One Step At A Time free porn video

One step at a time I had always been interested in studying martial arts. I found a school near my home and signed up. The instructor and many of the students were ladies. I thought this would be a great opportunity to meet a lady who was athletic and interested in staying that way. I wasn?t disappointed. When practicing our punches and kicks, I was paired up with another student who had just started. Erin is a few inches taller than me. She has a pretty face and usually wears almost no make up. Her bright green eyes and clear pale skin go perfectly with her long red hair. It was hard to stay focused while working with her. When I touched her, there was a pleasant shock which we both felt. After the first class, she asked me to go to dinner with her. We took her car, a very nice Mercedes, to a nearby restaurant. I don?t even remember what we ate. I found out that she was single and had her own real estate firm. After dinner she took me by her home instead of back to pick up my car. She had a large house in an exclusive neighborhood. We pulled into her garage and she led me into the house. She gave me a quick tour and then had me pour some wine while she changed out of her work clothes. My mind was really spinning. This lady was obviously very rich and absolutely gorgeous. What could she possibly see in me? I?m not much to look at. I?m thin and not very tall. Most women don?t even give me a second thought. I was lost in thought when she came up behind me and wrapped her arms around my waist. I almost jumped out of my skin. I turned around and she pulled me close and gave me a quick kiss on the mouth. She held me at arm?s length and smiled. She was so beautiful, she took my breath away. She had piled her red hair on top of her head, which made her look even taller. She was wearing a black silk robe tied around her waist. She had sheer black hose on her legs and black patent leather pumps. "Well, how do I look?" she teased. I just stood there taking it all in. "Cat got your tongue?" I finally managed to say, "Wow." She smiled and sat on the couch. "Where's the wine?" "I'll get it." I almost ran to get it for her. I brought our glasses back and handed hers to her. "Sit next to me. I don't bite." I sat down next to her and took a sip of wine and then set down my glass. "Aren't you going to make a move on me, or do I need to do this?" She pushed me down onto the couch and climbed on top of me and started tickling me. I am very, very ticklish. She quickly had me reduced to a helpless, giggling, turned on, lump. She pinned me with her weight and gave me brief periods of respite so that I could catch my breath. She wore a musky perfume that combined with everything else really turned me on. I tried to push her off, but as soon as I did, she renewed her assault. "Ask for mercy, if you want me to stop." "Mercy, mercy," I managed to say. She leaned down and kissed me. Her tongue invaded my mouth and she stroked my very erect penis through my pants. "It looks like somebody enjoys being tickled." "No, please stop, I beg you." "What will you give me in return if I stop?" she asked playfully. "Name it." "I'll tell you what I want later, but right now you better get off this couch and up to my bedroom in the next thirty seconds if you know what is good for you," she said with a twinkle in her eye. She pushed herself off of me and helped me to stand. She took me by the hand and led me upstairs to her bedroom. I followed her up the stairs breathing in her musky perfume and staring at her legs and bottom. I couldn't believe how lucky I had become. She took off her black silk robe revealing black stockings, garter belt, panties and bra. She looked so hot standing there I almost came in my pants. "Close your mouth, stop drooling and get undressed" she commanded. She was breathing hard. I fumbled with the buttons on my shirt. Apparently I was taking too long because she just ripped it open and sent all the buttons flying. She pulled the shirt off while I was working on my pants. I managed to get my belt undone and my pants unfastened when she gave me a hard push back onto her bed. She yanked off my shoes, socks and pants so that I was completely naked and flat on my back. My erection was pointing straight up at the ceiling. "Yuck, you sure are hairy. Let's take care of that. Go into my bathroom and wait for me." "Are you serious?" "Do you want to stay with me tonight?" she said with her hands on her hips and one eye brow raised. She had her answer when I was standing in her bathroom a few seconds later. "Stand still, while I put this cream on your skin." It didn't smell very good, but it felt great having her hands all over my body. She rubbed it from my beard line all the way down to my toes. "Just stand there for a few minutes while the cream works its magic." She left me standing there thinking about her and wondering what she had against body hair. A few minutes later she returned with some towels. "Stand on this one, and use these to wipe the cream off your skin. As we wiped, my hair came off in big wads. When we were done, I was as bald as a pre-pubescent. She felt my smooth face and body and said, "Mmmm no whiskers or nasty old hair. Jump in the shower and use my shampoo, cream rinse and body wash." I took a hot shower and washed as quickly and thoroughly as I could. When I was done, she was waiting for me with a big, soft, fluffy towel to dry me off. "I love how you look with no hair. It is so sexy. Don't you agree?" I looked in the mirror and saw my thin, naked body in the mirror with her standing behind me. She looked really hot. "I love how pretty you smell with my shampoo and body wash. It makes me want you." She took me by the hand and led me to her bed and had me lie down. She climbed on top of me. I reached my hands up to her waist and she kissed me again. She pressed her silky bra covered breasts against my chest and moved them around. She rubbed her stocking clad legs up and down my smooth legs. It felt wonderful. She collapsed on top of me and pinned me with her weight. She began tickling me again. I struggled to get away, but she was too good. There was no escaping. I kept begging her to stop but hoping she would continue. "Do you really want me to stop?" she asked with her face inches from mine and her eyes penetrating me. "Yes and no. It is incredibly frustrating and also a powerful turn on." She smiled and continued her assault on me. I finally begged for mercy. She stopped and said that if I begged for mercy, than I would have to do something for her. I said, "Name it, just please stop tickling me. I can't take it any more." "Put your hands over your head and hold onto the head board." I did. She reached under a pillow and pulled out a silk scarf which she used to blindfold me. Then she shifted her weight and pinned my arms and shoulders with all of her weight. Her crotch was inches from my mouth. I could smell her sex, and it smelled great. While I was thinking about that, I felt her handcuff my wrists to the headboard. I tried to move my hands to escape, but I was caught. "Oh crap," I said out loud. "Oh crap is right. You are at my tender mercy now. Do you want to lick me?" "I'd love too." Without taking off her panties, she lowered herself onto my mouth and grabbed the hair on my head with one hand to guide my tongue. She was extremely wet before I even started. I heard and heard her panting and moaning and pushing herself down on me even more. It didn't take her long to shudder and relax for a minute. I took the opportunity to relax my jaw and tongue. "Don't think you're done yet," she said and sat on my mouth again. She pulled her panties aside and gave me better access to her. She used my hair to steer my tongue and told me what she wanted me to do. She came again quickly. "You are