I hadn’t seen Cindy for nearly 2 years, other than a quick lunch as She passed through town last year. We text or IM almost every day and talk on the phone every few weeks. We had been coworkers for many years and remained very good friends to this day. I would say that She is my best friend as I have been able to confide in Her about things I have never told anyone. In addition to being a very trusted and loyal friend, Cindy is beautiful and very desirable. I still can’t figure out why some man hasn’t swept Her off Her feet and married Her. She is truly amazing.
As I said earlier, I have told Her things I have never told anyone. She knows of my submissive side and adventures with a couple of online Mistresses. She also knows my sissy clitty is very small and that I have trouble getting it up. That is a story for another day, LOL! After I confided in Her that I wanted to be submissive to Her She had me do some things around Her house but wasn’t really assertive and always said please and thank you. It was more like helping out a friend than it was a Dominant/sub thing. I always told Her that I am willing to do more, specifically I said many times, ‘I will do ANYTHING for You!’ Cindy moved away eventually so the helping around Her house stopped.
During several of our chats I confessed various things to Her at the prompting of an online Mistress I had been chatting with. I confessed that I enjoyed wearing lacy things and using a vibrator on my sissy pussy. There were other things of that sort that I confessed over the years, but She did little more than laugh most of the time. I loved Her laughing at me as it was humiliating and exciting. Once in a while She would push me a little by asking questions and making comments. Shortly after She moved She started urging me to come for a visit. I was very excited thinking about a visit to Her. As much as I would like to sl**p with Her, She and I both know it would only frustrate Her. But I love being around Her and just talking. Recently Cindy began to push me more on visiting. I had been saving up for a trip to visit Her and was at the point that I could come for a visit for a long 3 day weekend. I asked Cindy if She had plans and She said no. I asked if She was serious about me coming down for a visit and She said, ‘of course I was serious!’ She said I was always welcome to visit. So we firmed up the plans on when I would arrive the following month. I was very excited thinking about the visit. She told me to save a little extra spending money because She had some fun activities planned. I didn’t pick up on it as the weeks passed, but gradually She was asking more questions about my interest in submission and my sissy tendencies. She was gathering information for my visit. We talked on the phone the week before my visit and She seemed very excited about my pending visit. I asked what She had planned for us to do while I was there and She said dinner and drinks with some of Her friends and a few other fun activities. I left it at that because I suspected She was going to surprise me with some wonderful attraction or show and I didn’t want to spoil the surprise. Finally the day arrived for my visit. It is a 4 hour drive so I snuck out of work at 1 o’clock so I could be there when She got off work. She called me and said She was running late and that I should stop for a drink or something and give Her till 5:30 to get home. What I didn’t know is that She was home at 5:00 getting ready for my arrival. I finally arrived at Her house and pulled in the driveway and parked. I opened the trunk and began getting my suit case out when my phone rang. It was Cindy telling me not to bother bringing anything in for now, we have time for that later. I have a surprise for you, and said the door is unlocked come on in the house. It was kind of odd but even when She is asking me to do the simplest things I fantasize about Her ordering me around. This was a great opportunity for me to imagine being a good slave. So, I put the suit case back in the trunk and closed it. I locked the doors on the car and went inside.
