08-10-2016, 01:18 PM
First of all a quick nod to Princess Tiffany her writing and detailed stories inspired me to try to write my own and as mine are not all about cross dressing they are me and how I came to be here. Thank you
So As a child my aunt was the first experience I really had with feminine culture was my aunt. She was so sweet and frilly. The grace with which she did everything enamored me. My mom was a tomboy and my only parent. My Aunt was frilly sweet, and kind. It was just a joy to be around her. I got to skip a grade at school because they thought I was a smart one. I was abused and then placed into custody with a foster family. They had me tested and I skipped another grade. I ran away and lived in an attic of an abandoned building for a few months. The police found me and then put me into the custody of my aging grandmother. She taught me manners and how to be proper and then passed away . I then fell into custody of the state who let me sleep at the station for a few months so I could turn 15 and get emancipated. I graduated from high school. I got a job cleaning up the local bar in the mornings which was no different than cleaning the drunk tank for the cops which was one of my chores when I was there. Also I got my own apt. and still 15.
Met a girl and her parents hated me because of my past. I was labeled the boy who got dropped off at school by the cops so I must be bad. Everyone in town was scared of me. It was and is a small town pop 5,000. I got different jobs as a sandwich maker, oil remover from drive troughs, VCR Repair man (yeah I’m that old), repo man of late movie rentals, and lawn mower. Got married when I was 16 I think I just really yearned for that perfect family life, stayed together for about 10 years went through many more jobs and some military. She was bi-polar and our daughter was beautiful. One day she decided to move to another country and kicked me out. I asked why she said I was too perfect and she didn’t measure up next to me so she wanted to leave cause she was tired of feeling lesser. She took my daughter away and went to Canada and that was that.
I then met a girl friend from Minnesota who I encountered one day while she was being attacked by a man bearing a large chef’s knife in a parking lot. I disarmed him and he scampered away. (Turns out he was her ex-husband who had stolen her son and fled back to Oklahoma) I was on the rebound and she was happy to be saved so I got a hero’s thank you and she went back to Minnesota in fear of her life not from me but her ex-husband.
I was alone and depressed I quit my job and they gave me full severance pay with overtime for a year. I was like 26 and ready to party. Katy was the name of my blow up doll and I dressed her up every day and she and I went out on the town everywhere together. Oh I know people laughed and scoffed but she was a real conversation starter. This was also my foray into actually picking out dresses. I loved shopping for clothes for her skimpy this skimpy that. My figure would not even come close to wearing that but anything and everything fit her. I attracted girlfriends by doing this too (not the dating kind the friend zone kind) and pretty soon I led a house with 11 female roommates and Katy. They loved giving me a make over as well and it was fun, and I felt pretty no clothes were involved just the make-up and nails. I practiced doing Katie's nails from then on as well. Her make up was painted on and I didn't think she needed any. Then one day Katy suffered a burn on her leg from a motorcycle and was unrecoverable. We had a funeral in the back yard and I insisted on burying her wardrobe with her. It felt like I just lost the fun side of me….. The severance check stopped but the parties did not they had evolved to be self-sustaining but the rent wasn’t getting paid. I told my roomies as well. I thought they would stop free loading and start chipping in and help pay the rent.But, instead they wanted me to strip for them I said "um what you want me to get paid to take clothes off". Yes they did for a preachers wife’s birthday party in a room in the back of the church.Without even thinking I said yes….
I arrived to strip and the room was full of women I was in the best shape of my life no I did not have a 6 pack but in a town with a pop of 5000 I guess I was hot and in demand. They treated me like meat and I liked it. It was great fun and the pay was excellent as in I made this month’s rent… but then the door opened and a lady said her husband was coming so I was led off by a lady who asked me to follow her through the maze of doors in this place. She led me to a heated spa and wanted to get frisky with me. She was hot and my age so I got in she slowly undressed and instructed me on all the things she wanted me to say to her. As she undressed I saw a corset and garter belt for the first time wow that was sexy! So I replied all whilst listening to a sermon about god in the background. It was erotic to say none the least but then before we got anywhere really the curtain was pulled back and there was the preacher. Worse this was not a Hot Tub it was a baptismal and they were in session. I thought well now I have done it nothing could get worse. Then it did as she said the one thing that could make it worse. She stared at the priest as he turned beet red and time almost stopped but before it did she said “Dad?” My soul left my body as I magically exited the baptismal and ran with no clothes on. I just ran. The dear reverend and some men from the congregation took chase. I searched the doors in this never ending maze till they were almost on me and then finally a way out. The grass on my feet and me flying free in broad daylight. As I ran down the road I felt alive, with an angry mob behind me of course. The convenience store in front of me just one stoplight intersection away. Of course there was a cop car right there at the intersection complete with officer inside when I ran by. The pavement was sooo hot and then the transaction to the cood floor of the store was soothing as I made my way to the beer. My plan was to push the cases back crawl into the cooler exit the cooler and flee out the back of the store losing the mob. It all went perfectly except my feet got stuck to the cooler floor a lot and it was really cold. I was not sure if I would look so manly streaking my way home LOL. I opened the back door of the store to come face to face with another cop. She said that there was no mob they arrested the rev at the intersection for attacking a police officer and had to take me in. However I was escorted to some of my old clothes that I had left there and told not to do it again. I was required to tell the story over and over for all my friends at the station. After all at one time I was there child. The Reverend did not get such treatment.
