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HOUSE SITTER (Complete story) By Lisa Lovelace ~ ~ ~ Part 1 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. ~ ~ ~ Part 2 My petticoats rustled under my maid's uniform as I knelt before my new master and unzipped his trousers. "Well?" said Dirk. "Take it out." I groped in his pants and awkwardly pulled out his male equipment. "Well?" Dirk said. "C'mon, Lisa. Lick it. Kiss it. Suck it." I shot a glance at his girlfriend, Tina - Ms. Underbust to me. She nodded. My name was Lisa now, but I used to be a boy named Logan. Ms. Underbust hired me as a house sitter while she was out of town, and found out afterwards that I'd been wearing her clothing. She made me dress up for her, said I was too pretty to be a boy, renamed me and blackmailed me into becoming her maid. I'd been serving her for three weeks now. Oh, I could easily walk out the door and be free - but for how long? I had no money or identification, and I'd be wearing a maid's uniform, unless I stole one of Ms. Underbust's dresses. I wondered how far I'd get before getting picked up - either by the cops, or by a male predator prowling the streets in search of lost souls like me. I could always return to my mom's house in Edina. It was only a few miles outside of Minneapolis - I could walk there, though it'd be an agonizing trek in my heels. But Mom didn't want me around now that I'd finished high school, and she didn't know I liked girls' clothes... so I could just guess how she would react if Ms. Underbust dropped me off at home in one of my maid's uniforms. It would not be good. Mom would probably tell me to get right back in that car and beg Ms. Underbust to keep me. So I didn't even try to escape from Ms. Underbust's house. I wasn't a man. I was a coward, a wimp, a sissy. Which is why I was now on my knees in front of Dirk, or Mr. Steele, as I'd been told to call him. He clearly expected me to give him a blowjob. I'd never received one, and for sure had never given one before. Ms. Underbust's sardonic smile told me she was amused by my situation. I couldn't expect her to rescue me. I grasped the base of his cock, which was several inches longer than mine, and tentatively licked the tip. It was warm. "Kiss it, Lisa," Ms. Underbust said. I did, and saw that I'd left a lipstick print on the head of his tool. My tiny sissy revenge on the big strong man. "Suck it, girl," Mr. Steele said. I did. I sucked it and licked it and kissed it and rubbed my hand up and down its saliva-coated length, and in a few minutes I was rewarded, if that's the right word, with a load of his ejaculate in my mouth. I swallowed the gooey mess, licked him clean and tucked him back into his tighty whities. I was painfully erect myself, but the bulge was hidden in my panties and petticoats. "Thank you, Lisa," Ms. Underbust said. I knew she didn't like giving Dirk blowjobs. That was my job now. "Well done." Mr. Steele patted me on the head, as if I were his little pet. "Get me another beer, Lisa," he said. ~ ~ ~ Later, I pulled Ms. Underbust aside and told her I wanted to quit my job. "Don't be ridiculous," she said. "It's hardly unusual for a girl to give a guy a blowjob. I was surprised you hadn't before." "I'm not a girl, ma'am!" She sighed. "Must we go through this again, Lisa? Look at yourself. Absolutely everything about you screams girl. You're a sissy, a girl for all practical purposes. Even if you were a boy, it's not unusual for one boy to give another boy a blowjob." "But I'm not gay, ma'am!" "It's not gay for a sissy to give a boy a blowjob. Sissies aren't gay or straight. They're sissies." Argh! I wasn't getting anywhere with her. I now understood what she meant when she'd told me my job would include giving Mr. Steele "personal services" that she didn't want to give him. I could only hope he wouldn't want this particular service very often. I lived in fear that Mr. Steele would find out I wasn't the teenage girl I appeared to be. Ms. Underbust had told me he didn't like being deceived, and my life now was one long deception. I asked her what I could do, and she ordered me a gaff, something like a thong panty that helped minimize male parts. She also advised me to avoid being alone with him and to threaten to tell her if he tried to go beyond the occasional blowjob. "You can't handle him, but I can," she said. I wasn't terribly reassured. I started wearing my gaff under my panties and an extra petticoat under my uniform, so as to conceal my secret under more rustling layers of fabric. My attempt to dress more securely went out the window one day when, as I was serving mojitos to my master and mistress on their back deck, Mr. Steele gave me a large wrapped package with a note: "For Maid Lisa, from her Master." "Open it," he said. I unfolded white tissue paper to reveal a black satin dress trimmed in white lace. Oh, God. It was a stereotypical French maid's costume. It looked well-made, not Halloween junk. Its skirt was extremely full and extremely short. I held it up against me and wondered if it would even cover my panties. Wearing it would be an exercise in humiliation. "Thank you, Mr. Steele," I said. Inside the box I also found a short, rustling taffeta petticoat half an inch longer than the skirt, a lace-trimmed satin apron that was pretty if not practical, and a pair of black satin panties with rows of ruffled white lace sewn onto the seat. My heart sank as I inspected the costume. It was fetish wear. I wondered how often my master would expect me to wear this instead of my regular uniform, whose skirts brushed the tops of my calves. "Put it on," he said. Oh God. I would look indecent. I picked up the costume pieces and started to leave the room. "No," Mr. Steele said. "Change here." I wanted to disobey him, but knew too well what would happen if I did. My bottom was still sore from my last spanking. I untied my apron, took off my regular dress and put on the French maid's dress. It weighed half of what my uniform dress did. I took off my regular petticoats, which preserved my modesty, and put on the new one, which did not - it just made my skirt stick out farther and cover less of my legs. I reached under the skirt and slid down my old panties, leaving the gaff in place, and pulled on the new panties. I used both hands to smooth the lace ruffles covering my bottom. I tugged on the new dress to try it make it longer, but it didn't help. It was scandalously short. If I bent over even slightly, anyone could see my panties. The white lace was impossible to miss. Ms. Underbust tied the delicate apron tightly around my waist, stood back and looked me over. "What do you think, Tina?" Mr. Steele asked. My mistress reached over and pulled off my mob cap. "Lose the cap," she said. "All she needs is a frilly hairband that she can make herself. It'll teach her how to sew." He nodded and turned to me. "What do you think, Lisa?" "Isn't it awfully short, Mr. Steele?" I said, swiveling my hips to make the skirt swish around me. "Master," he replied, looming over me. I hated having to call him that. "It's awfully short, master." "Makes it easier for you to bend over," he said with a smirk. "Oh, by the way. Anyone who sees the white lace on your panties is allowed to give you a little love tap. Not enough to hurt, just a little reminder that the lace on your butt is the sign of a slut. Put your hands on your knees." I bent to obey, knowing he could see the lace on my panties. He gave me a sharp little spank. "Ooh!" I cried, though it didn't really hurt. In a weird way, I kind of liked it. I wanted him to do it again. I straightened up and bent over again, and he swatted me again. I started to get hard in my panties. Oh my God, what was wrong with me? "See?" he said. "The lace on your butt is the sign of a slut." I straightened up, tried and failed again to pull my dress down, and turned to Ms. Underbust. "Mistress, what do you think? Is this dress