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Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha and I were used to being judged. Even in this day and age, it happened whenever we went out. We couldn't hold hands without heads turning. But her own family doing the judging? This was intimidating. Roxanne and Henry were coming to lunch. I had made burgers and fries, just a simple meal for a casual afternoon. I hoped that would be okay. Keisha and I had met at work, as couples often did. She was beautiful, tall and elegant, with a perfect smile. I was shorter, blond with scruffy hair. But we both loved movies, especially science fiction. We liked museums and walking and shopping. Keisha liked basketball - she had played at the University of Cincinnati; I had played a video game of basketball. So we had that in common. I wasn't looking for a black woman, particularly. She wasn't looking for a white guy. Oh, I liked tall women. If I had a type, that was it. I loved the assertiveness that athletes carried, the confidence. Keisha was almost six inches taller than I was. I hoped that wouldn't bother her parents. As white guys went, I was fairly white. Blond hair, fair skin. Nordic, almost. As black girls went, she was fairly black. Dark skin. Wonderful lips. Keisha sat out the crackers-and-cheese tray I had prepared. She let the brie breathe. She opened the wine. She put her arms around me. "Come here, sugar cube," she said. She leaned down and kissed me, hard, her full lips smothering mine. I looked into her eyes and felt my heart swell. "Sugar cube?" I asked. "White and sweet," she laughed. She kissed me again. "I almost said "marshmallow."' "Ugh," I said. "You can call me "fudge," she said. I made a face. "Sounds scatological," I said. She swatted me on the arm. I winced. Keisha was a strong girl. She had spent a thousand hours in the weight room. But it gave her that wonderful neck and those massive shoulders that I loved. Sue me. I think a strong woman is beautiful. The doorbell rang, and we opened it together. And there they were, this distinguished black couple. Henry and Roxanne. Henry was holding a bottle of wine. "How are you two doing,?" Roxanne embraced Keisha. I shook Henry's hand. Then Henry swallowed his daughter into his arms. Roxanne looked at me, smiled and opened her arms. Her embrace was warm, friendly. "Please," I said. "Have a seat." Roxanne sat. Henry stood and looked at me suspiciously "So you like a little dark meat?" he finally said. "Daddy!" Keisha cried out. "Slumming with the darkies?" he said. "Gonna buy you one or two? You probably hate our president." "Sir. I voted for Obama," I said. "Yeah. Out of guilt," he said. "Henry, you shush. He's just ribbing you, Julian. There are some white people he doesn't think should be flogged." She laughed. I smiled weakly. I sat in the chair next to Keisha. I felt perspiration on my brow. "So, Julian," Roxanne said, placing a slice of cheese on a Triscuit. "Did you make the food? Keisha tells me you cook." "A little, Mrs. Taylor. It's kind of a hobby of mine." "Well, you'll make someone a nice wife someday, won't he Keisha?" Keisha laughed. I blushed. "Keisha has a brother, Rashad. I don't think Rashad is dating anyone." I shifted uncomfortably. "Mrs. Taylor, I don't know what Keisha has told you about me, but I'm her boyfriend. I'm straight." She looked at me. Bit into her cracker. "Keisha, how is that nice Kathy girl. You two break up?" "Mom. You know we did. I'm dating Julian now." "So you go from dating a girl to dating a girly boy?" she said. "Is that it?" "No, momma," Keisha said. "Julian isn't a girly boy, not really. He's sweet." "Sweet? What kind of man is sweet? A candy-boi, that's what kind. Tell me. How big is his thing." "Momma, it doesn't matter. It isn't that big, but size isn't everything." What? They were talking about the size of my penis? Ten minutes in the door, and they had pronounced me a girly boy? "You'll have to forgive us," Henry was saying. "Black folks are direct when we talk to each other. Roxie here wasn't overjoyed when her daughter started chasing pussy, but at least we knew what she was. Now that she's giving up on girls and is dating fairy boys, we don't quite know what to think." "Sir, I'm not..." "Keisha. You got this boy into dresses yet?" Roxanne said. "No, momma. Not yet." Yet? "I know you, Keisha. You're a princess. You want someone to cook for you and clean for you. This little bitch boy is perfect for you. You'll have him in panties before dinnertime. No harm, Juliette. I just know my daughter. If you don't want to be her servant girl, then you better find you a nice white blonde girl." "Mrs. Taylor," I