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HOUSE SITTER By Lisa Lovelace It was summer vacation, and mom was being a pain. Making me do chores around the house, telling me to go out and find a job instead of just sitting at home playing games, nagging me to get a haircut. I'd just graduated from Edina High, and I figured a guy was entitled to kick back for a while, right? I didn't have any big college plans, we didn't have enough money for that, but I could always enroll in community college for a couple of years and see where that left me. I was tired of living with mom, and I knew she was even tireder of living with me. She divorced my dad when I was young, which is why we had a nice house but not much money. He lived out in Arizona now and didn't help mom at all. She'd been used to a more comfortable life than we could lead now, and she resented it. She was finicky and high-strung, a perfect example of what they said Edina's city name stood for: Every Day I Need Attention. One day she opened the door of my bedroom and barged in without knocking. "I have a job for you, Logan." Annoyed, I paused killing aliens. "What kind of job?" "A fulltime job outside the house," she said. I liked the sound of outside the house. Wasn't so sure about fulltime. "Doing what?" "House sitting. I know a woman who needs someone to stay at her house and feed her cat for a week while she visits her mother." "In Edina?" "Minneapolis. Nice house in an older neighborhood." "What would I have to do?" "Make sure everything's secure. Feed and play with her cat. Keep the house immaculate. Don't break anything." I could do that. "I'd be paid?" "Two hundred for the week." "I'd be staying there? What about food?" "Two hundred will buy you a lot of pizza. She also said you were welcome to whatever you can find in the fridge or pantry." "Okay, I'll do it. Can I take my laptop?" "I don't see why not. All right, I'll tell Ms. Underbust. Pack yourself some changes of clothing and toiletries. I'll drop you off at her house this Friday and pick you up next Friday." ~ ~ ~ Mom drove off, and I mounted the stairs to Ms. Underbust's front door. It was a large, handsome house, probably a hundred years old, across the street from one of the prettier of Minnesota's ten thousand lakes. I knocked. A handsome woman answered. She was younger than my mom, maybe in her thirties. "Yes?" "I'm Logan Love, ma'am. Your house sitter." She brightened, introduced herself as Tina Underbust and invited me in. She wasn't wearing shoes and there was a rack of them by the door, so I took mine off before she had to ask, and was glad I'd worn socks without holes. Starting in the kitchen, she showed me around the house, ending in a guest room upstairs that she said I could use while I stayed at her house. It looked as though it had most recently been a girl's room, though the dominant color was baby blue instead of pink. I hauled my backpack up to the room and rejoined Ms. Underbust in the kitchen, where she showed me how to feed the cats and take care of their litter. As she showed me her household routines, I couldn't help admiring her. She wore an old-fashioned housewife's dress, black with white polka dots, snug above the waist and very full below it. It did a good job of showing off her breasts, waist and legs without baring anything. She was like if my mom had a cute younger sister. I felt myself harden in my jeans and hoped she wouldn't notice. She probably wouldn't, as I was not particularly well endowed. A horn beeped outside. "Oh, there's my ride," she said. She put on her coat and picked up her purse and suitcase. "Thank you, Logan! Text me pictures of my kitty! See you in a week!" Her heels clattered on the steps and faded. She'd told me she didn't expect any deliveries or visitors while she was gone. As far as I knew, I was on my own for the next week. Alone with little to do. In the house of a well-dressed woman. A woman who appeared to be just my size. Temptation. I'd always been attracted to women's clothing. I couldn't help it, I was born this way. I never had a chance to dress up at home because mom wore plus sizes, and my short, slight figure would be lost in her things. I wanted to check out Ms. Underbust's closet. As long as I looked but didn't touch, she'd never know, and as long as she never knew, there would be no harm done. I explored her closet and chest of drawers. Looked but didn't touch. The closet contained office wear - businesslike dresses and skirt suits, no trousers - and softer dresses for at home or special occasions. The latter included what almost looked like dance costumes: three knee-length swing dresses with snug bodices and full skirts, accompanied by white, pink and black crinoline petticoats. Perfect for old-time dancing, a side of Ms. Underbust that I hadn't known about. Temptation. I looked at the nightgowns hanging from a set of hooks: ankle and waltz- length gowns and robes and a pink baby doll. An ankle-length baby blue nylon nightgown caught my eye. Its shirred bodice was decorated with lace and ribbons, and it had delicate flutter sleeves. If I was going to give in to temptation and wear a nightgown to bed, it would be the one I'd choose. But I wouldn't! I wouldn't touch the clothes. Just look. Don't touch. The chest of drawers held a pretty collection of lingerie: panties, bras, slips, camisoles, hosiery, garter belts and a variety of foundation garments, also in white, black and pink. Nice things, nothing sleazy. Temptation. I resisted. Played games on my laptop. Ordered a pizza and ate it while watching her sixty-inch TV. Took a shower, put on the t-shirt and boxers I'd packed instead of pajamas, and climbed into bed in the guest room. Woke up in the middle of the night. Could not stop thinking about the nightgown. My boxers and t-shirt felt rough and uncomfortable. I climbed out of bed, took off my boy clothes, fetched the nightgown from the closet and let it slide down my body. I would wear only clothes that could go through the washer and dryer, and would launder them and put them back in place next Thursday. She would never notice. Having succumbed to temptation, I slept comfortably for the rest of the night. Saturday morning, I got up and puttered