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Playing the Maid As far as old country houses go, this one was entirely too big to be quaint, but too friendly to be imposing. It stood on its own acre of land about three hours north of San Francisco, up near Napa Valley. While this was a long commute for us, my wife Emma and I had already been telecommuting to our respective offices a few days each week, and we made arrangements so we only had to be in San Fran the same two days out of the week. It was only by luck that we'd been able to afford it. The house had come up for a short sale a few months prior and had found a buyer almost immediately. One evening about a week later, Emma spent almost an hour looking at pictures of that old place. We joked about the commute and how impractical it would be, and seeing as it already had a buyer there didn't seem like there was much we could do about it. A few weeks later, Emma suggested we go on a road trip, wine tasting in Napa Valley, and I said it seemed like a good idea. Of course, one of the wineries she wanted to visit was only about 10 miles from the house, so we took a side excursion to see it. The surrounding terrain was beautiful, but rough and unsuited for growing grapes, and driving up the dirt road felt like taking a trip into a state park. It was a large three story house that managed to straddle the line between being overly fancy and come-on-in inviting. There was still a "for sale" sign in the yard, and it didn't look like anyone was home, so we took a brief walk around the estate. The front was mostly rocks and low growing plants that would have been classified as weeds in the suburbs. The back had a large stone patio and a small flower garden next to a large shady oak tree that overlooked a hillside bluff. We heard the engine of a car driving up, and we thought it best to say hello and confess to what we were doing; though, Emma poked me, and said we shouldn't say we knew it had already been sold. The car turned out to belong to a real-estate agent named Betty. She was a middle-aged Asian woman, stocky but not overweight. She explained that the new buyer's home loan had fallen through, and the previous owner was still in a hurry to sell on account that they'd just moved to London for a job and needed the money to secure a small house there. When we explained that we were interested in the house and confessed we weren't sure if we could make it work, she offered to take us out for dinner. A few weeks later and the house was ours. There were a few issues, like broadband service was non-existent, but we have a tech savvy friend back in SF who offered to hook up Internet over radio to the nearest service provider, and that worked well enough. Some of the house was pre-furnished as the previous owners had been antiquers. None of the furniture was very expensive, and most of it had a dent or scratch somewhere, but this afforded the home a sort of old world charm that added to the experience. A few of the upstairs rooms were still empty, and we set up our offices there. Since the new house was much bigger than our old apartment, it felt like we'd transplanted our old place into those few rooms and were just visiting the rest of the place much like a hotel or a museum. I was just getting around to setting up some work out equipment when Emma burst into the room. Her face was lit up like a Christmas tree. "Hey Jules, guess what I found?" she asked me as my name is Julian. "I dunno, a chest filled with gold?" "No," she said smiling and swinging her head side to side. "A body?!" She huffed, "No, be serious." "I don't know, seems like the price on this house was too good to be true. There's bound to be something ominous lurking around here somewhere." "Okay, let me show you." Emma grabbed me by the hand and practically dragged me over to the end of the hallway that ran beside our bedroom. "See anything?" she asked. "Other than the prettiest girl in the whole world?... nope." I tried to get in compliments when I could. Emma blushed and took a flashlight out of her pocket and pointed it at the ceiling. There was a gap with a small metal loop, just barely visible, tucked inside. "Check this out." She took a long wooden rod with a hook at the end of it and seemingly from out of nowhere pulled a folding staircase down out of the ceiling. "You've only seen half the attic." We made our way up the stairs, and Emma flipped on a light switch. This part of the attic was half finished with a solid plank floor, a few chairs, and a large mirror that stood beside a doorway to a second room. She opened this up into what must have been the world's largest walk-in closet. The room smelled of cedar and contained four ten-foot long lines of hangers. From each hanger hung a simple canvas bag that zipped up along a clear plastic side. The bags were filled with outfit after outfit of fancy women's clothing. "Wow, honey it's like we have a whole department store up here," I exclaimed. Her face brightened into a smile. "I know! I wonder why they left all this stuff here. It looks like it must be worth a small fortune." "Maybe she got fat and none of it fits her anymore." Emma's smile dropped into a look of impending disappointment. "Oh, I wonder if any of it will fit me." I shrugged my shoulders. "Try something on and see." Emma took a few quick steps down the first row and turned her head to either side. She pulled down a bag and dragged me back into the room with the mirror. I'd never seen her in such a rush. The bag contained a fancy red dress in a western saloon style. It was the type of dress "working" women wore in old westerns. She rushed with excitement to put it on, and I helped her zip it up the back. Gazing in the mirror to judge herself, she made bobbing motions with her head as she mulled it over. "Well it's not a perfect fit but it's not too bad, maybe just a size or two too large for me. Kind'a feels like trying on my big sister's clothes." "It looks like it fits to me." "Yeah, I guess it fits okay. Would have been nice if it had been perfect, but I guess a little too big is way better than too small." Emma stayed up there for the rest of the day trying on clothes. I'd go up every few hours or so to check on her, and she'd tell me just a few minutes more and ask me to help her put something on. "You know Honey, it's eight o'clock. I think you've officially missed dinner trying on clothes." "Really it's that late already?" Her face made the oops expression. "They'll still be here tomorrow. What is it with you and dress up?" "Well... it's damn good fun. Didn't you ever play dress up when you were a little kid? You know get into your father's clothes." "Only when I had to go to a funeral." "Oh, that's sad. Though, I guess I'm letting it get a little out of hand. It's kind of like you and video games sometimes." "I can see that, just one more level is it?" I asked. I could see her looking up and thinking for a second. "You know what we should try? Just to mix it up a bit..." "No what's that?" She looked me over and said, "You should try something on." I took a step back not saying anything. "God, sorry Honey. I didn't mean it like that. It's just clothing. I thought we might have some silly fun." "Maybe... What did you have in mind?" She slapped my butt. "That's a girl, hold on a sec, let me go find something." "Great.." I thought about running down the stairs while she was off in the closet, but I figured I could bear through this. A few minutes later, she emerged with something long and black. "I found this. It looks Victorian or something. Kind of solemn and formal, so it shouldn't be too embarrassing." "Looks like I could wear it to a funeral." The dress was full length, black with a collar, and had lots of lace. It was straight and didn't look like it would blossom out in too girlie a manner. In an odd way, it reminded me of a priest's robe. "Sure why not? Now strip." She pointed authoritatively down at my pants. There wasn't any procedure. I just pulled off my clothing and stepped into the thing without thinking. Emma tugged at the sleeves pulling them down over my arms, then adjusted the skirt and started zipping up the back. I never had anyone zip me up before, and it was an odd thought that I'd have trouble getting the dress off without her help. She reached back, pulled out my ponytail, and played with my hair for a second before turning me toward the mirror. "Hmm, I look odd," I said pausing. "I'll say one thing, the dress fits you just fine. 