said. "No offense, but I love Keisha. We might end up married..." Keisha's head jerked around. "...I mean, we haven't talked about it. But I can't see myself without her. We're committed, the way people of different races have to be to work. And if Keisha is a princess, she's my princess." Keisha beamed. She took my hand and kissed the top of it, like a gallant knight kissing the hand of her fair maiden. I didn't like that, seeing as what Roxanne thought of me. But we had banded together. We had told them. We were a twosome. Nothing could break that up. Things calmed down a bit while we ate, but Roxanne kept asking me questions about furniture polish and floor wax, domestic problems aimed to take little digs at the fact I cleaned. It was obvious that Henry didn't do a lot of cleaning in his house. Like father, like daughter? Finally, the interrogation was over. It was time for Henry and Roxanne to leave. Roxanne took both of my hands in hers. "Juliette, please forgive me," she said, sweetly. "It's not your fault that you're gay. It's not your fault you fell in love with a user like my daughter." "But I'm not gay." She smiled again. "But you will be," she said. "And it's okay. The world needs simpering sissies, too. I can see it coming, Juliette. You're going to be such a pretty thing. I promise you this: I'll be there when you make some man his wife. I'll be in the church. Okay?" I shivered. "Roxanne, you'll be there in the church, because I'll be marrying your daughter." "We'll see, Juliette. We'll see." * * * I don't know if it was mentioning marriage, or if it was enduring her parents, or if it was just passion unleashed. But that might, Keisha was all over me. She held down my wrists on the bed, and whenever I moved one, she took it and put it back into the position it would have been in if it was tied up. She mounted me and ground herself against me. She bit my shoulder. Her ebony body hovered over mine, and her broad shoulders rippled in the moonlight. She ran her thumb and forefingers over my flat nipples and pinched them. She laughed, then put her lips onto them and sucked gently. She rode my penis like it was a rodeo. "Are you Juliette?" she whispered. "Are you my sissy?" We were playing , of course, so I moaned my assent. She was a force of nature, prodding, pushing, poking. She dangled her panties over my face and laughed. "My mom thinks you're a fag," she said. "She thinks you're going to suck my brother's dick. Are you going to suck my brother's dick? It's a good dick." I squirmed silently. Keisha liked to chatter during sex. But not like this, not with homosexual suggestions. "Keisha, is your brother gay?" I asked. "Rashad is ... open-minded," she said. "He did a stint at Jenson Correctional for selling pot. A white boy would've gotten a fine, that's it. But Rashad got three years. Three years is a long time for a guy to do without sex. As I understand it, there was a fucktoy on the ward. Yeah, I guess Rashad rode him a night or two. Why? You interested." "Funny," I said. Keisha's hands were on my lower back now. They traced their way to my cock, then around to my anus. They probed there, not too deep, because of her long nails. Just enough to tickle the rim. "You like?" she said. "It's ... okay," I said. "I want a toy," she said. "A toy?" "A sex toy. A vibrator. A butt plug. A dildo." "Keisha, I ... " "Who's in charge, Jules?" she said. "Remember. I'm in charge when we're in bed. You like me to be in charge." I looked up at her. That much was true. I loved her being on top, taking me, setting the rhythm. I loved her climbing onto my face and pushing me into the pinkness. It was the allure of a powerful woman with big arms and muscular calves. And now, she wanted to perform anal sex on me. More power, I supposed. More control. I pushed down against her finger. The nail cut me a bit, and I bit my lip. Was Roxanne right? Was I going to be her pussy? And why did that sound more like a promise than a threat? * * * The next day, I was still thinking about marriage, about walking my goddess up the aisles and claiming her forever. I asked Keisha if she had thought about it. "A little," she said. "But there is something you have to understand, sweetie. She's right, you know." I looked across the table and Keisha. She was smiling. There was some sort of glitter in her hair, and she magical. "I'm sorry?" I said. "Who's right? About what?" "Mom's right," she said. I swallowed. "She's right?" "About me. About the way I dominate my partners. I did it with Kathy, you know. She was my bitch. She proves you don't have to be a boy to be a sissy. Or a submissive, I guess, to be accurate. I pegged that slut all the time." I