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CAUGHT! By Sissy Maid Sapphire I was returning home from work after a long, tedious week. I was walking up to the house hoping that my roommate Amy was out for the night. I was planning on a relaxing evening, lounging around in some of my favorite women's lingerie, sipping some wine, and reading through some of my favorite sexy TV magazines! The image of that was instantly shattered when I stepped into the house and saw that Amy was seated at the dining room table, reading something. That wasn't so unusual, but what she was wearing was! She wore a ruffled, white blouse, short leather skirt, black stockings and very tall patent leather shoes! As my eyes passed back up her, I could see garters holding her stockings up and her blouse was opened low enough to show an amazing amount of cleavage above a lacy black bra! I had always thought she was pretty, but now she was like someone right out of my deepest fantasies! "Um... wow! That's kind of a new look for you, isn't it?" "Well, yes. I think it's appropriate for tonight. Have a seat, I think you and I have some things to discuss." I was puzzled by her comment, but set my briefcase down and walked toward the dining room and stopped short. Laid out on the table was my collection of erotic magazines! They were a part of me that I kept hidden away, the part that loved women's clothes and kinky fantasies. Having them all spread out in front of someone else was a strange feeling, scary and exciting. It was also clear that she had been reading through some of them! As I sat down, I noted the one next to her seat was opened to a page depicting a TV maid being spanked by a Mistress. It was one of my favorite pictures and had fueled quite a few fantasies for me! Suddenly, I felt like my soul had been bared! I sat down slowly and heard the click of her heels on the floor as she walked behind me. "So it seems you have a side to yourself that I've been unaware of! A rather intriguing side, I might add!" She reached past me to the magazine she had been reading and slid it in front of me. As she did, I felt her breasts on my shoulder and found myself getting goosebumps! The whole room had an electrical tension to it that was making me short of breath! "That is a very sexy, photo. Do you like it?" "Yes, it's really intense, um... one of my favorites in fact!" "Mine too! I found it quite nice to look at it while imagining your reaction to it. I think I'm safe in assuming you wish you were that maid, don't you?" "...Um yes." "And by the way, do you own a dress like that?" "Uh no! I've never, I mean..." Completely flustered, I stuttered a bit more until she silenced me with a finger on my lips. She then moved her hand to the back of my head and began slowly running her hand along the nape of my neck. It was such a tender touch I almost felt like I was going to purr! "That's a pity. You do own some women's clothing, though, don't you?" "Yes, some stuff... mostly underwear and some shoes." "So do you sleep in lingerie sometimes?" "Yes. Almost every night, actually." "That's lovely. So do you have a girl name you like?" "Yes, I like to be called Annabelle." "Nice... such a pretty name. So listen I am going to open a bottle of wine. You, go get out of those work clothes and put something appropriate on that you can model for me. I want to meet Annabelle properly!" She walked into the kitchen, but I was too stunned to move. After a few moments she peeked around the doorway and saw that I was still sitting there. "Well? I don't think you are going to accomplish much just sitting there, so get going! I have plenty of reading material to keep me entertained. I'll be in the living room, waiting for you. Don't make me wait too long though... Annabelle!" Her smile and the way she lingered on the name had an interesting effect on me. Suddenly I actually did want to dress up for her and finally share the side of me that I never dreamed would see daylight! As I walked to my room, I realized that Amy seemed as intrigued by what was happening as I was, which made the whole scene that much more alluring. I also realized that I was dangerously close to having some of my deepest fantasies come true! I peeled off my clothes and tossed them into the hamper and went through my dresser, picking out what to wear. I decided to go with an outfit that I had bought several months ago. It was a matching bra, panties, and garterbelt set in white that was all lace and frills and was currently my favorite lingerie to wear! After sliding into each piece and adjusting the straps so they were comfortable, I slipped into a pair of white seamed stockings and my only pair of high heels, strappy white sandals with about a 3- inch heel. I had been practicing walking in them a bit but tonight I felt so awkward I was afraid I'd fall on my face! I took a couple of deep breaths to calm myself down. After walking back and forth a few times, I decided to add some lacy ankle socks that I had gotten on Ebay. They added nice, pretty accents to my ankles! As a final touch, I slid a lacy babydoll nightie on and, after a few more breaths to calm myself down again I walked down what felt like the longest hallway in the world. Eventually, I stepped into the living room and saw that Amy was seated on the couch, flipping through another magazine, this one was a bit more hardcore