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Steps By Cassandra Morgan It started with an unmade bed. It was that simple. Just a mass on rumpled covers, cast aside. A top- sheet. A comforter. Scattered pillows. It was messy and unkempt, as if Russian wrestlers have slept underneath. My wife Cynthia got up earlier than I did. She rose at 6 a.m., and she dressed in the dark so I could sleep. She was a psychiatrist, and she tried to get to her office by 9, and it was all the way downtown. I didn't have to be to work until noon managing a Best Buy near our house. And so, one morning I made up the bed. Give me a medal. Cynthia liked things to be neat, and so I would rise. I would straighten the top sheet. I would strip off the comforter, and I would fold a lacy blanket she had picked up on a trip to Wisconsin and drape it over the foot of the bed.It wasn't much fuss, and Cynthia liked crawling into a made bed at night. "You are such an angel, Louie," she said to me. "I love that you do things for me. But there is one little thing..." "Yes, Cynthia..." I said. "Louis, the sheets need to be washed more often than the weekends," she said. "Could you run them through the washing machine for me daily? Would that be too much trouble?" "Of course not," I said. "I can do that." And so washing and drying our bedclothes became part of the routine. It added some time to my chores, but it wasn't like I was digging ditches. It's easy enough to do. Cynthia loved flowers, and every day she had a standing order for fresh-cut roses. I took to picking one of those roses from its vase and laying it on her pillow. She gushed. I was the sweetest man ever. I started rising when she did, and making her coffee and toast. We would sit there in the fresh morning, and we would talk about our days. Then I would wash the bed-clothes and make up the bed. It was easy, even when Cynthia started adding a dress or two to the wash. Again, it was no big deal. The washing machine was big enough, and the clothes could share the same cycle. The ironing didn't take long. Cynthia was happy with my efforts. She jokingly called them "my wifely duties," but then would laugh and wink, so I knew she was kidding. I actually began to enjoy the work. I would vacuum several times a week. I would put food in the crock-pot so we had something to eat for dinner. I washed the dishes. It felt like I was doing something for Cynthia, and I liked that. She liked it, too. Subtly, the daily chores became mine. Washing. Drying. Mopping. Scrubbing. Vacuuming. Cooking. Folding. Ironing. Oh, I understood, Cynthia had a real job, a grown-up's job, while I only unpacked new DVDs. This helped to balance the scales a bit. The only thing that bothered me was when Cynthia made light of my efforts. She was being funny, I know. But humor can often sting. "This morning, during your girl-time, could you iron my black dress?" she would say for example. Or "when you're acting like the maid, can you cook broccoli as a side-dish." Once, she pointed out an orange dress and wondered if it would show off my legs. She would giggle, to show she was just having fun. But there were times it bothered me, to tell you the truth. It went on that way for the better part of a year. I would do chores, and I would make dinner, and she'd sometimes tease me. It became routine, accepted. "Louie," she said once. "Is there some reason you do all of these chores?" "I'm just trying to make things easier for you," I said. "But, inside, do you get a nice feeling when you do them?" "Well, I'm gratified that you like it, I guess. But don't act like I'm weird for doing it. Do you want me to stop?" "Depends. Do you want to stop?" "Are you analyzing me?" I said. She laughed. "No, Louie. We're just talking. As far as I'm concerned, I have the best wife in the world." I laughed. "And don't you forget it, mister," I said. * One night, Cynthia brought home a package for me. Inside was a pink apron with red flowers on it. She laughed loudly, enjoying my reaction. "Is the little woman offended?" she asked. "Is it her time of the month?" Oh, it wasn't deliberate. Cynthia is a psychiatrist, remember? She knew all about insecurities and self-doubt. I knew she wouldn't try to hurt my feelings. But she had been raised with four brothers. She knew about family giving each other a hard time. Off the clock, Cynthia could jibe with the rest of them. "Hey, wife," she said to me one night. "What do you want for your birthday? Earrings? A new dress? Heels?" I blushed. "I just want you, Cynthia," I said. She chuckled. "The wife wants her husband," she said. "Isn't that precious?" I looked at. her. She looked back at me. Finally, I dropped my eyes and went back to the dishes. * * One day, I was cleaning the den, and I came across a magazine I didn't recognize. It was oversized, and it was colorful. And it took my breath away. It was called "Sissy." On the cover, it had a picture of maid running a vacuum cleaner. But if you looked closely, the maid obviously wasn't a woman. It was a guy, in red heels and wearing a blonde wig. Sitting on the couch was a stern looking woman, posed as if she were overseeing the maid. I swallowed hard. I put the magazine down, then covered it with an issue of People. I resumed cleaning. Then I came back, and I dug out the Sissy magazine again. I quickly flipped through it. There were photos of sissies kissing the feet of women, or getting spanked, with collars and leashes attached. Toward the back, a maid was simulating oral sex on a man who wore a mask over his entire head. There were male maids dusting, and washing dishes, and ironing. There were maids kissing. There was a gallery of men in different colored maid's dresses. My breathing had gone shallow. My mouth was dry. I put the magazine back, and I noticed I was erect.. I went to the bathroom and washed my face. I tried to forget about the magazine, but I could not. That evening, Cynthia came home and dropped her briefcase on the table. I brought her a gin-and-tonic. She took her drink, and she looked like she was going to say something. Finally, she patted the couch beside her, indicating I should sit. I sat down. I glanced toward the stack of magazines on the coffee table, but I said nothing. "Louie...we need to talk," she said. "Do you know what a sissy is?" I swallowed. "Yeah," I said. "It's a girly-boy. Like a little boy that plays with dolls." She smiled. "Well, that's part of it. But psychologically, there