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Flip-Flop By Cassandra Morgan In a small thatched hut in Borneo, I am sure they are talking about her. In a city office building in Nigeria, I am sure they are talking about her. In a backwoods shanty in Hawaii, I am sure they are talking about her. So, yeah, we were talking about her. My wife Debbie and I were sitting around, trying not to turn on the TV for one night, sipping coffee and talking about the world. And so she came up in our living room the same way she came up in yours. Caitlyn Jenner. Yes, she is beautiful, and she is brave, and for goodness sakes, we agreed that she deserved to be happy. She had certainly waited a lifetime to be her, and the haters could all go jump in the lake, for all Debbie and I cared. I know, I know. Her famous family has made some people scowl, and from what I've read, some of those are in the transgender community. But you don't take that step, with the whole world watching, unless you have to take that step. We talking about her Vanity Fair photo shoot, about the lightning and the photography and the choice of clothing. We talked about the reaction from the conservatives. We talked about RuPaul and Renee Richards and Laverne Cox and Some Like It Hot and Tootsie and Wong Fu. And then I let it slip. I didn't mean to. I just did. "I've done that, you know." Debbie sat up. Her eyes widened. She grinned. "You've dressed like a woman, Jack?" "Well, kind of," I said. "I worked for almost a year at Whammers in college as, well, as a waitress.." Debbie burst out laughing. "No way! Why didn't you ever tell me this before? I can see it, as little as you are. I always thought you were kind of girly." I shrugged. "It wasn't that big a deal," I said. "Just a wig and a bra under those little orange shorts and a t-shirt. And I am not girly, by the way." "Sure you are. Isn't Whammers a gay bar? Kind of a Hooters' ripoff?" "No, it's a tg bar," I said. "Lots of crossdressers. And chicken wings. Turns out, transexuals like chicken wings and beer, too." She giggled again. "And you were a chick?" "Yeah," I said. "Two semesters worth. I couldn't find a job anywhere else. It was that or drop out of school. So a friend of mine, Cheryl, got me a job. I worked under the name Jilly and schlepped tables. Like I said, it wasn't that big a deal." The silence hung in the room for a moment. I really didn't expect it to be a big deal. I thought she'd rib me a little big, and then we'd find another subject to talk about. I mean, I never wore dresses or skirts. I never went out. I certainly never took any of the guys up on their flirtations, and yeah, there were some. I never thought about being a girl for life. "Did you like it?" she finally said. "I guess." "You guess? You guess? My sissy husband was a girl for a fucking year, and she guesses she liked it?" "He," I said. "Huh?" "He. You said she. I'm a he. And I'm not a sissy." "Well, maybe you are and maybe you aren't, girlfriend. Tell me. Did you wear panties?" "Yes. I had to. The shorts were too tight for boxers." "And a bra?" "Yes, but I had to give the impression..." "And falsies?" "Yes. Breast forms." "Lipstick?" "I had to wear makeup," I sighed. She sat back and laughed. She was always taller than me, 5-10 to my 5-7. But the moment seemed to shrink me. I felt small. I felt helpless. "My God, Jack. You were a girl. You were a crossdresser, no matter how you justify it. Did you sleep with guys? Did you suck cocks?" "No, Deb. I never slept with guys. I'm straight." "Well, maybe you're a little crooked," she laughed. She clapped her hands in glee. "Did you wear dresses?" "No, Deb." "Did you want boobies?" "Deb!" And on it went. Debbie seemed fascinated beyond the normal by my waitress job, by what I was thinking (I needed money), by what I was feeling (it was nice, and a little kinky, to tell the truth), by who knew (no one), by whether I was ever attracted to guys (no), by whether I had ever fooled around with a girl while I was dressed (no), by whether I wore heels (yes), by whether I wore pantyhose (yes), by whether I shaved my legs (yes), by how I got started (a job posting on the student bulletin board), by why I stopped (better job), whether anyone I knew ever came in (once, a science teacher named Mr. Jernigan), whether I ever fooled around with another waitress (no)." She saw it something sexual. I saw it as low wages and tips. She kept referring to me as a sissy. I kept telling her I needed a job. She saw it as erotic. I saw it as a different work uniform. Look, we've all had bad jobs. Life is designed for young people to get the shit work. Working on farms. Working in construction. Working