s/m, which made me a bit nervous, but I realized I was at the point of no return now! I managed a small curtsy as she looked up and was gratified to hear her gasp and to see a big smile on her face as she saw me. She set her wine and magazine down and stood up and walked slowly towards me, her eyes fixed on mine the entire time. When she stood directly in front of me, I noticed that even in my heels, hers were tall enough that our eyes were at the same level. That thought actually made me smile! She reached out and caressed my cheek with the back of her hand. "Oh Annabelle, I had no idea what a pretty girl you were! I can see now why you never wear shorts, your smooth legs look absolutely yummy!" "Thank you Amy, I had never-" Once again she stopped me with a single finger to my lips. "I think we can dispense with the pleasantries and familiarity at this point! You are to address me as Mistress or Ma'am for the remainder of the night, perhaps much longer if I'm so inclined! Now I don't want you to say anything, but if you accept me as your Mistress, I want you to suck on my finger and make it sexy!" She removed her finger from my lips and turned it slowly until she was pointing her finger right at my mouth! I hesitated for a moment, realizing the enormity of what was happening to us. I swallowed, closed my eyes and leaned forward, taking her finger into my mouth! As I did, I felt her begin to slide it in and out of my mouth. "Open your eyes, Annabelle, I want to see you looking at your Mistress as you suck on me! And I want you to suck so I can see your cheeks moving, and make some noise too!" I opened my eyes and found that her pleasant smile was now looking absolutely predatory! I was blushing furiously as I slurped on her finger, but as I continued I realized that I was enjoying it! "Mmmmm... very nice! Earlier I was reading a VERY erotic story in one of your magazines! It seems that a popular reward for 'girls' like you is to have you suck on a big strap-on dildo! Would you like that??" I didn't respond for a moment but my eyes grew bigger as her words sank in. She chuckled a bit and slid a second finger between my lips and held the back of my head firmly with her other hand. The way she was holding and penetrating me was the most incredible thing I had ever experienced! "Let me rephrase that. If I had a strap-on and told you to suck it, you wouldn't dare refuse me, would you?" I shook my head slowly and her smile grew even brighter, if that was possible! I think it was that moment where her love of controlling me, and my desire to submit to her clicked into place. I realized that I would not refuse her anything! I think she felt the same way, her smile made her look like one who is in complete control. "Excellent, pet, enthusiasm can wait, it is obedience that I will want for now! I am looking forward to training you, my dear!" With that she released her grip on my head and slipped her fingers out of my mouth, trailing one down the front of my nightie. It rested on my bra for a moment before she pulled away from me. She stepped back from me with her arms on her hips. "That was very well done Annabelle, you have quite a talented mouth. Now turn around so I can see the rest of you!" I heard her humming contentedly to herself as I slowly turned for her. When I was facing away from her she had me lift the hem of my nightie up. I was so aroused I could barely think straight, and was almost in a daze as I followed her instructions. Occasionally she would touch me here or there, jarring me like a shock! Eventually, I heard her hum approvingly and felt her trace a finger down the small of my back! Her hand slid into my panties and rested on my butt! Then I felt a finger moving toward my ass, making me squirm! Her finger rested at the entry of my ass and moved back and forth making me even more wound up!! "Honey, I don't think you have any idea how many women would kill for such a sexy ass!" I was just moaning at that point. Her free hand grabbed a handful of my hair and pulled my head back She leaned closer to me and whispered in my ear. "Have you ever been fucked, Annabelle?" "No, Mistress! Never!" "Wrong answer! You are supposed to say 'No Mistress, but I am dreaming of the day YOU fuck me!' You don't use the word 'never' with me!" "I'm sorry Mistress, I'm just um..." "Untrained and very turned on?" I hesitated for a moment and turned to look at her as she released her grip on my hair. She was smiling again and I immediately calmed down a bit. It was clear that she knew how I felt and she also wanted me like this! In fact, it was uncanny how she was controlling me. "Yes Mistress, that is exactly how I feel. I want to know that whatever I'm doing is exactly what you want! I want to be trained to be perfect!" "Excellent answer Annabelle!!" With that, she held my shoulders, stood me up straight and gave me a big wet kiss on the lips! She then turned away and sat back on the couch, picking up her wineglass as she did. She then casually tossed a pillow onto the floor, and pointed towards it. I didn't need any prompting to kneel down, nor to take the shoe off of the offered foot and begin giving her a foot massage. After a couple of tentative squeezes, I pressed firmly into the ball of her foot. She sighed contentedly, so I continued and was rewarded with her dazzling smile again! "Well, there are some things