a natural pussy licker. Your tongue feels so good on me." I have no idea how long I spent licking her. I lost track of how many times she came. My tongue and jaw ached when she was finally sated. She got off of me and said, "Your poor willy has been hard for hours. Let's see if we can do something about that." She adjusted my blindfold and retied it. I felt her on the bed next to me. I gasped as she licked the tip of my penis. "Oooh, you are so sensitive. Would you like to come?" "Yes, please," I begged. She tickled up and down the length of my penis with her finger nails causing me to moan and groan. When I got close to exploding, she would stop. It was maddening. "Please stop tickling and let me cum," I begged. "What is it worth to you?" "Name it, I'll do anything, just please let me cum tonight." "Well since you asked so nicely, I want you to wear something special to work tomorrow." "OK, no problem," I answered eagerly. She used her mouth and her hand on me to bring me to an earth shattering orgasm. I felt like I pumped a gallon of sperm into her mouth. I lay there with my head buzzing while she continued to lick me. She got off the bed and left the room for a few minutes. I tried to get out of the handcuffs, but it was no use. I waited patiently for her to return. I heard her rummaging through her drawers and then I felt her putting something silky over my feet and ankles and pulling it up my legs. It felt great on my bare legs. "Lift up your bottom." I did, and she tucked my penis into what I knew had to be a pair of silky panties. She unlocked the handcuffs but said, "don't remove your blindfold until I tell you that you can." I rubbed my wrists and sat up. She had me raise my hands over my head. I felt something smooth and silky pulled down over my body. She ran her hands all over my body. "Doesn't it feel divine?" I just nodded my head as the erotic sensations coursed through my body. She stood me up and untied the blindfold. We were both wearing matching silk nightgowns. Mine was white and hers was black. "We're both exhausted, let's go to sleep." We cleaned up a bit and then climbed into bed. She rolled me on my side and then snuggled in behind me putting her arm over me and holding my penis possessively. I woke up the next morning to the feeling of her rolling me on my back and climbing on top of me. The feeling of the silk nightgown against my skin and this beautiful woman grinding herself on top of me was fantastic. "Good morning sleep head," she said smiling. "I see you're 'up' finally." She climbed off of me and said it was time to get up and go to work. We undressed and got into her oversized showed. I washed her hair and body. This gave me another raging hard on. When I was done washing her, she returned the favor. We dried each other off and stepped out of the shower. She handed me a pair of silky pink panties and told me to put them on. "I can't wear these to work," I complained. "And why not? Who is going to see them? It will make you think about me all day, and let you know that I'll be thinking about you too. Besides, they are going to feel great against your smooth skin. I better not find out that you took them off either, or you'll face another round of tickling." "OK, OK, I'll wear them." I was still hard and had to push my erection down to get it to fit. I pulled my socks and pants up. "What am I supposed to do for a shirt?" She dug through her closet and found a blue button down shirt that fit, although it was awkward to put on since the buttons were on the wrong side. I made us some breakfast while Erin was getting ready. She came downstairs looking like a million bucks in a tailor fit pants suit with matching high heels. "I could get used to having someone cook me breakfast and make coffee." We ate breakfast and I cleaned up while she read through some of her e-mail. She took me back to my car so I could go to work. "I'll call you later," she said and drove off. I had just enough time to go straight to work without being late. I wanted to go home and change my shirt, but I didn't have enough time. I was fairly self conscious wearing a woman's shirt and panties under my clothing. I had trouble concentrating on my work. I kept thinking about Erin. She called me later and asked me how I was doing. She invited me to dinner at her house that night. How could I resist? After work, I went home and grabbed a change of clothes, my toothbrush and put them in an over night bag. I got to Erin's house right as she was pulling into her driveway. She had me pull my car into her garage. She gave me a hug and a kiss as a greeting. She put her hands down my pants. "Just making sure you're still wearing your panties. I like that shirt on you. You can keep it too," she said with a smile. "Thanks, but I think they'd both look better on you." "We'll see about that. Can you make us some drinks while I get out of my work clothes?" She headed upstairs. A few minutes later she called down to me. "Can you bring my drink up here?" I brought her drink up to her. She was wearing her short black silk robe, high heels and stockings. I hoped she was wearing a garter belt and not pantyhose. She sat down in a big padded chair and held her foot out to me. "Will you be a dear and rub my feet for me? Wearing these heels all day can be a real pain." I handed her drink to her and knelt down in front of her and began rubbing her foot. She took her other foot and found my penis and began rubbing me through my pants with her toes. She closed her eyes and enjoyed the massage. After about 15 minutes she switched feet. The foot rub felt great, but wasn't enough stimulation to bring me over the edge. When she was satisfied with the foot rub, she crooked her finger at me to come closer. When I got closer, she leaned forward and kissed me on the lips and asked, "Will you lick me down there? I've been so horny all day thinking about you wearing my panties and shirt." Without waiting for an answer, she scooted to the edge of the chair, wrapped her legs over my shoulders and pulled me into her crotch. She was extremely wet. Her musky smell was overwhelming and wonderful. She held my head with both hands and guided my tongue where it would do the most good. Her legs were wrapped so tightly around my head that I could hear her talking but couldn't understand what she was saying. It did not take her long to have an orgasm. She squeezed my head so tightly that I thought it might pop. She released my head and I sat back on my heels. She looked beautiful in her garter belt, stockings and panties. Her face was flushed and she was pinching her nipples through her bra. "That was nice. I think I'll call out for Chinese so that we don't have to do any dishes." "Sounds good to me," I said with a smile. "Go wash your face and take off those clothes." She ordered the food while I got cleaned up and washed off. "Brush your teeth and gargle with the mouth wash too. Go to the bathroom too because you might not get another chance for a while." I got cleaned up and undressed and stood naked in front of her. My penis was pointing at her. "Put on the lingerie that I laid out for you on the bed." I looked on the bed and there was a pink camisole, panties, garter belt and stockings. They looked like they were made of silk. "Are you serious? That stuff is for women, not men." "How can you say that? Didn't it feel wonderful to wear my panties today?" I looked at my feet embarrassed. "Yes." "Then put them on." "But..." I wanted to wear them, but I didn't want her to know that I did. "You can put them on or I can tickle you until you agree to wear them." "But..." she started toward me with her fingers making tickling motions. "OK, OK. Can you help me put them on?" "I will this first time, but after this, you'll have to do it yourself." "After today?" "Yes, after today." She