at hamburger joints. Stocking in a grocery store. Loading lumber. I once cleaned up the sticky floors of a theatre, which is a far messier job than you'd think. And, yeah, for a few months, I was Jilly the waitress. For some reason, it seemed like a bigger deal to her than to me. She continued to pepper me with questions. Had I ever dressed since? (No). Did I miss it. (No). Did I consider myself a cross-dresser? (No.) How big were my breast forms (a C cup). Did I ever wear my mother's clothes? (No.) Did I like heels? (A little.) Did I ever hear from an old co-worker (No, not even Cheryl). Did I want a Prom dress? (No.) Would I like to dress up right now? (No, thank you). Did my co-workers think I was gay? (Probably). Did I ever think I would wear panties again? (Probably not). Did I get sexually aroused in my panties (Not often). That answer seemed to get her interest. She walked over to me. She stroked my face. She traced my lips with her finger. And she attacked me. Debbie was unleashed. She was on top, and her hands were everywhere. Her hair hung down over her face. She pulled her blouse off. I cupped her boobs and her erect nipples. She tugged at her skirt, then her panties. Then she slip up me and straddled my face. "Eat me, girlfriend," she whispered. "Be my bitch." She grinded on my face until I was gasping for air. She hunched me hard. She was the male of the species. She was the conqueror. She had never been like this, not on our wedding night, not on our first time. She was hunger itself. It was like it was the first time she had ever made love, and it was like it was the last time she would ever get to. I was hanging on. This was her show, her moment. I was just a convenient piece of meat. "You fucking sissy," she growled. "I love you, you fucking sissy." *** I woke up sideways on the bed the next morning, my feet dangling off the edge. Debbie's hands were on my breasts, not that there was anything there. I stood and started toward the bathroom. I felt a little wobbly, to tell you the truth. I took two steps, and I heard her husky morning voice. "Hey, fairy plum," she said. "Can you make me a cup of coffee?" Fairy? I told her I would. I started to look for my pants. "Just put on my robe," she said. I looked at it hanging by the bed. It was burgundy with blue paisleys, a particularly girlish robe. I kept looking. "Just put on the damn robe, sissy boy," she said. I started to protest. I stopped. I put on the robe. It felt delicate, like a soft breath across my body. It felt girly. I put on the coffee. While I was thinking about it, I threw a couple of bagels into the toaster. I cut some cream cheese and spooned some jam into a bowl. I put it all on a serving tray to bring to her. No sense in not being nice. "That's my girl," she said when I entered the room. I blushed. "I'm no girl," I said. "You could fool me," she laughed. She sat up on the bed. I set on the edge. And immediately, the questions started again. Did I have pictures? (No.) Would I like to take some? (No). Do I wish my hair was long enough for rollers? (No.) Had I ever worn a tampon (No.) Did I ever dress for anyone else? (No.) Did I wear my panties around campus? (I didn't think so). Did I ever think about it? (Sometimes.) Was I gay? (Hell no.) Did I shave my body then? (Of course). She felt my chest. "Did you ever sleep in your tits?" she asked. "Deb, stop." "Tell me." "I'm sure I did. We worked late. I'm sure I just collapsed some nights." "Did you have a nightie?" "No, Deb." "A shame. The most comfortable thing in the world to sleep in. Better than being naked." "I'll trust you." "Who would you have slept with? I mean, if you give in to temptation and went home with someone?" "There was no temptation," I said. "Jilly! Tell me." "Well, we had a bartender named Luke. He was a good-looking guy, I guess." "So it would have been a guy?" "I thought that's what you meant, since I was a girl..." "I didn't specify a guy, Jilly. Luke, huh? You wanted his cock? You wanted to feel him cum in your mouth?" "Deb, you're being silly." "Am I?" she said, grinning. "Silly like when I married a transvestite?" "Deb, I'm not a transvestite." "Maybe a little bit? I scowled. Finally, she stood. "I want to see," she said. "You want to see what?" "I want to see her. What did you say your name was? Jilly? As in Jack and Jilly went up the hilly?" "Debbie, please. Let it go. I'm sorry I said anything." "Come on, baby. Show me." "I don't have my old uniform." "Well, we can make do. I've got a t-shirt. I've got some shorts. It's just you and me, maybe. I'm not asking you to get a sex change." Finally, to stop all the conversation and all of the questions, I agreed. I