A Little Favor free porn video

A Little Favor Day 1 - Friday My neighbor Kathleen called me up one Friday evening and asked me if I could come over to her apartment and help her with something. She lives in the apartment next to mine, so I went over there. She was sitting at the kitchen table talking to a girlfriend. They were finishing up a bottle of wine and opening up another one. Kathleen invited me to grab a glass and sit down with them. We sat around the table talking and drinking wine. We drank that bottle and then another one. I was definitely feeling no pain. Kathleen spun one of the bottles on the table. It stopped and pointed at her friend, Mary Ann. Mary Ann stood up and walked over to give Kathleen a kiss. I almost fell on the floor. It was so hot watching them kiss. Mary Ann spun the bottle next, and it pointed at me. She came over and sat on my lap and gave me a nice lingering kiss, but nothing like the tongue lashing she had given Kathleen. I was pretty hard by this time, and I suspect it was pretty obvious. I spun the bottle next, and it pointed at Kathleen. She pulled me over to her and had me sit on her lap. She put her hand on my crotch and discovered my hard on. She stuck her tongue in my mouth and leaned me back so that I was off balance and she supported me with her arm. The whole time, she was playing with my hard on. Let me describe the two girls to you. Kathleen is originally from Texas. She's over six feet tall in her stocking feet with long wavy red hair and bright green eyes. Her skin is pale and smooth like a porcelain doll. She has the body of a 50's pinup. Not too thin and not too fat. Just right. She is a natural 10 if I ever saw one. Her friend Mary Ann is from a small town in the Deep South and has a thick Southern accent. She is at least 5' 10, blond and beautiful. I'm not much to look at. 5' 7", 130 lbs. The only physical attribute I have going for me is that I am rather large where it counts for guys. Kathleen sat me back up and said, "We called you over to see if you could do us a little favor. Mary Ann is getting married in three months, and I need some help. You stand up and let Mary Ann stand back to back with you." I stood up and Mary Ann stood with her back to mine. Kathleen had me stand on my toes. She looked at us and took out a measuring tape. She took all sorts of measurements. "I think you'll be perfect" she said. "Will you help us?" My inhibitions could not have been any lower if I had been under anesthesia. "Of course I'll help," I said without thinking. Both girls laughed and jumped up and down. They smothered me with hugs and kisses. Kathleen took me by the hand and pulled me into one of the bedrooms. It had been turned into a sewing room. "I need you to be my dress dummy while I finish making Mary Ann's wedding dress. She's going out of town for the next few weeks, so I need somebody to wear it while I work on the hemline and put the finishing touches on it." "Wait a minute, I had no idea you wanted me to wear a dress. There's no way I'm going to do that," I said. "Are you going back on your word? You already said you'd help us. What kind of man are you?" scolded Kathleen. Her eyes were giving me a warning. I looked at Mary Ann and she looked sad. Mary Ann pleaded with me, "Please help us. It will mean so much to me. It will only take a little bit of time out of your day. I'll even pay you for your help. How does $25 an hour sound?" Kathleen said, "It will take a couple of hours a day, but it will need to be every day for the next few weeks." I asked, "Why can't you just use a regular dress dummy?" "The dress won't hang right on a dummy, and if you wear it, I will be able to see how the dress looks when you move in it. It really makes a huge difference to have a person be the dress dummy." I knew I was beaten, "What do I need to do? I don't want you to get any funny ideas about me if I agree to help you out." "Don't worry. We'll take care of everything," Kathleen said. She had a look like the cat that ate the canary. Mary Ann told us she was going to head home so that we could get started right away. She gave me a hug and a kiss on the cheek. "Thank you so much for your help. You have no idea how much it means to me." She hugged Kathleen and then left. Kathleen took me by the hand and led me into the bathroom. "I need you to take off all of your clothes." I was quite embarrassed. "Why do I need to do that?" "You need to be clean and hairless before you can put on the dress. You don't want to get dirt and hair all inside of her dress do you?" I stood there meekly while Kathleen stripped me and then took some hair remover and spread it all over my body from my beard line all the way down to my toes. I was embarrassed when she reached my manhood, which was fully erect. "That's quite a big tool you've got there. We'll have to do something about that later." She had me stand for what seemed like an eternity. Finally she turned on the shower and let me wash all the foul smelling chemical and hair down the drain. I used her body wash and shampoo so that I smelled very feminine when I got out of the shower. Next I was dried me with a pink fluffy towel. She applied moisturizer followed by some nice smelling powder. "I have one more thing I need to do. You're not going to like it, but it is an important step to help me reduce your waist. I need to give you an enema." I didn't think I could be any more shocked than I already was. "Why do you need to do that?" "We need to reduce your waist, and that will allow me to lace you a bit tighter. Don't worry about it; you'll feel much better when it is done." Before I could argue any more, she bent me over and stuck a nozzle in my rear and emptied a warm soapy mixture into my backside. It wasn't long before I felt a cramp and sat down to empty my bowels. I cleaned up and then we repeated the process. I did feel a bit better once she was done. She took me by the hand again and led me into the sewing room. She had me stand in front of a bar that was suspended from the ceiling. Hanging from the bar were two white leather cuffs. "This is a lacing bar. I will use it to lace you into the corset. The cuffs will help you hold onto the bar." "You didn't say anything about a corset," I complained. I had my hands in front of me so that she would not see my hard on. "How else are you going to fit into the dress? Mary Ann is going to lace down to twenty-two inches for her wedding. You'll need to do the same. Don't worry; we'll get there soon. I don't need you to be down to that size for a week. Your waist is only 28 inches. I can easily take 4 inches off your waist tonight. We'll take at least a ? to ? of an inch off your waist each day over the next week. You'll barely notice." Before I could protest, the cuffs were on my wrists and tightened. She pulled on the rope attached to the bar and easily lifted me so that I was stretched and was forced to stand on my toes. The cuffs were tight. I realized that I was really at her mercy. She couldn't help notice my raging hard on. "Your protests sound genuine, but your body is giving you away. I think you like what we are doing." I hung my head ashamed and didn't say a word. "Don't worry; it is really turning me on too. I think we're going to have a lot of fun." She took a tube-shaped garment and worked it up my body. It was made of spandex and clung tightly to my body. "This is a corset shield. It will protect the corset from your body oils, and it will protect your body from being chafed by the corset." The next thing was the corset. It was white with lace at the top and bottom edges and had five wide garters hanging down for each leg. It went from the bottom of my chest to my hips. It had a front busk closure and laced up the back. Kathleen had loosened the laces and wrapped it around me. She closed the busk around my front and adjusted the corset on my body. "OK, here we go." I felt her start at the top and tighten the laces toward the