My first time as Kara (m/cd) (x-post) | 2016

Kara Finally This is my first attempt, sorry if it isn’t very good. It is a true story as best as I can describe it from a few years ago. I would love some feedback or just to chat more about it! I used to be a good boy. I was married, but she cheated and left me. After my divorce I was cleaning out my house getting ready to move when I found a box of my ex wife’s clothes, there was a little bit of everything in there. I figured I would itemize and donate them for a tax credit. Sorting through the box I came across lingerie, pjs, dresses, skirts, bras, panties, and yoga pants among other items. I sorted and itemized everything and then re packed the box to get ready to take to the thrift store. I was pretty down after going through her things and decided I would have some alcohol as had become my routine. It was cold and icy outside so I stayed in and had a quick bite and continued my boozing. Around 9 pm I went back to the bed room and remembered the clothes. Now to be honest I had been looking at some porn and was a little horny when I came across the stash. I started looking through the lingerie and remembering the good times. I was getting drunk and horny…. dangerous times for sure. I took a shower and when I got dried off the temptation overtook me and I put on some of her clothes. I loved the way the satin felt on my skin. I would do this from time to time over the next few weeks. I even ordered a few things for myself. I decided a brunette wig and some makeup would help. I don’t know why I was doing it, it just seemed to become a hobby. Obviously the orgasms were very intense and I took to adding cd porn to my diet as well. I found myself diving deeper into CD boards and forums, discussions, chat rooms, all the while dressed fully at home. I had taken to keeping my legs shaven from the knee up, my chest shaven, and obviously my cock, balls, and ass! I started chatting to other CDs on messenger, and sharing some pics I had made with them. Some would ask if I had ever played dressed up or ventured out which I could honestly say no I had not. Now a brief back story – in college I had one bi experience in a MMF threesome one night. Mostly just some touching, although I did manage to lick him a little while I was 69 the girl and he took her from behind… So the chatting continued and I even started browsing some of the ads on the back page and craigslist when I was really horny. I would occasionally email the guys just looking for chat really. Some were only looking for a then and now fuck, others glad to chat. I started chatting with one man, a little older than me ( I was late 20’s, he was close to 40), and we communicated on email and ymessenger for a couple of weeks. He would always address me as my CD name that he gave me – Kara. He made me describe my previous sex life, my (lack of) experience with men and why I found dressing so sexy. As with many of these chat sessions, I would usually have some wine or mixed drink and continued to become aroused. He would always ask when I would suck his cock for him to which I would sheepishly dance around the issue and he graciously never pursued. It was one particular night, I was home, and feeling especially horny. I had just received some new lingerie and a frayed denim skirt. I had showered, shaved, and was trying them on when my phone beeped with the messenger I had on it. It was the guy I was talking with. I had told him about the new clothes, in fact he helped pick them out online with me. He asked what they looked like and so I sent him a pic. He said that wasn’t enough, he wanted to see in person. I told him I wasn’t sure about that. We kept chatting, and I could tell he was being more persistent than normal. I was drawn to his dominance all of a sudden. I told him I was not ready for physical contact but if he would agree to look and no touch I would consider it. He agreed to behave and we set a time for him to come over. I was nervous as hell. I was dressed in a black thong and water bra (gving the illusion of cleavage), thigh high stockings, a denim skirt, corset top, and heels. I had my brunette wig on and drawn in a ponytail. I had done my best with the make up I had. I had even painted my nails. I can’t say that I looked like a passable girl, but I thought to myself “not bad.” I was working my way through some wine, when the doorbell finally rang. The lights were low and I had a couple of candles lit as per his request. I opened the door cautiously, my hands were shaking, but I was not turning back now. He introduced himself as Jim, and said “I’m glad to finally meet you Kara.” I opened the door and let him in. “Would you like anything to drink?” I offered in my whispered voice, and he asked for a jack and coke. “Sure thing! Why don’t you have a seat in the den and I will make it for you.” I brought him his drink in the candle lit room and he accepted it and took a sip. I sipped my wine and he said “Well, turn around so I can see.” I turned slowly, he interrupted me saying “ You are too far away, I can’t see, come closer.” I cautiously, without speaking followed his instructions. “Good,” he said quietly, “now turn again.” Then he broke rule number one. As I turned he reached out his hand and let it slide up my calf and thigh and over my ass. I was a little startled at first but I thought, “ok innocent enough, no worries” But then he didn’t move his hand away and just slide it all the way up my back and down again. He was complimenting my attire and saying how he loved my sexy legs and ass in the skirt. He said “Mind if I see what’s under this skirt?” But he wasn’t asking, while he spoke he was pushing the skirt up to see the thong and garter. It was electric when his hand touched my skin and I realized that there would be no more rules. I continued turning and saw that while one of his hands was exploring me, the other was rubbing his bulge through his slacks. “Did I do that to you Sir?” I asked in a whisper to which he acknowledged and pulled my hand to feel it. It was the first time I had actually put my hands on another cock. He rubbed my hand up and down his length some and I finally said “ You can take it out and stroke while you watch if you like.” I was trying to get control over how fast this was going. He replied “No Kara, you can take it out and stroke it.” Even though I wasn’t ready, I was compelled to follow his instructions. I lowered my self to my knees and watched as my hands, which were now Kara’s hands finally, began to undo his belt and slacks. He raised up and I slid his pants and boxers down exposing a smooth, erect cock, about the same size as mine. I was captured and overtaken with Kara’s lust at that point. I remember the heat of his cock when I first touched it. I slid my hand up and down slow, feeling his balls and hard shaft. “MMMM yes Kara,” he moaned as my hands wrapped around his length. I stroked him some, and then he stopped me and said “It would feel a lot better wet Kara.” I wasn’t’ sure I was ready but before I could protest he was pulling my head towards his cock. For whatever reason, my lips parted and he guided my head over his cock. He was clean, fresh from the shower and it was delicious. I did not need much more encouragement before I was sucking and stroking him, letting him hump my mouth while he sipped he drink. I felt so slutty and loved it. I alternated licking his balls and cock until he was getting close. He stopped me saying “I am close, where do you want my cum?” I told him to cum anywhere he wanted. He pushed my head back on his cock and I knew I would be swallowing my first load soon. I sucked him and played with his balls for a few more minutes before I felt him tense and felt a jet of his cum hit my throat. I swallowed all I could and didn’t spill any. I continued to lick and clean his cum while he finished his drink. He thanked me for being a good girl and started to get dressed. I knew I would taste him again soon. And I did- - but that is another story. If you like I will be glad to write about it.