trudged into the bedroom. I pulled off my shirt. Debbie rubbed my chest. "You don't have any chest hair," she said, as if discovering that for the first time. "But you're going to have to remove it from under your arms. And your legs. And your forearms." "Can't we just put on the clothes?" "No, no," she said. "You have to look right. This is Jilly's coming-out party. Lipstick. Mascara. The whole nine yards." I sighed. She was not turning loose of this. I walked into the bathroom. I rummaged for an new razor blade. Soon, the hair was gone. My whole body was a baby's butt. She handed me a soft yellow pair of panties and a matching bra. I sighed. I fastened the bra and spun it around. She rolled up pantyhose and stuffed them into the cups. She gave me a lavender t-shirt with a glittery unicorn on the front. Pantyhose. A pair of tight white shorts. Back in college, I had learned to do my makeup. But Debbie did it now. She fussed with the eyes for the longest time. She put a coat of dark lipstick on my lips. She didn't have a wig. She had me put on a pair of lavender pumps to match my t-shirt. She plucked at my eyebrows. Finally, she stood in front of me and admired her work. "Nice, nice," she said. "Jilly is a babe." I felt silly, the way I used to feel. But nice. The panties were electric on my penis, and it quickly stiffened. The bra felt wonderfully restrictive. The hose were like heaven. Had it always felt like that? Was I so easily aroused back in the day? Debbie reached out and touched my breast. She smiled. Then she she moved closer. We kissed softly. It was sweet. Then she kissed me harder. She pushed me onto the bed, then clambered over me, rubbing her crotch into mine. It was so erotic to feel our breasts crush against each others, to feel our legs intertwine, to exchange our lipstick. I never understood why some women like their husbands to dress up. Now I knew. It wasn't just for his pleasure. It was for hers, too. Deb approached me. She gripped the sides of my head and forced my face into his crotch. But there was nothing gentle about it, nothing nurturing. This was a full-on face fuck. I could barely breathe. She grinded my face into her like stubbing out a cigarette. It didn't matter that we had spent an hour doing my makeup. In seconds, she wiped it all off in her juices. "God," she said out loud. "I wish I had a dick." At the moment, in my heart, in my deepest soul where my secrets are buried, I wished she did, too. *** The next morning, Debbie and I woke up facing different directions, with my head near the foot of the bed and hers near the head. The room was wrecked. Debbie twisted around, kissed me and put her hand on my right breast. It felt nice. "Morning, Jilly," she said. "Jack," I said. "Jilly," she repeated. I shook my head and got up to go to the bathroom. "Hey, Sugar Tits," she said. "Make me some hot tea this morning?" Sugar tits? I didn't say anything. I peed, and then I went, nude, to the kitchen. I made tea this time. I got sweetener and cream. I made English Muffins this time. I was trying to keep her calm, keep her happy. I'll be honest. I thought she was on the edge of going bonkers. "Ah, good help is hard to find," Debbie said, snickering as I entered. "Gonna have to get you a maid's uniform to serve in. I bet you'd look hot." "Funny," I said, putting the tray across her lap. "Last night was intense, baby," she said between bites. "It was amazing." "Yes, it was," I said. "I don't think I've ever seen you that ... ravenous. You were Attila the Hun." She laughed. "I've never had a wife before," she said. "I think I like it." I spoke carefully. I had been thinking about this. "A lot of people find fetishes they like," I shrugged. "You think that, deep down, you like girls? Do you want a wife, or do you want me to be your wife?" "You want to know a secret?" she said. "I've always wanted to be a guy. I'd love to have my own dick to plunge into you. I'd love to have huge arms and a flat chest. A beard. It's been that way since I played volleyball. Guys have it made. I think thinking of you as a girl, thinking of you underneath me, just set me off. "Now, I like dick. But I have to admit that I liked being on top. I liked seeing you in panties. Look, I've been your woman for five years. I think it's your turn to be mine." I didn't say anything. "Jilly? I may want sex like that again." I looked at the floor. What's was the big deal? The clothes were just cloth, in a room where no one looked, with a partner who was my wife. Still, something felt ominous here, as if a door was being opened you could never again close. "Jilly. I'm going to go to the mall. Why don't you make the beds and do