middle. Then I felt her start at the bottom and tighten the laces to the middle again. This process was repeated several times. Slowly the corset began to modify my shape. I maintained my erection during the lacing process because she kept rubbing her body against mine and breathing in my ears and on my neck. Eventually it really started feeling tight. "I have tightened it almost as much as I'd like to tonight. We need to let the corset rest and form to your body. I'm going to tie it off and wait about twenty minutes before I continue." She started to walk out of the room. "Hey, can you at least let me down? My arms, shoulders and calves are starting to cramp," I complained. "Oh, don't be such a baby. If you want, I can give you a pair of shoes to wear. You'll need to get used to them anyway since you'll be wearing them with the dress." Without waiting for an answer she left and came back with a box and a plastic package. "I'll have to put some stockings on you first." She picked my left foot up and carefully pulled a stocking up my leg. She pulled and smoothed it until it was just right. When it was, she attached it to the five garters hanging down from the corset. The feeling of the stocking was out of this world. She spent more time than necessary fussing over them. This was driving me crazy, but I was trying not to show it. Unfortunately my penis had turned purple. She put the stocking on my left leg next. "Don't be embarrassed. I love the feeling of sheer stockings on my freshly shaved legs. Don't they feel divine?" All I could do was nod my head. She took my left foot and fit it into a shoe. "Your feet are about the same size as mine, so these should fit you OK. They are my only pair of five-inch heels. At my height, I don't get a chance to wear them too much otherwise I tower over almost everyone." I looked down and saw a pair of black patent leather pumps. "I'll be back in a few minutes, so don't go anywhere." I told her I'd just hang around until she got back. That elicited a slight laugh from her. Eventually, she returned and stood in front of me. Even with the heels on, she was still several inches taller than I. She kissed me and pulled me close. She ran her hands up and down my corseted body and then my stocking clad legs. She went behind me and started biting and licking my neck and shoulders. She quickly had my blood pressure as well as my erection back into a critical state. "Time to tighten your corset a bit more." She untied it and began tightening it again. When she was done, she tied it off. The lacing and compression was a real turn on for me and she knew it. "Let's put your panties on you." She showed me a tiny pair of white silk panties. "Oh these won't ever fit with that monster sticking out in front of you. I hope you don't mind if I do something about that. We can't have you causing a big tent in the front of the dress." Before I could ask her what she meant, she reached around from behind me and grasped my penis in her hand. She was wearing satin gloves. The feeling was out of this world. She licked and bit my neck and ears while she jerked me off. It didn't take long for me to shoot my load. She caught it with a wad of tissues. While I was recovering, she had me lift one foot and then the next. She pulled something metallic up my legs. I felt her put a belt around my waist. She came around front and took my penis and forced it into a tube. Next she pulled up a plate from between my legs and attached the tube to it. She pushed the plate into the belt that was around my waist. I heard a click. "This will keep that monster in check." "What is that?" I asked her. "It's a chastity belt. It will give you a smooth profile so that the dress will look nice on you. As you can probably feel, it keeps you tucked back between your legs. You'll need to sit down when you go to the bathroom. Try to relax for the next step. It has a rear shield to protect you from any unwanted attention." I felt something cold and slippery pushing against my rectum. "Hey, what the hell are you doing?" I shouted as she pushed the intruder home. I heard another click from behind me. "This belt belongs to Mary Ann. She bought it for an old boyfriend who had cheated on her. She left me the key to the rear shield, but forgot to leave the key to the front of the belt. I'll give you an enema every day so you won't have to worry about having to defecate with the plug." I felt her attach two cuffs to the tops of my thighs about eight inches above my knees. I could feel chains on my thighs that attached the cuffs to the belt. "Oh by the way, this belt comes with thigh cuffs. I don't have keys to them either, just to the cable that goes between them. With the cable in place, you won't be able to wear pants. She said she will bring the other keys when she gets back in a few weeks." "What the hell are you doing to me? Why are you chaining me up like this? I didn't agree to any of this!!! I demand that you let me out of this right now! I'm done with this!" Kathleen came around front and looked me eye to eye. "You're done when I say you're done. You had better apologize for talking to me like that." I refused and she went out of my sight into a closet. "You'll find that I am rather fond of corporal punishment." She pinched my nipple causing me to let out a cry of pain. When I opened my mouth, she stuffed a ball in it. I soon had a ball gag tightened around my head. "Have you ever felt a riding crop or a cane?" I shook my head no. "You are in for a real learning experience then." I heard a swish and then felt a searing pain on my backside. It was quickly followed by four more. The pain was intense. "That was a riding crop. I enjoy riding horses, so I'm pretty good with it." I heard another swish and felt a pain so intense I thought I was going to pass out. It was followed in short order by four more. "That was a cane. You'll find that the cane causes a bit more discomfort than the crop. My former lovers tell me they prefer the crop to the cane." I had tears pouring down my face and hung from the lacing bar while I was trying to catch my breath. She put her hands on my face and wiped away the tears. She then put them on my battered butt. They felt cool but hurt a little. She kissed my face and hugged me. "Just live up to your part of the deal, do what I say and we won't have to do that again, although I do get a kick out of it. For the next few weeks, you'll need to do exactly as I say so that we can get the dress finished on time. If you behave, I think we will enjoy our time together. I'm going to remove your gag, and I expect you to be quiet. Are you going to be good?" I nodded my head yes, and she removed the ball gag. I moved my jaw to relax the muscles. "I'm going to let the lacing bar down, so you'll need to stand on your own." She slowly lowered the bar. I found it difficult to stand in the heels at first, but I eventually got my balance. My legs, arms, shoulders and butt were all very sore. She had me walk around the room a bit to get the blood flowing again. "You need a lot more practice walking in those heels." She gave me some tips and I was able to walk a bit better, but she said I still needed a lot more practice. I wasn't sure why I needed the practice, but decided this wasn't the time to argue with her since the cane and crop were still close at hand. "OK, let's get you dressed so we can see how well this is going to work." She pulled out a big pile of white ruffles. "This is a petticoat. You'll wear this under the dress to make it look full." She had me step into the middle of it and then pulled it up and tied it at my waist. It made a lot of noise and I could feel myself trying to get hard inside the chastity belt's tube. "Next is the dress. For now, we'll just put it on without trying to fasten the back. We won't be able to fasten it until you are laced down to 22 inches in a week or two." She pulled the dress over my head and put my arms through the