Hot Italian neighbor
- April 29th, 2009
- Posted in Hot erotic stories
Before I left my Moms house to live on my own we used to watch our neighbors house for them when they went away on vacation. My Mom would send me in the house to make sure that everything was alright inside, and that the heat was on, and so fourth. One day as my Mom was going to work she told me to be sure and check the house before I go out and as usual I did but this time I did something that I had always dreamed of doing. I was going to go through my neighbors lingerie draws and try on her things, Yes I am a comfirmed crossdresser and I was in heaven. My neighbor was a beautiful Italian woman who would turn heads like I can’t tell you. Not only did she have a body to die for, but the clothes to match, and I was about to wear some of her things without anyone knowing. I first decided that I should shower first so I went into the bathroom and began to shower myself with all of her wonderful smelling bath gels, and shampoo. I got out of the shower and dried off and grabbed her robe that was hanging behind the door, it was a beautiful black silk robe that still smelled of her and her purfumes, I almost lost it right there and then when I felt the silk robe up against my skin, it felt wonderful, and kinky at the same time. I went into the bedroom and open up her drawers until I came upon her lingerie. I took out a beautiful black bra, panties, Garter belt, and Black back seamed stockings. I was in heaven. I began to dress all the while fighting with the thought of playing with myself before I even finished getting everything on. After I had all of the lingerie on I went into her walk in closet and started imagining what it would be like to put on a dress as well. I am only 5′8″ and have a small frame and I figured that I would be able to find something that I would fit into. You see I never had gone this far before and I wasn’t about to stop at this point. I went in and found this beautiful cocktail dress that had a slit up the thigh on one side so I took it by the hanger and held it to my body and it seemed that it would fit and just as I was about to walk out I noticed some boxes on the top shelf I reached up and took one down and opened it up and inside was a georgous long brown haired wig, I couldn’t take it anymore I was about to transform myself into a beautiful women in my neighbors bedroom. I went over to her vanity and pulled the wig out of the box and I carefully placed it on my head, I then looked in the mirror and could not believe that it was me. I then began to apply some of her makeup to my face, I put on lipstick, lip liner, eye shadow, eye liner, blush, blending powders, and then I even rubbed in a little of her perfume. I got up and went back into the closet and put on the dress in front of the full length mirror and I couldn’t believe that it was me pulling the dress down over my head, I looked and felt like a women for the first time the sensations were driving me over the edge and it showed.I bent down and picked up a pair of black stillettos and put them on my feet and to my surprise they fit, a little tight but they fit. I was standing in front of the mirror for some time fixing, and adjusting everything and enjoying all the new feelings that Iwas experiencing I was touching myself all over, running my hands up and down my body savoring every touch, and feel when all of a sudden I heard something outside in the bedroom I walked out of the closet to find my next door neighbor standing at the entrance to the bedroom. I wanted to die, here I was dressed in her clothes and so totally embarrassed I wanted to jump out of my skin. Then the thought of her husband seeing me like this was to much to bear so I started to plead with her to let me get out before he see’s me dressed like this, I was apoligizing up, and down saying that i was sorry and I started to take off the wig when she assured me that her husband wouldn’t see me as she had come home a day ahead of him and that he was still in Florida. She walked towards me and told me to leave everything on, she even reached up and fixed the wig that I was taking off. She asked me if this was the first time that Iwore her things, and I said yes. She asked me if I liked being dressed as a women, and I said yes. She reached out for my hand and sat me at the vanity again and said to me I going to fix your makeup and make you look real pretty OK, what was I to say she was being real cool about the whole thing and helping transform me into a beautiful looking woman. She rubbed, and patted, and brushed, and then fixed my lipstick, and brushed my hair out. She then stood me up and told me to go in the mirror again to look at myself but before I did she sprayed me again with some more perfume and said to me, there now your done. I walked back into the closet and could not believe that it was me standing there I began to touch, and rub myself again not even thinking that she was behind me watching all the while I was doing this. She told me that she would not tell anyone about this as long as I was to include her in my dress up, and that she would have thing layed out for me when I come over her house to dress up again. I was so caught up in the moment I would have said anything to this women, I said Yes, Ok. She then reached around the front of the dress and grabbed the bulge that my cock was making and said that we have to get rid of that somehow. She brought me out and layed me down on the bed, she layed down next to me and said what is it that you do with your cock when you dress up, or put on womens clothes. I was a little shy at this point but told her that I usually jerk myself off at this point, she reached for my hand and placed it on my crotch and said that she would really like to watch me do that. I looked at her and she had a very hungry look about her at this point, almost trance like. i told her that I couldn’t, that she was my neighbor and my Moms friend. She looked into my eyes and said, If you don’t do this for me seeing that all I have let you do so far I’m going to tell your Mom about this and what do you think she is going to say and feel about all of this? I reached down without saying another word and began to pull the dress up so that I could get my cock out and begin to play with it when all of a sudden I felt her hands in my pants pulling it out for me and said her you go, I want to see you make yourself cum. I reached down and began to stroke my cock, I was so fucking hard at this point as I didn’t know what was turning me on more the clothes, or the fact that I was jerking off in front of a beautiful older women, or both. I was really getting into it and I could see the lust in her face all the while she was watching my hand sliding up, and down my cock when all of a sudden she kissed me on the mouth like I have never been kissed before, I thought I was going to loose it just then when all of a sudden she stood up and pulled her panties off from under her dress and climbed back on the bed and began to finger herself furiosly. I think that she was more turned on at this point that I was. After a few minutes she screamed out and said I can’t take it anymore and threw her leg over my head and straddled my face. She tasted so HOt, and Sweet at the same time. I thought at one point that she was going to either smother me, or break my jaw the way she was riding my face. After a few minutes she exploded on my face, I have never before experience a women that could squirt before, and i think I was at this point because I had cum running down my chin to my neck, and everything got real wet. She got off of my face at this point and grabbed my cock and swallowed me whole, I couldn’t believe that she was able to take the whole thing down her throat as I am 7 1/2 ins.
long. She gave me by far one of the best blowjob I had ever gotten at that point in my life. She sucked, licked, and continued going down on me and then she reached into her crotch and got her finger wet and stuck it in my ass, and was finger fucking me and whispering in my ear that there will be more, and bigger things in your ass as time goes by. Well I lost it at that point and filled her mouth full of cum she then came up to my face and kissed me again full on the lips, this time though her mouth was full of cum and she spit it in my mouth afterwards telling me that a Good Girl will always swallow her mans load. I didn’t know what to do with it so I swallowed it, and then she said welcome to womanhood. We talked afterwards me still dressed up in her clothes sitting on the bed and she told me that we would never have intercourse, just touching, and oral sex because to her that’s not cheating. Who was I to argue, I was able to dress up in all of her beautiful things, she even had a section of her closet, and lingerie draw for things that she purchased for me over time, and i was having sex with abeautiful older women who taught me more than how to dress as a woman, she also taught me how to please a women as well. My neighbor moved about 3 years after and the day she left she had put all of my things in a couple of suitcases for me and told me that if I was ever to come down to visit that i should bring my things. I never did see her after that, I really missed her, and to this day I always think about her and the things we did.