the laundry? I'll be back in a while." Make the beds? Do the laundry? I guess it must be my turn. I hadn't done them in a while. But there was something imperious about her tone. It was like she was telling me to do them. "And Jilly? Why don't you wear a dress while you clean up? You know, an old one of mine?" I swallowed hard. I didn't understand. Deb wasn't even going to be here. Why did it matter to her what I wore? "Yes, ma'am," I said without thinking. "Good girl," she said. "This is going to a good time for us, Jilly. I can feel it." She picked up her keys. She grabbed her purse. And when she closed the door, I felt like it was on my manhood. *** By now, I don't have to tell you where this was leading me. Despite the job, despite the makeup, I had not been a sissy in college. But, quick as a heartbeat, I seemed to becoming one now. Was I walking that direction, or was I being pushed? I don't know. Deb was really into this. All she talked about, all she planned. She even started calling herself Dev, as in Devon, instead of Deb, or Debbie. But mine wasn't the only transition going on in our house. She was changing, too. She was wearing pants all the time. Boxers. She was drinking beer and watching baseball. When we went somewhere, she had to drive. She was more aggressive, more mannish. I don't know much about female-to-male transexuals. I don't know if that's really what a shrink would diagnose Deb, er, Dev as being. But as she pushed me toward a female persona, she was gravitating toward the male. I expected her to start peeing standing up any day now. Take that first day, for instance. Dev spent six hours at the mall that day, and when she came back, the first thing I noticed was that she had whacked off her beautiful brown hair. It was short, a page-boy cut. Very butch. No makeup at all. She dumped an armful of packages on the couch. "Presents for my wife," she said. "Deb. Dev, let's don't do this." "Oh, shush, little girl. You get me wound up all day long, and you make me spend money on you. Just be my pretty. Okay?" I stood in front of her, wearing a blue dress I had found in the back of her closet. I had put her underwear from last night on, just so she wouldn't get angry. I looked silly in my sneakers and short hair. I looked like a little boy playing dress-up. "How do you like it," she said, talking about her hair. "It's ... it's a big change," I said. "It's kind of butch, but you know, I think I like it. I was tired of being so girly. Besides, I have you for that." "Sweetie, what's going on?" "Nothing is going on, Jilly. I just thought I'd turn Jilly Bean loose for a while. And maybe Deb, too. Come on. It'll be fun. Let's swap roles for a while." "Excuse me?" "I've been thinking. I'd like to be a guy for a while, Jilly. Just to try it. When you told me you were a waitress last night, something switched on in me. I felt like growing a beard and scratching my balls, you know. Now, I can't do either of those, but I'm going to like being the husband for a while. What do they call that?" "They call that transvestism. Female to male. Do you really want to be a boy?" "Well, maybe we'll be ships passing in the night on the way to the opposite sex. That would be a kink. I can't wait for our friends to find out." I groaned. "Now come here. I bought you a wig. Some makeup. A couple of maid's dresses. Some heels. Some underwear..." Maid's dresses? What? "Well, you wore a uniform at Whammers." "It was shorts!" "Damn it, I cut my hair for you. You will do this for me. It'll be a nice little diversion for us, baby. You'll like you. You'll see. Just for a couple of weeks." "Dev, you're turning me into a woman." "Wasn't part of you already there, Jilly? When I called you my bitch the other night, you loved it. Don't lie." "Dev, we were having sex. I'd love anything then." "See! You'll love this, too, Jilly Bean. Now quit being silly and get dressed." I looked at the maid's dress in front of me. It was gray with black piping. The other one was black with white trim. I exhaled. "Do you want me to wear one of these for dinner?" I said. "I want you to wear the gray one while you make dinner," Dev said. "Now be a good wife and get to it. By the way, make extra. Your mom's coming." "What?" "I'm just kidding, baby. It's way too soon to have your mother over and have her see you in a dress." "Thank God." "She's not coming til tomorrow," Dev said. *** The next day was Sunday, and I spent the entire morning in prayer. I kept praying my mom would come down with flu, or get hit by a bicyclist, or get swept away by Fabio. Something. I begged Dev to let me wear men's clothing. No, she said. I begged her to let me wear a women's