that won't need too much training, I see! So, as I was reading through some of your wonderful magazines, I came up with some assignments for you! And of course, there will always be a carrot at the end of the stick for you! Please work on the other foot for a bit." I grabbed a pillow off the couch and set her foot on it, taking her other one in my hands and repeating my massage treatment. I was again rewarded with a bright smile and a contented sigh, before she continued. "First off, you are to go to the costume shop downtown and buy a maid's uniform. While you're there, buy a blonde wig as well. Once that is done, get some pink lipstick and some press on nails. Then you are to purchase a douche/enema bag and a small anal plug. I think the adult novelty store a couple blocks from here will have some. Have you got all of that so far?" I was staring at her with my mouth wide open, scarcely believing what she had just said! She giggled at my expression. "Cat got your tongue, sweetie? Never mind, I'll make sure you write it all down before I send you out on your errand run tomorrow." "Tomorrow, Mistress?" My voice sounded impossibly small. "Yes tomorrow! After you've served me breakfast, I'll assign you a time limit to get everything. Then I want you to be wearing all of your new things and ready for your inspection at noon. Once I am satisfied with your uniform and appearance, your training will begin! And know that I am REALLY looking forward to that!! For now, why don't you go to the kitchen and make up a plate of fruits, cheeses and such, I'm actually quite hungry." At that, I went into the kitchen, heels clicking on the linoleum as I went. I was actually looking forward to whatever Amy was coming up with and was humming a little song when she came in and watched me getting her food ready. "Listen to my sexy housewife singing to herself! You're really enjoying this, aren't you Annabelle? Serve it to me in the dining room when you're done." I brought the plate in and set it in front of her, I was about to sit down when she gestured toward a pillow on the floor. I knelt down and she rewarded me with a caress along the nape of my neck. As she snacked on her crackers, cheese and fruits, she would occasionally feed me something, sliding her fingers into my mouth. Her fingers would then linger, tracing lines across my lips. I felt so blissful and relaxed it almost jarred me when she stood and announced she was finished and that I should get the kitchen cleaned up. "On second thought, go and start a bath for me and take my wine into the bathroom as well. It will be nice to just soak for a bit. And it will give me time to think up some sexy torments for my new servant!" I added some bath salts and set the wine on the edge of the tub. I also got some clean towels and set them out. Once the tub was filled, I came out and found Amy sitting on the edge of her bed. I curtsied and announced that her bath was ready. "Thank you Annabelle, you may undress me now! Do it slowly, though!" With that she stood and I started unbuttoning her blouse. She commented on my shaking hands as I undid the last one and slid the blouse off of her. "You like?" She teased while striking a bit of a pose. "Yes ma'am. You are one of the most beautiful women I've ever seen!" I was rewarded with a big smile for that! Once she was completely undressed she put her arms around my neck and gave me an incredible kiss! "Well girl, here's something for you to think about. I'm planning to work you fairly hard tomorrow, but you remember what I said about having a carrot on my stick?" "Yes Mistress, although I don't know exactly what you mean. I do know the concept." "Well, if you work hard and try to be the best maid you can, dedicating all your time and attention to my happiness, then you can move up to the next level... as my girlfriend and lover!" I gasped out loud at that! I never dreamed that Amy would be anything but a dominant to me! "Let's keep a few things straight, though. Don't forget that as far as the two of us are concerned, you are Annabelle from now on! Regardless of our public side, when we get home you will dress appropriately and BE my slave girl! And you will need to earn your way into my bed every night! And most importantly, as your owner, I have the cock in this relationship! You are the panty-wearing servant! So whatever you're doing around the house, you better be cleaned out and lubed, or you may find yourself very uncomfortable when I bend you over and fuck you!" Once again I found myself rather dumfounded by the way that Amy was changing! And the way she handled me was like she went from novice to professional dominant in one afternoon. As intriguing as this all was, her ease in controlling me was actually a bit disturbing. "Now go clean up the kitchen and when you're done, come back here with some paper and a pencil so we can go over your assignments for tomorrow. Oh, and bring the wine bottle with you. And you may have a glass as well." "Thank you ma'am, I'll be right back!" I turned to head to the kitchen when she stopped me. "Annabelle, you are to properly curtsy for me when I assign you a task, is that clear?" "Yes ma'am" I held the hem of my nightie and gracefully as I could dip down in what I thought was a nice curtsy. Amy, however, said we would work on teaching me a proper curtsy later. So I went to the kitchen and cleaned it up, which was actually pretty easy. I still found my thoughts were kind of confused. 