Date: Mon, 22 Mar 2004 17:53:21 -0800 (PST) From: Dan R Subject: My first time crossdressing part 1 My first time crossdressing By Danielle Reilly THIS IS A COMPLETELY TRUE STORY OF MY FIRST TIME CROSSDRESSING A quick background Growing up I'd always been fascinated by women's clothing. Seeing a girls smooth legs peeking out from under a skirt, accentuated by her high heels was just a huge turn on for me. Since then I've always loved women's lower bodies. The skirts, panties, hose, and high heels that they wear are my favorite things in life. When I was 11 I began to investigate some of my mothers clothing, rifling through her silky panties, bras and pantyhose I experienced my first erection, though at the time I didn't really know what it was. After a few months of just exploring her underthings, I began to try them on while the family was away. Because I went to a private school, I got out of school at 2:30 in the afternoon and my mother worked at the public high school she wasn't home with my younger sister until 4, and my father wasn't home until 6, so I had plenty of time to explore my feminine side. When I was 13 I experienced my first orgasm, while washing myself in the shower. After that, I just couldn't get enough, and masturbated at least 4 times a week. It was also around this time I began trying on some of my mother's panties and hose, and luckily for me my mother and I were the same size at this point in our lives. After I turned 14 my parents told me that they were going on vacation to Florida in the summer, and asked if I wanted to go with them. Of course seeing the opportunity to spend 10 days home alone I said no. The First Day Finally June came around, and the day of their departure came after several sleepless nights of excitement. After watching my parents drive down our driveway (which was a long one in full view of the house), and waiting long enough to be sure they wouldn't be coming back to get something they forgot, I ran across the house towards my parents bedroom, and more importantly my mothers closet, stripping off my clothing as I went. For a while I had been planning for this week alone, and knew exactly what I wanted to do. I'd even let my hair grow for the past 3 months so that I would have semi long hair at the time. Heading into her bedroom I quickly raided the closet. I pulled out her purple minidress. I'd only seen her wear it once at a party, but I loved it. It was purple velvet (or something like it), with low cut shoulders and front. It was a tight dress and hugged curves, and ended at mid-thigh. I also pulled out from the bottom or her closet her pair of 4" black stiletto heels. Moving over to her dresser, I quickly selected a black wonderbra, tight black lace panties, and a pair of black thigh high stockings. I quickly hopped in the shower and washed my hair and body quickly. Being only 14 I didn't have much body hair, but I went over my body quickly with my moms razor until I was completely hairless. Hopping out of shower I wrapped my towel around my chest like I had seen my mom do a hundred times. I spent extra time in the mirror making sure my face was completely hairless. Staying at the mirror, I opened my mom's makeup case and began to experiment. I brushed a small amount of mascara to my eyes, followed by some blue eyeshadow and a small amount of blush to my cheeks. Finially I applied some bright red lipstick to my lips. Looking in the mirror I was surprised to see the face a slightly older girl looking back at me. I puckered my lips, and then moved back to the bed in my mom's room where my clothing was waiting. I quickly pulled the lacy bra out of the pile and wrapped it around my chest. Clipping it in the front, I rotated it around and slipped my arms through the straps. After adjusting the length of the straps slightly (my mother and I were about the same size after all), I filled the cups with some flesh colored nylons from the dresser. Grabbing the panties from the bed, I slinked them up my hairless legs, relishing the feeling of the lacy material and it caressed my skin. Sitting back on the bed, I balled up the nylons and slinked them up my legs, snapping them tight around my thighs. Slipping my feet into the high heels I stood and quickly wobbled back down on the bed. Slowly I stood back up and took several laps of the house, getting used to walking in the heels. After about 10 minutes I felt comfortable enough in the heels, but I was experiencing another problem. The feel of the lacy panties was driving my cock nuts, and my raging erection was poking out the top of the panties. Headed to the bathroom, I loved the way that my legs and butt felt in the high heels. The feeling of the lace panties and hose on my skin, and the way my legs looked in the heels was turning me on more than I'd ever been. In the bathroom I quickly pulled my panties to the side allowing my cock to spring free. The head of my uncircumcised penis was dripping precum like it was water, and I noticed it had actually made a small stain on the front of the panties. Grabbing a quick handful of toilet paper and teetering on