stared me down. I knew that if I wanted to stay with her I would be wearing her lingerie. It was a powerful turn on for both of us. I pulled the pink camisole over my head and felt the thin straps on my shoulders. That felt strange. "Put on the garter belt next." I put it on and fastened it around my waist and fastened the little hooks. She looked at me approvingly. "Stockings next." She showed me how to roll them up, point my toe and pull them carefully up my legs and fasten them to the garters. I repeated it for the second leg. I pulled the panties up my legs without having to be told. I looked up at her and she had a stern look of approval that turned to one of sexual hunger. "There, that wasn't so hard was it? Well, I can see that something is still hard. You can pretend that you don't like the lingerie, but your penis doesn't lie." I felt my face turn red with shame. "Aww your blushing and embarrassed. That's cute. Don't worry, I think you look hot and that's all that matters." She pulled me close and kissed me. She rubbed her stocking covered legs on mine. The sheer stockings rubbing against each other felt wonderful. She rubbed her hands all over me, but only where I was wearing lingerie. She didn't touch my bare skin. I touched her through her lingerie too. She was so gorgeous and sexy. She pushed me down onto the bed on my back and climbed on top of me and started to tickle me. "No, no please stop" I pleaded. I tried to tickle her back, but it was no use. She wasn't ticklish. She kept up her assault on me. I tried to push her off me, but the tickling drained my strength. She pinned my arms to the bed and sat on my chest. She pulled some leather cuffs from behind the bed and quickly had my hands secured to the head board. She got off the bed and pulled me down toward the end of the bed as far as she could. She put leather cuffs on my ankles and secured me spread eagle on her bed. "Hmm, what can we do while we wait for the food? I have a great idea. Why don't I tickle you?" "No!!" I shouted as she ran her finger nails up the soles of my feet. She concentrated on my feet for a long time until I was finally given some respite by the doorbell. She put on her robe and went down to get our food. She came back up with the food. "Would you like to eat, or play some more?" "Eat please," I begged. "I hoped you'd say that." She climbed on my chest and sat on my face. I licked her for all I was worth. "You're starting to know how I like it." I did my best to please her. When she climaxed, she rested for a few minutes and then climbed off me and got the food. She fed me small bites while she ate. When she had enough she climbed on top of me and began kissing me and caressing me all over my body. My poor penis had turned purple. I was dry humping the air. She teased me for a long time. I was begging her to release me. She teased my penis with her tongue, fingertips, fingernails and she even blew on it. She would bring me almost to the edge and then stop. It was maddening. Why did I let her tie me down again? "Because you love every minute of it," my brain answered me. After two hours of teasing me, she finally stopped. "If I let you cum, will you wear something pretty to work tomorrow?" "Yes, yes, anything you say," I heard myself say. "Will you wear them the rest of the week if I ask you?" "Yes, yes, yes!" "Will you wear them every day until I say you can stop?" "Yes!!!" "Yes what?" "I will wear your panties every day until you tell me I can stop?" "That's not what I had in mind. Will you wear stockings, garter belt, camisole and panties every day?" "Yes, I'll wear them!!!" "You have to tell me what you'll wear." She was looking me in the eyes like a lioness at her prey. She was tickling the underside of my penis with her fingernail. "Yes, I'll wear a garter belt, stockings, panties and camisole every day until you tell me to stop!" "Oooh, that will make me so happy." She took me into her mouth and pumped with her hand while she massaged my balls. I soon blew my load into her mouth. She swallowed it all and then lay down on top of me. "Erin, when are you going to let me make love to you?" "Not any time soon. You have to earn that privilege." I must have fallen asleep because I awoke a long time later to the feeling of Erin releasing me from my bonds. It felt good to bend my arms and legs. Erin rolled me on my stomach and gave me a wonderful massage. I was soon fast asleep again. I woke up to the sound of her alarm blaring. We got up, undressed and jumped in the shower. We washed each other and then dried each other. She laid out my lingerie for the day. I didn't argue with her. When I had put on the pretty pink and white lingerie, she kissed me and ran her hands over me. I went down to the garage and retrieved my over night bag so that I could wear my male outer clothes. When I was dressed, I made coffee the way Erin liked it and brought it up to her. "Mmm, you're spoiling me. I just might keep you here as my maid." "I don't think I'd look very good in a dress, and I don't speak French." "Maybe we'll see about that," she said as I went back downstairs to finish making breakfast. We ate breakfast and I cleaned up while she read the morning paper. As I kissed her good bye, she said, "Don't forget that we have class tonight. Don't be late." She ran her hands up and down my pants and gave the garters a little snap. "I hope you'll be thinking about me today." "I don't think that will be a problem. Can I come over again after class?" "You'd better," she said with a smile. Work dragged on and on, but every time I moved my legs or got up, I couldn't help but feel the luxurious feeling of the lingerie. It kept me in a simmering state all day. I spoke with Erin a couple of times during the day. Finally, it was time to head out for the day. I went to the bathroom and carefully removed all of the lingerie except the panties and put on my martial arts uniform. It felt funny to walk out to my car wearing it, but at least I wouldn't have to change into it and have everybody see me in my lingerie at the school. Erin smiled at me when I walked in. She gave me a hug and gave me an inquisitive look as if to say, "You better be wearing the lingerie under there." I just shrugged my shoulders and smiled. We had a good work out and learned some new stuff that we were supposed to practice over the next few days. Our instructor told us that we were going to compete the next session to see who had learned things the best. The top performer would get a prize. I walked out with Erin. She gave me a peck on the cheek and said to follow her home. When we got there, she pulled my uniform off and said, "What are you wearing, or should I say, what are you NOT wearing?" I just stood there and looked at her dumbfounded. "Didn't you promise to wear the lingerie every day?" "Yes, but I didn't know that meant I had to wear it to class. People would notice. You don't wear that stuff to class." "I know, but did you at least ask me?" "No. I didn't know that I need to ask you." "When you make a promise, you should keep it, don't you think?" "Yes. Bur I didn't think that I was breaking the promise. I'm sorry." "It's OK, but you owe me. Let's go take a shower and then make some dinner." We got cleaned up and as we were getting dressed into our matching negligees, she said, "I want to make you a little wager." "What's that?" "If I do better than you on our next test in class, then you have to do something more for me." "What if I do better than you?" "Then you don't have to wear the garter belt and stockings, unless you want to." "What if I lose?" "Then you will get a manicure and pedicure. You'll have to keep getting them weekly until you do better than me." "OK, I'll take your bet, and you're gonna regret, 'cause I'm the best there's ever been." She smiled and we shook