sleeves. It revealed most of the arms, and had a plunging neckline. If I had cleavage, it would have shown that off. "Oh, I almost forgot. You'll need to have some breasts too." She pulled the dress down in front and off my arms. She held out a bra in front of me. It was made of white satin material and had breast forms in it. In no time at all, she had it hooked up in back. She pulled the dress back up my arms and fastened the top button behind me. She got out her measuring tape and took a bunch of measurements which she compared to Mary Ann's measurements. "The five inch heels make you the same height as Mary Ann with her 2" heels. I think this is going to work out just fine. I'll need you to step up on this platform so that I can start to do some work." She helped me step up onto a platform that was several feet tall and allowed her to sit comfortably while she worked on the dress. "It is a lot easier and cheaper to do this with a machine, but my clients prefer to have their dresses hand stitched and hand beaded. I earn a lot of money making these dresses to those with the most discriminating tastes. In order for you to be laced down to twenty two inches, you are going to have to wear that corset all the time until we are finished. In fact, the chastity belt would be pretty uncomfortable without the corset. I'm going to have you stay with me all weekend, and you'll practice walking in heels. How does that sound?" I was trying to think of some excuses because she had taken me by surprise again. "I have a lot of errands to run this weekend, and some stuff I need to do for work as well as shop for groceries and do my laundry. I couldn't possibly spend the whole weekend with you." Without losing a beat she said, "We can take care of that. There's not much you can't do while wearing a corset and heels." I knew I wasn't going to win this argument. My best bet was to somehow sneak out of her apartment and get to mine where I could get out of the corset and chastity belt. I plotted and planned while she worked on the dress. After an hour she said, "Let's take a break." She helped me step down off the platform but told me to stay where I was. My feet were really getting uncomfortable in the heels. When she left the room, I took the liberty to step out of the heels and give myself a rest. She returned shortly and gave me a stern look of disapproval as she towered over me. "Didn't I tell you to stay where you were? Did I give you permission to take off your shoes? I can see you are going to need a lot more training. Remind me to give you five with the crop before we go to bed tonight." I pleaded with her not to do that, but she warned me that whining and complaining would only result in her doubling or tripling the punishment. I knew I was on a slippery slope. The best I could hope for was that she would let me go back to my apartment alone. "Let's get your shoes back on you." She helped me keep my balance while I stepped into them. "I've got just the thing to keep you from being naughty again." She opened a drawer and pulled out two sets of black straps. She lifted the dress and petticoats so she had access to my shoes. I felt her put something on the shoe and then put a strap around my ankle. She repeated for the other foot. Then I heard two distinct clicks. "Now your shoes are locked onto your feet. We'll let you keep them on for a day or two so you can get used to them. OK, back to work." With that she helped me climb back up onto the platform. She worked for another hour and then said it was time to quit for the night. "You'll need to stand still the next time we do this. Since this is your first night, I didn't want to be too harsh on you, but from now on, if you can't be still, I'll have to take some steps to insure that you do not move unless I ask you to move." She helped me down off the platform and removed the dress and the petticoats. There was a full length mirror where I could see myself. From the neck down, I really looked like a woman wearing a bra, corset, stockings, high heels, and of course the chastity belt. She came up behind me and put her hands on my waist. "You really look hot. I can't wait to see what you will look like when you are laced down to twenty inches." An alarm bell went off in my head. "Didn't you say I had to get down to twenty two inches, not twenty?" I asked. "Well, you may decide that you enjoy tight lacing and want to go even smaller. Some people can achieve a ten inch waist reduction from their natural waist size. You might even be able to get down to nineteen," she said with a twinkle in her eye. Now I was really getting nervous. "Let's get you ready for bed," she said. She took me by the hand and led me to the bedroom on the other side of the apartment. We washed up and then she took me into her bedroom and took out a white silk nightgown for me to wear. "Every bride should wear white on the night of her honeymoon. With that chastity belt in place, I think you might just recover your virginity," she said with an impish smile. "Why don't you let me go over to my apartment and let me get some of my own pajamas? I'll be a lot more comfortable." "Not a chance. I'm not letting you out of my sight when I'm feeling this horny. You have no idea how turned on I am right now. I've always wanted to find a man who would let me do the things I've done to you tonight. You're going to make my fantasies come true. I suspect that we'll fulfill a few of yours along the way." She had me put on the nightgown, which came down to about the tops of my stockings. "You'll need to use the bathroom before going to bed. Don't forget to sit down to pee." It took me a few minutes to go. Once I did, I could feel the warm liquid partially flowing out the tube and heard it drip into the toilet. She gave me a squirt bottle and showed me how to clean and rinse the urine out the best I could. She also showed me how to dry the belt. "Aren't you going to at least let me out of these shoes or corset before we go to bed? I can't wear them to sleep." "No chance. If I remove your corset, we'll lose all the progress we've already made. The shoes you'll wear for taking them off without asking permission. Weren't you supposed to remind me of something?" she asked. Despondently I said, "I'm supposed to remind you to give me five with the crop." "Excellent," she said. "Wait here for a minute." I stood there while she went and retrieved her riding crop. She sat on the edge of the bed and said, "over you go." She had me lie across her legs. She lifted my nightgown exposing me. Without any warning she gave me five hard swats on my abused butt with the crop. She had me in tears again. Damn that thing hurt and she really knew how to use it. She stood me up and wiped the tears from my eyes. Without saying anything, she pushed me back on her bed and scooted me up toward the headboard. She opened her bedside table and produced two pairs of handcuffs. I was quickly secured so that I was flat on my back with my hands secured over my head. "Here's another game I like to play. You're going to lick my pussy. If I like what you are doing, I'll moan and groan. If I don't like what you are doing or if I get tired of it, I'll swat you with the crop. I think you'll find that you will be a very inventive lover." Without further warning she lifted her bottom and sat on my face. All I could see was that she was wearing black stockings with a garter belt and a black thong. I went to work as best as I could around and through the thong. She helped me a bit by using my hair as reins and steering my head to where she wanted me to lick. She only used the crop a few times, and it was not very hard. She had me lick her to several orgasms. My poor penis was doing its best to overcome the constraints of the chastity tube, but it was to no avail. Finally she scooted back and collapsed on top of me. She kissed me deeply and worked on my neck, shoulders and ears. It felt so good but was pure torture at