'Where did Amy figure all this out?' and similar thoughts swam through my mind as I finished up and a bit later headed down the hallway with the wine, paper and a pen. She recounted the list she gave earlier and I wrote down each item. Suddenly her expression changed and she looked up at me. "What's on your mind, girl? I don't want to see any furrowed brows on my servant's first day!" "Well, Mistress, I guess I'm a bit confused about how you have done all of this in one day. It just seems weird that we would be roommates for over a year and I didn't suspect anything. It also seems strange that you could be so accepting and so...good at it! The way you've been with me feels almost too right and it's kind of knocking me for a loop. Sorry" "You're one to talk, honey! But think I understand what your concern is, but I'll fill you in on a couple of details that will answer all your questions. For starters, I've known about your little magazine collection for almost three months! It was that night we went out with your coworkers to that sushi place. You had my driver's license in your wallet and I snuck in and got it the next morning. You were out like a light from all that sake and... had three of your magazine's out on your bed!" "You've known for that long! Why did you wait until now?" "Well, I nearly moved out at that point! I was so shocked that my roommate, who I've had a bit of a crush on by the way, was immersed in such unusual erotica! Instead I did a little research and found a group called "Roses and Thorns" in town. They are a local fetish group and through them I met a woman named Karen. She not only knew what I was going through, she had been in the same situation. That was with her husband Charlie, nearly five years ago! Since then, 'Charlene' has blossomed into a very fetching, loving, and obedient servant and maid. Once I saw them together, I realized the possibility of doing the same to you! So since then, Karen has been teaching me how to handle and train slaves like you! A bit of a crash course in domination! And I've made a couple of very interesting discoveries about myself along the way." "Such as?" "Annabelle, you WILL address me properly from now on. And I won't warn you about that again! Anyway, the first is that I really, really love giving spankings! I practically came the first time I had Charlene across my lap for a punishment spanking. The other is that with a particular sex toy Karen bought me, a special double-ended dildo, I have unbelievable orgasms! Charlene was able to make me come with her mouth and ass so hard I was practically screaming! That made the final pieces fall into place." "I don't know what you mean, ma'am. What 'pieces'?" "Well darling, I guess it's safe to tell you that I really like you. I used to envision us as a couple and when I found out about your 'girl' desires, it made me angry and a bit disappointed. I just couldn't see how we would work sexually. However, Karen had me rewarding Charlene one day. She was in her maid's uniform, bent over the kitchen table while I fucked her from behind. I came rather quickly and within a couple of minutes, as my second orgasm was building I found I was imagining that Charlene was you! And that is exactly where we are going, dear! Starting tomorrow, you are going to be on the path to become my cock slave!" She stood up and asked me to dry her off. I grabbed one of the towels I'd gotten out and I began dabbing the water off her. She stepped out of the tub and gave me a kiss on the cheek. "Feel better, sweetie? I thought you'd like knowing I've been working on all of this for a couple of months and not just a few hours. It probably seems a bit more... professional! And for what it's worth, I've got some major plans for you and I!" "That is quite obvious, Mistress. So at this point, what would you like me to do?" "Well, first off, please get my blue nightie out of the bottom left dresser drawer. There are matching panties in the top left as well." I did so and helped her into it. It was an incredibly sexy little babydoll that barely reached her hips! Then I buckled a pair of high-heeled sandals on her feet. She then grabbed a canvas bag and told me to follow her. She walked to my bedroom set the bag on the floor and told me to remove my panties and sit on the edge of the bed. She then pushed me onto my back and drew several scarves from her bag and began tying my feet and hands to the bed frame with them. Once I was spread-eagled, she leaned back and gave me a thorough once over, chuckling as she caressed me. "Well darling I want you to realize that you could probably free yourself as I didn't tie you up too tightly. I want to make sure you stay put and not do anything naughty tonight. But I want to talk to you about a few things before you sleep." She stood and set my alarm clock then sat back down and drew a couple of items out of her bag. One was a rubber glove that she put on her left hand. With the other she squirted something out of a tube into her gloved palm. It was apparently lube and quite cold! She wrapped her hand around my cock and began stroking slowly up and down. I had been quite seriously aroused for almost two hours and within seconds was writhing and moaning as she slid her hand up and down. "Such an excitable