my fingers in and out, probing a little deeper each time, until I settled on a certain trajectory that brushed past his swelling prostate. He felt warm in my hand. “Oh!” he gasped when I rubbed his little prostate. “Nnng,” came from deeper in his throat.

“That’s good,” I told him, “you look so hot when I’m fingering you. I like how you move your body.”

He was breathing hard now, almost to the point of hyperventilation. His hips rose and fell with my fingers, his legs pulsing with the effort. And then, the most beautiful thing happened. A bead of clear liquid formed at the tip of his penis. Then some white joined it and the first bead dropped like a diver off the end of his pink head. Something deep in me melted watching that. It was just so incredibly hot. I couldn’t help but sink a hand down the front of my jeans as I kept up the pressure with my other hand. Sure enough, his cock kept going, sputtering out (not with much force) his lovely little boy cum. Roberts was now moaning audibly, driving his hips up and down such that I was barely moving my hand. “Good boy,” I exclaimed, “Very good.”

That night, when he fucked me, he lasted longer than ever before. His cock felt great for the first while, although, I was so wet that he was hardly making any friction. I rode him for a while, but after his cock slipped out for the third time, I just about lost my patience. Nor could he get me off when I leaned over the side of the bed and he stood on tip-toes. I could feel him trying to drive his cock deep into me, but his hips just bounced off my ass before he got very deep. Then the bitch had the temerity to slap my ass. I looked at him sternly. “You like that, baby,” he asked. His face fell a little and he broke my gaze to return to staring at my ass.

“That’s enough,” I told him. His little boner faded quickly as we sat on the edge of the bed. “You’re going back in chastity,” I announced, “but I just got the best idea.” I had him pay for it, although he had to take out debt from me. Only $50 or so, but it was still significant to the relationship. Now he had a contractual obligation to me. I picked out the dildo, an eight-incher with nice girth, plus a vibrating head. I got a second one too, but I paid for it. The second one was smaller, smaller than any of the toys I already owned. I even had Roberts explain to the woman at the register that he was buying a new cock to fuck his girlfriend because his wasn’t good enough. She seemed to understand.

“Get pretty for me,” I instructed as I made myself a drink. He made the right choice, the choice I hoped he’d make, and came back in his manliest pink skirt and sheer white crop top, all over black fishnets- both stockings and sleeves.  I could just imagine what his skater boy friends would think seeing him all dressed up like that. He had put on make-up too, some nice blush and lipstick. “You look gorgeous,” I told him, which seemed to make him happy. Next came the harness, which I helped him into, over the fishnets but under the skirt. His own small package tucked neatly into a pocket of the harness. Then I put the cock on. It was black and ribbed, probably twice the size of his own pitiful erection. “And now look,” I exclaimed, “you’re looking just like a man. Anyone who didn’t know you would think it’s your own.” The hanging cock tented his pink skirt in the most delicious way. “You want to get me ready, baby?” I asked, sitting in the living room and taking a sip of my drink. Roberts sat in front of me, big obedient eyes staring up into mine. “You can start with my feet.” I watched his skinny ass as he rubbed and the suckled on my feet, first the left and then the right. I was ready for his mouth, which he offered generously, sucking and licking my steaming sex greedily, lapping up my folds and suckling my button. As I’ve said, what he lacked in ability he made up for in enthusiasm. I had him sit in the chair as I straddled him, working the new toy inside, cold against my aching cunt, but only for a moment. Soon the dildo was glistening with Roberts’ spit and my own juices, sliding in and out of me with greater ease. This was what fucking is supposed to feel like. I lowered myself down slowly, with great determination, until my cunt was filled completely. “Yes,” I moaned, lips on Roberts’ ear, fingers holding tight to his hair. “Yes, that’s how I want it. Finally a proper fuck out of you.” He was thrusting with all the force of a timid doormouse, but I’ll be damned if it didn’t fill me up just the way it should. “Fuck, fuck,” I grinded up and down his abdomen, jamming my clit against his body as I rode the surrogate cock, listening to the hushed panting he made as I pushed the air from his lungs. “Harder, harder!” I insisted, for all the good it did me, but in the end, I brought myself to a pretty decent orgasm, the best I’d had with Roberts’ assistance.

When I was ready, I dismounted and pulled the cock from its holster. “Now it’s your turn,” I explained. Of course, naive dear he was, looked to his crotch. I shook my head, trying hard to suppress the smile. “You’re going to cum the way that I did,” I told him. “I’ll help.”

Roberts was suddenly serious, the playfulness gone from his tone. “I really d-d-uh-don’t please I de-duh-don’t want to d-d-do that. I’m not r-re-uh-really feeling-”

“Oh please, baby,” I insisted. “Please. It’s just so hot. I love watching you like that.”

His voice was low and desperate. “I don’t want to.”

