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Title: My First Time
My first experience dressing in lingerie came at the age of 12. My Aunt Dolly lived with me my mom and my older sister. My sister was 17 and we shared a room together and I always had the opportunity from a very young age to watch her get dressed and undressed and had the pleasure of seeing my sister naked and in lingerie many times. Living with 3 women I had plenty of opportunity to look up their skirts and dresses and was always intrigued at what I saw. My mom, sister and aunt all wore stockings, garter belts or girdles and heels (it was late early 60's at the time} and as we all know stockings and garter belts were still very popular before pantyhose came along. One day I decided to make a visit to my aunt dolly's bedroom to look for her undergarments. I went through all her dresser drawers until I found what I was looking for. She had so many different pairs of stockings and satin and lace garter belts, panties, bras I couldn't make up my mind which to try on. I picked out a pair of black seamed RHT stockings and a white lace garter belt and started putting them on. My aunt was on the short side and her stockings fit me perfectly. I pranced around her room looking at myself in her full length mirror and was overjoyed at how I looked and how wonderful I felt. My cock was so hard from looking at myself I decided I would lay on my aunts bed and jerk off until I would shoot my cum. This became almost a daily ritual for me and went on for about 2 years without being discovered. One evening it was late and my aunt always stayed up later than my sister or mom, I had off from school the next day so I decided to stay up with her. We sat talking about this and that and before long my aunt fell asleep in her recliner. I sat across from her on the sofa admiring her and how pretty she was. Occasionally she would turn from side to side getting more comfortable in her chair and as she did her skirt would rise up her legs until it was almost around her waist. She turned over one more time and as she did she kind of slid down further in the chair and as she did her skirt moved up completely around her waist and to my delight I could see her stockings, garter belt and her pretty white lace panties. The panties were pulled tight against her pussy and I could see the perfect outline of her pussy. This was more than I could stand and without thinking I took my clothes off and sat on the sofa across form her completely naked and started to jerk off. All she had to do was wake up and she would be able to get an eyeful of her nephew stroking the biggest hard on I ever had. Sitting there looking at my aunt in all her glory I got an idea. I have always wanted to be caught by my aunt, my mom or my sister while wearing stockings, garter belt and heels and thought this might be a perfect time for it to happen. My aunts bedroom was on the first floor so I got up and went to her room, picked out my favorite pair of stockings, garter belt, bra and heels and no panties. As I started dressing my heart began pounding so hard I thought it would explode. I was going to dress for my aunt and I WANTED her to wake up and catch me and would stay dressed in front of her until she did. Once dressed I walked back into the living room to where my aunt was, stood in front of her chair and started stroking my hard cock. After a few minutes I lay down on the sofa with my legs spread very wide so that when she woke up she would be sure to get the perfect view of me. After about 20 minutes or so of playing with my cock and watching my aunt and getting so much pleasure looking at her beautiful legs and her pussy outlined in her panties I couldn't take it anymore. I had to cum and I wanted my aunt to see me cum. I wanted her to know that I was cumming because of her and FOR her. While keeping my focus on my aunt I started to jerk off faster and harder. I would look at her then look at my cock, then run my hand over my stockings and look back at my aunt. Wanting my aunt to wake up and catch me I started to moan loudly as my hand got faster on my cock. I was ready to cum and let out several loud moans. As I did my aunt woke up and there I was, on the sofa legs spread wide in her stockings, garter belt and heels jerking off for her. She focused on me and let out a loud gasp and as she did my cock exploded shooting my cum high in the air. Load after load shooting from my cock landing on my hand on my stockings the floor. I was covered in cum and never once took our eyes off each other. When I was finished I figured I was really in for it. I thought my aunt would run and tell my mom or scold me or something unpleasant like that but instead she sat up looked right at me and said, "did it feel good" I quickly responded that I felt wonderful. To this day I still wear lingerie, stockings, heels and have a large collection that would be the envy of any woman. My wife never understood my obsession or desire to dress as a woman and eventually the marriage came to an end
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