The next month came and more rent due. Well I did not want to be a stripper no more so I denied all such requests and then I received a request for a get together with no crowd just a one on one she wanted me to be her Gigolo so I thought why not the rent does have to get paid. So I went and serviced. Having watched the Hollywood movies I did demand to be paid up front and she did. I think she arranged it so that her husband would come home just after the deed was done more or less just magically showed up cause he barged in as soon as we were done and I never heard him pull up. It was so quiet in that neighborhood minus the screams he gave me about killing me and such blah, blah, blah I thought. After all he was no mob and I had already out run that so I grabbed the money and jumped out the window and ran streaking yet once again. The town newspaper put me on the Head line for the first time I wondered which page I would make this time. Then I heard the loud roar of his pick up and it was loud. He came tearing down the road trying to run me over in this monster truck. I dived out of the way but he did clip my heel and I spun in the air like a helicopter and landed in some bushes. I got up and ran all be it with a limp now but this time I cut through yards so that he would have to go around the blocks. I remembered a girlfriend’s house who lived in a house behind a house where I would stop and hide it was three blocks away so I had to make it. So I tried to push the pain out of my mind and run with tears streaking down my face. The first road came up and I could hear that damn truck roar as my feet met with the unforgiving blacktop the tires screeched around a corner I knew I could make it cause I was in the middle of the block so I ran. I hopped a fence and the pain came searing back when I landed. A dog showed up to give me encouragement to move faster. I hoped another fence and ran into goat heads and thought, no this will not deter me I will press on no matter what. So I quickly brushed off the stickers whilst in stride. The next road came up and he was all ready there parked and out of his truck with a bar. I decided to try to run around him as he swung at me and I ducked he hit the tail light on his own truck (yeah it was that tall) but I could not get up fast enough to dodge his foot as he literally gave me a swift kick in the ass like deep in the ass. Please remember I was naked at the time. This lifted me up enough to land on my feet running. He chose to not pursue but to get back into his truck and give chase. This gave me plenty of time to cross the next road before he even got there. From there I went straight to my friend’s house and knocked and knocked and knocked and an eternity later she answered the door. I was standing there naked and she answered with just a towel on. (LOL Writing this down it sounds like a porn intro) Frisky was far from my mind especially with the roar of the truck getting louder and louder. I kind of barged in while she asked me what was going on. She lived in a Loft so I could see she had company. I asked her to shut the door and then I told her everything. She laughed at me. Seems being a Gigolo is not for me either but the rent was paid. She had no men’s clothes for me only women’s she said. The thought enticed me to say the least and I told her I didn't mind borrowing some of those. So here is the moment I first dressed as a woman. She was a sexy seductress that was several sizes smaller than me so everything was super tight. The lady in the back of the loft giggled at me as she was wearing army fatigues and staring at me I thought well you got to do what you got to do. It seems I interrupted some frisky time between the girls and they were in earnest for me to exit, but I asked if I could just stay by the door till the sounds of the roaring truck dissipated. The clothing at the time did not come across as sexy or beautiful at the time just tight and restrictive. I did not feel good at all. The roaring stopped minutes passed it was time for me to leave. The lady in fatigues told me I looked good and hot as my farewell. All of a sudden I felt sexy, and I knew it but I had to go and I did. As I walked down the road in my spaghetti strapped top, miniskirt which showed my panties beneath, and flip flops which my heels hanged over the back of. I felt proud, heck I earned the rent I had made a new friend and I had clothes for the trip home. No cops, angry husband, or mob could bring me down. A guy mowing his yard stopped to look at me and whistle I smiled back. It was 20 to 30 blocks back home and aside from my huge head nothing else happened on the way home.
That is where I will stop for now. However for a teaser that lady in fatigues that thought I was hot, became, and is my wife of um 15+ years and that was our real first meeting with me in ladies clothes. Soo many things have happened good times, bad times, but cross dressing is fun awesome and not anything to be embarrassed about, I just want to look good before I tell people LOL.
