Date: Wed, 20 May 2009 21:11:55 -0700 (PDT) From: Dee Groove Subject: The Night That Almost Was Transgender / Transsexual I am a cross dresser and I had an arrangement to meet with a beautiful CD at a local motel. For weeks we planned our meeting and what was going to take place. Daphney is a wonderful lady with a fantastic and huge cock. I am Sindee and this was to be my first time with another person with a cock. I have a wonderful Mistress that set us up and I was so excited that I was going to become a full woman. Becoming a full woman meant that I had to suck my first cock and let her cum in my mouth, let her fuck me in my ass (wearing a rubber of course), let her suck my cock and if all went well I was even going to fuck her in her ass. We were going to do lots of kissing and maybe even some cum swapping. I had saved several loads of cum in a rubber, which I had frozen and was going to bring to the motel that night. Mistress Daphney was going to take the role of Dom and I was going to be her Sissy Slut. She told me that I may drink the cum from the rubber or she might pour it into her mouth just prior to our first kiss, at which time she would let me take the cum from her and swallow all of it. Then use my tongue to clean out her mouth as we french kissed. My orders were to wear my garter, nylons and new thong to the motel underneath my man clothes. I was to bring my bra and all my toys in a bag for us to play with. I call Mistress and she tells me which room to go to, the door is not locked. I go inside and as soon as I enter I remove all my outer clothing. I am standing in front of a total stranger who I can barley see in the dim light, but I can see that she is finely dressed in a dominant outfit. I can see she doesn't have any panties on because her huge cock is standing partially erect, it looked like it was about ten inches long, much larger than my puny sissy clit. I reach into my bag and take out my new pink lacy bra and put it on, I am nervous and fumble with putting it on. She makes fun of me calling me a clumsy slut and to hurry if I knew what was good for me. I got the bra on and was ordered to drop to my knees and crawl over to where she was sitting. She ordered me to worship her boots; they were beautiful black boots that went half way up her beautiful thighs. I placed my lips on her boots and started kissing them and telling her how wonderful they were. I kept this up and slowly worked my way up to the top of the boots. Mistress told me to stop and slid forward in her chair, she took her huge clit in her hand and started rubbing the head against my lips; pre cum was really dripping from it so I eagerly licked it clean. She then slapped my face with her clit several times and told me to beg her to allow me to suck on it. I started begging, Mistress please let this worthless sissy slut suck on your wonderful clitty. I kept it up for several minutes when she said shut up slut. She then took out some wrist cuffs and ankle cuffs and placed them on me, then tied my hands down to my ankles. I was now at her complete mercy. She stood up and placed a blindfold on me, it felt like it was a pair of her nylons, now I was blind and tied up. I could hear her walking around me, making fun of my six in clit and telling me I couldn't fuck anything but my hand with a little thing like that. She was really humiliating me. She told me that if she was with my wife, she would fuck her while I watched and when she was done fucking her I would be allowed to clean her cock and then clean all that wonderful cum from my wife's pussy, and there would be lots of it. I told her I would be very happy to clean her cock and then my wife's pussy after she fucked her properly and begged her to let me suck on her cock. She said in due time, but not quite yet. She pushed my head to the floor, which put my ass pointing into the air, there was only one reason she would do that, and I figured she was going to fuck me in the ass. Instead, she ripped my panties down and spread my cheeks as far as she could. I then felt something cold being applied to my ass and she was rubbing it into my asshole and all around it. She would reach under and rub my throbbing cock and my balls until I thought I was going to cum. Just then I felt the heat starting to spread first from my ass and then my balls and cock. She had spread Ben Gay on me, and lots of it. She then told me that it was going to be my lubricant for my next act. She reached into my bag and pulled out my nine-inch dildo and slowly started working it into my burning ass. The heat had me going, and I could feel the tip of the dildo slip past my sphincter ring. She slowly inserted all the way in and started pumping it in and out. I didn't know but she had placed a plate under my cock to catch the "milk" that I was pouring out of my erect cock. I was being milked and didn't even know it. She kept fucking me with the dildo for probably ten minutes and suddenly pulled it out, I groaned and begged her to keep going. She said I really was a slut and would get the real thing later. She then got my butt plug from my bag and without warning inserted it into my empty ass. She said it was going to stay in until she was ready to fuck my virgin ass with her huge cock. So when I felt it being removed, I would know it was time for me to become a woman. After the plug was in, she took several clothespins from my bag and placed them on my balls, I guessed there was about ten from the burning they were causing. She asked if I brought my riding crops and other spanking tools and I said yes mistress, they were all in the bag. I had brought two riding crops, a ping-pong paddle, two homemade floggers and a ruler. She asked if I brought my nipple clamps, which of course I did, I don't make a trip without them. They are the good Japanese clover clamps. Two are hooked with a chain and there are six that are separate. She took the ones on the chain and placed one on each of my nipples, it really hurt so good. I love to have my nipples played with real hard. She then placed two more of the clover clamps on each nipple, one on each side of the clamp in the middle. Now my nipples were really feeling the