'cept in the boobs, you haven't got any. And you're maybe just a bit too large for it, but just a bit." "It's weird. I hate to say it, but it kind of suits me. Not that I look like a girl or anything..." "Just like a really cute boy in a dress. Your face seems to work really well for this. Do me a favor?" she asked. "What?" "Go down to the bathroom and shave really closely." As I went down the stairs to shave, I noticed how the dress bunched and flowed around me. The hem was limiting, and I couldn't take full steps until I hiked it up the way I'd seen girls do. I caught a glimpse of myself doing this in the hallway mirror and chuckled. Once in the bathroom, I washed my face and did a once over with an electric razor, then found my safety razor, and gently shaved against the grain until the surface of my face was smooth to the touch. I didn't have very thick whiskers, and shaving this way made the beard shadow almost disappear. Then I hiked up the dress and climbed back up into the attic. Emma was waiting for me. "Oh yeah, that's much better. Facial hair and fancy dresses don't work well together." "Well, I like handlebar mustaches on women. That's kind of cute," I joked. "Seriously, it's really interesting to see you like that. Makes me wonder why they don't let boys wear dresses all the time." "Do you think I look like a woman?" "Sort of, but I still see you as a boy. Maybe I'm just biased because I know you. You have a really good face for this; it works both ways," she said brushing some of my hair aside. "Well we should probably get cleaned up and go have dinner." "You haven't eaten yet?" "No, I was waiting for you." "Aww, that's sweet. Let me take one last good look and then let's go." She put her arm around my waist, pulled our hips together, and looked at us in the mirror. I looked uncomfortable but Emma had a peaceful happy expression. Then we took off the dresses and went down to eat. Emma started playing dress up at least a little each day. Afterward, she'd do her makeup and come down and hangout in whatever fancy costume she'd tried on. There was a lot of variation in the clothes although the most common theme was a sort of faux 1800s style that was updated to be a little less, how shall I put this, modest. We worked in SF on Wednesdays and Thursdays and spent the rest of the week telecommuting from home. Emma was usually most excited to play dress up on Thursday evenings about an hour after we got home. One week, she grabbed me by the arm and pulled me up to the attic. "This will just take a second. I want to try something again," she spoke trying to downplay her own excitement. "Me in a dress?" "Well yes, but just for a second. I've just been thinking about how you looked and wanted to try something." "What did you have in mind?" I asked, rolling my eyes. "It's just that you didn't fill out the dress quite right. I wanted to give it another try this time with some improvements." "Improvements?" Emma held up a bra that was black and lacy, and fitted it around my chest. She filled the cups with bags of birdseed to give them the weight of real breasts and fidgeted with the bra straps until they hung right. Next she produced a fairly plain pair of black mary-jane shoes and had me put them on after the dress. "See how it just hangs better?" She said, gazing at me through the mirror. "Yeah, but it's weird to see myself with boobs. I guess it does make the dress look better." "And the shoes don't look as out of place as standing there in bare feet." "It kind of looks like someone photoshopped my head onto a different body." "Here let's try a different dress." She helped me put on the red western dress she'd initially tried on herself. It was lower cut so that some of the bra was showing, though it wasn't obvious. It was a shorter dress, and we could see my legs. "My legs look really hairy," I said. "Yeah, why not go shave them?" Emma asked coyly with a lifted eyebrow. "This is starting to get weird." "Well that's what makes it fun... I'll help." The house had an old-style cast iron bath tub. It was large and stood on four legs. Emma got into it with me and helped me shave my legs. I was about to get out, but she nudged me back in and shaved off the rest of my body hair explaining, "Why not? Let's just get it all done at once." We went back to the bedroom, and I tried on the dress again. "Now you look sexy," she remarked playfully, ogling her eyes at me, "God! look at those legs." "They feel a little itchy." "Oh yeah, you probably need some lotion for that." Emma knelt beside me and proceeded to rub moisturizer onto my legs. She had to reach up under my skirt to do so and when she got to my inner thighs we were both breathing heavily. She coaxed me onto the bed, and we made love with Emma on top and me still in the dress. I fell asleep afterwards and took a short nap only to be woken up by Emma's gentle nudging. "What did you think of that?" she asked. "Why do you like me in a skirt so much?" "I don't know, it's something new. It's fun to play with you as my dress up doll." "You're turning me into your own personal transvestite aren't you?" "Well, you seem to like it. It's not like it's a lifestyle thing. Just something to try. Not like anyone will see you out here is it? I'm sure we'll get tired of it eventually and move on, but you know what they say about regret?" Emma started playing with the edge of my skirt. "It comes with lace?" She run her hands along my legs and softly tickled my toes, "You regret what you don't do, not what you do. What's the worst that could happen?" "You could like it." "Don't you mean... you could?" she asked. We made love again, and I fell asleep in the dress until morning. * * * One Saturday, I'd driven into town to buy groceries, and when I got back I found a woman wearing a black satin dress with white trim cleaning the house. On closer inspection, I saw that it was Emma. She even had on a white maid's headdress and seamed stockings with little black bows in the back. The dress itself was knee length and had long sleeves. It was frilly and sexy, but it wasn't lingerie and looked like it could be worn comfortably all day. "When did we get a maid?" I asked. Emma smiled. "I found the uniform about an hour ago. I thought it might make the house work more... entertaining." "You're having fun then?" "This is embarrassing, but whenever I catch a glimpse of myself in the mirror I think it turns me on a little." "Well, I'm certainly enjoying