As I came in the door I called for Cindy and heard Her say, ‘in Here’ from the living room. When I came around the corner and saw Her standing in the middle of the living room I bet my chin hit the floor. There She stood with Her beautiful blonde hair looking wild and sexy. She was wearing more makeup than I had ever seen Her wear. She really doesn’t need any makeup to look awesome but She looked amazing and super sexy. She was wearing a white ruffled blouse with enough buttons undone that I could see Her beautiful black lace bra and most of Her milky white breasts. She was wearing a leather mini skirt, garters with black stockings covered with the most shiny pair of thigh high boots with 5 inch heels I have ever seen. She had the evil smile on Her fact that always drove me wild and as I opened my mouth to say how amazing She looked She pointed Her finger at me and said, ‘stop, don’t say a word you sissy.’ That really wasn’t a problem because as soon as She raised Her voice and pointed Her finger at me I was speechless because I never imagined Her being like this. She had told me before She liked to be in charge but had never shown me that side of Her. She said that I was only to speak when asked a question and that I was to address Her as Mistress Cindy from this point forward. ‘Do you understand?’, and I responded yes Mistress Cindy. She laughed that evil laugh that anyone that knows Her well has heard, I thought I was going to make a mess in my pants. This was a dream come true. She pointed to the floor and said, ‘on your knees slut!’ I immediately got on my knees. She asked me if I was certain that I wanted to be Her sub slut for the weekend and without thinking I blurted out, ‘Yes Mistress Cindy, I do want to be your sub slut.’ She said ‘and you are willing to do anything I command you to do?’ I immediately replied ‘yes Mistress Cindy’ without giving it a second thought. You see, She had told me She was a little kinky in the past but had never gone into any detail on exactly what kinky was to Her. From our past interactions I couldn’t imagine Her asking me to do something I wouldn’t gladly do, especially given the fact that She hadn’t been very assertive when we played this scene in the past. Next She said that because one of my online friends had picked the name lana that She was going to call me sissy lana all weekend. She said, ‘sissy lana, you and I both know why that name is perfect don’t we?’ ‘Yes Mistress Cindy’ I replied. You see, we had both worked in the same company and it was because of a woman named Lana that we were both no longer there. Mistress Cindy said, ‘come to think of it, She was very dominant and liked being in charge, I am surprised you didn’t stay working for Her and being Her little bitch.’ She thought about that for a few seconds and then She said, ‘now stand up and take off all your clothes’. I immediately hopped up and pulled my shirt off over my head, kicked off my shoes and socks and dropped my pants. I was standing there in my underwear with my little cock harder than it has ever been. She laughed and said ‘if that is all you’ve got when you are this excited it’s no wonder you have never satisfied a woman sissy lana. I told you to get undressed, lose those underwear now.’ So I took off my underwear and She laughed when my tiny cock flopped out. She told me to stay right there and not move. She left the room and I was in awe as Her beautiful hair bounced with each step and Her sexy ass shook from side to side. I didn’t think I could get more excited but I was as She walked away. She disappeared into the other room. I heard Her open the refrigerator and get some ice. I figured She needed a drink. She came back with a zip lock bag full of ice. She said, ‘any real sissy should not have a little hard-on like that. Put this ice on it to make it go down.’ I did as She said but it took several minutes for it to start to soften. She was growing impatient; She walked around behind me and slapped my ass. She said, ‘hurry up sissy, we don’t have all day.’ She left the room again and finally my hard-on went soft. I didn’t dare take the ice off of it for fear it would get hard again. From the other room I heard, ‘is that pathetic clitty soft yet lana?’ ‘Yes Mistress Cindy’ I replied. In a few minutes She came back in the living room with a small black bag. She asked me if I knew what was in the bag and I replied, ‘no Mistress Cindy.’ She said I should because I am the one that showed it to Her. My mind raced because I had sent Her so many pictures over the years and talked about so many things. I had no idea what might be in the bag. She unzipped the bag, reached in and pulled out a CB-6000. I dropped the bag of ice when I saw it. She yelled to pick that ice bag up and put it back on that little clitty. I did as commanded as She pulled all the pieces out and sorted them on the table. She told me to lower the ice bag and She began to assemble the pieces. In no time at all She had it on me and clicked the lock shut. She laughed a very evil laugh and said, ‘well sissy, there is no turning back now!’ She said to go upstairs into the guest bedroom and put on what was on the bed. I bent over to pick up my clothes and She told me to leave them where they are that they can be taken care of later. I turned to walk upstairs and She smacked my ass and said, I didn’t hear you say, ‘yes Mistress Cindy!’ I turned back around and looking down at the ground said, ‘yes Mistress Cindy.’ She said that is better now go get dressed.