around in the nightgown for a while. I found some English muffins and had them toasted with butter and blueberry jam. The coffee machine looked dangerously complex, so I found a teakettle and made some tea. What would I do for the day? I tried to deny that I already knew, but it was useless. I had Ms. Underbust's entire wardrobe to play with, at least anything washable. In for a penny, in for a pound. I selected panties, a bra, garter belt and stockings, a slip, a petticoat, and one of her dance dresses, carefully noting where each item was and how it was folded or hung. Sitting in Ms. Underbust's bedroom, I put on her clothes. The dress had a white collar, a fitted bodice and a full skirt in an aqua and teal floral cotton print. Under it I wore the white petticoat. I had small feet for a man, and was able to slide into a pair of white sandals with a two-inch heel. For the first time in my life, I was dressed as a woman from the skin out. Oh, I was far from a finished product. I had to do something with my hair. I needed makeup. I had no jewelry. But looking at myself in the mirror, I saw a reasonably attractive young person who looked more female than male. In fact, she was rather cute. She was also stiff as a board. I practiced moving in the clothes, walking in the heels, feeling the dress and petticoat swish around my hips. I watched some YouTube videos on how to walk like a woman, and tried to place shorter steps on a straight line, which felt totally unnatural. I crossed my legs or kept my knees closed when I sat. I drew my arms in close to my body, let my wrists go limp but not too much so. I practiced a curtsy, and liked the sight so much that I did ten of them. Wow! If I only had a dance partner! (And knew how to dance, which I didn't.) Even so, I was wearing a sexy dance dress and all the feminine underpinnings, and I loved the feel of them. I spent the rest of the morning playing with my hair and experimenting with makeup. I tried parting my hair in the middle and tying it into pigtails with ribbons from a drawer of her vanity. It looked pervily juvenile, but no one could see it but me, and I have to admit it turned me on. Alas, Ms. Underbust didn't have a schoolgirl's uniform or little girl's dress in her closet. After an hour or so of creating makeup disasters and destroying the evidence, I decided to settle for eye liner, eye shadow, blush and lipstick, no mascara, and managed to achieve an acceptable result by using less than half as much makeup as before. Ooh! It worked. I was more than cute, I was pretty. It was an unnerving feeling. I was a boy. I wasn't supposed to be pretty. I had a light lunch of Greek salad with feta that I found in the refrigerator. Afterwards, I cleaned up the kitchen, tidied up all the rooms downstairs, emptied the trash and cleaned all the sinks and counters in the house. I decided to save the vacuum cleaner for tomorrow, and the mop for later. The house already looked better than Ms. Underbust had left it. I wanted to please Ms. Underbust. I spent the late afternoon streaming the movie of Emma, the Jane Austen novel, and fell in love with Anya Taylor-Joy's Regency gowns. I decided to watch it again tomorrow. As dusk fell outside, did I think what I could make for dinner with the ingredients on hand? I did not. I called the same pizzeria and ordered a large pepperoni. Only after I hung up the phone did I realize that I would have to deal with the delivery person en femme. My heart almost stopped. I rushed to the mirror to see what was most wrong about my image. It was the pigtails. They made me look like an idiotic infant. I untied the ribbons and hurriedly brushed my hair into a center part. It looked better. Not great, but better. My makeup was okay. Damn! I forgot nail polish. Nothing I could do about it now. The delivery boy showed up in fifteen minutes, which I spent terrified that he would read me as male. Finally, a knock on the door. The delivery boy looked me up and down. "One large pepperoni pizza, Miss," he said. I loved him for calling me Miss. I'd paid online using a credit card mom lent me, but gave him a five-dollar tip in cash. I devoured three-quarters of the pizza, saving the rest for breakfast. Oh! Life could be good here. Pizza for dinner and breakfast, something from their larder for lunch, and then pizza again for dinner... but pizza was messy... I'd have to be very careful not to get it on whatever I might be wearing. Maybe I should order something tidier than pizza... The week passed with me blissfully dressed in lovely women's wear during the day and a nightgown at night. I think I tried on every dress in her closet, except one or two that were so tailored that I was afraid of stretching them out. Ms. Underbust seemed to have a thing for vintage designs, and I, too, found them attractive. Thursday morning, I got fully dressed up in the morning and then realized I hadn't brought in the mail yesterday. I didn't want to change clothes and clean off my makeup, so... what if I just ducked out the front door, sashayed down to the mailbox on the street, grabbed its contents and sashayed back inside? Most folks on the street had probably already left for work, so it was unlikely anyone would see me. The thought of going outside en femme scared me, but I had to be brave. I opened the door and walked down to the mailbox, my heels clicking on the pavement. As I scooped the mail out of the box, a black Lexus with tinted windows pulled into the driveway, right next to me. A man sat at the wheel. He rolled down his window. "Hi, I'm Dirk, who are you?" I gulped, stood up straight, picked a girl's name out of thin air and said softly, "I'm, uh, Lisa. Who are you?" "I'm Tina's boyfriend." Oh my God. A complication I didn't need. "Is she home?" "Not yet. Tomorrow," I said. "And you're staying here? You're...?" "Oh, I, I live down the street, my mom knows her. I'm house sitting for her." "Yeah, she was visiting her mom," he said. "Yes," I said. "Well, nice to meet you." I was desperate to get inside the house and close the door. I should have changed my clothes. I should have changed my clothes. I should have changed my clothes! Any moment now, he's going to say, hey, wait a minute, are you...? But