So As a child my aunt was the first experience I really had with feminine culture was my aunt. She was so sweet and frilly. The grace with which she did everything enamored me. My mom was a tomboy and my only parent. My Aunt was frilly sweet, and kind. It was just a joy to be around her. I got to skip a grade at school because they thought I was a smart one. I was abused and then placed into custody with a foster family. They had me tested and I skipped another grade. I ran away and lived in an attic of an abandoned building for a few months. The police found me and then put me into the custody of my aging grandmother. She taught me manners and how to be proper and then passed away . I then fell into custody of the state who let me sleep at the station for a few months so I could turn 15 and get emancipated. I graduated from high school. I got a job cleaning up the local bar in the mornings which was no different than cleaning the drunk tank for the cops which was one of my chores when I was there. Also I got my own apt. and still 15.
Met a girl and her parents hated me because of my past. I was labeled the boy who got dropped off at school by the cops so I must be bad. Everyone in town was scared of me. It was and is a small town pop 5,000. I got different jobs as a sandwich maker, oil remover from drive troughs, VCR Repair man (yeah I’m that old), repo man of late movie rentals, and lawn mower. Got married when I was 16 I think I just really yearned for that perfect family life, stayed together for about 10 years went through many more jobs and some military. She was bi-polar and our daughter was beautiful. One day she decided to move to another country and kicked me out. I asked why she said I was too perfect and she didn’t measure up next to me so she wanted to leave cause she was tired of feeling lesser. She took my daughter away and went to Canada and that was that.
I then met a girl friend from Minnesota who I encountered one day while she was being attacked by a man bearing a large chef’s knife in a parking lot. I disarmed him and he scampered away. (Turns out he was her ex-husband who had stolen her son and fled back to Oklahoma) I was on the rebound and she was happy to be saved so I got a hero’s thank you and she went back to Minnesota in fear of her life not from me but her ex-husband.
I was alone and depressed I quit my job and they gave me full severance pay with overtime for a year. I was like 26 and ready to party. Katy was the name of my blow up doll and I dressed her up every day and she and I went out on the town everywhere together. Oh I know people laughed and scoffed but she was a real conversation starter. This was also my foray into actually picking out dresses. I loved shopping for clothes for her skimpy this skimpy that. My figure would not even come close to wearing that but anything and everything fit her. I attracted girlfriends by doing this too (not the dating kind the friend zone kind) and pretty soon I led a house with 11 female roommates and Katy. They loved giving me a make over as well and it was fun, and I felt pretty no clothes were involved just the make-up and nails. I practiced doing Katie's nails from then on as well. Her make up was painted on and I didn't think she needed any. Then one day Katy suffered a burn on her leg from a motorcycle and was unrecoverable. We had a funeral in the back yard and I insisted on burying her wardrobe with her. It felt like I just lost the fun side of me….. The severance check stopped but the parties did not they had evolved to be self-sustaining but the rent wasn’t getting paid. I told my roomies as well. I thought they would stop free loading and start chipping in and help pay the rent.But, instead they wanted me to strip for them I said "um what you want me to get paid to take clothes off". Yes they did for a preachers wife’s birthday party in a room in the back of the church.Without even thinking I said yes….
I arrived to strip and the room was full of women I was in the best shape of my life no I did not have a 6 pack but in a town with a pop of 5000 I guess I was hot and in demand. They treated me like meat and I liked it. It was great fun and the pay was excellent as in I made this month’s rent… but then the door opened and a lady said her husband was coming so I was led off by a lady who asked me to follow her through the maze of doors in this place. She led me to a heated spa and wanted to get frisky with me. She was hot and my age so I got in she slowly undressed and instructed me on all the things she wanted me to say to her. As she undressed I saw a corset and garter belt for the first time wow that was sexy! So I replied all whilst listening to a sermon about god in the background. It was erotic to say none the least but then before we got anywhere really the curtain was pulled back and there was the preacher. Worse this was not a Hot Tub it was a baptismal and they were in session. I thought well now I have done it nothing could get worse. Then it did as she said the one thing that could make it worse. She stared at the priest as he turned beet red and time almost stopped but before it did she said “Dad?” My soul left my body as I magically exited the baptismal and ran with no clothes on. I just ran. The dear reverend and some men from the congregation took chase. I searched the doors in this never ending maze till they were almost on me and then finally a way out. The grass on my feet and me flying free in broad daylight. As I ran down the road I felt alive, with an angry mob behind me of course. The convenience store in front of me just one stoplight intersection away. Of course there was a cop car right there at the intersection complete with officer inside when I ran by. The pavement was sooo hot and then the transaction to the cood floor of the store was soothing as I made my way to the beer. My plan was to push the cases back crawl into the cooler exit the cooler and flee out the back of the store losing the mob. It all went perfectly except my feet got stuck to the cooler floor a lot and it was really cold. I was not sure if I would look so manly streaking my way home LOL. I opened the back door of the store to come face to face with another cop. She said that there was no mob they arrested the rev at the intersection for attacking a police officer and had to take me in. However I was escorted to some of my old clothes that I had left there and told not to do it again. I was required to tell the story over and over for all my friends at the station. After all at one time I was there child. The Reverend did not get such treatment.
