Femdom Roulette

Here's a new game to play. I'm calling it Femdom Roulette.

Download link for images

Stats on the deck

Preview the images on imagefap

My Goddess has started graduate school in another state, so we have decided to make this a long-distance relationship for the moment. It also presented an opportunity for me to try longer stints in chastity. This game is a way for me to relieve some of that sexual tension while ratcheting up the femdom thinking and feeding my sub brain.

Here is how I am allowed to enjoy myself in the weeks between seeing my lady love. This is a compilation of 177 images of a semi- to totally-pornographic nature that sissies are allowed to view. It started out as 200 but some of those images were rejected by Goddess. She says I can earn them back through good behavior, so we will see. There are 0 nude women and 0 submissive or degraded women. However, there are many images of white guys in submission either to women or superior men. There are also a few self-shot boners just to infuriate sissies in chastity.

Here's how to play. Load the images into a slideshow where you can set the time and make sure it's random. I use Windows Media Center. Set the timer to 60 seconds. This is the only way I am allowed to look at porn. If I want to perv over some low necklines, I have to see a few sissy boys and a few big alpha dicks. Such is life for a sissy.

Now, not being able to touch my dick directly at any point, I can only masturbate the other way. For this game, I use 4 dildos of increasing size, 2 tapered plugs and 2 dildos. I start with the smallest one. If there is a woman on the screen, I am allowed to play any way I want. However, if an alpha male is on the screen, I need to either take the entire plug, or I have to keep the dildo moving the whole time. This can be arousing for 1 minute, but it can be downright excruciating if you get alpha after alpha coming up. If you see three alpha males in a row, it is time to move up to the next biggest toy. If the image shows someone licking feet or presenting feet to be licked, you must lick. In my case I suck on a different dildo for the duration of the minute.

Think of the images as a random number generator that tells you what to do for the minute. Also consider that the images are dependent events, meaning that the more "good" or "bad" images you see, the fewer of that type are left in the deck. So, a session might start with a lot of alpha males, but that means you get to perv on more women later on. Rolling 3 alphas in a row seems to happen every 20-30 mins which feels about right to me.

Because it's essentially a random event generator, the game can be modified to include any rules that turn you on. For example, sometimes instead of sucking cock for feet, I will have to suck every time there's a black person on screen, male or female. This leads to a much higher proportion of oral fixation, which makes it harder for me to concentrate, and sends me into sub space faster. You can use the stats link to determine the starting probability of any kind of start. I've compared a few percentages on the right. Let me know if you have an idea of any other handy percentages you'd like to see.

My biggest gripe with searching for femdom porn is all the other fetishes and shock porn I end up seeing in the course my search. There's also no good way to find a lot of non-nude women without coming across nude images too. Inevitably I am bound to see things that will break the mental world I like to create when writing and feeding the sub brain. This game makes sure that when I look up images, I have a consistent experience. I can also become desensitized to these images and starved of the nudity I crave, so the visual impact of Goddess will be even more mindblowing when I see her next. This is also an attempt to manage the Coolidge effect of viewing porn.

This is also a way to push my boundaries. I find when I'm doing physically painful or difficult things alone, it's hard for me to push past my own pain to really achieve sub space. Because there are set rules to using dildos to this game, I can end up in a situation where I have to continue fucking myself way longer than I would normally be able to. Because I am chained to the duration of the changes, I can really push my limits. The randomness is also deliciously difficult to handle. You could get an easy, lovely masturbation session, or a true punishment of pain. You come to appreciate just how long a minute is.

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.

Delta Gamma Delta Knows How to Party Part 1

“Come on, Peter, I want to go,” complained Eduardo in his high, fey voice. “We need to get to the party so that we can leave the party and come back. I’m so sick of partying.”

“Yeah, yeah. I’m working on it,” I said. I knew that Eduardo’s real voice wasn’t the lilting, lispy intonation he used around me but I never bothered to call him out on it. I guess it’s what girls like. Some girls, anyway.

“You’ve been messing with your hair for like 15 minutes, you little slut. I want to go.”

I hated it when he used words like “slut” as well, but that’s just how he was raised. One of those really conservative small towns on the eastern slope where they call men who seek pleasure sluts while they teach good little boys to be docile and obedient. I guess that’s the value of college: to expose you to new people and new experiences.
“Fine. I guess I’m ready,” I said, pulling on my tall skinny heels. They were hard to walk in but I’ll be damned if it didn’t give me the best ass on campus. Well, second best maybe, I thought to myself, peering at Eduardo’s high, tight, small ass protruding like twin grapefruits under the tight spandex of his dress.  The number barely came down past his cage so the light would occasionally reflect off the metal between his legs as he moved around. “You better not bend down tonight,” I told him. “Everyone’s going to see your nasty pussy.”