As I walked up the stairs my mind was racing, what just happened to me and is that really my friend Cindy down there? I had always fantasized about Her doing things like this to me but never imagined it would really happen. As I made it to the guest bedroom there was an outfit laid out on the bed. There was a note explaining how I was to put everything on. I sat on the bed and as instructed in the note pulled the dark black hose over each of my legs. They were so dark that you couldn’t see the hair on my legs. Then I pulled the black lace panties on and tried to tuck the CB-6000 into them but it didn’t fit well and caused the back of the panties to pull tight against my back side. Next I picked up the sexy black lace bra as instructed and put my arms through the straps, while I was attempting to hook it behind me, I heard the doorbell. I panicked and ran over to close the bedroom door and locked it. I heard Mistress Cindy talking to another woman downstairs but couldn’t make out what they were saying because I closed the door. I decided to get back to getting dressed while Mistress Cindy got rid of whoever that was. I finally got the bra hooked. I picked up one of the breast forms and was surprised how heavy it was. I put the breast forms in the bra and couldn’t help but feel them, I thought to myself, ‘if I were a real woman I wouldn’t be able to leave these alone!’ I was starting to get excited again and felt a good bit of discomfort as my little clitty strained against its cage. Next I picked up the corset and tried to figure out how to put it on. I eventually figured out that the hooks closed the corset from the front and the laces go in the back. I pulled the laces as tight as I could and attempted to tie a bow, unfortunately it was not a very good bow but I was not skilled at tying behind my back. I turned around and looked at myself in the mirror. The open cup black corset lined with red trim was so beautiful. It was a bit uncomfortable but I have to admit that I really liked the feeling. I attached the garters to the stockings with the hooks. It took me a few minutes to figure out how to attach them but finally I got it. The last item the note instructed me to put on was the stiletto heels. They were shiny black and I would guess that they were 5” heels with a strap that went around the ankle. The ankle strap was thick and had a hasp for a padlock to keep them on. There were two locks that the note instructed me to use to secure the shoes. I snapped the locks shut and my task was complete. Now I was to go back downstairs for inspection. I stood up and wobbled as I tried to walk to the door. I had always appreciated a woman in heels and the higher the better but this made me realize that women endure a lot of pain for the sake of beauty. I finally made it to the door and slowly cracked the door open and listened. I wanted to hear if the visitor had left yet. I didn’t hear any talking so I made my way to the stairs. I was still wobbling and was afraid I would break my neck going down the stairs. Slowly it took each step and made my way downstairs. As I stepped on to the hard wood floor at the bottom of the steps, it was the first time I heard the click of the heels as I walked. As soon as the first click of the shoe rang out, from the living room I heard, ‘In Here slut, NOW!’ I replied, ‘Yes Mistress Cindy!’ I clicked and wobbled my way into the living room where Mistress Cindy was sitting on the couch sipping a glass of wine. She laughed hysterically for what seemed like minutes after She saw me. She finally stopped laughing and said that She even impressed Herself, all the sizes were perfect. She stood up and walked over to me, She slowly circled me until She got behind me. She smacked my ass and said that I did a pathetic job tying the corset. She quickly untied the bow and beginning at the top, pulled each lace tight. As She worked Her way down the corset got tighter and tighter. It felt like it was cutting my sides. Finally at the bottom She pulled the lace super tight. She said that is not tight enough, She told me to suck in my fat gut and don’t move. She went over and got a chair and placed it behind me. She sat in the chair, leaned forward and grabbed the laces She put one of Her boots on my back side making sure the heel was pushing my panties tighter into my crack. She pushed me forward with Her foot as She pulled on the laces. I winced in pain as She quickly tied the laces into a double bow. As She put the chair back I was in trying to breathe. I must have been looking like I was about to pass out because She told me to not panic and to take slow shallow breaths until I learned to adjust. Once She calmed me down and had me breathing better She slapped my ass again and said that if I wasn’t such a fat ass I wouldn’t be struggling to breathe so much. ‘Only salads for you for the weekend sissy’, She said as She laughed hysterically again.
She asked me if I would like something to drink and I said, ‘yes please Mistress Cindy.’ She said, ‘well go in the kitchen and get me another glass of wine and something for yourself, there is light beer in the refrigerator that is appropriate for a sissy like you!’ I took Her empty wine glass as She sat back down and I went to the kitchen to get the drinks. I returned with a glass of wine for Her and a lite beer for me. She sent me back to the kitchen because I didn’t use the serving tray She had laid on the counter. She said that a proper submissive sissy should know how to be a good hostess and serve Her Mistress properly. I returned and put the drinks on the tray. I was really nervous about carrying that tray with those high heels on. My calves ached bad already and I was not steady at all. It took great concentration but I was able to slowly make my way back into the living room without spilling a drop. I sat the tray down and handed Mistress Cindy Her glass. She said, ‘very nice job sissy, I was certain you would make a mess.’ She told me I could take a seat and we would talk for a few minutes while I drank the beer.