is something that is called a 'sissy boy syndrome.' I was reading about it today in Psychology Today. It's about grown men who want to be effeminate, who like to dress in girly clothes -- like maid's dresses -- and do housework. Louie, I've begun to wonder if you're like that." "No, Cynthia, I'm not." She shrugged. "Well, you act like it. That's the reason I've made so many jokes about you being girly. It's the reason I brought home that magazine you keep glancing toward. Remember when I bought you that apron? Hell, Louie, I was going to buy you a maid's dress and leave it on the bed." She paused. "There is nothing wrong with this, Louie. Nothing at all. It's just a compulsion. You and I have never been better. Our house has never been cleaner. But if you need to expand this, let me know." I looked at the floor, ashamed. "I just like to clean," I said. "And that's okay. I love having a cleaning lady. Hell, I'd like you to quit that silly job at the Best Buy and work for me full time. I really would. There are a lot of men who wear panties these days. Some of them wear dresses. I read an article today that wondered if sissification was a new sexual preference. So let me repeat: There is nothing in the world wrong with you putting on a dress and makeup every day and cleaning. Nothing. I'll help you if you want." I looked up at her. I shook my head. "Now, Louie, you know that it would be unethical for me to treat you. But I know another doctor who specializes in this stuff. Dr. Martin. He's a gender specialist. I've set up an appointment for you at 4 p.m. on Tuesdays. I love you, honey-bun. Just remember that. This isn't a marriage-threatening development. I'm not going beat you with a whip or cheat on you like in that magazine you have. Yeah, I read it. But whatever you need, I'm there. If you want to talk after your sessions -- non-professionally, of course -- I'm your wife." "I don't wear dresses," I whimpered. "I believe you, Louie. But i you need to think about whether you want to. If Dr. Martin decides you're a sissy, you need to think about the embarrassment and humiliation that comes along with this lifestyle. Are you ready for your friends to see in a dress? For your mother? Or do you want to see if Dr. Martin can cure of this." "I don't want to be a sissy," I said. Had I felt certain urges? "Help me, Cynthia. Please." * * * Theodore Martin's psychiatrist's office was large and intimidating. It was accented by wooden bookcases and leather chairs with diplomas on the the walls. There was a wedding photo and him and a brown-haired woman on his desk. "So, Louis. Tell me about yourself." "Um, I'm a normal guy," I said. "I grew up in Toledo, the only child of a single mom named Vanessa Jennings. We were middle-class, not rich and not poor. My mom was a secretary, but she did some cleaning for families for extra money." "Cleaning?" he said. "Yes sir," I said. "But if you're thinking it affected me, well, I was hardly ever around." "Still, it was something you knew that she did, right?" "Yes," I said. Dr. Martin wrote in his notebook. "Louis, your wife is concerned about you. She worries that you may be a sissy," he said. That word again. It haunted me. "I'm not," I said. He nodded. "Louis, did you ever wear your mother's clothing?" "No," I said. "Not really." "Not really?" "Well, maybe once or twice. You know. Kids being kids. I wore some of my sister's things." He smiled. "And did you like it?" "I can't remember," I said. "I mean, I didn't do it for long, so I guess not." "Louis, length doesn't measure desire. You could have had other factors stop you. A girlfriend. Getting caught. Joining a sports team. You see, transvestism can be a controlled urge for a growing boy. Some kids are helpless to fight it. And some can block it for years." "Dr. Martin, I don't dress anymore." "Ah, but when you did, what did you Feel? When you would look in the mirror at the girl there?" "I ... I felt pretty. I felt soft. I wanted to have sex with myself." He nodded. "That's all natural," he said. "Louis, we aren't one person. There is a girl inside you who wants out. She wants to paint her nails and wave to the world. Let her out, girly." "I'm just help out my wife cleaning the house," I kept saying. "That's all." "And that's a good thing, Louis. Don't let anyone tell you it's not. That's not why we're here. Now, tell me about your name. Louis Louis?" I shrugged. "My father's idea of being clever," I said. "It's an old rock 'n roll song. The Kingmen. You know, 'Me gotta go...no, no no.' Anyway, no one calls me that. I'm just Louie." "Did your mother comfort you about the name?" "Comfort me? I don't know. Probably. It's a goofy name." "Sometimes, small insecurities can feed into cross-dressing, Louis." We kept talking. About high school. About college. About meeting Cynthia. About her calling me her wife as a joke. About the Sissy magazine. Finally, he looked at his watch. "So, Doc," I said. "Am I broken?" He grinned. "It's too early to tell, Louis. Do you think you're broken." "I'm fine, Doc." "Well, here's what I want to do. I want these sessions to continue. We'll noodle around, and we'll see what conclusions there are, and we'll seek a treatment. If we indeed decide you're sissy and you want to stay sissy, that's fine. If you're sissy and you want to stop, we'll look for a way." I nodded. I hoped that he wouldn't jump to conclusions about me. There were so many transgender men. I just wasn't ready to admit that I was one of them. "Here's what I would like you to do in the next week. I think we have to see how women's clothing affects you. I think you and Cynthia should buy a couple of maid's dresses, and maybe one other dress. Maybe two. Something simple. You'll need underwear, bras and panties. Maybe some earrings if you don't mind getting your ears pierced. Makeup. Let's give this sissy stuff a try, and then we'll know better how to proceed." I looked at him. "But, Doctor. Why assume I'm a sissy?" "Louis, you've been dressing as a male for a lot of years. Let's give it a little while to go in the other direction. It's an experiment, nothing more. No one is assuming you're a sissy. We're just going consider all the possibilities. Just wear the dresses while you're cleaning. No one else is home then, right?" "No, Doc," I said. He nodded. "Then this will just be a trial run. No sweat." He rose. I rose. He handed me a list to follow for the next week. I exhaled, and walked out into a world that