The Merry Maid Of Windsor free porn video

The Merry Maid of Windsor By Cassandra Morgan Men swear. Men shout. Men make threats. And so it was that Mark Windsor, my father, was pissed. He stormed around his office, and he slammed his fist down on his desk, and he swept a large stack of papers off of his desk with his arm. He'd had it! The veins on the side of his neck stood out. His face was red and twisted. If a doctor had taken his blood pressure, he would have ducked for cover to avoid the coming explosion. Women are calmer. Women scheme. Women consider. Suzanne Windsor, my mother dearest, was calmer. She sat in a leather chair in the office, watching her husband blow a gasket. She said nothing. She sat there, her arms folded tightly, and tried to think. Oh, she was angry, too. But unless you looked to the rage in her eyes, there was nothing on her face to give her fury away. This was quiet danger. And for all of her husband's temper, hers was the displeasure to avoid. Me? I screw up. I make mistakes. I even trip over my own shoelaces. I am Billy Windsor. And once again, I had messed up. I had gotten busted leaving a party with a pocket full of angel dust, and because of it, Hughes College had pulled my scholarship. Even worse, they had suspended my acceptance for a year, which meant I couldn't even go if Dad paid. I'll admit this. When I mess up, I mess up big time. So I sat in Dad's office and withstood his wrath. I was a waste. I was a bum. I was a slacker. Yeah, yeah. I get it. I fought the urge to look at my watch. I wondered what my future was. Community college for a year? Online courses? Work? "I mean it, he's going to get his ass a job. A real fucking job. None of this grounds-keeper ride-the-lawnmower- and-smoke-weed-all-day jobs. I want the hardest fucking job we can get him, back-breaking, ball-busting work. Roofing houses. Carrying sheetrock. Breaking rocks. Whatever. I'm so tired of him being a fuck-up I can't see." "And how are we going to get him this job," my mother said quietly. "How? I ... I don't know. I know people." "You know, no one supervises a lot of those jobs you mention. The sheetrock, for instance. Do you think the field supervisor is going to watch him carry shit. Of course not. The problem isn't working hard when everyone's watching. The problem is working hard when no one is watching." My father listened. He glared at me. "So what do you suggest, Suzanne?" "You own the Windsor hotels. Get your best people in here. All of them. See whose people work the hardest. The desk clerks. The technical repair people. Security. The cleaning crew. The cooks. Yes, the grounds- keepers. And then put Billy to work there. Make sure he's heavily supervised." "Dad?" I interrupted. "I'm sorry. I'll do better. I've learned my lesson. I know I screwed up, but trust me. I know better now." "Billy," my mother said sweetly. "Please shut the fuck up." She was one of those women with quiet force. She could be a sweet lady, but she could be the biggest bitch in nine counties if you crossed her. I was a lot more afraid of her than my dad, who was all noise and threats. She was action and discipline. And so the heads of the departments of the chain came into the office. And yes, everyone thought their department worked hard. But when my mom peppered them with questions about down time during working hours, well, she found some lapses. The front-desk clerks, for instance, has loads of down time. So did technology repair. Security was a lot of walking around. Telephone operates didn't work hard. The grounds-crew was never really considered. The winner? The cleaning crew. The maids. That was where I was was sentenced to 12 months at hard labor. * * * It didn't sound that bad, to be honest. I would help make a few beds. Run a vacuum over a floor. Change out the towels. Grunge work. It didn't sound like fun, exactly, but it didn't sound difficult, either. It wasn't a great deal different than working at the McDonald's drive- through window. I could do a year of this standing on my head. "Mom," I said. "I know I've been a disappointment to you. But I'll do this. I can be a male maid, and I'll make you proud." "Billy, that's nice of you to say," she said. "I'm glad to hear you're going to try. But who said you were going to be a male maid?" "Excuse me?" "Billy, you adjust to the job. It doesn't adjust to you. You'll be one of the maids on the floor. Otherwise, you would draw attention to yourself, and we can't have that. You aren't a valet. You're a maid. No different. Every maid we have at the Windsor is female. Every one of them wear the same uniform. I expect you to wear it too." My stomach flipped. What was she saying? Me? Female? Uniform? "Mom, I'm not going do this..." "Aren't you, sweetheart? If that's your decision, and your father and I have talked about this, we're going to let you live on your own. You can get a job, pay your own car payments, pay your own rent. Next year? You'll go to college where you can afford it." "But we're rich..." "No, sweetheart. Your father is rich. You have, how do they say it on the street, diddly. Get with the program, Billy, or get out of the way." I seethed. I argued with my Dad, and I was disappointed when he took my mother's side. I offered compromises. I would work in another department for half-scale. I would work in a job outside the hotels and donate my money to a drug rehab facility. Anything to get out of this silly dress- up shit. "Those are some kind offers, Billy," my mother said. "I'm impressed. And I'll tell you what. You do this for eight months and we'll discuss the last four. But you screwed up. So for now, you're on the cleaning crew." "In...in a uniform." "In a dress. You are a female maid. We'll call you, oh, Bailey. Good thing you've got that rock-and-roll