pants. No, she said. I begged her to let me where a simple skirt and blouse, which still would have outed me to the woman who birthed me. No, she said. To Dev, this was Freedom Day. This was the day my family was going to find out that we had a female-led marriage. This was the day they were going to find out I was a sissy. And so the afternoon grew. The clock sounded like a time-bomb. I sat there, in my black maid's dress, with a white apron and a white mop hat, with black heels and fish-net stockings, with red lipstick and fingernail polish, with a blonde wig and false breasts. I was dying inside. I hated the thought of going outside, but I would walk across Times Square rather than have my mother visit. Finally, the doorbell rang. I looked pleadingly at Dev, who was wearing a white shirt and a blue blazer. She nodded. Showtime. I answered the door. My mother, my sainted mother, was standing there, her mouth open. She had been holding a cake for dessert, but now, it was on the floor. I had hoped she might mistake me for a stranger, but there was none of that. She recognized her son right away. "Holy shit!" she said. "Won't you come in, mother dear?" I said softly, standing to the side. "Holy shit!" she repeated. "Mother, you don't swear." "Holy shit!" she said, one more time. "Maggie! Won't you please come in?" Dev said. "Come into our home. Jilly has prepared a fine roast. We could talk, but I'm afraid of spoiling the meal. Why don't we sit down?" My mother looked at Dev's haircut, then at my breasts, then at Deb's sports coat, then at my stockings, then at Dev's shoes, then at my heels. She might as well have been dropped onto a foreign planet where goats had three heads and the sky was red and dogs were made of cheese. Deb escorted her to the couch, sat her down, handed her a brandy. My mother didn't drink as far as I knew, but she knocked that back and held her glass out for another. I went to fetch it. "Are you two fags?" she finally said. "Well, only sometimes, Maggie," Dev said. "Jilly likes a little cock now and then, but I'm trying to stop. Mainly, we just did a flip-flop with our lives. We're reversing gender roles for the sake of our mental health. You know what it's like. I'm sure there were times you wanted to wear the pants. Right?" I glared at Dev. Why would she...he tell my mother that I liked oral sex with men? "Well, I guess I always knew that Jack was gay. He couldn't help it. Even when he was little, he liked boys." Huh? "He was always so little, always so girly. When he played with other little boys, I always wondered if they were his boyfriends. Once, when he was in college, I went to see him, and he had traces of fingernail polish on his nails. And you, Deb. I always thought you were, what do they call it, a butch?" Dev smiled. "It is great that she has a mother who will support her if she winds up with a man," he said. "I think that worried her most of all." Mom looked at me. She looked up and down. She rolled her eyes. "You gonna get tits?" she said. "You gonna get a pussy?" Dev broke out into laugher. I blushed. "Well," mom said. "Are you?" *** I was miffed. I had been exposed to my mother, of all people. She would never look at her son the same way. To her, I was a freak, a cock-sucking sissy. There would never be a time, not Christmas, not Easter, not Mother's Day, when she would look at me and not imagine me on my knees. I went to bed silently. I put my white nightgown on, took my makeup off. I lay down. How could Dev do this me? Why couldn't we break things to people we love slowly, carefully. Sure, if this is to go on, everyone would find out. But let it be on our terms, not theirs. I lay down and stared at the wall. Dev touched me on the arm, tenderly. I ignored the hand. I felt it drift down to my hip. I felt Dev kiss my neck. "I love you," Dev whispered. "Who's my girl?" I said nothing. I just stared ahead. I felt the hem of my nightgown being lifted. I felt something...firm against my ass. What? I sat up and looked down. There was a protrusion from Dev's groin. A penis. It was erect and angry. The catalogues call it a Packer, an artificial penis. A lot of FTM transsexuals wear them. Some of them are just to pee through. Some of them are for sex. The most expensive ones are for both. Pretty much, it's a dildo an FTM can wear all the time, for standing while urinating or for having sex. "Do you like it?" Dev whispered. My eyes widened. I knew I shouldn't like it, but it was beautiful. I reached out tentatively and touched it. I had never touched another penis, even an artificial one. I grew erect. My eyes softened. All of these strange, mixed up feelings poured through me. God