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cuckoldress

by Lissagar

cuckoldress

Soon after we got married, I worked up the courage to nervously reveal my embarrassing fetish for dressing up in womens clothing. She was uninhibited sexually, we fucked every day. She was only 16, much younger than me, so I considered myself her superior being 21 , and she behaved as if I really was. I never let on that I was virtually a virgin when I met her, so subconsciously I looked to her as my first mistress from the start. Lisa! Yes mistress? I ordered you to wear your 5 “ heels and you ‘re still wearing your 4” pair, Why? ! Please mistress they are so tight and I can barely stand or walk in them. She stands in front of me and starts manipulate my tiny breasts, “Awww, What’s wrong sweetness? Is little sissy uncomfortable? You wanted to dress the part, so you must suffer like we women suffer, I’ll just lock them to your feet and you’ll get accustomed to them in no time, OK sweetie!” my cock is so hard it aches, then I remember the cage device she wickedly locked around my penis, seeing the pain on my face and hearing my moans, a smile spreads across her sadistic face.I own you as well as that thing between your lovely silken thighs! May I please be allowed to cumm tonight? Hmmm, I’ll think about it, but for now get over here and dry me off, I must get ready, Richard will be here soon! Mistress, please don’t leave me home alone again tonight, I, I could give you pleasure if you’d let me.. That’s sweet, but only real men can give me what I need, and you are becoming a girl, remember? Please, let be your husband again, I need to suck your toes and worship your precious pussy and massage your lovely body.. Quit dreaming and paint my toenails, Lisa! I am going to get fucked by a real man, he is so strong and handsome! Not a sissy bitch like you! "You like how I look sissy?" "Yes mistress, your very beautiful." She smiled, "You are too, you have nice slim figure considerably feminine, and a pretty face, not very muscular, and a real cute ass a very pretty boy. I think you look hot dressed in pretty lingerie, don't you sissy?"Shaken, nervous, a little demoralized I responded "Yes" "Yes mistress" "Now get down on your knees". I did as I was told. "Good boy". Mistress then grabbed my other ear and pulled on them both extremely hard, tears were coming to my eyes. She smiled down at me "You want to be a good boy don't you?" "YES MAAM" "Excellent, now listen very carefully as I am only going repeat these instructions once and I expect them to be done to the exact detail! When I give you permission to do so, I want you to go into the closet beside the bar and pick out a very pretty outfit that you think you would look cute dressed in, from bra and panties to stockings and heels, to a pretty dress and I want you to bring every item out and lay them on the couch. When your done, you are then to empty your pockets into the pretty purse you chose. Then take off all those disgusting clothes you have on now and put them in the garbage bag sitting on the coffee table. Then get down on your knees and crawl over to Monique and me sitting at the bar. Then look up into my eyes and ask very nicely `Please Mistress please permit me to begin to experience becoming your very very feminine houseboy'.... Now be a good boy and do as your told!!!" and she let go of my ears. "YES MAAM" Shaking and tears in my eyes I stood up and walk over and went into the closet. It was a very large closet with a huge selection of woman's fashions. Fearful of the strength Mistress had demonstrated over me, without help, I saw no way out. She was right, I was scared to try to stand up to her for fear she would really hurt me. I began looking threw drawers in the closet, feeling some bras and panties, and I found myself starting to get aroused. Seems silly.... How could I be excited about picking out a pretty feminine outfit I was going to be dressing in....I decided on a white satin bra and matching panty, with a white satin merrywidow and white seamed stockings. I sat them on the couch and went back and picked out a short white satin full slip, white open toed 4" heels that strapped around the ankles. I sat them by the couch and went back and began to l look through the dresses, I honestly seemed to be enjoying this.... I picked out a white dress with black pokka dots , the skirt part had two layers, and picked out a pair of