haircut. It'll style nicely." "This ... this is just mean, mom. I can't believe you would do this to me. I'll be a laughing stock." "And what about what you've done to us, Billy... I mean, Bailey? Your dad's nerves are shot. His blood-pressure is awful. You are taking years off his life, and I resent it. So you will do this, and you will do this my way. Otherwise, you can live on the fucking street. I've fed up. You do not know how pissed off I am." "Eight months?" "Yep. It takes more time to have a baby." My mouth was dry. My face felt hot. I had lost. I had nowhere else to go, no other way to work, no other direction to go to get to college. I nodded. "Okay," I said. "Okay what?" "I'll...I'll be a maid. If you insist on it." "I insist on it." She had a glint in her eyes. It was almost like she was enjoying this. Was there something about seeing me humiliated that appealed to my mother? Did she really want to see her baby boy in a dress? I looked at the floor. Shit. A fucking girl. Wait til Rock and Lucius hear about this. They'll laugh their ass off. "You can report to Mrs. Hollingsworth for your uniform on Sunday afternoon," my mother said. "Be there at 6:45 a.m. Monday. We start cleaning the floors at 7. We do laundry after the rooms are clean. Mrs. Hollingsworth will assign you your room, and she'll give you your schedule. Good luck, Bailey. I'm sure you'll make a sweet girl." "My room?" "Yes, Bailey. You and another girl will share a room on the first floor. You don't have to sleep there, a lot of the married girls don't. But it's there for you. This is a sweet job, if you work hard. But you have to work hard." I stood and turned. "I hate this," I said to my mother. "And I hate you." She smiled sweetly. "Bailey, you know, you really should get a jump on this. Why don't you start wearing a skirt tonight. A dress if you prefer. Heels. Makeup. The whole nine yards. It's time you presented as a girl." My jaw dropped. She was taking my last weekend from me? "Nooooo," I moaned. Her smile never left her face. Her voice never rose. Bitch. "This is your fault," she said. "Now, you're going to need some clothes. Some panties. Some bras. Some panty hose. Some shoes. Nothing sexy, like a sexy maid at a Halloween party. Functional. You'll need makeup. You might want to get a couple of plain dresses to wear when you're off- duty. So you don't blow your cover. If anyone finds out you're a guy, it will be because you tell them. Not me. You." I turned to leave. I was dying inside. Everyone was going to think this was my idea. That I was a fairy. "Bailey," my called after me as I left her office. "Be pretty." * * * I stumbled around the mall, looking, wondering. How do I shop? I looked at the pantyhose. They were sized by letters. What the fuck was that? Women's shoes were in different sizes than guys? How big was a size six dress? Was I bigger than that? Shit. Who could I ask to help me shop? Skyler? No, she's pissed at me. Becky? I hadn't called Becky in months. Faith? Maybe Faith. Faith was a good girl. In the end, I called Faith. She wasn't home. Becky hung up on me. So I ended up with Skyler. "Skyler? It's Billy...Yes, Billy...I'm sorry...I've thought about you a lot, but no, I haven't called...Well, I'm glad for you and Buzz...That's sweet...On my mind? Well, Skyler. I'm in a jam...I need some help shopping ... For girls' stuff....For me...Yes...Dresses, panties, bras...Don't laugh...I know, I know." In the end, Skyler came, because she thought it was too funny not to come. She had to get a load out of me trying on a dress. I was standing there waiting for her to arrive. I was looking at a black dress. I would love to date a girl wearing that, I thought. But was it too sexy for work? Too practical for dinner? How about the fit? The neckline? Was the fabric a good one? Should I ask to try in on? "Excuse me...sir?" I half-turned, and a salesgirl named Candy was standing there. "Are you looking for something...uh, for your wife?" "Um. Yeah. Yeah, I am. Can you help me?" "Well, do you have her sizes?" I frowned. "Uh...no, I don't. But she's kind of my size." The salesclerk smiled. She knew. She thought I was another cross-dresser shopping for himself. I was trying to stammer out an explanation when Skyler walked up and grinned. "Hi. I'm his wife," she lied. "You probably have figured out by now that this isn't for me. They're for him. My fellow here is a sissy. He loves wearing this stuff. You shout see him prance around the little faggot. But he usually wears my clothes, and I thought it was time he got his own. Right?" "Oh, right," the saleswoman said. "We're pro-transgender here at Carter's. We can help. We even have a third-sex changing room if your ... wife...requires it." "Oh, she does." "I'm Candy. Why don't you two go to the dressing room, and I'll bring some stuff for ... her. Tell me what you're looking for, sweetie." Candy said sweetie like I was the fruitiest loop in the cereal bowl. This was humiliating. I ran down the list. Nair. Panties. Bras. Pantyhose. Shoes. Dresses. Some light jewelry. She put me in the dressing room, and she started bringing me things. The panties were easy. First guess. The bra worked out fairly quickly when I decided that a B-cup was fine as far as inserts went. Pantyhose were good. The shoes worked out -- Skyler bought a pair for herself, which I paid for. The dresses were a little tougher, but she found me a dark blue one, a white one, and a gray skirt and burgundy blouse. "Billy? Are you aroused? Skyler asked me. "God no. I'm being forced." "Uh-huh. I notice you didn't ask to stay with your friends?" she said accusingly. "Skyler. I need that scholarship." "I'm sure that's it. Oh, look. Candy brought us more dresses!" Candy offered Skyler to call her friend Sheila at the hair salon and made an