A Crossdressing Story


A Crossdressing Story***A crossdressing story***(All characters are fictitious…maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her husband travelled a lot and so she had a good deal of privacy in her home and she confided that she had done this with a friend who was also a TV. Her letter had a photo showing her to be a cute brunette, with a nice firm figure and tastes in clothing that stopped just short of looking slutty. I was trying to get the semi-slut look down myself and being a brunette, I figured she could really help transform me. Besides, she had made it very clear she was interested in “playing around” with her pupil. I called her and we arranged to have me come over after her husband had left on one of his trips. I looked forward to that day very much and it soon arrived. I drove over to her house dressed, because we did not want her neighbours to “get the wrong idea” with her husband gone and all. She greeted me at the door and said, “Not a bad attempt, but we have a lot of work ahead of us.” I was grateful for the attention and had to admit it was true or else I would not have visited. For her part, she was dressed in spandex bikers pants, a t-shirt and bare-footed. She explained that we would start dressing together, from the ground up. We spent the next couple of days going over the basics of makeup, hair, even how to walk. She was an excellent teacher and her price was easy to meet. She wanted me to have sex with her as her lesbian lover and I had no problem with that. We would get completely dressed and then sit together as though we had just met at a bar. I would walk into the room and approach her, trying to pick her up. “Hi, I couldn’t help but notice you were alone here, mind if I join you?” I would say. She would make small talk and flirt and finally I suggest that we go back to my place for a drink. She always wanted to protest that she was not interested in anything sexual. Part of the fantasy was that she was to be seduced into lesbian sex gaziosmanpaşa escort by me. After a couple of times we had our routine down. Everything was going fine until the day before her husband was to return. We had entered the bed room and I began by sitting too close to her, making her aware of my body against hers. She blushed and tried to move away and I slowly slid my hand up her thigh, playing with her inner thighs by lightly stroking there. She gasped and I moved my other hand up to her breasts. Through her blouse I was able to stroke her breasts gently. I brought my mouth over to her ear and started to lick her ear and the nape of her neck. She always had to protest, but her protest were never enough and her body betrayed her. I got my had far enough up her short skirt to realize there was no underwear and began to make slow passes with my finger over her moist and tender pussy. Her mouth parted in a soft moan and my tongue slid from her neck to her lips. The taste of our lipstick mixed in my mouth as my tongue searched for her tongue. I stood up and faced her, both hands on her breasts. I gently forced her back onto the bed and knelt in front of her knees. Raising her skirt, I began to slowly lick my way up to the parted and wet lips of her vagina. Just then the garage door started to open. We both jumped up and looked at each other. She said, “That must be my husband, he wasn’t supposed to be home until tomorrow.” The thought of being caught had never crossed my mind, but this would be exciting-the ultimate test of our work in dressing me. We headed out into the living room and Debbi lit a cigarette while we sat there waiting for Paul to enter the house. What a pair we must have made! Debbi had a flushed look because of the arousal and we were both dressed like women on the prowl. Debbi was wearing a black leather mini, dark hose, 3inch heels and a sheer silk blouse. She was sitting there with her legs crossed, heavily made up, a cigarette between her bright red lips. I was in a short skirt, tight top (made to show my “tits” off), red hose and red high heels. And Debbi had done an excellent job with my hair and makeup. We both knew I could pass, but we had to get me out of there without too much talking. Well in walks Paul (he is about 6’1″ and strong as apposed zeytinburnu escort to my 5’6″ and feminine build) explaining he had finished his business early and decided to fly home to surprise Debbi (which he really had!). He asked her to get him a drink, after being introduced to me (Mikki). I loved the way his eyes went all over me and could tell he was trying to mentally undress me (I figure he must have left a few parts out, in his vision however). Debbi said they were all out of beer and asked me to run to the store. Well Paul would not hear of the guest going out for refreshments and told Debbi that she should do it, since he had been traveling all day. Debbi was worried and gave me a “Be careful” look but left anyway. As soon as she was gone, Paul sat down close to me on the couch and tried to hit on me. I should have seen it coming, but he really laid it on thick. Before I knew it, his had was on my knee and heading up. I tried to protest, but he just said, “With the look you have got, I know you are looking for some.” I protested, but the next thing I knew he had his hand all the way up my skirt and on my dick. He jumped back and said, “You’re a guy?” Well, I tried to get up but he pinned me and dragged me off to the bedroom. He tossed me on the bed while he grabbed the handcuffs he and Debbi used sometimes. The next thing I know he has me handcuff to the bed and says, “We’re going to get to the bottom of this, in more ways than one when Debbi gets back.” Debbi came back and got the surprise of her life. Paul was not a mean guy or physically abusive, but he was pissed off now and had dragged Debbi back to the bedroom too. We explained what was up and he just looked at us. Then he said, “Well, if Mikki wants to be feminized so badly, I am sure we can keep helping.” Now I did not know how to take this but the way he said it was not harsh and I started to hope. Paul said that the way he saw it, lesbian sex was just me having sex with a woman like usual, just dressed different. If I wanted to be a real girl I need to do him. I had never had a bi experience and the thought scared me. But he was not offering this as a choice, I realized. I was ordered onto my knees, after being un-cuffed. Paul got Debbi over there too and order her to show me how suck and then to let me take sultangazi escort over. Debbi used her tongue in slow strokes on his large dick, working it from the tip to the base as she used her hand to stroke the dick and other had to massage Paul’s balls. She then backed up and told me to go for it. I was timid at first and started to lick it, not really touching it much. Then Paul took my head and slid his cock right into my mouth! The thing was big and salty, but I just started sucking. I used my hands on his balls, hoping that he would tell me before he came. No such luck! He arced his back and the next thing I knew, there was a load of cum shooting into my mouth, dribbling down my chin and onto my blouse. He said, “That was good for starters, but we have got more to do later.” He left us two in the bedroom and went to get a beer. I thought about running out, but besides the way I looked, I was aroused. I had gotten a guy off, as a woman. I was really beginning to get turned on. I could tell Debbi was already hot (she had confided to me that she had always wanted a three-way and I guess now she was getting one). We started to play with each other and once again my face was buried in her pussy. Paul quietly walked in on us. I did not know he was there until I felt a hand on my ass. He told us to keep on going and he stood there watching me eat his wife until she came. This had gotten him rock hard again and I noticed had a jar in his hand. He walked over to me and told me to bend over. I was so turned on that I did not card what he was going to do, I just needed to get off! He slid his hands over my back and took my skirt off, then my panties, leaving me in heels and stockings from the waist down. Then he proceeded to grease my ass with Vaseline. I knew what was coming and I was hard too. He came up behind me as I knelt there, put a hand on my shoulder and slid his big, throbbing cock up into my ass. He fucked my ass for a long time and I could feel him groaning and his hot breath on my neck with each thrust. He really got into it and started to lick my neck and then I felt his hot tongue in my ear. The next thing I felt was his tongue on the side of my mouth and I turned my head to kiss him. I felt him tense at that moment and my ass filled with cum as he let loose in me. I couldn’t stand it and just brushed my own cock and that was enough. I let loose a load of cum as my ass throbbed with the mixture of sensations of Paul’s dick, my orgasm and the juicy feel of hot cum. That was my first real experience with cross-dressing with other people present, and I was hooked from that day forward. We had all enjoyed ourselves so much that first time that decided to make our threesome a permanent one.

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