help me, I wanted to kiss it. Maybe I was beaten. Despite all my denials, maybe I was a sissy after all. "Touch it," Dev said. "Kiss it." I sucked in my breath. This was a big moment for me. If I kissed it, I was surrendering. I was her sissy to take and to have. Dev would be the main in our marriage. I would be her fucktoy. I leaned down. I looked at the tiny slit, at the artificial veins, at the dangling testicles. Shouldn't all of that gross me out? I lightly kissed it. I ran my tongue over the shaft. I looked up at my smiling... husband. Now, there are no real nerve endings in a Packer. A FTM does get some stimulation from the base of it, but much of the pleasure is via sight. It is a wonderful thing to see your lover treat it like a real penis. As angry as I was, I was fascinated. Dev slid a pillow under my back. He hiked my legs up high to open my anus and lubed me heavily.I felt pressure, then pain, then pleasure, then paradise. Then Dev was in rhythm, screwing me. I felt like a woman. In the glimmer, Dev looked like a man with breasts. This was when it works, I thought. This was when it wasn't about clothing or names or roleplaying. This was when it was two people who loved each other. This wasn't about cheating, about getting a stranger in the sack and making the other party watch. This was about us finding whatever trappings worked for us and embracing them. I kissed Dev passionately. This marriage wanted me to be the wife? Fine. I would be the wife. I would grow tits. I would wear dresses. I would wash dishes. This was our time. I finally felt comfortable with who we had become. And by the way, have you ever noticed what a delicious word "sissy" is? For a week, we went on as if life made sense. Every morning, I would rise early, before dawn. I would dress quietly. I would do my makeup and put on my my maid's dress. I would pad barefoot to the kitchen and start breakfast. Then I would put on my hose and heels. If I had time, I would style my wig. Look, I've read the stories. This is supposed to take months of subliminal coercion. A guy is supposed to be seduced in dresses, wooed into makeup, romanced into jewelry. Me? It happened all at once. It was ridiculously fast, absurdly sudden. I know there are sissies who are forced into this, who are caned, who are caged, who are castrated. That wasn't me. The worst you could say is that I had someone who loved me nudging me. There was no sexual punishment. There was no cuckolding. Was there part of me that wanted this? Or part of Dev that was pushing me toward it? A bit of both? She would not take trousers off. I hadn't worn them since that first night. Was this about the clothing? Or was it about Dev taking control of our lives, asserting her as the male of the species and subjugating me to the female. I wondered if she had a problem with obsession. She was so quick to pounce upon my information that I had worked as a waitress. It was like she was waiting for an opening to push me toward sissification. These days, I was thinking a lot about those days. Was I blocking any old feelings? I really didn't think so. There were no days of holding dresses up against my body. There were no sidelong glances at the men who came in looking for gender outlaws. Oh, the underwear felt nice. Of course it did. Panties were like dragging fireworks across your dick. Even without your own breasts, a bra felt comforting, maternal. Pantyhose were like a lover stroking your legs It was late in the evening one night, and all the chores had been done, and Dev was asleep on the couch. Too much beer, I guess. I walked into the bathroom. I looked at my reflection. I thought I was cute. No movie actress maybe, but cute. I ran my fingers through the hair of my wig. I touched my pouty lips. I ran my hands down my side, feeling my maid's dress embrace me. I turned to the side. My breast forms looked good. Was it wrong to admire one's own reflection? I felt forced into this, remember? I felt trapped. But there was a comfort in knowing that I passed, in knowing that I was desirable. Good legs, I thought. Nice butt. Dev was behind me now I guess she had woke up. She put her arms around me. She kissed my neck. Her fingertips traced the side of my breasts. "I wish they were real," she whispered. I bit my lip. I didn't want to admit that I did, too. But that's what I was thinking. The realization of it was as if I had been tasered. I was accepting this, wasn't I? I was starting to enjoy it. Maybe I should forget about those days at Whammers. They had nothing to do with this. Dev had feminized me. That was fact. She turned me. She leaned down and kissed me. She put her fingers to my lips. She was