A Happy Sissy free porn video

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A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results. Sharon was more than a maid; she was a family member, as close as any blood aunt. She was a substitute mom, a big sister, a trusted advisor. And now Sharon was retiring. "Here's what I'm talking about," Monica said. "No one wants to work anymore," Monica was saying. "I think all the good maids have been snatched up by the agencies, and I don't want to pay that much. Hotel chains take a lot of them, too. It's hard to find a maid who wants to work for a single family anymore." Keisha was an ex-con. Julie had been fired from her last three jobs for theft. Marianne had been arrested for drunk driving...in her boss's car...while on duty. Kristen didn't drive. Betty Sue catered to families with children. Barbara only wanted to work for people of her faith, which involved the worship of trees. Monica laughed softly. She shook her head. "I swear, Andy," she said to me. "I've a mind to just let the dust gather. Hell, we've got rooms we don't use. Why worry about them?" She was blowing off steam, of course. We did have a big house, left to Monica by her late parents. It was the reason we had Sharon to begin with. Most couples our age didn't have domestic help. But Monica worked, and I worked part-time as a substitute teacher. We needed someone to keep the place orderly. It didn't have to be spotless, but how hard is neat? And so I watched her fume and agitate, looking in vain to find a new cleaner. Sharon had been with the family a long time, and Monica's family hadn't keep pace with the pay raises. Now, there was a sticker shock to what some girls wanted. And the old days had passed. Jenny wore a mohawk. Tammy had tattoos billowing out of her shirt sleeves. Chrissie was bald with "fuck the power" tattooed on the side of her skull. Monica sighed. She tossed a shopper away from her. "This is useless," she said. "All I can find is degenerates and drug dealers. I wouldn't trust a coffee cup to these women." I watched her blow off steam for a moment. Monica doesn't get angry often, but she was there now, and heaven itself couldn't calm her down. Finally, after she reached an even keel, I spoke up. "I'll do it," I said, my voice barely above a whisper. "What was that? What did you say, Andy?" "I said I would do it." Monica looked and laughed. "Right," she said. "You wouldn't even scrape your own plate after dinner if I didn't ride. your ass. Now you're going to clean this entire house every day." "I can do it," I said quietly. "Look, sweetie," she said. "That's very nice of you. I appreciate it. But we need someone good. Someone reliable. Someone who is a professional at maintaining a household." I shrugged. "I'd come cheap," I said. "And I wouldn't steal your jewelry." Monica thought about it for a minute. Then she shook her head. "Andy, you have a job," Monica said. "Besides, Sharon always dressed like a maid. I liked that." "I can do it," I repeated. "I'll quit my job.I'll wear a uniform." "Andy, I know we've role-played some in the bedroom," she said. "And you look nice in a skirt. But there is a difference between a husband who acts like a girl and a maid. You aren't even a transvestite, let alone a transgender, let alone a sissy, let alone a maid. I need someone good." I nodded. "I know," I said. "So you're going to work for a weekend and then I'm without a maid again," she said. "I'll do the job as long as you need me," I said. "A month. A year. I'd like to do this" She stared at me, and it was as if she was actually considering it this time. "What are you telling me, Andy. That you're a maid? That you really are a sissy?" I stared out the window. I felt like the walls was closing in on me. My eyes filled with tears. My breath got short. I didn't say anything. "Andy?" Monica said. "Talk to me Andy." I looked up through red eyes. I nodded. "I...I've always had these desires," I said. "I'm so ashamed. But, yeah, I guess you'd call me a sissy." Monica shook her head. "Since when?" she said. "Except for our role- play, do you even wear women's clothes?" I shrugged. "Sometimes," I said, blushing. "I'm careful. I was caught too much in high school. But I guess I've always had an interest in it." Monica started pacing the room. "My husband is a sissy boy," she kept saying to herself. "He wants to be my maid." "I think it would be exciting to try for a while," I said. "I've read the stories. I've seen the videos. I've dreamed so often about it. When Sharon left, it felt as if the door was cracked. It was now or never." "Maybe it should have been never," Monica said. "Tell me: Are you gay?" I was quiet for a minute. "This isn't about sex, Monica," I said. "This is about submissiveness. This is about that strange compulsion -- I admit it's strange -- to be at heel for a stronger personality. I've always admired your strength. It brought out my weaknesses." Monica frowned. She looked at me as if she was seeing me for the first time. Maybe she was. "Some of us are drawn to it," I said. "I'm sorry. It's like being left- handed instead of right, or brown-eyed instead of blue. I can't keep it out of my mind. I see a picture of a man in a maid's dress, and I want to hump the furniture. It's in me, baby." She bit her thumbnail as she looked at