the view. Please, feel free to wear it whenever you like, and I'd feel guilty if I didn't ask, do you need any help?" "Aww, that's sweet. Why don't you just go and get dinner started? And I left something for you up in the bedroom." "Oh really?" I should have guessed, but finding a French maid's outfit laid out for me on the bed gave me quite a surprise. My face flushed with embarrassment, but it was exciting. Emma had left a little note that said, "Just for fun, take your time figuring it out," and she'd drawn a little heart under the words with a lipstick kiss in the middle. The dress was similar in style to the one Emma was wearing, though not an exact match. I started with the underwear, putting on the bra and a white lace garter belt. The stockings were a new experience, but I rolled them on the same way I'd seen Emma do it, and then latched them to the belt. The uniform came in two pieces: A black dress as a base and a lacy white apron. Thankfully, the dress buttoned up the front, so I didn't need any help with that, but I struggled with the apron a bit, trying to tie it behind my back. I felt a cold shiver run down my spine as I donned the headdress, followed by a warm feeling that flowed out of my heart filling the rest of me. I slipped on the mary-janes and went to go show Emma. Her eyes lit up, but she didn't say anything. Instead, she took a minute to straighten my stockings and retie the apron until it looked perfect. She took a step back. Then finally she exclaimed, "Look at you!" "You like it?" "You look perfect! Thanks so much for putting it on. You didn't have to. Come look at us in the mirror. We look like the servant girls at an estate." "This has got to be the weirdest thing I've ever done." "Come on, weird but fun. Anyway, why don't you go get started in the kitchen. I just need to finish up sweeping the floors." It was hard to cook without looking at what I was wearing, the stockings tugging gently at my legs whenever I walked. Emma finished up, and I heard her go upstairs to take a quick shower. A few minutes later, she came back downstairs wearing a flimsy pink house coat. "I finished my chores, so I figured I'd just come down here to take a break and watch you work for a little while." "Watch me work?" I asked. "Well, yeah. You do look really cute," she said rubbing her sides. "Besides I can pretend I'm a rich lady with a maid servant and everything." "That was your plan all along wasn't it?" "Maybe..." she said running her finger just below her lips. We didn't take it too seriously, but she kept me in the maid's dress until we went to bed. She referred to herself as Mistress, using the third person, until I started calling her Mistress too. * * * The next week on the way home from SF, Emma had a package. When I asked her what was in it, "You'll see," is all she'd say until we got home. Once we arrived, she led me up to the bedroom. "Well honey, remember when we had that really cute maid last week?" She asked. I rolled my eyes. "Yes, what does Mistress want this time?" "Just I've been thinking... since we're both having fun, let's take it up a notch... It'll be exciting." She opened the package. At first I didn't realize what I was looking at, but then I saw makeup and what looked like fake breasts. I found myself taken aback. "That's a bit much... isn't it?" "That's the point... isn't it? We've joked about you becoming a transvestite, but I think we both know where this is leading, and I think we both really like the idea. Anyway wouldn't you like to try taking it just a little further?" There was an all too devious smile across her lips. "Will this make me gay?" I joked. "No, not necessarily, but it will make you my little sissy maid, won't it?" She looked at me with puppy dog eyes. "You'd like that wouldn't you? Now go get shaved," she said in a playfully authoritative tone. Again, I returned to the bathroom and cleaned my body. Once I had finished, Emma came in holding a pair of breast forms. She sprayed adhesive on them and glued them to me. They pinched the sides of my chest together to form cleavage and filled out the rest with silicone. After waiting a few minutes to dry, she had me try bouncing up and down to make sure they were firmly attached. Honestly, I didn't know if I could pull them off if I wanted to, but she assured me the glue would wear off overnight. We did the garter and stockings again, but this time Emma made sure I knew how to get the seams straight. Next she had me step into a pair of padded panties that made my ass stick out. Though thick, they provided extra padding and felt oddly comfortable when I sat down. After I put the dress on, Emma showed me how to tie the apron right by myself. We hadn't put on the headdress yet and instead she led me into the bathroom where she sat me down in front of the makeup mirror. She applied a cool creamy coat of foundation to my face followed by blush and powder. "I've been dying to see you like this." She smiled, gliding a finger across my cheek. "There's not even a hint of a beard. Your face looks really soft." She explained everything as she went along and tried to keep the eye makeup simple at first so that I could replicate it if I wanted to, but then she broke down and went all out applying shadow, liner and mascara. She took out a little bottle of red. "What's that?" I asked. "It's lipstick." "I've never seen lipstick like that before." "Oh, I got this so you wouldn't have to worry about it coming off." "Is it permanent?" "Wouldn't that be nice? It's just long wearing. You'll need to use soap if you want to take it off." She sshhed me, had me part my lips, and pulled the applicator across them. When she was done, they were a deep burgundy red. She glued false nails to mine and colored them in the same shade. "Oh, I've just had an idea. We really should have done this first, but it'll be okay," Emma said, then plugged in her curling iron and went to work on me. A few minutes later, hair cascaded smoothly down across my shoulders in loose waves. I slipped on a pair of black pumps, and Emma stood me before a full length mirror. The change was incredible. "I can't believe it. I look so sexy." "Are you turning yourself on?" she asked. "A little. I make one hell of a sexy maid." "Not quite yet..." Emma turned me to face away from her, placed the headdress in my hair and tied it securely. "There, now you're Mistress's sexy French maid Julie." "So, you're not going to be a maid?" "Ha you wish! But since you've been such a good little maid servant, you can help Mistress get dressed right before you attend your chores." * * * We got into a rhythm where I'd dress up and be Julie at least once a week. I had a hard time doing it more than twice a week because although I don't have much of a beard, I do have delicate skin, and frankly I'd get razor rash. Emma never quite knew how to take this and often seemed short with me whenever I'd opt out of playing Julie by mentioning it. Then for our anniversary she gave me a little surprise. I opened the pink envelope near the fireplace in the living room. "It's a gift certificate for hair removal?" "Well, you're always complaining about shaving. You know, you can get it lasered off once or twice before really any of it stops growing back permanently, so just look at this as a little preview to see if you like it." We stayed a day late on our next trip to SF so I could go by the laser clinic. The whole procedure took about an hour and a half, and left my skin red