too short? It doesn't hide my panties. I don't want people to think I'm a slut." She fluffed the hems of my dress and petticoat. "It is quite short," she said, "but not too short for a maid such as yourself. You need to learn how to move gracefully in a short skirt without exposing your most intimate underthings to men and giving them naughty ideas." "But, ma'am, won't I be exposing the lace on my panties every time I curtsy?" "Oh, I doubt it. Your skirt and petticoat are full enough that a curtsy shouldn't expose the seat of your panties. In any case, you didn't seem to mind getting those love taps from Dirk." That night, as I bent over the dishwasher to put in a plate, Mr. Steele came up behind me. "The lace on your butt is the sign of a slut," he said, and gave my bottom a swat. Sorry, a love tap. I stood up straight and froze. "So now what am I supposed to do, master? If I fill the dishwasher, I'll get a spank for every dish I put in it, and I'll never get anything done, and you'll waste all your time watching and spanking me." "Good point, Lisa," he said. "Tell you what, I'll spank you only once per task, not every time you expose your bottom during the task. That'll save me time and spare you a lot of spanks." "Thank you, master." I didn't feel very thankful, since the whole stupid "Lace on your butt" rule was his idea. He didn't limit himself to spanking. A few days later, as I climbed the stairs to change the linens in the master bedroom. Mr. Steele came up the stairs behind me, taking them two at a time, obviously in a hurry. I flattened myself against the wall, as Ms. Underbust had trained me to do when we met on the stairs. As he passed, Mr. Steele reached under my French maid's dress and petticoat and gave a hearty squeeze to both sides of my bottom. I started and gave a little shriek of surprise, but didn't dare to move or resist him. He sped up the stairs. "Sorry, Lisa, couldn't resist," he said over his shoulder before disappearing down the hallway. I stood unmoving on the stairs, angry at him and ashamed of myself. I was helpless against him, a helpless little sissy. I had good reason not to want his hands anywhere near my crotch, but after this incident, I knew it was inevitable that he'd grab me down there sooner or later, and would find something he didn't expect, and then - what? He'd probably beat the shit out of me. I told Ms. Underbust about the incident. She was more sympathetic than I expected and said she knew what I needed, though she wouldn't say what. She said she would order it immediately, but it might take a couple of weeks to arrive. For the next week, Mr. Steele limited my discipline to occasional swats when the lace on my panties showed, which was a relief, but he had unwelcome news for me. The Minnesota football team - the Vikings, he said - were playing their first game of the season on Sunday, and he'd invited three of his friends over to watch it. "And I want you to serve us drinks and snacks, Lisa," Mr. Steele said. "In your French maid's uniform. You must curtsy to them and call them sir. And remember, the lace on your butt is the sign of a slut. Make sure they see it, and I'll tell them the rule." I curtsied. "Yes, master." I was doomed. This had the potential of being really bad. Me in the same room as four males who would spend the afternoon drinking beer and feeling macho. I hoped Ms. Underbust would stay to act as a brake on the males' behavior, but as far as I knew, she didn't give a damn about football, and I feared I'd be left on my own to protect my virtue... or at least protect my crotch against close inspection. On Friday before the game, a large package arrived for Ms. Underbust. She opened it in her room and called me in. "Yes, ma'am?" Curtsy. "I have a present for you. It won't delight you, but it will protect you." "Thank you, ma'am." I looked in the box and saw a device made of stainless steel and various synthetics. I picked it up and turned it over in my hands until I figured out what it was: a female chastity belt. I gave my mistress a perplexed look. "I can't wear this, ma'am. It's made for a female body." "Maybe you're womanly enough to wear it," she said. "Try it on." I took off my clothes, and she helped me into the belt, telling me the device had been adjusted to fit a male form. The shield protecting the wearer's pussy was cunningly made so that a man's penis - a small penis, like mine - could be hidden underneath, if the man's testes were tucked back into his body. I could wear this belt instead of a gaff and look like a woman under my clothes, even if I lost my panties. I wondered what Mr. Steele would do to me if he discovered the chastity belt. Well, if it successfully hid my boy bits, at least he wouldn't tear me apart for being a boy instead of a girl. Ironically, I was wearing the chastity belt to protect a pussy that I didn't have. "It fits you perfectly," Ms. Underbust said. "Your body is getting girlier." "Yes, ma'am," I said, disliking the thought of having to wear the thing. It shamed me that I could fit into a female chastity belt. The thought made me stiff, to my further shame, and I discovered that the belt had room for my hidden penis to expand. I could probably even ejaculate in it, though it'd make a mess. "I'm not going to tell Dirk you're locked up. Maybe he'll find it, maybe he won't. If he does, blame it on me," she said. "I want you to wear it whenever Dirk is here, because I don't trust him to leave you alone. It's your fault, Lisa! You're just too tempting. That's why I'm not giving him a key. You can tell him that. If he hurts or threatens you in any way, tell me and I will deal with him." I blushed. "Yes, ma'am." Curtsy. Sunday came too soon. The game would start at noon. Like the big beefy players on the field, I started preparing for the game hours in advance, though in different ways. I was pretty sure they didn't take bubble baths to start their day. I doubt they moisturized their skin or patted it with perfumed powder or anointed it with scent. I doubt they shaved their legs and underarms, or depilated the rest of their body, or waited for three coats of nail polish to dry. I'm pretty sure they didn't spend as much time on their hair as I did, even though some of them had more than I do, and I know they didn't spend as much time on their makeup. That blotchy black cheekshadow the NFL uses is just not attractive. Oh, and I'm fairly certain they didn't wear lacy lingerie under their uniforms, which were definitely not French maid uniforms with extremely short skirts and four-inch black patent heels. I made a big pot of chili and put out chips, dips and a bucket of beers on ice for the boys, and retreated from the den and its big- screen TV to the relative safety of the kitchen. My mistress came down the stairs in a classic twin set over cashmere trousers. A lovely outfit, and I wished I could be wearing it right now instead my maid's uniform. "I'll be out for a few hours," she said cheerily. She twinkled her fingers at me and abandoned me to my fate. Mr. Steele - oh, hell, I'm going to call him Dirk, because he behaved like a jerk. His buds showed up shortly before game time, already well lubricated and ready to get more so. Dirk summoned me from the kitchen and introduced me to Wayne, Tyrone and Adam. I flounced up to each, bouncing my pigtails, and curtsied to him in turn. I needed above all to make Dirk and his friends believe I was a girl. I turned my hard- learned femininity up to eleven. This was essential to avoid exposure - but it had the predictable effect of making the boys more interested in their girly servant. I swished back and forth between the kitchen and the den, making sure they never ran low on beer or snacks, while spending as little time in their sight as possible, knowing that alcohol increased their chances of becoming frisky. At halftime, the boys informed me that the Vikings, who were in purple, were tied with