looked at my food. "I don't need to know about your lesbian lover," I said. "But you do," Keisha gushed. "Because you are Kathy! It occurred to me last night while you were licking me. I'm turning you into Kathy, and I can't stop." "But I love you." "And I love you. And I loved her. Sweetie, gender has nothing to do with the sexual dynamic. It has nothing to do with the clothes I put you in. It has nothing to do with the chores I demand of you. It has to do with control, with power. You wanted a powerful woman. Well, you have one. Welcome to me." I looked up. Keisha seemed out of focus. I was about to hyperventilate. "So you're breaking up with me," I said. "God no. I mean, I hope not. We're great together. But I'm ... different. Have you ever heard of a female-dominant relationship? That's what I want. I want to be the guy. I want you to be my girl. My Kathy. My sissy." This was wrong. A man does not stand for this. A man does not take orders how to live his life. A man is not a wimp. I bowed my head. "What do I do?" I said. * * * "There are so many steps to being a submissive," Keisha was saying, like she was giving a boardroom presentation. I thought she might break out the points at any time. "First of all, Juliette," she said, echoing her mother's name for me. "Don't think I'm turning you into a sissy. You're already a sissy. You already cook and keep the apartment clean. That's half the battle. "Secondly, you will remove your body hair. All of it except for your eyebrows and hair. You will use a depilatory and a razor for the parts that don't come off. "You will wear women's underwear. No, I know you aren't a transvestite by nature. But that's not the point. You will wear it because I demand it, because it will constantly remind you that you are submissive. You know, I've read a lot of sissy stories where the characters want to dress in girls' clothing so bad they forget who they belong to. But you're my faggot, not your own. So you will never be without a bra. And we'll start you on some pills that will give you something to put in there. "You will wear a dress. Not just any dress. You'll wear a maid's dress, a uniform, five days a week. You'll wear a regular dress the rest of the time to remind you that you aren't a man, not really. "You'll sleep in the spare bedroom. You'll get up in time to make my breakfast. You'll have assigned chores for each day: Laundry one day, shopping the next, the floors, the bathrooms. This is not a dress-up game. This is work. "You'll suck cock when I tell you. I know you aren't gay. But again, that's the point. Most boys who aren't gay can't stand the thought of what gay men do for each other. But you'll grow to love penis, the feel of it in your backside, in your throat. "I'll bind you. You'll be handcuffed. You'll be in a cock cage. I may spank you. I'll do whatever perverse thing interests me at the moment, ok. This will be my relationship. This is not a mutual decision. This is Keisha the puppet master. And Juliette just has to hang on for the ride." She sat back. She looked at me. She smiled. My mind was reeling. I should have walked out. I did not because I could not. I did not because, as she said, this had already started. I was already hers. How had her mother recognized that in me? That I was so weak, so soft, so compliant? That night, Keisha introduced me to her new toy. It was dildo connected to a panty, long and, of course, black. Her bbc, she laughed. She ran it over me fast, against my neck, down to my bottom. "Kiss it," she said, gripping it in her hands. I kissed it tentatively. "Aw, you can do better than that, sissy boy," she said. "Now put it in your mouth." I took the tip into my mouth. It had a cover that was supposed to be like flesh, but it still tasted like hard plastic. It felt large and intrusive, like the bottom of an umbrella. She moved it in and out, grinning, her eyes aflame with power. "Think about this in your ass," she whispered. "Think about it moving in and out, and jamming inside until it hurts. Think about how often you have shit back there that hurts. Well, this is longer and thicker. How do you think it will feel? How do you think a plug will feel? How do you think Rashad will feel?" I moaned. I couldn't help it. Anything. I would do anything Keisha asked. If she wanted me to bark like a dog, I would. If she wanted me to wear her collar in public places, I would. She wasn't mine. I was hers. * * * The wig was red and long, longer than my shoulders. Keisha kept pinning, poking, primping. She just could not get it right. My makeup was already affixed, dark red lipstick and lavender eyeliner. I looked like a strumpet. I was in a gray maid's