he didn't. Instead, he got out of his car. He was easily six foot two, a couple of hundred rather muscular pounds. "Hey, Lisa, I'm really thirsty. Can I come inside and get a glass of water or something?" Christ, no. He thinks I'm a girl, I'll be alone with him, totally vulnerable in my skirts and heels. "Uh..." "I'll be quick," he said. I sighed. "Come on in." I felt his eyes on my ass as he followed me into the kitchen. I got out a glass, filled it at the tap, handed it to him and retreated to the other side of the kitchen island. He raised the glass in an ironic toast. "Looking good, Lisa," he said. He set down the glass and circled the island, backing me into a corner. I got really nervous. He put his hand on my shoulder. I brushed it off. He raised it back to my shoulder. I tried to brush him off again, but he caught my wrist in his other hand, and in a moment, I was helpless, unable to get free of him. "Stop it! Let me go!" He ignored my protest. "You're so pretty." He kissed me on the lips. "No! No!" I was nowhere near as strong as him, but testosterone made me a bit stronger than most girls, and I was able to twist out of his grip. I put the kitchen island between us again. "Stop, or I'll..." Or what? He could easily overpower me. "I'll tell Ms. Underbust!" That stopped him. "Aw, sorry, Lisa, I was just fooling around. I wasn't going to do anything. Just one little kiss. No need to mention it to Tina." "Okay, okay!" I said. "Just keep your hands off. You can go now." He retreated from the house, got back in his car, drove away. I watched him zoom down the street and hurried back inside, where I broke down in tears. I consoled myself with the thought that at least he hadn't detected my real sex. I spent the evening laundering all of Ms. Underbust's things that I'd worn, hand-laundering the most delicate items, and putting them away exactly as I'd found them. I even ironed the slip I'd worn. I was back in my boy's clothes when Ms. Underbust returned Friday morning. She gave me a strange look. "I was texting with Dirk," she said, "and he mentioned that Lisa from down the street was house sitting while I was away." Oh shit oh shit oh shit. Oh oh oh shit. "The thing is," Ms. Underbust said, "I don't know any Lisa from down the street. Did you have a girl named Lisa staying here?" "No, ma'am," I said. She looked me in the eyes. "Well, then, who's Lisa?" I looked down. Could not speak. Her eyes widened. "Was it you? Were you wearing my clothes... Lisa?" I couldn't stand the guilt, broke down in tears and confessed all. She was angry at first. She felt violated, and I couldn't blame her. She made me show her which panties and bras I'd worn. She took them out of the drawer and tossed them on the bed, telling me they were mine now, she'd never wear them again. She asked which dresses I'd worn. I lied, not wanting to admit I'd tried on most of them, and pointed to just one dress, the aqua and mint floral dance dress. "That's the only one you wore? Really?" She cocked an eye at me. "It was the first one I tried," I said, which was true. "It fit so nicely that I didn't bother with any of the others." Which was not true. "Well, it's yours now. The next time you want to dress up, come on over." She laughed, the last thing I expected at the moment. "Why not? Before I let you go home, Logan, I want to see you all dressed up as Lisa. What else did you wear with the dress? A slip? A petticoat? It's a swing skirt, it needs a petticoat. Here." She pulled the white nylon petticoat out of the closet and tossed it on the bed along with the other lingerie. "Okay, put on your pretty new underwear," she said. "Then I'll do your makeup, and then you can put on the dress." "I'm not going to put this stuff on!" "Why not? You did it when I wasn't here. Dirk said you looked lovely. Shall I invite your mother over for a fashion show?" "No!" "Well then, get dressed." "What, in here?" I said. "Why not? Real girls don't mind getting dressed around other girls." With a show of reluctance, I stripped off my boy's clothes and put on the stuff she'd tossed on the bed. The panties first, to cover my boy bits, and then the bra. She stuffed the cups with pantyhose from her hosiery drawer. "You should really wear a slip under the dress," she said. She pulled one out of another drawer. "Here, take this one, it's old and just slightly large on me. It's yours." She slid it down over my upstretched arms. "And now the petticoat." She held it open and I stepped into it. She pulled up the elastic waistband and stood back to examine me. "Oh, just look at you! Lovely Lisa, all dressed up in her pretties. No stockings for you until you shave your legs. Do any of my shoes fit you?" I pointed to the pair of sandals I'd been able to squeeze my feet into. "Come, sit." She patted the padded seat of her vanity stool. I sat, and she strapped my feet into the sandals. "I'll do your makeup." I was tempted to refuse, but realized that without her help, I would look even more ridiculous. I sat. In ten minutes, she made me look gorgeous. She picked up a hairbrush and hair dryer and fussed with my collar-length hair until it looked passably feminine. "Wow, you clean up nicely," she said. "Look, Ms. Underbust, I'm really sorry I touched your things, but can we stop now?" "No!" she said. "You didn't just touch my things, you put them on! If you like them so much, you can wear them for the rest of the day. Besides, I want to get to know Lisa better. Let's get your dress on. Hands up!" She tugged it down over my body and zipped it up the back. The bodice hugged me tightly and the skirt draped prettily over the petticoat. She had me swing my hips and swish my skirts around my knees. It felt wonderful, so right. I was thankful for the petticoat not just because it made me feel girly, but also because it hid the protuberance in my panties. She grinned. "Oh, you're so cute! Hang on." She disappeared for a minute and returned with a pretty little lace-trimmed hostess apron. She tied it around my waist, straightened the bow and adjusted my dress, and then stepped back, whipped her phone out of her purse and started taking pictures. "Hey! Stop that!" I said, trying to grab her phone. She shoved it back into her