Cindy and I had worked together for years. We had been peers for several years and became good friends, then I became Her manager. Our friendship continued but many coworkers were certain we were having an affair. We weren’t having an affair, but ate lunch together nearly every day and shared the most intimate parts of our lives with each other. She was and still is my best friend and the only one I have ever felt comfortable sharing every detail of my life with. One day we happened to be talking about role playing and I told Her I had always fantasized about Her being Dominant and making me obey Her. She laughed initially but after more discussion decided to give it a try. She never could get past the fact that I had once been Her manager, so She always used please and thank you and didn’t really do much in the way of Dominating me. I did some chores around Her house but that was about it. Eventually She got a job in another state and moved. We continue to keep in contact with daily text messages and an occasional phone call. She still enjoys teasing me and getting me excited. I get completely distracted when She even hints at something sexual. She has always been a bit of a tease. I did play online with a Dominant Woman for a while and Cindy new about it. They had been secretly exchanging emails so they both knew what I was doing with the other. Eventually Cindy grew tired of the email exchanges and stopped communicating with her. Cindy and I continue to flirt and tease a bit but I honestly never thought She would make good on Her claim that She liked to be in charge and was normally Dominant with men.
One day in early May, i received a call from Cindy telling me that She wanted me to take a Thursday and Friday off of work in the following month to come visit Her. She informed me that Her friend Norma was driving down to visit Her and She wanted me to ride along with Norma. Cindy explained that this was not a request, it was a command. I hesitated a bit and Cindy asked, ‘you keep telling me you want me to order you around, so what is the problem?’ I asked Cindy what I should tell my wife and She said to make something up. I thought for a while and decided to tell Her a co-worker and I were traveling to visit customers on that Thursday and Friday. I never was good at telling lies so I hoped I wouldn’t get caught. Since Cindy had moved away more than a year ago, I have missed Her very much and couldn’t wait to see Her. I continued to fantasize about Her being Dominant to me, but had all but given up on Her actually taking that role.
I began mentioning my trip to the wife and explained a bit about the ‘customers’ we were going to visit. She seemed to be fine with it all. She asked when I would get back and I said that I wasn’t 100% sure because we had several customers to visit and we had to visit them all before we return. I assured her that I would do everything possible to be back Friday evening. I emailed Cindy and asked Her what we would be doing so I would know what to pack. She said we would be dining out, possibly going to the pool or beach, and going to a few clubs. I said, that sounds great, I know what to pack. She told me to be at Norma’s house at 8:00am sharp. She gave me the address and told me not to be late. I had never met Norma before but had heard Cindy talk about Her often. She runs a salon out of Her home and has always been a bit of a slut. I was actually very excited that I was going to finally meet Her and be in the car with Her for 5 hours. Cindy also informed me that because Norma knows some of the same people Cindy and I know, She told Norma that my name was Thomas but everyone called me TC. I asked what TC stood for and Cindy said tiny cock and then laughed hysterically. She said that She had told Norma that I was an old friend from back home that had moved to the area shortly after she relocated for Her job. Cindy told me it was because Norma can’t keep a secret and She didn’t want to chance Norma saying anything to someone we know. I appreciated her being a bit discrete and thanked Her for that. I packed some nice slacks, shirts, and my dress shoes. I also threw in my swimming trunks, some shorts, and a couple t-shirts, some flip flops, and my shaving kit.