“Oh shut up,” he said, slapping my chest. “You’re bad.”

Even perched on heels twice the size of his I kept my balance easily when he bumped into me. The boy couldn’t weigh more than 90 pounds. That’s why he was such fish bait.
I texted Amy that we were ready to be picked up but she said she was too drunk already, so we took the 105 across town. I felt a little silly under the harsh bus lights in my miniskirt and tube top. It was the same bus I rode to school and I would never wear this to school. I tugged on the pleats of my skirt and caught the wandering eye of a disheveled hobo. I made a shocked face but she only smiled wider and made an obscene gesture. I guess if I’m honest I’ll say I felt like a bit of a slut just then. Eduardo just kept joking and laughing, grabbing the pole for support when he lost his balance and then inevitably sliding around it in a half-joking way, checking to make sure the group of butch girls in the back were watching.

I felt better back in the dark. We approached Amy’s sorority house, Eduardo trotting clumsily to keep up with my strides. We could hear the bass from the end of the block. The house had some of the only lights on the block. This soro house dominated one of the closest streets to campus- nearly twice the size of any other house on the block. As was customary, most freshmen had gone home for the second weekend of the year, making the house a magnet for upperclassmen in the neighborhood. I texted ahead so Amy met us on the street out front.

‘’Well look at this pair of pretty boys,” she said, eyeing us up and down. I knew my skirt had ridden up on my hips while walking, but I trusted that my new cotton panties and the ring hooking the end of my chastity device to my perineum piercing would keep me relatively modest. I resisted the urge to tug on the skirt and appear nervous.
“Hi Amy,” I said politely. “Thanks for inviting us.”

“The pleasure is all mine,” she assured with a sinister grin.

I met Amy on move-in day. She and a few recruiters were talking to the girls about joining their sorority, and Amy had been nice enough to introduce herself to me. She instantly stood out as the most gorgeous girl in the room. Not a half-developed girl like my classmates, but a true woman. What a college lady should look like. Everything about her was cute: her nose, her brunette hair in a tight bob, her small, perky breasts (tastefully concealed under a white blouse and yellow collared shirt the first day. Tonight they looked amazing under a tight cotton tank top). Even her shoes were cute.  With only three or four inches on me, I could nearly look her even in the eye when I was talking. Despite that she had thirty pounds of womanly curves on me.

Eduardo giggled nervously. “Thanks,” he whispered.

Amy, who had been reclining on the long, wide stairs leading up the house got up and slinked around Eduardo, so close he could feel her warmth in the early autumn air. She moved gracefully, confidently, like a dancer. “Who’s your friend, Peter?” she asked.

“His name’s-“ I started.

Eduardo spun around awkwardly to face Amy, jutting out a hand, saying “Eduardo.” He tipped off balance for a second but steadied himself against her with his extended hand.

“Well hello,” she smirked, looking at the hand on her hip. “Let’s get to know each other a little first, Eduardo,” she said, stretching “Eduardo” out.

“Ed’s my roommate,” I said. “I hope you don’t mind he came along.”

“Not at all,” she said with a smile. “Well come with me inside. Let me get you guys drunk.”

Ed found his (annoying, annoying) voice for long enough to whine, “I need to get to work early tomorrow so I’m just going to have a little.”

Amy smiled over her shoulder. “Of course.” I detected sarcasm in her voice but Eduardo’s shit-eating grin showed no signs of comprehension.

Inside the place was packed. The music was blaring almost unbearably loud (“I got two boy toys getting on me like unh-huh”) so the three scurried to the kitchen. Looking around, I felt a funny twist of nervousness in my gut despite myself. There were so many gorgeous women in such a small space, all hot and sweaty from dancing and drinking, many grinding against each other. Men could never be totally safe in a space like this from weight alone. Any one woman could easily restrain me, let alone more than one of them acting together. I’d heard about the dangers of going to sorority houses alone (which is why I didn’t go last week) but I took some comfort in knowing that only bimbo sluts got raped in sorority houses. Of course I chided myself after for having the thought, but I was comforted nonetheless. On move-in day there was a presentation on how to protect yourself from rape and being drugged. Still, some part of my brain was alerting me that the situation felt dangerous. Or it could be a horniness pang. These girls were gorgeous. The prime of their lives. So many bodies. Warm, sweaty bodies. With warm, sweaty pussies grinding underneath.
“Shots!” yelled Amy. I flinched. It was much quieter in the kitchen, and her voice much louder.