the team in white, whoever they were, and the game was boring. Dirk took another long swig of beer. "Let's see if we can spice things up," he said. "Lisa, come here." I stood before him, heels touching, hands behind my back, eyes humbly lowered, hoping against hope he wasn't about to subject me to anything dreadful. "You're my maid, right?" he asked. His friends watched me instead of the TV, where talking heads were babbling statistics. "Yes, master," I said, knowing that's what he wanted me to say, and curtsied, knowing that's what he wanted me to do. "And you have to obey my orders, don't you?" "Yes, master," I said, dreading whatever would come next. "Well then, Lisa, I want you to give all my friends orgasms," he said. "Before the end of the game." I was stunned. He wanted me to get all these strangers' rocks off? How? And how was I to avoid exposure, with four men staring at me? I hoped my chastity belt would protect me, and reminded myself that Mr. Steele didn't know I was wearing it. I dropped to my knees, overcome by contradictory feelings of submission, fear and desire. "How, master?" I said. "You can blow them, or you can give them hand jobs, or you can let them fuck you," Dirk said. His friends voiced enthusiastic support for this plan. "It might be difficult to fuck me, master," I said, trying to look coy rather than defiant. "Why not, Lisa?" he demanded. "You have to find out, master," I said, curling a lock of my hair around my finger. He laughed. "Come here, Lisa," he said. I shuffled toward him on my knees. He patted his thighs. "Sit here." I'd already fought the battle of his lap and lost, so I dutifully scooped my skirts under me, sat and displayed myself as prettily as I could. I didn't know what Dirk was about to do, but I knew I needed to react the way a girl would. "Take off your panties, Lisa," Dirk commanded. If I did that, I would expose my female chastity belt. The moment of truth was at hand. "Yes, master." I clumsily pulled down my panties while sitting on his lap. The boys hooted and cheered. Dirk shoved his hand under my tragically short maid's uniform and groped at my crotch. "What the hell?" he said. With both hands, he lifted my skirt and petticoat and examined what he'd felt underneath. "It's a fucking chastity belt!" His friends guffawed. "Locked out!" Wayne said. "Denied!" Tyrone said. "Off limits!" Adam said. "Fuck! Tina must've done this!" Dirk said. "Well, guys, the offer is still good! I can personally testify that Lisa here can suck the brass off a doorknob, so get in line! She can do Wayne and Tyrone in the third quarter, and Adam in the fourth." "Not you?" Adam said. "I'll have her all to myself tonight," Dirk said. "Well, Lisa? Your master has given you orders." I did it. I knelt in front of the sofa and gave blowjobs to his friends. Master reminded me to look up into their eyes as I worked their cocks. They made me go slowly at first, but near the end, they grabbed my pigtails and face-fucked me until they came. I tried to turn off my brain, but could not help feeling waves of humiliation and submissiveness wash over me as I became a cocksucking sissy. I went to the bathroom, brushed my teeth, washed my hands and fixed my pigtail ribbons, and when I thought I could face the men again, I started tidying up. My scalp hurt. The game ended. Moments later, Ms. Underbust returned and breezed into the den. "How'd it go, boys?" she asked. I doubted she was asking about the game. "Did our maid provide proper service?" "Yes, she did, ma'am," Wayne said. "Even in her chastity belt." "Ah, you found it, did you?" she said. They laughed. "Dirk was sure surprised," Tyrone said. "She did a great job anyway," Adam said. "Well, I'm glad to hear she provided satisfaction," she said. "Did your team win? Aww, that's too bad." Dirk's buds all left shortly afterwards. I curtsied to each and gave him a kiss. They all fondled my boobs or butt. It was embarrassing, but I wanted the guys to like me, so that they would treat me nicely the next time they came to watch. When the last of the men left, Dirk turned to Tina. "What the fuck? A chastity belt? I had no idea! You embarrassed me in front of my friends!" "But it kept you and your friends from fucking Lisa, didn't it?" "Why does she matter so much to you? She's just the fucking maid!" "But she's not your maid for fucking, Dirk! You fuck me, you don't fuck her. That's why she's wearing that thing." "You don't trust me?" Mr. Steele said. "I do when you think with your brain," Ms. Underbust said. "I don't when you think with Mr. Big here." She ran her hand over the bulge in his trousers. Mr. Steele smiled. "Mr. Big is thinking as hard as he can right now." Ms. Underbust giggled. "Well, I'm right here in case he has any bright ideas." She started playing with him on the sofa. He told her to take it out. She refused. Said they had a maid to do that for him now. Told him she wanted him in bed instead. He followed her upstairs, practically drooling. Men were so pathetic. I cleaned up the den and kitchen while hearing them banging away in the master bedroom. I wished it was me, not Dirk, up there with Ms. Underbust. I wished I could have sex. I wished I didn't need to wear a female chastity belt to disguise myself as a woman. It was all because of Dirk. Dirk the Jerk. Dirk who was now my master, Dirk who could order me to do almost anything. Why did I put up with this? Because I was terrified by the thought of leaving with no money, no ID, nowhere to go, wearing a maid's uniform, locked in a woman's chastity belt. ~ ~ ~ Maybe he resented my chastity belt, or maybe he resented Ms. Underbust for not trusting him, but for whatever reason, Mr. Steele changed his attitude toward me. He made fun of me, bought me humiliating things to wear, treated me like a toy, played embarrassing games at my expense. I wasn't sure what he was up to. It made me feel even more powerless and ashamed. He started by making me wear a butt plug. A small one at first, then larger ones as the weeks passed. He changed his "Lace on your butt" game so that the winner could play with my plug instead of giving me a love tap. He would push it in a little deeper, or draw it in and out, or twist it inside me, or wiggle it back and forth. He told me to pretend the plug was giving me girly orgasms, so I had to moan and arch my back and call him master and beg him for more. It was utterly degrading. I wondered why he didn't fuck me in the ass. Maybe he just didn't like anal sex. I was glad - the butt plugs were painful enough. For a month, he made me leave off my dress, petticoat and slip every Nudie Monday and spend the day in just my corset, stockings, panties, apron and cap. He gave me swats or played with my plug whenever he liked, because the white lace on the seat of my panties was always visible. By now, all my panties were black satin with rows of white lace on the bottom. I spent a weekend made up as his kitten. I had to wear a headband with furry cat ears, eyeliner whiskers on my cheeks, black makeup on my nose, a rhinestone-studded collar and leash, and a black leotard and tights. He replaced my butt plug with one that had a kitty tail attached. He made me crawl everywhere on all fours. He wouldn't let me talk or use the toilet. Instead, I had to meow when I needed to go, and he would take me into the back yard on my leash and make me squat on bare dirt to do my business. I pooped only once that weekend, and he made me use my paws to scrape dirt over it, the way kitties do. On another weekend, he turned me into a baby. I had to wear adult diapers and plastic panties over my chastity belt, an adult-sized baby dress that didn't quite cover my diaper, and a baby bonnet that limited my vision. I had to crawl everywhere, like when I was a cat. I had to have a bottle of milk or a pacifier in my mouth at all times. I spent hours in the den forced to sit inside a real baby playpen, playing with a doll and