“No fun,” I sighed. I took the harness off of him and inserted my own dildo anyway. When I pulled up the harness, the small dildo’s other end sank into my pussy, significantly smaller than the previous delight, but enough to get purchase inside of me. I walked around the room, admiring my new cock. I even gave it a stroke or two, which manipulated the other end in a most… interesting way. “Are you sure you don’t want this,” I asked, looking down at myself. “I mean, I look like a sex goddess. Look at me.” He looked, but his face did not change. “Okay, that’s fine,” I said. “That’s fine.”

“Are you still going to let me out?” he asked, meek as a schoolboy.

“Still?”

The Price of Admission Part 3

[Not sure why this part was so hard for me to write. I guess the story got kinda real. Anyway, this is a necessary step for what's coming next in the story. I hope you enjoy.]

Let me just take a moment to stress that my involvement in what comes next started and ended with a single phone call in which I asked Darla to take my boy out and scare him a little. Everything else was her doing.

She met him in an upscale restaurant downtown. He showed up in worn sneakers and jeans, presumably arriving by bus. If I know Darla, she probably wore something black, sheer, tight, and more than a little intimidating. She mentioned a spiked necklace and black lipstick. The two of them had met at work when she was trying to sort out why she wasn’t receiving her mail. She was unimpressed with him. At 22, Darla was much closer to his age than mine, and cute too. She barely stood five feet tall, actually shorter than Roberts, I think. I’d had a soft spot for her since she joined the agency. A short girl with as much sass as she could always win me over. Besides, her brown ringlets and button nose were just irresistible.

“I took the chance and ordered you a salad,” she explained, “in case you showed up.”

“What kind of salad?” Roberts wanted to know.

He wore a cute pair of shorts and a ¾ shirt that ended just above his navel. He hadn’t shaved properly and an obstreperous tendril of stubble extended from his waistline and curled around his navel. Darla thought it was indicative of his general bad hygiene. Apparently, he managed to steer the conversation to his childhood illnesses, least favorite dogs,  and favorite daytime dramas within the first twenty minutes. You’ve got to love a boy as oblivious as that. He clearly felt uncomfortable in such a classy establishment, especially wearing what he was, particularly being served by a woman. When she spilled a drink on him, he tried to clean himself, but she insisted on rubbing the soda into his tight shorts.

Darla drove him all over town, to a new club with a line halfway around the block, to an old bar with retro games, out for a quick bite—she insisted on picking up her friend, Shelly—then back to the clubs. I don’t actually know Shelly, but I hear she’s a tall woman, and not entirely fit. I guess her breasts and belly have a way of escaping her shirt once she gets moving. Darla didn’t drink much, so that she could drive, but she never missed an opportunity to buy Roberts one, and Roberts never said no. Shelly (already plenty drunk herself) redoubled the effort, going shot for shot with the boy.

“Body shots!” she insisted. “Take it from my cleavage. No hands!” When he got close, she smacked his face around with her chest, laughing uproariously when he made a face and backed off.

Roberts obviously knew what he was doing on the dance floor, swaying his hips seductively, backing his ass up when someone took up behind him, singing, shaking, writhing, and moaning. Darla said it was a treat to watch, even though she didn’t like to dance. Shelly was more than happy to take her place, her hands sliding along his skin, groping his nubile angles. During a particularly intense bump-and-grind, she got so hot and red that she had to stop and get a drink by herself, leaning over the bar as she fanned herself. In the absence of her touch, Roberts happily took over the groping himself, rubbing up and down the skinny frame beneath his clothes.

”He’s a slut,” Shelly noted to Darla.

They asked Roberts to take them back to his place. Apparently he had an out-of-town friend. As they drove, the night air blowing through the open windows gave a therapeutic, if not entirely desired, reprieve from the heat and sweat and heady scents of the writhing bodies of the club. The wind pulled the hot moisture from their hair and clothes. “How old did you say you were?” Shelly shouted back to Roberts over the loud music.

“Eighteen.”

The women tittered. “You look older,” said Shelly. “Like a grown man.”

“Let me see your hands,” she said a little while later, turning around to face him. “Wow! It’s so tiny.” She curled her much-longer digits over his fingers. “The other boys must be so jealous of your tight, little body.”

“Well, I guess s-uh-so. I don’t know. I never got tha-uh-that much attention in school.”

“Shut up!” insisted Shelly. “You’re so cute you don’t even know it. That’s so cute. I mean, I don’t want to be rude or anything, but believe me when I say that a lot of girls would want nothing more than an itty-bitty honey on their lap like you.” She shot him a smile, “Like me.”