had changed. * * On Wednesday, The day after my session with Dr. Martin, Cynthia drove me to the uniform store. It was a small shop that thrived by selling outfits that policemen wore, and fireman, and nurses, and cheerleaders and school children. There were hospital scrubs and those uniforms worn by the waitresses at Japanese steak house. The clothes were in groups spread across the store. And in the left corner of the store were the maid's uniforms in various colors and various sizes. Cynthia picked up a medium, "This is ridiculous," I said. "Oh, lighten up, Louie," she said. "Think of it as just a bit of fun. A lot of guys wear these uniforms for excitement. Maybe you should try to be one of them." "Cynthia," I said. "That isn't funny." "Baby," she said. "I'm not making fun of you. I'm really not. But I am aware that a lot of men like to be maids. It's a real thing, psychologically speaking. This is treatment. Go along with it, Louie Louie. It's only for a few weeks." Cynthia had used my full name, which usually made me smile. My parents were weird, you see. Hell, if the dial had been turned, they might have named me La Bamba. Cynthia grabbed a pink dress and a pale blue one. She paused, then grabbed a black and a yellow. She picked out several bras and panties. There was a small hat -- a mop hat, it's called -- that came with the uniform. She took it to the cashier. He looked at the clothes, then at me, and he shook his head. "My husband will have to try on the dress," Cynthia said, and I died. "Most guys do," the cashier said. He looked at me. "The gays are very big at trying stuff on." Cynthia answered before I could. "What if he is gay?" she said. "What if he wants you to bend him over the counter and butt-fuck him right here? If you want to make a sale, I'd shut up." The cashier, a bald man, glowered at me. "The dressing rooms are over there, Priscilla," he said. We entered. "The nerve of that guy," Cynthia said. "Of him? You were the one who brought up butt-fucking," I said. "Oh, he couldn't handle a woman like you," Cynthia said, laughing. I tried to laugh, too. I held the dress up against my body. "It looks like it fits," Cynthia said. "Why don't you just slide it on quickly. We don't have to try on the underwear." "Jesus, Cynthia," I said. But I put it on, and it fit. It wasn't the sexy maid's dress that you see at Halloween. It was functional, basic. And, yes, I noticed that it was pretty. It felt short. It felt snug. And I was hard. That evening, Dr. Martin had given us permission to skip several steps. Beginning sissies always do. Step one: I shave my body. It felt strange, and it looked worse. My penis, for instance, looked like a pencil eraser. I tried Nair, but with mixed results. I cleaned up the patches of hair. Step two: I slid on my panties. Yes, MY panties. They were smooth and slick, and they felt nice. Bu they were much smaller than my men's briefs. The lace felt odd. In the rear, my butt was lifted and hugged. I liked them. Step three: I put on my bra. It might have been the strangest item of clothes, because I didn't have breasts. Well, not real ones, anyway. Still, I liked the way the straps felt across my back and shoulders. Steve four: I slid the breast forms into the bra. They were a b-cup, nothing too large. But I could feel their heft. It did surprise me the way my body heat warmed the silicone. I applied my makeup. I had trouble with my eyeliner, but I was amazed at how luscious my lips appeared. Step five: I stepped into the dress. It felt impossibly short, and the petticoats lifted the hem even higher. It was like wearing a long t- shirt with no pants. But it was form-fitting. I liked the way it hugged my bodice. Was this sissidom? I moved across the room, and Cynthia smiled at me. She said she thought I was pretty. I thought so, too. * I began to wear dresses daily, all the time. I know Dr. Martin had suggested I just wear them while I cleaned, but they felt too nice to take off. Pink and yellow and patterned and black and blue and white. I fell in love with heels. Lingerie was delicious. I realized I had been fighting women's clothing, but I was all in now. I was never without makeup or jewelry. I stopped objecting to the word "sissy." I started thing of myself in those terms. I copied Cynthia's movements, the way she touched her neck, the way she held her hands. I watched movies, and I identified with the women's role. On Tuesday, I walked into Dr. Martin's office carefully. I was wearing blue heels and a blue patterned sundress. dress. My makeup was complete. It had been a week, that's all. But my collection of maid's dresses had grown to eight. My ears had been pierced -- two holes on one side, three on the other. My perfume was sweet, lighter than the men's colognes I had worn. Dr. Martin smiled when he saw me. "Well, aren't you lovely?" he said. "I knew this was the right choice." "Do you think so?" I said. "Everything is happening so fast." "Are you kidding me? You were made for that dress. Tell me: Are all of your other dresses of the maid variety?" "All but this one, ," I said. "I don't really need regular dresses for my tryout, do I?" "I think you do," he said. "You're going to want to style your hair soon, and you may have to run out somewhere for a quick dinner or an errand. It's easier to put on a dress than to take off you makeup and wear a baseball cap. You know?" I thought for a minute. "I guess you're right," I said. "So how is Cynthia taking this? She's a colleague, you know." "I know," I said. "That's who recommended me to you." "Well, she's a lovely woman. Is she adjusting?" "She seems to be," I said. "Sometimes, she's a little too eager to help me along. She's like the wife in 'The Danish Girl." "Yes," he said. "Nice movie. Complete rubbish, of course. They sweetened up the story a lot." "Maybe," I said. "Hey, I should have brought pastries. Then I could look like the Girl With the Danish." Doctor Martin smiled. "So, how else has that affected you. Do you notice men more?" "Men? No, doc. I'm married." "People...change," he said. "The more feminine you become, the more you might admire masculinity. Nothing wrong with it." "No, no there isn't. But being with men isn't for me." Dr. Martin got a faraway look on his face. "Maybe it is," he said. Doctor Martin reached into his drawer. He brought out a stack of photographs. In them, sissies were pleasing their men. It was quite graphic. "Now," the doctor said. "Tell me which of