purse. "Too late! Now I have video! Pretty little Lisa, all dolled up and ready to do her housework! Or... maybe she's not a housewife, maybe she's a maid! All she needs is a black dress and a pretty cap. Which would you rather be, Lisa? A housewife or a maid?" "Neither," I said, wishing I could be either or both. I had mixed feelings about being a female servant, but I definitely liked the idea of dressing like one. I was such a disgrace to my sex. "Sorry, that's not an option," Ms. Underbust said. "Does your mother know you like to dress up?" "No," I said. What an idiot I was. Too late, I saw I'd totally set myself up for blackmail. I should have told her that yeah, my mom knows and she's cool with it. But if I'd said that, Ms. Underbust might mention it to her casually, just to check... I was trapped either way. "Why not?" she said. "Don't you think your mother should know her son likes to dress like a pretty housewife?" "No! Please don't tell her!" Ms. Underbust smiled. "Well, Lisa, maybe we can work out a deal here. The house looks fabulous. You obviously have good housekeeping skills. I'd love to have a live-in maid. Your mother said you're looking for a job. Okay, you're hired." "I don't want to be a maid, Ms. Underbust!" She got her cellphone out of her purse. "Let's see... 952-555-0123, right?" "Please don't call her! I'll... I'll..." She stabbed a finger at me. "You'll what? Accept my job offer? Minimum wage for forty hours a week, no overtime, though you'll be on call 24/7. Room and board and a clothing allowance. Well, not so much an allowance, I'll just give you lots of pretty clothes, starting with the outfit you're wearing now." "I can't be a maid, Ms. Underbust! That's a girl's job!" "I don't see the problem," she said. "You look like a girl to me. Girls can do boys' jobs, you know, and boys can do girls' jobs. I don't care what you have in your panties, as long as you keep it hidden." "What about your boyfriend Dirk? Won't he mind?" "Why should he? He's already met you and he thinks you're a cute chick. Just don't give him any reason to think otherwise - he doesn't like it when people deceive him." "He kissed me when I told him not to!" "That doesn't sound like Dirk. You must have flirted with him." I gulped. How could I get out of this situation? "Look, Lisa, here's what I'll do," Ms. Underbust said. "I'll call your mother. I won't tell her you're going to be my transvestite maid... oh, this will be so much fun! Instead, I'll tell her that you did such a great job as a house sitter that I've offered you a fulltime job as... hmm... a marketing events assistant. Ha! A booth babe. Your new job's in downtown Minneapolis, so to save commute time, my company will put you up in an apartment it happens to own there, at no cost to you." "I'll be living downtown?" "No, no, silly, you'll be living here with me. The downtown apartment is just a story we'll tell your mother. Be sure you tell her the same story. So, do you accept the job?" "As a marketing events assistant?" She rolled her eyes. "No! As a maid. If you want, you can think of it as a very personal assistant... to me. You'll do your assisting here at home, wearing a pretty maid's uniform fluffed out with petticoats and an apron and stockings and garters and a maid's cap. Oh, yes! How does that sound, Lisa? You had fun while I was away, didn't you? You liked wearing my clothes, didn't you? Well, now you'll get to wear even prettier and sexier outfits! And the best thing is, I won't tell your mother what a bad girl you were while I was away. Oh, and I won't tell Dirk that you're a boy. That's my job offer. Do you accept?" She had me trapped six ways from next Tuesday. I had no choice. "Yes, Ms. Underbust." "Yes, what?" "Yes, I accept the job." I felt a strange mix of embarrassment, fear and pleasure, and was surprised to feel myself stiffening. "Call me ma'am." Did she have to rub it in? "Yes, ma'am, I accept the job." "Good! Now curtsy." "What?" "Don't you know how to curtsy, Lisa?" "Of course not!" I lied. I'd been practicing curtsies every day for a week, though certainly not with any intention of doing them for Ms. Underbust. "I'm not a girl!" "No, not yet, but you're my maid, and I want my maid to dress and behave like other maids. And maids curtsy whenever they enter or leave their mistress' presence, and when their mistress gives them instructions." Okay, I'd show her. I placed my right foot behind my left, grasped my dress and petticoat with my thumb and forefinger, splayed out my other fingers, lifted my skirts, lowered my eyes and bent my knees. It was an intensely humiliating gesture of subservience. I held the curtsy for a second, then straightened up and let my skirts fall. "Very good, Lisa. You'll be a natural as a maid." "Yes, ma'am." This was getting worse and worse. What should I do? What could I do? I didn't want to go home, certainly not dressed like this, and if I just ran out the door, I'd have some tricky explaining to do to whoever picked me up - the police or, if I was unlucky, someone who might want to misuse me. "Now then, Lisa, if you're to be my maid, you'll need uniforms and lots of other things. You and I are going to go shopping! I'll see if my salon can fit you in for an emergency makeover to make you look more like a girl, and then you can make your public debut as Lisa." "Oh, please, no! I can't go out in public dressed like this! Can't we just order clothes online?" "Oh, Lisa, I think you know enough about women's clothes to understand that the sizes are imaginary. You have to try things on to see if they fit. We are going out. You're working for me now, and I expect you to do as I say." In no time we were in her car on the way to the mall. I was so scared that I almost broke down again, but once we got there, I soon found that no one paid me any particular attention. I guess my outfit wasn't short or tight enough to attract the male gaze. One woman told me she liked my dress. I nervously thanked her and, as girls do, complimented her in return - on her necklace, I think. Ms. Underbust talked her salon into giving me an instant makeover, which relieved my concerns about my hair and makeup, and then the two of us did our bit to keep department stores