Here is a true story of my life as I grew up, publicly being a boy/man and behind closed doors being a girl/woman. I was straight, gay and/or bi all at the same time. The following stories are just short excerpts to describe my progression through life. Several are subject to stories in themselves. Please let me know what you think or if you would like a story on any aspect of this one. Thank you. Rachelle
Richard or Rachelle?
I was born a male as far as I can tell. But now, years later, I really question it.
I had four sister and no brothers. One older sister and three younger. My oldest sister, myself and my next younger sister were close. My youngest two sisters were eight and ten years younger.
The three of us, before the two younger sisters, shared a bedroom. We lived in a two bedroom house. My mom and dad had one. My older sister, younger sister and I had the other. So I slept there with my sisters until I was nine. Shortly after my next sister (sister 3) was born my Dad made a bedroom in the basement for me and my uncle. My uncle just got a divorce and needed someplace to stay until he figured out things.
All my life I grew up around panties, bras, nighties, girl clothes of every kind and lots of girl flesh running around doing all the things girls do.
As we were growing up I remember my two sisters and I would always play up in our room. Especially in the winter when it was cold and the snow was deep. One of the things we would do is to play dress up. My sisters would always dress me up as a girl and had me wear my mom?s high heels. I didn?t know any better, it was just what we did. My mom always thought it was so cute and would smile and encourage us to play.
As I started school, the dress up got less and less. I guess I realized that boys didn?t do that or the peer pressure kicked in. But, I always missed our play time.
I remember when I was around eight or nine years old. I didn?t like the way my boy clothes fit. So I had my mom alter my clothes. I had her sew the seams to make the legs thinner. It made my pants a lot tighter. They fit like a glove and I love it. No more baggy pants. They fit like girl pants but with a boys cut.
I also had my mom alter my shirts to make them tighter fitting. I don?t think the shirts ever looked that good but they were better than the baggy boy look.
She also made me a special shirt made of polished cotton. It was a shiny black and more of a blouse than a boy?s shirt. I loved it. My mom really like doing this for me. As I look back I think the more of this I asked the more she liked it.
When I was sitting at my desk in school my teacher would come up to me and rub on my shoulder telling me how nice I looked. She especially liked my shiny black shirt.
I really don?t remember what happened, but I stopped doing it. I don?t know if it was peer pressure or my Dad. But my mom stopped altering my clothes and I dressed as all boys did. When I was eleven years old, another boy and I were out in the woods playing. There were woods behind our house filled with paths. All the boys in the neighborhood played out there. I don?t remember what lead up to it but my friend said he wanted to suck my dick. No one has ever done that to me before and I have never heard of anyone doing it. He ended up on his knees and my pants pulled open to give him access to my cock. He came forward and took my cock into his mouth. I still to this day remember the feeling of his mouth wrapped around my cock. It felt so good!!! He slowly started sucking it in and out. Every once in a while he would look up at me. He told me that is what boys were supposed to do. He sucked on me for a while. I don?t remember if I came or not. All I remember is how good it felt.
He want me to suck his cock and I said no. I sort of felt guilty. After that we went home. I don?t think we ever played together after that. He became very gay and died in his early twenties. He lived with his uncle and not his mom, dad and sister who lived a couple blocks away. Looking back, I think he was being sexually abused by his uncle.
But that incident got me started. After that I would masturbate all the time. I also started looking for other boys and men to suck my cock. I did not want the boys around where I was located to know so I looked everywhere except on my end of town. I didn?t want to get the gay label or queer as it was called then. I use to hitch hike to get around town. Downtown was about seven miles away. Were my Dad worked was about four miles away. Sometime I would find men who picked me up wanted to suck my cock. I would always let them. A couple even paid me to let them suck me. It was great.
Some of the men wanted me to suck their cock but I always said no. A couple even offered to pay me. I still said no. But I was always so curious, especially when they would pull out their hard cock and jack off as they sucked my cock.
As I entered High School I discovered the adult book stores downtown with glory holes. You were supposed to be eighteen to enter but they always let me enter starting at fifteen. I guess they enjoyed a young boy in there. I use to enter a booth and watch gay movies, stick my cock through the glory hole, and it never failed. I always got my cock sucked, cumming in the cock suckers mouth. Sometimes more than one man who would suck my cock. I love it. The more the better.
Some of the men would stick their cocks through the glory hole for me to suck them, but I never did. But after a few time I would take it in my hand and jack them. I remember the first time I touched a man?s hard cock in the book store. I think it changed me forever! I liked the way it felt and I liked the way a man would react when I played with it. They would want me to suck it but never did. Sometimes I could get them to cum, shooting cum out into the air and falling to the floor. It fascinated me.
My Dad had a gas station with a service garage. I started pumping gas there at the young age of eight. I worked there after school and weekend all the up to and through High School. Since we had a service garage I also started fixing cars. By the time I was a senior in High School there wasn?t a part on a car I had not changed or fix.