private appointment for me for Sunday afternoon. Sheila would take care of my hair. She would also pierce my ears and select my makeup. Don't thank me, Candy said. I left with my arms filled with packages and my head filled with doubt. This was getting deeper and deeper. I was confused. I had all this ... shit to learn how to put on. When I got back home, I went to the bathroom in my room. I looked in the mirror. Was there a girl in the image? Could I really be transformed? What if I liked it? Some guys did, you know. There were boys who changed into girls every day. Was being a girl really so much better? And did I have any choice? * * * I was in a beige skirt with a white blouse. It seemed less overpowering than a dress. But I had on panties. I was wearing a bra. I felt like I was auditioning for a part in the Rocky Horror Picture Show. I moved around my room, trying to adjust to the different fit of the clothes. It was tight in places boy clothes aren't. It was loose in others. The panties were soft. The bra, with its seams in the cups, seemed obtrusive. The wig didn't feel right. I shifted it. And again. Then I pulled it off and decided to go with my own longish hair. "Well, aren't you pretty?" the voice said. I turned, and it was Skyler again, who had entered without knocking. Only this time, she was with Buzz. Who was laughing his ass off. "See, Buzz, I told you. She's a tranny. Oh, wait. Is that an allowable word? She's a transvestite. She told me she always has been. She gays it up with her lipstick and dresses, and then she goes and picks up sailors. Blows them for quarters. But it adds up, doesn't it, Bailey." "Bailey?" Buzz said. "You're queer, Bailey? Hell, I knew you were a pecker checker in the men's room. Always looking at my dick." I could barely make out their words. There was a loud humming in my ears. I felt humiliated.Two of my friends were staring at me in girls' clothing. Hell, in MY girls' clothing. There was no joking my way out this, no lying about a party, no fibbing about a school play. Skyler had told Buzz I was a homosexual. Given I was a guy in a dress standing in front of them, who wouldn't believe that? "Skyler, please tell the truth," I said. "My mom is making me do this." "Your mommy is making you? Ooooh. What? Did she threaten to take away your Easy-Bake Oven if you didn't dress. Or your dolly?" She walked toward me. "You're a fag, Bailey," she said. "Just fucking admit it. You blew Bobby Hainesworth, I heard. In the boys' locker room. After P.E. All the guys saw it." "Yeah," Buzz said. "I saw it myself. I just didn't know it was you in that dress. God, I hate queers." Skyler stepped close and whispered. "You fucked me over, Billy," she said, reverting to my boy's name. "We had sex and you never called me. I thought I was pregnant for weeks, and you were off smoking dope with the boys. Well, now you'll be sucking cock with the boys." She spun and walked toward the door. "Oh, Bailey," she said. "When he cums, be sure to breathe through your nose. We wouldn't want you to gag." She laughed. She left. Buzz walked out some time afterward. He turned. He spread his thumb and pinkie. "Call me," he whispered. * * * Sunday. Dress rehearsal. I dressed in a new blue dress, a plain one, just to check into Mrs. Hollingsworth office. I dabbed a little lipstick on my lips. I worked on my eyes for an eternity. How did women get that shit right? I looked at myself in my mirror. I hated what I saw. I looked like I should be on the cover of Vanity Fair. I shook my head at the realization that my mother was making me do this for eight months. What was that? Two hundred and forty days? Something like that? I drove to the hotel. Not in in Jag, but it my mother's yellow VW. The maid mobile, she now called it. A maid! The knowledge of it poured over me yet again. Finding Mrs. Hollingsworth's office, I stepped inside and sat. There were other girls there, all waiting for the same purpose I was there for. We filled out our employee contracts - I had to remember to write "Bailey" - and we were issued three gray uniforms and a black one. We were told the black was for more elegant occasions in the hotel - banquets and weddings. We were supposed to report to the staff room at 6:30 each morning. We were supposed to be presentable. We were supposed to be cheery to the guests. We were warned to always keep the room door open, just in case. Mrs. Hollingsworth walked up to me. She looked at her clipboard. "Now, Bailey, let's look at you. The length of your skirt is good. You aren't showing too much cleavage. But your eye makeup is too heavy. You aren't going to a bar here, dearie. And the lipstick is a little too red." She spun. "You're here to work, girls. We don't marry millionaires like in the movies. We don't end up owning the hotel. We make beds. We scrub toilets. We vacuum floors. You should know the rules. If a towel is on the floor, you get the guest a new one. If a towel is hung up, he wants to keep it. We change linens every two days unless we have a request for daily changes or unless there is a new guest. Each morning, you will get a list of which guests are checking out. "Check out time is noon unless a guest requests a later check-out time through the front desk. Each guest has a door-knob hanger to say if he wants service or wants you to wait. You are to keep out of the public areas as much as possible. I don't want you traipsing through the lobby. You are the help. You are not a guest. "We work hard here, ladies. I recently met with Mr. Windsor about an issue, and I was informed we are the hardest working unit at his hotels. It will stay that way. Drugs are an automatic dismissal. Sex with a guest is an automatic dismissal. Theft is an automatic dismissal. "Every afternoon, two of you will be on laundry