in business by spending a shameful amount of her money on girly stuff for me. Panties, bras, slips, a tight girdle with removable garters, a garter belt and stockings, nightwear, shoes, cosmetics, a handbag and other accessories. I had my ears pierced with tiny heart-shaped gold studs, and got some modest gold hoops for when my ears healed and a tiny gold crucifix on a light chain around my neck. No dresses or separates, though. For those, we made a separate stop at a uniform store, where Ms. Underbust picked out three maid's uniforms and accessories for me. The dresses were tasteful as maid's uniforms go - not silly French maid's costumes, but tea-length black cotton frocks with fitted bodices, full skirts, long sleeves and white collars and cuffs. She also bought me a set of petticoats of varying fullness, all the same length as the dresses, and half a dozen aprons, some with bibs and ruffled straps and some waist aprons. Two ruffled maid's caps trimmed with lace. As for separates? Nada. No skirts, blouses or, God forbid, trousers. Only dresses. "I think we've covered your basic needs," Ms. Underbust said. We checked out, and I had to make my way back to the car carrying an embarrassing number of shopping bags that nearly filled the trunk. I marveled at the sheer amount of stuff I now needed as a girl, compared to what I'd needed as a boy. Of course, the maid's uniforms were fairly over the top in terms of female needs. I mean, who wore petticoats nowadays? Ms. Underbust let me listen in as she called my mother and told her about my new job in Minneapolis. Mom was delighted to hear the news. "So he'll be moving out at last?" she said. "With a fulltime job? Wonderful! What will he be doing in - marketing, was it?" "Marketing events assistant. I expect he'll handle the job beautifully," Ms. Underbust said. "He's in the next office, would you like to talk to him?" "I suppose so," my mother said. Ms. Underbust waited a minute and then handed me the phone. I understood immediately that this was a test. I could ask my mom for help and tell her to call the police because Ms. Underbust was making me wear a dress and be her servant. Or I could tell her the same story that Ms. Underbust did. I realized that if I asked for help, the best possible outcome would send me home to my mom in boys' clothes, and that wasn't the outcome I wanted. Mom was right. Time for me to move out and make my own way in the world. Even if my first job required me to dress as a maid. Mom wished me luck, and then Ms. Underbust took the phone and said I would stay with her tonight and she would bring me home tomorrow morning to pack whatever I wanted to take to my new apartment. Anything I left behind could be thrown away. Mom asked for my new address, and Ms. Underbust gave her a post office box number that she said was the apartment building. I learned later that it was actually Ms. Underbust's post office box. Twenty-four hours later, I'd moved into Ms. Underbust's fancy house with a view of the lake. She showed me what she wanted me to do, and I developed a weekly routine to get it all done. Cooking, cleaning up, doing the dishes, doing the laundry, dusting, vacuuming, changing linens, cleaning toilets, separating trash and recycling into the bins in the garage that the gardener took out to the curb every week. I did all the woman's work that a traditional housewife was expected to do... minus children, thank goodness. I imagined having to take care of a baby, nursing it, changing its diapers, dressing it, playing with it, carrying it around with me, getting up at night when it cried, all on top of the housework I did as a maid. Ugh! I spent my days in my maid's uniforms, with a petticoat under my dress and an apron over it, and got used to the feeling of hems swirling around the tops of my calves. Ms. Underbust and I got along more smoothly than my mom and I ever did, and I came to realize that even though I was just a maid, my life was better than it had been at home, and I was happier as a result. ~ ~ ~ Then, one morning, Dirk dropped by. It was the first time in a while. He'd been out of town on whatever his business was, and wanted to see his girlfriend. The doorbell rang. I went to answer it, wiping my wet hands on my apron. I checked myself in the mirror in the entry, fluffed my apron, straightened my cap and opened the door. There he was, all six foot two of him. I caught my breath. "Hi, is Tina here? Hey - wait a minute, aren't you Lisa?" I wanted to sink through the floor. "Yes, I'm Lisa. I work for Ms. Underbust now. She's not here at the moment, but she'll be back soon." "Wow, you look great! How do you like being a maid?" "It's a job," I said. "Can't complain about the commute - upstairs to downstairs." "Wish I could do that. Hey, could I have a beer?" It struck me as rather early for a beer, but I wasn't going to say no to Ms. Underbust's boyfriend, not unless he misbehaved again. "Yes. Please come in." I closed the door and went to the kitchen. He followed me, ogling my ass, and took a seat at the breakfast table. I served him a beer and remained standing, feet together and hands folded over my apron. He took a deep swig. "Thanks, Lisa. You know, you look a lot prettier now than the first time I saw you." I didn't want his compliments. "Just remember to keep your hands to yourself." "That outfit you're wearing is really cute." "It could be worse. At least it's not halfway up my thighs." "Wow, that would be awesome," he said. "Show me." "Show you what?" My nervous meter ticked upwards. "Halfway up your thighs. Just lift your dress. And whatever you've got on under it." "No, thank you." "Aw, c'mon, Lisa. I'm paying you a compliment. Hey, if you're Tina's maid, shouldn't you do what her guests tell you to do?" I sighed, plucked at my skirts and lifted them in front until they were almost but not quite halfway up my thighs. He could see the garters holding up my stockings. I felt so humiliated! Dirk eyed my legs and smiled. It was a weird and uncomfortable feeling, being checked out by a man. I dropped my skirts. "Hope you enjoyed the view." Dirk grinned. "Oh, I did. Come sit here." He slapped his left thigh. "No, thank you," I said. "I said come here, Lisa. Take