dress - because she thought the black one was too formal - and silver stockings - because the fishnets were too whorish. I had on black low heels, just til I learned to walk in them. My boobs jutted out like blimps. What was it about a dress that was so effeminate? So many men in other cultures wore robes without feeling female. Hell, Scottish men once wore kilts, and they were amazingly macho. Have you ever seen Braveheart? Again, this was not for feminization, Keisha kept reminding me. It was for control. And so what if my penis had been erect since I had pulled the panties over it? She painted my nails lovingly, caressing my hand, coating each nail with long, loving strokes. Was it possible that she did love me? That this was just a part of her she could not control? I wasn't like one of those guys in the stories I had been reading. I wasn't inventing ways to get into a skirt. Nothing against any of those souls - a human hungers for what it needs. But this was another way of putting her foot to my neck. She could have had me dress like an astronaut, and the effect would have been the same. Except for the views you got from the public. I looked at the mirror. I looked silly. The dress was too short, the petticoats too flouncy. My hands looked big for a woman's. Something still wasn't right about the neck. My ass wasn't bouncy enough. And, of course, my boobs were fake. For now. I twirled and watched the skirt spin. The feeling was bittersweet. I felt awkward in a dress, but it felt thrilling, too. Erotic. Naughty. Keisha swatted me lightly on the fanny. "Do we have any chips? Any dip?" she said. "I want something before mother gets here. She always thinks I eat too much." I curtsied, not that she had told me to. It just seemed appropriate. I spread some Fritos onto a plate, and took some French onion dip. I poured her a Diet Soda and took it to the living room. She nodded. "Good girl, Juliette," she said. "I may marry you after all."' I lowered my eyes. I was still standing there when the doorbell rang. "Showtime!" she said. I went to the door. I took a deep breath. I opened it. Roxanne saw me and smiled. She was a pretty woman to be in her 50s, with wisps of gray just beginning to show. She nodded her approval at my dress. "Oh, Juliette don't you look marvelous," she walked in. "I knew you were a pansy boy all along. Didn't I say that, Keisha? You know, a lot of white boys are like that, not to be racist, but they all want to kiss a big black cock. Right, Juliette? You want a man?" "She kissed mine, momma," Keisha said. "Is that right, child? Practicing, are you? I'll bring my Rashad over to meet you. Now, that's a real man. You may never go back to girls." She cackled. I walked the women into the kitchen. I had salads and a baked chicken prepared for them with tall glasses of iced tea. "Juliette?" Keisha said. "Would you do me a favor? Would you stand on one foot." "One foot?" "Please." So I stood on one foot, my left foot balanced in the air, the heel hovering above the floor. There was no purpose to it, of course. It was just Keisha showing who was in charge. Wasn't it obvious? She was. Did I want this? Did I need it? Maybe a part of me did. I certainly needed Keisha and her strength, her power. She was a powerful light I could not help but stare into. As silly as it was, I would dress like a girl for that light. I would do chores. Later, I was washing dishes. They were sitting at the table, sipping tea, talking. "Do you really want this pussy boy,?" Roxanne was saying. "You proved he's a pussy. I get that. You established your will over him. You could make him your slave if you wanted, the way his ancestors did yours. Little Kunta-Kinte." Keisha shrugged. "I love him, momma. I do. I don't know if we can make a lifetime work, though, if he's my maid. I don't know how he would react to me and another man, or another woman. I don't know if he's the guy I want as the father of my kids. What are they going to say 'Daddy, your panties are showing."' " Roxanne laughed. "You may have to borrow some sperm from someone else anyway. His DNA has a flowered bow in it, I think." Keisha giggled. "And it's pushing a vacuum." "Yeah, you hate it when one of the sperms wants to suck off another one." It went on that way for a while, the two women amusing each other at my expense. And why wouldn't they? I was a fool. I was in a dress, with wig and heels. I had fake tits. I was wearing lipstick. And it occurred to me. Moments like these provided the humiliation that Keisha hungered to give. Not the moments when I felt pretty; the moments when I felt awkward. Not the minutes I felt like a girl; the moments I felt like an insufficient