hands. "That's a bet." She had me dressed in stockings and garter belt under the negligee. "I don't want you to get a run in your stockings, so I bought you some shoes to wear with them. What do you think?" She handed me a shoe box. I opened it. Inside was a pair of black patent leather pumps with what had to be three inch heels. "Put them on so I can see how you look in them. Go on, don't be a baby. You know you want to wear them." The truth was that she was right. What was wrong with me? "Where are we going with this?" I asked. "I'm not sure, but I know I want you dressed as a woman as much as possible. It turns me on so much. I know it is the same for you. It is powerful for both of us. Put the shoes on." I put them on the floor and stepped into them. They fit perfectly. I could feel the pressure on the back of my calves and my toes were pushed into the toe of the shoes. "They look great. Let me put my shoes on and we'll go downstairs." For the first time I was able to look at her eye to eye. She kissed me and then stepped into a matching pair of shoes and was taller than me again. "I want you to learn how to cook for me. I will show you the basics. When you get better, I would like you to take some cooking classes. Would you do that for me?" "Yes." "Good." She took me by the hand and led me downstairs. She gave me some pointers on walking in the heels. It was awkward at first, but I got better as the night wore on. We made dinner together and then ate. After dinner she left me to clean up while she checked her e-mails and returned some phone calls. When I was finished cleaning the kitchen, I brought her a glass of wine. She was on a conference call and brought her finger to her lip to tell me to be silent. She waved me over to her and had me turn around. She pulled my hands behind me and then secured them with a short piece of soft rope. I tried to get them loose, but she had them tied too tightly. She had me kneel in front of her and then she wrapped her legs over my shoulders and pulled my mouth to her crotch. I knew what to do. I went to work immediately trying to make her moan. She put the phone on mute and tried to concentrate while I did my best to distract her. She had to pull my head away and scoot back in the chair several times so that she could talk. When she was done talking, she would scoot back to the edge of the chair and pull me in tight again. As the call ended and she said good bye, I could tell her voice was strained a bit. She hung up the phone and pulled me in tight. It did not take long for her to have an intense orgasm. When she had calmed down, she parted her legs and let me lean back. I gave her a big grin. It was fun trying to make her orgasm on the call. She had me stand up so that she could untie my hands. "Go wash your face and bring back something to clean my chair." I did as I was told and had everything cleaned up. We sat on the couch and made out while we watched TV. She kept me nice and hard the whole evening without letting me cum. Around 11, we went upstairs and got cleaned up for bed. She used the leather cuffs to tie me up spread eagle again. She got out a feather duster and told me I looked dusty. I pleaded with her to stop, but it was no use. She tickled me without mercy alternating between the feather duster, her fingers and her fingernails. When I finally begged for mercy, she smiled at me and said, "From now on, I want you to wear high heels when you are here. Is that clear?" "Yes, when I am here, I will wear high heels. No questions asked." "Good." With that she turned around and sat on my face so that I could lick her to orgasm. She teased my poor penis while I pleased her. After several orgasms, she took my penis into her mouth and pumped me to climax. It felt really good. After a few minutes she unbuckled the cuffs and let me stretch my arms. The weekend came, and Erin kept me in lingerie the whole time. We never left the house. I was exhausted by Sunday evening from all of our sexual activities. The next week we had our Martial Arts class. I had not practiced at all. Erin did much better than I did. She gave me a wink as if to say, "you owe me big buster." I was a little bit afraid of what the terms of the bet would be. After work the next day, she had me stop by her office. There was a girl in her office finishing up her nails. Erin told me to close the door and take off my pants, and stockings. I was totally embarrassed. The girl's name was Susie and she worked at a shop in the same building. Erin had Susie give me a full pedicure and manicure. Susie was an expert. Erin had her paint my toenails a bright red, but she had her use clear polish on my finger nails. I knew I would have to be careful at work so that nobody noticed them. My fingers and toes had never looked better. When the paint was dry, Erin had me put my stockings and pants back on. I paid Susie and gave her a big tip. I hoped that would buy her silence. The next week I lost the bet again, but we had not agreed on the terms. When we got to her house, she said, "You lost the bet. Do you want to know what your payment will be?" "I'm afraid to ask," I said truthfully. "I was thinking that you should have to wear a skirt or high heels full time from now on, but that might be a bit rough for you at your current job. I'll give you a choice. You can either wear a locking collar or a chastity belt. Which one will it be?" "Can I see them before I make up my mind?" "I suppose that would be fair." She took me by the hand and led me upstairs. "Your choice, but know that neither one will come off for a long time." "Why do I have to wear either one?" "You accepted the bet. Think of it this way. One of the choices will be hidden from view. The other will be plain to see. We can bet again for next week. If you do better than me, then you can lose the belt or collar, which ever one you choose. But if I win, you'll be making another choice. I'll do the same thing. You'll be able to wear one choice under your clothes, but the other will be obvious. Which will it be? A collar that everyone can see or a chastity belt that only I'll be able to see? As I said before, neither will come off for a long time, so be careful with your choice." "Can I try them on and see whether they can be hidden under my regular clothes?" "Once they are on, they are on until I choose to unlock you or you do better than me in class. Change out of your work clothes and think about it." "This is a big decision, can I think about it over night?" "Nope. You have ten minutes. After that, they will both go on." I fit the collar around my neck to see if it could be hidden by a shirt. It was fairly tight. I would have to wear a shirt and tie to get away with wearing it. It looked like something a woman would wear, only much tighter. It was an agonizing decision. I knew that I wouldn't come for a long time if I chose the chastity belt. On the other hand, I would get a lot of questions at work if I chose the collar. I needed the job. Reluctantly, I chose the chastity belt. With a smile on her face, she helped me put it on. I removed my panties, stepped into it and pulled the belt up around my waist. For some reason, this act of submission gave me a raging hard on. There is no way I was going to fit into the penis tube. Erin told me to lie down on the bed. She hiked up her skirt and sat on my face. I licked her wet pussy through her panties while she gave me an amazing blow job. It took me almost no time to blow my load. As soon as I had shrunk down enough, I felt her slide my penis into the tube. She connected it to the front of the belt and brought the ends of the belt together along with the front face plate. With no hesitation at all, she locked it shut. It only took her a few seconds more to have a shuddering orgasm. She collapsed on top of me. I lay there for