a seat." He stopped grinning. "No. You can look all you like, but you can't touch." He stood, grabbed my arm and pulled me face down over his thighs. His free hand pulled up my skirts and yanked down my panties. "Stop!" I cried. "Let me up! Help!" "Lisa! Hush! Disobeying your superiors is a spanking offense." Before I could reply, he gave me a sharp, stinging swat. "Count them, Lisa." "No!" "I won't stop until you do," he said. The next spank landed. "Ow! One," I said. "Thank me after each one," he said. Another. I grimaced. "Two, thank you." "Lisa! Call me sir." Another. Ouch! "Three, thank you, sir." When I reached twenty, he stopped. My bottom was on fire. I was crying. I had eyeliner dripping down my cheeks. I probably looked like Zombie Maid. And - dammit! - I was stiff again. I didn't think he could feel me through the petticoats, dress and apron, but I was ashamed to react this way to being spanked. "Are you going to obey me now, Lisa?" he said. I didn't want to say yes. "What do you want me to do?" "I want you to sit on my lap, Lisa." "No, sir! I don't want you to touch me! You can't spank me! Let me up!" The front door opened and shut. Ms. Underbust walked straight into the kitchen and stopped short, taking in the tableau Dirk and I presented. I lay across his thighs in my maid's uniform, my face a mess, with my skirts pulled up over my back, my panties pulled down and my bottom bright pink. Dirk easily held me immobile with his left hand and was ready to swat me again. "What's all this?" Ms. Underbust asked. Dirk let me go. I quickly regained my feet, letting my skirts fall and pulling up my panties as I backed out of his reach. "Hi, Tina," Dirk said. "I had to discipline your new maid." Ms. Underbust frowned. "What for?" "Disobedience," Dirk said. "Disobedience is certainly very bad," she said. "How did she disobey you?" "I asked her to sit down, and she refused," Dirk said. "He wanted me to sit on his lap!" I said. "Hush, Lisa," Ms. Underbust said. "Did you ask her to sit on your lap, Dirk?" "Yes, I did," he said. "Politely?" "I didn't touch her until she refused." Ms. Underbust nodded. "Why wouldn't you sit on his lap, Lisa?" "I didn't want him to touch me, ma'am. He was ogling me and making me uncomfortable. He made me lift my skirts and expose my thighs." "How did he make you lift your skirts?" "He told me to." "He didn't force you? He didn't touch you until you refused?" "No, ma'am. But -" "That's enough, Lisa. Dirk is my guest - you should call him Mr. Steele. You should obey orders from my guests as long as they do no harm, and it wouldn't have harmed you to sit on his lap. You should be happy that he wants you to sit on his lap! If you thought his order was improper, you could have come to me afterwards and explained your concern, and if I thought your concern was justified, I would have discussed it with Mr. Steele. You should not have disobeyed him on your own. You're the maid, not the mistress." This was so unfair! I blinked back tears. "On the other hand," my mistress said, "I'm partly to blame. I didn't give you detailed instructions on how to behave to Mr. Steele. But it's mostly your fault." How could it be my fault that Mr. Steele kissed me and beat me? She didn't give me time to protest. "So, Lisa, I want you to face Mr. Steele. Curtsy, kneel before him, apologize very humbly for disobeying him, and promise never to do it again. If he accepts your apology, you may rise, thank him humbly and curtsy to him again. As you'll see, Dirk, Lisa makes a very pretty little curtsy." I wanted to slap Mr. Steele, but instead I obediently went through the humiliating little ritual of apology. "Mr. Steele, sir, I humbly apologize for disobeying you and I promise never to do it again." I curtsied. Damn! I was getting hard again. Dirk was grinning ear to ear. "Good girl, Lisa. I accept your apology. Now, come over and sit right here." He patted his thighs. I felt defeated. Ms. Underbust wouldn't defend me. "Yes, sir." I scooped my skirts under me to protect my bottom before settling myself on his muscular thighs. I felt something stiff trying to poke through his pants and my petticoats, right between my buttocks. I shifted in his lap, but that just made him stiffer. Ms. Underbust said she was going to tell me something important and I should listen carefully. I was having trouble concentrating, because Mr. Steele was very gently starting to hump my butt. Slowly at first, gradually speeding up, giving me feelings I'd never had before. Ms. Underbust was explaining that she and Mr. Steele were in love and would be getting married. To my surprise, I found myself responding to his pressure. It made me want to wriggle in his lap, make him press against me harder. Ms. Underbust said that when they got married, she wanted me to be one of her bridesmaids. She said I would just love the dress she'd picked out. It was pink, she said. My wiggling seemed to stimulate Mr. Steele. He positioned me at the spot on his lap where he could poke me more directly. Ms. Underbust said Dirk was going to move into her house and would share the master bedroom with her. I would sleep in the guest room, which she would redecorate as the maid's room. I began to writhe in Mr. Steele's lap. He was fully hard. I could feel him press against my rear entrance, outside an emptiness that somehow ached to be filled. Ms. Underbust said that as the household maid, I would serve and obey both of them, not just her. Just as she was my mistress, Mr. Steele was my master, and I was to call him that. Mr. Steele's rhythmic pulses were making me feel feminine, receptive, yielding... a sexy little maid in the hands of her big, strong master. Ms. Underbust said Dirk would expect me to provide personal services that she herself did not care to provide. He would be in charge of my punishments. He would... Dirk's hand stole under my skirts and tugged on my skimpy panties. I dutifully lifted my butt. He pulled them down my legs. I kicked them off. What Ms. Underbust was saying sounded really important, but I could no longer follow her words. I was lost in lust. "Oh, Liiiiisa," Dirk said. Breathing hard. Wriggling. Grinding. Feeling frantic. "Yes, master?" "Unzip me," he said. The End