The next month came and more rent due. Well I did not want to be a stripper no more so I denied all such requests and then I received a request for a get together with no crowd just a one on one she wanted me to be her Gigolo so I thought why not the rent does have to get paid. So I went and serviced. Having watched the Hollywood movies I did demand to be paid up front and she did. I think she arranged it so that her husband would come home just after the deed was done more or less just magically showed up cause he barged in as soon as we were done and I never heard him pull up. It was so quiet in that neighborhood minus the screams he gave me about killing me and such blah, blah, blah I thought. After all he was no mob and I had already out run that so I grabbed the money and jumped out the window and ran streaking yet once again. The town newspaper put me on the Head line for the first time I wondered which page I would make this time. Then I heard the loud roar of his pick up and it was loud. He came tearing down the road trying to run me over in this monster truck. I dived out of the way but he did clip my heel and I spun in the air like a helicopter and landed in some bushes. I got up and ran all be it with a limp now but this time I cut through yards so that he would have to go around the blocks. I remembered a girlfriend’s house who lived in a house behind a house where I would stop and hide it was three blocks away so I had to make it. So I tried to push the pain out of my mind and run with tears streaking down my face. The first road came up and I could hear that damn truck roar as my feet met with the unforgiving blacktop the tires screeched around a corner I knew I could make it cause I was in the middle of the block so I ran. I hopped a fence and the pain came searing back when I landed. A dog showed up to give me encouragement to move faster. I hoped another fence and ran into goat heads and thought, no this will not deter me I will press on no matter what. So I quickly brushed off the stickers whilst in stride. The next road came up and he was all ready there parked and out of his truck with a bar. I decided to try to run around him as he swung at me and I ducked he hit the tail light on his own truck (yeah it was that tall) but I could not get up fast enough to dodge his foot as he literally gave me a swift kick in the ass like deep in the ass. Please remember I was naked at the time. This lifted me up enough to land on my feet running. He chose to not pursue but to get back into his truck and give chase. This gave me plenty of time to cross the next road before he even got there. From there I went straight to my friend’s house and knocked and knocked and knocked and an eternity later she answered the door. I was standing there naked and she answered with just a towel on. (LOL Writing this down it sounds like a porn intro) Frisky was far from my mind especially with the roar of the truck getting louder and louder. I kind of barged in while she asked me what was going on. She lived in a Loft so I could see she had company. I asked her to shut the door and then I told her everything. She laughed at me. Seems being a Gigolo is not for me either but the rent was paid. She had no men’s clothes for me only women’s she said. The thought enticed me to say the least and I told her I didn't mind borrowing some of those. So here is the moment I first dressed as a woman. She was a sexy seductress that was several sizes smaller than me so everything was super tight. The lady in the back of the loft giggled at me as she was wearing army fatigues and staring at me I thought well you got to do what you got to do. It seems I interrupted some frisky time between the girls and they were in earnest for me to exit, but I asked if I could just stay by the door till the sounds of the roaring truck dissipated. The clothing at the time did not come across as sexy or beautiful at the time just tight and restrictive. I did not feel good at all. The roaring stopped minutes passed it was time for me to leave. The lady in fatigues told me I looked good and hot as my farewell. All of a sudden I felt sexy, and I knew it but I had to go and I did. As I walked down the road in my spaghetti strapped top, miniskirt which showed my panties beneath, and flip flops which my heels hanged over the back of. I felt proud, heck I earned the rent I had made a new friend and I had clothes for the trip home. No cops, angry husband, or mob could bring me down. A guy mowing his yard stopped to look at me and whistle I smiled back. It was 20 to 30 blocks back home and aside from my huge head nothing else happened on the way home.
That is where I will stop for now. However for a teaser that lady in fatigues that thought I was hot, became, and is my wife of um 15+ years and that was our real first meeting with me in ladies clothes. Soo many things have happened good times, bad times, but cross dressing is fun awesome and not anything to be embarrassed about, I just want to look good before I tell people LOL.
Ashlynn Rose