The women helped him open all the windows of the house, letting in the cool night. Shelly produced a flask from somewhere deep in her purse and they set to talking sitting on a couple of sofas beside the open kitchen. Darla finally found something in common with him in the stacks of boxes around the room. “There’s no way that Shelly Harlot is better than Fierceness. Never. No superhero can beat the depth of character and constantly changing plots of Fierce. Female or male,” insisted Darla

“Fierce is such a boring choice. That’s like saying you’re into asian teen porn. So done already,” poo-pooed Roberts.

“Anyway,” Darla dismissed his opinion, “it’s just cool to meet a boy who likes comics. The whole community is a fish market, as you know. The hairy virgins scare off the normal boys.”

Roberts agreed,  safely removing from her hands off the first edition Shelly Harlot comic One. “But you know why that is, right? Who’s your favorite male superhero? Can you even name one?”

“I guess Alan Orangutan is kinda cool. I don’t know. They all just seem so manly, you know?”

“Exactly,” said Roberts. “It’s pretty boring when they’re all long-legged, shapely, toned Adonises whose only problem is which superwoman to fall in love with at the end.”

“I’m not into comics,” interjected Shelly, finishing off the flask with a long swig, “but I can do a cool magic trick. Check this out.” She pulled a length of cord from her purse and sitting next to Roberts, close. “I’ve been practicing this everywhere, on the bus and stuff. It’s very relaxing when your hands take over and you don’t have to think anymore. So if I do this,” she grabbed his wrists together in one of her hands and wrapped the rope around them a few times, “and then like his,” she tied some kind of knot in the middle, “then you will find you can’t take your hands apart. See?”

Roberts struggled a bit, rubbing his wrists together without any change in the rope. “Yeah,” he said. “I’m stuck.”

“Come on now,” Shelly pushed Roberts back into the cushion. “Try harder. Really try now.”

Roberts struggled a little more with no change.

“Come on now, if you do this...” she helped pull down on his hands the knot, rope, and all spooled off his wrists like thread. “Easy. You’re free.”

“That’s not really a magic trick,” complained Roberts. “That’s just tying a knot.”

“Anything is magic if the reveal is surprising enough,” Shelly responded. “Do you have anything else to drink?”

“There’s something in the fridge,” said Roberts, getting to his feel. After a couple of steps, he nearly broke his ankle in his tall, red heels.

“Careful now,” called Shelly, standing to join him. She touched him on the ankles as he steadied himself against the wall. Her finger traced this inside of his leg as she stood, drawing a shiver of energy up his spine.

“Hey now,” he cautioned.

“What?” asked Shelly. “You don’t want me touching you?”

He smiled at her over his shoulder, “You can look, but you can’t touch.”

Shelly laughed bitterly. “What? You’re not a frigid bitch, are you?”

Roberts returned with the beer. “Please don’t use that kind of language with me. Here’s your beer. It’s my last one, so I hope you like it.”

Shelly took the beer in silence, lips pursed, eyes smouldering.

Darla asked, “Out of curiosity, how much did that beer cost?”

“Dunno,” he said with a shrug as he sat down. “Probably a buck and a half. Why?”

“You want to know how much I spent on you tonight?”

“Umm, I’m not sure. That was very nice of you. Thank you.”

Darla smiled coldly. “I think that’s the first time you’ve thanked me all night.”

Shelly shifted so she sat beside Roberts. “Let me see your hands again,” she asked.

“I don’t know…” he said. “Darla, I hope I didn’t give you the wrong idea- Hey!”

Shelly, despite her apparent drunkenness, moved fast and effectively, snatching his wrists and binding them just as fast. “Don’t worry, it’s the same knot. You can pull loose whenever you want to,” she explained.

“Please, Shelly,” he complained, tugging on the rope. This time it wasn’t just tied around his wrists, but also around the heavy iron frame of the couch. “This isn’t funny.”

“I’m not a comedian. I’m a magician, remember. I think my next trick will be to make you appear grateful. Do you want to thank my friend again?”

Roberts tugged this way and that but the rope held him tight, hands uselessly locked together. “I really did-ah-didn’t mean to give you lay-ladies the wrong idea.”

Shelly asked, “What idea would that be? That you want more than our money?”

“Le-let’s just call it a night, shall w-we?” Roberts tried to laugh, eyes searching desperately for mercy in Shelly’s smile. ‘Ju-j-just-ah-just untie me and-uh-and we’ll talk. Okay?”

Shelly said, “You look comfortable as you are.”

Darla was on her feet, standing over Roberts on the couch, and her foot edged closer to his crotch as she spoke. “You got something to show us under there? What are we working with?”

Roberts was in rare form, gasping and shaking and stuttering like never before. “Now I would have t-tuh-ah-told you earlier, only I wasn’t… I didn’t… oh please don’t hurt me.”

When they had his pants off, they saw what he was talking about.

“Where’s the key?” demanded Shelly.