duty. That means each of you wash and fold twice a week. Between the towels and the linens, that's hard work. I still expect you to be in uniform. "We are family.We discourage cattiness among our girls. We accept everyone. If someone is foreign, that will not be a problem. If someone is black, that will not be a problem. If someone is a lesbian, that will not be a problem. Clear?" No one said anything. We were the fucking help. This wasn't a discussion group. We walked toward our assigned rooms. Everyone had a roommate. We were in double rooms. A small closet, a bureau, a small TV in the corner. There was a small refrigerator in the corner. My roommate introduced herself as Cathy. She was a short girl, a little chunky. "Hey, you wanna grab a beer?" she said. "We have the day free. The job doesn't start until tomorrow." I was hanging my maid's dresses in the closet. "I...I think I'll pass," I said, not wanting to go anywhere in a dress. "I have some organizing to do." Cathy nodded. She watched me work. "You're... a guy?" she said. What? How did she know? Did I not pass? "I'm sorry?" "It's okay, Bailey," she said. "They warned me that I was going to be rooming with a cross-dresser. It's okay. I'm a sissy myself. They couldn't legally room a genetic guy and a genetic girl together, you know?" "You're....what?" "I'm a sissy," she giggled. "A submissive. When I'm lucky, I have a Mistress to tell me what to do. That's my thing. The control. I hear you're one of those boys who likes girls' clothes." "Um...yeah. Girls' clothes are pretty, don't you think?" I saw no sense in telling her I had been forced into them, and into this life. Let her think I was a cross-dresser. "Bailey, we're going to be roomies for as long as we work here. Let's be besties, okay. I'm a nice person. I'm sure you're a nice person. You're certainly pretty enough." I smiled. She seemed sweet...for one of those. I wasn't quite sure what a sissy was, but she seemed harmless enough. "Bailey...I can fix your makeup?" I looked at her. Nodded. "That would be sweet, Cathy." "My friends call me Cream-Pie," she said. "But I had to have a legit name for this job." "Cream-Pie?" "Long story," she said. "Well, Cream-Pie. Why are you working here?" Her eyes widened. "Bailey, this is a perfect job for a sissy. We love to clean. We love maid's uniforms. I get to make beds and do laundry. Do you know that a lot of older sissies end up working at hotels for a living? It's what we're good at. It's where we belong." "Cream-Pie, I'm not a sissy." "But are you willing to learn?" she laughed. She was finished with my eyes now. The difference was startling. I looked like a girl next door type, not a girl who lives next door to a brothel. After all, if I was going to be a girl for eight months, I might as well look the part. I plumped up my my breasts. I looked at my butt. Would I date me? I didn't know. Cream-Pie smiled. "You look perfect, princess. Your hair is just long enough to curl. It'll be better when it grows out just a bit. You'll be the prettiest girl here." The prettiest? Me? That wasn't what I wanted. Was it? * * * The sun arrived early. I assumed it always did for cleaners. When I was a slacker, I would sleep until noon. I would get up and light a joint, just to feel something. I would ease into the day. I would find my buds, Scott and Terry and Ruthie and Buzz, and we would hang out, watching movies, trying to get to dark. And then we would party. Now I'm up, replacing shampoo, vacuuming, trying to make a fitted sheet cover the mattress. I am slow. Other maid's whiz through, an economy of activity making their appearance. They don't exchange small talk. They have a rhythm to their work. They could blow through a disheveled room in 10 minutes. I took almost 20. That first day, Cream-Pie - Cathy at work - took up the slack for me. She was so fast, so efficient. "Did you see?" she whispered to me once as we left a room. "See?" "There were panties in the bed," she said. "So?" "So two guys are staying here. And there is only one bed." She circled her index finger and thumb. She took her other index finger and ran it in and out, pantomiming sex. She laughed. I craned my head back around to look. "Baby, it isn't important. We're all about sex. Different people like different sex. I'm not judging. I ... just notice things. Hell, if you would have come into our room a half-hour earlier yesterday, you would have noticed me." "You?" My eyes widened. "I met a lady at the bar," she said, giggling. "It was just sex. Just mindless sex. My tongue is worn out." "You had sex in our room?" "Hey, you can, too. Leave pantyhose on the doorknob. Take a guy back to the room - hell, two guys -- and I'll just hang out in Amelia's room." "Um, that won't happen." "Why the hell not?" "I'm...I'm here to work," I said. "Hell, a girl has to play, too," she said. "Especially if a guy has something to play with." * * * The mornings came early to me. They were a pain, a drudgery. I hated picking up towels that had been on the asses of strangers, changing sheets that were soaked in their fluids, throwing away their half-eaten pizzas left on the nightstands. Cream-Pie had a better attitude. She hummed through her chores. She made beds like an artist. She took pride in arranging the soap dish, in placing the new towels. She really seemed to like this cleaning stuff. It was easier for her, I thought. She was a sissy. "Bailey, sweetheart," she said in mid-morning. "Can I tell you something?" "Sure, Cream-Pie," I said. "What is it." "I think you're the bomb, Bailey. I really do. But your attitude kind of sucks, to tell you the truth." "Excuse me? I do my work." "But do you take pride it? Do you wash a spot from the window and get happy because it's gone? Do you smile when the tub glistens? Do you get hard