me. She nodded. "Okay, okay," she said. "Let me read up on this sissy stuff so I'm sure I understand. I'm aware of the fetish, but I need to know more. I'd prefer to start you off as a junior maid, maybe have someone show you the ropes. But here's what I'm thinking: If I agree, you have six months. If you do well, we'll sign a longer contract. But you know I want this whole house cleaned right. I want you to cook. I want you in makeup all of the time. I want you to wear the uniforms. I'm a bitch to work for. How does that sound?" "It sounds like hard work, Monica." I said. "I never thought it would be easy." "You're talking about being a full-time sissy, Andy," she said. "People will know. People will laugh. Hell, I'll probably laugh. Now, do you still want to do this? You can back out, and I'll understand." "I don't want to back out," I said. "Monica, this is something I want. It's the porch light and I'm a bug. I know it's not like role-play dressing up. But I've always wanted to go further. Not just as a transgender, but as a sissy. We'll both get what we want. You'll get a clean house, and I'll get to try out this lifestyle." Monica had no idea of the demons in my soul, of how the stories enticed me, or how even the word "sissy" seemed to be such a beautiful collection of consonants and vowels. She had no idea of the images that lived in my head, of petticoats and vacuum cleaners and high heels. This wasn't one of those stories where an evil mother-in-law pushed a sissy into panties and turned him into a zombie along the way. This wasn't a wicked wife who just wanted a reason to cheat while he watched. This was real life, and I was a volunteer. For months, I had fretted over just how to escalate this life. Now I had found it. And God help me. * * No, we didn't rush out and put me in a dress. We sat in talked about cooking, if you want to know the truth, and different sauces that went with each meat. We talked about cleaning, and which bleaches were too strong to use of fine fabric. We talked balancing laundry days and ironing days. We talked about working a hard but reasonable schedule. You know, maid stuff. It wasn't until that night, when we went to bed, that Monica addressed the feminine part of the equation. She tossed me a black nightgown. She had a grin on her face. I pulled it over my head. She threw me a pair of black panties. I put them on. I felt like cheering. They were so smooth, so slick. For the first time in my life, I felt free. I was feminine. I could embrace this lifestyle without regret. I crawled into bed and Monica pulled me roughly to her. She traced my body underneath the nightie. She touched my cock through the panties. She kissed me. "From now on," she said. "You wear lipstick." "Yes ma'am." "And eyeliner." "Yes ma'am." "And mascara." "Yes ma'am." "And don't call me ma'am. It makes me feel old. I'm Monica. If I want you to call me Grand Sultanas of the Orient, well, I'll let you know. And you can stop with this ma'am shit. I still want us banter back and forth. It's the best thing about you. You can't disrespect me, but you can still joke around." She crawled over me, pinning my wrists in her palms. I looked up at her, submissively. She kissed me and ground her crotch into mine. There was a hunger to her that might, a force that seemed to overwhelm me, to dominate me. There were moments when I forgot which one of us had the vagina and which one had the penis. She palmed my flat chest and whispered "Imagine it. Imagine your titties in my hands. Imagine my dick against your stomach." I wriggled beneath her, my mind filling with the images. She rubbed her hands up and down my sides. She crawled up my body and crouched over my face. She lowered her vagina until I could lick her. I felt feminine. I felt meek. I felt like a woman being taken by her man. "Call...call me names," I whispered. "Slut," she said. "Pussy," she said again. "Bitch," she said. "Sperm-breath," she said. "Cocksucker," she said. "Sisssssssssy," she hissed. I smiled at the words. I kissed her. Yeah, this was going to work out. ** I woke up in the middle of the night, and her side of the bed was empty. I saw a glow coming from her office. She was on the computer. I lay awake for a long time, thinking about the declaration I had made, wondering what she would decide. There was no taking it back. I had come out to her. I had urged her to make me a maid. As she wondered, what did I know about being a maid? I had fantasized, but I had never worked as a daily maid. I had never had a mistress. Monica came back into the room. She saw I was awake and gave me a small smile. "So how did the nightgown feel," Monica asked. I smiled. "Like angels caressing my skin," I said. "Every time I would roll over and feel that I was in lingerie, I felt beautiful and feminine." "Then why not just wear the clothes, Andy?" she said. "Why work your ass off with dishes and kitchen floors?" "Because that's who I am. I'm submissive. I like doing. I've never had a mistress, but I'd be good for one. I'd work hard, and I'd be loyal, and I wouldn't care what anyone said to me." "People can be cruel," Monica said."You're going to have be strong to be this weak." Monica went to her closet. She laid out one of Sharon's old uniforms for me. It was battleship gray, and it had a white apron. She dug out a plain