these men you find the most attractive." "Um, really?" "It's you and me, Louie. Just tell me who's...impressive. Who rings your bell?" "Well, that guy is handsome, I guess." "And well-endowed," Doc Martin said. "And that one. He's nice." "Nice?" Doc Martin laughed. "He'd make a woman out of you." We kept looking. This guy was muscular and that one had a nice dick. This one looked straight and that one looked gay. This guy was bald and that one had a beard. "Doc, can we stop? I'm not comfortable." "Very well," he said. "I want you to take these home, though, and go over them with Cynthia. Compare notes. Girls do it all the time." "But I'm not..." "It's okay. Can I call you Louise? Now, here is your list for the coming week. Attack it, please, and I'll see you on Tuesday. * I glanced over Dr. Martin's notes, and I immediately blushed. I looked at the photos. This wasn't the shallow end of the pool any longer. This was full-blown sissy stuff. He had decided my feminine side was in control of me. I showed the photos to Cynthia. The I showed her my list. She had an outbreak of giggles. "He wants you to get all of this?" she asked me. "Well, I think we've graduated from cooking and cleaning. I'd call you a wanton woman, but I don't think you'll be wanting for anything." I blushed. We walked to the car, and we headed toward the Adult Book Store. Officially, it's called Playland, but everyone I know just calls it the Adult Book store. If you want a naughty DVD, or a sex toy, this is where you went. I looked at my list. Yeah, the Doc had assigned me more toys than Legoland. Step One: He wanted me to get a butt plug. Nothing too large. He had a three-inch model written down, glass with a flower at the base. It was pink. "You can go larger when you get used to it," the saleswoman told me confidentially. "You're going to love it. I have two of them." Step two: A chastity belt. This was fascinating to me. It had a tube where you put your penis in, and there was a ring that went behind your testicles. It pushed together, and you locked it with a tiny paddock. The purpose was that someone else -- Cynthia? -- held your key and as such, controlled your climaxes. But you had to trust the person to unlock you at the right time. If they did not, it could be torture. I decided my key holder was a very, very important person. Step three: A penis gag. This looked intimidating to me. It was a lockable gag that fit around your head. A three-inch penis gag then went into your mouth. The lockable part bothered me, the same as with the chastity belt. I didn't want to give up my freedoms, did I? Step four: A strap-on dildo. This was frightening. I knew even as Cynthia picked it up that it was designed to penetrate my asshole. It was six inches, but the clerk said they went up to 10 inches."Nothing makes a sissy feel more like a woman," she said. Cynthia seemed to like it, too. Step five: A collar and leash. This one embarrassed me, too. Probably because it was designed for the sissy on display. The mistress or master would put a dog's collar on you, or a small choker, and then lead you around like a pet. I gathered that not all sissies wore these. But they struck me as more for the controller than the sissy. We bought one of each, as well as a large jar of lubricant. The salesgirl looked over our chosen products and smiled. "You guys are getting into it, aren't you? she said. "Sweetie, you'll never go back to being a man. Congratulations." I blushed. My ass tingled in anticipation. * That night, Cynthia looked at me, dressed from head to toe. I was wearing the cage, and the plug was inserted. I didn't have the penis gag on, though. Not yet. "You are so beautiful," she said. "So exotic. So sexy." "I'm a freak," I said. "You are not," she said. "You're just unleashing your inner sissy. It's okay. So tell me, Louis. What are we going to call you?" "Well, I don't know," I said. "Doc called me Louise, but I don't like it." "Let's see," she thought about it. "How about Lulu? You know, for Louie-Louie. I like it. Don't you?" "Well, a little. Yeah. I like it." "Then you're Lulu. Little Lulu. It's a great maid's name. It's a great sissy name. Lulu. 'Lulu, could you bring me a cup of tea?'" I blushed. "Okay," I said. "No," Cynthia said. "You say 'Yes, Madam.'" I blushed. "Yes Madam," I said. "That's more like it, Lady Lulu. Now serve me." We took out the pictures. Instead of concentrating on the men, Cynthia was pointing out the sissies. Her dress and her apron, her heels and her makeup. I felt was if I was one of them. I put the penis gag on. It was hard to adjust to, but once I did, was nice. * It was Tuesday, time for another session with Dr. Martin. I was wearing a patterned sundress, blue and white. I had on blue heels and I carried a blue purse. I felt normal. If you had put me in jeans and a t-shirt, I would not have. "Hello ... Lulu," he said. "You heard, huh?" I said. "Yes. Cynthia and I were talking over lunch and she said you found a name you liked." "Oh. When did you guys have lunch?" "Yesterday," the Doc said. "We wanted to talk about you." "Oh," I said. "Is that all right, Lulu? Cynthia and I are close, and we're both close to you. So we had a sandwich. I like her, Lulu." "I see," I said. "Well, I'm not sure you do, Lulu. We're colleagues. We're friends." "I'm sorry. I tend to get a little jealous." "I certainly don't see why, Lulu. You're a sissy. I think we can safely say that now. You're more girl than boy. And that's okay. Tell me: How are your chores coming?" "They're fine, Doc. I still do them every day. They're very rewarding." Was that a smirk on his face? A sneer? It couldn't be. Dr. Martin was a professional. He was treating me. He was making me better. All of his meetings with Cynthia were about that, weren't they? So why did I have images of the naked in my head? "Are you wearing your toys?" he said. "I'm wearing the plug," I said. "And the cage. Cynthia has used the dildo on me twice. We haven't used the collar and leash. I wear the gag when I'm doing my chores." He nodded, as if he approved. "And how often do you go out?" he said. "Not often. I mean, I come here to meet with you. But we don't go out to eat or to the mall." "Why not?" he said. "It would be embarrassing," I said. "But isn't that the point? To feel that humiliation rise and be conquered?" "Um, I guess." He made notes in his pad. Then he handed me another list. And I slid a little farther. * This time, the demands on me were