She asked me how I liked being sissy slut lana so far? I said that it was exciting and I appreciated the thought She had put into all of this. She asked me if it was all I thought it would be? I told Her that it was more exciting that I ever imagined, it must be exciting me because this cage is really hurting me because I am so excited. She laughed that evil laugh again. After laughing, She got this really evil smile on Her face, She said that there was no turning back now. She reminded me that I have been going on and on about all of this for years and She is calling my bluff. She said that the clincher that made Her decide to start planning this a few years earlier was my comments about the French. I had made some snide comments about them and my expieriences when I was in France. Not knowing that She was French and She had taken 4 years of French in high school, my comments really pissed Her off. She asked me where my clothes were, I looked over on the floor where I took them off and they were gone. I said they were right over there. She laughed again and said, ‘were is correct, do you know where they are now?’ I said, ‘No Mistress Cindy I do not know where they are.’ She said, ‘I will tell you where they are sissy, they are in your car along with the keys to your cock cage and those slutty shoes you are wearing. ‘ I thanked Her for collecting my things and putting them safely in my car. She roared with laughter and apparently I looked confused. She said you don’t understand do you? You see, I took the $200 to pay for the shoes, the CB-6000, and other supplies for the weekend. Most of the clothing items were donated to the cause so I didn’t spend much on this so far She told me. She warned me that She may need more money. She went on to explain that my wallet, clothes, and suit case were all in my car with the keys for the locks but that my car wasn’t there. I jumped up and ran to the door to look and sure enough, my car was gone. She explained that this is Her insurance policy to make sure I don’t back out. One of Her friends had stopped by and taken all of my belongings to Her home for safe keeping in Her garage. I didn’t know any of Her friends from the city She moved to so there was no way I could figure out where my car and things were. She had me and there wasn’t anything I could do about it. She said, ‘you asked for this and you are going to get it, I suspect you won’t be teasing me about not being as kinky as I claimed after I am through with you this weekend you slutty sissy.’ She told me to sit back down and not get up until She instructed me to. I sat back down and must have had a worried look on my face. She commented on it and said that there were portions of the weekend that had not been decided yet, it could go one of two ways and how well I behaved and took to the training would determine which way it would go. She said so far I hadn’t impressed Her much so She thought it would go badly for me and I would be f***ed to do things I had never imagined and that I would probably not enjoy. Now I was scared and She knew it and She seemed to delight in it.
She sat back and said, now that you know I have 100% complete control let’s get to this. We only have 36 hours to determine how your last 24 hours will go. She said, ok it is 7:00 and my friend Jan will be Here any moment. Before She gets Here I have something else for you. She sent me over to the table in the corner to get a box and bring it to Her. She told me to set back down as She opened the box and took out the most beautiful fiery long auburn wig that had sexy curls in it. She came over and put it on my head, moved it around a bit to get it situated and put some hairpins in to hold it in place. I was so excited, and I asked Her why She chose red for the wig. She said, ‘it is because that is one I haven’t done before, now stop asking questions slut!’ I wanted to ask what that meant, did She mean She hasn’t make a redhead sissy before, She hadn’t had a red wig before, or something else. I decided to keep my mouth shut and go with it. Just as She finished the doorbell rang. She told me to go answer it and greet Miss Jan then e****t Her in Here and ask Her if you can get Her a refreshment. I jumped up and wobbled to the door, I opened it and there was a beautiful brunette standing there, She was dressed very professionally and carrying a case of some sort and trying not to crack up laughing. I asked if I could take the case for Her and show Her into the living room. She said that would be nice and handed me the case. I followed Her into the living room and Mistress Cindy greeted Her and told me to put the case down on the table. I asked Miss Jan if She would like a drink and She said yes, a glass of wine would be very nice. I picked up the serving tray and went to the kitchen. I poured Her a glass of wine and placed it along with the bottle on the tray and returned to the living room. I handed Miss Jan Her glass and asked Mistress Cindy if I could freshen Her drink. She was impressed and said that maybe I had a promising future as a homemaker or maid. I poured Mistress Cindy another glass and took the bottle and tray back into the kitchen. When I returned they were laughing about something. Mistress Cindy told me to take the case up into the guest room and place it on the table, then set in the chair in front of the mirror and they would be up shortly.
I was waiting in the guest room for about 20 minutes. Finally I heard them both coming upstairs. Mistress Cindy explained that Miss Jan was a cosmetic consultant and was going to teach me the proper way to apply makeup. This was a onetime lesson then I was responsible for doing my own makeup from there on. She reminded me that my level of performance would determine how my weekend ended. Miss Jan got to work and explained to me each step of the process. With each step She told me what a nice girl would do when applying makeup but then said, but you are not a nice girl, you are a slutty sissy so you should do this. They both laughed each time. Miss Jan finished and I couldn’t believe the results, I had no idea that I could be done up so lady like. Miss Jan was off to a date but left enough makeup samples for me for the weekend. I was instructed to carry Her case downstairs and see Her to the door. Mistress Cindy said goodbye to Her upstairs and told Her I would see Her out that She had some things to get ready. As I walked out of the room behind Miss Jan, Mistress Cindy told me to get Her wine and bring it up as soon as Miss Jan leaves.