white bra and a white pair of panties beside it. It was all functional, not sexy. But I didn't say a word. I started to hook the bra, and Monica shook her head. "Not yet," she said. "Remember, a maid has to clean her body. Then she can clean the house." So I went back to the bathroom, and I stepped into our tub -- I was usually someone who took showers -- and washed with some of Monica's scented soaps. She handed me some foam, and I applied it to my body. A few minutes later, most of my hair had fallen off. She had me touch up the rest with a pink razor. I sat at the vanity and brushed out my hair. I kept it long, usually in a low ponytail, but I started thinking about style and color. Maybe a dash of blue. Maybe pink. "You ready to give in yet, girlfriend?" Monica asked. "It's not to soon to back out. You don't have to be a sissy." "I'm okay," I said. "I asked for this. I need this." "Keep that in mind," Monica said. "So what are we going to call you when you're a girl? Andrea? Angela?" I thought a minute. "I've always imagined myself as an Amy." Monica smiled. "Okay, Amy," she said. "That's what I'll call you. Even if you go back to pants, you're Amy to me. Deal?" I nodded. She fluffed my hair, as if to test its length. She fingered my ears, as if to see how many earrings would fit. She led me back to the bedroom. "Put on your panties and your bra," she said, accenting the word "your." Then she wrapped a bra around me. She put extra panties into the cups. "Think of it as 1-2-3," she said. "First stuffing, then forms, then boobies." She looked at me as if I were going to say something. I didn't. I was too dazed by all of the sensations and all of the feelings. She handed me a white girdle, and I wriggled into it. She handed me hose, and I rolled them up and put them on. I stepped into the dress, and she zipped it up. I looked into the mirror, and I saw a younger version of Sharon. A young female maid ready to take on the world. I didn't have on makeup or a wig, but I thought I looked pretty good. I curtsied to myself. Monica laughed. "Keep that up," she said. "I want to see that a lot, Amy. Do that for me, and I'll dance at your wedding." "I'm already married," I said. "Yeah," she said. "For now." I grinned. "I don't think Thor will marry me." "Oh, nice arms. Captain America." "He's cute. Batman. The first one." "I've got it. That stretchy guy: Mr. Fantastic. He can stretch the most marvelous parts of his body. "The Hulk," I said. "You know what they say. If you go green, no other will ever be seen. Monica laughed. She turned serious then. "Amy, I spent half the night reading about mistresses and their sissies," she said. She exhaled. "I think I can do this, okay. But you have to trust me. If I humiliate you by bringing a neighbor here, it's for your own good. If I make you go for a bra fitting -- and I will -- then you have understand it all's part of the greater good." I swallowed, but there was only dust in my mouth. Was I really ready? * * * Later that day, we went to the uniform store. We bought four maid's dresses -- black, blue, pink and red. We bought bras and panties. We bought pantyhose. We bought functional shoes and two pair of heels. "For him?" the shopkeeper asked. "Yes," Monica said. "How did you guess? Is he sending out sissy vibes again?" He shrugged. "You have no idea how big this shit is for girly men," he said. "Most of our maid's stuff is bought by guys or their wives. Fucking Democrats. They're turning all the men into pussies. Before long, they'll pass a law than men have to have periods, too." Monica laughed. I tried to ignore his words. I had sacrificed my right to be offended. "What else do most people buy?" Monica said. "Girdles," the salesman said. "Girdles are very big for the pussies. Breast forms. Panties. Bras. They go Flesh and Fantasies for their sex toys. They go to Macy's for their makeup. They buy their earrings at the Mall. But we can fix you up with daily dresses -- not just uniforms -- and shoes. We have your falsies if you need a pair. " Monica bought a good set of breast forms. She thought about a pair of tennis shoes, but she decided to hold off. The shopkeeper looked at me, the clothes in a bundle in my arms. He shook his head. "Democrats," he said again. * * * If I still wondered if Monica took me seriously, she convinced me when we drove up to the Adult Emporium, a little sex toy shop on the south side of town. She kept looking at me, waiting for me to come to my senses and to tell her to take me home to see if a football game was on while strippers worked as the team cheerleaders. Maybe there would be a bunch of men to get together with my buddies to play paintball and act like idiots shooting each other. But I was quiet. I had waited too long to speak up, and I finally had. There was no calling it off now. I just had to brace for whatever coming storm. I knew it wouldn't be easy. I had read enough stories to know that. But to tell you the truth, I couldn't wait to get into my uniform. I couldn't wait to practice on high heels. I dreamed about lipstick; now I would get to wear it. I was a sissy, and I was more excited than I was afraid. We pulled into the sex shop. Flesh and Fantasies, it was called. Monica opened the door, and I entered. I swallow hard, one last blast of insecurity, then I looked around. I had