a while wondering what the heck I had just done. We changed into our lingerie and went downstairs to make dinner. Erin brushed against me repeatedly. It felt very strange to not be able to touch myself at all. All I could feel was steel. She was doing her best to arouse me, and it was working. I could feel my penis straining against the steel tube. We made a light dinner. While we ate, Erin ran her toes up and down my stocking clad legs and pressed her toes into my chastity belt. She gave me a devilish grin. "When are you going to let me out of this thing?" I asked. "I told you it would be a long time. If you pester me about it, it will only increase the length of your sentence. I'd suggest you strive to please me in every way possible. I have heard that a man who is locked up for a month or two will do absolutely anything to gain some relief." "A month or two?" I asked incredulously. "Maybe," she said with a grin. "Any chance of early release for good behavior?" "Good behavior? No. Exceptional behavior on the other hand might help." "What would be exceptional behavior?" "You could help me around the house a bit more. Maybe you would like to wear a dress and be my maid. That might be considered above and beyond." We ate the rest of our dinner in silence. We were both deep in thought about where we were going with this. Erin went to her office to do some work while I cleaned up after dinner. I brought her a glass of wine and asked her if I could massage her feet. She smiled and pointed under her desk. I crawled under there and went to work massaging her feet while she made some phone calls and finished her work. When she was done, she grabbed me by the hair and pulled my face into her crotch. I used my tongue and lips to please her. When she was satisfied, I got up and cleaned my face and got a warm wash cloth to clean her and her chair. She took me by the hand and led me up to her bedroom. She lay me down on my back. This belt of yours has a great feature for me. Let me show it to you. She took a dildo out of her bedside table and attached it to the front of my belt. She gave it a turn at the base and it began vibrating. She looked me in the eyes. Hers were filled with lust. She mounted the dildo and pleasured herself on top of me. She leaned over so that I could lick her nipples and run my hands over her. This is the first time that I had not been tied to her bed. She went wild screwing herself on me. I got absolutely no pleasure out of it, just more frustration. She had a screaming orgasm and collapsed on top of me. "I've been needing a good hard fuck for a while," she said. "Why wouldn't you let me do it for you?" "I told you that you have to earn it first." "I guess I should have asked how I could do that." "If you had given me ten orgasms without asking me to get you off, I would have let you in, but you were too focused on getting that immediate relief. Now you can focus on my needs for a while. All you had to do was ask." "Crap. The way you tied me to the bed and teased me, I don't think I could have ever done that." "Maybe I'll let you have on orgasm for every one hundred that I have. I'm tired, let's go to sleep." I learned that I had to sit down to pee while wearing the belt. It was hard to get all of the urine out. Sometimes it would drain out a little after I had pulled up my panties. Erin made me start wearing sanitary pads in my panties. I had to change them every time I went to the bathroom, which meant I had to keep several in my pockets at work. Work the next day dragged by. My boss called me into his office at the end of the day and asked me what was going on. My work performance was way down. He asked if I needed to take some time off to recharge my batteries. I told him that I had a lot going on outside of work and that I would like to take a weeks vacation to deal with it. That night when I got to Erin's she kissed me and told me to go upstairs to her room and change out of my work clothes. She was still dressed in her business suit. On her bed was a short black dress, with matching black lingerie. There was a black slip, stockings, panties, bra and a garter belt with a waist cincher built in. I took off all of my clothes and the lingerie I wore to work. I put on the stockings first and then the waist cincher. It was made from a stretchy elastic material. It has a zipper in front and some strings to pull it in some more in back. I pulled it as tight as I could and tied it off. It drew my waist in a couple inches. I clipped the stockings to the garters that hung down from it. The panties were next. I put on the bra. It had padding built into it that made it look like I had breasts. I pulled the slip over my head and let it float down. It felt really good putting on all this lingerie. My penis strained against its steel prison. When I picked the dress up off the bed, I noticed there was something white underneath it. I picked up the white thing and discovered a small lacy apron. I put the dress on over my head. It was really difficult to pull up the zipper in the back, but I managed. It was tight at the waist. I would never have been able to zip it up without the waist cincher. I looked at the apron for a few moments. I finally picked it up and tied it around my waist. The bottom of the dress came down to just above my knees. The last item on the bed was a shoe box. I opened it up and found a new pair of black patent leather pumps. The stiletto heel was at least four inches high. I put them on carefully, and turned to see what I looked like in the mirror. As I turned, I noticed Erin standing in the door way watching me get dressed. She had a big smile on her face. I looked at myself in the mirror and from the neck down I looked like a maid. She walked up to me and put her hands on my waist. "I love how that cincher pulls in your waist. That dress looks great on you. Turn around so I can see how it looks from behind." I turned around and she stopped me when I was facing away from her. She put her arms around my waist and hugged me from behind. She put her head on my shoulder and whispered in my ear, "I want to own you." She pressed her pelvis tightly into my bottom and pulled me tightly against her. She took me by the hand and led me to here dresser. She took out some perfume and applied it to my wrists, neck and behind my knee. It smelled wonderful, and now there was no way I could get away from it. She kissed me and said, "Go downstairs and make us some dinner before I throw you down on the bed and ravage you." I did as I was told and hurried out of the room, down the stairs and into the kitchen. I had to move carefully in the new higher heels. I made dinner and served it to her. She had me remove the apron before I sat down to dinner with her. "So how do you like wearing a dress?" I looked down embarrassed and could feel her green eyes piercing me to my soul. There was no choice but to tell the truth. I looked up and said, "I like how it feels. The opening on the bottom makes me feel vulnerable. I like the compression of the waist cincher and the lingerie feels great against my skin." I could feel my face turning red with embarrassment, but I knew better than to lie. "I will help you to learn how to walk and move so that you look more natural, although you are doing well on your own. I noticed you smoothed the skirt of your dress before you sat down. That was very lady like. You are doing a good job keeping your knees together as well. I don't want you getting your hair cut until I tell you to, is that understood?" "Yes." "Good. You did a nice job on dinner tonight. I really enjoy having you here with me. I want you to move in with me. You will terminate the lease on your apartment and we will figure out where to put all of your stuff. You spend most of your time here, and it seems silly to keep your