I got in my truck and headed to Norma’s house. As I drove, I was thinking about some of the stories that Cindy had told me about Norma and hopes that we would be able to have a little ‘fun’ before we left and on the drive to Cindy’s home. I finally arrived at Norma’s home and rang the doorbell. She came to the door and greeted me. She asked me to come in. We talked for a few minutes and she convinced me to let her drive and leave my truck at her place. She told me she had a few things to finish and that I should put my bag in the back of her car in the garage while she finished getting ready. She handed me her car keys and showed me where the door to the garage was. She went upstairs and I got my bag and placed it in the trunk of her car. I waited in the living room for her to come back downstairs. A few minutes later she yelled down from upstairs and asked me to come upstairs for a minute. I was so excited thinking that all the stories that Cindy told me were true and I was going to get to have sex with Norma before we left. I nearly ran upstairs, she was waiting outside of the guest bedroom. She put her arms around me and kissed me deeply. I was instantly excited and kissed her back. As we continued to kiss and touch one another I felt her reach down and unbutton my pants. I tried to begin unbuttoning her shirt, but she stopped me. She continued to remove my pants but every time I attempted to remove any of her clothing she would stop me. Finally with my pants down at my ankles and my shirt off, she pushed me back and said “Why do you keep trying to unbutton my shirt, I thought you liked for the Woman to be in charge?’ That’s what Cindy tells me anyway, so do you really like submitting to Dominant Women? I said, yes I do. She slapped my face and said , ‘you will always refer to me as Ma’am or Miss Norma’. I sheepishly looked down and said, yes Ma’am. She smiled and said, ‘good, now take the rest of those clothes off and put them in the guest bathroom and meet me in the guest bedroom. I said, ‘yes Ma’am’, and did as instructed. When I returned to the bedroom I was so excited my tiny cock was rock hard. She looked at it and laughed hysterically. She said, “you call that a cock? That isn’t even enough to play with.” My face burned with embarrassment and I replied, ‘yes Ma’am, it is very small’. She said that she was going to have some fun with me before we left but there was no way she was going to let me put that tiny little thing in her.
She told me that Cindy had some special plans for the weekend and that she had put together a surprise for me. She handed me an envelope and told me the box on the bed was the first part of the surprise. She said I should read the letter first and then look in the box. She told me she would be finishing getting ready and that after I read the letter and look in the box I should sit quietly on the bed until she returns. I said, ‘yes Miss Norma’. She smiled and closed the door behind her as she left the room. There I stood, naked in the guest bedroom of a woman that I just met with a note from my best friend Cindy and a box that I had no idea what was in it. This was so exciting; my mind was racing with the possibilities. I opened the letter and sat on the bed and read it. This is what the letter said:
Hello sissy lana!
I know you have been waiting for many years to have me refer to you as sissy. I also like the name that your online Mistress gave you so we are keeping it. You and I both know who you were named after and you know perfectly well how much I despise that bitch. It is going to make it much easier for me to be a real bitch to you this weekend. By now you are naked in a room by yourself with a box. I want you to open the box. Inside you will find 4 boxes wrapped in pretty pink paper appropriate for a sissy like you. I want you to open the box with a number 1 on the top. Follow the instructions in the box and put on the contents as explained. Now open the box with the number 2 on it. I did not put instructions in this box because I know a sissy like you has worn these types of things before. Now box 3, don’t you just love the colors I picked out? LOL! Now the final box with the 4 on it and put on its contents. Now sissy lana, you will do exactly as Miss Norma tells you or else. You know that I have so much dirt on you that if I told people half of it you would be in so much trouble. LOL! Now wait quietly for Miss Norma to come get you.