even worse. The toys were humbling enough. But evidently, Doc wanted some other people involved in my journey. There no longer seemed to be the option of stopping the momentum. It was just a matter of living the ride. Step one: Dr. Martin wanted Cynthia and me to go to a straight bar and sing Karaoke. The Bangles. The GoGos. They Supremes. Any girl group was allowed. He had us wear long, flowing silver gowns. We sang, and the guys in the crowd threw dollar bills at us. They gathered around us, and they kissed our cheeks. Soon enough, a couple of them kissed our lips. It was a little embarrassing, but it was a lot thrilling. Step two: We invited Jerry Ramsdale, an old golfing buddy of mine to dinner. I met him at the door in my black maid's dress. He did a double take, and then he acted as if I had leprosy. All through dinner, he talked mainly to Cynthia. Finally, he looked at me. "Louie, I'm sorry," he said. "This left me gobsmacked, to tell you the truth. I wasn't ready for an old buddy to meet me at the door in a dress." "It's okay, Jerry," I said. "I know what I am." "You're nice," he said. "I'm the ass. Now, tell me about this." And I did. I told him about the dresses and the toys and my shrink and my underwear. And we seemed to reclaim our friendship. When he left, he kissed my hand. He said he would call me. I felt validated, as if this lifestyle could work for me, after all. Step three: We had a dinner party for our families. This time, Cynthia had called people to warn them how I would be dressed and how they should speak to me. So it went over fairly well. My sister said she always knew from the days when I would wear her clothes. My mother-in-law asked Cynthia if she was now the man of the house. My father in law was trying to talk about the Packers. He seemed more upset that I couldn't talk football than that I was wearing a teal dress. We had a nice meal. My mother asked me to go shopping with her. She wanted some daughter time with me. They adjusted to me so fast. I had been scared to death, but the world really does move on. Step four: I hadn't worked much since my sessions with Dr. Martin started. But on Friday night, I walked into Best Buy wearing a gray skirt and a black blouse. I had on heels, and my forms were prominent. Jimmy, the night manager, walked up to me and told me I would have to talk to Human Resources if I wanted to work as a girl. There was no judgment, no hate. So I walked down to HR, and I made an appointment for Monday. 'I wish you luck," Jimmy said. "And by the way, I'd love to play with your titties." My jaw dropped. He had been so nice to me, and now he was coming onto me. To him, I supposed, it was the same thing. Step five: On Sunday, Cynthia and I went to church. Mind you, I hadn't been in church for years. I joked that the statue of Jesus was going to slap his cheeks, like in Home Alone, out of shock of seeing me. I wore an off-white dress with white heels and a white cloche hat. My makeup was subdued because of the surroundings. My earrings dangled. After the service, Father Mayhew greeted Cynthia, and he took both of my hands in his. He look at my face, trying to recognize the features. "Father, I haven't been here in a long time," I said. "Well, you're here now, young lady," he said. "You should come and see us more often. It's always great to see a pretty face." I smiled at him. He looked around, and he called a man over. Paul something-or-other. "Now," Father Mayhew said. "I think you two are perfect for each other. Go forth and multiply, you know." Cynthia started to laugh. I blushed. "Just a joke," Father Mayhew said. "But men and women do need each other. Paul's a nice man. Give him a chance. * * I was sinking deeper all the time. That's what I told Dr. Martin in our next session. I felt I was falling deeper into my feminine role, and there didn't seem to be a way out. He was pushing me deeper, and Cynthia was pushing me deeper. "How is Cynthia?" he interrupted. "Oh, she's...she's fine," I said. "A little distracted, but I suppose when your husband becomes a wife, that happens." "I suppose," he said. "At least she can go out and blow off a little steam every now and then." "Steam?" "You know," he said. "With her dancing." "What dancing?" Dr. Martin stopped in mid-sentence. He had said too much. Finally, he shrugged. "Well, Lulu, we've been out dancing a couple of times." "Dancing. You ... and my wife?" "Hey, you're the sissy," he said. "You abandoned her so you could wear dresses. She just had her needs. I was there for her." "You've been with my wife?" He shrugged. "I've been with a colleague of mine," he said. "It's none of your business if we had sex." "Sex? You had sex with Cynthia?" "Please calm down, Lulu. Please understand. You're a sissy. You can't make a woman very happy anymore. See it from her side. Her husband is a woman. When is the last time you penetrated her?" I felt like storming out. I felt like throwing a punch. I felt like crying. "She could have talked to me," I said softly. "And said what? Was she supposed to ask your permission to fuck someone she wanted to fuck? Was she supposed to borrow a bra before her big date? She's not evil, Lulu. She's just a healthy woman. Did you honestly think she would refuse sex forever while you minced around the room wearing the same lipstick she wears? While you got hard looking at pictures of naked men." I sat, softly sobbing. I looked up at him. "Was this all a con?" I asked. "Did you push me toward dresses so you could steal her from me?" "No, Lulu," he said. "Being a sissy is in you. If you think about it, you'll know it's true. Cynthia cares about you. She's just adjusting. Be fair. If you want, can blame me instead of her." "I better go," I said. "If you must," he said. "But I'd be careful of how to bring this up to Cynthia. She really is a lovely woman. She didn't set out to sleep around. It just happened." "What's next?" I said. "Well, that's up to you. I would suggest you stay the course. You're the one who looked at those dick pictures. Did you get aroused? You're the one who dyed your hair blond? Did it make you happy? Lulu, I have one final list for you. Pay attention or do not. And if you ever need me, well, I'm your doctor." I stood up. I smoothed my dress. I took a Kleenex from his desk and dabbed my eyes. * I didn't go home. Cynthia was there. I tried to understand a woman who felt abandoned by her husband to be a sissy. It must be a horrible, empty