“Tha-uh-um-huh-um-that’s the th-thing. My ex-eh-uh-ex-girlfriend has it.”

Darla was disappointed too. In my defense, I didn’t think things would get this far. I thought it would be a casual humiliation on the curbside in front of anonymous onlookers. I never really thought they’d get his pants off. Maybe he was just a bigger slut than I gave him credit for.

Shelly sat close now, her mouth inches from his ear, her flowing body draped over his thin, shivering form, her chest against his back, his skin pulled tight by the angle of his tied hands. “You know, that isn’t the only way we can have fun,” she suggested. Roberts struggled at his rope with renewed intensity. “Hush, hush. Calm,” she cooed as she ran a finger down his side, around the back to his ass. Darla took up in front of him while Shelly pulled his hips up to a kneeling position on the couch. Shelly started to open up his ass with one finger, then two, using the lube from her bottomless purse. Darla shimmied up her skirt and down her thong and guided Roberts’ protesting face towards her ass.

“No pussy for you,” Darla cautioned. “You haven’t earned it. Just lick my ass.”

Shelly asked, “Where are your toys?” but it was too late, Roberts was already occupied. So she started searching herself, wandering through the darkened house until she found a bedroom, and in the bottom drawer of the dresser, a collection of toys including an impressively sized, pink vibrator complete with bulging veins down its surface. “Is this yours?” she asked, returning, but Roberts couldn’t look away with Darla’s hand on the back of his head. “You must be some kind of slut,” insisted Shelly as she lubed up the pink appendage. Roberts’ moans rose urgent and jagged, muffled between pleas for mercy. “Hush that trash,” Shelly cooed into his ear. “Say something nice. We’re making love after all.” Roberts didn’t have anything nice to say.

When the women had had their fun, Shelly pet Roberts’ hair, matted with sweat. She asked Darla, “How much did you spend?”

Darla was flushed and still bottomless, leaving stains on an armchair. In the end Roberts had indeed gotten a taste of her pussy, not the he had asked for it (willingly). “Huh?”

“On him. Tonight. How much was it?”

“Shit,” murmured Darla as she thought. “Close to a hundred bucks. Those downtown drinks are crazy.”

“A hundred bucks!” Shelly whistled. “Do you think you got your money’s worth out of him?”

“Not really.”

The Price of Admission Part 2

“How was it?” Roberts asked in a small voice.

“I thought you did well,” I said, getting up and putting on my black and floral, silk robe. “That was your first time, right?”

He nodded. His gangly limbs spread across the bed, his bright red cock shrinking back to its usual, unimpressive size. Across his white chest I had left my marks: raised red slashes and round red welts. They looked like footprints in fresh snow. “How did you like it?” I asked.

“It was, eh, was a little scary, at times. Um, but it was interesting. And fun.”

I walked around the room, opening windows and tidying the spots we had rolled, pushed, sprawled, and braced ourselves upon and through. I savored that particular sensation of silk sliding across my skin, especially after sex, especially in the cool night air. The stuffy smell of sex gave way to the crisp summer night air. In truth he hadn’t done all that well. When I first removed his chastity enforcer after our date, he came almost immediately. His penis skin could have been made of felt, it was so soft. Embarrassed, of course, he tried to make an awkward exit, but I instructed him to go make us a snack in the kitchen. Bless his heart, he made us grilled cheese in the waffle iron.

When his jumpy, mealy-mouthed chatter subsided, I made another move. He was eager if nothing else. Happy to follow instructions, happy to listen, but very little initiative, almost no passion. In short, he fucked not like a man but like a boy. Which, hey, that’s fair enough, sparkly new virgin that he was.

His eyes followed me as I moved around the room. I caught his gaze every now and then. “What?” I asked coquettishly. His look was intrigued but somewhat concerned. “I don’t know,” he said. “Some of it was kind of weird.”

“Like what?” I asked, sitting at the edge of the bed, letting the front of the kimono hang low and open below my breasts. He sat up with legs crossed like we did in kindergarten, his little dick retreating into itself. “I was doing what you asked,” he said softly, avoiding my gaze, “but you kept hurting me.”

I chuckled softly, gently, caressing the patchwork markings I’d left. “I wasn’t really hurting you,” I said, “it was just to turn you on. Get you going. None of them will be there in a couple hours.” Except the hickeys, which would probably bruise. I didn’t even want to see his back, where I did most of my clawing.

Roberts sort of pulled away and scooted to the other side of the bed where he let his legs hang down. “And I feel weird about the last thing.”

“The last thing?” I inquired. “Like when I was playing with your ass?”

He nodded, shoulder slumped in shame.

“Aw come on,” I said, crawling across the bed to him. I laid my head on his lap, right over his glistening member. “Lots of guys like it when I put something in there. I usually do more than a finger.”