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Jill was the sitter my wife and I had settled on, because she had experience working in a day care and was an early childhood major at the college where I taught. Of course, I would have hired her on looks alone; the chance to see her made Wednesdays when she sat for us wonderful. She was tall and slender, with youthful modest breasts and gentle curves. But she had long, full, lush red hair that perfectly offset her creamy, freckled complexion. And she had a way of moving, deliberate and...

Quickie Sex
4 years ago
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Emergency Sitter

I’d known Kristen for almost two years. Our nine year-old sons played soccer on the same team, so we spent many Saturday mornings alongside the field watching them run around after a white ball. We weren’t exactly “good friends”, but we talked every time we met, passed the time of day and consoled each other in our single parent status. My wife had left me for her rich boss and how her husband ran off with a girl from a trailer park. We always laughed about how there was a message in there,...

Straight Sex
2 years ago
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Anns sitter

Ann complained while her mother was on the phone, I don't need a sitter she argued. Her mother said, I don't care, you're not staying by yourself, and that's final.Hanging up the phone her mother told her to take her bath.While Ann was bathing she got ready for her date.Finishing her bath Ann put on her nightgown and clean panties.Coming out front, her mother was talking to Mary. She explained how she was. Mary smiled and sad no problem.Mary asked Ann what she liked doing. Movie and video...