the same time since there was no way I could achieve an erection. She drifted off to sleep while lying on top of me. Eventually she rolled off of me, but I could not get comfortable. She woke up a couple of times during the night and we played the same game again and again. She was insatiable. My tongue and jaw were aching. Thankfully she game me some ice water which made me feel a little better. I asked her if she would free my hands so that I could sleep better. She un-cuffed them from the bed, but then cuffed them behind my back, and attached to the back of the chastity belt. I could only get comfortable lying on my stomach. I did manage to get a little bit of sleep. Day 2 - Saturday When Saturday morning finally arrived, she un-cuffed my hands from behind me and cuffed them to the headboard again. She again rode me to orgasm. "I hope you slept well last night, because we have a full day ahead of us. Let's get you cleaned up," she said. She un-cuffed me and led me into the bathroom. She started the shower and removed my clothes and shoes. She unlocked the rear shield on the chastity belt, and proceeded to give me two enemas. She left the rear shield unlocked so that I could clean it while in the shower. She unlaced my corset and removed the corset liner. I felt my waist expand. The chastity belt was a bit tight on me. She pulled me into the shower and scrubbed me all over. Next she had me scrub her. She teased me and kissed me. I was trying to achieve an erection, but was frustrated by the chastity belt. I could tell the she was a bit frustrated too. Soon we were both clean. We stepped out of the shower and dried off. She took a tube of KY jelly off of the counter top and applied it to the anal plug attached to the rear shield of the belt. Carefully, she eased it into me and brought the rear shield up and locked it to the belt. She took me by the hand and led me back to the other bedroom. Without saying a word, she strapped my hands to the lacing bar and I was soon stretched up onto my toes. She placed a clean corset liner on me and left the room. She returned with the corset, shoes and straps. She was able to get the corset around me and under the chastity belt. She began tightening it again. Within a few minutes it was really tight. She took out a tape measure and put it around my waist. Next came the bra with the inserts. "Twenty-four inches!! Only two more inches to go." She put a clean pair of stockings on me, and worked them carefully under the chastity belt's thigh cuffs. She took out a short piece of flexible cable and two locks. She locked the cable so I could only separate my legs by a few inches. There was a knock at the door and Kathleen left me to go see who it was. I heard Mary Ann's voice and a man's voice. He wanted to see the dress, but the girls would not let him. They told him it would be bad luck for him to see it before the wedding day. I was really glad they did not allow him back there. I did not want to go through the humiliation of having another man see me locked into the chastity belt and laced into the corset. Mary Ann rolled a suitcase into the room while Kathleen talked to the man. Mary Ann came up to me and kissed me and ran her hands over my corseted body and stockings. "That Kathleen is a lucky girl to find a man who would allow her to play dress up. I'm going to have to figure out a way to get my macho fianc? to let me feminize him." Before I could ask her about the keys to the belt, she was gone. I heard them say their goodbyes and Kathleen returned to the room. She took the suitcase that Mary Ann had brought and put it on the bed and opened it up. There were quite a few dresses as well as skirts, slips and tops. "Mary Ann brought over some of her things that she thought would fit you as well as some new high heels. I need for you to dress as a girl today so you can work on moving around in high heels." She lowered the lacing bar and unbuckled the cuffs. Instead of having me put on the petticoats and dress, she took out a black slip and put it over my head. It covered from my shoulders to about mid thigh. Next was a short black dress. She left for a few minutes and came back with a white apron that she tied around my waist. "You can be my maid and clean up around the house while you practice walking in heels and moving in the corset." "But Kathleen, what about all of the things I need to do in my apartment and outside the apartment. I'd like to get my laundry done as well as do some clean up." "You can start by cleaning my kitchen from top to bottom," she said. "I'll run next door to your apartment and get your dirty laundry. You can use my machines to do your laundry today." She left and in a few minutes was back with my dirty laundry. Kathleen watched me as I moved around. She helped me to learn how to walk in the heels and move in the corset. It took quite a bit more effort than I was accustomed. With her help, the kitchen was soon spotless. We stopped briefly for breakfast. She had me cook her eggs, bacon and toast smothered in jam. Unfortunately, she said that I needed to lose weight, so I could have a piece of dry toast. After breakfast I cleaned up the dishes and worked on the laundry. "It's time to get some more work done on the dress," she said. I walked into the sewing room, and she helped me out of the clothes I had worn this morning. She attached my arms to the lacing bar one more time, and untied the corset. She pulled on the laces some more, and then tied it off. "Twenty-three and a half inches!!! You'll be down to twenty-two inches before long." She eased down my arms and then had me stand at the mirror. We put on the petticoats and dress. Soon I was up on the platform and she was sewing. My mind was wandering and I was trying to figure out how the heck I had gone from being a free man to one wearing a very tightly laced corset, stockings, bra, high heels, petticoats, wedding dress and the chastity belt. "You are moving around too much. It makes it difficult for me to sew with you moving around. If you can't be still, I'll have to make you be still." I wasn't sure what that meant, but I didn't like the sound of it. I tried to concentrate on standing still, but my feet, ankles and legs were starting to ache. I needed to move occasionally to ease their strain. "Ok, that's it. You're moving way too much." "Please Kathleen, these heels are murder on my feet. I have to shift around to ease the strain." She took a length of rope and tied it tightly around my ankles. "This will keep you from moving around, but don't lose your balance or you will have a long fall." She put a white leather posture collar on my neck. It had two wrist cuffs attached to it. I was immobile and was pretty helpless. "Now, don't lock your knees or you will pass out. If you start to feel faint, let me know and I will let you take a break. That should do for now. Now, you better not move around, or else." I was as still as I could while the time ticked by. After what seemed like an eternity she said, "OK, it's time for a lunch break." She released my hands from the cuffs, untied my ankles and helped me get the dress and petticoats off. "Put your dress and apron back on so you can make us some lunch." I put the dress, slip and apron back on and went out to the kitchen to make lunch while she finished up in the sewing room. I was trying to figure out how to get out of this situation. On the one hand, I was receiving a lot of attention from a woman I found incredibly beautiful, but on the other hand, I wasn't sure I liked the attention. I had to admit to myself that the feminine clothes, chastity belt and bondage were a bit of a turn on to me. It never occurred to me that these things could be appealing. After all, I'm not gay. The thought of being with a guy was repulsive to me. I had started making lunch and was very hungry. She made sure that I only had half a sandwich and some fruit. "You need to lose a little bit of weight." I was a