“Well I didn’t like it,” he responded.

“Did it make you feel,” I bit his thigh, “violated?”

He jerked with a whimper of pain. “I don’t know. I guess so. It was just, mm, it was weird.”

I was on my knees, rubbing his back, my fingers bouncing across the furrows I’d left there. “Don’t feel bad. It’s just a normal part of sex. Do you want to know what I think?” He sort of sniffed and looked at me. “I think you actually liked it. I mean, you got way harder and you started humping me so much better. I thought it was great.”

“Do you mean that?” he asked, eyes searching for validation.

“Absolutely.”

Training a boy is like gardening. You can never create something totally new. You find your patch, with its overgrowths and twisting vines and you start to prune. A bit here, a bit there, you trim and cut back, and then you encourage growth and development. I could never have made Roberts into a total sissy if the sprouts weren’t already there. All I had to do was prune back the bravado and immaturity, the hang-ups and misgivings, and it was only a matter of letting his dependence and submissiveness grow. With a little love and constant caring, I could coax out the best parts of him, and start to mold the sissy I always wanted. Of course, it’s easy to talk about in the abstract. In reality, the process is never straightforward, as there are hidden snags and deep neuroses. Nor was I the only person making decisions here. Like it or not, Roberts could choose his own path in life, and at times it didn’t seem like he could be the person I wanted him to be.

School was over in a fall and Roberts had been so busy chasing skirts that he hadn’t planned properly. Since he wasn’t going to university and he didn’t have a job (well, he made pizzas), I found it necessary to step in. The first thing that had to go was his nasty shitbox car he had bought with pizza money. I couldn’t stand the embarrassment of having that thing outside of my house at night (never in the driveway because it leaked). But in order for him to give up the car, he had to have transportation from his home and job. So I moved him in with me and found him a job in my office, in the mail room. That way I could drive him in my nice Desrail, the shitbox could be retired, and I could keep tabs on his comings and goings. And yet, for all that forward progress, he still insisted on bringing his taped up, busted skateboard in the trunk. Sometimes his pack of “homies” would come by work and they’d skate around the industrial park on his lunch break. From what I could tell none of the others had jobs at all.

Donna from the mailroom came to my office in a huff less than a month later. My office boy sat her in an armchair in the visiting area of my office. Even though Donna was technically a few ranks below me, she held a similar administrative position in her department and I treated her with respect. “I know you like him, I get it, and it’s not the first favor I’ve done of this kind–hell, it’s not even the first of its kind I’ve done for you, but the boy is completely useless. I really–there’s nothing I can do. I can’t use him.”

“What’s wrong?” I asked, getting a coffee from my secretary for each of us.

“He don’t pay attention to anything. He sorts shit wrong. He delivers things to the wrong people because he’s not paying attention. Seriously, I tell him what to do and his eyes are completely vacant. There’s nothing going on in there.” Donna was already an anxious woman, but when she wore loose, flowing blouses, as she often did, and talked violently with her hands, she was a self-contained tropical storm of heaving waves, threatening to overwhelm you with her sea problems. She had a rosy pink nose and a blotchy complexion. You could just imagine the cartoon steam billowing out of her ears and nose.

I spoke low and slow to try and bring her down to my level. “I understand that you’re frustrated. I don’t want to make your life harder just so mine can be a bit easier. Is there anywhere else he could be useful?”

Donna shook her head, her chins following after, “I already have him working the dumbest, easiest job in the place. Literally all you have to do is pay attention. I wouldn’t trust him with anything else.”

“Is there another department, maybe?” I asked. Donna pondered on that while my secretary organized the papers on my desk. “Don’t mix up Dole with Dillow,” I reminded him.

“HR always needs paper pushers,” she suggested, “but that’s certainly more involved than sorting mail. I mean, can he even write? Sorry, that was rude, but really. You know, there’s always,” she glanced towards my secretary, specifically at his ass as he bend across the desk. I shook my head, starting to talk, but she beat me to it, “I know, you need someone competent. Me too.”

I realized that I would need to get more involved. This kid wasn’t just a mess sexually, he didn’t have his life together. I figured that if he couldn’t work like a man, he could still serve as a houseboy. In the confines of my house I could train him up before introducing him to the wild again. With young boys the fun is being able to mold them exactly how you like, but with that comes a responsibility to train them properly.

I had hoped my latest project would be somewhat self-sufficient, but it seems that his mother taught him nothing. I had to teach him each of the chores in a somewhat laborious process of leading him around by a leash and securing him in the area needing improvement. After an hour or so, I would check on progress and administer corporal punishment if necessary. I don’t personally take pleasure in inflicting pain, at least not the physical kind, so I didn’t really enjoy the process, and Roberts clearly wasn’t pleased either. The way he wailed, you would think he had never seen the flat side of a paddle before.