watching infantile shows on TV. He watched me on a security camera to make sure I wasn't breaking any of his baby rules. I think he got off more on the idea of turning me into a baby than the reality of it. The breaking point came when Ms. Underbust refused to change my diapers, and Mr. Steele decided he didn't want to, either. I was out of diapers and back in panties before sundown. I thought I'd escaped from humiliation... But I hadn't. Instead of a baby, Mr. Steele turned me into a little girl. He dressed me in an adult-sized little girl's frilly pink party dress, with a Peter Pan collar, a bodice embroidered with flowers, puff sleeves, a filmy skirt that barely reached my thighs, and a wide pink sash that he tied in a bow behind my back. Under it I wore Disney Princess panties, a girl's camisole, and a scratchy net petticoat that rustled whenever I moved. Completing my little girl outfit were lacy ankle socks, Mary Jane shoes, pigtails tied with bright pink ribbons, and matching pink nail polish and lipstick. I looked - and felt - about six years old. My mistress and master spoke to me as if I was a little girl, making me call them Mommy and Daddy and using lots of cutie-pie words. Sometimes they told me to suck my thumb instead of talking. Sometimes they made me skip everywhere. I liked wearing the dress, but I hated pretending to be a six-year-old and couldn't wait to become my real age again. Unfortunately for me, Mr. Steele went through a bondage phase, my least favorite of all. For a month on Tuesdays and Thursdays, I wore padded cuffs and foot-long chains between my wrists and between my ankles, and another chain connecting the wrist and ankle chains, making it almost impossible for me to raise my arms above my shoulders. He buckled my rhinestone collar around my neck and attached my kitty leash to it so that he could lead me around the house. For a day, he made it a rule that I could move from room to room only if someone led me by my leash, but it was such a bother for him and Ms. Underbust to move me around for chores that he canceled the rule. When I wasn't working, he locked a chain from an eyebolt in my bedroom ceiling to my collar, a chain long enough to let me lie on the bed or crawl on the floor, but not long enough to reach the door. When he tired of chaining me up, he started making me wear girls' Halloween costumes instead of my maid's outfits. He liked me to dress up as a ballerina, in a leotard, tights, ballet slippers and a real tutu, with my hair up in a bun, and made me do lots of ballerina curtsies. From a costume rental shop, he brought home in turn a yellow satin princess dress with a tiara, a Cinderella dress with a huge blue skirt, a Scarlett O'Hara hoopskirt with a crinoline, a fairy dress in shades of green chiffon that fluttered like leaves in a forest breeze, and a Wonder Woman outfit with a bustier, short skirt, knee-high heeled boots and a tiara. It felt odd for Wonder Woman to be dutifully hand-washing her mistress' lingerie in Woolite and hanging it out to dry. Mr. Steele ordered me some Lolita outfits from Japan - incredibly frilly skirts and blouses with overskirts, aprons, and layers of petticoats, all in delicate, feminine fabrics trimmed with ruffles, pleats, embroidery, lace, ribbons and bows. The outfits included colorful stockings, platform shoes, and elaborate wigs, elaborate bonnets and hair jewelry. I felt more girly doing my chores in a Lolita dress than in any of my maid's uniforms. And then there was the wedding game. Ms. Underbust rented me a wedding gown with all the underpinnings for a weekend, and on Saturday afternoon, she escorted me to her salon, where she had them put my hair in a bridal updo and do my makeup. Back home, she pulled out a bunch of garment bags and made me put on wedding lingerie, bridal petticoats, a veil and a white A-line gown with a lace bodice embroidered with seed pearls. Mr. Steele put on a suit. Ms. Underbust wore a black skirt and white blouse and pretended to marry me to Dirk. She played the wedding march on her phone. I walked slowly across the living room to join Mr. Steele at a pretend altar. Ms. Underbust read an extremely abbreviated wedding service in which I promised to love, serve and obey him. We said our I do's, and she pronounced us master and sissy. He put a costume-jewelry ring on my finger, lifted my veil and kissed the bride. He picked up me and the gown with ease, he carried me upstairs to the master bedroom and dropped me on the bed. The skirt of the gown fell back, exposing my layers of petticoats. I was terrified, not knowing what he planned to do to me, but she rescued me by telling Mr. Steele that we needed to attend the wedding reception before there could be a wedding night. She led us back downstairs and poured us all flutes of champagne, and to my great relief, that was the end of the game. Ms. Underbust announced that I would be spared a "wedding night" with my mock husband, which gave the two of them another good laugh. As we waited for our favorite restaurant to deliver our dinner, I sipped my champagne and said as little as possible. The only part I'd enjoyed was putting on and wearing the wedding gown. I'd never worn one, absolutely loved the feeling, didn't want to take it off tonight and was sorry we had to return it. Like my Cinderella dress, it would have been completely impractical for housework, but in it I felt like a princess. The main problem with the wedding game - maybe the only problem - was the groom. I wondered what Ms. Underbust thought of the ways Mr. Steele was playing with me and the clothes he was making me wear. The cost wasn't an issue - she was well off, and I gathered his business was flourishing - but he was focusing so much of his attention on me instead of her that I wondered how healthy their relationship was. I managed to hint at this while talking with her one day, and she put me at my ease, sort of. "Oh, I don't mind," she said. "I mean, I think it's silly that he makes you go around wearing those ridiculous outfits, but if it doesn't bother you, it doesn't bother me." Actually, it did bother me - did she think I liked wearing diapers or chains? - but she went on. "He likes shiny new toys, and you're his shiny new toy at the moment. When he tires of playing with you, he'll start leaving you alone to do the housework, and I'll be ready and waiting for him." "But what he makes me do, it's just so embarrassing!" "Embarrassing? Says the boy who willingly wore lingerie and a maid's uniform to get his first job?" She had me there. "Yes, ma'am." Curtsy. I always worried about Mr. Steele discovering my boy bits, but he discovered my lack of girl bits instead. I was sitting on the sofa with him one day, feeling sexy but ridiculous to be wearing my Wonder Woman costume while watching Gal Gadot kick ass on TV. He had his arm around me, and after one particularly exciting fight sequence, he slipped his other hand into one of the gold-trimmed cups of my red bustier. "Eeek!" I shrieked in surprise. He usually left my breasts alone - they were unimpressive, more moobs than boobs, and he seemed to be a legs and butt man. I wasn't wearing a bra under the bustier, so he discovered my other secret right away. "Lisa! What the hell? Falsies?" I was so embarrassed. I should have worn a strapless bra under the bustier. "Yes, master.... I'm sorry... I don't have big breasts. Lots of girls like me wear them." He pulled my breast forms out of the cups. By now my mistress had bought me small silicone forms to replace the balled-up pantyhose I wore in my first bra. He set them aside and brushed my real nipple lightly. A thrill ran through my body, and my nip erected. It was small, but it was definitely upright. He flicked it with his finger. I gasped. "Does that feel good?" he asked. "Yes, master!" "Are your breasts still growing, or is that as big as they'll get?" he asked. "I don't know, master." "Would you like