place." This was stated as a directive rather than seeking any input from me. She looked at me and waited for a response. "I'd love to move in with you, but this is kind of sudden. We've only known each other for a short time. Are you sure about this?" "Absolutely. Tomorrow after work we will go over to your apartment and pack up all of your clothes and bring them over here. You can give your landlord notice at that time too. I have some work I need to do. After you clean up the dishes, please bring me a cup of tea." With that she got up from the table and left. I put the apron back on and did a thorough job cleaning the kitchen. I knew when I brought her tea that I would spend the rest of the night in severe frustration while I serviced her. I waited until I could no longer delay the inevitable. I brought her tea into her. Erin had me place the tea on her desk and turn around. She untied my apron strings retied it more tightly and then tied my hands behind my back with the extra strings. I got down on my knees and worked my way under her desk. Fortunately for me, the floor had thick, plush carpeting, so it was not too hard on my knees. As expected, she wrapped her legs over my shoulder and I pleased her while she finished her work for the evening. She helped me get out from under her desk and untied my hands. We went upstairs and got ready for bed. Erin had me undress her and put her night gown on her. She picked out a pink silk baby doll nightgown for me. She spooned me from behind with her hand cupped over the chastity belt. She was asleep right away. It took me a long time to go to sleep in my frustrated state. After work the next day, we met at my apartment. Erin found the trash bags and threw all of my underwear, undershirts, shorts and t-shirts into trash bags. "We will drop these off at Good Will. You won't need any of them." "But, but, but..." I started to protest. "As long as you are living with me, you won't be wearing any of that rough boy underwear or lounging around looking like a slob. If you want to discuss it any further, I will consider that rude behavior." She tapped the front of my pants right on the chastity belt. I caved in and looked down at my feet. "Go get your work clothes and shoes and put them in a suitcase so we can go turn in your notice." I did as she asked and hauled the stuff down to my car. We walked over to the office so that I could turn in my notice. Erin had a piece of paper typed up for me already. I just had to sign it. As we walked back to our cars she said, "Let's go out to dinner to celebrate. After that we can do a little shopping before we go home." At least I didn't have to cook and clean up dinner for her. Erin ordered for me because she said I needed to lose some weight. After dinner I followed her to the mall. She took me to Victoria's Secret. A sales girl approached and asked if she could help. Erin said, "I'm tired of him wearing my lingerie. Can you help him pick out his own camisoles, bras, panties, garter belts and stockings? Maybe some sexy nightgowns too." I was so embarrassed I almost hit the floor. The sales girl giggled and then pulled out her tape measure to figure out what size I would need. We spent a long time picking out just the right things. I left with a loaded up credit card and a bunch of bags. We went shopping in a department store for slips, skirts, blouses, dresses and shoes. Erin did her best to embarrass me in each department. She made me take off my socks to try on some high heel pumps to go with my new clothes. The sales woman was impressed with my painted toe nails and stocking clad feet and ability to walk in heels. I was never so glad to leave the mall. We had so many bags that Erin had to help me carry them all. When we got to Erin's house, she had me hang all of the new clothes up in a spare bedroom. It was late and we were both tired. We got cleaned up and Erin had me wear one of my new night gowns to bed. I spent quite a while pleasing her with my mouth. When she was satisfied she said, "You're really getting good with your tongue. Maybe you don't ever need to be unlocked again. Wouldn't it be great if I kept you locked up forever?" I was so frustrated already that I started crying when she said this. "Erin, please don't do that. I'm so frustrated. I love you and want to be with you, but please don't do that to me. I'm a man and I need to have release once in a while." She put both hands on my face and wiped away my tears. "Don't cry sweetie. I'm just teasing you. If you are good, I will let you out of your belt once in a while." She kissed me passionately and rubbed her body against mine which only made me more frustrated. "We better go to sleep. We have class tomorrow, and I'm going to beat your ass again." With that she rolled over and was asleep almost immediately. I lay there for hours worrying about the test tomorrow and what my choices would be if I lost again. I had not had any time to practice the new things we had learned much less the old ones. I knew I was going to lose, and I was right. When we got home from our class, I knew what was coming and I didn't have to wait long. "OK, you have another choice to make. You can either wear my collar or you can wear a real, fully boned, lace up corset. If you are worried about being found out at work, the corset is definitely going to give you a more feminine shape. It is going to pull you in at the waist. If anybody pats you on the back or bumps into you, they are definitely going to feel it. You can probably disguise it if you wear a sweater or a blazer. You have ten minutes to decide." "Erin, how can you keep doing this? How am I going to keep my job? Where are we going with this? You already have me locked in a chastity belt and wearing women's underwear at work and dressed like a maid at home. Tell me what you want from me?" "I am in love with you, but I am the dominant one in this relationship. If you decide to stay with me you will be dressed as my girly man 24/7/365. I will always wear the pants and you will always be kept in skirts and dresses. I don't know if you are ready for that, so I have tried to take it slow. Unfortunately, I am very impatient. We've taken some big steps very quickly. Let's go upstairs and take a shower before you decide whether you want to wear my collar or the corsets. It really doesn't matter which you decide because if you stay with me, you will be wearing both before long." "But what about my job? What about my career? I don't think I want to be a full time maid." "You don't need to worry about your job. I looked into you finances. I know you don't have any debt, so that means you don't need any income. If you want a job where you can be challenged and nobody will care if you are wearing a dress, you can come to work for me. I'll help you earn your real estate license. I can definitely use the help. Besides, I've always wanted to screw the secretary." She pulled me to her and held me close. "Don't worry Baby, if you decide to stay with me I will take care of you." "OK," is all I could say as tears streaked down my face. Erin held me close and asked me why I was crying. "I don't know. This is so much to take in. Things are moving so fast, and it is all so new and strange. I'm scared and confused and really, really frustrated. You make me wear all this sexy lingerie which caresses and teases me all day long and then I get to lick you which I love doing, but frustrates me to no end. It has been a long time since I've had any release. I feel like I'm about to burst." "Let's go take a shower and you'll feel better." I followed her up the stairs and marveled at how such a beautiful and successful woman could be in love with me. We stripped off our work clothes and took a nice hot shower. I did feel better when we got out of the shower. Erin dusted me with some