The very first time….with lots more to come…


I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident.   I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt all tingly and excited like never before and after that I dressed up as often as I could. My single mom worked and dated and I had a lot of time alone growing up so by the time I was 17 I had collected a nice wardrobe of sexy clothes and all kinds of make-up and I looked pretty hot when all dolled up. I was shy so I confined myself to staying in and flirting with guys on the internet on my webcam although I fantasized all the time about being with a guy and couldn’t wait for to taste and feel my first cock.   It was the summer of ’97 when Mom and her boyfriend told me they were going away for a long weekend and I would be home all alone from a Thursday ‘till Sunday, and I couldn’t wait to spend the entire time dressed up! I bought a few things on line like a new skirt, two pair of sexy high heels, stockings, bahis şirketleri false eyelashes and a few sexy red lipsticks, and was so excited to try them all.   Mom and Don said goodbye and told me that if I needed anything to ask our neighbor, Denny and left around 3:00 on Thursday. I bet they weren’t even out of the driveway and I already had on my red lace bra and matching panties and was laying out my outfit I was going to wear on my bed!   I made a vodka and 7up and sipped it as I took my good old time putting on my make-up, searching for perfection.   After applying my foundation I did my eyebrows in a nice arch with a brown pencil and put on a smoky blue eyeshadow with a darker blue in the crease of my eyelid then I lined my eyes with a soft black pencil. The long false lashes went on without a hitch and after several coats of mascara I remember looking in the mirror and thinking how great my eyes looked, so sultry and sexy….I finished my drink and made another already feeling a nice warm buzz and headed hack   to the bathroom to complete my make-up. I bought an expensive Dior lipstick in a pretty red shade and couldn’t wait to see how it looked on me. I lined bahis firmaları my full lips with a red pencil and filled it in with the lipstick and loved it. It was so damn sexy!   I also bought a new wig that was light brown with blonde highlights and it was long and wavy, cascading off my shoulders and I loved it immediately. I teased it up real nice and at that point I felt completely transformed from Robby to slutty Lisa.   The new skirt I bought was a black stretch miniskirt that fit real nice and tight and my blouse was white cotton with a high starched collar that allowed my red bra to peek out just a bit. I also wore a wide red belt with a large god buckle and black thigh high stockings that looked great with my new red platform 5” high heels with an ankle strap. I wore gold dangly earrings and a gold choker necklace and a gold bracelets that matched. Looking back at me in the mirror that day was one hot and sexy gurl!   I grabbed a red nail polish and my drink and headed to the kitchen table to paint my fingernails that I had been letting grow long for the occasion. I freshened up my drink and started to apply the polish when I heard the back door opening!!! kaçak bahis siteleri I thought it was my mom returning for something and I freaked out, looking for a place to run but before I could move, in walked Denny the neighbor next door!   Denny just stared at me with a shocked look on his face as I am sure I did too!   “I’m so sorry, I was just checking on Robby, he finally said. I felt like my world was crashing down on me. I wanted to run and I was on the verge of tears but couldn’t say a word. “Is Robby here? He asked.   “Please don’t tell my mom.” I blurted out. “Holy shit Robby is that you?” He said in disbelief.   I didn’t reply but felt embarrassed and ashamed and looked away from him.   “Oh my gawd Robby you look amazing!” He said and he came over to me. “Let me have a good look at you.” He said as he gently took my arm and turned me around. Denny lifted my chin up with his hand and looked into my eyes. “Robby, you are one hot looking babe!” “You won’t tell mom will you.” I said on the verge of tears   “Of course I wont don’t worry about that.” He said with a big smile on his face. “I always thought you were a good looking kid but I…um, I never, um wow, you are one sexy girl.”   “Really, am I? “Oh my gawd honey, yes!” “I am happy to hear that.” I said.   Denny has been living next door for about two years and he is divorced.

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