holding a pill in her fingers. I looked at her, questioning. She nodded. I stuck out my tongue. Like sacrament, she placed the pill there. I swallowed it dry. I was helpless. I knew that now. I would become more feminine as the days went along. Dev would be more masculine. Our wedding picture was on our bedroom wall. In those days, I looked young and eager for life to begin. Dev...Deb looked sweet and innocent. I imagined myself in the wedding dress. I imagined Dev in the tux. I smiled. Next time, I thought. *** It was a Thursday, I think, when I came into the apartment with my arm full of grocery bags. I called out to Dev, and I was ranting about a driver who had cut me off in traffic and what assholes some people are. And there she sat. Cheryl. I hadn't seen her since college. She had been a great friend back then, a confident, someone to teach me about makeup and hair flirting for tips. She had worked with me at Whammers. "Look who I found," Dev beamed. "The old friend you're always talking about. Turns out, she lives in town! Cheryl's a banker now." Cheryl was looking at me, smirking. Oh, she had seen me dozens of times in my old Whammers uniform. Now, all this time later, and I was still in panties. Some things never change. "I knew you would always be a girl," she said. Dev sat down across from her. He grinned. "So tell me about my Jilly." Cheryl smiled. "She was the sweetest girl you ever met, Dev. So soft. So pretty. So funny. If she hadn't had her thingie, she would have been perfect." I sat down, listening. I pulled my hem down toward my knees. My maid's dress felt awfully short all of a sudden. "Dev, I don't know where you guys are now, sexually. But back then, our Jilly was ... confused. I always thought she was gay, and we had this bartender who had a crush on her..." "Luke?" Dev asked. "Luke," she said. "He wanted her so badly. A lot of us thought he got her at a Christmas party one year. It was just the two of them." "...he kissed me." I remembered. "I had forgotten that." "God, I never would have," Cheryl said. "Why were you working there, Cheryl?" "Oh, it was a rainbow bar," she said. "I was in my formative years as a lesbian back then. I was finding myself, too. I'll have to introduce to Missy sometime. She's my sweetie. But you know what, Dev? Jilly never judged me. She was my friend. I hope she still is." I nodded. "Jilly was so repressed back then. She would not allow herself to be with a guy. It was a line she wasn't going to cross as bad as she needed to. Just once, Dev. Just once, and she would have been the biggest cock hound in Ohio. I'm sure of it. But that first taste is hard for some. She's lucky she had you to prod her a bit, to make her come out of her shell. She's a lovely woman." "Yes," Dev said. "She is." She reached out. She took my hand. My man. *** We began to go out. We ran into old friends, and to my face, all of them were gracious. God knows what they were saying behind my back. To be blunt, I didn't care. I increased my hormone pills. I used estrogen cream every morning. And Dev? He was growing more into a man every day. He got ahold of some theatrical makeup, and he now wore a small mustache and beard. If you didn't look hard at his chest, you'd never know. Oh, I didn't want him to remove his small breasts. I loved them. And despite all the stories about how a domme uses her sissy, there were still nights when my lover would climb on me, would force my nearly forgotten penis into her. It was a different marriage, I know. But it was a good one. One day, Dev looked across the breakfast table at me. "Can I ask you something, Jilly?" she said quietly. "You can ask me anything, sweetie," I said. "Am I enough for you?" "What? Don't be silly. Of course you are. You're my Wonder-Dick." "I was wondering," he said. "Do you want...other partners?" I was quiet. I touched her hand. My looked so delicate next to hers. "What do you want, Dev?" I said. "I want you to be happy. That's all. You keep getting more and more feminine, and I wondered. Do you want a real cock? We could have a threesome. We could go to the fetish bars if you want. We could get a guy. Or a couple. We could get a transvestite." "Sweetheart, you're all the man I need," I said. "If you want to open that door, you know I'll do anything you want. But I don't have to have a real man. I've got a real man. I don't need someone else to make me happy. I am happy. I'm your wife." And I was. Did all of this happen because Dev wanted to be a man? Or because, deep down, I wanted to be a woman? It didn't matter anymore. I sank to my knees. I reached up and unbuckled Dev's belt. This was going to be good. (c) Cassandra Morgan

