Sissified by Sandra Read online

  Sissified by Sandra:

  Feminized and Trained by my Mother-in-Law

  by K.C. Ripley

  Author's note: All characters depicted in sexual acts in this work of fiction are 18 years of age or older.

  Copyright © 2015 K.C. Ripley. All Rights Reserved.

  “I’m going away for the weekend,” Amber said, folding her panties and packing them neatly into her small pink suitcase.

  “Where?” I asked, standing against the frame in the bedroom doorway.

  “Mom asked me up to the beach house for the weekend,” she said. She walked over to me, draped her arms around my shoulders, and drew me in for a little kiss. “We’re probably just going to sit around, drink wine, and do some dumb little craft projects. You gonna be all right here by yourself?”

  I was actually going to be better than all right. The fourth installment in my favorite video game franchise had just been released. I could order pizza and play all weekend. That sounded goddamn fantastic.

  “I don’t know, Amber,” I said. “I’ll miss you, baby.”

  We’d been married just four months. As far as I could tell, things were going great. She’d always been really close to her mom, so nothing seemed weird. Amber was a manager at a financial services company. I was working a shitty telemarketing job, making a third what she was. But I wasn’t insecure about it. Her family was loaded as well. I just saw it as a fringe benefit to marrying her.

  “Aww,” she said. “That’s sweet.” She zipped up her bag and kissed me goodbye one more time. “What are you going to do around here?”

  “Probably clean up some,” I said, shrugging. “Finally get around to fixing the broken railing on the stairs.” I had no intention of doing anything but eating, drinking, and playing.

  “I don’t deserve you, Dennis,” she said. Before she closed the door behind her, she said: “I’ll call you when I get there.”

  We waved as she shut the door, and I was free.

  My plan was simple.

  To maximize play time, I’d order the pizza before heading to the store to buy the game. Then I’d pick it up on the way home. I’d change into sweatpants and a T-shirt, pop a can of beer, and be strafing down other idiots on-line before the sun went down.

  Only, when I got home with the pizza in one hand and the plastic bag with the game in it in the other, and juggled my keys out of my pocket, I noticed the front door was unlocked. Had I forgotten to lock it?

  Inside, I put the stuff down on the kitchen table, and jumped when I heard a voice from the living room, a husky female voice I didn’t recognize at first.

  “Hello, Dennis.”

  I turned and saw Sandra, my mother-in-law, sitting in my leather recliner, the one I’d planned to park myself in all weekend. Her sandy blonde hair was pulled back, and she wore a simple brown sweater over a white blouse, with a white skirt to match. Her legs were crossed, her hands folded on her knee, and she looked at me over her glasses, like a disapproving teacher.

  “Oh, hi Sandra,” I said. “Where’s Amber?” I looked around. This didn’t make sense.

  “She’s where she said she would be,” Sandra said. “Up at the beach house.”

  “Oh,” I said. “I thought—”

  “Yes, I know what you thought,” Sandra said. “That I was meeting her there. I met her for lunch today, and we had a nice, long talk.”

  “About what?”

  “You, mostly. About what a disappointment you’ve turned out to be.”

  “What are you talking—”

  “Do you love my daughter?”

  “What?” I asked. “What is this? Of course I do.”

  “If that’s true,” she said, “you’re going to learn how to start showing it. Amber gave me her house key. She’s going to spend the weekend at the beach house, and we’re going to spend the weekend together here.”

  What kind of weird shit was this? Sandra was a beautiful woman, an older version of the woman I married. Was she trying to seduce me? And was Amber okay with this?

  She let out a little laugh. “It’s not what you think, Dennis. I’m not interested in you in the slightest. I just want my daughter to be happy, and right now she’s not. Do you know why?”

  I furrowed my brow in confusion and just shook my head.

  “Because her new husband is lazy and inattentive,” Sandra said. “He’s barely contributing to the household, and he’s not doing shit around the house. And even all that might be okay, if he could at least please her in bed. But he can’t even do that.”