pretender. A tear rolled my cheek as I stood at the sink. I looked out into the darkness of the night. I had nowhere to go. I had never felt so alone. * * * I didn't know I was quitting my job at Computer World until it was done, until Keisha had told Trey Parker that I was leaving. For five years, I had worked for Trey, and although we weren't close, we had a casual aquaintance. But now he sat in our living room, trying to figure out what to make of this caricature in a dress in front of him. Parker had had workers who underwent sex changes - a lot of people did - so he knew how to direct them to Human Resources. But a sissy? Parker thought of a sissy meeting a customer. He shuddered. That would not do. And he didn't know how it might affect the workplace if that sissy worked in repairs. So when Keisha offered my resignation, he took it on the spot. It was better all around, he agreed. That way, I could go about being a maid. "What do you think, Trey?" Keisha said. "Do you think she has a nice ass." "Not as nice as yours, Keisha," he said. She smiled. "You white boys are all the same," she said. "You love the black chicks, don't you? You want to play in the jungle." "No, it's not like that..." "Of course it's like that. You were one of those little boys who liked Tarzan movies so you could check out the tribeswomen, right. You jerked off to Cleopatra Jones, didn't you?" "Look, I admit that black women are gorgeous." "Of course they are. Rianna and Beyonce and Tina Turner and Halle Berry. The list goes on." "Well, certainly, there are beautiful women of every color." "But the question is this: Do you like white sissies? Do you want to climb inside of Juliette's ass and live there?" "Well, I'm not gay..." "Who said anything about gay, Mr. Parker? I'm talking about taking your cock and putting into a human orifice. Wouldn't that feel good? Isn't sissy ass as sweet as female ass?" "Well, I wouldn't know." "Maybe you should find out. Juliette, take your panties off." I looked at her. She did not blink. So I pulled my panties down and stepped out of them. I felt Trey's hand on my buttcheek Then the other hand on the other cheek. Then he spread them. Then I felt his tongue dab at the rim. He pushed me over a chair until my head was knee-level. He rubbed oiil into my rectum. He entered me slowly. He was not particular large, but it still hurt. The ass is not designed as an on-ramp for incoming traffic. He fucked me, slowly, passionately, as Keisha looked on. This was my severance package, she would tell me later. This was my parting gift. I heard a flash. It was a camera click. As it turns out, Keisha had negotiated a very nice parting settlement from Computer World. She kept the money, of course. But the pictures would make sure the payments kept coming. And me? Coming once was enough. * * * It was the next Thursday when he came, unannounced. He was just there, in all his glory, leaning on the door, as cool as ice cream. Rashad. He looked me up and down. "So you're the sissy?" he said. "I heard that my sister owned one of you now. Why are there so many of you cock- suckers out there?" I lowered my eyes and opened the door for him. He laughed and walked past. "Keesh!" "Rah!" They embraced, siblings who had not seen each other in a while. Someone who didn't know might have seen the street in the embrace, the ex-con and former jock. But the truth is they were both middle income kids. They only thing either of them knew about the street was where to take a left turn. But who was I to talk? A pansy with a life of comfort behind him? A sissy maid placing coasters under soda glasses. "So, tell me about the pansy," Rashad said. "Juliette? She's sweet. Don't you think she's pretty? She wants to marry me." "Hah. She's a dyke? I would have thought she was a cock-sucker for sure." "You can do both!" Keisha said, grinning. "People are bi. You ought to know." "Hey!" Rashad said. "It's different inside. Inside, it's okay." "So you're telling me that you can look at that white ass and not want any of it?" Rashad look at me. "Well, it is a cute ass for a white boy," he said. "He'll suck you off." "You speaking for him, are you?" "I always speak for my sissy, Rah. You know that. His ass is mine. His mouth is mine. You want either one of them, you ask me." "Damn. I think I need me one of those. Maybe a bitch, though. I'd like a bitch sissy." "Guy sissies are better," Keisha said, sitting back. "You can't humiliate a girl sissy by putting her in a dress, or making her suck dick. They can eat pussy pretty good though." Rashad laughed. "Where you get to be such a mean bitch, Keisha," he said. "Momma wasn't like that. No one in our family