little perturbed, but after I ate my meal, I was pretty full due to the restriction of the corset. Over lunch we talked about the progress she was making on the dress and how much longer it would be until it was done... still quite a while. After lunch, I didn't wait to be asked to clean up the kitchen. I just did it while Kathleen went into the bedroom to lie down for a bit. I was hoping she might fall asleep while I puttered in the kitchen, but I wasn't so lucky. "Come in here and lay down with me," she called. She had removed all her clothing except her bra and panties. "Take off your dress and slip," she said with a smile. I complied and thought to myself that I had lost another opportunity to try to escape. I stood there in my corset, bra, stockings, heels and the damn chastity belt. I wanted to rip that thing off and have my way with her. "Be a dear and lie down on your back. I'm feeling a bit horny." I climbed onto the bed and lay down. She straddled my face facing toward my feet. She was already very wet. "Use your tongue on me. Ooooh, that feels good." While I was doing my best to pleasure her, she was running her hands over my legs and corseted body. It felt really good, but extremely frustrating. I wanted to ask her to try to get Mary Ann to send her the keys, but couldn't. "Seeing you in your lingerie and chastity belt really makes me horny. I would love to see you in nothing but silk and satin and lace forever. No trousers for you. You're not that kind of girl." She said in a heavy voice. She was turning herself on even more saying these things and grinding down on my face. She worked herself up to a very intense orgasm. When it hit, she arched her back and then collapsed on top of me. "Oooh, that felt so good. I wish I could have your hard dick in me while you are laced up in your corset. That would be such a rush. I have an idea though." She got off of me and went to one of her dresser drawers. She pulled out a realistic looking 8" dildo. That made me very nervous. "Don't worry, sweetie, I'm not going to use it on you." There was a spot on the front of the chastity belt that allowed her to screw the dildo to the front shield. "Put your dress back on." I did while she put on a simple summer dress with no panties on underneath. She walked over to me and started slow dancing with me and kissing my mouth, neck and ears. She maneuvered the dildo so that it was between her legs and she was riding it without inserting it. "If you like what we are doing, we can keep it up after the dress is done." I was extremely horny and would have agreed to practically anything she said. "I'd love that" I said. She got a big smile on her face and led me back out to the kitchen. She had me sit in one of the kitchen chairs. The dildo was making a big tent in my dress. She pulled up the dress and slip and impaled herself on the dildo while straddling me. Her breasts were right in my face, so I did my best to suck on them through her dress. "Oh, I've always wanted to screw a man like this. Doing this with a man dressed as my maid is so kinky and hot." While she rode me, the butt plug was being driven in and out of me. The combination of her moans and being impaled by the plug was driving me crazy with frustration. I had to get out of the damn chastity belt. It did not take her long to orgasm and collapse on me. "Mmmmm, that was good. We'll have to try that again later," she said with a satisfied smile. "OK, let's get back to work on the dress." We went into her sewing room and I took off my dress and slip. She took me by the hand and cuffed me to the lacing bar again. Soon she had me stretched up and was pulling in the corset some more. It was extremely tight and a bit hard to breath. She let me down from the lacing bar and then pulled the petticoats and dress over my head and into position. She helped me up onto the platform. Soon my ankles were tied and I was collared and cuffed. "Stand up straight and don't lock your knees." While she was working she asked me about myself and my job. I told her all about me and found out more about her background. She told me she was the first born of six kids, and was left in charge to take care of her younger siblings quite frequently. She had always been one to take charge and did not like working for anyone else or being dominated by them. "I would like to have a relationship with you once the dress is complete, but if we are going to have a relationship, you are going to have to obey me. If you are naughty or disobedient, I will punish you. I will tell you what to wear and what you can and cannot do. I am really starting to like you a lot. Think about it over the next couple of days. I hope you decide you want to continue with me." "If we have a relationship," I asked, "would you let me out of this chastity belt and let me wear my male clothes?" "The chastity belt belongs to Mary Ann, but I would like to see you in one. If you are well-behaved I will let you out periodically to play, but I like how it gives you a nice smooth front. If you agree to become mine, you will be corseted all the time. You need to be tightly laced, and you belong in silk, satin and lace. It will be a long time before I will allow you to wear trousers, if ever. Even if I do, they will be women's trousers." "I have mixed feelings about all of this. I'm extremely frustrated by the chastity belt. The plug is very uncomfortable. However, I have to admit that wearing the women's clothes and the bondage is a real turn on. I'm not sure I can make it a couple more weeks with this level of frustration, but I don't see how you have given me much choice in the matter." "Precisely. You agreed to help, so that is what you will be doing for the next few weeks. I'm glad you are enjoying yourself. I think you'll get used to the plug being there. Dominating you and seeing your frustration really excites me. I won't apologize for it. It is who I am. If you decide to stay with me, you will have much more of the same." "You have given me a lot to think about. What about my work? Are you going to let me go to my apartment and work from there during the week?" "No, I have decided that I will go over there and bring your work materials back here. You can use the desk in the sewing room. That will let me keep a good eye on you." Crap, I thought. I'm never going to get the chance to escape, but I started thinking that maybe I did not want to escape. "I don't want you to answer me today; I just want you to be thinking about it. So what are you going to make me for dinner tonight? I think we will need to work on your cleaning and cooking skills in case you decide to stay." We had a pleasant conversation while she continued to work. She told me about cooking and sewing. I had a feeling I might soon be working as a seamstress... er I mean tailor soon. "OK, that's all for today. Let's get you down from there." She untied my ankles and helped me off the platform so she could remove the collar and cuffs. The wedding dress and petticoats were removed. It felt good to move my muscles. They were really starting to get sore from staying in the same place for so long. She helped me put the slip and dress back on. We prepared dinner together and enjoyed it with a bottle of wine by candle light. After dinner, I cleaned up while she went into the sewing room. "When you are done cleaning up, come in here and see what Mary Ann brought you to wear. I'd like you to do a fashion show for me." When I was done, I went into the room. Kathleen had unpacked the suit case and had opened the box of shoes. There were lots of dresses, blouses, skirts and slips. She had bought me three pairs of high heel pumps, white, red and pink. There was also a pair of knee high boots in red. "Let's get you undressed and try some of this stuff on." I was stripped of the black dress, slip and she unlocked the shoes and removed them. It felt really good to stand flat-footed again. All of the clothes seemed to fit just