  “Okay,” I said, my voice starting to shake. “I don’t know what the hell is going on here, but I think you need to leave.”

  She didn’t move a muscle. “It’s okay, Dennis,” she said. “I’m here to help you, to train you to be a better husband. If you accept my help, you can stay with my daughter and keep all this. If you don’t, Amber will leave you. I know the people who own your company. You’ll lose your job. And then I’ll make it my personal mission to make sure you can’t find another job in this town.”

  “What the hell is this?” I asked. I didn’t know if she was crazy or serious. I’d always thought Bob, her husband, was the one with the money and connections, but maybe I’d been wrong. Was she really threatening me? Could she actually follow through?

  I took out my phone and pulled up the button to call Amber.

  “She won’t answer,” Sandra said. Sure enough, the phone rang and rang, only to finally go to voice mail.

  I put the phone down and decided to switch gears, play along, and see where that went.

  “Let’s say I agree,” I said. “What would happen?”

  Sandra raised her eyebrows. “I’d say your willingness to be open-minded is already a promising start. Then I’d tell you to come over here and pull out your cock so I can have a look.”

  “What?” I looked back at my phone, thought about calling again. Amber knew about this? My body betrayed me, though, as I felt myself stiffening, causing the front of my sweatpants to start to prop up.

  Sandra saw and laughed. “Good,” she said. “You’re warming to the idea. Get it nice and hard for me. My daughter deserves the best, and I haven’t even seen it yet.”

  Before I knew what I was doing, I found myself walking toward her. A little smile played on her face as I did so. Then I stopped in front of her and pulled down my sweatpants and boxers around my ankles. My cock was red and erect now, bobbing in front of Sandra’s face.

  She raised up her hand and grazed the back of her beige-painted nails along my shaft, sending a shiver down my spine.

  “It’s very nice,” Sandra said. “But in a good marriage, the husband’s cock is mostly superfluous.”

  With her other hand, she reached into her purse. I saw her take something out. Not knowing what was happening next, my first instinct was to pull back, to reach down and pull up my pants. This had gone far enough.

  But Sandra didn’t let me. With the hand near my cock, she struck out like a cobra and snatched my balls. I doubled over and grunted, reaching out.

  “Put your fucking hands behind your back,” she snapped. “Or so help me God, I’ll squeeze these little boys so hard they’ll pop like grapes.”

  The pain was too intense to do anything put blindly comply. I damn sure didn’t want to call her bluff. I put my hands behind my back.

  She smiled up at me and waved the device in her hand up at me. “This is a chastity device,” she said. “It’s also got a nice little built in zapper. You’re going to hold still like a good little boy while I put it on, aren’t you?”

  I grunted and nodded, the blood rushing to my face.

  She squeezed a little tighter. “That’s not good enough. Say it.”

  “Ye
ah,” I said, through gritted teeth.

  “Yes, Mommy Sandra,” she corrected.

  “Yes,” I said. “Mommy Sandra.”

  A fresh smile lit up her face. Then she relaxed the death grip on my balls and began to slide the rings of the metal cage over my softening cock. The cold metal made it soften even more.

  Her fingers moved nimbly, taking only a few minutes. She had clearly done this sort of thing before. With Amber’s dad? I didn’t know and couldn’t think straight enough to follow any line of thought. Finally she took a small lock out of her purse and snapped it into place. I saw she also now held a small clicker in her hand, like the kind attacked to a keyring for locking and unlocking a car.

  “That’s so much better,” she said. “Now step back and take off the rest of those hideous clothes.”

  When I didn’t immediately move, she pressed a button on the device. A hot jolt of pain hit my balls. I heard a loud zap and felt the pain bloom up into my stomach.

  “You still don’t get it yet,” she said. “When I say to do something, you don’t think about it. You don’t mull it over. You don’t hesitate. You fucking do it, instantly. Got it?”