The first box had a CB-6000 in it but no key. The instructions told me to lock it tight and that Mistress Norma had a key for it in case of emergency. The second box had a black lace bra and panties and black stockings with a garter belt. The third box had white micro mini skirt and a pink t-shirt with the work ‘Pink’ in white letters on the front. It also had a very old pair of flip flops in it. I put all of this on and opened the 4th box like it said to. The 4th box had a white robe in it. I thought this was very odd that She would dress me like a sissy but then let me put a robe over everything to hide it. I put the robe on as instructed and sat quietly on the bed for what seemed like an eternity. Finally Mistress Norma came back in the room, She barked, “stand up sissy and let me see you.” I stood and She came near me and untied the rode and opened it to see what I was wearing. She smiled and giggled as she lifted the skirt to see the panties holding back the bulge from the CB-6000. She said that shirt is nice and tight so I can see you are wearing the bra like a good sissy. She said, that there is something missing. She left the room and came back shortly with two breast forms. She said that a sissy like me needed appropriate breasts. She pulled up my shirt and stuffed the forms into the bra. Then She pulled my shirt back down and straightened the bra and breast forms. She giggled and then She told me to hold open the robe and stand still while she took a picture to send Cindy. I did and She took the picture then She told me to close the robe and follow her. I did as I was told and followed her downstairs. I noticed my clothes were no longer in the guest bathroom as I walked by. I asked, “Miss Norma, where are” and She interrupted me with a “Shut up sissy, you will only speak when spoken to”. Yes Miss, I replied and followed her downstairs. I followed her to a room in the back of her home that was Her hair salon. She told me to, “sit in that chair over there”. I did and she went to a cabinet and grabbed a few items and returned. She said that She was going to do my nails before we left so I would be ready when we arrived. I said, “thank You Ma’am”. I had always dreamed of a woman f***efully feminizing me and it was exciting. It was so exciting that I hurt as my little cock strained against the CB-6000. She held up several colors to my hand and decided on a bright red color. She did some work on my fingernails and then applied the beautiful sexy red polish. Then she did the same to my toe nails. She then began to apply make-up. She put a bunch of some type of foundation on, then she applied several colors of eye shadow and black eyeliner to my eyes, then mascara on my eyelashes. She giggled as She commented that we may need to put on some false eyelashes to make these more pronounced. Then she put blush on my cheeks and finally lip liner and bright red lipstick on my lips. She had my back to the mirror so I couldn’t see what I looked like. She told me to stand up, put on my flip flops, but do not look at the mirror. I did as instructed and followed her. We went back into the house and She told me we were ready to go. She said, “before you start to panic about your things, I placed your clothes from the upstairs bathroom in your bag with your other things.” That was a relief because I was concerned that I wouldn’t have my ID and keys with me. What she failed to tell me was that She had placed the things in my bag , but my bag was no longer in her car. She placed it in my truck. The only thing from my bag that made the trip was my shaving kit that she had removed and placed in the trunk of Her. She told me to take my seat in the passenger side and put on my seat belt and wait for her. I did as I was told and She quickly returned, started the car and backed out of the garage. As the garage door closed, Miss Norma looked over at me with a smirk and said, “well sissy, are you ready for your dream weekend?” I said, yes Ma’am, I can’t wait to spend the weekend with You and Mistress Cindy. She laughed and said, you may change your mind on that after we are through with you. With that She turned up the radio and drove off.
Neither of us spoke until we had gone about 50 miles and were on the interstate. She turned down the radio and asked me if I had any idea what was in store for me this weekend. I said that I really hadn’t ever thought anything like this would ever happen with Mistress Cindy because she said she didn’t like the whole men as sissy’s thing. Miss Norma laughed and said that she really didn’t until a month or so ago. She explained that she visited Mistress Cindy and they were doing shots one night. A game of truth or dare started and She asked Cindy what was the kinkiest thing someone asked her to do. She said that Cindy hesitated and finally confessed to Norma and a few of Cindy’s friends from her new apartment complex that her old friend wanted to serve her as a submissive sissy. She explained that they all roared in laughter and told Cindy that She should invite me down for a weekend that they would help her train her old friend. She laughed and said it would be fun, all along thinking that none of