pretty smelling powder and then did the same to herself. "I'm going to order some Chinese food. Go into my closet and pull out the FedEx boxes you see in the back, but don't you dare open them." I did as directed while Erin ordered the food. I put the boxes on her bed. When she was done ordering the food she said, "OK, open them up." Inside the first box was something made out of thick white satin. When I pulled it out, I realized it was a corset. I laid it on the bed and it had a total of eight garters hanging from the bottom. It was obviously very well made and very pretty to look at. I held it up to get a better look at it. Inside the box there was also a white tube that felt like it was made of spandex. I took it out and figured that it must go against the skin to prevent the corset from rubbing and getting dirty. "What do you think?" Erin asked. "Gosh, it is very pretty. I hate to admit it, but I'd really like to try it on." This made Erin smile and she said, "There will be plenty of time for that later on. Go ahead and open the other boxes." The next box contained a light pink corset that looked like the same design as the white one. In the last box was a very plain white corset made out of cotton. It had no garters hanging down from it. "The first two are your day corsets. You will wear them all day. The last one is your night corset. You will wear that one to bed every night." "To bed? Every night? I have to wear a corset to bed?" "Of course dear. There's no point in wearing a corset all day only to have your waist expand during the night. You'll see that it will make your waist training easier." "Waist training?" "Yes, waist training. How are you going to be my girly man if you don't have a female shape? Pick one of the day corsets and we'll lace you in." "You're pretty good at the whole sales thing aren't you?" "You'll find out. Put the pink one on." I picked up the corset liner, stepped into it and then pulled it up my legs. Erin helped me make sure it was smooth. I pulled it up so that it was below my chest and just above the chastity belt which rested on my hips. I picked up the corset. It was fairly heavy. I loosened the strings so that I was able to fit it around my waist. The garters swung freely and tickled the tops of my thighs. I closed the front busk. Erin slowly pulled in the laces until the corset was snug. "Hold onto the bed post and let me get this a little tighter. We won't go too tight at first so the corset will mould to your body and your body will adapt to the compression." I felt her pull from the top to the middle and then from the bottom to the middle. She did this a couple of times until I felt I was being squeezed pretty hard, but it was not uncomfortable. "We'll just tie it off like that for now. Let me see you try to put on your stockings now." I tried to bend over to put them on, but the corset was way to stiff to allow me to bend over very much. "I had some extra strong stays put in, and had them spaced more closely so it would hold you nice and firm. I don't think I'll see you slouch while wearing them. How does it feel, do you like it?" "I like it." "I knew you would. Seeing you in it makes me really horny. Let's get your stockings on you. When you put this on tomorrow morning, you'll need to put your stockings on first." I sat on the bed and she helped me into the stockings. I clipped the garters to the stocking tops. She gave me some matching pink panties to put on. Erin handed me a bra to put on. She put some very realistic breast forms in them. I stood up and looked into the mirror. I definitely had a female shape. "Go sit down at my vanity." She began putting foundation on my face and then used mascara on my eyes, painted my lips and then finished with my cheeks. She made me close my eyes so that I could not see myself in the mirror. She went to her closet and came back with a shoulder length blonde wig. She put it on me and then brushed it out and adjusted it. "I think you'll agree that blonds have more fun. Take a look at yourself." I turned around to look at myself in the mirror. I could not believe it was really me. I looked so good. I put my hands up to my face to verify that it was me. "Don't touch!!!" she scolded. "Not until you know how to do it yourself. I just wanted to verify that I was right in my assessment of you. You would have made a very hot woman. Instead you make one hot girly man!!!" I still had not said anything. I just kept looking in the mirror. "Stand up and look at yourself in the full length mirror." "Wow. I can't believe that is me. You must have some sort of magical powers." "I paid the bills during college by selling makeup at a department store. I got plenty of practice. "Let me see you in one of your new outfits. Go pick out something pink." I practically ran to the spare bedroom and retrieved a pink slip and dress. I found a pair of pink pumps with 4 inch heels. I stepped into them so that I would not have to try to bend down. I hurried back to Erin's room so that she could help me get dressed. Erin helped me put on the slip and then the dress. She held me at arms length and then made me do walk around so she could check me out. I looked at myself in the mirror and thought I looked like a very attractive woman. Erin came up behind me and wrapped her arms around me. We looked like two very hot women standing there. She began nibbling on my ears, neck and shoulder. My penis was trying to do the impossible and split the steel penis tube. Erin turned me around and embraced me in a slow dance. I felt her grind her pelvis against mine. She whispered in my ear, "Girl you are making me so hot. I want to fuck you right now." She had me sit on the edge of the bed and hiked up the skirt of my dress. She pulled down my panties and attached the dildo into the front of my chastity belt. She straddled me while I sat on the edge of her bed. She thrust herself up and down on the dildo fucking her self on me. I could not feel a thing. I did my best to help her get off by licking her nipples and holding her around the waist and helping her move up and down. When she climaxed she threw herself forward on me forcing me down onto the bed. "That was good. How are you feeling?" "Blue in the balls." "Would you like some relief?" "I'd love some." "Do you know what milking is?" "Like a cow?" "Sort of, but using your prostate." "Not sure what you mean." "That's OK, I'll show you. Keep your shoes on and lie back on the bed. Put your hands above your head." I complied and was quickly handcuffed to the head board. "Don't go away, I'll be right back. I'm going to blindfold you so that you can't see what is happening. I want it to be a surprise." She tied a silk scarf loosely around my head, but wrapped it enough times that I could not see anything. I heard her leave the room. I thought she was going to retrieve the key to the chastity belt. I couldn't wait to get out of the cursed thing even if it was only for a few minutes. I heard her come back into the room. "Did you miss me?" "Yes I did. I've been hoping that you will give me some relief." "That is the plan; I just had to go get something that I think will help give you some relief. Spread your legs." I felt her get on the bed and maneuver between my legs. Lift up your bottom for a minute. I felt her slide a pillow under my bottom. "What is that for?" I asked somewhat concerned. "It is to help you." She ran her fingers up my stockings and tickled the sensitive skin around my scrotum. She leaned forward and kissed me on the lips. She carefully removed the blindfold so that it did not mess up my makeup. She leaned back up and said, "I think it is time that I give you some relief, what do you think?" Reality dawned on me. She was going to penetrate me, and there wasn't anything I could do about it. "No!!!! Please don't do that." "I