fine. She had me try on each of the shoes and walk in them. "I've always loved boots, let's get those on you." She had me sit down and put the boots on. I had a heck of a time trying to put them on in the corset. It would not let me bend. After struggling for a bit, she took them from me and put them on. They had a zipper up the side which made putting them on a bit easier. "Put on this short little red silk dress, I want to see how it looks with those boots. I think the colors match perfectly." I put the dress on and she zipped it up the back for me. "With that narrow waist and your thin legs, you look really hot in that. Those boots are quite sexy." I didn't know what to say... I was heading down the slippery slope with no hope to gain any traction. She touched my cheeks to see if there was any stubble, which there wasn't due to the hair removal treatment yesterday. "Let's put some makeup on you and see how you look. I want you to pay attention to what I am doing because you will be expected to be able to do it by yourself." "Wait a minute," I said. "I agreed to help you with the dress; I didn't agree to wear make-up. This isn't part of the deal." She looked at me crossly. "In case you haven't noticed, you are in no position to make demands. You didn't agree to wear the chastity belt, high heels, corset or have your body hair removed, but you allowed it to happen. I don't appreciate your rude tone." She grabbed my hands and pulled me over to the lacing bar. I started to resist, but she was stronger than I, and it was hard to fight while wearing the high heeled boots. "You better stop fighting me, if you know what is good for you," she said in a menacing tone. I knew I had been beaten, again. She attached my wrists to the lacing bar and pulled it up so that only the toes of the boots were touching the floor. "You obviously forgot about the cane and need to be re- introduced to it." "Please don't use the cane on me," I pleaded, but it was no use. "Open you mouth." I did and she filled it with a gag. I was already starting to cry. "You are starting to remember the cane now, aren't you?" she said with a sneer. She lifted the hem of the short red dress and pinned it up in back which left me exposed from my waist to my knees. She unclipped my stockings from the garter tabs and allowed them to fall down my legs. The only protection I had was the thigh cuffs attached to the chastity belt. "For being rude, I will give you five. For resisting me, you get ten more." With no warning she let fly with the barrage. She made sure that each blow landed in a different spot, and she allowed a couple of seconds between each one. I struggled to get away, but it was hopeless. After an eternity, it ended, and I was in severe pain. She came around front to look at me and wipe my tears away. "Last night I took it easy on you. I just wanted to give you a warning. Tonight you have been punished. You have fifteen long red welts on your back side from your butt down the back of your thighs. The next time I ask you to do something, you better do it gladly, or you will get more of the same. As you have probably noticed, I am very, very good with the cane. Don't make me punish you again." With that she walked out of the room. She left me hanging there for quite a while. My whole body ached. I could hear her taking a shower. Apparently I had made her very mad. When she finally came back to let me down, she put some soothing cream on the welts first and then lowered me down so that the heels of my boots were touching the floor. She removed the gag. "I'm sorry I was rude. All of this is so new to me. Please have some patience with me and forgive me," I said. She smiled and gave me a lingering kiss on the lips. She hugged me, and then gave me another kiss. She made sure I could stand before she released me from the lacing bar. "Let's get you cleaned up and go to bed." She helped me undress and take a shower. It felt great to be out of the corset for a bit. I wished I could have removed the chastity belt too. After a quick shower, she helped dry me and then rubbed moisturizing cream all over me. Then it was back to the lacing bar and I was laced back into the corset with a new liner underneath. She had me put on a short white silk night gown. She simply wore a black jog bra and panties to bed. We were both exhausted. I fell asleep while she spooned me from behind. Day 3 - Sunday I woke up still cradled in her arms. I slipped out of bed and made it to the bathroom. My backside was really sore from the abuse over the past two days. I thought about reaching behind me to loosen the corset, but knew that would probably cost me. I was wondering if I could find the keys to my apartment and sneak over there before she woke up, but I heard her get up and knew I had missed my chance. She smiled when she saw me sitting down using the bathroom. It was hard to believe how beautiful she was. I could not believe that she would be interested in a guy like me. Of course not many guys would have let her do the things she was doing to me. Had it really only been about 36 hours since this whole thing started? She gave me my morning enemas and after getting cleaned up, we made some breakfast. After breakfast, she said, "Sunday should be a day of rest. We won't work on the dress, but I think you should still do some light cleaning around the apartment so that you can improve walking in the heels and moving in a dress. Let's get you dressed." She led me into the sewing room where I was attached to the lacing bar. She tightened the corset some more. It was very tight again. She took out a measuring tape and I was down to 23 ?. "I think you were born to wear a corset. Look how tiny your waist is becoming." She turned me to face a full-length mirror. I could not believe how tiny my waist looked. She let me down from the lacing bar. "Let's find you something to wear." We looked through the clothing that Mary Ann had brought yesterday. She found a light pink colored silk blouse and a short white skirt. She had me put on the bra with the inserts and a pink silk camisole. Next she instructed me on how to put on the stockings. It was not easy in the tight corset. I smoothed them up my legs, carefully fed them under the thigh bands and attached them to the corset. I could feel myself trying to get hard in the chastity belt, but the penis tube was too tight. Next on was the silk blouse. It was very soft and caressed my exposed skin. I stepped into the skirt and pulled it up. I tucked the blouse into it. The skirt barely covered the thigh bands and stocking tops. Next on were the pink pumps. "Now I want you to wear these shoes all day. I don't want you to take them off without permission. Do you understand?" "Yes, I do." I rubbed my bottom remembering yesterday's lesson. "Good. We are going to practice putting on your make up first." I followed her to her bedroom and sat at her vanity. We spent an hour or two working on putting the make up on and then taking it back off. By the time we were done, I could do a pretty decent job. With my short hair, I did not think that I was a very convincing girl, but she thought I looked pretty good. We spent another hour with her having me learn to walk like a woman. She taught me how to sit and stand. She also taught me how to squat down to pick up things so that I would not expose my lingerie. The thigh bands were a constant annoyance. They limited the distance of my pace. This actually helped me to walk more gracefully, but it was still an annoyance. "OK, go get the feather duster from the laundry room. I want you to dust everything in the apartment so that you can practice walking, reaching and moving. I'm going to catch up on some reading while you practice, but I'll be keeping an eye on you." I did as instructed. My feet were starting to get sore after all the time I had been standing in the heels, but I did not complain or remove them. I did not want to have them locked on my