We threw back shots of cheap vodka and passed around a sugary sport drink to wash out the taste. I reminded myself to keep an eye on Eduardo. If that kid got four drinks in him I’d be dragging him home on the bus or spending the night, and spending the night didn’t seem like a great option. There are distinct disadvantages to being a Small, I thought to myself just before a passing woman grabbed a quick handful of his ass.

Ed let out a yelp. “Another! Let’s do another shot.”

I hid my face in my hand. We took another shot.

“Another!” cried Ed but I threw my arms around him and said, “No, not just now. Let’s wait a bit, buddy.”

“You guys look cute together,” said a black girl behind us. Sandra, I think her name was. We also met briefly the other week.

Eduardo smiled at her briefly and then staggered wildly. I grabbed him to keep him up. “I think the shots hit me, Peter.”

“Yeah,” I said, smiling. I gave Sandra a polite smile and nod and shuffled off into the other room to find Ed a spot on the ratty sofa in the living room.  I yelled to two women sharing a conversation in the right and middle seats if they could move for my friend. They glared at me before continuing to talk. I asked the woman sitting on the left.

“Sure,” she said, getting up. I eased Ed (plopped is probably more accurate) and climbed on to the arm of the sofa. Looking around, it dawned on me that we were the only boys here. Literally every person dancing was female. “Is your friend okay?” the woman, bending over me asked. She had nowhere to sit and she stood nearly a foot taller than me so she bent down to get her face near mine. I resisted the urge to look down her low cut purple tee and looked into her eyes.
“He’s fine. He’s just a pussy.”

She looked a little startled by my language for a moment but then asked, “Can I get you a drink. You want a beer?”

Hmm. Non-specific beer or probably-tainted punch? “No thanks, I’m good,” I said.

“You come to a party and you don’t drink? What’s up with that?” she demanded. She had a pretty face: large eyes, full lips, nice nose, but she looked truly spiteful with her face contorted in disgust.

I smiled to ease the tension, “Just finished a drink actually. I’m taking a break.”

She shook her head “no” and set off for the kitchen. In her absence four women inquired about Eduardo’s health. He gets all the looks.

The woman returned with two plastic cups full of punch. “Punch,” she said, handing me one.

I smiled again, having somewhat more difficulty than before. “No thanks, I don’t want any.”

“Okay,” she said, frowning, “suit yourself,” and put one cup on the floor behind me. “So who do you know here?”

“Amy,” I answered, looking for her in the crowd.

“Oh, Amy. She’s my ‘big sister’ in the house. She’s helping me become a full member.”

“You’re a freshman?” I asked in shock. She was built like a brick house. Not fat by any means, just big. Big arms, thick legs.

“Yeah, “ she responded, “but I’m like 25. They needed my help on the ranch for a few years. How old are you?”

“Eighteen,” I lied. Even Ed didn’t know I was 17. I don’t like having to explain that I skipped a grade because I’m smart. People don’t like a smart man.

“Wow,” she said. “That’s hot. Are you a virgin?”

“No,” I lied again. I certainly wasn’t an anal virgin, if that’s what she meant.

“So you’re unlocked?” she asked.

“No, I took the pledge,” I said. Males at the university were automatically enrolled in an extra 9 hours of ‘domesticity classes’ unless they took the chastity pledge and secured their penis in a school issued chastity device. The nurse at the clinic on campus fit them after the first assembly. I thought it was ridiculously sexist, having all of us men march past our classmates out onto the football field and into the gym lockers. The whole practice is absurd. Predicated on the idea that men are sexual animals who will wildly attack women on the street unless properly educated or restrained. Nevertheless, who has time for 9 more hours of class? And I heard the demonstration unit gets into some pretty humiliating and debasing lessons.

“Wow, neat,” she said, rubbing her nipple under her shirt as she nodded. She’s not being very subtle, I thought to myself. I glanced at Eduardo, whose eyes had closed. I smacked him on the leg as the girl asked, “what type of restraint?”

This was getting awfully personal, but I didn’t want to annoy her again or look like a prude so I said, “I’ve got a root piercing. I’ve had it since I was a kid so I’m pretty used to it now.” Ever since puberty, it seems, there was some plastic or metal hanging between my legs. Early high school was the worst because it seemed the crotch snake would puff up at anything but controlling erections got easier with age.