walked into Wonderland. Have you ever seen the a nerds' convention where all the new electronics are shown? I was that way with all of these terrific appliances around me. There were racks of clothing. There were display cases filled with toys. There was punishment gear for the bondage oriented. It was Toys R Us with a hard on. Whips. Chains. Lotions. Handcuffs. Dildos. Leather corsets. Heels. Books. Movies. Magazines. Monica stopped at their rack of maid's dresses, even though we had just bought four. But she wanted a sexy outfit, too. "What size are you?" she asked rather loudly. "Um, my jeans are a 33 waist. My shirts are small," I said. She had me try on a pair of red heels. I walked around the store. It fit. She put it, and its mate, into the cart. She picked up a feather duster. She stopped in front of a case filled with small metal contraptions. I looked and scowled. "Why do we need one of these?" Monica grinned. "You need one because sissies surrender control. I'll be your key-holder, baby. I'll decide how long you're caged. I'll decide when you're free. I'll decide how hard you have to work to earn a weekend pardon. It's the ultimate submission." "It's a Gerbil jail." "A mousetrap," she said, nodding. "A prison cell." "The chain gang." I stared at it, imagining the lock being shut. "This could change our entire penal system," I said. "Forget about putting the men in prison. Just put the manhood inside." "Yeah," Monica said. "I'm innocent, but my dick is serving a 10-15 stretch for arson." The saleswoman walked over as we were laughing. Monica picked out a small stainless steel model. "We have some lovely butt plugs that match that, ma'am," the girl said. "Ooh, that sounds lovely," Monica said. "What do you have in a dildo?" "What size?" "Oh, I'd say clear to the tonsils." "Oh, we have a great assortment," the girl said, giggling. "We have big ones for the experienced sissy, and we have small one for beginners. We have ones that squirt and ones that get hard. How long as your girl been at it?" I blanched at the word "girl," but it didn't phase Monica. "She's a newbie," Monica said. "She hasn't even got a bra yet." Monica picked out a blue plug that was small at the end but tapered to a wider base. Then she asked for a strap-on with a harness. She wanted a collar and a leash. She bought a tube of breast cream, guaranteed to make them grow. It was as if I wanted a visit to the park, and Monica was buying Disney World. This was so much. This was so fast. And I was so hard you would not have believed it. *** That evening, we took a walk around the block and down the jogger's path at McClendon Park. We passed several people -- some of them I knew -- who turned and stared. My hair was still short. Monica had said no to my wearing a wig, so we walked down the path, me in my pink maid's dress, heels on my feet, earrings in my newly pierced ears, and heads turned. I blushed with each passer-by. I felt like the lead float in the Pride Parade. My nails were painted silver. I had a single pearl on a chain around my neck. "Look, Amy," Monica said, loud enough to be. heard. "That woman recognizes you. She thinks you're gay. Are you gay, Amy." "You know I'm not," I said, hoarsely. "I know I didn't think you were," Monica said. "But if someone were to dangle a dick in front of your face, would you suck it? Don't answer. Just think about it." She laughed. "Why are you giving me shit?" I asked. "You're getting benefits from this, too." "Amy, Remember the literature about how sissies like humiliation, Well, this is it. As you come out, more and more of your friends and family will recognize you. I may take you see Father McCabe. You have to accept that, or this is just a costume party. Now, trust me, and stop being conflicted. Embrace this." Monica was right. I wasn't being forced. I had asked for this. It didn't matter if a neighbor saw me in a dress instead of pants. I was a sissy. I raised my chin. Proudly, I walked forward. * We were weary from shopping by the time we got ready for bed. Once again, I put on a nightgown. "So how did you like the maid's outfits," Monica said. I looked at her and smiled. "I loved them, especially the pink one," I said. "They all fit perfectly. They all reminded me that I was a lesser being to you. The plug wasn't comfortable. But I'll get used to it, I guess. And that cage is driving me flipping crazy." Monica grinned. "A lesser being?" "Well, yes," I said. "I'm your servant girl. I scrape and clean and go to my knees to remove stains. I'm lesser, and I don't mean that with any false humility. It's the stations we've both accepted." Monica looked at me. "Baby, I'm not sure I'd be good as a Mistress. From what I read, there are hundreds of practiced Mistresses in the city." "But I don't trust them, Monica. I don't love them." "Ah, baby, I love you too. But right now, I'd love a back rub." I smiled. I went to work. * * The next day, I was folding the laundry -- Monica was at her office -- when there was a knock at the door. Not thinking, or not caring, I went to the door and opened it, expecting there to be a salesman. Instead, Gus Collins stood there. Gus and I have been friends since our freshmen years of high school. I was the nerd who helped the jock with his homework, and we've gotten along since then. He was 6-2, and I was 5-7, so everyone