feet again! I could feel her eyes on me. I turned around once or twice and saw here watching me. Occasionally, she would give me suggestions on how to move. I was lost in thought and was startled when I felt her come up behind me and grab me around the waist. She kissed my neck and shoulders. "I can't stand watching you any more. Get your butt into the bedroom and get undressed." I did as instructed. She practically ripped the blouse and skirt off me. She pushed me back on the bed. "Leave your shoes on." She tore off the shorts, t-shirt, thong and bra she was wearing. She quickly mounted my face and had me use my tongue. She was already very wet. She faced my feet and ran her hands along my body while I went to work pleasing her. She orgasmed very quickly, then turned around and laid on top of me and kissed me passionately. "You are so hot in your lingerie and heels." She retrieved the dildo and attached it to the front of the chastity belt. She slammed herself down on it over and over while I watched her. I played with her breasts and kissed her while she fucked herself on top of me. She brought herself to another intense orgasm while I lay there on her bed frustrated. I was so frustrated that I had tears rolling down my cheeks. "Don't cry. Imagine how good it will feel to be inside of me. If you are very good, I will let you do that once in a while when I get the key." After resting a bit, she climbed off of the dildo and had me lick her to another orgasm. She rolled off of me and fell asleep. I covered her with a blanket and went into the bathroom to clean up. I put the clothes back on and then re-did my make up to the best of my ability. I thought about trying to get back to my apartment, but the thought of being able to make love to this woman and spend time with her was just too appealing. I knew that she would trust me a lot more after this. I practiced walking and doing the things she had taught me. I was cleaning in the sewing room when I felt her grab me and spin me around. She pinned me against the wall and gave me a big kiss. "It was so quiet in here. I thought you had snuck out. I'm so glad that you didn't and that you got yourself properly made up and dressed. Why don't you make us some lunch? I'll go over to your apartment and pick up some of your things. Make a list of what you need and where it is, and I'll get what you need." I made a list and then made lunch. She was gone for a long time. When she came back, all she had was my work computer and things I would need for work. "You don't need the other things on your list. Did you really think I was going to bring you your male clothes?" "No, but I had to at least ask. This is a big change for me. It would be nice to wear a pair of jeans and a t-shirt once and a while." "You won't be wearing any rough clothes like that for a while if I have anything to say about it... and I do," she said with a smile. She put my work things in the sewing room while I put lunch on the table. While we ate, she talked about what she wanted to get done on the dress that week. She had a couple of other projects she needed to complete too. After lunch, I cleaned up while she did some things in the sewing room. After lunch, we watched a couple of movies and cuddled on the couch. She had me get up and get us drinks and snacks a couple of times. I made dinner again under her supervision. During dinner she asked me about my work, and how often I needed to go into the office. After dinner, I cleaned up and she went into the sewing room to plan her work for the next week. She had me look at the plans for some of her other projects and asked my opinion on them. "You should learn how to use the sewing machine so that you can help me with some of these projects." She gave me some scrap material and some patterns to follow. While I was practicing, she stopped me and gave me some pointers on how to make things look better. "I think you are a natural at this? Have you ever used a sewing machine before?" "No, I haven't. I have done some carpentry, but this is quite different," I said. "If you are willing, I think you could be a great help to me. It is getting late and we have to get up and go to work tomorrow." We went into the bathroom and removed our makeup. I took off the outer clothes I had been wearing. "Take off your pumps and stockings too," she said. "I have a very sexy nighty that I want you to wear." I found myself wearing a long white silk night gown with generous amounts of lace at the neckline and wrists. She wore a short black silk night gown. When we got into bed, she rubbed my body through the silk nightgown. It felt so good. She rolled my on my stomach and gave me a nice back rub while she nibbled on my neck and shoulders. It was so awfully frustrating, but felt so good at the same time. She rolled me on my back and attached the dildo. She mounted it and slowly rode me while she kissed me and continued her wonderful assault on my neck and shoulders. It was a nice, slow and gentle. She pulled off her nightgown so that I could suck on her nipples and caress her breasts. She rode me for a long time before she finally reached her climax. When she did, she kissed me one more time and went to sleep on top of me with the dildo still inside her. Day 3 - Monday I woke up to the sound of her alarm. "Let's go take a shower, and we'll wash each other," she suggested. First she gave me my two enemas. After that, we removed our night gowns and the corset was unlaced. My waist felt like it was trying to expand. We took a nice hot shower. I scrubbed her beautiful body. She scrubbed me and then helped me clean under the chastity belt and the penis tube as much as possible. We dried each other off and then I was quickly hustled back to the sewing room and the lacing bar. She handed me the corset liner to put on. I pulled it up my body. She showed me how to put it on and that the seam should be in the back. She handed me the corset, and I wrapped it around my waist and fastened the front busk. As usual, I was stretched up on my toes and hanging from the bar. She went to work tightening the corset. Soon my waist was being compressed. I was really starting to like the feeling of the compression around my waist and chest. "I'm gong to let you rest like that for a few minutes while I get dressed." My toes and feet were starting to ache from being stretched like that. After about five minutes she came back. "I'll bet you would love to wear your high heels, wouldn't you?" "Yes, I would," I answered. She smoothed some stockings up my legs, under the thigh bands and attached them to the garters. She ran her hands up and down them teasingly. "I love how you look so helpless in your corset, garters and stockings. You are making me horny again. I will remember this tonight how you teased me. I think I'll put you across my knees and give you a little bare handed spanking." She helped me step into the blue five-inch pumps which greatly eased my strain. I was left there while she got herself ready. After a half hour or so, she returned and tightened the corset some more. It was extremely tight. She took the tape measure and measured my waist. "Twenty-three inches. This corset only has about an inch and a bit more before it is closed all the way. I guess you'll have to move into a tighter one at that point." She came around the front and was a bit taller than I even though I was stretched. She put her hands on my narrow waist and gave me a kiss. "I think we can have you down to about a twenty inch waist by the time of the wedding. You'll have the tiniest waist of anyone there. What do you think about that?" "I think I'll get a lot of looks," I said. "All the women will be giving you catty looks, and all the men will want to get into your panties." "What do you mean panties?" "I told you that you won't be wearing any rough boy clothes for a long time, and you are definitely going to the wedding. So that means that you will be wearing a very