During this time our sex life changed a bit too. Roberts had so little in his life to lose, it was hard to find leverage to keep him acting right, so I found it necessary to institute certain rules. Early on, I let him cum in me twice or three times a week. I now instituted a rule that he would be allowed to have sex each week on Sunday if he was very good. Of course, for a youth of his age, only once a week is not often enough to prevent him hurting himself in the enforcer, so he was allowed four hours of personal release time per week that he could use whenever he wanted. From what I can tell, he was masturbating about once a day, which honestly wouldn’t bother me if he was getting his chores done. Unfortunately, he was not getting his chores done often.

“Can I have my release time yet?” he whined in that particular teenage way.

“Did you finish the dishes?” I asked, not looking up from my magazine.

He rolled his eyes. “I just cooked. Can’t I do them later?”

“No, you can do them now, and you can get release time later. That’s how it works, remember?”

He sort-of stomped off and huffed around the kitchen for a while. When he came back he was getting red in the face. I couldn’t help but notice how hilariously cute and tiny-sounding his stomping was. “I wish I’d never given you my key. I never had to deal with this from my mom!”

It was my turn to roll my eyes. “Maybe that’s why you’re such a spoiled child. I mean, come on, Roberts. You’re an adult now and you’re throwing a tantrum like a baby.” That seemed to shut him up. On his way out of the room, I called to him, “Roberts, there’s a glass.” The wineglass sat on the table before me, so he had to walk all the way across the room and come right up to me to retrieve it. We had a strict ‘no male clothing’ rule in the house, so he opted to wear nothing. I resisted the urge to tug on his little cage or slap his ass as he walked by. “Thank you,” I said when he picked up the glass. He only glowered at me.

I heard the glass on the kitchen counter, but instead of the sound of water running, I heard the pad of his feet across the hardwood of the front room, up the stone stairs and the closing of the bedroom door. I didn’t let his disobedience bother me, I just kept reading.

When he returned about a half hour later he went straight to the kitchen and started washing. I came in behind him and found him wearing my favorite of his panties, a pink lacy number that showed off his tight ass in the best light. “How was your break?” I asked.

“Huh?” he asked, eyes all wide and innocent.

“What were you doing up there?”

He looked back at the dishes and said noncommittally, “Cleaning.”

I could have laughed if I wasn’t so annoyed. “And what did you clean?” I asked.

“You know. Made the bedroom look nice.”

I was right behind him now, watching his washing over his shoulder. I felt the outline of the panties, two bands across each ass cheek, meeting in the middle and sliding down, all the way around his pert ass, up that warm crease between his legs. I grabbed his balls lightly and kneaded them around. “Are your guys feeling sore? You didn’t get any release yesterday, did you? Why was that?”

“I was bad,” he muttered.

I removed the panties, sliding them down slowly and lifting his feet out of them. Finally I caught a glimpse of his caged package. “And what the fuck happened here?” I demanded. His enforcer was all fucked up. His balls glistened with lube where he had slid it off without the key, and his cock was not at all seated in the plastic tube. I always made sure his enforcer was properly installed every morning, and this was not my handiwork. “Seriously, answer me, what is going on?”

“Well, I asked first,” he said, lower lip jutting defiantly.

“This is absurd,” I said, giving his balls a hard slap. “This is ridiculous. You’re like a child. Just an annoying little shit. I’m too old for this shit. You’re not serious about this relationship.”

Things went downhill from there. As soon as I threatened to throw him out, suddenly he was singing a different tune. Suddenly he loved me and needed me and please please how will I live, where will I sleep, etc. His sniveling only annoyed me. By the end he was sobbing.

“Just hush. Please. Just shut up your bullshit and get out of my house. You don’t live here anymore. To live here, you need to make your own money, or you can work for me. You don’t get to laze around all day and then disobey me at night.”

Eventually he gave up protesting and made up his mind. “That’s fine,” he told me, one bag of clothes under his arm, his panties clearly showing through his tights. “You think you’re so great. Women would love to be with me. I could find someone else in a week.”

Somehow he didn’t find it suspicious that he did just that.

The Price Of Admission Part 1

“Roberts,” he corrected me, mid-sentence.

“Excuse me?”

“My name,” he said. “It’s Roberts, not Robert.”

“Oh.” I smiled politely, thinking of the things his tongue could be doing instead of arguing with me. “As I was saying, Roberts,” I started again, putting enough emphasis on the maligned consonant as I could without giving in to outright sarcasm, “I can’t think of a job that a man can do which a woman can’t, but there are plenty of jobs that a woman can do that no man can.”