us would remember the next day because we had already done quite a few shots. Unfortunately for you sissy, I have a good memory Miss Norma said. She said that the next morning she had asked Cindy when she was going to bring her old friend down for some “girl fun”. She was shocked that I remembered and tried to back out, but I wasn’t about to let her. Miss Norma explained that she had been fucked over by so many men that she had always wanted an opportunity to get even somehow. She said that if she projected onto me all of the shitty things that had been done to her that she would feel better and I would get my fantasy fulfilled. Then she laughed this evil laugh nearly as evil as Cindy’s and explained that she had always had this secret desire to try being a Dominatrix. She went on to explain that she convinced Cindy to commit to trying this for a weekend and that she would help her. So, here we are sissy, she said. You are in a skirt, bra and panties with your sissy clitty locked away safely and your sissy ass is ours for the weekend. She smirked and said, ‘oh, by the way, remember when I told you that I put your clothes in your bag?’ I said, yes Ma’am, I remember. “Well, I did put them in there, but what I failed to tell you was that your bag is now in your truck back at my house. Yes, that’s right sissy, all you have to wear for the weekend is what we give you or you buy”. I could tell she enjoyed this control as I am sure a look of panic came over my face. I kept reassuring myself that everything would be ok because I trust Cindy and know she wouldn’t do anything to hurt me. It wasn’t long after that Miss Norma slowed to exit the interstate. We pulled into a truck stop for fuel. She handed me a small pink purse. I must have looked puzzled because she said, ‘This is your purse sissy, I took the liberty of moving the contents of your wallet into this purse for you. Your wallet is in your bag back in your truck. She told me to get out and pay for and pump the gas. I couldn’t believe she was having me do this, but thankfully I had the robe on and hoped that nobody would get too close to see my nails. Luckily nobody came near and I was able to pump the gas without being noticed by anyone. I did see a few people looking and pointing but they were far away and I suspect they were just wondering why I was wearing a robe. I hurried back around to the passenger side and got back in the car. Miss Norma was on the phone and said that, ‘lana is getting back in the car now so I have to go, talk to you later.’ She hung up the phone and told me that Mistress Cindy loved the picture she sent and told me to tell you hello. I said, “thank you Ma’am”, and looked down with my face getting very warm again. She started the car and we headed back to the interstate. It was about 100 miles and we slowed again as Miss Norma pulled off to a rest area. She asked me if I needed to use the ladies room and I said, ‘yes Ma’am.’ She said very well, but you have instructions that you must do to earn the reward of using the ladies room. She handed me a bag that was black with pink poka dots. She told me not to look inside yet. She said that because it was obvious that I was a man in womens clothes that if I went in the ladies room I would surely have the cops called on me. She also said that if I send you to the men’s room you will probably get your ass kicked. Just to show you that I can be kind, she said that I should go into the f****y bathroom that is not specifically for men or women. When I was inside I was supposed use the restroom but I was only allowed to sit. She explained that sissy’s do not stand up when they use the restroom like real men do. For the entire weekend until She tells me any different, I was to always use the restroom sitting down. After I finished I was to open the bag and do what the note inside said to do. I got out of the car, made sure the robe was closed good, took the bag and headed inside. I saw some people talking inside and slowed my walk in hopes that they would leave. As I got close to the door, they did leave but they were walking right toward me. My heart began to race 100 miles an hour. I wanted to run, but there were people behind me too so there was no turning back. As the door opened they walked out and were so involved in their conversation they didn’t even notice me. What a relief! I walked in and quickly found the f****y restroom. I certainly hoped that there was nobody in there because I didn’t want to wait while people came and went. I quickly went to the door and turned the doorknob and breathed a sigh of relief as it opened. I hurried in and closed then locked the door. My heart was pounding in my chest. It was from both fear and excitement. As I turned and looked in the mirror, for the first time I saw what Mistress Norma had done to me. If it wasn’t for the short haircut , I looked like a real woman. I couldn’t help but start at myself for a few minutes admiring Her work. Then I realized that Mistress Norma was waiting in the car and I had better hurry. I would hate to be left at the rest stop. I had left the purse in the car so I had no ID or money. I walked over to the toilet and until