them to be bigger?" It all depended. Was I going to be a girl for the rest of my life? Or was my time as Ms. Underbust's maid just an aberration? Would I grow up and change back into boys' clothes and go to college and get a job and marry and start a family? That prospect felt way too normal, but... well, it was normal. If I accepted that I was a sissy maid and needed to look like one, there were big changes I needed to consider, and one of them was the state of my bosom. I needed to talk to Ms. Overbust about it. "Larger breasts would look better on a maid, as long as they didn't distract her master," I replied. That much was true. "I could give them to you," Dirk said. "A girl as pretty as you should have nicer tits." He played with my nipples. I sucked in my breath, felt my nerves vibrate with pleasure. "How...?" "I'd pay for you to have implants," he said. "They'd be quicker than hormones, right? What are you now, an A cup? You should have C cups at least, don't you think?" "I don't know, master," I said. I found myself unconsciously thrusting out my flat chest at him. I knew Ms. Underbust was a D cup and didn't want to compete with her, so C sounded perfect. "Aren't they very expensive?" "Don't worry about it. Real breasts will be even more fun for you than dressing up as my favorite female superhero." I wasn't too sure about that, but real breasts certainly would fill out my dresses better than breast forms, and the soft bras and slips and nightgowns I wore might feel delicious sliding over womanly nipples. Life would be better with breasts - if I remained a girl. Not so much if I ever wanted to be a boy again. I talked it over with Ms. Underbust. She said she'd been meaning to ask. She offered to pay for breast reduction surgery if I ever needed it, so I agreed to have implants. She asked me if there was anything I wanted to have removed, and I said no. My cock and balls weren't much use to me now, but I couldn't foresee the future. She scheduled the surgery and drove me to my appointments and consultations. On the morning of the procedure, she and Mr. Steele both came to the hospital with me. The operation was expected to last up to two hours, and if all went well, I'd be home by early afternoon with a brand-new bosom. I was lying on a gurney in my hospital gown with an IV in my arm when a doctor came to make a final check. "We're giving Lisa two C-cup breast implants, correct?" "Yes, doctor," Ms. Underbust said. "And we're not removing the testes or penis, correct?" Dirk's jaw dropped. "What?!" Ms. Underbust laid a firm hand on his forearm. "Not now, Dirk. Just wait and I'll explain. No, doctor, we're not." The doctor finished his check and said I'd be going into surgery in a few minutes. Dirk was staring at me, hard. He managed to keep his voice down. "Tina, what the hell's going on here? Is Lisa a boy or a girl?" "Lisa was born a boy, but she's all girl inside," my mistress said. "I found that out when I had her house-sit for me. She tried on all the clothes in my closet, and afterwards she agreed to become my maid, and as far as I know she hasn't worn boys' clothes since I took all of hers to Goodwill. Lisa is a pretty little sissy, small and weak, dainty and submissive. She's more feminine than most of the genetic girls I know, and cuter, too. I mean, she fooled you." "He did!" Dirk almost snarled. "All this time, both of you let me think he was a girl! You tricked me! I made him give my friends blowjobs! If they knew..." "Keep it down, Dirk. Lisa's sucked you off, too." "I know! Too gay! I wouldn't have done it if I knew he was a boy. What's his real name?" "Oh, Dirk, Lisa isn't a boy! She was born to wear panties and dresses. Just look at her!" "But he has a cock and balls, right?" Dirk said. "I mean, how can a boy wear a chastity belt for a girl?" "I had it adjusted," Ms. Underbust said. "Fortunately, Lisa has a slender waist and is, um, modestly equipped." "But..." The two of them shut up when a doctor and nurse arrived to wheel me into surgery. The doctor added medication to my IV and said I would fall asleep quickly. My last thought was that I was going to miss the rest of the conversation between my master and mistress. I'd expected Dirk to explode when he learned I had male parts, but he didn't, even though it obviously took him by complete surprise. When I woke up in recovery, they were both there, apparently at peace with each other. We were alone in the room. A nurse came in to check on me, told me I was doing great and left. "How are you feeling, Lisa?" Ms. Underbust asked. "My stomach's a little wonky, ma'am, but otherwise I'm okay. How do my breasts look?" "They're all covered up, but your figure looks much better, more feminine," she said. "Oh, and I have news!" She extended a limp left hand toward me. A diamond gleamed on her ring finger. "Oh!" I squealed. "Are you engaged?" "Yes!" "To Mr. Steele?" Stupid question, but I had to ask. They'd been starting a fight when I left. I guess she won. She rolled her eyes. "Of course!" "Congratulations!" I said the expected words, but had decidedly mixed feelings. I liked living with Ms. Underbust, but I could not say the same of Mr. Steele. "Did all this happen while I was in the operating room? Did he get down on one knee?" "Yes, I did," Mr. Steele said. "Before we go any further, I want to apologize." That would be a first. "For what, master?" "For the way I've treated you. Like a plaything and not a person. I'm sorry, Lisa." My jaw dropped open. I shut it. What a day of surprises! Since when did Dirk the Jerk realize I was a person? "Tina and I had a talk while you were in surgery," he said. "I would call it more of a come-to-Jesus meeting," Ms. Underbust said, tapping her foot. "Yes." Mr. Steele seemed subdued. "Well, she made me realize I was using you to avoid dealing with the big real-life decision I need to make. I played games like 'Lace on your butt' because they were less stressful and more fun than deciding to get married and settle down and, who knows, become a family man." Wow. These were the most self-aware thoughts I'd ever heard him express. I wondered what Ms. Underbust had told him to put him in this state of mind. Maybe he was speaking from his new orifice, the one she tore into him. He seemed softer spoken than earlier, maybe even slightly cowed. Well, I knew what my mistress was capable of, and frankly didn't mind if she had put the fear of the Goddess Tina into her man. I just wished I could have seen it. "Wow! What a lot to think about! What are you going to do, master?" I said. "I love Tina and I'm going to marry her," he said, "and we hope you'll be our housemaid." My mistress nodded. "And my bridesmaid," she said. "I'll show you the dress, it's pink and very girly. You'll love it!" I turned to Mr. Steele and searched my heart for the right words to say. "You treated me badly, master, and I didn't like it, but I accept your apology. All I ask is that from now on, please think of me as a person, not just a plaything." "Dirk needs to do more than that," my mistress said. "He needs to understand that you're a sissy. Not a girl, not a boy, but a sissy, a delightful combination of the best of both genders. You're not crude and violent like a man, and you're not bitchy and backbiting like a woman. You are a perfect servant and a lovely person who deserves to be treated with respect. I'm proud to have you as part of my household, and I hope you'll stay with me forever." "So do I," my master said. "Tina told me something that really got to me. She said that I was not treating you the way a gentleman should treat a faithful servant... regardless of whether she's a boy or a girl or a sissy. That stung. She was right. I'll do my best to be a gentleman from now on." I was so happy that I started to cry. "Thank you, master, thank you, mistress! Wow, I'm going to be a bridesmaid! Oh, and thank you so much for my boobs! Can we go home now?" The End