when you look at a made room? Look at the way you sit with your knees a foot apart. You're a fucking lady! You could fix your hair nicer." "No, not really. But most maids don't." "But we're not most maids. We're sissies." "You're a sissy." "Well, you know what I mean. There is a reason we're here. They pay us money to clean. We should do a good job." I looked at her. She was completely sincere. She was so innocent, so pure. I nodded. "I'll do better, Cream-Pie. I'll make you proud." She nodded. "Get into it, sure. You really do get an erection when you're into it." So I scrubbed harder. I folded neater. I paid more attention to detail. I dedicated myself to learning to love to be a maid. No, all maids don't love their work. But because of Cream-Pie, I learned to love it. Sure enough, I was picking up towels one day, and I noticed it. I was erect. Should I tell Cream-Pie? Or would she want to take a close look at it? * * * His name was Phil Grant. And he was a guest. He was in town from Denver, here for a weeklong pharmaceutical convention. He liked to work in his room, pounding his laptop. I would knock and ask to clean his room, and he would not look up. He would merely waggle his hand for me to proceed. So I would work around him, making the bed, replacing the towels, arranging the soaps. I would ask him if I should vacuum, and he would decline. I would empty the waste baskets and do a general pickup. I don't know when he first noticed me. But suddenly, I wasn't just in the background. "Hi," he said. "I'm Phil." "Hello, sir," I said. "I'm Bailey. I'm your maid." "And a pretty one. Like in the movies." I nodded my thanks and lowered my eyes. I kept working. "You from around here, Bailey?" "Yes, sir. I grew up in Cincinnati, sir." "Well, go Bengals." "Yes, sir," I said. "Do you need extra towels?" "Maybe a couple. Bailey, what do you do for fun around here?" "Not much, sir. I keep pretty busy." "Could you...show a guy a good time?" "Sir, we're not allowed to date the guests." "Oh, no one will have to know, Bailey. We'll go to dinner, maybe dancing. Wouldn't that be f un?" I actually thought about it for a minute. I certainly didn't fear getting fired. Being out on the street would be easier than living in a dress. But...what was I thinking? This was a guy! Had I started to judge the attractiveness of men? "I'm afraid I can't, sir," I said. I went to step around him, and his hands were on my shoulders. He leaned down and kissed me, his tongue probing my mouth, his hands on my bottom. I pulled away and shook my head. "No," I said. The next day, Cream-Pie cleaned his room. I always wondered if she cleaned his dick, too. * * * It was Thursday night. A workday for the world. A night off for me. Cream-Pie had insisted we go to dinner, to Del Monte's, an Italian place. Afterward, she wanted to get a drink. Or seven. She really was pretty, standing there in a blue dress, her hair falling around her shoulders. Her lipstick was darker than she wore at work. Her mascara was bolder. She was showing some cleavage which, by the way, looked like it was all her. I wore a red dress. My hair still wasn't as long as it could be, but she wouldn't hear of me wearing a wig. She twisted and fussed, and it came across as a fair butch-looking hairdo that looked pretty good. These were the times I couldn't understand my mother. What would it hurt if I dressed like a guy? Just for the evening, even. Just so men's eyes wouldn't roam across me. Cream-Pie helped with my eye makeup, but I was getting a little better at it. "Bailey, I am so proud of you. You've become the best sissy on the floor. You're such a joy to work with." "Cream-Pie, I'm not a sissy," I said. "Right," she said. "Keep telling yourself that." She frowned. "Bailey, what are we going to do with your boobs?" "What's wrong with them?" "They're pancakes!' She said. "A good sissy needs her titties. It's our source of pride. It says we aren't just playing dress-up. We're committed to this. I have a good boob doctor. He can put a couple of implants in. You'll have boobs in two weeks. Pretty, firm boobs." "No thank you, Cream-Pie," I said. "I'll deal with what I've got." "Okay, okay," she said. She grabbed her purse. She handed mine to me. "Food! Wine! Men!" "Excuse me?"' I stopped in the doorway. "Oops," she said. "I wasn't supposed to tell you. There are these two guys..." "You didn't! Cream-Pie, dammit. I'm not gay." "Who said anything about gay? It's just dinner company. They're funny guys. Sexy. Smart. You don't have to get laid, bad as you need to." "Cream-Pie!" She laughed. She took my hand in hers, and we skipped down the hallway. We left by the servant's entrance and got into her gray Ford. The restaurant was nice. Small, but clean. Music playing. Dim lightning. We were shown to a table and handed menus. The table had red-and-white checkerboards. Then they were there. Jeff and Lane. Jeff was tall and dark. Lane was shorter and had dimples. Cream-Pie reached up and kissed Lane like she was trying to steal his chewing gum. Jeff reached down and took my hand. "Bailey?" "Hi," I said bashfully. "I'm Jeff. Cream-Pie says you haven't dated much. I'll be good, okay? Let's just talk, and we'll have some wine, and you'll see I'm a nice guy. Okay?" "Hi, Jeff. That's good news, really. I don't know what I'm doing here." Have you ever been part of the couple that was G-rated in an R-rated foursome. Cream-Pie and Lane were all over each other, grabbing and groping, teenagers in lust. Jeff kept a safe distance, talking and joking. He was so good that I forgot I had been fixed up for a date. We just had a nice time. Near the end of the evening, Lane excused himself. A minute later, Cream-Pie did the same. She winked at me as she left the table. "Dessert?" Jeff said. "What do they have?" I