4 years ago
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Sorority Sister Sissy Sitters

SORORITY SISTER SISSY SITTERS by Throne Kevin was very uneasy. He knew his wife Petra was going out for the evening and she had hinted at making some special arrangement to deal with him. What else could she do? After discovering his habit of dressing girly when she wasn't around, she had used it against him. Whenever he was home now he had to wear the most shameful outfits she could think of. For instance, at the moment, he had on a sleeveless gingham top, the halves of which tied...

2 years ago
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A show for an 18 yo teenage baby sitter

True story that happened about 10 years ago.... I copied this story from where I wrote it originally. I was responding to a story written by eekntake where she did something very similar that reminded me of this story. So if you see it twice, know it is me in both cases, if you don't believe me then take a look at the username in the comments field. Now on with the story:I had worked late a few years back, like almost all night. It was summer and the k**s were off from school. So when I got...

2 years ago
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The Baby Sitter

Alissa had been baby sitting for the Bentley's for about a year. She was a senior in college, and baby sat to earn spending money. Alissa was a pretty 23 year old, with sexy blue eyes and short blonde hair. Mrs. Bentley, and her husband Tom had called Alissa to babysit for them Saturday night, and told Alissa she could use the guest bedroom because they probably wouldn't be home till the wee hours of the morning. Around eleven Alissa decided to go to bed. Alissa couldn't get to sleep no matter...

3 years ago
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Housesitter

Last year while Tom and I were living in Myrtle Beach we had a house in a very nice neighborhood with many  good friends.  We lived on a circle at the end of a dead end street which eliminated through traffic and noise.  Directly across from us on the circle is where Jeff and Allison lived.  They were a couple just a few years younger then Tom and I and they had two children.   During the month of June Allison stopped over for morning coffee and asked me for a favor.  Her, Jeff and the kids...

2 years ago
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housesitter

this is a fiction ,,,,,, was late as i rolled into the driveway. looks dark as i make my way into the house. is a little light comeing from the tv in the liveing room as i get closer to it. as i walk in i have to let my eyes get used the the surroundings. there on the couch is my housesitter all alseep curled up on one end, i make my way over the the other end and sit down. i see that it was a porn on the tv as i can see its cover laying on the floor in front of lisa my housesitter. beside...

3 years ago
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Housesitter

Last year while Tom and I were living in Myrtle Beach we had a house in a very nice neighborhood with many  good friends.  We lived on a circle at the end of a dead end street which eliminated through traffic and noise.  Directly across from us on the circle is where Jeff and Allison lived.  They were a couple just a few years younger then Tom and I and they had two children. During the month of June Allison stopped over for morning coffee and asked me for a favor.  Her, Jeff and the kids were...

Straight Sex
2 years ago
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Sarah our young babysitter

This story is fantasy. I'm a white male in my 40s and my wife is a cute Asian in her late 40s. We have a great sex life and are swingers. Mostly we like MFM and small gangbangs, she is increadably horny and I love watching her with other men. My wife and I adopted a adolescent girl from an Asian country about a year ago. This cut back some on our partying but we still managed to play once or twice a month. When we do go out one of her friends has a 13 year old daughter that we hire to...

3 years ago
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Diary of A Face Sitter

I don't know whether its the feeling of power, the control, the naughtiness or the orgasms. It may just be all combined. Whichever it is, I know I have never loved my husband more for his wonderful ideas. It started off a simple sexual suggestion. My husband Liam asked me to sit on his face one time when we were playing around. I told him I really wasn't comfortable doing it. I was scared I may smother him and for some odd reason, I felt a bit self-conscious about it. Liam would ask time and...

Fetish
4 years ago
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The House Sitter

Stepping up to the closed door, I raised my fist and gave the hard wood three sharp raps, hoping the brisk knock was adequate to be heard above the blaring music. A few seconds passed before I raised my hand again to repeat my knock, when the door swung open. Before me stood Laura, smiling enthusiastically as she held a glass of wine in one hand as her other moved from the doorknob to rest on her hip in a blatant attempt to strike a provocative pose. "Hellooooo," she beamed, flashing...

3 years ago
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Lucy The Baby Sitter

Well back when I was 12 years old I started to notice and change in me. I would have a hard on in the morning but I didn’t no why. Also I could see that when I saw a pretty girl it would get up a little. I heard of this but I really didn’t pay attention to it. One day my mom’s friend came over to visit. Her name was Lucy. She was Puerto Rican but she looked like a white girl. She had dirty blonde hair that was down to her ass. Nice big tits and bright green eyes. Slim waist and a nice around...

4 years ago
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A Reluctant Baby Sitter

Aunt “Lisa” was 38 at the time. She was a full figured woman at about 5’-8” tall. Her tits were 38 or 40, C-cups that must have been augmented because they were very, very firm. I had seen her in t-shirts with no bra and those puppies pointed straight out. My cock nearly burst through my pants every time I saw that. I am pretty sure she knew I was ogling her tits. She had dark red hair that hung down even with her shoulders and eyes that were a dark, deep color that seemed to change as the...

4 years ago
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Emergency Sitter

I’d known Kristen for almost two years. Our nine year-old sons played soccer on the same team, so we spent many Saturday mornings alongside the field watching them run around after a white ball. We weren’t exactly “good friends”, but we talked every time we met, passed the time of day and consoled each other in our single parent status. My wife had left me for her rich boss and how her husband ran off with a girl from a trailer park. We always laughed about how there was a message in there,...

2 years ago
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  • 19
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The House Sitter

I could hear the faint sound of music emanating from behind the door as I made my way down the hallway.   Each step brought me closer as the music became louder and louder.   I listened intently as I closed in, but could not make out place the song or the band, writing it off as one of the many independent, no-name artists that Laura always listened to.   Stepping up to the closed door, I raised my fist and gave the hard wood three sharp raps, hoping the brisk knock was adequate to be heard...

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