my heels, I quickly began to stroke my aching prick. After only a few strokes I felt my orgasm building, and I felt my knees buckle as it hit. Falling to my knees I watched my hot cum spurt right through the handful of tissues and into the palm of my hand. Regaining my composure, I dumped the tissue paper into the toilet and quickly washed my hand, though the hot cum on my hand had intrigued me. I tucked my now flaccid penis back between my legs and was pleased to see the flat front on the panties. Back in the bedroom, I quickly slipped into the dress and zipped the back. Looking in the full- length mirror on the wall, I saw a sexy young girl looking back and me and was pleased with the way I looked. I took the next 20 or 30 minutes to look through my mother closet for things I may have missed earlier, and found a blouse and skirt I wanted to try on later, as well as some silk camisoles that I would try on too. Under one of the camisoles in the drawer, I also found a tube of KY. Deciding that I would spend the next 9 or 10 days as a girl, I poured myself a glass of juice and, still practicing walking in the heels, went to the living room. Logging onto the Internet, I quickly checked my email, nothing new, and then began surfing the web looking for sites about dressing as a girl. After looking quickly at some websites of some beautiful t-girls, I stumbled into the nifty transgendered stories archives. I spent the next 5 to 6 hours reading stories about other people dressing as girls, living as girls, and what really peeked my interest were the stores of the people having sex as a girl. Downloading several of my favorites to the computer, I logged off the net. By this point I was extremely horny again, but I was determined to experiment more. After rereading a couple of the stories that contained detailed descriptions of their sexual experiences, I wanted to try some of them for myself. Making my way around the house, I quickly locked the doors and closed all the blinds, ensuring that some unsuspecting person would not catch me. Wanting to feel more feminine than I already felt, I decided that I wanted to experience sex in the female sense. Considering what I had read in the stories, I decided that anal sex was something that I wanted to try. Knowing that it would be difficult the first time, I ran back to my mother's bedroom and grabbed the tube of KY from her dresser. I decided that my bedroom would be the best place for me to try it, just because I felt more comfortable there. Feeling very horny and wanting to have the best experience possible, I decided to stay dressed as much as possible. Slipping my panties down my legs, I kicked them off and they landed on the bed. I began to root through my desk drawers looking for something to use, and in the back of one of the drawers I found a .50 caliber bullet that I had bought several years earlier. It was roughly the same size and shape and my penis, and it seemed like the perfect substitute. I dropped a towel onto my bed to keep from making a mess on my comforter, and stood next to the bed. I Spread my legs wide and hiked the dress up and over my hips like I'd seen so many girls in pictures do, and bent forward over the bed. I could feel my ass check pull apart and the cool air of my house caress my rosebud. I was glad I'd chosen to shave my butt and clean my ass thoroughly inside and out while I was in the shower. Spreading a generous amount of the KY onto my fingers, I felt a chill run up my back as I spread the cold gel onto my hole. Applying more gel to my hand, I bit my lip as I pushed my middle finger into my ass. It slipped in surprisingly easier than I thought, and didn't hurt at all. Sliding my middle finger in and out I applied even more KY to my fingers, lubricating my ass thoroughly inside and out. Soon my hole felt loose enough that my finger was easily moving, and I slipped in a second, and as it loosened even more a third. As I moved my fingers in and out I relished in the feelings I was having, and wanted something bigger. As I removed my fingers my ass felt empty, and I just had to have something in it. I spread more KY onto the cold bullet and placed the tip against my hole. The cold sent another shiver up my back but I needed it. Pushing in I felt my sphincter stretch to accommodate it, and I loved it. Quickly I felt the tip of it slide against my prostate, and I thought my dick was going to explode. It pulsated and I could feel cum moving upwards in my hard shaft. My right arm, holding me up on the bed, almost collapsed as the feeling washed over me. Unsure of what just happened, but knowing it was good, I slowly retracted the bullet and pushed it back in, again hitting my prostate and sending the feeling through me. Starting slowly I began to fuck myself with my artificial cock. Moving it faster and Faster, I could feel the beginnings of my orgasm and I had yet to touch my hard cock. I moaned out loud as I fucked my ass, rocking back and forth on my high heels in rhythm with my fucking. Looking down onto the bed I say my panties bunched up on the bed, and I picked them