burn and I moaned out load. She then placed my blonde wig on me and took out my red lipstick and started putting it on my lips. She told me she wanted me to look the part of a real slut. She applied some eye makeup and some blush and some mascara. I have naturally long eyelashes so they usually look good with mascara on. She then told me she was going to gag me because she was going to give me a nice spanking. I felt what I figured out to be a penis gag being placed into my mouth and then tied in place. I really wanted to cum and she knew it, she reached behind me and fucked me with my butt plug a few times, which made more milk pour onto the plate. She slapped my face a few times with her beautiful cock and then I felt the first of what was going to be many slaps on my ass. She was using the crop, I knew from the many spankings I had received with it at the hands of my wife, but she was hitting me much harder than my wife ever did. She said would my slut like me to slap the clothespins off of my balls with the crop. I shook my head no, because I knew how much it would hurt. It hurt enough just having them taken off one at a time. She said good, I'm glad you want me to spank you until we get all of the clamps off. The next one landed on one of the clamps and it went flying off and I felt a surge of fire coming from my balls, it felt like part of them was being ripped off. Again and again she struck the clamps, occasionally landing a blow right on the balls. When she hit my balls, I almost passed out, and tears came to my eyes. She then said, you still have four clamps on, if you cold talk; I would let you beg me to spank the rest of them off. Would you like me to leave them on, I shook my head no. Good she said, that means you want me to continue spanking them off and again and again she slapped at them. It must have taken another thirty or so hits and finally she said there was only one left, I couldn't tell because my balls were so sore it felt as if they were all still on. She reached down and released the clamp only to let it clamp back on, I actually started to cry. She then reached under my bra and released one clamp at a time only to let it too fall back on each nipple. I couldn't believe the pain in my nipples now, I forgot about my balls for a minute. After she did this to both of my tits, she reached down and took off the clamp on my balls. Tears were freely running down my face. She laughed and called me a sissy. All the time she was doing this, I could tell she was taking pictures. We had arranged for pictures to be taken with both of our cameras so we would both have a good record of my becoming a real woman. She then reached down and took out my plug. Here we go I thought, my ass is going to be filled with that huge cock. I'm sure it was twice as big as my dildo and bigger around than my butt plug. Instead, she placed another dildo in only this time it wasn't mine it was one of hers. She then pulled me up so I was sitting back on the dildo forcing it deeper into my ass. She then took of the gag and said open up. She asked if I was thirsty which I was and I said yes Mistress I would love a drink. She then took the rubber I brought and poured it into my mouth and said there swallow that. I did and then she leaned over and kissed me full on the mouth. It was my first kiss with a man and it felt different but not bad, she stuck her tongue into my mouth and we French kissed for a couple of minutes. She asked if I was still thirsty and I said yes Mistress I am. She then stood in front of me and placed her huge erect cock into my mouth and said to start sucking. This was my first blowjob. She said if I was really thirsty, she could give me some golden nectar. Just as I started to shake my head no, I felt her starting to pee into my mouth. I was so hot and horny and ready for anything, but this caught me by surprise and some started running out of my mouth. She slapped my face and said drink it or she had a dildo that was twice the size of the one in my ass. I started to swallow as much of her golden nectar as I could, it was bitter but I really was thirsty and it helped a little. She then stopped peeing and said ok now suck. She untied my right hand so I could feel her cock and balls and to help pump her cock with it. I could only fit about half of it into my mouth. She called me a worthless sissy slut and said that any good sissy could deep throat her cock. I tried and gagged and almost threw up. She pulled out a little and slowly slid it back in. She told me how to work around the gag reflex and slowly kept putting a little more at a time down my throat. I was pumping her cock with my hand and sucking as good as I could, after all this was the first cock I have ever had in my mouth. She told me to get ready for a real treat and pulled her cock back until just the head was inside my mouth, I kept jacking her cock and sucking on the head and then it happened. I felt the first hot blast of cum as it hit the inside of my mouth. I figured I could hold all of it in my mouth but there was no way, she was cumming and cumming. She told me not to swallow yet and pulled out and told me to tilt my head back, she took over jacking her cock and I just sat there with a huge dildo up my ass, my mouth wide open, almost completely full of cum. She said she wanted a picture so she grabbed the cameras and took lots of pictures. Actually she had been taking pictures the entire time I was sucking her beautiful cock. Finally the cum stopped pumping from the tip of that huge cock and it just kind of just hung there in a couple of huge white strings of cum. She told me to close my mouth and still not swallow, I was to swish it back and forth, even gargle a little with it, all the while she was taking pictures. Then finally she said ok sissy slut, swallow that wonderful load of protein, which I did without hesitation. It tasted much like mine, maybe a little different, but lots more of it. She then reached down and started stroking my tiny clit and told me I could cum if I wanted. The problem was, I had been milked almost dry and couldn't cum if I wanted to, at least not yet. I asked my Mistress if she could remove my