was." She shrugged. "Sports, I guess," she said. "Some mean bitches on the court. You had to be strong, you know. I guess it just carried over." "I remember. You whipped their ass. Of course, now you whip this princess's ass." I hung my head. I lifted my chin. "Keisha. Can I speak to you? Her eyes widened, as if that was the most preposterous idea anyone had ever heard. She rolled her eyes to her brother and followed me into the kitchen. "Keisha...Mistress...Goddess. You know I am loyal to you, but please. I'm begging you. Don' t make me suck his cock. Please. I'll do anything. I'll scrub harder. I'll clean better. I'll be your sex toy. But not that." Her eyes were aflame, and her nostrils flared in anger. "You'll scrub harder because I'll tell you to," she said. "You'll be my sex toy because that's your fucking job, skank. And you'll suck whatever dick I tell you to when're I tell you. What's the matter? Is it too black for you? Too big? Is it this dick, or is it any dick? You white dicksucker! You pansy ass sissy!" I backed up, as if she had drawn her palm back. Tears rolled down my cheeks. Obviously, I had always known that Keisha had dark skin. But for the first time, I was seeing she could have a dark heart, too. I touched her arm, the black skin shining in the afternoon light. "Ma'am, think of where my tongue has been on you. Everywhere. This isn't race, I promise. It's ... homosexual. I don't want to do that." "You damn sure will, you faggot. And you'll beg me to do it again. Rashad's dick will be in your throat so much you'll think it's your tonsils. Queer!" I hung my head. I was crying harder now, sobbing, pleading. If I had ever doubted that I was a sissy, I couldn't any longer. Looking back, I suppose I could have simply left. But that seemed like a barrier I could not pass at the time. "You will get out there now, and you will get on your knees, and you will kiss his dick," she commanded. "NOW!" I left the room, still sniffling. I went up to Rashad on the coach. I sank to my knees. "What?" he said. I reached out and put my hand on his cock. It felt huge. I unzipped his pants, reached in and let it flop outward. Large, thick and uncut, it lay there. Prison penis. I inhaled. I looked at Keisha. And I surrendered. He was going commando, so there was plenty of freedom in his trousers. I took the bulb of it lightly into my lips. The skin there was lighter than the rest of it, which was dark and threatening as an adder. I cupped his balls, rubbing them gently. I looked him in the eye and bobbed my head, driving his head a bit deeper with every nod. It filled my mouth. I struggled to breathe until I found my rhythm. And then I was doing it. I was sucking a man's cock.His hands were on my temples now, guiding me, helping me with my pace. I could feel the veins along my tongue. I could feel the hair tickle my cheeks. My mouth was stretched wide for the girth of it. I glanced over, and Keisha's eyes were lit up from the power the moment provided. Her boyfriend was sucking her brother's dick, and she was delighted to have made it happen. She walked up behind me and slapped my bottom, hard. WHAP. Then again. WHAP. She shoved a finger into my ass and cackled when dryness stopped it. She forced it harder, then giggled when it stopped. "You're a black man's bitch now, white sissy," she whispered. "How does that feel? How do you like bbc? You'll get addicted, you know. You white girlies can't live without their bbc. I'm surprised anyone likes white dick anymore. They're all tiny and shriveled like yours. Only a real man has a dick like Rashad." I looked at her. Time was, she liked my penis. But as I knelt there in a dress and panties, that seemed long forgotten. She seemed into her brother so much I wondered about incest, but that was silly. Right? Rashad twitched and moaned, and the sperm shot out of him like a firehose. It hit the back of my throat on the fly. He was a gas pump! I struggled to swallow it all, and failed. He jerked, and forced my head down. He grew flaccid in my mouth. Finally, I let him slide out of it. I collapsed on the floor, the emotions overwhelming me. Keisha took a blanket at draped over me. "Sleep there, sissy," she whispered. "Sleep well. " * * * I woke up in the darkness in the middle of the night. There was sperm caked to my face. My makeup was smeared everywhere. I rose and went to the bathroom. I washed my face, then again. I turned on the shower. How did I get into this? The last normal thought I had, I was asking a girl to marry me. Now I was wearing dresses and panties. I had lost all of my dignity, all of my self-esteem. There was a satisfaction on Keisha's face that I would do anything to