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, 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 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!!! 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. At that time he was about 34 or so and real nice looking, with short black hair and a goatee with blue eyes and a great body and a real ladies man. I had a little crush on him since he moved in and he secretly was a fantasy of mine sometimes when I was dressed up. And now here he was in the kitchen with me… Denny apologized for barging in without knocking and after a few minutes of talking I think we both got a little more comfortable with each other as we sat down at the kitchen table. Denny had a million questions like when did I start dressing like a girl, how often I dress and of course if I was bi or gay…and I looked him square in the eye and told him that when I was dressed like this that I wanted to be with a man so bad… Denny didn’t say a word. “Care for a drink? I asked in order the break the awkward silence. “Yeah, I think I need a drink right about now.” When I stood to get Denny the scotch he asked for I saw his eyes travel up and down my body. Denny gulped down the drink in one swallow and quickly poured himself another. After slamming down his drink Denny stood up and said. “Guess I better go now.” Realizing this was the moment, I stood and put my arms around his waist and hugged him and said “Please don’t go.” I looked up and he then kissed me! My head was spinning and my heart pounding as my lipstick smeared between us. My hand found its way to his crotch and I massaged the outline of his hard cock through his jeans and I heard him moan softly. After a few minutes we broke apart and looked in each others eyes. “Oh gawd, I cant believe we are doing this.” He said. “I want to taste you cock Denny.” I cooed. He smiled back at me and I knew then that it was going to finally happen. “Grab our drinks and I will meet you in the living room” I said as I headed to the bathroom. In the bathroom I wiped off my smeared lipstick and powdered my chin and applied another coat of the pretty red lipstick then went to the living room. Denny was sitting on the couch and I sat down next to him and reached over and unbuckled his belt and pulled the zipper down. He didn’t say a word as I removed his cock and held it in my hand and stroked it a few times. He closed his eyes and put his hand on my back and gently pulled me towards him and I parted my lips and slid them down his hard shaft ever so slowly. “Oh fuck that feels so great.” He hissed. I pulled at his pants and Denny lifted his ass as I pulled them all the way off and I positioned myself between his spread legs and resumed sucking his cock. Needless to say a real cock felt different than the dildo I practiced with but judging by his reaction he certainly was enjoying it! I got into a smooth rhythm of sucking his shaft while stroking it with my hands and it wasn’t long before he stiffened and started to cum in my mouth. It tasted musky and a little sour but I liked it and felt so proud of my accomplishment. “Damn baby that was some blowjob!” he said smiling down at me. “Thank you Denny, I really needed that.” I got up and sat down next to him and put my head on his shoulder, still playing with his still hard cock. I kissed his neck and he moaned again, then he kissed me, no doubt tasting his cum remnants of his cum in my mouth. His hands found their way to my tits and it felt nice even though they were silicone falsies. Coming up for air I excused myself and beaded to the bathroom where I fixed my lipstick once again and took off my skirt and grabbed a small bottle of baby oil and massaged it into my pussy-ass. When I returned Denny was stroking himself with one hand and his drink in the other. I took a big swig of my drink and positioned myself on my hands and knees with my ass facing him and looked back over my shoulder… “Fuck my ass Denny.” I said. Denny immediately got up and stood behind me and squatted over me, guiding his cock to my hole. He rubbed it around my tight fuck hole then pushed against the opening and I pushed back, sliding it right inside me. The slight pain I felt at first was overtaken by the nice feeling of his cock in me as he gently begain moving it in deeper. “Ohhh Denny fuck me” I squealed. “Shit baby it feels so tight.” “Fuck my pussy Denny, fuck it!” It felt so great having his cock inside me and I don’t know how long it lasted (but I was pretty sore the next day!) but I felt his cock twitch and he filled my ass with his cum. When he plopped out a warm stream of cum dripped down my crack and onto my hanging balls. My little clitty cock was hard as a rock and I need to cum too so I turned over on my back and masturbated using Dennys cum as lubrication. Denny watched me and it I didn’t take long at all and I spurted several times all over my clitty and hands. Denny left right after that, but not before I said I would be dressing up again tomorrow if he was interested…..
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com
with this note attached, it has been posted without my permission.
<a href="https://www.lushstories.com/stories/crossdressing/the-very-first-timewith-lots-more.aspx">The very first time....with lots more to come...</a>