feeling. Still, I wasn't prepared to face her. I looked at Dr. Martin's list. I nodded to myself. And I headed to the bar. Randy's is a loud, crowded fetish bar on the West Side of Cincinnati. There are men and women of every stripe, gays and lesbians and bondage queens and sissies and people licking their own relatives in the mirror. I took a seat near the end of the bar and looked out at the cowboys and firefighters and schoolgirls. The bartender stopped, and I asked for a gin and tonic. I grinned. It was what I used to drink when I was a man. Now, I was a sissy. And I had a list in my hand. Step one. Give a blow job. Yes, I thought. I was ready. Guys loved blow jobs. It would be just like my penis gag, only bigger. I looked around. The bartender placed two gin-and-tonics in front of me. He motioned to my left. There was a young guy with long brown hair. I hoisted my glass in his direction. He slid off the bar and came over to me. "Hello, gorgeous," he said. I smiled at him. "Hey yourself," I said. "You on the prowl?" He laughed. "Not really. But I guess I was hoping to meet someone nice. Like you. I'm Anthony." I looked at him. "Lulu," I said. "Well, Lulu," he said. "You the prettiest girl here." I smiled. "Do you know what I am?" He shrugged. "Transgender? Yeah. I figured it out." "Does that bother you," I asked. "I'd say it thrills me," he said. We talked, and we danced, and we drank. We joked. We debated. And he kissed me right at the bar. I kissed him back. Then we were in a long, dark corridor outside the manager's office, kissing like horny teenagers. He was rubbing my sides. I had my hand on his cock. It felt like a light-saber. Okay, it was sleazy, sex in a public bar. But I fell to my knees and unzipped his jeans, and I sucked him off right there in the corridor. His back was pressed against the wall, and I bobbed with a purpose. I reminded myself to use plenty of tongue, and to nuzzle the balls. It was so good. He was so hard, thrusting into my mouth time and again. I loved the bulb. I loved the shaft. And then he was coming, driving his cock down my throat. I know it was my first time, but it didn't feel gay. It felt wild and raw and natural. It felt right. I was a sissy. This is what sissies do. One step down, four to go. Step two: I went back to the bar, and I sat there for the longest time. I looked at my list. Where was I going to find a lesbian? Well, right in front of me, it turned out. A woman with short, dark hair approached me. She loved into the chair next to me. She grinned. "Hi," she said. "I'm Margie. Buy you a drink?" "Hi, Margie. I'm Lulu." "You're just what I'm looking for Lulu," she whispered. "Are you sure?" I said. "I'm trans." "Really?' she said. "I could not tell. You're pretty." "Thanks, Margie," I said. "But listen, it's okay with me if you look for someone who is more your type." She put her hand on mine. "Who says you aren't my type?" she said, smiling. We ended up at her place, kissing and touching and enjoying each other. I had been married for years, remember. I knew what do with a woman, especially orally. She was thrown for a minute by my penis, but she twisted around and covered my face with her pussy. She smelled sweet, and she kissed like an angel. She pulled at my cage. "What is this?" she said. "It's prison," I said. "But you don't want that thing anyway. Come here." And she did. And it was glorious. Step Three: The morning crept through her blinds fiercely. I put the pillow over my face, then I threw the covers off and climbed out of bed. Margie was still asleep. She was gorgeous. I leaned over and kissed her hair. I dressed slowly. I knew I had to go home. I had been out all night. I needed to see Cynthia, even if it was for our final goodbyes. I hoped she wasn't with Dr. Martin. After the walk of shame -- and there are a lot of us in the morning -- I walked into the apartment. Cynthia was sitting at the table. She had been crying. "Did you fuck around?" she asked me. "I guess we both did," I said. "You went first." "Lulu, I am so sorry. Ted Martin is so tall, and so strong, and I felt so alone. He made me feel like a woman.There are no excuses. If you want a divorce, I'll give you one." The thing is, until that very moment, I was certain a divorce what I wanted. But seeing her vulnerable face, I questioned myself. "Cynthia, you hurt me," I said. "I thought you loved me, but all you wanted was him." "I do love you, Lulu. I swear. It wasn't about him. He was just ... convenient. There is no excuse. He convinced himself you were a sissy, and you needed guys. I went along with it. And I scratch my own itch." "Cynthia, I am a sissy," I said. "You were right." She looked at me. She wiped her eyes. "Do you have another list?" she said. "Yeah. He gave me one. I'm two steps into it." "Which steps?" I smiled. I pulled the sheet of paper out of my purse. "He wanted me to give a guy a blow job," I said. "I did that last night. He wanted me to go to bed with a woman." "What's left now?" Cynthia asked. "Let's see. Sex with a close friend, it says here. Who do you think? Jerry?" "I could see that," Cynthia said. "Jerry's sweet." "He wants me to have sex with another transsexual. He doesn't say male or female. Oh. And then there's you. The final item is 'Sex with your wife at the Hotel Royale.' That does sound nice." "Yes, Lulu. Yes, it does." She bit her bottom lip. "You know, sweetheart," Cynthia said. "We could still finish that list." I shrugged. "Can I start with you?" "Of course you can," she said. "But why do you think that's on the list?" "I don't know. Maybe the Doc really was trying to do the right thing. After all, could have pushed me into having sex with Father Mayhew." She laughed "Seriously, there are so many potential partners. Cops and ditch- diggers. Teachers and Republicans. Other trannies. Other races." "But I won?" Cynthia said. "You won," I said. "You had to win. You still have my damned key." "So what now?" She said. "I don't know. We've changed. Both of us. We are going to have to make...concessions to the other one. You need sex from a macho guy. I need to see this sissy thing through. We have to communicate, and we have to trust each other." "Yes," Cynthia said. "And right now, you have to get me a cup of coffee. Now, girl." I giggled. I curtsied. "Yes, ma'am," I said. "I love you," she said. "I love you, too." "You know, you really are a sissy," she said, laughing. "Yes," I said. "Your sissy." (c) 2019 by Cassandra Morgan