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THE SITTER

THE SITTER MOM AND DAD WERE LEAVING OUT OF STATE FOR THE WEEKEND TO ATTEND MOM'S sister'S WEDDING, AND THEY WERE LEAVING ME HOME, BUT NOT BY MYSELF. THEY HAD HIRED MISSY TO COME OVER AND KEEP AN EYE ON ME UNTIL THEY RETURNED. MISSY HAD BEEN MY FAVORITE SITTER FOR THE LAST 3 YEARS, AND I HAD DEVELOPED QUITE A CRUSH ON HER. AS SOON AS MOM AND DAD LEFT, MISSY WAS ON THE PHONE TALKING TO HER BOYFRIEND, MARK. AFTER WAITING OVER 10 MINUTES FOR THE CONVERSATION TO END, I GAVE UP AND TOLD HER THAT...

2 years ago
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The House Sitter

The House Sitter I don't want him taking care of our house when we go on vacation. I think he is snooping through my clothes and maybe even wearing them. You're overreacting Carol. John's an honest guy and wouldn't do that. Besides he is the only one we know that can do it. That's fine Tom, but if he goes through my things and wears them we will find out, and he will be sorry. Alright Carol I'll call him and remind him that we are going next week. I answered the...

3 years ago
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Emergency Sitter

Kristen needs a sitter... but the situation turns into a wonderful opportunityI’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...

4 years ago
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The House Sitter

My name is Donald and I'm a house sitter. It started off when I was in my teens and I baby sat for a few of my parent's friends and as I'm very conscientious and my Dad's senior partner needed someone to look after his house while he was on holiday, the whole thing grew from there. I'm 27 now and I house sit full time, supplementing my earnings with a spot of book reviewing. I'm not rich, but I have a comfortable living as I have virtually no overheads. Of all the grand houses I look...

3 years ago
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The Sitter Part 2

The Sitter, Part 2 By Cal Y. Pygia "Thank goodness you're here!" Sue Garrison cried. She'd been waiting for Becky Lewis to ring the doorbell for over twenty minutes. Seizing Becky's wrist, Sue hauled her best friend into the mansion's grand entrance hall, shoving the door closed with her foot. "Ouch!" Becky looked cross. She rubbed her wrist. Then, she smiled. "It's nice to see you, too, Sue. Where's the problem child?" "In his room," Sue replied. "At least, he was the...

