15 comments/ 124664 views/ 27 favorites Becoming a Sissy Slave By: mikhaylacumme He gave me the choice. He had programmed me for a week and knew which way I would probably choose, but he gave me the choice. I could get out. Or I could continue. It was up to me. On my knees or out the door. It was that easy. Now I had to choose. I guess I should backtrack, first. You might be scratching your head saying 'what choice?' Let me start at the beginning. It began a week ago. I had decided to head out to an alternative bar. I had popped in here once or twice before for kicks. Usually, I'd go home and jerk off after, imagining what it would be like to live out some of the fantasies those people live. Crossdressing. Domination. Slaves and masters etc. That night was a little different. I grabbed a beer at the bar and looked over the scene. There were all sorts of freaks at the bar. Some were hot, some not so much. But my crotch tingled when I looked at most of them. Then a sexy blonde slid up next to me. "Hey there. You look like you could use a friend." Well, yeah. She was quite the looker. Deep blue eyes. Blonde hair to the middle of her back. Purple eye shadow, blush, red lipstick. A halter top that showed off all of her 36 D chest. A beautiful belly button piercing and a skirt that barely covered anything. And oh those legs. Covered up with beautiful fishnet stockings, they went straight up. She had on hooker heels, too. Red and with a good 6-inch heel. So hot. And she smelled even better. My crotch really started to twitch. She snuggled close to my ear and whispered, "If you are looking to get a little freaky tonight, let me know. I'm interested." Jackpot! A few more drinks and some small talk followed before she led me out of the bar and we were soon back at her place. I'm not the most masculine guy in the world. Some might say I'm actually a bit feminine. I have a small build, I'm not too hairy and I let my hair grow to my shoulders. I have soft features, too. I've actually been hit on by guys who thought I was a woman from behind. But one thing that has always saved me is that I'm hung quite well. Nine inches and I can use it quite well. So I was confident with that but once we got back to Tonya's apartment, she took control. We had another drink and I was a little tipsy when we started getting naked. She was fully naked with her back to me and turned around. She had a wonderful smile. And amazing set of tits. A tight stomach. And... and... and... Holy shit! A rock-hard cock that was about as big as mine! I've never been with a guy (or a gal with a cock) and I was mortified. She came over and caressed my shoulders and hair. "Don't worry, baby. We'll have fun. Now pucker up." Before I could say anything, she had put bright red lipstick on me, pushed me to my knees and pushed my mouth over her cock. She got into a rhythm of fucking my face at a steady pace. She slowly started going deeper and deeper into my mouth until she was soon touching the back of my throat. This went on for 15 minutes until I felt her cock start to throb in my mouth and she started to moan as she started to cum in my mouth. She got about five good spurts in before she pulled out and put three or four more shots all over my face. She instructed me to swallow what she unloaded in my mouth and I did as I was told. She then reached down and squeezed my balls a couple of times before I unleashed a load into a glass that she held. She then forced me to drink my own cum, saving some of it so she could dump that on my face, too. As I laid back, with cum all over my face and my cock getting soft, she applied a chastity device to my dick. I was captured, apparently. "OK, sweetie. Here's the deal. I'm going to give you the chance to live out your fantasies. I have a friend and he wants a sweet little sissy bitch. Basically, you'll be treated like gold. Everything paid for. An amazing room and clothes. In return, you become his domesticated bitch. You cook. You clean. You suck his cock. He fucks your man pussy. When he has friends over, you'll probably be used as the whore you are." I sat there dumbfounded. "One week. You try it for a week. At the end of the week, he'll offer you a lifetime contract. Basically, by signing it, you'll agree to be his slave for life. Or, you walk out." I sat staring ahead. Covered in cum. So much to decide. I didn't have any real connections to the world anymore. No family left. Not many friends. Recently unemployed. And I did enjoy sucking her cock. "OK, I'll try it." I was whisked away to this house in the country. When we got there, I was taken inside and to a beautiful room. The closet was filled with clothes. The dresser had fancy panties and frilly lingerie. Within moments I was made up to look a little slutty. Blue eye shadow, red blush and red lipstick. Fake fingernails were put on, red of course. Toe nails were also red. A triple dosage of mascara was put on. Fishnet stockings connected to a garter belt. I was put into a G-string and a bra. My hair was puffed up and shaped. My eyebrows plucked and shaped. I was then put into a leather French maid's outfit and 5-inch heels and ushered downstairs where I met my new master. I bowed to him as I was told as he inspected me. He then pushed me to his knees and pulled out his cock. I sucked away until I got a mouthful of cum and swallowed it down. He then placed me over the couch, pulled my dress up and pushed my G-string aside as he started to finger me with lubricant. I moaned with pleasure as he soon inserted his cock and took my virginity with a little extra force. For the next 20 minutes he fucked me hard and soft until he unleashed a load deep inside my man pussy, effectively marking his property. The next week was a whirlwind. I sucked his cock at least three or four times a day and he