up, replacing my hand with my elbow and bringing them to my nose. I could smell my precum on them and noticed a wet spot on the front where my cock had rested, and extending my tongue I tasted it. It tasted very good and I knew I wanted more, but at the time I was too busy fucking myself to do anything about it. All too soon I felt my orgasm coming, and with a loud moan I felt my cock swell and explode my hot sticky cum onto the towel. My sphincter tightened around the bullet and my entire body pulsed as my orgasm washed over me. I lost track of time briefly and I don't know I long I stood there, bent over the bed with my ass in the air like a slut, cum dripping from my now flaccid cock, but after what seemed like forever I felt the bullet slip out of my well-fucked ass and fall to the floor. Still bent over the bed, I picked up the towel and wiped the dripping cum from my prick, then wiped the KY from my ass. Straightening up I slipping my nylon-clad legs back into the panties and pulled them up around my waste, and wiggling my hips settled the dress back into place. After sitting on the bed for several minutes recovering, I went to the kitchen and quickly made myself a small bowl of soup (I hadn't eaten all day and needed to keep my strength up). Settling on the couch, I crossed my legs and slowly ate my soup, watching Ally McBeal or some other very feminine show (I can't remember now what it was). After the show I decided it was time for bed, as it was about 11 at night and I had a lot more plans for the week. Heading back into the bathroom, I washed off my makeup and headed into my mother's room again. Slipping off the dress, I laid it out on the bed neatly, and then opened the drawer in her dresser containing her nighties. I selected quickly a white silk camisole with pink flowers and matching panties. I slipped my feet out of the heels, and slipped the stockings off my legs. After unclipping the bra I slid the panties down my legs, and picked up the white bikini cut silk panties. Sliding them up my legs, I squirted some aloe into my hand from a bedside pump and quickly applied it to my smooth legs, keeping them soft and smooth. I slipped the camisole over my head and felt it slip down until it rested lightly on my shoulders. I walked back across the house to my bedroom, swaying my hips and loving the feeling of the silk. I slipped under the covers and closed my eyes, thinking about all the fun I had just had, and all the fun I was still going to have. And that was just the first day... END OF PART 1, MORE TO COME I'd love some feedback, send emails to Vtcarfanatic@yahoo.comMy first time crossdressing By Danielle Reilly THIS IS A COMPLETELY TRUE STORY OF MY FIRST TIME CROSSDRESSING A quick background Growing up I'd always been fascinated by women's clothing. Seeing a girls smooth legs peeking out from under a skirt, accentuated by her high heels was just a huge turn on for me. Since then I've always loved women's lower bodies. The skirts, panties, hose, and high heels that they wear are my favorite things in life. When I was 11 I began to investigate some of my mothers clothing, rifling through her silky panties, bras and pantyhose I experienced my first erection, though at the time I didn't really know what it was. After a few months of just exploring her underthings, I began to try them on while the family was away. Because I went to a private school, I got out of school at 2:30 in the afternoon and my mother worked at the public high school she wasn't home with my younger sister until 4, and my father wasn't home until 6, so I had plenty of time to explore my feminine side. When I was 13 I experienced my first orgasm, while washing myself in the shower. After that, I just couldn't get enough, and masturbated at least 4 times a week. It was also around this time I began trying on some of my mother's panties and hose, and luckily for me my mother and I were the same size at this point in our lives. After I turned 14 my parents told me that they were going on vacation to Florida in the summer, and asked if I wanted to go with them. Of course seeing the opportunity to spend 10 days home alone I said no. The First Day Finally June came around, and the day of their departure came after several sleepless nights of excitement. After watching my parents drive down our driveway (which was a long one in full view of the house), and waiting long enough to be sure they wouldn't be coming back to get something they forgot, I ran across the house towards my parents bedroom, and more importantly my mothers closet, stripping off my clothing as I went. For a while I had been planning for this week alone, and knew exactly what I wanted to do. I'd even let my hair grow for the past 3 months so that I would have semi long hair at the time. Heading into her bedroom I quickly raided the closet. I pulled out her purple minidress. I'd only seen her wear it once at a party, but I loved it. It was purple velvet (or something like it), with low cut shoulders and front. It was a tight dress and hugged curves, and ended at mid-thigh. I also pulled out from the bottom or