keep her. It didn't matter how far I had to degrade myself to do it. I went into the spare bedroom and got a fresh dress - dark blue - and fresh underwear - pink with ruffles. I looked over, and saw Rashad was sleeping there. I quickly gathered fresh petticoats and rushed to the hall bathroom. I checked my breasts, the same as I did every morning, then reached for my breast forms. I covered my head with my wig. I looked at the mirror. This was the me I had become. A mincing sissy boy. A submissive on bended knees. I wondered. If Keisha threw me out today, how would I dress tomorrow? Would I go back to male clothing? Could I? Would I go back to dating women? Could I? Would I put on lipstick in the morning? Would I wear earrings? Would I still look into the mirror to see how my hair had grown? My tits? I went to the kitchen. It was a little early to start cooking, but I put the coffee pot on. I sat and stared out the window.There were no answers in the darkness.There were only empty streets and unfulfilled tomorrows. There are people who are into bondage. People who are into golden showers. How do they handle the empty moments when they are about to devour you? I sipped at my coffee. It was strong and bitter. I had forgotten to sweeten it. I took another sip. I didn't deserve sweetness. * * * She arrived the next day at noon, quiet, unassuming. I would have known her anywhere by her chipped tooth and her button nose. Kathy. She was Keisha's first lover, the other K-girl. They had fallen in love when they played basketball together, Kathy, the cute little point guard, and Keisha, the demonic rebounder. The coaches had kept their love affair from the media, but everyone around the team knew about about it. Keisha had said it herself. I was Kathy. She had walked down this same hallway, had lived with this same shame. I opened the door and asked her in. Her eyes widened at my dress, and she almost laughed. Then she came in and sat. "This is about Keisha?" she said. "Actually, it's about me," I said. "I'm in love with Keisha, but I don't know if this lifestyle is going to be too much for me." Kathy looked me up and down. "Sissy?" she said. "Yes," I said. "A submissive sissy." "I was, too," Kathy said. "Keisha controlled everything. Our sex life. Our domestic life. Our friends. All of it. You know women can be submissive, too. Well, I was." I nodded. "Rashad?" she asked. Again, I nodded. I looked at the floor. "Handcuffs?" she asked. I shook my head. "Not yet," I said. "But she does have me in a cock cage." "Ew. Even worse," Kathy said. "Chores?" I nodded. "Peeing?" "No," I said. "Third parties?" I shook my head. "We had an assistant coach that Keisha invited into our bedroom. Anne Lofton. An older woman. We were too young to drink then, but Anne had liquor. And we always had pot. From Rashad before he got busted. He was bringing weed to Keisha when he was arrested." I nodded. That made sense. "So what you going to do, Juliette? You going to dump her and find a new domme?" "I don't know what I'm going to do," I said. "But I love her. I can't leave her." "Then God save your soul. Keisha is a bottomless pool. The longer you swim, the deeper you will sink. She can't help herself. She's Attila. She takes and she takes and she takes. And when she has it all, she thinks of new ways to control you, to humiliate you." "Did you get over her, Kathy?" "Not completely. I loved her, too. I wanted to marry her, too. But she kept imposing shit on me, and then she thought less of me for the shit I had done. So I went through Keisha withdrawal. I didn't date anyone for a year. I finally found a nice woman in the valley, a home-care nurse. Now that lesbians can get married, we probably will." I nodded. I was in a dress. Who was I to judge? "It's hard. You have to figure out which gender you want to be. You have to throw the maid shit away. You have to swear off men. And this is the most important thing: You have to stand up for yourself. You have to develop a backbone. Because if you don't, you'll wear panties and a bra forever." I looked at her. "And if I want to stay?" "Then why are you talking to me, pretty girl? You know that story doesn't end well. It's like your namesake and Romeo. Everyone dies in the end." So what do I suffer? The pain of loving her? Or the pain of losing her? * * * The next day, I was sitting in the kitchen, by myself. My mood wasn't the greatest. Rashad walked into the room, pulled up a chair and sat down. I looked at him. "May I pour you coffee?" I asked. "No," he said, and he looked at me. "You know, you ain't half bad for a white sissy," he said, and he grinned. "Why don't you cheer up?" "What is there to be