this moment I had not considered how I would go to the restroom with the CB-6000 on. I had never been in chastity so this was a completely new experience for me. I removed the robe and hung it on the hook behind the door. I pulled down my panties and held up my skirt to study the device. It did have an opening in the end and I realized it was so you could use the restroom without having to remove it. So, as commanded, I sat down and did my business. As I finished I had to shake the entire CB-6000 to remove the last drop. It was a different experience for certain. I pulled up my panties and straightened my skirt. I walked over to the counter where I had placed the bag and opened it. Inside was a note, a long auburn wig, and a pair of boots. I read the note and it was from Mistress Cindy. She told me to put on the wig and straighten it. In the bottom of a bag was a brush and she told me to brush it as needed but to not brush out the curls. The note also told me to put on the boots. She went on to explain that her and Mistress Norma had decided on thigh high boots because they would completely hide my hairy legs and they looked more slutty than just heels. She commented that I probably looked like an amazon with those big feet. She said that they had a very difficult time finding size 13 boots. The note said, after you put on the wig and boots, neatly fold the robe and place it in the bag. Then I was to go back outside and walk around the building 3 times before returning to the car. She explained that if I did not circle the building at least 3 times that Mistress Norma would drive off and leave me there. I panicked as I thought about what might happen. First of all, I have never walked in anything with heels this high before, and thought it was going to be obvious that I had never done this before. Then I was thinking about all the trucks stopped outside and the people milling about and quite frankly I thought I looked like a real slut. I stalled for a few minutes until I got up the nerve to go outside. I picked up the bag, and wobbled out the door of the restroom into the lobby of the rest stop. There were no people in there and thankfully there hadn’t been much traffic on the interstate so the rest area was fairly empty. As I walked out the front door I looked over at the car, Mistress Norma must have thought I was heading straight for her because she began backing out of her parking spot. I quickly turned right and began my first walk around the building. I bumped into two men walking around the corner and smiled at them both. It must have been very dark because one of them said, “WOW! How are you sweetie?” I just smiled and kept walking. As I completed my first lap there was a couple and I overheard the man say as he looked at me, ‘why can’t I get you to dress like that for me?’ The second time around the building was going well until I was about half way around. There were a couple of truckers talking in the parking lot and one of them whistled at me. I kept walking hoping that I would not draw any more attention. As I rounded the corner half way through my third lap around the building, those same two truckers were still there. One shouted, “Hey Sweetie, wanna go for a ride?” I waved and sped up my pace, I rounded the corner and decided to walk past the front door again to make it 3 complete times around the building as to not upset Mistress Norma. Then I headed for the car. My walking had gotten better and I was less wobbly, but my calves were killing me. As I made it to the car I realized that Mistress Norma had been using the video function on her phone to capture my walk of shame. I opened the door and she told me to place the bag in the back seat. I did as instructed and then climbed into the front seat. She was giggling at me and was texting someone as I buckled my seatbelt. I sat there and she looked at me with a smile, then reached across and opened up the glovebox and pulled out my cell phone. She said that Mistress Cindy has texted you and wants you to respond immediately. I read the text and it was a question. “Is this fun for you and everything you imagined it would be?” I looked at Mistress Norma and she said, “well, don’t look at me, respond to her. I didn’t know what to say. Yes it was exciting but my head was spinning because this was happening so fast and I hadn’t mentally prepared for it. I began typing my reply as Mistress Norma backed out of the parking spot and headed back to the interstate. I typed, “Mistress Cindy, I am having fun. It is exciting and scary at the same time. Mistress Norma did a wonderful job, thank you Ma’am.” I hit send and very quickly there was a response, she said, “You did not answer the second part of my question, is it everything you thought it would be?” That was a tough one, I had imagined many scenarios with Mistress Cindy doing things like this to me. I replied, “So far it is very much what I thought it would be, thank you Mistress Cindy for taking the time to do all of this. I do realize that this has had to take a significant amount of planning.” I did not get an immediate reply. After several minutes, Mistress Norma asked me if I was finished texting. I