her closet her pair of 4" black stiletto heels. Moving over to her dresser, I quickly selected a black wonderbra, tight black lace panties, and a pair of black thigh high stockings. I quickly hopped in the shower and washed my hair and body quickly. Being only 14 I didn't have much body hair, but I went over my body quickly with my moms razor until I was completely hairless. Hopping out of shower I wrapped my towel around my chest like I had seen my mom do a hundred times. I spent extra time in the mirror making sure my face was completely hairless. Staying at the mirror, I opened my mom's makeup case and began to experiment. I brushed a small amount of mascara to my eyes, followed by some blue eyeshadow and a small amount of blush to my cheeks. Finially I applied some bright red lipstick to my lips. Looking in the mirror I was surprised to see the face a slightly older girl looking back at me. I puckered my lips, and then moved back to the bed in my mom's room where my clothing was waiting. I quickly pulled the lacy bra out of the pile and wrapped it around my chest. Clipping it in the front, I rotated it around and slipped my arms through the straps. After adjusting the length of the straps slightly (my mother and I were about the same size after all), I filled the cups with some flesh colored nylons from the dresser. Grabbing the panties from the bed, I slinked them up my hairless legs, relishing the feeling of the lacy material and it caressed my skin. Sitting back on the bed, I balled up the nylons and slinked them up my legs, snapping them tight around my thighs. Slipping my feet into the high heels I stood and quickly wobbled back down on the bed. Slowly I stood back up and took several laps of the house, getting used to walking in the heels. After about 10 minutes I felt comfortable enough in the heels, but I was experiencing another problem. The feel of the lacy panties was driving my cock nuts, and my raging erection was poking out the top of the panties. Headed to the bathroom, I loved the way that my legs and butt felt in the high heels. The feeling of the lace panties and hose on my skin, and the way my legs looked in the heels was turning me on more than I'd ever been. In the bathroom I quickly pulled my panties to the side allowing my cock to spring free. The head of my uncircumcised penis was dripping precum like it was water, and I noticed it had actually made a small stain on the front of the panties. Grabbing a quick handful of toilet paper and teetering on my heels, I quickly began to stroke my aching prick. After only a few strokes I felt my orgasm building, and I felt my knees buckle as it hit. Falling to my knees I watched my hot cum spurt right through the handful of tissues and into the palm of my hand. Regaining my composure, I dumped the tissue paper into the toilet and quickly washed my hand, though the hot cum on my hand had intrigued me. I tucked my now flaccid penis back between my legs and was pleased to see the flat front on the panties. Back in the bedroom, I quickly slipped into the dress and zipped the back. Looking in the full- length mirror on the wall, I saw a sexy young girl looking back and me and was pleased with the way I looked. I took the next 20 or 30 minutes to look through my mother closet for things I may have missed earlier, and found a blouse and skirt I wanted to try on later, as well as some silk camisoles that I would try on too. Under one of the camisoles in the drawer, I also found a tube of KY. Deciding that I would spend the next 9 or 10 days as a girl, I poured myself a glass of juice and, still practicing walking in the heels, went to the living room. Logging onto the Internet, I quickly checked my email, nothing new, and then began surfing the web looking for sites about dressing as a girl. After looking quickly at some websites of some beautiful t-girls, I stumbled into the nifty transgendered stories archives. I spent the next 5 to 6 hours reading stories about other people dressing as girls, living as girls, and what really peeked my interest were the stores of the people having sex as a girl. Downloading several of my favorites to the computer, I logged off the net. By this point I was extremely horny again, but I was determined to experiment more. After rereading a couple of the stories that contained detailed descriptions of their sexual experiences, I wanted to try some of them for myself. Making my way around the house, I quickly locked the doors and closed all the blinds, ensuring that some unsuspecting person would not catch me. Wanting to feel more feminine than I already felt, I decided that I wanted to experience sex in the female sense. Considering what I had read in the stories, I decided that anal sex was something that I wanted to try. Knowing that it would be difficult the first time, I ran back to my mother's bedroom and grabbed the tube of KY from her dresser. I decided that my bedroom would be the best place for me to try it, just because I felt more comfortable there. Feeling very horny and wanting to have the best experience possible, I decided to stay dressed