and bumpy. It wasn't until about a week later that the hair dropped out, but when it did my body and face felt smooth and soft... like a woman's. After the second treatment, Emma had another surprise for me. When we got home she showed me a closet full of seven maid's uniforms each one a different style or color. I stood there silently until Emma poked me in the ribs saying, "Pretty nifty hunh? One for every day of the week... I was thinking now that you don't need to worry about shaving maybe you could stay Julie for a little while... just for fun." I felt cold sweat trickling down my sides and something down near the pit of my stomach buzzing. I managed to reply, "I don't know what to say, this is a little overwhelming." She'd noticed my reaction, and responded by holding one of the uniforms up to me. "Just say yes! Think of it as a game, a challenge to see how long you can stay Julie. What do you think?" "How would that work?" "You know, like you're playing a part. Just act as much like my maid as you can for as long as you can, and I'll try and act like a proper mistress, enforce discipline and all that. Just to see if we can keep it up, just for fun." "It does sound like... but I don't know. Being Julie is a little demeaning." "Aww, come on we both know you like it," she said, picking at my shoulders. "Maybe sexually... yes..." "What is wrong with that?" She grabbed my bottom. "Does having a week or two of sexual fun disturb you so much?" "A week or two?" "Yes! Let's take next week off, or just make up some excuse so we can work at home. It should last at least as long as that." "What do you mean, could it last longer?" "Oh wouldn't that be too bad?" Emma said examining her nails. "Actually, I am a little curious." "What do you mean curious?" "It's just that it's been pretty easy for us to slip into these roles. Even if we enjoy them, I just wonder if we could get used to them... "You think I could get used to being your maid?" "Don't get my hopes up, but I have a feeling we're both going to like this. If we keep an open mind and have fun with it, we might grow accustomed to it. As soon as it becomes something one of is just enduring, we should quit. Let's just look at it as a sexy little experiment." "I guess I could give it a try... just for fun, but it'd be quite the change to go from your husband to your servant." "I know! and if it just so happens that we find we prefer living that way, what's to stop us?" she said and ran her tongue across her lips. Then she helped me get dressed. We'd start every day dressing me up followed by an inspection, and then I'd help her get dressed and go down to make breakfast. She spent most of the week dressed as the lady of the manor, usually in some sort of formal dress or gown. One day she wore riding clothes. My maid's chores weren't too demanding, and it did seem more like a game than anything. Whenever I saw myself in a mirror, I'd laugh at first but then find myself enthralled by my own image. If I didn't try to see a man I couldn't see one at all. Emma would help by giving me pointers on how I could act more girlie, walking with my legs together and a swing in my hip, talking more softly and just generally being feminine and subservient. I was still working remotely, though in a dress and heels. On the few occasions I had to call into work and use my regular tone of voice, as soon as I hung up the phone we'd both break out laughing. Emma played at being more demanding and authoritative. She was never mean or cruel, but while I was doing my chores she'd take up a haughty attitude with me, which honestly turned us both on a great deal. * * * "So, Jules how do think our little game is going?" Emma asked, not looking at me as I handed her a hairbrush. "Well, it's a lot of work. I've been getting up a lot earlier then I'm used to, since I need to do my makeup... Mistress." She smiled when I said that. "It's taking you that long? You do look really cute. I love how you did cat's eyeliner today. But two hours?" "It only takes me about an hour to get ready, but I always used to get up after you. So now I need to get up earlier to help Mistress get ready." "Mmmm, yes. Mistress likes that." "It's funny. I don't think I've heard your real name for a while," I said and Emma raised an eyebrow, smirking at me. "Oh, sorry... for a while, Mistress." "That's better. I love it when you say that. You know every time you do, you look at me in the cutest way. Like you're waiting for approval." "Do I really?... Mistress." "Hehe, yes you do, and every time you do, I think about how you used to want to be so macho for me, to prove you were a real man. I look at you now, now that you've put all that aside, and you please me in a way you never could before," Emma said looking me in the eye. "It is quite a change, but it's just a game. It's just a little makeup and satin. That and doing whatever Mistress asks of me-- but that's not so different from being your man." "Yes, I like that part too. You're being so good today. Why don't you... I mean... go change into your pink uniform Julie." "Right now, Mistress?" I asked. "Yes, of course. I want to watch." I untied my apron, and folded it neatly on the bed. Then I unbuttoned the black and white dress I was in and stepped out of it. Emma watched as I rolled the black fishnet stockings down my legs and replaced them with lacy white ones. "But I guess what I was getting at, Jules, is are you enjoying yourself being my maid? I mean more so then when you were my husband." "Aren't I still your husband, Mistress?" "Yes, of course, but you know what I mean. Is it getting easier? Wait... that's not the right word. Is it more exciting? Wait... I'm not sure if that's the right word either." I finished latching the white stockings to my garter belt, and stepped into a lacy pink maid's uniform. "I think what Mistress wants to know is if it is more... natural?" "Yes! That's it." Emma tied the apron around my back, and fussed with my uniform picking at the edges and pulling at the straps until it sat right. She put her arm around my waist asking, "I mean given that it is just a game, and the charm might wear off, do you like your life more than you did a month ago?" "I do think it's more exciting, and I do feel close to you in a way I haven't felt before. I also feel like a total pervert, but that's getting less and less... Mistress." "Well we'll just have to be perverts together then," Emma said and led me to the bathroom. She wiped off the dark red lipstick I had been wearing with the black uniform and started applying a frosted pink. "I'm not holding you to this... yet, but..." She winked. "Supposing you would feel at least as good as the way you do about it now, I mean if the charm doesn't wear off... and supposing we could work it out financially, would you want to be my maid servant... from now on?" "Well, Mistress. Just supposing... That's a hard question." Emma pulled my hair back and started pinning a pink headdress into it. "Does that mean you could see yourself saying yes?" * * * Eventually, a month later when we needed to drive back into SF for work, the game ended. It was a silent drive in the car at first, but then Emma opened up. "So Jules. I was thinking about our little game, and looking online I think we might have developed a nice little fetish." "I'd say that's a safe assumption." It was hard for me not to end that sentence with 'Mistress'. "Well, I was wondering... I saw that there are these fetish clubs