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Kailani Kai is a hot milf with a huge pair of tits and a giant booty. This week, we linked up with her to have her show us her perfect attributes. She played with her tits in the bathtub. Later, we called our boy Johnny the Kid over to show her a good time. We decided to switch things up a little bit, and we had Kailani take control over the situation. Kailani started dictating exactly what she wanted. She shoved his face into her tits. From there, she had Johnny fuck her in several different...

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Cindy has a Biker

Cindy had been looking for a new job for sometime after been asked to leave her previous job due to her fucking her boss' husband. After sending out numerous CV’s she eventually got a job as an assistant at a publishing company. On her first day, Cindy overslept. She’d lain awake the night before, going over and over the tight morning routine in her mind. In spite of her preparations, the alarm had not been put forward an hour due to the time change. Cindy got dressed quickly with the...

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Cheerleader CampChapter 13 The Girls Graduate

June had arrived and brought with it the high school graduation. Kim and Sandy would be graduating with honors and they had both been accepted at my alma mater, University of Houston and would be going for a degree in electrical engineering. Being an EE myself, I was as proud as could be. Engineering, being a male dominated field, is going to take a lot of hard work to break into, but I am sure that the girls will make it since they both are hard workers. Senior prom was a gala affair with a...

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The Utterly Exhausting Beguiling CassieChapter 6 Friday One Week Later

SITTING ON A HARD wooden bench and shifting uncomfortably as my butt slowly turned numb, I watched Cassie rehearse a modern ballet, Roland Petit's "Pink Floyd Ballet." I admired the movement of Cassie's slender body clad in what looked to me like skin-tight light-gray yoga pants, yellow leg warmers and a loose yellow cotton top. I was quite immobile as she treated me to body swoops, bends, arms forming waves, toes pointed, fingers talking. The incredible Pink Floyd's Dark Side of The...

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A Married Mother Tastes Life On The Other Side

This story is another example of my secret lesbian lifestyle that I have now been involved in for the past 6 years. Still to this day my husband doesn't know that I have been having an affair with another woman, our real estate agent and my best friend. This has been the best 6 years of my life both physically and mentally. Up until now I had only ever been with one woman Jillian. But that changed on a business trip to Sydney recently. I live on the Gold Coast in Australia and work for a...

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Learning The Ropes

Introduction: Our very own Pup learns what it takes to move up in rank in the Sub.. If you happen to have played the game Rage then just imagine the setting as such. Imagine this as an awesome post-apocalypse sort of thing. — Rise and shine, kid. I heard the voice repeat this a couple times before I felt a hard punch in the arm. I sat up instantly. Ow! What was that fo- for .. The man who looked back at me was not someone I knew. He had short, finely trimmed greying hair and a thick face...

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Toman of the Cherokee 23

Gwendydd - sister Morgenau - brother Morial - brother Morien - brother Mordaf - brother - Naci's father New Council Members ___________________ Pikon Corth Groton Tydeth Docal Clondal - female Lyndeth - female Creton _________________________ "I need all of you out here right now!" Ukobach was growling as he concentrated. "We can end the last obstacle to the council ruling the magic dimension forever!" I looked at Ukobach, almost feeling sorry for him, almost....

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The conference1

I am 5’8”, quite Amazonian in build with large breasts, sex lately had been rather boring, I had had a couple of casual relationships with men but nothing seemed to hit the spot. I was summonsed to the boss’s office and was instructed to attend a two day conference staying over at the facility’s hotel. I was to go with Stacey one of the dizzy girls from the other office. I picked up Stacey and drove to the venue that afternoon, I endured her chatting away in the car non-stop on the two...

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An Old Friend

The weekends for John is really boring at times. The entire week is is pretty eventful with everyone around all the time making the lonely weekends hard to pass by. Most weekends for John is spent sleeping or watching netflix. Fearing this weekend will be something very similar, he decides to go for some some shopping from a nearby supermarket. He never like doing groceries and with these new apps delivering to your doorsteps life could not have been better for him. He decides to go out just to...

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What A Cheerleader Wants

The final bell rang as teacher Marcus Jackson was putting tests into his briefcase to grade over the weekend. It was Friday, so all of his students fled out of the classroom like it was on fire. He got a few goodbyes and some well-wishes for the weekend from some of his more studious students, however, most simply ran off like some girl had lost her top outside.After the last of his students left, another teacher, Philip Caan, walked into his room.“Hey, Marcus! You wanna get wasted tonight? I...

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