said. "Evidently, they have sex on a stick," he said, looking in the direction the other two had gone. Then fate struck. I was still walking underneath that black cloud. A couple bounced past, and then stopped. It was Buzz and Skyler. She squealed as she saw me, her hands flying to her face. "Bailey!" she said. "And you're on a date! That's so sweet!" "Who is Bailey?" Buzz said. "It's Billy, you moron," Skyler said. "Oooh. Billy. Damn, son. You've got nice titties." "Buzz, Billy is on a date with a guy. She probably has to excuse herself so she can give him a hand-job. Or do you just suck and run?" I burned. My face turned a thousand shades of red. I stared at the table, saying nothing. "Now will you admit that you want to be a fucking girl?" Skyler said. "You're our Caitlyn Jenner. You're our Laverne Cox! Be proud, girly. You're one of us now." "Hi, I'm Jeff," Jeff said. "And you are..." "I'm Skyler. I'm an ... old friend of your tranny girlfriend. You did know she had a dick, right?" Jeff smiled. "I knew," he said. I looked at him. I didn't know that he knew. I suppose Cream-Pie had told both of them. "Oh," Skyler said. "So you two are suck buddies?" Jeff shook his head. "You're a very crude young woman, Skyler. And very rude. What Bailey and I are to each other is none of your business. For the record, I find her much, much more charming than I find you." Skyler sneered. Did she really hate me so Had I been that horrible to her? Yes, I probably had. I probably deserved her scorn. "Skyler," I whispered. "I'm sorry. For all of it." Her face softened for just a moment. And she was Skyler again, my old friend. Then she hardened again. "It's okay, Bailey," she said. "Just be careful not to drag your teeth when you suck his cock. It's really hard on a guy. Right, Jeff?" She walked toward the door. She stopped. "Are you coming, meathead?" Buzz hurried to catch up. * * * The next day, I was summoned to Mrs. Hollingsworth's office. "Sit down, Bailey." I sat. "How is your father? Does he accept you being a girl?" "I guess. It was my parents' idea, Mrs. Hollingsworth." "Marie..." "Yes ma'am." "We get a lot of sissies here, Bailey. The job attracts them." "I imagine." "Do you have a Mistress, Bailey?" "No, ma'am," I was about to tell her I wasn't like Cream-Pie. "Would you like me to be your Mistress, Bailey? I'd be good to you. I'd take you home. You could dress and cook and clean." "Ma'am, I'm not..." "You can lick me Bailey. Lick me now, and I'll buttfuck you." "Ma'am, I'm a man." She laughed out loud. "You're not a man. Have you seen yourself? You may be the most feminine maid we have. The way you move. The way your voice sounds. Bailey, face it. You're a girl. A sissy." "I'm not," I whispered. "You are. And when you realize it, my strap-on will be waiting. I don't usually fuck the help. But you, I'd fuck?" I left. I went to my room, a tear rolling down my cheek like I was a pussy. I stared into the mirror. An innocent girl stared back. Was this me now? Was this my future? And as long as I was asking questions, this one came to mind: Was I pretty? * * * I sat in my father's office in a maid's dress. I hoped it would make him soften my punishment. It did not. He sneered at my outfit at the disappointment I had become. "Bailey, you're doing better," my father said. "Your work ethic has really improved. Mrs. Hollingsworth raves about you." "Thank you," I said. "Can I start wearing guy clothes again?" "Oh, dear," my mother said. "You're doing so well. I would have thought you would have accepted things by now. You obviously like the life of a maid. Some boys were meant to be girls." "It's not that I like it, mother. I'm trying to impress you." "Well, you're certainly doing that. And your hair and makeup are flawless. You really must like being a girl." "No, mom, I just ... " "I heard you went a date with a man. Is that right?" "It was a fix-up," I said. "Not really a date. Nothing happened." "It's certainly not your parents' business," my mother said, smiling at my father. "See, hon, I told you that Billy...Bailey would be better off as a girl. I mean, dating a man is a huge step. That wasn't something you had to do. Sex is acceptance." "We did not have sex." "Well, you certainly wouldn't tell you mother, would you? You'll love being a girl. Girls are calmer. Smarter. More in control of their tempers." "Yeah, but I'm not crazy about my son being gay..." "Ah, pshaw," my mother said. "Everyone is gay these days. Would you rather have an irresponsible thug on his way to jail or a gay son who is happy? Or a daughter? Bailey could have surgery, you know." "Mom!" She laughed. "I'm serious. Have you thought about breasts? I understand Caitlyn Jenner has breasts. A lot of transvestites wind up with them." "Mom, I'm not a transvestite," I said. "And yet, you sit there in a dress," my father said. "And you have a boyfriend." "Dad, I'm in a dress because mom made me. And he isn't my boyfriend. He's just a guy I know." "I'm not crazy about you having sex with a guy who isn't your boyfriend," my father said. "Does he wear a condom? Suzanne, tell him to make sure this guy wears a condom." "Make sure he wears a condom, Bailey," she said. "We wouldn't want your father to get upset." "Mom, this is out of control," I said. "Yes dear. I'm sure it was hard to be in control when you were a boy, and now, you're a girl. Have you considered a vagina?" "Oh, for God's sake. I do not want a vagina. Understand me. I do not want one." "I understand, dear. Just the breasts, then." "Mom! No!" And so it went. Every word I spoke was twisted. I told her I didn't like the clothing I wore, and she ended up ordering me three new dresses. I told her I didn't like wearing bras, and she thought it was because I wanted bigger boobs. I told her I had trouble walking on heels, and