promise I will be gentle, and this will help relieve the pressure in your balls. You need to ejaculate or be milked at least once a weak to keep your prostate healthy. Since there is no way you can ejaculate in that belt, this is the best solution. Besides, I know you are going to enjoy it, so just relax." It was everything I could do to not kick her and try to get away. I felt her ease the tip of the dildo against my sphincter. "Relax baby, open up. It will feel goooood. Trust me." I did my best to relax and she penetrated me gently. She moved slowly and carefully. It hurt at first, but then seemed to feel better, and eventually did feel good. She found my prostate and as she pressed against it, I could feel something flowing out like a stream of urine that I could not control. She kept this up for a long time. I wrapped my legs around her the way a girl does. When she pulled out of me and I felt strangely empty. With no orgasm, I was still extremely frustrated. She cleaned up the mess she had made. "That wasn't so bad was it?" "I'd rather make love to you instead." "Maybe some day we will do that, but you will always know that I penetrated you first and that you are mine forever. You wear my belt now and eventually, you will accept my collar. When that happens, we will get rid of all of your boy clothes forever. I don't even want to see you wearing women's pants. Just skirts and dresses." She kissed me aggressively and forced her tongue into my mouth. I had truly submitted to her. I said, "I love you." She kissed me again and said, "I know. You make me so happy." She unlocked my wrists and we got cleaned up and went to bed. I awoke to the sound of the alarm clock buzzing. Erin rolled over and kissed me before turning off the alarm. "I want you to turn in your resignation at work today and I am going to order a real estate course for you. How does that sound?" "Kind of sudden, but I think I'd like to try a new career to go with my new life. How long do you think it will take me to earn my license? What if I'm no good at real estate?" "It will only take you a month or two to earn your license. If you put your mind to it, you can knock it out pretty quickly. Don't worry about your success. You are smart and I will help you be successful. It will take a lot of hard work, but it will be fun too." Erin helped me remove the last traces of makeup from the night before and unlaced the corset so that we could shower. We washed each other. This was one of the highlights of my day. "I wish I had never agreed to wear this belt. It is so frustrating." "Don't be too hard on yourself, excuse the pun. I would have put you in it any way. I think it is important for you to have a smooth front. We can't have you getting excited and walking around with a big lump sticking out the front of your skirt." She looked me in the eye and kissed me. I realized that I never had a chance to win against her. She was determined to get her way, and there was no way that I was going to be able to stop her, so I could delay the inevitable or just go ahead and surrender to her. I asked her, "Which do you enjoy more, having me willingly submit to you, or betting with me and having a chance to lose? "Hmmm, that is a tough question. I do love when you submit to me willingly, but it is also fun to win the bet. It is a rush when I get to force you to choose something that goes against your will. Each time I do that, I break down your male ego a little bit more. It is very exciting. Don't give up being the person you are. That is who I love." "Sounds good. In that case, I'm gonna kick your ass next week in class. Within a few weeks, I might have you wearing these corsets." "Is that so? If you are that confident, why don't we double our bet? If I win, I get to make you choose two feminine things, but I will give you four choices. If you win, you get to remove two things. One bit of warning though. Once you chose to wear my collar, you accept my ownership of you. It is very symbolic. Once it is locked onto your neck, you belong to me, and at that point, there is no going back. I will only add more things, and you will continue to become more feminine." I shook her hand and said, "Deal." "Put your stockings on so we can get you laced into your new corset." I did as directed and was soon laced snugly into the new corset. It made my pants fit much differently. It made my waist higher than it normally is. My pants kept riding up and revealing my stockings. I didn't want people to see them at work. I put a sweater on that I hoped would break up my new narrowed waist. I had a heck of a time trying to tie my shoes. I ended up just tying them loosely and then sliding my feet into them. It was impossible to tie them otherwise. I made breakfast and we ate silently both lost in our own thoughts. When I got to work, I copied my personal data to a CD and then deleted it from my computer. I typed up my resignation letter and offered to work an additional two weeks if needed. I signed the letter and went to speak to my boss. He was surprised to see the letter. He asked why I was leaving and I told him I needed to make some changes in my life, and that my career was one of the things that needed to change. Since things had slowed down tremendously, my manager offered to make today my last day, but pay me through the next two weeks. I went back to my desk packed the few personal things that were there, said a few goodbyes and then headed out the door a "free man," although I knew the freedom would be very short lived. I called Erin to tell her the good news after leaving the office. She asked me to stop by her office so that she could congratulate me and take me to lunch in celebration. When I reached her office, she gave me a hug and a kiss. She put her hands on my narrowed waist and said, "that corset really does wonders for your figure. Now that you are no longer worried about losing your job, I think you can show off your new physique a bit more. Let's go have an early lunch to celebrate your new career." Erin took me to one of her favorite restaurants, but instead of letting my order what I wanted, she ordered a salad for me. I wanted the steak and potatoes, but I knew better than to argue. "You need to start watching your figure." After lunch, Erin said, "why don't you go home and put on something special that you think would please me. I'll see you later." I drove back to her house. I still did not think of it as my house too. I wondered what clothing she would like to see me wear. When I got there, I parked my car in the garage and went into the house. I took a large garbage bag from the kitchen and went upstairs. I stripped off my male clothing and threw it into a garbage bag. I put all my remaining male clothes into the bag. I sat down at her vanity wearing the corset, chastity belt, panties and stockings that had become my hidden uniform. I took my time putting on my makeup. Not sure what to wear, I opened the closet to examine all the new clothes I had just purchased. I decided that since I really did not have a paycheck any more, that I should at least try to earn my keep, so I slipped my feet into some black pumps, put on a black slip and then the short black dress I had used as a maid's dress before. I wrapped the apron around my waist and tied it neatly. The blond wig was next. The reflection in the mirror still surprised me. How could I look like such a convincing maid? I picked up the trash bags which contained the remainder of my male clothes and carried them down to the garage. Back inside it was time to plan dinner. I made my plans and then realized I had a couple of hours to kill before Erin got home. I spent the time cleaning the house while I had the stereo cranked up. I lost track of time and didn't realize Erin was home until she grabbed me from behind and b