called us Mutt and Jeff, like the old comic strip. Now, he was standing in the doorway, looking at my black maid's dress. "Shit," he said. "Exactly," I said. "What the fuck is going on on..." he said. "Well, right now, I'm folding the laundry," I said. "Why are you wearing a dress?" he said. "Because when I looked in my closet this morning, there it was." I said. "Seriously, asshole. Are you some kind of fag or something?" "I'm not gay," I said. "Except on Tuesdays and Thursdays. Wait. It's Tuesday. You're in luck." "Ha," he said. "Seriously, is this some kind of kinky shit with you and Monica?" he asked. "No, Gus. This is all on me. I've become submissive to Monica. Some people would call me a sissy. I thought you might suspect." "Shit," he said. "You already said that," I said. "Are those real?" he said, looking at my chest. "No," I said. "They're fictional." He scowled. "You're a maid." he said. "You clean toilets. You make beds. You wash dishes." "Yes," I said. "I do." "I'm shocked," he said, laughing. "I'm appalled. I'm outraged. And I have a question: Can I hire you?" "You can ask Monica about that," I said. "Spin around," he said. I twirled, and he took it all in. My legs, which were killer, if I say so myself. My butt, which was flat. My boobs, which came in a package. My lips, coated in red lipstick and out for sport. "You're pretty," he said. "Thank you," I said. I curtsied. He broke into laughter. "You sure this is what you want?" he said. I nodded. "It is. Are you okay with that?" I asked. "I'm okay. Now, who do I have to see about a blow job?" I threw an un-ironed shirt at him. We both laughed. * * Monica had come home frazzled, and I got her a glass of wine. She said she'd rather have a scotch on the rocks. I fetched it. She put her arm around me, and I snuggled against her. When we did that, all was right with the world. "Gus came by today," I said. "And?" "And nothing. He came by, and we talked. He seems to be okay with it." "Did he want you to suck his dick?" Monica asked. "Monica!" I said. "Why would you say that?" "Because every man under the sun wants his dick sucked," she said, giggling. "If Hoover had an blow job attachment for their vacuum cleaners, some men would marry them. The way to man's heart may be through his stomach, but it takes a left at his throat." "Gus doesn't want me. I'm a sissy." "Sugar," Monica said. "Look at yourself. You've got a cute little bubble butt and a cocksucker's lips. You've got legs that go clear up to your ass. Any man would be crazy not to want you." "I've also got a dick." "Well, a tiny one." "But a big heart." "And a nice tongue." I didn't mention that Gus had made a blow job joke. That was just Gus being Gus. But for just a mili-second, a fleeting image of Gus's penis flashed before my eyes. "Do you think Gus got a boner?" Monica asked. "How would I know that?" I said. "Well, when he put it in your mouth, was it hard?" "Harder than Chinese Arithmetic," I said. "Harder than a Rubik's Cube," Monica said, laughing. "Harder than dancing in high heels," I said. "Harder than Iron Man's cock cage," She said. We fell onto the bed, laughing. It was a good day, even with the cage. * * A maid's job is not easy. You rise and do your makeup. You dress. You start to cook. You serve. You clean up. You put in a load of laundry. You vacuum. You mop. You take the laundry and dry it. You shop. You change into your evening outfit. You cook again. You serve again. You wash dishes again. You get Monica a drink. You fold laundry. You iron. If Monica desires to peg you, you bite the pillow.You plead to have your cock cage released. You give up. You shower. You dress for bed. Tomorrow? Ditto. But through it all, I find myself smiling. I sing. I hum. I am happy. Some of us, I read, are miserable. They are forced into this lifestyle, and the fight to return to manhood, and the whole experience is torture. Not for me. I truly had found my calling. The maid's dresses were perfect. On the rare night I got to wear a real dress, it was even better. When Monica would nuzzle me and tell me that she loved me, it was a parade. One by one, our friends came around. They laughed at me, and they exchanged little witticisms, and they had so much fake kindness it made you want to barf. But that was okay. Monica explained to me that the hard times were the first times, the coming-out times when vanillas don't recognize other flavors. After that, you were just you. Old friends might ignore you, and relatives thought you were scandalous, but it was all part of the transition. Some friends changed. Some disappeared. But some were loyal, and some tried to understand. Mothers, though, are harder. Monica invited my sweet, quiet mother, Betsy, for dinner. She wasted nine seconds before she asked me if I was a fag. She simply couldn't grasp the idea of a human wearing a lipstick and not wanting to stain someone's dick. She asked if I had had an operation (no), if I wore panties (yes), if I slept with men (no), if I did the ironing (yes), and if black men's sperm tasted differently from white men's (all of the available data is not. yet in.) When I grew up, mom had caught me in dresses several times, and now I was "one of those Jenner girls" in a dress. She kept calling me a drag queen (I'm not). She asked I was used to boobies yet (Getting there). Oh, she