feminine dress. I'll take you shopping when we get close so that you can pick out something you like." "Do you really think that I can go out in public and not be recognized as a guy in drag?" "You are almost passable now. We just need to work on your deportment some more as well as your voice." I still had not grasped that she really meant what she said about no more male clothing. "I don't understand why you won't let me wear my male clothing once the dress is done." "The choice is really yours, but I won't have anything to do with you if you decide to go back to wearing your boy clothes. I want you to be my chaste little sissy boy that I can keep all to myself. I guess I'm being possessive and selfish, but that is the way I feel about it. I love having the control over you, and I think you love it too." "I do love it, but at some level I thought it was just a game and we could go back to a boy and girl type of relationship." "I suppose it is a bit of a game, but it is one without an ending. If you want to have a boy and girl relationship, I can be the boy and you can be the girl," she said with a devilish grin. "Oh no, that's OK. I think I know where you are headed with that line of thinking." I was afraid she would have me bent over the kitchen table and have her way with me using a strap on dildo if I agreed to that. "Your chastity belt is a bit loose. Let me show you this neat feature." She took out a special tool and inserted it into the back of the belt. I felt her turn it and the belt got tighter. "The waist band adjusts, so as your waist shrinks, I can adjust it for you. Let's finish getting you dressed and get to work." She had me put on the bra with the inserts and a white silk blouse that had a high, lacy neck and a blue woman's suit that matched the shoes perfectly. The suit had a skirt that came down almost to my knees. Kathleen had me do my makeup myself. I was definitely getting better with it. When I was finishing, she came up behind me with a blonde wig. She pinned it to my real hair. "No more haircuts for you for a while. Look in the mirror and tell me that is a man," she stated. I had to agree that she was right. She took me by the hand and had me stand in front of a full length mirror. "Look at yourself." I saw a nice looking professionally dressed blonde woman. She had a very narrow waist. She was standing with her feet together in a pair of very high heels. "Damn, I guess you are right. I never would have thought that it was possible," I said in my male voice. "We need to start working on your voice next. You have made huge progress in just a few days." She hugged me. "Now, go make us some breakfast. I'm starving." She still had me eating smaller portions of food, which was good since my stomach was greatly compressed. We did not speak much during breakfast as we both seemed lost in thought. My mind kept shifting back and forth between work and Kathleen. After breakfast, I cleaned up the kitchen and went into the sewing room. I brought cups of coffee for both of us. I sat down at the desk, turned on my laptop and connected to my work over VPN. I worked for a couple of hours and decided I needed to take a break. I went to get us some more coffee. When I returned, Kathleen was hunched over her sewing table working on a design. I massaged her shoulders and neck. She leaned forward so that I could reach her upper back. "Ohhh, that feels really good. You can do that any time." After a few minutes, her muscles had relaxed a bit. I gave her a kiss on the neck and went back to work. Things were busy at work, so I was a bit startled when I heard her say, "Let's take a break for lunch." She handed me a purse that matched my dress. "I put your license and personal things in there. We're going out to lunch, my treat." She put an elastic choker around my neck to hide my Adam's apple, then took me by the hand and pulled me out the front door before I could protest. The door to her apartment was locked, and I was outside dressed as a woman. "Don't worry. I'll do all the talking. You will do fine. Just remember how to walk and move like a woman." She took me by the hand and pulled me toward the stairs. My apartment door was right there. If I could just get in there for some of my clothing... but I knew that would spoil things. I had to take the stairs slowly because of the heels and the cuffs. It took me a couple of stairs to figure it out. By the time we got to the bottom, I had it down pretty well. We went to her car, and she opened the passenger door for me. "Smooth the back of your skirt when you sit down and keep your knees together. Once you are seated, you can swing your legs into the car, but keep your knees together." I did as she instructed and did not flash her. She closed my door and got in on the driver's side. She took me to a chain restaurant that was crowded with business people taking their lunch break. I was extremely nervous, but things went without a hitch. We even went to the ladies room to use the toilet and freshen our make up. I was petrified the whole time. I did not relax until we were back in her car headed to the apartment. "Did you notice those guys staring at us?" she asked. "NO! That's awful!!" "The women were giving you catty looks and saying things about your shoes and waist. I think they were all just jealous." "You don't think anyone figured out I was a guy did you?" She just laughed. "Every guy in the place was ogling you. Every woman was making catty comments. I think you passed your first test on the outside." I was glad to get back to the safety and privacy of her apartment. It was also a nice treat not to have to fix lunch and clean up afterward. I thanked Kathleen for taking me to lunch. We worked the rest of the afternoon without talking too much. She did ask me to look at a few things she was doing and give her my opinion. I was surprised that she agreed with some of the suggestions I made. A little after five, we wrapped things up for the day. I made dinner and we ate and talked about the day. "After dinner, we need to go to the grocery store and do some shopping. We will do it together, but next week, I might send you out alone. I ordered some material that will help you learn how to sound like a woman. It should be here in a day or two." After dinner, Kathleen helped me to clean up, and then we went to the grocery store. I was a little concerned because it was the same grocery store where I usually shopped. I hoped nobody recognized me. I was more observant of people's reactions to us this time. I did catch both men and women staring at us. It was actually kind of fun and a bit of a turn on to know that people found us attractive. I had never had that happen to me before. It was challenging to carry the groceries up the stairs while wearing the heels and the thigh bands. It took a couple of trips up and down the stairs to get everything unloaded. Once the groceries were put away, it was time to work on Mary Ann's wedding dress. Kathleen sent me to her bedroom to remove the suit and blouse. I hung them up in the closet. I took off the blue pumps and put on the white ones. I don't know why I did it, it just felt right. I went back into the sewing room wearing the corset, bra and white pumps. "Why did you change your shoes?" she asked. "I thought it would look funny to have blue shoes under a white wedding dress." This made her smile. In short order, she had the petticoats and dress on me. She helped me up onto the platform after putting the collar and cuffs on me. She tied my ankles together and warned me to keep my balance and not lock my knees. She told me some more about her projects while she worked. She would also be making the dresses for Mary Ann's bridesmaids once she was done with the wedding dress. She worked for a few hours and then said it was time to stop for the night. Before she removed the dress, she put a full length mirror in front of me and had me look at myself in it. With the wig and