Gay Sissy Fucked For The First Time

This is a true story about the first time that I had gay sex as a Sissy. I love to crossdress, I am gay and a Bottom. I also have a huge latex fetish and, at the time this story took place, was not new to having rubber sex and being fucked by other Rubbermen, However, I had never had sex while crossdressed. This is about the first time that I was fucked as a Sissy in full drag.I was reading the dating page in one of those local add papers. There were sections for men looking for women, women looking for men and 'others'. I saw a listing by a CD who lived about two hours away looking for a man or another CD and answered it. We arranged to meet at his place after work on a Friday night. As it would be a late meeting, I would be spending the night. He knew that I loved to cross dress and had played with guys before, but never en femme. He said that he would be dressed when I arrived and to call when I pulled in so that he would know that it was me before he answered the door. When he let me in he was wearing a pair of sheer white transparent nylon panties and a matching bra, sheer powder blue hold up thigh high nylons and a matching sheer nightie that just reached the tops of his stockings and a pair of shiny white heels and holding a bunch of flowers and a bottle of wine for me. He had hair that was rather long for a guy, although not long enough that it could have been worn in a ponytail, but he had combed it in a rather girly fashion for our meeting. He wore no makeup but his whole 5'6 ' 125-pound body was shaved smooth. Even if I couldn't have seen his crotch through his sheer outfit, by his male face and no breasts made it obvious that he was not a girl. Being smooth shaved, dressed like that and plainly a guy only served to make it more kinky and erotic and I was already getting hard! As he closed the door behind me, still holding the wine and flowesr, he wrapped his arms around my neck and gave me a light kiss on the lips. I pulled him close in a hug and, as our bodies pressed together, he could feel my hardon against him. He said, "Mmmm, maybe you should get changed!" I took my bag and he showed me to the bathroom. I have a huge latex fetish and this was going to be a rubber night for me! I striped and, as my body was freshly shaved before leaving home, I used the adhesive to glue on my silicone breast forms. I slipped into a tight, thin black latex catsuit and pulled up the back zip. that particular suit was footed but the gloves were not attached. I had no crotch zip, just a small opening that I could pull my cock and balls out through and a small inch and a half anal slit, so I pulled on my red latex bikini panties over the catsuit. Over that I put on my long sleeve black latex mini dress. I went to work on my makeup; false eyelashes, foundation, light rouge high on my cheek bones, eyeliner and eyeshadow and a splash of perfume; musk. Lastly, I attached my sholder length curly wig. For the final touch to my outfit I pulled on my shoulder length red latex gloves and red latex boots. These boots are long gone and I wish that I could find another pair like them. They were thigh highs made by a company called Latexa and were unlined rubber pull ons, like a slightly thicker molded latex stocking that covered the whloe one inch platform sloe and chunky four inch heel in seamlell one peice molded latex. I just loved those boots! I tottered out in my best girly walk and found him sitting on the couch, wine opened, two glasses, one nylon leg crossed over the other with a high heel hanging from his toes, watching a Sissy porn video and his hardon bulging his sheer panties. He told me that he had never worn latex but loved how I looked and couldn't wait to feel my rubber covered body next to his! I sat next to him as we sipped the wine, watched the movie and petted each other. It wasn't long before we were no longer paying attention to the movie and were sucking tongue and fondling each other. I needed to see and feel his naked cock so I got down between his legs. He lifted his hips and, as I pulled his panties down, his cock sprang free. It wasn't too large, maybe a little over six inches and not too thick, but his hairless balls and rock hard meat looked absolutely delicious to me! As I stroked it with my rubber gloved hand, a clear drop of pre-cum formed at the slit. I touched it to to the tip of my tongue and savored the slightly salty taste and then took the whole thing into my mouth and started sucking. He held my head amd moand as he started humping and fucking my face. As the yummy pre-cum starts to flow, I like to stop for a minute sometime and just lightly hold the crown with my teeth and try to stick the tip of my tongue in the slit. I know how maddening that feels!He told me that I was going to mahe him cum! I told him not yet! I grabed the lube from my bag, him by the hand and pulled him behind me to the bedroom. I handed him a condom and while he put it on I took ff my rubber panties, lay on my back, lubed my sissy cunt and told him to fuck me hard! His cock, being not too thick, was just right to really feel inside me but still slip right in. The head popped through my ring and he sunk in all the way to his balls on the first first thrust! OMG, how I love a cock in my ass! I wrapped my rubber booted legs around the small of his back and told him to not worry about lasting, to just fuck me hard and pound my sissy ass! As it turned out, I was so horny, felt so naughty and kinky getting fucked as a sissy slut by a guy that I had just met that I came before he did in about five minutes of feeling his cock sawing in and out of my sissy hole. I just love to cum first and feel my ring clamping down in orgasmic soasms on a hard cock! And cum I did! I had also put on a condom in hopes it would happen like this. My latex cleans easily but I didn't want to mess his nylon outfit. My body went rigid, my pussy hole clutched and gripped on his hard cock and I filled my condom with a really nice load. The feeling of my cunt tightening up and milking his cock must have did it for him too. He laid the weight of his body on mine, hugged me close, made another dozen or so hard jabs up my ass then rammed it up me hard and, while holding it deep inside me his body started to jerk while his cock pulsed and he unloded his balls into the condom. I ended up not just staying the night, but the whe whole weekend and he fucked me several more times. I love to bottom and he liked to top but, I did fuck him once that weekend and made him come once with my mouth. I don't remember all the details of every time I have been fucked, (too many to remember) but I remember in vivid detail that first time as a Sissy! He lives far enough away that we evevtually developed other interests in playmates. We got together for a couple of years and after the third time we started doing it bareback and shootin his load up my ass. Oh, how I love being bread raw and filled with cum!!! I have had two bareback relationships. My current buddy gives me his load up my ass, but that guy was my first.Riki