white flower shaped earrings and a white leather purse. I sat them on the couch. I then emptied my pockets into the purse, stripped down and place my clothes into the garbage bag. I got down on my hands and knees and crawled over to Mistress and Monique. I looked up into Mistress's eyes...."Please Mistress pretty please permit me to begin to experience becoming your very very feminine obedient houseboy...." Mistress smiled, then stood up and slapped me across the face. "Ask me again" Still looking into her eyes `Please pretty please Mistress, permit to begin to experience becoming your very very very feminine obedient houseboy' Mistress smiled, then slapped me three more times very hard and grabbed both my ears, pinching them ... "ask me again" Tears started to drop from my eyes ... sharp pain from my ears.... But still looking into Mistress's eyes I whimpered `Please pretty pretty pretty please Mistress, permit to begin to experience becoming your very very very feminine obedient houseboy....' Mistress smiled, pinched my ears a little harder, "your not much of a man, I like that, I will be able to keep you in your place very easily. Now take a good look at your body and then tell me what you think you should do to make it look much more feminine for me.." , she let go of my ears. I look down at myself and I saw my hairy legs, no I thought I can't.... Then I looked up into Mistress's eyes `Please Mistress permit me to shave my legs and underarms so that I can look much more feminine for you.' Mistress smiled "Very good boy, the shower is through the door at the back of the closet you will find everything you need there and be a sweetheart and paint your toe nails a pretty color for me while your there, and do an excellent job, I don't like sloppiness. When you're done come back here for inspection. Understood!!!". "Yes Ma'am" , I got up and went to the shower. I removed all the hair from my legs with hair remover gel and shaved my underarms with a razor. I also removed the hair from my chest and toes. I then sat down on the toilet seat and began to do my toenails with bright red nail polish. It all seemed silly yet erotic. When I was done I went back to report to Mistress for inspection. When I reported back I stood still in front of Mistress at the bar awaiting inspection. Mistress stood up. Smiled. Walked around me several times. She then stood behind me and began feeling my legs. "Oh lisa your legs feel so nice and smooth and your toes, they look so pretty. You want to look very pretty for me don't you!!!" `Yes Ma'am' "Good boy, then go pick up the white panties you put on the couch and come back and get down on your knees, look me in the eye and ask permission to show me how feminine your ass looks dressed in a pair of pretty white panties....DO IT NOW" She startled me with the abrupt command, which made me hurry to retrieve the panties and get to my knees. I looked up at Mistress and into her eyes, `please Mistress, permit me to show you how feminine my ass looks dressed in these pretty white panties for you.' She laughed, slapped me hard four times across my face, pinched my ears, looked me in the eyes and pulling me by the ears upward towards her..."Do you think a man would ask a woman if he could show her how feminine his ass looked dressed in a pretty pair of white panties!!!!!!" ........ ` No Ma'am '.............. Pinching my ears harder ......."Then your not a man are you?" ........ `No Ma'am' ......... "Then what do you think you are?' ...... tears in my eyes I whimpered ` a weak sissyboy, Ma'am ' ....." She laughed and slapped me hard 2 more times across the face...."That's right a weak sissyboy......now put on those pretty white panties and show off your sissy ass to me". I slipped my legs into the panties, my arms shaking, and pulled them up around my waist. I turned around a couple of times in front of Mistress and wiggled my ass. "My my they do look so very pretty on you . She walked around behind me and felt my ass. Oh and your ass feels so nice in them. Now be a good sissy and go pickup your sexy white bra from the couch and then get on your knees and ask permission to show how feminine your chest looks dress in a pretty bra.... DO IT NOW" I jumped and fetched the white bra from the couch and crawled back on my hands and knees, I looked up into Denise's eyes ` please please Mistress permit to show you how feminine my chest looks dressed in a pretty white