had her wineglass out constantly when I would serve. I was good for that. Except for that, I could have blown the pizza guy, and she wouldn't have blinked. "So you cook? You clean? Do you scrub toilets?" she said. "My son is so stupid he became a woman, who makes less money than a man, puts up the bullshit of men, and lets guys rest their balls on his chin. So why are gays so prideful?" she said. "Well, some of those balls are pretty impressive," Monica said. For Mother's Day, remind me to buy her a dildo. Some folks need to get laid. * * * Monica sat on the couch, her arms around me. I sat between her legs, leaning my head back onto her shoulder. "So your Mom's a bitch, huh?" I chuckled. "She is that. But it can't be easy on her to see her son in high heels." "I suppose not." "I felt like some sort of slimy creature who should be stepped on." Monica's hands were moving now, and it felt good. Her fingers traced my breast forms, pinching the nipple. We both noticed that I couldn't feel it. "Amy, have you thought about...." "Boobs?" I said. "Sissies are always thinking about boobs." She grinned. "And what do you think about them?" "I think ... someday. Just promise me I get to show them to Mom and bring on that brain hemorrhage." "I want you to show them to me. If I get a vote, I'm voting one big nipple up." I turned. I kissed her." Monica looked at me, then reached into the night table. She grabbed a gadget and stood up. She stepped into the harness, and she was wearing a very large black dildo. She waggled her eyebrows at me. "Hubba- hubba," she said. I stared at it. "Are you joining a softball game," I said, staring at its size. "Hah. I'm in the Henley Regatta. This is my oar." "I thought I was your 'or." "Funny girl. I hope you can laugh while I'm pegging your ass." I rolled over. I stuck my butt into the air and buried my face in the pillow. "Come to mama," I said. "Mama has itty-bitty balls," Monica said. "And her pee-pee is in prison. Repeat after me: Attica. Attica." I giggled, but I stopped when Monica started rubbing lube into my rear. It felt pleasant, her hands and her fingers typing a novel in my backside. But then she let the monster loose, and I squealed. Someone had put a flamethrower in my ass. But, as always happens, the nerve endings took over, and angels touched my butt, and it was a slice of heaven. Imagine an oil derrick in your butt, but it isn't oil that's spewing. * * Monica was glum on Monday. She was depressed on Tuesday. She was in the dumps on Wednesday. On Thursday, she was just in a bad mood. I stayed happy as I did my chores. I figured she would tell me whatever was bothering her when she was good and damn ready. It wasn't my place to question her. And that's one of the real challenges of being a sissy. You shut up and don't pry. There are times when a sissy can ask out of love, but a mistress runs the time clocks in our world. Finally, on Friday, she turned to me. "Sit for a minute, Amy," she said. Uh-oh. Good news has never followed a "sit for a minute" opening. I sat. "Amy, you're a good sissy," she said. "You work hard, and you have the best attitude in the history of sissies, way back to when Delilah put Sampson in a skirt. Or when Ulysses dressed a as woman to try to get out of the wars." She laughed. "Yes ma'am," I said. Ma'am? Monica doesn't make me call her ma'am. Why did I do that? "But I have to tell you, I'm a little frustrated," she said. "Now listen to me, because this is a challenge even for the best sissies. There is a guy at work...Kevin... who has been coming onto me lately. And I find him ... interesting. Amy, do you know what a cuckold is?" My mouth went dry. But I answered her. "Yes, ma'am." "So let me ask you. Forget you're my sissy. Be my friend. What do you do? I don't want to cheat without your permission. But honestly, I want to sleep with this guy, Amy. I miss dick. Hell, yours is locked up most of the time, and even when it isn't, it's your tongue that does most of the work. Hey, Amy. Do you think they have a chastity device for someone's tongue." I didn't laugh. I was imagining watching a guy fuck my Monica. In my mind's eye, he was pretty big. In my mind's eye, he was pretty good. I tried to shake the image out of my head. "Amy...Amy, what would you do?" I straightened up. It was time to be a supportive sissy. "It doesn't matter what anyone else would do, Monica," I said. "It matters what you need to do. I think you should sleep with him if he will make you happy. I'll support you. I'll be there. I'll hold your hand if you want." She smiled. "Will you fluff him for me?" "Twice. No more than three times." "You know, sperm can get in your eyes," Monica said. "Not to mention your thighs." She laughed. "Be serious," I said. "This is about the two of you. Sissies don't get a vote. Don't let other details tangle you up. And when it's over, we'll still be us. What we have is bigger than sex." "Well, Kevin's bigger, too," she said with a glint in her eyes. Kevin was a tall man, muscular and black with great teeth. He was nice to me, not that anyone spends much time talking to the help. He knew he was at our home for sex. Still, they flirted and joked and let their hands linger over each other. For me, the hard part was deciding how much space to give them. Monica was about to take a lover. But she still wanted