cheerful about, sir?" I said. "You kidding me? You have the life you want, Juliette. How many people can say that? You have a lady who loves you. You have a bed. You have food. It's more than a lot of people on this planet have." "I've lost my job. I don't have any future. My hormones are so out of balance I'll never have kids again. You know, I read all these sissy stories, and the sissy is usually happy. She is usually flouncing across the kitchen cleaning the fucking pots. But in real life, this is hard, Rashad! I know I have a place to live. Does Keisha love me? I don't know. Maybe in her way. But she loved Kathy..." "Kathy is a bitch," Rashad said, "She fucked Keisha over. The whole time she was Keisha's submissive, she was fucking a guy in Covington. I wouldn't believe a thing she said." "She seemed so sincere..." "You believe who you want, girlfriend. Look, my sister isn't perfect. She's demanding as hell. But she's got a loving soul underneath it all. Juliette, she has you in dresses because she's a domme. That's who she is. And you're a sub. So it works. Look, I'm sorry she made you suck my dick. Well, actually, I'm not that sorry. It was good." I grinned. Nodded. "Look, Juliette. You have to stop thinking of her as doing this to you. You're doing this together. It's an adventure at opposite ends of the magnet. Stop thinking of yourself as being forced to wear a dress, and think of yourself as pretty. Stop thinking of being forced to sleep with extra partners and be glad you aren't bound by monogamy. You have so much for a sissy. Embrace it." I covered his hand with mine. "You know, you're a very nice man," I said. "Don't let it get around," he said. "It's bad for the rep." I leaned over and kissed him, softly. His lips were larger than mine, but they felt nice. Strong. And Keisha walked into the room. "Well!" she said in mock indignation. "My sissy and my brother. I am shocked at such goings on. Should I leave so you can blow him." I looked at Rashad. He shrugged. Smiled. "Later?" I said. Rasheed touched his package."Looking forward to it." Keisha laughed, then sat in a kitchen chair. "Can I have coffee,?" I scurried after and poured it. Rashad was right. I needed an attitude adjustment. I brought Keisha her cup. "Did you sleep well, my lady?" I asked sweetly. She looked at me. She must have recognized the change, too. "I slept okay," she said. "I wanted my sissy with me, though." "I am but a whisper away," I said. "Always." "Kathy came to see you..." "Yes. We have a lovely talk." "Did she warn you about me." "She did." "Do you plan to leave?" I looked her in her lovely face I did not hesitate. "Never. I'll be honest. I don't know who to believe. I don't know who to trust. So I'm going to trust us, what we have." She put her hands on my sides. She stood and looked down on me. "Yes," she said. Yes? "Yes, I'll marry you. It'll be a different marriage. You know that. I'll be in charge. But I'll always love my sissy.If we keep that in mind, I think we'll be okay." She kissed me. She turned and wiped my lipstick from her mouth. She pulled a ring out her pocket and slid it on my finger, It was gorgeous. The stone was was large and glistening. I knew it was a woman's ring, but all of my doubts and fears disappeared as soon as she put it on me. She was making a commitment to me. All I had to do is surrender. I threw my arms around her. I intended to hold her forever. "So, Juliette," she said. "How do you think you'll look in a wedding dress?" (c) 2015 by Cassandra Morgan

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Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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  • 38
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

2 years ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
3 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

2 years ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

3 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

3 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

3 years ago
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Irsquom my Wifersquos Sissy

My story starts 2yrs ago when l retired early from work, also at that time l was having trouble with my sex life, so went to see a doctor who informed me l was going through what he described as a male menopause which l never knew existed. My scrotum had shrunk and looked like a shrivelled ping-pong ball, my penis had retreated into my balls and could only be seen if l got an erection which measured almost an inch and with a cock that size l was finding it impossible to please my wife Jolie, so...

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