Roberts was getting flustered, in a cute way. His neck up to the ears had flushed and his casual stream of, “uh, and, like I was, uh, saying,” had progressed to an outright stammer. “There’s all kinds of th-th-uh-th-uh-things that men can do b-be-be-uh-best. There’s teaching and all kinds of, uh, social work, and, uh…”

“And coat checks,” I suggested, “and I’ve never gotten a proper boot shine at a show from a woman. But you’d never want to guy pilot. Or rocket scientist. Right? The last thing we need is a male driver behind the wheel of a multi-billion dollar machine,” I insisted to general agreement and laughter. Roberts pulled down the fringe of his short, white shorts, attracting the eyes he’d hoped to avoid. Stacy caught my eye with a knowing nod. I tried to communicate “back the fuck off” with my eyes, but was unsure if I succeeded.

Roberts’ girlfriend tried to ease the tension, “Now that’s not entirely fair. There are some great male racing drivers. They say guys can focus on one task more intensely than we can.”

“Yeah, focused. That’s what they say about guys,” I chortled. “Dogs are focused too until a steak enters the room.”

The girlfriend, Carley I think (or Charleigh or Karley or somesuch nonsense) was no competition for me, any woman of the table could see. She was just a girl, and a naive one at that. Earlier she told us that Roberts wouldn’t give her his key until she put out for him. Her doughy body and passive attitude would never hold his attention for long. What he needed was a stern hand to encourage his manly nature and punish his womanly pretentions. Carley was only in town for a few weeks and was staying with her aunt, my friend, Stacy, until spring break was over. Stacy had plenty of time to make a move on Roberts, but she would never be brazen enough to attempt it with her husband Tom always around.

With the last few drinks finished and the conversation wound down (with neither sex having been declared superior), we moved the party back to Stacy’s house, where there was a pool table, a pool, and cheaper liquor.

After a drink and maybe another, we convinced the boys into a few games of strip pool. The first game went quickly, with only a couple of socks and Tom’s tie discarded, so we made it more interesting. “Once you miss a shot, you lose clothing for every sank ball until you sink again,” I suggested. For a while only Tom was disrobing, his protuberant belly hanging low over his waistline and then his waistband. When his undies came off, he was hairy and pale, and we allowed him to put them back on. Carly was the next to lose her clothes, sitting pudgy, pale, and sad, overflowing her bar stool in a tightly-packed bra and underwear. It wasn’t until the last few rounds that Roberts started missing. My turn followed his.

“I’m going to make you regret that,” I said devilishly as his solid ball bounced harmlessly off a bumper, not even close to the hole. With my first strike, his shawl came off. Even though the weather was warm, he had retrieved his shawl from the car. “That doesn’t count,” I insisted, but Carly and Stacy shouted me down. “Fine,” I accepted, and promptly sank two balls with my next hit. Off came his necklace (another questionable “clothing item”) and his shirt. Underneath was a pretty unimpressive chest, almost entirely free of hair, with two tiny cherry-drop nipples. As he walked around the table, I could see the flexing and relaxing of tight muscles under his pale skin. His tiny shorts left little to the imagination.

“Give us a twirl,” I shouted. Carly rolled her eyes, but Roberts didn’t look to her for permission, he looked at me. “Pah,” he powerlessly protested, and took a turn, quick and awkward. “Aw, come on,” I insisted, “give us some sugar,” and reluctantly he spun around again, slowly, letting me examine how the ridges of his scrawny lower back gave way to the ass cleft below. His was a small ass, but perky enough to fill in those tight little shorts.

Right on cue, Stacy dropped the straw with which she had been stirring her margarita. It just so happened to roll close to Roberts’ feet. “Sorry,” she said coyly, “could you get that?” Again, the boy looked not to his girlfriend, but to me, at the eyes he could feel burning into his skin. I gave a slight nod. Like a good boy, he bent to his feet, leaving his ass high, those wonderful shorts sliding slightly up, just enough to tantalize without satisfying. I find that a boy in a good pair of shorts can be more interesting than any nude. The suspense has its own allure, I suppose.

When Tom cleared his throat, I realized that it was still my turn. “I could clear this table,” I said, counting one, two, three balls left. “What are you going to lose if I get two more?” I asked. Roberts giggled and shrugged. “All I see are the shorts,” I said. Carly finally lost her patience and demanded, “just take the shot.” Dutifully I sank another ball, sending it speeding clear to the other side of the table before, luck beyond luck, it dropped into a pocket on my side of the table. I let out an evil laugh and Stacy shot me a chiding look. Had it been earlier in the night, or had we had a few fewer drinks, I might have controlled myself, but not tonight. “What ever will you do?” I asked as he dropped the shorts.