me to fetch and carry. Drinks. Snacks. No one spoke to me, and I didn't speak to them. I was a domestic who was not allowed to see anything, to say anything, or to think anything. Finally, they retired to the bedroom. Monica looked at me and asked "Can you bring us some ice water?" she said. So I poured two tall glasses of water, and I brought it to them. By the time I got there, his pants were off and her shirt was unbuttoned. Kevin was impressive, if you happen to like very long, very hard penises. Monica leaned over and kissed the boa constrictor right on the snout. I turned to go, but Monica shook her head. "Stay," she said. So I took a chair, and I watched my wife take a club to our wedding vows. She climbed on top of him and kissed him, and he rolled her over on the mattress. He kissed each breast carefully. He ran his hand over her ass. I was mesmerized. It was so big, so impressive, bigger and more responsive than her dildo. When he entered her, she made a primal grunt, and they were screwing. And I have to tell you, it was a beautiful sight. Her vagina clenched him, and her fingernails drew across his back. She was a tiger in a cage, biting, clawing. He was a foot taller than her, maybe 100 pounds heavier. But she dominated him as easily as she had dominated me. When he came, he was a fire hose, with a thick, heavy stream flooding the area. It looked like a slide at a water park. Monica flopped back on the bed, her legs still spread from the heat. Kevin rolled over, spent, that muffler of his dormant. Their breathy was raspy, as if they need oxygen. I watched for a minute, my head spinning. Monica reached out and squeezed my hand. I squeezed back, as if to tell her I was okay. Without a word, I climbed up on the mattress and I inched forward. I had read that a good sissy never leaves the mess inside her wife. I kissed her public hair softly, and wordlessly, she wrapped her fingers in my hair. I licked up the spew on her crotch, savoring Kevin's taste as I licked. I pushed my tongue deeply into her, feeling the mingled juices of the two of them. There was so much of it, but I lapped it like a dog at the water dish. I twirled my tongue, and I probed her deeply. Finally, I lifted myself off of her. And Kevin looked at me and nodded. I leaned forward, and I licked Kevin's sperm off of him. I took his cock into my mouth, and I sucked it softly, not so much as a sex act but as a cleaner. I licked his balls and that crevasse at the top of his legs. He began to harden, and I bobbed faster. What had started as simple courtesy was turning into my first blow job, and I didn't want to stop. He came again, less sperm, and it was more watery. But it was enough to leave with a "cocksucker" brand across my self-identity. Kevin reached over and kissed Monica. "Nice," he said. "Twice?" she answered. * * The next morning, I was quiet. Not out any wrong feelings toward Monica, but out of my knowledge that I wasn't quite as straight as I had maintained. I know, I know. Sissies don't get labels. They merely try to make their masters and their mistresses happy. The rest is a matter of labels and egos, and a sissy can't afford either of those. But even if I let my own questions about what giving fellatio said about me, I was pleased that I had made Monica happy. Yes, and Kevin. A maid's job is the please, and to sacrifice, and to rush toward the dirty jobs that are beneath her mistress. That can be true of cleaning a frying pan, and it is true of bedroom cleanup, too. Monica walked into the kitchen, stretching. Kevin had to leave early in the morning. She took coffee from my hands. "Thank you," she said. I nodded. "I am yours," I said. "But next time, can you get an individual sized dick? These family size portions damn near killed me." Monica laughed, and it was the sound of a satisfied woman. "I like chocolate," she said. "I can see that," I said. "You might get diabetes. I thought you were Catherine the Great, and he was your horse. Hi-yo Silver." "Hey," she said. "What kind of sissy makes fun of her mistress." "Sorry, ma'am," I said. She laughed. "Skank," she said. "Slut," I said, overstepping my bounds. "Whore," she said. "Bimbo," I said. We went on that way, swapping soft barbs to show our love for each other. The truth of it is that if she brought a thousand men to a thousand climaxes, I would lick her clean. Sissies did that for their mistresses. Call it a sissy cocktail. Two parts sperm mixed with one part sperm. Yum. * * Monica, as you might expect, widened her list of prospective suitors. She was enjoying being in power, and men were a big part of that. Sometimes, I was involved. Most times, I was not. It was always her call. But I was always -- always -- there to lick her if she wanted me to afterwards. Think what you want. But I think I had discovered my superpower: I was Tongue Girl. Really, it isn't that hard to adjust to. Monica was fulfilling a need in her body. I was in support of her. If our old friends saw her on a date with another man, well, that's just the way it was. I was a sissy. Sue me. One Saturday night, Monica had a date -- two men, I think. I called them the Corsican Brothers. There was a soft knock at the door. I opened the door, and there stood Gus, with that same loopy grin on his face. "Hey, kiddo," he said to me. I ushered him into the