  “Yes,” I said, then remembering. “Mommy Sandra.” I waddled back a couple of steps, my sweatpants still around my ankles. Then I took them all the way off, along with my shirt and shoes. I stood naked except for the heavy metal cage around my cock and balls.

  “When Amber gets back,” she said, “I’m going to give this to her.” She jangled the remote in her hand. “You’ll continue to address me as Mommy Sandra, but for the purposes of this weekend, I’m also Amber, your wife.”

  “Yes, Mommy Sandra,” I said. This was like some sort of bizarre nightmare. I could still smell the pizza sitting on the kitchen table. I’d gone from a normal life, a weekend of lounging around playing games, to this twisted encounter with my mother-in-law.

  “Good,” she said. “Now you’re ready to start learning how to be a good husband, not a piece of useless shit. We’ve got you locked and compliant, but the next step is to get your mind right. See, in a good marriage, the wife is in charge. Her needs, not your selfish little bullshit, is what’s most important. Along with locking up your little wiener there, we have to remind you that in the scheme of things, you’re just our little bitch.”

  I had no idea what she was talking about, but I didn’t like where this was going.

  “First you’re going to take a bath,” she said. “You’re going to get your skin nice and soft, and you’re going to shave all that ugly hair off your body. I’ve laid out a nice new outfit for you on the bed in there.” She nodded toward the bedroom. “That’s what you’ll be wearing around the house this weekend as you do your chores.”

  I thought about asking her what chores, but instead I just lowered my head and said, “Yes, Mommy Sandra.”

  “Good,” she said. “Now go pour that bath, and don’t make me say it again.”

  When I walked into the bedroom, I saw the outfit laid out on the bed. It was all pink satin and white lace, a maid’s outfit with a skirt and blouse. Six-inch pink high heels stood on the floor by the bed. She expected me to wear that? Dear God.

  I did what she said, though, pouring a hot bath and lowering myself into it. I shaved my legs, my balls, my ass, my back, and my chest. The tub was full of black hairs when I was done.

  “Hurry the fuck up!” Sandra yelled from the living room. I quickly drained the tub and used the shower to wash off. My skin was pink and raw from being shaved, nicked red in a couple of places, and I felt cold and vulnerable.

  When I came out of the bathroom, I gasped.

  Sandra stood there, arms crossed under her ample tits, harnessed in an open-cupped leather bra. She wore open-crotched leather panties and high black leather boots. She had a thin white rod in on hand.

  “Look,” she said. “We’ve got a lot to do and a relatively short amount of time to do it in. When I tell you to do something, you go as fast as you possibly can.”

  “Yes, Mommy Sandra,” I said.

  “Now put on your fucking clothes.”

  I trotted to the bed and looked down at the outfit, not sure what to put on first. I heard the whoosh of the rod from behind and the crack on my ass before I felt it half a second later. Then the sting bloomed across my ass. I instinctively grabbed my ass cheeks.

  “What the fuck did I just say?” Sandra said.

  I grabbed a pair of thigh-high white hose and began pulling them on my legs, moving so quickly I was afraid I’d rip them. Then I put on the skirt, then the blouse. Everything was tight.

  I paused before putting on the shoes and got another whack on the ass. Goddamn it hurt. I slid one foot into a high heel, then balancing, the other. Ten seconds into these shoes and my feet already hurt.

  Sandra smiled. “Not a bad start,” she said. “Just a few more touches before you get to work. Do you know where my daughter’s makeup case is?”

  I frowned. Didn’t she keep it in the bathroom? “I think so,” I said.

  “Do you or don’t you, dipshit?”

  I nodded.

  She just raised her eyebrows. Oh, right. She wanted me to get it.

  I wobbled back into the bathroom and found it under the sink, a baby blue tackle box.

  When I came back out, Sandra was holding a blonde wig.

  “Get on your knees, in front of the mirror,” she said.

  I knelt in facing the vanity mirror by the bed. I already felt ridiculous, but then Sandra pulled the blond wig over my head, and I was one step closer to looking like an actual woman.