bra.' "Oh that's so sweet, such a good sissyboy, put the pretty bra on now" I wrapped in around my waist and hooked the eye enclosure together, and moved it around my waist to the back and slipped my arms through the straps, then adjusted the bra into place. I then stood still with my arms at my sides. "Very well done!! and it looks so pretty on you. Now pickup the merrywidow , nylons , high heels , slip and that beautiful dress. Then on your knees and ask permission to show me how very feminine you look dressed in them for me....DO IT NOW" I jumped again and retrieved the merrywidow , nylons , high heels , slip and dress. I got back down on my knees , looked up into her eyes , ` please pretty please Mistress, permit to show you how feminine I look dressed in this sexy merrywidow, how sexy my legs look dressed in these nylons and my feet in these shoes and how very very feminine I look dressed in this white satin slip and beautiful white dress.' "Terrific, is so nice to hear a weak boy ask permission to dress in pretty, feminine clothes. Go ahead my sweet sissy, put them on now" I wrapped the merrywidow around my waist and did up the hook and eye closures then moved it around my waist and slipped my arms through the straps. I then worked my finger and thumb down into the first nylon stocking and worked it up my leg and fastened the two straps and repeated with the left leg. Then I stepped into the slip and slipped my arms through the spaghetti straps, I put my arms in the short puffy sleeves of the dress and pulled down over my head, I adjusted the dress so it rested properly on me. I sat down slipped my right foot into the first heel and did up the strap around my ankle, I then slipped my left foot in the other heel and did up the strap around my ankle. I stood up a little uneasy in the 4" heels and stood still in front of Mistress. "Excellent..." Mistress walked around behind me. She began to feel my legs and whispered in my ear. " You have such nice slender feminine legs Bill and they feel so good dressed in my nylons." She squeezed the top of my right leg and felt my pantied ass under the dress, "you certainly don't feel like much of a man right now." She walked over and picked up the earrings and walked back and clipped them on my ears. She stepped back, looked me over.." very very pretty, now this is the way I prefer my boy to look and dress." She smiled. Walked around behind me again, began feeling my legs, and whispered in my ears " you like how it feels to be dressed real feminine don't you ..... ` Yes Ma'am' ....... " You want to learn to become more feminine don't you ?" ........ ` Yes Ma'am' ...... " You want to dress very feminine and look pretty for me all the time, don't you ?" ..... ` Yes Ma'am' ........ "Now, do you think a very feminine boy like you should be in charge in a relationship, or a very aggressive dominant woman like Me." .......... ` a woman like you Ma'am' ...... " Then show me .. walk the length of this room and back to me as feminine as you can in your beautiful dress, then do a pretty feminine curtsey , look me in the eye and tell me your a very very very weak feminine sissy , who never ever wants to act, look or dress like a man again. In fact you want to become my completely feminine sissy and begin to experience being totally dominate by ME" ....... " now show me" I began to walk the length of the room , tears in my eyes , the fear , the excitement I was feeling right now was becoming overwhelming.... I turned at the end of the room and began to sway as feminine as I could back towards Mistress. She was smiling , she knew inside I was going to belong to her, and when I stop in front of her and began a pretty curtsey in that very feminine white dress I knew as well I was hers. I looked into Mistress's eyes, ` Mistress, I am a very very very very weak feminine sissy , who never ever wants to act, look or dress like a man again. Please I want to become your completely feminine sissy and begin to experience being totally dominated by you ,Mistress please please....' and I began to cry. Mistress took me in her arms ... " its alright Lisa just let the tears flow out..... You're going to become the most beautiful sissy. You're going to wear the most sensuous lingerie and the most beautiful feminine dresses for me. And I know you will do exactly what your told, when your told, whereever your told because you want to be a very very good girl for me."