3 years ago
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The Dog Sitter

The Dog Sitter   I was getting ready to go out of town for a week and my wife was going to be gone for three days towards the end of my trip. So we investigated a dog sitter company and engaged them to take care of our dogs for two nights.   About a week prior to the engagement Susan showed up, she was the one who was going to take care of our dogs. She was young, I would guess in her twenties, very busty and wearing a skirt that was almost see through, at least enough so...

Exhibitionism
1 year ago
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The babysitter

We hired a girl from the add we found at the supermarket looking for a baby-sitting job. We found she lives only a few doors away; very convenient. She said her name is Inna. She came to the house the first time for an interview and was dressed nicely and was very cute. We told her she could start this weekend as we were going out on Saturday. She agreed to be here at seven pm. Several weeks go by and she is doing a great job. She is prompt, the house is clean and the kids love her. She seems a...

Erotic
2 years ago
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Sissy Sister Sitters

SISSY SISTER SITTERS by Throne Claire and Rosa stopped as they approached the front door of the latter's house. They wore sexy outfits and a touch too much make-up, which was appropriate because they had been out clubbing. They looked at each other and began laughing spontaneously. "This is SO funny," Claire said. "I mean, us going out for the evening and leaving our husbands in the care of a sitter, like they were little boys." "You mean our SISSY husbands. And you should say...

4 years ago
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Bailey Our BabySitter and a Friend

Bailey was our very outgoing, vivacious, high energy, family baby-sitter. How I managed to survive after she headed off to her freshman college semester, is beyond me, but somehow, I managed to readjust. I was a little depressed the first several weeks, as Bailey had upended me, unlike anyone else I had ever known.When Bailey texted me that she was looking forward to being back home at the Christmas break, I became a little more upbeat about the upcoming holidays.Bailey and I had developed a...

Cheating
3 years ago
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The Baby Sitter

Now Robert I want you to know that I have decided on the girl who is going to baby sit you for a week while I go on vacation with my boyfriend James. You may remember her. Her name is Christine. She’s a fourteen year old. She was that little freckle faced red headed girl, who seemed to be enjoying herself with you so much during the tryouts last week. Remember how red faced you got when I told you to drop your pants and underwear and bend over and pull your cheeks apart to show her...

4 years ago
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An older male baby sitter

My mother and her girl friend were going shopping together. So we drove over to her place and mom left us to be baby sat by this womans husband. We were supposed to be going swimming later so my sister and me had on our bathing suits. We heard mom and her friend pull away in the car as we sat watching tv under the watchful eye of our unknown sitter. He was an average build not big at all but older, about in his 40s. We sat there watching tv together. I would look over once in a while to...

2 years ago
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Wife Hires Baby Sitter

My wife and I had been going through a long dry spell while she was pregnant to a few months after she had the baby. We would have sex occasionally during her pregnancy, but toward the end she said it was getting uncomfortable. The doctor had ordered no sex for at least six weeks after the baby was born. We tried having sex once after the six weeks was up, but again she said it was still a little painful. So the only action I was getting was watching porn late at night, and masturbating. I was...

3 years ago
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Seductive Sitter

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...

3 years ago
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Baby Sitter with Potential No 2

Introduction: Getting to know our baby sitter…..mmm Next Friday evening, Jack and Jane continue to use Tessa as their babysitter, Jack and Jane go out again,Tessa baby sitting …… on returning Jack insists he will attend to the boys while Jane takes Tessa home. Oh okay Jack…be back in a little while ( the girls are in deep conversation whilst Jane drives Tessa home). Jane you look gorgeous tonight … I love your ear rings(when the car stops, Tessa touches them and Janes ear – and notices Jane...

3 years ago
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More Secret Fun With House Sitter

I woke to the gentle sound of Linda's breathing a few inches from me in my parents' king-sized bed. My nakedness against the sheets heightened my awareness of my stiff dick underneath my body. I could feel her warmth radiating across the short distance between us. I'd never awakened next to a girl before. Katherine and I went down on each other in the basement, then usually just went back out to play. Waking up next to Linda after sex was a completely new and exciting experience.She was faced...

3 years ago
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Secret Fun With House Sitter

Linda's warmth wrapped around my bare skin as I slid close to her sleeping body under the covers of my parents' king sized bed. My dick was rock hard in my white briefs, the only thing I wore. Her red hair was tossled across the back of her tee-shirt as I rested on one elbow, inches from her. I took a moment to take in her pretty face, freckled from cheeks down her neck. She was a true ginger, and sexy as she could be. Given her reputation as an edgy girl, I was a little surprised my parents...

4 years ago
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The Topless House Sitter

The Topless House Sitter.I purchased a building plot in the spring. As summer arrives I decide that it’s time to do some minor repairs to the fences before I let the builders loose. I’m working up a sweat. Shirt off, topping up my tan on my firm mid-twenties body. I’m lost in the task in hand. Leaning on my spade I’m startled from my dreams as a voice asks, “Lemonade or beer?” Looking towards the voice I’m greeted by the sight of a beautiful almond shaped face framed with long brunette hair and...

4 years ago
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Rachel the Part time Baby Sitter

I saw an on line advertisement on social media where a neighbor was offering up her seventeen year old daughter to baby sit. As a single father with twin five year olds, I was thrilled to see the advertisement. Finally, I thought to myself, I can have a social life. A babysitter for the weekends when I had the kids would allow me a small amount of time to rebuild my life after a nasty divorce. Rachel was a cute and bubbly young lady. She came with her mother to check out my offer. As we sat at...

Seduction
2 years ago
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My kids baby sitter this is a legal age lady

This little cute thing used to baby sit my k**. Really a sweet girl. We developed a good relationship and she often talked with me, asked for advice and prolly just wanted someone to talk to. How could I refuse? She always did good by me, did great with my son and she's fucking gorgeous. I gave her a key to my house, she had my schedule and would just come over in the morning. If I was still sleeping she would come in and wake me up. I often sleep naked. She showed up and went in my room to...

3 years ago
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The babysitter

The phone was ringing. Brenna had just woken up and was dressed in only her bra and panties. Her 18th birthday was yesterday and she was completely exhausted. She picked up the phone."Hello?""Hi Brenna," it was Mrs. Brown, "I was wondering if you could come babysit my four-year-old girl, Katy, for a couple of days. Me and my husband are going on vacation and we need someone to watch Katy. I know two days is a lot to ask, but its summertime and we thought you could manage."Brenna sighed. It...