downtown and I thought, if you were okay with it, we might try going to one. You know just to see what they are like." "You want me to go out as Julie?" I asked nervously. "I think we'd fit in better at those clubs if we went as mistress and maid. Let's stay until Friday, try getting dressed, and drive past a club and see if we like the vibe. If we do we'll go in. If we don't, we'll just drive home." "Do we have any of our clothes with us?" She rubbed my knee. "Oh, I packed a bag." We stayed at a different hotel than usual, and before leaving we each got dressed. Emma had packed a black satin maid's outfit for me, and she wore a similar black Victorian dress. After dressing, I sneaked out to the car and Emma went back inside to checkout. We ended up driving past a club called "Bondage Bizarre" and camped out in a no parking zone for a few minutes, watching people go into the club. Most of them had on black goth or fetish clothing, and after we saw several transvestites enter, I finally agreed to get out of the car. I was very self-conscious people would be staring at me, and some were, but everyone seemed to approve. "Seriously Honey, in this light I doubt many people can even tell you're a guy," Emma whispered in my ear. "I should make my maid do this... but I'm going to go get us some drinks. Wait here." Emma disappeared into the crowd and emerged a few minutes later with a couple of gin and tonics and two girls dressed in latex. One of them was wearing a gag. "Sandra and Kim this is Julie, my maid. Julie this is Sandra and Kim." Kim was the one wearing a gag. "Hello Julie, nice to meet you. This is my pet, Kim," Sandra said and then turned back to Emma. "So how long have you been together?" "Oh, I started seeing Julie a few months back, but it didn't become a regular thing until last month." "Regular thing?" "Yeah we're pretty much living together now," Emma said. "I see a ring, are you two married?" "Oh, that's too funny. Julie is what's left of my husband Julian." Sandra's eyes popped open, and she gave me a thorough looking over. "You're doing a fabulous job. I wouldn't have guessed she was male if you hadn't told me." "Yes, she has a really good face for this. It's kind of funny too, neither one of us had been into any femdom stuff before, but she really seems to love it. Don't you honey?" I was surprised it was my turn to talk. I tried to think what a good maid would say, "Oh yes Mistress, it's a lot of fun." "Aww, that's sweet." Sandra interjected, "So how did you train her?" "Well, she's quite taken to it. It started as a game and has just grown from there." "Funny how things do that." Sandra patted Kim on the head. Kim rubbed up against her leg and started purring. Emma talked with Sandra for an hour or so who told her about a fetish group that did couples weekends. Emma told her about our house and offered that they ought to come up sometime. Then they both got very drunk, and I ended the night by driving everyone home. * * * The next day, I was wondering if I should go back to being Julie or not, what with our break in SF. The answer was simple when I found all my male clothes gone and a little note that said simply, "Just ask if you want them back, now get dressed and make breakfast." I found a new uniform in the closet that was made of vinyl and only resisted a second before I put it on. Emma was downstairs in a full length latex dress. "Glad to see you like your new uniform," she said looking me over. "I did some shopping at the club." "Yes Mistress. It's beautiful." "Guess what?" "What, Mistress?" "Sandra and Kim are coming up next weekend. I invited them, and they said yes." I was a little disturbed she hadn't consulted me, but I kept it to myself. I supposed it was just part of the game. "Yes Mistress. Do you need me to do anything?" "I'll just need you to make up a guest room for them in a few days. But right now you can come over and shine my dress. There's rubber polish on the counter." * * * On Friday we were both in formal attire waiting for the girls to show up. I was wearing a blue housemaid's uniform and Emma was wearing her riding outfit with a red velvet jacket, white pants, and knee high boots. The girls arrived underdressed. They apologized, stating that it was more comfortable to travel that way. Kim just looked like a goth girl in sweats, and they decided to put off getting dressed until the next day. I played the maid, serving them at dinner. Kim kept eyeballing me like she couldn't believe what I was doing. She suggested several times that Emma should make me sign an employment contract, but Emma just seemed bored with the idea. The next day, Sandra came out of the bedroom wearing a skin tight leather outfit, and Kim was on all fours dressed as a pink latex cat. She had on little paw mittens over her hands that kept her from using her fingers, a bit in her mouth that kept her from talking, straps around her hind legs that kept her from standing up, and a collar around her neck with a leash that led up to Sandra's left hand. I invited them to breakfast, and Sandra asked if I could put some milk in a bowl for Kim. Emma seemed elated when she saw Kim. "She seems completely different as a cat." Sandra replied, "Yes, I think she's fairly unhappy as a human being, but she likes being a cat. It suits her." Sandra reached down and scratched playfully at Kim's neck. "That's right, how's my little kitty, don't you like being a cat, yes you do." "I think it's the same sort of thing with Julian and Julie. Don't get me wrong I love Julian, but Julie just loves being my maid. Don't you Julie? It's okay to speak your mind." "Oh, I just think of it as a kind of game, and I'm embarrassed I like it, but I do, at least for now, and it's really been quite exciting." Sandra asked if I would go and take Kim out for a walk, which I did. It was an awkward experience but neither of us broke character. I didn't think of it, but you don't generally walk cats. Still, Kim seemed to enjoy it. Eventually Kim warmed up to me and I was startled several times that evening to look down and see her rubbing up against my legs. * * * After Sandra and Kim left, Emma strode up to me as I was cleaning the guest room. "Guess what?" Emma asked in her oh too elated tone. "This weekend with Sandra and Kim gave me some ideas and I was thinking maybe we could take things up a notch?" "Another notch? Let me guess Mistress wants me to be her cat now?" "Just on Saturdays, it'll be fun, you'll enjoy it... just kidding dear. So tell me how did you enjoy being a maid for our guests?" "I don't know. I guess it was fun to see other people doing the same sort of thing as we're doing. It made me feel more normal- in a way." "So you won't mind being the maid if we have more guests?" "Depends, I could be talked into it as long as they don't look at me like a-- freak." I turned and started putting fresh sheets on the bed. "No, I get it," Emma said as she gently adjusted my stockings, "It's kind of cute you don't want people to know that my husband has become my personal, transvestite, live-in, maid." "That's not quite how I would have but it, but I guess you've got the gist of it... Mistress." "So... is it not so much being the maid, as having people know that you used to be-- or what I mean is, that you're really a man?" She gently pushed down on my shoulders, until I was kneeling before her. She ran her fingers through my hair, and adjusted my headdress. "I don't know. This is just a game isn't it?" "Is