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In the whole school no student was more feared the Erin Hardy. Rumors aboud of students being beaten up, teachers threatened and confis**ted d**gs and weapons. The crowd Erin ran with were the baddest of the bad, whenever shit went down Erin was there she was the top dog. Surprised you didn't I?You didn't read that wrong, Erin Hardy the toughest Bitch at Mckinnley High was a girl. My dad was in the Air force and as such we moved quite a bit. In fact I had not set foot on Natural American soil...

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The Couple

His name was Matt and her name was Mary, a typical middle aged (46 and 43) couple living in a small city. Matt was an accountant and Mary was a housewife. They had 2 beautiful c***dren and they enjoyed spending all of their time with them. Everyday the same, waking up going to work, k**s at school and then back home having dinner all together and then Matt was watching tv on the sofa while Mary and the k**s were asleep by 11. One rainy Wednesday, everything were exactly the same for Matt and...

2 years ago
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Lilys last summer

Introduction: This is a romantic story I wrote. There wll be more parts later. No sex yet but I hope you will enjoy it. The paragraph in brackets is a flashback Lily woke up slowly from her bed. The morning light shone through her window giving her the illumination of a godess. She was smiling as she woke, her dream was good but she could not remember what it was. She looked over at her calander and remembered that it was the last day of school. She smiled and thought of the wonderful summer...

2 years ago
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Summer Vacations 8211 Part 4 Neelofar And Nazma

Hey. This is GrayWizard here with the 4th installment of my sex series ‘Summer Vacations’. So, let’s get on with the story. I am Vikas and for this Summer Vacation, I have come to my friend Vatsal’s home to get know his family and venture in Pune city. It’s been two weeks since I am here. On my way to Pune, I came across beautiful girl Neelofar whom I fucked on our train to Pune and later in a hotel. But my story had a twist a couple of days ago when Vatsal’s sister Ishani seduced me and we had...

3 years ago
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A Fresh StartChapter 20 Academic Plans

And that’s how we spent the entire Christmas break. Some days I would go over to Jeana’s, and we would screw our brains out, other days I would pick her up, we’d goof off, and then go back to my apartment and screw our brains out. Isn’t it just awful when you get in a rut like that? That first day at my apartment I told her what had happened to me at Christmas. Jeana was horrified, but for the first time really understood why I had to leave. School started up again, though, and we had to...

1 year ago
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New Beginning Part 1

She stood up across the bar. She stared at me. I looked at that golden blonde hair and those epic tits begging to be ripped out of that tight black dress. She licked her cherry red lips and I was sold. The drinks I had been drinking wasn't helping my impulsiveness either. I rush over to her. The music was loud in the bar so I could barely hear a word she said. She was really into me I could tell. I placed my leg on her smooth leg. She wanted me and her olive colored skinned glowed in my eyes....

She Males
2 years ago
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Quicky at the gym

The idea of this stranger pleasuring himself while looking at me in public turns me on a lot and with just that idea, my dick starts twitching after a minute or two of this going on. I feel my penis getting harder as I sense this stranger’s gaze on me and not long after, I'm fully erect. I haven't touched myself yet and I hear this man shuffling around; I open my eyes and suddenly realize someone else is walking in—just in time I grab my towel and cover myself. The other person coming in is...

3 years ago
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Felt Like A Whore That Night 8211 Part II

Hello all ISS readers. My name is Rajveer and I am 29 years old Bisexual bottoms guy from Bangalore. I am fair, with a height 5’7; average built and weigh about 80 Kg. I am a regular reader of ISS and been trying to post my story since a long time, but due to busy schedule I was not able to spare time to ink it. I am glad that finally I am writing my story which happened to me about 2 months back. I am on an adult dating site and one day I received a mail from a guy named Rajesh. He said he was...

Gay Male
2 years ago
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Jail Force Parts 19 20

Parts 19-20 By Jimmy T Seay (m+/t oral forced enema jail) =========================================================================== Bruno loved the feel of the boy's hot cum spraying on him, the air was scented with the smell of the boy's fresh load of cream. As Brian's nuts had jetted, Bruno felt the tight band of Brian's ass lips contract and expand. The boy's fuck chute was still nice and tight, it was deep and made for a good, powerful fucking. Bruno bent down,...

2 years ago
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Interview With A Domme

Interview.As Erica approached the destination for her appointment in the upscale middle class neighborhood, she had to admit to being a bit nervous and unsettled.  Nervous because this was her big break, her first solo feature article.  Over the past several years she had worked her way up from very local weekly papers, to being a cub reporter on the large daily newspaper, again assigned to the local news scene, to finally being promoted to a position as researcher and writer for the Life and...