kitchen, and I got him a beer. I offered him something to eat. "How you doing, Andy...I mean Amy," he said. "I've missed you." "Missed me? I haven't heard from you for months." I kidded. "Well, it's hard. You're a kept sissy. I need to keep my distance." "I'm sure the women of Cincinnati appreciate that," I said. "I do what I can," Gus said. "Yeah, there are dozens of babies born every year who will attest to that." Gus chuckled. "See. This is what I missed. It doesn't matter if you're in a dress. You still have that gift of banter." "We could always make each other laugh," I said. "I don't know if I should tell you this, but Monica called me." "Monica? She's out on a date. Can I take a message?" "No, numb-nuts," Gus said. "She called me to invite me to come and see you while she was out." "Me?" "You." I kept wiping the sink to calm the buzzing in my ears. "She thought you might be lonely." "Oh, no. I'm fine," I lied. Gus walked up to me. He towered over me. He lifted my chin, then softly kissed me. "Um, Gus. I'm a boy, remember." "No you aren't," he said. "You know better. You're a sissy, and you locked away. But we can find stuff to keep us happy." He kissed me again, his tongue probing my mouth. I felt his hand on my budding breasts. On each of my nipples. Marvelous! "I can't," I said. "Monica." "Your mistress knows I'm here. She knows I'm going to fuck you." The word sounded blunt and direct ... and beautiful. "You think you can handle all of this," I said, waving my hands over my body. Gus laughed. "Well, it might take me all night long, but I'll give it a shot." This time, it was me who reached up and kissed him. I ran my hand over his cock. "Where?" I said. "Cleveland?" he said. "Funny guy. Where as in here or living room or bedroom." "Bedroom," Gus said. "I want to wake up next you. If Monica allows it, I think we could be sweet together." "Monica doesn't care. She's dating the Chicago Bulls. The 14 of them are very much in love. I wonder if she fucks the coaches, too?" He chuckled. We walked up he stairs, his hand on the base of my back. He entered the bedroom and pulled off his shirt. He still had the bulging muscles. He still had the flat stomach.. When he pulled down his pants, he still had a dick and a half in his shorts. "Needledick," I said, acting as if I wasn't impressed.. "Drainstopper," he said, bragging on his own size. "Button dick," I said. "Tripod," he said. "Penal floss," I said. "Stallion," he said. "Shrimp," We started laughing at each other again. Then he kissing me, and he was unzipping my dress. "I never fucked Hazel before," he said. "Alice Nelson? From the Brady Bunch?" "Rosario? From Will and Grace?" "Mary Poppins?" "Nanny McPhee?" "Mr. Belvedere?" "Hey. Mr. Belvedere wasn't a maid." "He was. He went by Bella, and he was the biggest sissy since Ms. French." "You mean Mr. French." "Do I?" "You need to use that mouth for something besides talking," he said. "Yes, Master," I said. "Better." Gus shifted in the bed. And I went down for my dinner. It was big, and it was thick, but the first thing I noticed is that it was warm. It was sweet on my lips, and firm in my hand. I coated the bulb with saliva and gently sucked. I licked up the shaft and down. I swirled my tongue around the head of it, then started to bob my head, shallow and then deeper. He gripped my head and moaning. I licked faster. I blew it on the bulb gently. I smiled up at him, enjoying the ecstasy on his face. He came, and I capped his dick, savoring every drop. It was a sissy's reward to taste her lover. He kissed me. "Not awful," he said. "Okay," I said. "Fair," he said. "Average," I said. He looked at me and grinned. He kissed me. "So, big boy," I said. "You ready to try the ass?" "Give me a minute," he said. "As soon as my heart starts again, I'll be there." * * "Here's the question," Monica was saying. "Forget about shame, forget about judgment. Are we happier than we were yesterday." I lay in the crook of her arm, looking up at her. "Whatever you decide," I said. "Well, that goes without saying, doesn't it?" She grinned. "Seriously, I think we're going to keep the door unlocked. I want to meet anyone you're going to sleep with, and I have full approval. But I want to experiment. I met a great woman the other day. She intrigues me." I laughed. "What?" she said. "You," I said. "You'd fuck a goat." "Maybe. But you'd lick me clean afterward." "Ewww," I said. She laughed. "I love you," she said. "I love you, too." She kissed me. Life was good. Sissidom was good. I was happy. Copyright, Cassandra Morgan.

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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

4 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

2 years ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

4 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

4 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

2 years ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

4 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

4 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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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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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...

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