she ordered me a new pair. I know there are women who get off on seeing men in dresses. Was my mother one of those? She seemed to get so much pleasure from my femininity. She was convinced I was doing better because she had put me in a dress. She thought I was calmer because I made beds every morning. She thought I was happier because I was dating a man. Every conclusion that was there she jumped to. "Bailey, you know you don't have to leave after eight months. We could extend our contract. You could be a maid for as long as you want, hon. You never have to go back to being a man." She smiled, like she had presented me with a gift. I wanted to cry, but then, my father would really think I was girl. * * * In December, the snows hit. We don't get that much in most years, but this was Alaska come to visit. Which was fine, but the power failed, and the hotel was dark and cold. I woke up about three o'clock to the feeling of someone's butt pushed against me. Cream-Pie. She had left her bed in the night and crawled into mine to share body heat. And we late there spooning, her ass pushing against me. "I love where your hand is," she said. Huh. I looked down, and my hand was gripping her penis. It was hard in my hand, small, but erect. I let go of it like it was a hot frying pan. "Awww," she said, wriggling her butt into my crotch. "That was nice." She took my left hand and place it on her left breast. It was soft, and warm, and substantial. I pulled that away, too, like it was an electrical socket. "Cream-Pie, stop it!" "Oh, I know you don't like girls. You'd rather have Jeff. But sissies can play sometimes. You can fuck me first, and then I'll fuck you. Or the other way around. We can pretend we have a Mistress and she's making us." "Cream-Pie, I think you're great. I really love you. But I keep telling you, I'm not a sissy." "You ... you love me?" "Well, sisterly love," I said. "We're close. I trust you. I like you." "You love me!" She threw her arms around my neck and kissed me quickly on the mouth. "I love you, too, Bailey," she said. :Would you like a blow job?" "Um, that's okay, Cream-Pie." "Please?" I looked into her eyes, and I realized the oral sex she was offering was for her more than me. She needed something to mark an occasion when we had pledged our affection for each other. Damn it. I sighed. I nodded. She smiled, and scooted down on the bed. And then a warm wetness was on top of me. It had been months since I'd had sex, and she felt wonderful. Her mouth was a miracle, here and there, sucking and kissing. Her tongue was a living organism, pushing and prodding. She was so pretty, so soft, so giving. But she was a guy. I was having sex with a guy. I was living as a girl, and I was having sex with a guy. What did that make me? What it make us? And then I came, and I no longer cared. * * * It was a week later that I stepped out of the shower. I wrapped a towel around me, and then I noticed that I had wrapped it around my chest, too, like a girl. I looked in the mirror. My hair had grown. I looked girly enough. I traced my nipples with my fingernails. I wondered what real breasts would feel like. And suddenly I wanted them more than I wanted oxygen. I wanted to feel their weight, their outline against my dress. I put on my panties and a bra, and of course my breast forms. I looked again. I posed, sticking my butt out and making kissy faces. I laughed. And it hit me that I liked the way I looked. I liked being Bailey. I took my thumb. I stuck in my mouth, like I was giving a blow job. It felt small. When does a guy become a girl? When does a teenager graduate from a boy playing in his sister's dresses to a transvestite? When are panties a fetish, and when do they become the norm. It had happened to me. I was no longer a boy in a dress because his mother had insisted on it. I was a sissy. I said the word again, slowly. Siiiissssyyyyy. I loved it. I walked over the telephone. I called my mother. I told her secretary that her daughter was on the line and would like to talk to her. A moment later, she picked up. "Daughter?" "Hello, mother," I said. "Daughter?" "Yes, mother. I'm not going back. I'm forever Bailey." She squealed. "Well, welcome to the world, Bailey. How big are your tits going to be?" I laughed. "I haven't thought about it," I lied. "Big enough to cast a shadow." "I am going to be so glad to have a daughter." "You have been since the first, haven't you?" "Could you tell? I always wanted a daughter. You know, I've read that some mothers raise their sons as girls. I always wondered about that with you." "Well, it worked out. It took me some time to get used to this. But I'm there." "Sweetie, did you know Mrs. Hollingsworth is leaving? I think it would be a fine job for you." "Let me think about it, mom. But to tell the truth, I like being a maid. I'm good at it." "I have a daughter!" she repeated. "You do, mom. Are you going to tell Dad?" "Eventually," she said. "But right now, you're mine, okay? I love you." "I love you, too, mom." I said. * * * Cafe Ormond is a small place with most of its tables outside. But it was still cold, so we waited for a table. I had two hours off before I had to get back to run the washing machines. That would probably be 1:59.55 too long. And she sat down. Skyler. "Hello, Skyler," I said softly. "You look nice today." She flipped her hair. Grinned. "Not as nice as you, buttercup. You look nice, too. You are really becoming a beautiful woman. You should never go back. You know you don't want to." "I don't know what I want." She made small talk. She had finally dumped Buzz, although he might not know it yet. She was active in local politics, and voting for Walcot. She might buy a new car. It felt good. It felt easy. All of her meanness had subsided. I'm sure she still resented