nipple clamps, and she removed the two on either side of the center main clamps. As the blood rushed back into the nipple, the pain was intense. I started to moan too loud and she stuck her softening cock back into my mouth. She then said ok slut, start sucking until your nipples feel good again. I sucked and sucked and her cock got about half hard again. She pulled it out and did another thing that caught me off guard. She helped me to lye back onto my back, which left my legs spread, and my ass with the dildo sticking out in plain view. I couldn't help but think I can't wait to see pictures of how I looked in this position. She stuck her cock back into my mouth and turned around into the 69 position and took my tiny cock into her mouth. She had no problem taking the entire thing into her mouth and I felt her lips pressing against my bare skin. I didn't mention that I keep my cock and balls and ass shaved at all times. She asked if I could cum and I could only shrug as if to say I don't know. She laughed and said too bad slut, by this time her cock was hard as a rock again. She reached down and slowly slid the dildo out of my asshole. She then took off my blindfold and said I needed to watch this. She somehow had the camera set to take automatic pictures, so it was taking pictures about every five seconds and had it on a tripod. It also had a line running from it to a TV, she could watch everything being done on the big screen TV, which was also being recorded on DVD. She placed a rubber in my right hand and told me to slip it onto her cock, as I slowly rolled it down over the head and down the shaft, I kept thinking that now I was going to be a woman, I was going to take that huge cock up my ass. With the rubber on, she applied some lubricant on her cock and placed a bunch on and into my already stretched ass. I could feel as the tip of her cock began to press against my ass, it soon popped inside me, I could tell it felt a lot different than the dildo. It was somehow softer but it was also much larger. She was gentle with me and slowly worked her cock in and out, slowly going deeper and deeper until she was completely buried in my ass. I looked and noticed my cock was pouring pre cum from it and was rock hard. She pumped for several minutes until she was about to cum. She knew I wanted to feel her cum on my cock so when the time came, she pulled out and had me remove the rubber from her cock and then I was allowed to jack that wonderful cock off until it shot another huge load of cum right onto my cock and all over my balls and stomach, filling my belly button. She had a spoon and used it to scrape the cum from me and fed it to me like a little baby. After I had eaten all the cum she could scrape up, she slid up and placed her softening cock into my mouth again and told me to clean it up. I could taste the remnants of the Ben Gay but it wasn't bad. I sucked it clean and she slipped it out of my mouth. Ok slut she said, you still need one more thing to become a real woman, you need to know how another ass feels. This is something I had never even done with my wife. As much as I loved playing with and licking my wife's ass, I had never been allowed to fuck her ass. She simply slid a little higher and let me suck on her balls for a minute or two then moved forward a little further until her puckered ass was right over my mouth. Ok, slut, start licking. I slowly started licking around her sphincter. She had let her hair grow back for a while and her ass was getting pretty hairy. It was real clean and smelled like sex. I didn't care, I started rimming her ass for all I could and slowly started sticking my tongue into her ass as far as I could and was actually fucking her with my tongue. Oh the reels wonderful my slut, I might have to use you again and again. You are mine from now on you sissy slut. She then pulled off my face and slid down my face again and continued down to my cock. She took out a rubber and rolled it onto my cock, it looked like it still had half of it to unroll when it hit the base of my cock. She then lubed up my cock and slowly slid her as onto it. She was right; it was tight, much different than a cunt, but not so tight as to be uncomfortable. In about two minutes I started to moan saying I needed to cum and she started to slam down on my cock, she then reached up and removed my other two clamps on my nipples, that was enough. I blew what cum I could into the rubber but to my surprise my cock stayed hard. She pulled off and then called me a woman and said I had made it. She then slipped the rubber off of my cock and reached up and poured the cum from the rubber into my mouth. She told me to get used to the fact that any cum that came from either of our cocks was going to be eaten up by me. I was now her cum slut sissy. I was hot and sweaty with my wig on and needed to shower before I could go home. I went into the bathroom and before long; Mistress was there in the shower with me. For the next half hour we cleaned each other and I took one more opportunity to suck her beautiful cock until she came again and this time I took the cum into my mouth and swallowed it eagerly. We finished the shower and got dressed. My ass was sore, my balls were sore but my cock felt wonderful. I packed up my stuff and we talked for a few minutes, I was surprised that I didn't feel that bad, a little guilty but not too bad. We made arrangements to go shopping for me some clothes. She told me she was going to be dressed as a man and I was going to try on a lot of clothes, there would be no doubt that the clothes we were looking at were going to be for me including some high heels. Next time we were going to meet for some kinky fun, I was going to go completely dressed as a slut and we would go to dinner first then to the motel. Oh and I was to buy a chastity device, like the curve and she would lock it in place and only she would have the key. I asked how I would explain it to my wife and she said that was my problem. Well that ends this night, and begins to set up for the next time. I am excited and can hardly wait. As it turned out, this was only in my dreams. Signed, Sissy Slut Sindee (finally a woman)