This is not a story of fantasy. This is a true story. I promise I have not embellished or stretched any of the truth, excluding names. These are the stories of Ashlyn and her path in to sissyhood. If this receives some attention and people want to hear more of Ashlyn's adventures into Sissyhood please email me at Ashlynb.xxx@gmail.com It all started when I was young, about 12. This is when I found myself wondering about my mothers and sisters clothes. I would steal a pair from time to time and jerk off into them. When I grew braver I would sneak into the back room and steal a tampon and examine it wondering what it felt like until one day I put it inside my pussy, I found that this was a great way to clean the inside of me. But I am going to go forward to one of my favorite memories and the first time I found that I could cum from penetration. I was 15 at the time. I had grown my hair out to just below my ears and swept across my face. I was a larger kid and being larger I had what could constitute as the beginnings of a chest. My hair was dark brown and my face was soft from the extra fat I could never drop and how I seemed to have an aversion to facial hair. I had deep blue eyes that I was always told were my best feature. I stood only at 5'7" with a normal body type, somewhat boxy but one I learned to control with proper attire. At this time in my life my parents had divorced and I lived with my mother and little sister. My older sister was out of the house but would stay with us from time to time. With this many women and a lack of a father it's no wonder I became a sissy. My mother worked late in the week and I was always home alone for at least two hours as I didn't have a final bell in high school and my little sister was in elementary school and got home later than me. This meant I had two hours most days to be Ashlyn. This story is about one of those particular days... The bus ride home that day was agonizing. All I wanted to do was get home and get into clothes that I felt more comfortable in. Finally I was home and ran straight upstairs to my room. Once in my room I stripped naked and skipped down to the bathroom. We had a full length mirror in the bathroom and I always took a moment to examine myself before I jumped into the shower. I stood die facing the mirror and lifted my little breasts trying to make them look bigger, all the while puffing out my lips. I stood on my toes trying to make my ass pop a little and sucked in as much as I could. I reached down and tucked my little cockette in between my legs. After standing there for a moment wishing my boobs and ass were bigger and my belly smaller I turned on the water and jumped in. At this time in my life I kept my legs shaved at all times. I was always one to wear pants and never much liked swimming. With the rest of my body having aversion to hair as my face I was always relatively smooth. I quickly touched up where a few hairs seemed to be growing like a bean stock and quickly washed my body. I had run out of body wash a week ago and purposely forgot to tell my mom so I had a reason to use hers that smelled of lavender and honey. I tried my best to keep my cockette tucked as I showered but it seemed to more I tried to stuff it back the more it sprang forward with more life. I jumped out of the shower and wrapped the towel high on my chest like I have seen my mother due so many times before and blow dried my hair. I parted it on my right side and swept my bangs left. I dried the rest of my body and walked into my sister's room down the hall across from my room. My older sister always kept a small cache of clothes in my little sister's closet. I snuck in; even though I was alone I was always afraid I was going to get caught. I found the bag she kept the clothes in and found a pair of black bikini cut panties and a black bra to match. Luckily my older was about my size and her under wear worked best for me. Unfortunately, she didn't have much in the way of clothes, just jeans and some shirts, and I was in the mood for a skirt. I snagged the underwear and went back into my room. I sat on the side of my bed and pulled the panties up and tucked my cockette the best I could, which wasn't very much at this time as it was yearning for attention. I struggled but snapped the bra around my chest but I was able to do it. I walked over to my dresser, feeling myself swaying my hips now as I became Ashlyn. I found two pairs of socks and stuffed them deep into the bra. I then reached in and pull up on what little breast I did have so they would sit on top. I was rather impressed with what I was able to create and I was really starting to feel more and more comfortable. I walked down to my mother's room to see what I could find to wear and was able to find a pleated black skirt that came down to my knees. I slipped into the skirt