fucked me two or three times a day. Twice during the week, he had a group of friends over and they used me like a cheap piece of ass. I was loaded with cum in both holes and all over my stomach and chest. I learned how to take care of his house and cook. I cleaned and did everything a domesticated servant would do. My days were long -- I was up by 5:30 a.m. to get ready as my makeup and shower and dress took about two hours to get ready. He wanted breakfast by 8:30 a.m., so I had to work. After cleaning and doing everything else each day, then being his personal fuck toy for several hours each night, I usually didn't get to bed until 12-1 a.m. I didn't get much sleep, but it was a routine I got into. That brings us back to the present time. Here I am, dressed as a little slut and standing in front of my master. He's just outlined what the contract says: he'll be able to change my body with tattoos, breast implants or other plastic surgery. If he so chooses, after 10 years, he can have me undergo a sex change. Piercings and any other marking are fair game. If I sign that contract, I agree to all that. AND, I agree that I will serve him for life. There's no out clause unless, at some point, we came to a mutual agreement that it should end. Should he decide to "fire me," I'll get a payment of $25,000 as severance. That likely wouldn't be much, however, as he'll be turning me into a whole new person. In return for me signing, the contract states that he will supply all of my food, dress and room for life. Of course, he gets to choose everything I eat and dress in, as well as where I live. And there I am standing in front of him. Six-inch heels, a mini skirt that barely covers anything. Fishnet stockings. Slutty makeup and a belly-shirt that says "slut" on it. My choice is to sign the paper and get on my knees and suck his cock or walk out. He even put a blindfold on so he couldn't see. I stood there for what seemed like hours. Then I put my name on the contract and got on my knees. I took a deep breath and took his cock in my mouth... getting used to a position I would be in often for the rest of my life. --- E-mail Mikhayla with ideas for other stories! Becoming a Sissy Slave since I started dating my wife she has always known that I love to wear panties and other items of lingerie, she did not really like it but let me do it as long as she did not have to see me in it. When she was at work or out with friends I would rush to get dressed in the sexiest things I owned and would prance around the house and eventually masturbate into my panties while thinking about serving a dominant woman, hoping my wife would be that dominant woman. One day I was really getting into it and while I had my hand over my erect cock that was in my panties, when i wear lingerie i masturbate like a woman, I like to rub my cock and pretend it is a clit. My other hand was gripping a giant rubber cock and I had my red painted lips wrapped around it and sucking it like the sissy whore I was meant to be. While I was deep throating that giant cock with my eyes closed my wife walked into the room, she has caught me in my panties before but I would just run into the bathroom and finish then come out dressed in my normal clothes. This time was different, I did not hear the bedroom door open and she and her friend that had come over for some drinks were watching me make sweet mouth love to this massive rubber dick. I was licking it and kissing it and sucking on it, moaning and rubbing my tiny cock that was as erect as it could get and inside my panties. Right as I released cum into my panties with this cock down my throat I let out a moan of satisfaction, as I did this her friend let out a yelp of laughter and applauded my performance. My eyes quickly shot open and I saw my wife, who was now getting red in the face, and her friend, who was still clapping and laughing standing in the doorway looking right at me. I struggled to get up and tried to jam the rubber dick into my panties to hide it, since there was so much cum already in there it just slid right out, I bent over to pick it up but my wife just said "Stop, go and change because we need to talk." I ruched into the bathroom and took my lingerie off and left it in the bathroom and rushed to put my guy clothes on. When I came out my wifes friend mentioned I had forgot to take off my makeup and that made me red in the face. I tried to apologize and wanted to go clean up more but my wife put up her hand and told me to just meet her in the kitchen. I ran down stairs not knowing what she would say, I id not know she was bringing a friend over, she would always tell me before so something like this wouldn't happen, of course she had never seen me guzzle a cock like that either. She and her friend came down the stairs and met me in the kitchen, I was sitting at the table and had napkins covered in makeup in front of me, I had tried to clean up but I know i did not get it all. I noticed in her hands were my soiled panties and thought that was weird, I also thought this was the end of my wearing lingerie too. The both sat down in front of me and my wife said, "You know Janet, and now Janet knows you and your secret. Well she has known for a long time but never really believed me, but after seeing you and you love for cocks, well lets just say we were both surprised." "I..I..I didnt know..." I just to tell her I didnt know she was bringing anyone over. "I know you didn't, I brought Janet over because she gave me an idea. At first I thought it was weird that you loved lingerie so much, but put up with it, but Janet told me about a whole other lifestyle for people like you. You are what they call a sissy, well you are going to become one if you are not. You will also become mine and Janets slave." My eyes got bigger and I just