  She pushed the makeup kit toward me with the toe of her boot.

  “You know how to put makeup on?” she asked.

  “No, Mommy Sandra,” I said. I mean, I didn’t think it would be that hard. I’d watched Amber plenty of times, but I was hoping maybe she’d give me a pass. No such luck.

  “Open the box,” she said. “We’ll apply the base first.”

  Then she walked me through it, standing over me and supervising every step. The base, then the blush. Mascara, eye liner. And finally, she made me find the brightest red lipstick in the box and slather it on my lips.

  When I saw myself transformed in the mirror, I couldn’t believe it. I actually looked pretty sexy, if cheap and whorish. As if she were reading my thoughts, Sandra gave a little laugh.

  “Pretty cute,” she said. “I’m sissying your ass up first so you get the message. Do you understand what the message is?”

  “I don’t know,” I said.

  “Of course you don’t,” she said. “Because you’re a dumb shit. This is to teach you the first lesson, that you’re the bitch in the household. Before, all you thought about was you and your little dicklet. But that’s locked up now, and so you can concentrate on making my little girl happy, the way she deserves. So say it. You’re Amber’s little bitch.”

  I still wondered if Amber even knew if this was going on, or if her mother had made all this up. While I was thinking this, and not repeating the words, I got another smack across the ass with that vicious plastic rod. I let out a yelp. Even through the satin skirt, the sting was unreal.

  “I’m Amber’s little bitch,” I said.

  Sandra straightened. She looked so powerful in that outfit. So goddamn sexy. They say you really should be worried about what your wife’s mother looks like, because that’s what she’s going to look like someday. I would have been fine with that. She had a few wrinkles around the eyes, but her body was still in great shape.

  “Well what do little bitches do?” she asked.

  “I don’t know,” I said.

  “Yes, you do.”

  I wracked my brain. “Whatever they’re told?”

  A big smile lit up her face then. “You might not be a lost cause after all,” she said. “Now then, starting with the kitchen, you’re going to clean the house. The whole house, from top to bottom. And this place better motherfucking shine.”

  “Yes, Momm
y Sandra.”

  “But before you get started on that, one more thing. You just got a makeover. You’re a brand new little bitch, so you need a brand new name. How about Denise?”

  I nodded my head. “Whatever you say, Mommy Sandra.”

  “Let’s try it out,” she said. “Give me a little curtsey and tell me your name.”

  I lifted up the hem of my skirt and dipped a little, almost losing my balance. I kept my head bowed. “My name is Denise,” I said. “It’s my pleasure to serve you.”

  She giggled and clapped her hands. “Great,” she said. “That’s fucking marvelous. “Now get the soap and sponges and get your dainty little ass to work.”

  I started in the kitchen, working my way from the top down. I dusted the top of the fridge and the shelves. I don’t think this had been done since we moved into the house. Climbing up high in heels was hard. I nearly fell twice. I got used to it, but my feet began to hurt even more.

  The makeup caked on my face felt hot, too. As I cleaned, I licked my lips, feeling the gooey, sticky red lipstick caked there. Sandra didn’t say I could drink, so I didn’t drink.

  While I cleaned and scrubbed, Sandra lounged on our sofa and watched movies on the Lifetime network. Occasionally I’d hear her giggle or gasp, and I wasn’t sure it was at the movie.

  After the first half hour or so she snapped her fingers. “Denise!” she yelled. “Get your pretty little ass in here.”

  I dropped the wet sponge on the floor and came as fast as I could on high heels. She lay back deep in the sofa cushions, her legs spread, her boots propped up on the coffee table. Her tits looked beautiful, high on her chest as she leaned back.

  “Get me some iced tea, bitch,” she said. “I’m thirsty.”

  “We don’t have any iced tea,” I said.

  “Do you have tea bags?”

  “I don’t know. I think so.”

  She sighed. “Well go check. If you have some, fucking make me some iced tea. If not, I guess you’ll have to run to the store.”