and rolled it a few times so it came about two inches up from my knees. I went over to my mother's vanity and applied some light blush, a hot pink lipstick, and a little mascara something knew I could take off quickly and effectively with a little vaseline. I walked back to my room and found a white button that my Aunt had gotten my a few months back and was about two sizes too big. I grabbed the bottom and tied it just below my new breasts. I walked over to the mirror on top of my dresser and admired myself. I loved what I saw. I saw a slutty short brown haired, blued eyed girl ready from fun. I walked over to my bed. My bed frame was one of the old ones that had a solid frame with drawers underneath. I pulled out the drawer closest to the head board and reached all the way to the back. This was a sight to see as I was on my knees with my ass high in the air and the skirt slowly riding up show just the bottom of my ass. Instinctively I wiggled it a little and thought about a boy standing there and staring. I reached back and grabbed a giant bubble wand, the kind that looks like a oversized dildo and is sold to children. I then grabbed the lotion I kept on my dresser for my "dry hands"... and crawled up on my bed. My bed was sitting in the corner of my room and was pushed up against the wall. When I crawled on my bed I turned over and scooted my but up to the wall. I placed my feet onto the wall and slowly lifted my hips and slid the panties up to my knees. I scooted and walked up the wall until I was able to throw my legs over my head. I was now lying on my bed with my feet dangling over my head and my cockette pointing at my face. I grabbed my bubbled wand and lotion. I squirted a big glob into my left hand and rubbed it all over the wand and then took what was left and slipped a finger into my pussy to get it ready. As my finger entered my tight hole I felt my cockette twitch and couldn't help a small moan escape my closed lips. With my other hand I lined up the wand to my tight puckered hole and applied a little pressure. I felt my hole begin to open up to gobble up my wand. A wave of pain and pleasure washed over me and I held the wand in place until the pain subsided. I pushed in a little farther and felt another wave flow over me. I knew that this was the last wave of pain as the girth of the wand was now inside me. I tiled the wand back and aimed at my cockette from inside my hole and slid it in father until I found the spongy haven of my g-spot. As soon as I felt pressure on it my cockette jumped and I squirmed with excitement. I began moving the wand in small circles and wave after wave flowed down my toes and back up to my head. I pushed harder and faster making each wave hit more like a shock. With each shock a small moan escaped my lips and my cockette jumped with excitement. I felt my cockette begin to fill and watched and a few drops of pre-cum dribbled out onto my chin and chest. Now filled with excitement, I couldn't resist and plunged the wand as deep as I could into my pussy and scream of pleasure exploded from my mouth and my cockette jumped with a fast dribbling splashing on my face. I began to pull then wand to the tip and plunging in deep into my ass, making sure that each time I came in and out I stroked my g-spot. My young horny self couldn't resist any more and my left hand flung to my cockette and began rubbing with a fury. I started to bounce on my bed as I plugged my wand deep into my pussy and stroked my cockette. I was moan and begging for more and was quickly rewarded as I spurted hot creamy streams of cum on my face. I naturally smiled and yelled out a proud "Fuck yes". I plunged the wand in as deep as I could and with both hands began scooping up as much cum as I could and swallowing each drop loving the flavor. When I was pleased that I had found ever morsel of cum and filled my sissy appetite I slowly removed the wand and walked down to the bathroom to clean myself. I went back to my room slipped back on the panties and fixed my hair. I walked over to my desk and sat to write in my journal. I penned about the most recent explosion of cum and the day dreams of boys at school. I wrote about how I stared at girls envious of their looks and wishing I could be like them. I checked the time and saw I only had a half an hour before my mother came home and knew it was time to change back. I sat there sad, satisfied, and complete wishing I didn't have to stop being Ashlyn. I slowly got up and cleaned my makeup off, placed back the clothes, hid the wand, and lay on my bed. A few moments later my sister came home from school and my mother not far behind her.
If you want to hear more of Ashlyn's path to Sissyhood please email me at Ashlynb.xxx@gmail.com The path leads to sex with friends, friends brothers, random encounters, and a few with a step sibling.