looked at the two, I have hoped for something like this for a long time and masturbated to the thought but never in my wildest dreams thought it would come true. "It will not be easy, so I am giving you a couple of options. First, you can continue to be my husband and never wear lingerie again, I mean never, I will leave you in a heartbeat if I catch you in them or even think you are wearing anything like that again. Second, we can get a divorce, it will be mutual, I will not tell anyone what you do or take all of your money, we will split everything we own and never speak of this or to each other again. Then there is third, you become mine and Janets slave. You will do whatever we want whenever we want it. There will be exceptions of course, you still have to go to work, but we plan your days off and as soon as you are out of work you let both of us know and we will tell you what needs to be done. We need an answer within the next fifteen minutes. If you are unable to answer then we go with the divorce option. Is that clear?" "Yes, I understand." I responded. There was not much to think about, I have wanted this forever and now it will come true, I have wanted to be her slave for a long time, but her friends slave too? I am not sure I am ready for that. I thought about my options for a bit and every couple of minutes my wife would tell me how much time I have left. When she finally got to two minutes I spoke up. "I will be yours and Janets slave." I responded. They both looked at each other and nodded and smiled. they did not ask if I was sure or anything like that just looked at me and said, "Good, we were hoping that. Now clean your panties." She said as she threw my soaking wet pink satin panties at me. I went to stand up to take them to the sink to rinse them off but was interrupted, "Where are you going," Janet asked me. "To wash them off," I told her. "First thing slave, it is to wash them of Mistress Janet, and second we want you to lick them clean." My cock started to grow in my pants at her order and I just stood there. "Well, what is taking you so long?" my wife asked. "Eat you cum slave," Janet told me. "Eat it now or you will be punished." I raised the pink material to my face and stuck out my tongue, i lapped at my cum that had filled and soaked through the panties, I had tasted my own cum before but when eating it in front of two women that now own you is a much different occasion. the panties were clean and now my wife said, "What do you have to say now?" I just looked at her and Janet not sure what to do. "Are you going to thank you Mistresses? That is what a properly trained slave would do." "Oh yes, of course, thank you Mistress Janet and Mistress Emily for allowing me to lick my panties clean." They both giggled and then pulled out a piece of paper. "these are some new rules, they can and will change at any time and new ones will be added when we feel they need to be. Got it slave?" My wife asked. "Yes of course." I said. "Look slave, I was your wife when I was watching you suck a rubber dick in our bed, but now I am your Mistress. It is Mistress Emily, Ma'am, Miss, Miss Emily, or whatever the fuck I tell you to call me. The same goes for Janet, do you understand that slave?" My cock got rock hard when she said that. "Yes Mistress Emily, I am so sorry, I should have known better. I apologize to you and Mistress Janet for my disobedience." "Good slave, now there are some things that are changing tonight. First, Janet is staying the night and she is sleeping in my bed, you will sleep on the floor and if we need anything during the night we will wake you and you will fetch it for us. Ok?" "Yes Mistress," was all I could say. "Good, second, your mens clothes are to be worn only at work, you will no longer wear boxers at all, you are going to wear panties all of the time now, sometimes when we feel like having fun you will garters, stocking and bras, or whatever else we feel like making you wear. Ok?" "Yes Mistress" "You are going to make us our meals from now on, all of them. You will have to wake up before up, but do not wake us in the process and have everything ready for us so we do not have to rush in the morning. When we get home you will have dinner made, assuming you will be able to get out of work on time, if not when you get home you will takes your suit off and cook in your panties, right away. Also Janet is not just staying the night, but she is now living with us, which means we have to find a new place for you to sleep, for now it will be on the floor by the bed in case we need you. Ok?" "Yes Mistress." "Good, now take off your clothes and go put on what we laid out for you on our bed." I started to walk away and go up and change, again I was stopped. "Take off your clothes now slave, you do not wear mens clothes in here unless you are going to work and I know you dont work at this hour. Get naked you sissy bitch and go put on your outfit." "Yes Mistress," I said as I dropped my pants and took off my shirt, I slid out of my boxers exposing my erect cock, they both giggled. "Give us your boxers, they are going in the trash tonight." I handed them to Mistress Emily and rushed upstaris. I saw on the bed was a pink ruffled dress with pink panties, on the panties was an embroiderded message. "Property of Mistress Emily and Mistress Janet." My rock hard cock wanted to get harder, but it couldn't, I loved them. I slid them on and the dress and twirled around. I ran downstairs and showed my two Mistresses my outfit. "Good slave, now make us our dinner, we are hungry, we noticed you filled up on cock earlier so don't worry about making yourself anything. Just remember tonight you just became our sissy slave." "Yes Mistress Emily, I understand, thank you Mistress Emily and Mistress Janet for making me your slave."