2 years ago
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Baby Sitter gets a Black Poker full

If you followed me to the prison from last time when I fell for Horny Black Bruno, then you will know how I got the prisons permission to see him. Yes I had to write and say I was his girlfriend in relations with him. This meant under new prison rules we could have private time with each other!I was aching to see him again and he said he needed my pussy to give him relief from his big spunk loads...haha a bit of him that could escape from prison in my nickers!Mmmm...so I had planned to go over...

2 years ago
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Baby Sitter Sex

My hubby Mick was very happy with spying on the young Baby Sitter at ours when he came back from the bar, leaving me and my Black stud there!Sue had come to our house with her boyfriend Jamile, I was surprised cause she was going out with a boy of her age before and he was so innocent! Mick had seen her wank off her 1st white boyfriend, but the new black lad older than her had pushed her further than he should. Yes he had filled her pussy with cum and Mick looking at them through the window had...

4 years ago
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Ava the Sitter

Ava Dominique and Elle Monique's mom had a close friend Diane had become an auntie some time back. Diane's younger brother Tommy was a father to identical twins boy and girl named Louis and Layla. Tommy, a few years older than Dominique always had a thing for her. He never acted on it but he could never keep his eyes off of her body. Even when he was in the 9th grade and she was in the 5th, he liked when she played wrestling with him. He loved pinning her down and putting her into submission...

4 years ago
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THE SITTER

My wife and I were going out for the evening and asked our neighbor, Paul, to baby-sit. Marny said she was driving so I sat in the passenger seat and settled in for a nice ride.Marny looked younger than her actual age, she was thirty eight but looked twenty nine, her body is as firm as ever due to a rigorous exercise program, and strict eating habits.Like I said, she's thirty eight, she's five feet seven inches tall, long jet black hair that falls to her gorgeous firm ass. Her tits are firm,...

4 years ago
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The Sitter

MOM!!, I’m 12 years old!! I don’t need a frickin baby sitter! Watch your mouth young man she said, I just don’t feel right going out of town for the night, and no one else is available. I saw her sign at the grocery store, called her, and she said she works at the Jehovas Witness temple, and is studying to be a pastor, so she sounded great, as sweet as could be. In about an our the doorbell rang, and I answered it, expecting an ugly b---h, and boy was I surprised. She was wearing a long, floor...

3 years ago
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The Sitter

MOM!!, I’m 12 years old!! I don’t need a frickin baby sitter! Watch your mouth young man she said, I just don’t feel right going out of town for the night, and no one else is available. I saw her sign at the grocery store, called her, and she said she works at the Jehovas Witness temple, and is studying to be a pastor, so she sounded great, as sweet as could be. In about an our the doorbell rang, and I answered it, expecting an ugly b---h, and boy was I surprised. She was wearing a long, floor...

4 years ago
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The Sitter

This is a work of fiction. More importantly, this is a work of erotic fiction. Even better, this is a work of erotic transvestite fiction. If you are under the legal age in your state, country or planet to obatain adult literature, STOP READING NOW! The Sitter by Sissy Demi It was Friday afternoon and I was on my way home. It was only a half day of school that day. Parent/Teacher conferences or some bullshit. Who cared I had another half day that I didn't have to be in that crummy...

2 years ago
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Baby Sitter

It was a cold and unforgiving night as Jennifer stumbled to her job. The streets were empty and the darkness clung to her like a wet t-shirt. She strained in the dark to read the house numbers as she rounded the bend to Alma close, it was unsettlingly silent, the wind that had once whipped up round her ankles died and everything was still, waiting. She stood at the front door anxious to enter, though she'd been here before on many a night she some how felt...

3 years ago
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Changing Channels The House Sitter

Changing Channels- The House Sitter By Zouscha I saw the notice posted on the bulletin board in the university center, and I pulled it off before anyone could beat me to the punch. The note said 'Housesitting- will pay $250 for one week' and it gave a number. Well, I was pretty cash-poor this semester, so I jumped at the chance. I got back to my dorm room and called right away. An airheaded voice came on the phone, and said yes, they were leaving tomorrow. They'd leave the keys under...

2 years ago
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Lou The Baby Sitter

This is the story of Lou My very Special Friend Missy's ( Wendy ) Babysitter...Its a weekend late summer , and I have a busy social programme over the next couple of weeks -- birthday parties weddings etc Charlie has arranged for our usual sitter Lou to look after our son while we are out -- in the past if we expected to be really late she just stayed over in the spare room.This particular Sat ,I was driving through the village when my attention is taken by this statuesque figure gliding along...

2 years ago
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Baby Sitter

BABY SITTER By Tammie Anne Freeman Chapter 1 Anna looked at the address written on the note card. She hadn't worked in this neighborhood before, and was concerned that she was going to be late. She worked for a babysitting agency that provided special services, and the clients could be very demanding. But thankfully the job tonight looked like a regular baby-sitting job, and she could probably be a few minutes late before the client called to complain to the...

3 years ago
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my baby sitter

I was home healing from leg surgery, sitting by the deck door, when my very sexy baby sitter tapped on the deck door.She was looking fine, wearing a pair of snug, low rise blue jeans short shorts, showing some nice cheek, PLUS a beautiful low cut tank top, showing off her well endowed cleavage. Falling out the side of the top, plus a well tanned belly button. She came in, with a smirk on her face and leaned very suggestively against the door.She teetered and giggled as she talked, and asked to...

3 years ago
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The Baby Sitter

We had planned this night out for some time, but as usual something always goes wrong. The baby sitter called & cancelled at the last minute. I suggested that my wife ask if Shelly, the 17 year old girl from next door could baby sit at short notice. She trotted off next door & came back to tell me that Shelly was not available but her 19 year old brother Joey Was. We really wanted to go out so she agreed to let him sit for us. He seemed like a fine young lad, he was very fit, he was a...

2 years ago
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The Sitter Part 3

The Sitter, Part 3 By Cal Y. Pygia "Wow!" Sue said, staring at Danielle. "I love what you've done with your hair, and your makeup is superb! And your dress is awesome!" Becky, who'd accompanied her friend to her babysitting charge's home, agreed, but she cautioned Sue not to give Danielle too much credit for her transformation from Daniel into the beautiful creature who stood before them, eyes cast down and hands clasped demurely in front of her. "She's come a long way, for...

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