This was one of those rare cases where the reality was actually better than fantasy. Beneath his shorts he had a lovely see-through chastity enforcer, pressed tightly against his (maybe a little engorged) cock, a small tuft of pubic hair (although I prefer clean shaven, a cute design can be nice), and the most incredible skin. Most skinny white boys are too pale and their skin becomes translucent, red and blue with veins, but Roberts’ skin was white as porcelain and just as smooth. A little stubble was forming up in the corners of his pubic triangle, but that somehow seemed hot in a rugged kind of way. Almost immediately I wanted more. I started imagining the things I could do, the things he could do for me. To be honest, I imagined that perky white ass sliding down over my fattest purple cock, the look his face would make, the ripple of his muscles as he took my thrusting, the noises that whore mouth would make. The imagination reels. The things I could mold that body into…

Roberts sort-of half-covered his cute little package with one hand, a futile but manish gesture. “It’s still my turn,” I noted, circling the table to the boy’s side. I had worn the correct dress for pool, figuring that the night would end here, as it so often did. Stretching to reach the middle of the table, I knew Roberts was getting a look at my curves in full view of his helpless girlfriend. When I stood up from sinking the shot, a red flush had sprouted in the middle of his chest. “What should we bet this time?” I asked the room. I sat beside Carly on a low bench to implicate her as a co-conspirator. “What else can he bet?” I asked her. Carly eyed her boy like a slab of meat in a butcher. My first suggestion would of course be dares of a humiliating, penetrating nature, but I didn’t want to put our pudgy, young friend off. She hemmed and hawed for a time, eventually standing to examine him from other angles. Finally she asked, “Which pocket are you aiming for?”

Tom returned from the kitchen with fresh drinks for us all. “You’ll want a nip of that. For courage,” I advised Roberts. Only the eight ball remained of my targets, in a somewhat tricky spot, far from the cue. “Far end. Left,” I chose. Carly led Roberts’ to the pocket and delicately (he shied away at first, but she held tight) lifted his little enforcer with his tightly packed, clean-shaven balls over the edge and into the leather pocket. “What if he flinches?” I asked.

Roberts looked flustered and shot his girl a panicked, pleading gaze. “What do you want to do to him?” she asked.

“Ten smacks, does that sound fair?”

I lined up my shot carefully, studying the angle from the cue to the black ball, from the black ball to my pretty pink targets. His cock had shriveled in its cage as if to hide. With a crack I let loose, laying hard into the ball, which hit the eight and sent both barrelling harmlessly around the table, sending the remaining balls into chaos.

“There’s too damn many of your balls on the table,” I complained.

A few short turns later, Roberts asked permission to visit the little boys room. I caught him in the hallway on his way back. Casually I slapped his ass as we passed.

“Hey,” he complained. “Hands to yourself!”

“Oh?” I asked as I grabbed hold of him, slipping my slender fingers along the hard plastic of his enforcer, sliding back behind his balls. I squeezed the package, lightly crushing his man eggs against the hard plastic cock cage. “I can’t touch you? ‘Cause of that girl out there?” I demanded.

“She-she’s-uh, well she’s my girlfriend,” he stammered.

I scoffed. “she’s a silly young thing. Fun for an afternoon, maybe, but she can’t teach you like I can. How old are you?” I asked.

“Eighteen,” he replied, “just.”

The number alone turned me on. I practically licked my lips. I had dated young guys before, but never into the teens. Still in high school, I considered, or just graduated.

“You owe me, you know,” I said.

“What?”

“You owe me for that extra ball I sank. You think that was free?” I traced the ridge of the enforcer with my thumb, exploring his prison. “I want to see your clit uncaged.”

Roberts pulled away a bit but my grasp held him tight. “Please,” he whispered.

“Where’s your key?” I asked.

He looked down at himself, avoiding my gaze. “At home,” he admitted finally.

“Your girly friend doesn’t have it?” I clarified.

“No.”

“Good.” I gave him a little kiss on the shoulder where it met his neck. He stood about a head shorter than me, and when I stooped I knew he could see my black lace bra, about a size too small, working its magic. Now I pulled his little clit, bringing him to his tip-toes. “Does it hurt when I do that?” I asked. He whimpered submissively. “Very good, little kitty. I like you purring for me.” It was true, I was getting wet, warmness heating me from the inside. I wanted to press him flat against the wall and rub up against him, but I restrained myself. “Are you going to be a good boy and leave that tramp?” I asked. My index and middle fingers, wrapped around the back of his balls along the plastic enforcer, strayed backwards and upwards, across the short prickles of his stubbly skin, back to the wrinkly edges of his exposed hole. Already on his tip-toes, he struggled up and away from my touch, but had nowhere to go. I circled his hole with my index and gently probed the tensing muscle. “Have you ever taken a cock? A real woman’s cock?”

He shook his head and turned his face away. With my other hand I took his face and pulled it back to me, staring him down eye-to-eye. “I can make you feel good. How do you feel?”

“Scuh-uh-scared,” he whimpered.

“But a little turned on?”

He nodded.

“Good.”