girl! I just love seeing you like this, all hot and bothered in your pretty lingerie! Now I want you to tell me what I've got in my hand here." She gave me a sensual squeeze, causing my body to twitch and I gasped out loud. "It's my cock, Mistress! And I'm so close...may I come please!!??!!" At that she released her grip from me. Immediately, my hips were bucking up, trying to find anything to make me come! I had never been this close without being able to orgasm! I pleaded with her but she just chuckled and waited for me to calm down a bit. "Sorry sweetie, I can see you are going to need quite a bit of training and education about what's what and who's who. And we'll be starting right now. Now you have to realize that a cock is what a man fucks his girlfriend or wife with. I guarantee that you will not be doing any fucking for a long, long time, if ever again!" She began slowly tracing up and down my shaft with one finger, I reacted instantly to her touch and was squirming around once again. "No Annabelle, you need to realize that you are in the role of a woman now. A woman with a very, very sexy clitoris! And more to the point, this clit may be part of you, but never forget that it belongs to your Mistress! Now lets try that again. What have I got here?" She began stroking me again. I had never felt such exquisite agony before!! I was gasping for breath as I tried to answer. "Its...a... clitoris, Mistress! It's mine, but belongs to you!! Oh Mistress, please!! I need to come so bad!!!" "Now you're on the right track! And that brings us to the most important rule of all! One that you are to never forget and that is that you are mine! And I mean heart and soul, from your head to your feet! And so from now on, you are to never, ever, under any circumstances, touch, fondle, caress or play with your clit unless I tell you to! And you damned well better NEVER orgasm without permission!! Do I make myself clear!" "Yes, of course Mistress! I will do what you tell me!" "I am very serious on this, Annabelle! You will see very shortly that the next few months are going to change you forever! You are going to be emerging from a cocoon like a butterfly, spreading your new, feminine wings and learning your place at my feet as a feminized slave. You will have no secrets from me! You will tell me all of your fantasies, dreams, desires and fears without exception or hesitation. So if you get a little frustrated someday and think you can sneak home for a little fun without me, I will find out! And there are things I can put on your clit that will make sexual arousal VERY painful! This clit of yours is the key. It will either be the source of the most delicious, drippy, orgasmic sex you've ever fantasized about or the center of punishment that will make you rue the day that you first put on panties! The choice is up to you!" "Yes Mistress, I'll be good, I promise! I don't want you angry or disappointed...really!" She leaned her head down and planted a soft kiss on the tip of my...clit and slid her free hand under my nightie and bra, squeezing my nipple firmly and giving it a twist. "Good girl! And of course, these sexy titties of yours are in for a lot of attention as well! And to keep you in a proper mood, starting tomorrow when you present yourself to me for inspection, you're also going to have a wet, slippery pussy for me to play with! You'll be plugged, of course. In fact you will be plugged a lot at first. As you stretch and can accommodate larger cocks and toys, you'll need plugs less and less. You will always need your enema bag and lube, though. And I plan to check on you a lot!" With that, she stood up and removed her glove, dropping it into my wastebasket. Then leaned down and kissed me on the forehead. "Pleasant dreams princess! Now I want you to get a good nights sleep so you can be a good servant for your Mistress!" "No Mistress please!! Don't leave me like this!!!" "Sorry doll, not tonight! If you're a good, sexy maidservant for me tomorrow you'll be coming like you've never imagined all night long!! Disappoint me and we'll spend another night like this and you'll have to sleep unsatisfied! Never forget that your submission and your dedication to my happiness and me are what will get you into my bed...and my panties for that matter! Of course mine will have a nice cock in them for you! Good night Annabelle!" She switched the light off and I heard her shoes clicking down the hallway to her room. I tested the scarves and she was right, they were loosely tied and I could have gotten out of them if I could. I didn't dare though. Resigned to what she had in mind, I tried to clear my mind and get some sleep. Quickly I realized that was going to be very difficult given the mental state I was in. I sighed... it was going to be a long night! THE END

Pansy

30.07.2020
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As with all my stories these are truthful recollections of things past, except for the ones which are fantasies (lol) - you choose which you think they are! Names are real in the hope that the people involved will read about themselves and get in touch, (except where because of reasons that should be obvious, it could cause the person to be put in an embarrassing situation)If you enjoy them please give them the thumbs up; if you really like them please comment and if you REALLY like them mail...