1 year ago
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Lin and Lex a weekend away for free 1

Lin and Lex are girlfriends from first year in basic school - they like each other a lotLex and Lin are often out together and at parties, but never away for a full weekend yetLin and Lex differ in many things: their characters, looks as well as sexual preferences Let me introduce both to you: same size, small and slender, so sexy to see them together!Lex loves lovely looking ladies and lasses - great girls - best with firm big boobsLex loves lovely looking ladies and lasses - she is so shy -...

2 years ago
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Its Just Natural

My now wife Amanda was my first piece of ass. I was probably her thousandth, give or take a few hundred, with innumerable guys. She didn’t keep score because it wasn’t important to her. We were both eighteen when the above-mentioned event happened. It was our third date and I had been thinking it was time to make a move, from what I’d heard anyway. When I got her to a private place I was surprised to hear, “Don’t you think I’m sexy?” Stuttering, I replied, “I sure do! Why do you ask me...

2 years ago
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Better Than Before

Charlie thundered down the stairs and headed straight for the kitchen. A chorus of "hi Charlie's'" was quickly acknowledged. "Anyone seen Mike?" "No, I haven't seen him. Why don't you join us, c'mon, sit down." The 'us' was what Charlie referred to as the coven, a mixture of female relatives and neighbors that had long hounded Charlie about her tom-boy ways. Every year during the Superbowl they sat in here talking while the men, and Charlie, watched the game. It was Charlie's...

1 year ago
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In the Name of the Prophet

The majority of the highly polished tables were arranged in four rows, the two centre rows were set up so that the sixteen seats were facing each other in two equal rows, seats for sixteen very important people. Each position had a high leather backed chair and a set of gold writing implements next to a blotter pad. Alongside these desktop accoutrements stood a cut glass jug complete with matching tumbler, the jug was freshly filled with chilled water and a slice of lemon if the drinker had...

2 years ago
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Its My PartyChapter 101

Time: Sunday, October 3, 2019 2:58 PM Jessica stood trembling at the doorway of the immense kitchen area. The servos! She thought they were leading her to freedom. Instead they had delivered her to Ricardo! Or did she have that backwards? Across the kitchen on a steel counter Ricardo was lying with another women. Both were obviously naked, and Jessica could see a long pole keeping the woman’s knees far apart, with a chain that kept the pole vertical. Amber’s left leg was high in the air....

3 years ago
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A Stitch In TimeChapter 8

Ex Libris Salvatio. Do you like that? I made it up. I have no idea whether it's actually Latin, but it is my new motto. From books, salvation. Or more accurately in my case, from the library, salvation. A lot of people find solace in the library; heck, I'd found some pretty good solace in the library myself the day after Christmas. But salvation? That was a lot harder. Since Monday was a day off, for the students anyway, I decided to return the three library books I'd checked out, all of...

2 years ago
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Amazing Sex With Cousin

Hi friends! I hope that you all had a very great diwali this year. Mine was amazing too! I thought to write about it as well and help you relieve what I did on diwali. Read and shag! This is my first story on iss so I hope you like it, don’t forget to mail me at for any suggestions or to have some fun( ;) ). Let me first tell you something about myself. My name is Anirudh(22) I am working in mnc in pune.About my cousin, her name is radhika (20), she is not that sexy or hot but one look at her...

Incest
3 years ago
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Not Quite a White Knight Book 1Chapter 17 It Never Rains

Once she calmed down - in all that took about an hour and included some more tongue play above and below - I asked about her shopping trip where she met Darnel. That was easy enough. Then I got into details, starting with her purse. “You had a fake license, a little cash, no credit cards and no phone - like a refugee. I did not think wealthy American girls could do that. You purse was mainly a brush and makeup. Did they take the rest?” “Well, the money thing is all Mumszy, so I don’t spend...

4 years ago
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Hans Und Greta

The winter in the mountains had been harsh that year.Greta still clung to the belief that everything would work out if they just remained patient and let the winds of fate decide their future. Hans scoffed at the idea just like he had rejected the inclination to trust the dreaded witch. He loved his adopted sister more than life itself but sometimes she was so irritatingly “good” that he left her to her cleaning in the tiny hut and he visited the Gypsy girls in the nearby camp next to the...

Incest
1 year ago
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Old Friends

This is a work of (mostly) fiction....Phil and I were good friends at school, doing all sorts of things in the evenings, weekends and holidays. When we were about 15, I was at his house and his folks were out. We were sitting reading comics when he suddenly said, 'I dare you to undress me'..... Well, never one to resist a dare, I got up, walked up to him, unbuttoned his shirt and took it off. 'Carry on' he said, standing up. I undid his belt, then unfastened his trousers and slid them down. He...

3 years ago
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A Visit to Tripps ClubChapter 12

The next day my plan was set in motion. I found myself the passenger in a Polaris Ranger, cruising at what seemed like a speed faster than the off-road vehicle should be doing on the jungle path. The constant bumps and swerves might have been annoying if not for the female driver too my left. Her large breasts, barely contained by her bikini top, bounced and swayed, along with everything else! At the beginning of the ride, we chatted. But as the drive became more difficult, and our speed...

4 years ago
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The GauntletChapter 3

“I’m sorry, Jean, but it doesn’t seem to be working,” Marguerite said as she let his limp cock slip from her lips. “My jaw is tired, may I rest a bit?” “What?” Jean asked, sounding confused. His mind was adrift in another time. “It isn’t getting hard, my love, your cock,” Marguerite said, quickly pumping her hand on the flaccid flesh. Jean suddenly realized that his wife had been using her mouth to attempt to arouse him. Jean was in no mood for it and pushed her away. “If you were better...

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