as much as possible. Slipping my panties down my legs, I kicked them off and they landed on the bed. I began to root through my desk drawers looking for something to use, and in the back of one of the drawers I found a .50 caliber bullet that I had bought several years earlier. It was roughly the same size and shape and my penis, and it seemed like the perfect substitute. I dropped a towel onto my bed to keep from making a mess on my comforter, and stood next to the bed. I Spread my legs wide and hiked the dress up and over my hips like I'd seen so many girls in pictures do, and bent forward over the bed. I could feel my ass check pull apart and the cool air of my house caress my rosebud. I was glad I'd chosen to shave my butt and clean my ass thoroughly inside and out while I was in the shower. Spreading a generous amount of the KY onto my fingers, I felt a chill run up my back as I spread the cold gel onto my hole. Applying more gel to my hand, I bit my lip as I pushed my middle finger into my ass. It slipped in surprisingly easier than I thought, and didn't hurt at all. Sliding my middle finger in and out I applied even more KY to my fingers, lubricating my ass thoroughly inside and out. Soon my hole felt loose enough that my finger was easily moving, and I slipped in a second, and as it loosened even more a third. As I moved my fingers in and out I relished in the feelings I was having, and wanted something bigger. As I removed my fingers my ass felt empty, and I just had to have something in it. I spread more KY onto the cold bullet and placed the tip against my hole. The cold sent another shiver up my back but I needed it. Pushing in I felt my sphincter stretch to accommodate it, and I loved it. Quickly I felt the tip of it slide against my prostate, and I thought my dick was going to explode. It pulsated and I could feel cum moving upwards in my hard shaft. My right arm, holding me up on the bed, almost collapsed as the feeling washed over me. Unsure of what just happened, but knowing it was good, I slowly retracted the bullet and pushed it back in, again hitting my prostate and sending the feeling through me. Starting slowly I began to fuck myself with my artificial cock. Moving it faster and Faster, I could feel the beginnings of my orgasm and I had yet to touch my hard cock. I moaned out loud as I fucked my ass, rocking back and forth on my high heels in rhythm with my fucking. Looking down onto the bed I say my panties bunched up on the bed, and I picked them up, replacing my hand with my elbow and bringing them to my nose. I could smell my precum on them and noticed a wet spot on the front where my cock had rested, and extending my tongue I tasted it. It tasted very good and I knew I wanted more, but at the time I was too busy fucking myself to do anything about it. All too soon I felt my orgasm coming, and with a loud moan I felt my cock swell and explode my hot sticky cum onto the towel. My sphincter tightened around the bullet and my entire body pulsed as my orgasm washed over me. I lost track of time briefly and I don't know I long I stood there, bent over the bed with my ass in the air like a slut, cum dripping from my now flaccid cock, but after what seemed like forever I felt the bullet slip out of my well-fucked ass and fall to the floor. Still bent over the bed, I picked up the towel and wiped the dripping cum from my prick, then wiped the KY from my ass. Straightening up I slipping my nylon-clad legs back into the panties and pulled them up around my waste, and wiggling my hips settled the dress back into place. After sitting on the bed for several minutes recovering, I went to the kitchen and quickly made myself a small bowl of soup (I hadn't eaten all day and needed to keep my strength up). Settling on the couch, I crossed my legs and slowly ate my soup, watching Ally McBeal or some other very feminine show (I can't remember now what it was). After the show I decided it was time for bed, as it was about 11 at night and I had a lot more plans for the week. Heading back into the bathroom, I washed off my makeup and headed into my mother's room again. Slipping off the dress, I laid it out on the bed neatly, and then opened the drawer in her dresser containing her nighties. I selected quickly a white silk camisole with pink flowers and matching panties. I slipped my feet out of the heels, and slipped the stockings off my legs. After unclipping the bra I slid the panties down my legs, and picked up the white bikini cut silk panties. Sliding them up my legs, I squirted some aloe into my hand from a bedside pump and quickly applied it to my smooth legs, keeping them soft and smooth. I slipped the camisole over my head and felt it slip down until it rested lightly on my shoulders. I walked back across the house to my bedroom, swaying my hips and loving the feeling of the silk. I slipped under the covers and closed my eyes, thinking about all the fun I had just had, and all the fun I was still going to have. And that was just the first day... END OF PART 1, MORE TO COME I'd love some feedback, send emails to Vtcarfanatic@yahoo.com