I saw Miss Jan out and handed Her the case on Her way out. I went to the living room and got Mistress Cindy’s wine glass and hurried back upstairs. I noticed that even though my legs hurt terribly that I was getting better at walking in the heels. When I got back upstairs Mistress Cindy said that I looked the part of a true sissy slut now and that the score keeping began after Mistress Jan left. Over the next 24 hours I had 3 strikes to lose. If I 3 strikes or less then She would put plan A into effect at 9:00 tomorrow, if you have more than 3 strikes plan B will be put into effect and I don’t think you want that. Then She casually said, oh by the way, you just lost one strike for not bringing my drink on a tray. Two more to go. Now, go into the bathroom and you will find two enemas on the counter. I want you to clean yourself out really good using both of them, when you are sure you are clean I want to you to come back in Here and stand in the middle of the spare bedroom touching your ankles so I can inspect you. I hurried off to the bathroom and used both enemas. I had never had an enema before so I wasn’t sure what to expect. I read the directions and it wasn’t too bad after the initial discomfort. When I was done I cleaned myself up really well and went back into the bedroom and grabbed my ankles waiting for inspection. Soon Mistress Cindy came back in and pulled my panties to the side and said that I had done a fairly good job but tomorrow I would need to shave that hair out of my crack tomorrow because no good sissy has a harry pussy. She told me to continue to hold my ankles and not move. I heard Her doing something behind me but couldn’t make out what it was. She finally told me to relax and don’t fight it or it will hurt worse. She pulled my panties to the side again and I felt something cold against my back side. She pushed kind of hard and it popped into my ass. She slowly pushed it all the way in and kept telling me not to strain but to relax. After it was all in She pulled my panties over it and told me to stand up. I felt something hanging out of my back side and it was a little bulb, She grabbed it and pumped it a few times. The plug started getting bigger with each pump and was stretching my back side. It hurt really bad and She kept telling me to relax. She said that I would thank Her later for this. Now, it is almost 10:00pm and She wanted me to get ready for our slumber party. She said I could take off the corset and put it in the top drawer of the dresser. Then She handed me a pink babydoll to put on. She explained that I had to leave the shoes and stockings on because the shoes were locked on for the remainder of the weekend and the key is at Her friend’s house. She said that after I was dressed and straightened up my hair and makeup to come into Her bedroom for our slumber party. I went in to Her room and She patted Her side of the bed and told me to set down. She went to Her bathroom and came back out with a sexy black lace teddy on. I could see Her beautiful breasts through the teddy and it caused me to strain against the cage again. She smiled and climbed into the bed. She asked me how I felt and I said that my head was swimming with excitement and fear. She patted my caged crotch and said, ‘good, that is what I was going for.’ She turned on the TV and started the DVD with season 1 of Her favorite series ‘The Client List’. She said we would watch tv for a while and have some girl talk before we went to sl**p. She said it certainly is too bad you aren’t a real man, you could be having your way with me right now. She said that all of this had made Her super horny but with my tiny little clitty locked up it was no good to Her. She said She had an idea of how I could please Her but it would mess up my makeup. I said, ‘anything you say Mistress Cindy.’ She laid back and pulled Her panties off and said to get to work, that is all I am good for. She laid there and watched Her show while I tried my best to please Her with my tongue. She kept commenting on how pathetic I was as a man but that I made a really good sissy slut. She said that if I didn’t make Her have an orgasm by the time the video was over it would be strike 2. I kept at it and even though my mouth and tongue hurt I didn’t stop. Finally She grabbed my head and pulled it to Her and started grinding my face into Her. This excited me so much that the pain was almost more than I could take as I strained against the cage. Finally She began to buck wildly and scream as She had the only orgasm I had ever given a woman. When She finished She let go of my head and told me to look at Her. She smiled and told me to go get a warm washrag and clean up the makeup off of Her thighs. I did as She commanded then She told me to go to the bathroom and take all my makeup off and then return for goodnight instructions. I cleaned off the makeup and returned. She said I did well and that She was very pleased with my progress. She said that in the morning She wanted orange juice, fresh fruit in a bowl with a little cream, and a toasted bagel with cream cheese for breakfast at 10:00 am sharp. I said yes Mistress Cindy. She said turn around and back up. She grabbed the bulb on the plug and gave it 3 big pumps. She said that should keep you uncomfortable and stretching all night. Now go to sl**p sissy and have my breakfast ready in the morning. Don’t forget to clean the kitchen too. Goodnight sissy slut lana!