parts of me, but I wasn't that guy anymore. Obviously. "How is your boyfriend?" she asked. "Jeff was never my boyfriend, Skyler. We never did a thing. He wanted to, but I was scared. I guess that's the main thing you could say about me. I've been scared my whole life." She looked at me. Nodded. "Do you think you were a girl all along?" "Hell, I don't know, Skyler. There are still times I want to put on jeans and scratch my nuts, you know. Like any normal guy. But my roommate, Cream-Pie, has helped me feel better about dressing as a woman." "Wait. Cream-Pie?" "Well, her real name is Cathy, but everyone calls her Cream-Pie." "You know what that is, right? It's cumming inside someone." I laughed. "I figured it had a sexual connotation." "God, you're naive." "Me? How about you." She laughed. She reached out and put her hand on mine. I looked at her. "Bailey? Should we try again?" "With me like this? In dresses? In lipstick?" She shrugged. "I think you're kind of hot. And I believe in the old lie that it's just cotton. We have too many hang ups on whether you have pants legs or not." "I have to tell you something. The other night, Cream-Pie and I..." She nodded. "I figured," she said. "It's okay." "Skyler....I don't know how it would work." "I don't either. Not totally. But you're submissive. So I would be in control. Okay? I would run our house. If I want you in handcuffs, you will be. If I want you to get a tattoo, you will. What do you think?" My mouth was dry. There had been so many women in charge of my life lately. My mother. Mrs. Hollingsworth. In a way, even Cream-Pie. Now Skyler was offering to do the same. "Do I stay in dresses?" I said. "You know you do," she said. "Forever." I nodded. "Lipstick? Jewelry? Boobs?" She just looked at me. "We will make you into the sissy you long to be," she said. "And I will become the Mistress that is inside of me. All those days of being a bitch? Did it make you hard?" I giggled. The word "sissy" jolted me, however. Cream-Pie had used it to describe me. But a sissy was something different than a transvestite. Yet, I thought, I really had learned to love to clean. I did dress as a maid five days a week. I did do laundry. "Now, my sissy, I'm going to have a salad. How about you?" And, as easy as that, it was decided. I had a Mistress. I was her sissy. There would be no going back at the end of eight months. This was me. In a corner of my soul, this had probably always been me. I was free. There was no more ego in my way, no more boundaries to fight. This was not just an accidental job. Somehow, my mother must have known. She must have seen the girl in me. Do I pass? A million cross-dressers ask themselves that every day. But in my case, it doesn't matter. This is who I am. A sissy. * * * I curtsied when he entered the apartment. That took him aback. I stood in the doorway, wearing a black-and-white maid's dress. My hair was long enough to wear up now. My new breast implants had healed, and I was flashing a bit of cleavage. My lipstick was crimson and inviting. "Come in, Jeff," I said. "Do you live here now," he asked. "Yes. Mistress Skyler and I live here. Two months now." "Well, you have a lovely home." He handed me a bottle of wine he had brought as a house-warming present. "Jeff, I want to apologize. We were together during a time when I was still fighting this. You were kind to me. I'll never forget that." He shrugged. "It was easy to be kind to you. You were a gentle soul on a chaotic sea. I knew you would be fine eventually. I just didn't know it would be with Skyler." I laughed. "That was my fault," I said. "When I was a guy, I was an absolute ass to her." "Bailey, are you happy?" "Yes, Jeff." "Then that's all that matters. You know, I've known a lot of trans women since I was in the Army. And I've had some desires I had to fight, too. It wasn't easy to admit to myself that I liked girls who weren't quite girls. You were the prettiest one of them all." "Thank you, Jeff." "Where is Skyler now?" "Oh, she's on her way home from the office. She's working for Windsor hotels now as an office manager. My mom's doing, really." I served the brie. There were strawberries and chocolate shavings on the side. A nice chilled red wine. We talked about school. No, I wasn't going back. We talked about Mistresses. Yes, I was wearing a cock cage. We talked about submissiveness. Yes, I still saw Cream-Pie several times a week. Mistress allowed us to play. We talked about work. No, I had not taken Mrs. Hollingsworth's job when she left. My mother offered it, but I didn't think a sissy should be in charge. The door opened, and Skyler walked in. "His pants are still on?" she asked me. "What kind of host are you?" And she laughed. Mistress had thought for a long time that I should experience a man, a real man with a real dick. So she'd invited Jeff. She became a Hollywood director, whispering this instruction and that one as we burned off the afternoon. After all the protests, I found out I liked a cock in my mouth. Not so much for taste - it was skin, for goodness' sakes - but for the feel of it, the heft of it, the fit of it. His cock was triple the size of Cream-Pie's, and he came in quarts, not in droplets. I tried deep-throating it, but I preferred tongue-play around the knob. Mistress took out the key to my cage. She undid it, freeing me for the first time in a whole week. And she pulled off her shirt. What good was being in charge if she was going to be a bystander? My journey was a long one. Along the way, I had learned a work ethic, and discipline, and honor. I had learned about myself, about Skyler, about Cream-Pie. I was only a sissy. But, for the first time in my life, I liked me. Jeff grabbed my hips. He turned me over. And evidently, his dick liked me, too! (c) 2015 by Cassandra Morgan