I think you would enjoy seeing us fuck, wouldn’t you ? No, Mistress. One of these nights, I’ll make you change your mind, you know that, right? Yes, Mistress. Lisa, if you make me late tonight, I’ll let Richard fuck that hairless ass, so get busy! Lovingly cradling her perfect foot in my hand, I begin painting each toe like I’ve done every weekend for the last 2 years . My pussyclit feels numb, and my balls are packed, but my chastity is locked and Mistress has the only key. Lisa! Help me with my bra, you know I love making you horny and you get so hot whenever I force you to put my silky bra on for me! Straiten the straps, there that’s much better! Sissy, are you looking at my breasts ? Yes, Mistress. That’s sweet,
Gracefully stepping into my shower, I’m taken with all these new sensations. My new breasts bounce and tug sensuously at my chest , and whenever I look down my eyes can see just how ample my bosom has become since my operation . 36c. My mistress settled on this size for one reason, there would be no way for me to conceal them thus I would have no choice but to become a ladylike as possible. This was also the reason she forced me to have my eye-liner and ruby red lip-liner permanently tattooed on. Pleased with the results she said it gave me a sensual whorelike image that I so richly deserved, she gave me a silver lipstick tube with Lisa, my new name, engraved on it. After a quick shower I step from the tub and stand before my full length mirror and towel off. Drying my long auburn locks with a towel, I wrap it around my head like most women do. I slip my silk dressing gown on and step up to my vanity . Begining with my lips, I lovingly apply my lipstick, filling in the lip-liner, I finish and pucker and pout at my reflection. Next I begin doing my eyeshadow, going for a dark sensual look. Whenever I do these simple tasks I get extremely aroused. I've seen real women do their make up for years and secretly longed to have them do mine, but now I can do it myself and it feels so good. Doing my eyelashes is the task I love most, the contortions my face goes through and the sense of increased length and weight of my mascara as I bat my eyes stirs deep feeling of femininity in me. My make up brush glides across my cheek, leaving a soft warm coral glow, giving my face an unmistakable girlish sexy embarrassed look that I love. I know why women do all these things , to attract and entice males and now I’m doing what women have done for the same reason. I take my sweet time to make sure I look alluring and erotic, I dream of having a boyfriend to fuck me. I couldn’t wait to squeeze into my beautiful full boned corselet, it always gave my slim body an sexy hourglass shape, next, I began sliding a pair of new silk stockings up my smooth legs, overcome with the sensuous texture against my shaven legs, I could hardly contain my girlish emotions, and felt as if I would climax right in my chair! My pussyclit calmed down finally, and then I slid into my new jet black lycra sheath skirt with the new black silk blouse he bought for me to go with it, it has a front lace-up bodice that I adore, it totally showcases my 36c breasts.As I looked in my vanity mirror, I touched up my lip liner, feeling a sense of total freedom. Trembling with anticipation, I reapplied my dramatic makeup spending extra time on my lips. Slipping my silk covered feet into my high heels, I gracefully make my way to Mistresse’s room, my hips swaying, I feel so sexy and very submissive. I was anticipating another night of dress up, as Mistress promised, when she saw me she said,”What are you doing?” “It’s dress up night, it’s on the calander.” “Not tonight!” she said. Well, we began to argue about it, and finally she steped up to me and slapped my face, “Alright Bitch, get in there!” She angrily tied me spread eagle to the bed. Finishing, she sat down and just looked me up and down with a smirk on her face. “You know I’m going to leave you, and then you’ll have to play all by your self, Lisa!” “What do you mean?” “I didn’t marry a man I married a sissy faggot, so I’m filing for divorce!”"Wait a minute" I interrupted and instantly she slapped me across the face very hard, it stung! "Bitch you may speak only when spoken to, is that understood?" and she slapped me across the face again. “Yes”, She slapped me hard twice more and with a stern tone "Yes what?" Shaking, I whispered "Yes Ma'am, I understand" Mistress slapped me two more times "say it louder!" "YES MA'AM, I UNDERSTAND" She grabbed me by the satin choker around my throat "Good girl! She pulled a little harder " nervous to stand up to me, I like that" she pulled my ear harder and laughed.... Slapped me across the face three more times...


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