it?" She ran one of her fingers under my chin. "Just like yahtzee is it?" "Well no... Mistress... this one keeps getting odder and odder. I feel like your doll or something." "I thought you liked that." "I do," I replied sheepishly. "Well, I know something that'll take your mind off of it, at least for tonight." "What's that?" "I've decided I want to try my personal transvestite maid doll with red hair." I looked at the flat expression on her face with a puzzled look, until she cracked a smile, and led me to the bathroom, where we spent the evening dying my hair auburn red. * * * By the end of the year, I wasn't getting down to SF very often for work. They were comfortable with me working remotely, so that I'd just call down whenever I had to speak to someone. Eventually we arranged to be working on contract, and even if it meant neither one of us was going to advance within our companies, the money was slightly better, and we found we didn't need to spend as much time working. One evening, we were on the porch watching the sunset. My head was resting on her shoulder and Emma stroked my hair as she gazed off into the distance. "I wonder how much like a girl we could make you look," she said into the air. I sat up and looked at her. "I thought we were basically all in already." I thought about adding Mistress, but Emma didn't seem to be in an authoritative mood. "Sure you dress like a girl, and you are a super cute maid. I just wonder if we could push it just a little further so that if you were dressed no one could tell, even under scrutiny." She stroked the small of my back. "I keep daydreaming about it, and I get more and more curious. I think maybe we should try and get you to lose a little weight. You're trim for a boy but I wonder what you would look like if you were downright skinny, you know like actors do for parts. You can always gain it back." She gently picked at my blouse. "What did you have in mind exactly?" "Well, you're just a size too large for most of the clothes in the attic. They fit, but not quite right. I was thinking maybe take you down a size and a half, just to where they start to hang off you rather than you squeezing in. Maybe lose 10 or 15 pounds." "I don't know. Are we talking cabbage soup? I don't want to be hungry all the time." "No no, if we just cut down your portions a bit, and you stop drinking soda, that should do it. Also I was thinking we might try a corset. Nothing too constricting, just to pinch your tummy, it should actually make the diet a little easier." "I guess I could do that. Is this going somewhere?" "Well I did have another little idea..." "I'm almost afraid to ask..." "I was thinking as part of slimming down you should change how you workout. Stick to aerobics and cut out anything upper body. The upper body is the most telling part and if we could get your arms to slim down, just a little, it might make a world of difference." "You want me to become a ninety-eight pound weakling?" She cracked a smile. "I wouldn't have used those words, but... you've hit the nail on the head. Besides when girls are ninety-eight pounds their called models, and even if you lost fifteen pounds you'd still be well over ninety-eight. Come on, it'll be super easy to gain the weight back, if you want to. Plus, I was considering doing a little weight training myself." "Yeah?" "Well most of those clothes are just a little too large for me, so I was thinking maybe I should buff up a little, and try and get a little muscle. You've been doing most of the work, so it might be interesting for me to take a turn." "You want to get bigger- stronger than me?" "It sounds like fun when you put it that way, doesn't it?" A few days later, Emma started helping me into a corset in the mornings. I cut back on my eating and started riding an exercise bike about an hour a day while Emma started lifting weights and eating a little more. My maid's uniforms started fitting better, and whenever we did get down to SF I noticed my shirts felt loose. Emma enjoyed getting stronger and would frequently 'show me her guns'. We had weekly arm wrestling contests and my advantage was starting to wane. Then finally, the week came that Emma beat me. We were in the kitchen both of us in our workout clothes, both dripping with sweat. The look in Emma's eye was like a boxer who'd just knocked down an opponent. I looked down at my arms and they looked impossibly skinny to me. What we'd been doing started to sink in and a cold shiver came over me. "I know something that might cheer you up," Emma whispered. She came round the table and wrapped her arms around my waist. "I'm going to take my sweet little maid up to the bedroom and I'm going to hold her down and make love to her and there's nothing she can do about it, because Mistress is stronger than she is." * * * "See how much better that fits you," she said. It was the next morning and I was putting on a yellow and white uniform. Emma had taken to wearing different riding outfits all with pants and high boots, she still looked very feminine, but she looked stronger and seemed more sure of herself. "I suppose it does." I chuckled a little nervously. "Do you think we achieved our goal?" "You mean can you pass one hundred percent for a girl now? We're getting close. You're starting to not look quite right as a guy." "Really? How do you mean?" I was concerned. "Just that you're too skinny. It looks like you might have an eating disorder or something, but don't worry in SF there's plenty of guys skinnier than you. Still, a few people were surprised that you were my husband." I jerked my head to look at her. She giggled. "Just a few of my girlfriends from work thought you were a gay friend or something. They weren't shocked or anything, just one of them was a little surprised. But... back to you looking like a girl." "Yes?" "There's one more thing I'd like to try, if you're game, but I'd like you to think about it carefully. I was thinking it might help a lot if you got your nose straightened and slimmed a little." "A nose job?" "I don't mean give you a girl's nose, just make it a little more... androgynous, so it'll still look fine when you switch back. Just a little slimmer and a little cuter. It bends a little to one side anyway. It's not something you really notice on a guy, but when you're a girl as cute as you, any little imperfection..." I blushed when she called me a cute girl and turned to a mirror, insecure about my nose. I hadn't really seen anything wrong with it, but she had a point. A few weeks later and I was down in the city getting my nose reshaped to be slimmer and ever so slightly upturned. It took about a week to recover, and I spent most of that in bed. Emma attended to me and some of the time, just for fun, she wore a nurse's uniform. Oddly, the rest of the time I heard her pushing around furniture and one day a delivery truck came by. Some men carried things up the stairs. She asked that I stay in the bedroom the whole time, saying that it would all be a wonderful surprise. She kept many of the rooms locked until after we got back from having the splint taken off my nose in SF. When we got back, she did a great unveiling. The house is large with six bedrooms, only two of which we were really using, one for sleeping, and one for Emma's office, mine being in the den. The four open rooms in the house were now fully furnished with king sized beds, dressers, chairs, tables, and various pieces of local art. "What's all this for then?" I