I could tell that she wanted to know more, but she held back for a second, perhaps picking up on my discomfort. After a bit she asked, “So what’s your major?”

“Oh, that old question. Everyone asks that. I’m a Lit major,” I lied again.

“Really? I’m a Lit major,” she said, excited. “Who do you have for Theory?”

I considered for a moment making up a name but instead told the truth. “I’m actually a Men’s Studies major with a focus on Literature.” My voice cracked on the first syllable.

She rolled her eyes briefly and turned to face the room.

“What?” I demanded.

“Nothing,” she said unsmiling. “What’s the world going to do with another Men’s Studies major?”

“Ha,” I said, unlaughing. “I bet you never hear that as a lit major.”

Now she looked at me, blinking without understanding.

I tried a different tact. “Do you know how many men made major contributions to history? There’s a huge wealth of history and knowledge that’s being lost to our society due to pure indifference. We need someone in this world to remember.”

Now she looked outright hostile. She stood straighter up, puffing out her chest and crossing her arms along the bottom of her breasts. “You’re not one of those uppity masculists, are you?”

“No, I…” I started, but she couldn’t hear me. I hopped to my feet, indignant. “No I am not a masculist,” I said, stressing each word equally. “I am just interested in men’s literature.” She snorted a bit at that. “And what’s funny about that?” I demanded. This wasn’t going great but the alcohol had burned my empty belly and now I had a fire inside. She was just being so… dismissive.

“Nothing,” she said, “we just don’t really study men’s literature in Lit classes. It’s not really of the same quality. It focuses mainly on domestic scenes. Boring, boring stuff. And usually tasteless.”

That last jab was probably at the so called “Equality Erotica” that had been filling sex shops recently, portraying unlocked men freely masturbating without any kind of keyholder. For a few months there had even been penetration scenes with unlocked men and women, but the new set of decency laws ended that. For once I actually agreed with a Gender Relations Committee. That sort of behavior is better kept behind closed doors.

“I’m not saying that men deserve equality. Far from it,” I said, “but you have to admit that there are vast inequities in society. I mean, look at this school alone. Incoming male students has dropped below 15% for the first time in half a century. Only 10% of the faculty is male. We make up over 30% of the population of the US.”

“Yeah, you were probably told that by the male teachers. I think most, if not all of them, are in Men’s Studies. “

“Yes,” I admitted.

She looked away lazily and then turned back to say, “You know, you bimbos show up with the prettiest faces and the tightest little asses, but you open your mouths and it’s all shit flowing out. That’s why the only good man is one slurping up my cunt,” before leaving for the kitchen.

I stood there shaking with rage for less than a minute before another voice asked me, “Hey you want this beer? I got an extra.”

“No,” I shouted, too loud even for the music. I got a few glances from the room.

“Hey, what’s up?” Amy asked, handing me the beer. Absentmindedly I took it.

“Nothing.” I said. “Just. Just some jerk. Shouldn’t waste my time on her.”

Amy shrugged. “Well, you know. People are people. Girls will be girls.”

“Girls will be girls” I repeated hollowly, taking a sip. When the bitter taste hit my tongue I realized I was drinking, but at that point it seemed silly to back out of the sip. When I finished my sip I set the cup on the ground behind me, careful to bend at the knees not the hips.

“So what do you think?”  she asked, raising her voice above the din, “Is Sigma Nu the hottest bunch of bitches on campus?”

I looked around at the expectant faces. “Damn right,” I yelled, not feeling the spirit at all.
“Damn right,” the crowd cheered and went back to dancing.

“Look, I think we’re going to get going. Ed’s not feeling well.”

We both looked at Eduardo who opened his eyes and blinked around for a bit before settling into an empty stare in front of him. He must have pre-gamed before I got home, I realized.

“Really?” she asked. “You just got here.”

“Yeah, I know. I’m sorry.”

She smiled that same flirty, sinister smile. “I thought we were going to have a fun night tonight.”

I sighed. I did feel a bit guilty. “Look, I’ll make it up to you. We can go out to lunch tomorrow and you can show me the city. How about that?

She took my hands in her much larger hands and stepped closer, jutting her chest in my face. She rocked back and forth slightly, swinging my arms locked in her hands. “If you want to go then how come you’re being such a flirty baby, huh?

I didn’t smile that time. I wiggled free of her and took a step back. Her eyes were surprised for a second, and then hurt. I knew I had hurt her pride. I knew it was time to go.

Part 2
Part 3