said that I think so Ma’am, Mistress Cindy has not replied. She said, very well lana, put the phone away in the glove box. I said, “Yes Ma’am” as I put the phone in the glove box as commanded. It was quiet for a little while and then Mistress Norma asked me how I liked my little walk around the rest area. I replied that it was exciting and humiliating. I said it was difficult to walk in these high heeled boots at first, but it was easier after a little while. She asked me what the men said to me? I said that they just said hello sweetie and that I smiled politely at them. She said, and what about the couple, the man was pointing at you. I smiled and said that he asked his wife why she doesn’t dress like this for him. Mistress Norma roared. I asked her if I may speak freely. She said, “Yes, but only until I tell you to stop.” I said, thank you Ma’am. I told her that I very much appreciated the time and effort that she and Mistress Cindy had put into planning this all. I also thanked her for the wonderful job she did on my nails and with the makeup. She laughed and said, “Don’t thank me lana, you will be paying me back later. Now stop talking until I ask a question of you.” I looked down in silence as she drove. A few minutes later, she asked if anything else happened at the rest area. I said that there were two truckers around back that whistled at me and asked me if I wanted to go for a ride. I politely waved at them and continued walking. She began laughing and said that I was lucky there weren’t any cops around; they would have certainly arrested me for prostitution the way I look. She was right, I was so excited about being dressed by two beautiful women and that they had made me look so good I hadn’t even considered that I was walking around a rest area dressed like a prostitute. The rest of the ride was quiet except for Mistress Norma answering a couple of texts. She laughed several times and looked at me after she read some of the texts. When we began getting close to the city that Mistress Cindy lives in, she called Mistress Cindy and asked if she was ready to meet us. She said, “ok, we will be there in 5 minutes”. My heart began to race at the thought of Mistress Cindy seeing me like this. She had told me in the past she had no interest in any of this f***ed feminization and sissy stuff. Mistress Norma seemed to really be enjoying herself and I started thinking that maybe she had put this whole thing together and that Mistress Cindy didn’t know I would be dressed like this. I wanted to go back and read the texts to see if I could determine if she was asking about my being dressed or something else, but didn’t dare ask. I was so nervous thinking that she may not be expecting this. As we drove, Mistress Norma looked over at me and said, “you look nervous lana, relax.” I said, “Yes Ma’am, I am.” She laughed and patted me on the leg as she drove along. Finally we started to slow, I had never been to Mistress Cindy’s new place so I had no idea where we were going. I quickly realized that we were not going to Mistress Cindy’s house, we were pulling into the parking lot of a mall. We parked quite a way from the mall and she turned the car off. I was really nervous. A few minutes later Mistress Cindy parked next to us. She looked over at me and started laughing hysterically. Mistress Norma told me to sit still as she got out of the car and talked to Mistress Cindy. They greeted each other with a hug and were talking, pointing and laughing at me. Finally Mistress Norma opened my car door and said get out sissy. As I stood up Mistress Cindy motioned for me to come to her. I walked over to her as she looked me over from top to bottom. She said, Norma you were right, she is almost passable. The slutty clothes are quite appropriate. Mistress Cindy told me to turn around. I did and she lifted up the back of my skirt to see my panties and laughed. She said, ok you can give me a hug now lana. I turned back around and gave her a hug. I had missed her terribly and was so glad to see her. As I stood back up from the hug Mistress Cindy said, you asked for it, now you are going to get it. We have quite a weekend planned for you. If you behave you will get to go back home and nobody but the three of us will know what happened this weekend. If you misbehave, you will be hating life when you get back. She asked me if I understand and I said, “Yes Ma’am.” She said good, then looked at Mistress Norma and said, “We can’t take her into the mall looking like that, they will think she is a hooker.” They both laughed and decided that we needed to go to a more appropriate place to shop for someone dressed as slutty as me. I had no idea what that meant, but we drove off and Mistress Cindy turned around and said to me, “I bet by the end of this weekend you are going to be sorry you wanted this and that you wanted Me to ‘train’ you!” They both laughed as we headed down the road. Mistress Norma said, “This is definitely going to be a weekend she will remember.” Then Mistress Norma looked at Mistress Cindy and said, “I sure am glad we all had too many shots last month and you told me about this. I can’t wait for the fun we have planned.”