asked. "It's for our next game! Oh you're going to love this, plus it'll make us some money." She looked at me with a sideways glance. "Are we going to rent out rooms?" "Exactly! Well sort of anyway. It's just that we have such a big house and we're in wine country and near the highway. I've been talking with Sandra, and she mentioned many couples go away on fetish weekends. I was thinking we could start a B and B, just on the weekends, for fetish people. It might be fun to spend more time around similar couples. Plus Honey... now you can try being a maid... for real." "I guess I do feel a little isolated. I'm not sure how well I can handle eight guests." "That's just your persona, I'll help with the work, but I still get to be the Mistress of the house. Just think about if we pull it off though, it'll be fun, we'll make friends. Plus maybe, occasionally... we'll have a non-fetish weekend, and then you'll just be a regular maid." "This is a lot of plans to be making without me really having a say." "Aww, I thought you liked that part," she said stroking me through my pants. She noticed my arousal and added, "Well at least a part of you does." "I can hardly believe it myself." "That's what makes it fun. We know we can stop at any time, but let's keep going for a while because it's fun to be perverts. Still I wonder if you'd known that buying this house meant you were going to spend most of your time in a skirt and heels, would you ever have done it?" "If that was on the real estate page, no I probably wouldn't have." I rolled my eyes. "Care for a little maid training?" "What kind of training?" "I was thinking about a little obedience training... should be fun." "Something else is up, isn't it?" I asked. "You won't know until you get out of those awful boy clothes, and Julie plays with me dressed in her naughtiest maid's uniform, you know the little vinyl number we like so much?" An hour later, I was dressed as Julie again, and Emma was lying out on the bed in a latex catsuit. "That's better, sweet thing. You're looking all nice and slutty," she said looking me over. "Thank you Mistress, you look really... slutty as well." She smiled. "Ready for the next step? I figure with your responsibilities growing, it might be a good time to take your training up a notch..." She winked at me slyly. "You know just for fun. It's about time we made you a proper sub." I gulped. "Mistress?" She patted the bed beside her. I sat down, and she wrapped her arms around me. She continued, "It's just that I've been researching submissive sissy maids, and it seems like there is an element we're missing, something I'd like to try..." She slipped off my panties and began rubbing my cock. She pulled a locking metal penis-shaped tube out from under a pillow, licked it, and kissed the tip. "I very much want to make you cum, to lick you all over, and make you cum again, and again, and once you're completely spent, once you feel like you won't cum again for a week, I want to lock you in this. Does that sound like fun to you?" "Yes, Mistress." She made good on her promise, pleasuring me over my entire body, she incorporated the tube into our love making, using it as a dildo, first on herself, and later on me. As I lay exhausted on the sweaty sheets, she brought out a bowl of warm water and cleaned my genitals thoroughly. "It's about that time isn't it?" she said, stroking me with the tube. "How does it work?" I asked. "Well, it's like a little puzzle. First I slide on the base," she said, placing a half open ring behind my testicles. "Then I secure it so it can't come off." She popped a top piece on, closing the ring around my shaft, with three pegs extending forward. "Next I slide you into your new home." She placed the holes at the base of the metal tube onto the pegs, carefully nudged my penis inside, and slid it closed. "And finally, I lock it all up nice and tight, so my naughty little maid can't get at it." She held a lock in front of my face, kissing it. Then she slowly pulled it down along my body, until I felt her hand holding the tube. While she kissed me deeply, I felt it click into place. "And from now on, if Sissy ever wants to cum, she'll need Mistress to unlock her first." "From now on?" I asked. "They say it makes a sissy very... obedient. And if Sissy keeps forgetting to say Mistress, she'll never get to cum." "I'm not sure about this, Mistress." "It seemed like a good idea a little while ago didn't it? You agreed to it, and this time I'm going to hold you to it." She winked and started rubbing the outside of the metal tube, though I couldn't feel anything, I began to get aroused again, but quickly found it going nowhere. "If you want relief, you're going to have to show me special attention... Then maybe... in a few days... we'll see." She was still talking playfully, though she seemed more intent than usual. "A few days?... Mistress." "I do get some time to try out my new toy don't I? Some Mistresses leave their sissy maids locked up for months at a time. Don't worry, I'm not doing that... yet. I just want to see how you respond to it, how obedient a sissy you'll become. Besides you did agree to it, and you've only been in it a few minutes." "Yes you're right." "I told Sissy not to forget to say Mistress. Just for that, I'm leaving Sissy in there for at least three days." "Three days?" "Now it's up to four, want to try for five?" "No Mistress," I sighed. "Sorry Mistress." "I know this seems a little extreme, but I want to see what it's like, having you totally submissive. Maybe we'll end up just using it on a weekend now and again. But I think we're both going to love it..." she said cracking a sly smile, "and it'll become a fulltime, forever sort of a thing. You know, just for fun." Starting the next day her tone became "stricter". If I didn't hurry to a task, she'd get angry with me. Occasionally I'd catch her off guard, like when she was just waking up in the morning, and she'd look at me with her soft eyes, before she'd catch herself, and slip into a cruel smile. Meanwhile locked in my tube, I was becoming more and more anxious, trying to please her just so I could get relief. I was having a hard time getting to sleep, and by the third day I was so tired, I slept through my alarm, and she informed me I'd just added two more days to my "training period". I forgot to say Mistress once more, and she added another. On the seventh night, as I was scrubbing the floors on my hands and knees, I heard a bell ringing from upstairs. I followed it to the bedroom, where Emma was laying out in the same flimsy pink house coat she'd worn the first time she'd watched me do chores as her maid. She had a bell in one hand. "Go get me some wine, Sissy." She smirked at me. "What kind Mistress?" "You shouldn't have to ask, and here you thought you'd be getting out tonight." "Yes Mistress." My voice cracked, and I rushed out of the room, not daring to let the exacerbation show on my face until Emma couldn't see it. I filled a glass of merlot, put it on a silver tray and brought it up to her. She sipped it, then quite suddenly poured it out onto the bed sheets. "I wanted white," she cackled, "that's one more day for bringing me the wrong wine, plus a week more for ruining the sheets." "Sorry Mistress," I said shaking. "Sure you are, or maybe you just like being locked away so much, you're fucking up on purpose, so I'll keep you locked up forever." "No Mistress." She arched her brow. "Don't you ever contradict me... ever. That's another week." "Sorry Mistress." "So you admit you're fucking up, because you want to be locked in chastity forever." "Yes, Mistress." "I want to hear you say it." She pointed on the floor beside the bed. I knelt down, then addressed her, looking down at the floor. "I fuck up on purpose, Mistress because I want to be locked up forever." "No swearing, that's another day. And would you like it if I never let you cum again." I didn't know what to say to get out of this. "Yes Mistress. I would like that very much." "You're useless as a man you know that, don't you?" "Yes Mistress." "Still I suppose we can find other parts of you that are useful." She placed a stiletto clad foot in front of my face. "You need to show me you can use your tongue, start licking." She'd positioned her foot so I'd have to look up at her to get it in my mouth. When the tip of my tongue first made contact, Emma giggled. The black heel was at the very least clean, and as I started to lick, Emma slowly pushed it farther and farther into my mouth, until I started to gag on it. She slipped out of the shoe, and just at the time I let it fall from my lips, she spread her legs. She teased at my hair, slowly slipping off my maid's cap, before pulling my face down on her pussy. "Let's see what else Sissy can lick with that." She came twice before she let me up, and the second took a long time. Finally when I thought we were done, I felt her reaching behind my head. She was strapping something to me. A rubber ball pressed against my lips. "We're not done yet. Open up and let it in." I did as I was told. She led me up on to the bed, and had me lay down on my back. She then began tying my wrists and ankles to the bedposts with rope. When she was done, I felt a click come from the tube, then she very very slowly pulled the tube off my cock, leaving the ring in place. "Feels good doesn't it?" Her hands ran down my sides, and found their way onto my inner thighs; she began caressing them. My penis painful at first, was becoming erect. "I suppose on one hand, you have been a good little sissy maid, and it would only be fair to give you some relief." "But on the other hand, you did say you wanted to be locked inside of that tube forever. And that you never want me to let you cum ever again. Since that's the case, maybe I'll just have to stick you right back in the tube. Of course then we'll need to do something about that nasty little erection you seem to be working on." I felt something very cold touch the base of my penis. Emma rolled her eyes. "I was reading online that you can get rid of an erection by icing it, effective if not very satisfying." She continued to hold what I now assume must have been an ice pack against me, until I started to get numb, and slowly but surely the erection went away, until it was so cold I could just barely feel Emma playing with my flaccid member, kneading it between her fingers. She continued, "Even if you don't ever cum again you do require cleaning, from time to time, for hygiene." She started washing my genitals with a very cold soapy towel, dipped in ice water, then dried it off with another towel. She climbed on top of me looking me in the eye. I felt the metal tube rubbing against my cock, the opening gently kissing my tip. She smirked. "Oh well, I suppose you did say you wanted this." The opening pressed against me until the tip slid inside. "We both knew where this was going, and we both really liked the idea." I felt the tube slide back into place against the base, and she reached over and turned off the light. The room became pitch black, and I shivered as I felt a tiny little click. Silently she left the room, and I stayed there in the darkness wondering just what I'd gotten myself into. Exhausted I finally slept. The next morning, I was no longer bound, and Emma was curled up with my arms around her. I carefully reached down to find the tube was gone. She felt me moving and woke up. "That was some fun wasn't it?" she asked. "I was thinking about letting you out last night, and fucking with you still tied to the bed, but I thought it would be more -memorable- if you finished the night wondering if it was going to be forever." "Is it over then?" "Oh... It doesn't have to be, you haven't come yet. I could lock you right back up. Or we could do it right here and now, you must be ready to burst. Or..." "Or what...?" "Or I could tie you down to the bed, and when I'm done fucking your brains out decide whether or not to lock you back in," she said as she climbed on top of me. Once we had finished, I found myself helpless, tied to the bed with Emma snuggling in beside me. She was holding the metal tube, running it up and down my body. "I bet I know what you're wondering," she said in a sing song voice. "I bet you do too." "That's no fun, I want you to guess." "I'm wondering if you're going to lock me back up, in chastity... Mistress." "I could, if that's what you really want?" "It is kind of stressful. And it might be thrilling, but I wouldn't describe it as fun." "Well for me too. It takes a little bit of work to be so strict you know, plus I don't get to play with anything good, what with you locked up in there," she said, holding me in her hand. "So you're not going to?" "Maybe we can give it a break. That way it'll be exciting the next time I put you in it. Also it'll be less stressful, so we can probably go a little longer. Then the next time after that, a little longer... and longer. Who knows, maybe we will get you into it permanently. It'll be fun to try anyway." "Maybe for you." "Well, I was thinking of something else. Maybe even more fun." "What's that?" She began circling my nipples with her fingers again. "Well I was just thinking, odds are we'll be doing this for at least another year or two. Don't you think?" "I hadn't thought it through that far, but I guess so." "Well, I was thinking, now that you don't go into work anymore... and since you're living as a woman pretty much all the time... it might be fun if we got you... us... more to play with." "What do you mean?" "Well I was just thinking, it might be more fun if you spent the next few years, at least, with a pair of nice soft breasts for me to play with, you know, when I have you tied down like this." We both silently watched my penis become erect. "Plus really Honey, it might be easier if you were a woman fulltime. You seriously haven't thought about it?" "I don't know, I guess I'm a little worried how my friends would react." "Well, it's not like we see them much anymore, you've become a bit of a shut in. I think most of your friends would be cool with you being a woman, cooler than they'd be if they found out you were a sissy maid. I don't think of you so much as someone who passes as a girl, so much as you really are one." "It's just not how I'd expected my life to turn out. If it's a game, even if it lasts a few years, eventually everything goes back to the way it was. I guess that sounds... farfetched when I say it like that." "It's your decision honey, but I don't see why things can't turn out the way you've always wanted, just with you as a woman. So, how about this... either I put you right back in the tube and we can have a few more weeks of obedient sissy fun... or Julie and I go out on a date. Someplace normal... ish." "Are you blackmailing me?" "Yes I am, because we both know you like it." First posted on fictionmania. If you enjoyed the story please leave a review or comment. [email protected]