The first time I had sex with a girl was at the gas station. There was a girl who lived a few blocks away. She would always come over and flirt with me when I was working nights by myself. We were both sixteen but went to different schools. At closing time, I did all the things I had to do to close down the station for the night and she just stuck around. We started kissing and making out. Both of use were hot. I locked the doors and we ended up in the back seat of a car parked in the garage. We were kissing and clothes were coming off. By the time we were naked we couldn?t wait. She spread her legs and my hard cock entered her pussy. I started pumping. It didn?t take me long to cum into her hot wet pussy. I don?t think it was too good for her, but I felt great. I lost my virginity with a girl. Bisexual!
Back to High School for a bit. I was never very big. Most of the boys were bigger than me. In fact I was one of the smallest boy in most of my classes from kindergarten through high school.
As I worked on cars all the time, I got mechanic hands at a young age. They always looked dirty no matter how much I scrubbed and cleaned. Oil and grease were embedded in my pores. Most of the girls didn?t like my hands and being small made it hard for me to date the girls in school. But I did find dates with girls from other schools. It never bothered the boys. While in High School long hair was just starting to become popular in men and boys. So I let my hair grow. It wasn?t real long but it was longer than most boys around the area. Now being a small boy with long hair made me a bit fem looking I guess. The men working at my Dad?s gas station started calling me Sally when my Dad wasn?t around. I never made a big deal about it and tried to ignore them. But inside I really liked it for some reason. But I always tried to ignore the feeling inside. (Now I wish I serviced them in the back room. It could have been so much fun.)
Back home, when no one was home I would dress as one of my sisters. Their clothes fit me really good. I would put on panties, a bra, a dress, nylons and shoes. I would parade around the house dressed like this doing different things. It felt so nice being dressed and out of my boy clothes. I would always end up jacking off while dressed. I would cum in my hand and then go the bathroom to wash off the cum. Sometimes I would take a T shirt, girl clothing, or something soft, lay it out on a bed, lay on top of it and pump my hard cock on it. I would always cum really hard as I dreamed about fucking, both fucking someone and someone fucking me. Yes I started fantasizing about being fucked by men. This was probably while still in grade school. I guess it was seeing men?s hard cocks as they sucked me. I continued dressing off and on when no one was home until I graduated from High School and entered the Army. I never did get caught but sometimes I think my sister knew.
Three years later I got out of the Army. I didn?t really do anything in the Army except to find men to give me an occasional blow job. I started college using the GI bill. I started looking for guys to service me, to suck me off. I found many in addition to the use of the glory holes in the book stores downtown. I also dated the college girls. It was a lot easier in college than in High School. I also discover the Steam Bath where gay men would hang out and have all the sex they wanted. I loved going in there seeing all the naked men fuck and suck each other in all sort of positions. I loved getting my cock sucked.
The steam bath in itself has many storied over the years. Every time I go home to that area I visit it. I have had lots of experiences there but are another story in themselves. If you would like t hear about them let me know.
I lived by myself for the most part. But after a couple years I had a girl friend who moved in with me. She lived with me for about three years. I hadn?t dressed in a few years. Not since I left my childhood home and all my sisters when I entered the Army. Now there were panties, bras and all the rest again but now there was also lingerie!!! All my dressing memories came back. I started dressing in her clothes when she wasn?t home. I would just do the things around the house just like I was a girl. Again I would end up jacking off. She never caught me, but it was fun. I really enjoyed dressing.
I dropped out of school for a couple years and ended up going out of state to another university.
I dated a few women but nothing serious. But I also continued looking for men to suck my cock. It wasn?t very hard to do. It seems like after a while you know where to look and what to look for. Again I only want to get my cock sucked. One night I was at a remote rest stop. I was looking to find someone to suck my cock. Someone finally came in. He entered the stall next to me, tapped his foot and we started talking. He invited me out to his van. I accepted the offer.
We got in the van. He asked me to take off my pants. Not thinking too much about it I took off my pants. He proceeded to suck my cock. As he did this he took off his pants and started playing with his hard cock. After a while, he stopped sucking and told me to suck his cock for a while. I said I didn?t suck cock. I just wanted my cock sucked. He didn?t like my answer. He grabbed me, flipped me over and raped me. Fucking my virgin ass and filling it with his cum. He was a lot bigger than me and I could not get away from him nor could I stop him from rapping me. When he got done fucking me, he threw me out of the van along with my pants and shoes. I was glad no one else was there as I stood there without pants.
My ass hurt so bad, nothing about it was enjoyable. I never wanted to do that again.
A couple years later I got married to a young lady that I met in the dorm during the first year in the out of state University. After we got married, we moved out to the east coast. Panties, bras and all the rest were back again. I loved that part of it. Again I would dress when she wasn?t home. And again I looked for men to suck my cock. But something happened here.
I was working on the seventh floor of a 22 story office building. I discovered a rest room with a glory hole on one of the lower floors. I went there a couple time for blow jobs from the men on the other side of the glory hole. Then one day I came into the stall. There was already someone in the adjoining stall. As I sat down on the toilet, the man stuck his cock through the glory hole for me to suck. I didn?t know what to do. I took his cock into my hand and slowly approached it. I thought to myself ? what the hell why not. I took it into my mouth a little at a time. I never did get it all the way in. But soon he started humping my mouth. I felt his cock going in and out. Soon he moaned saying he was going to cum. But he didn?t give me enough warning to pull off. He came in my mouth!!! It seemed like a lot. I swallowed it all. He got done, pulled up his pants and left. I sat there for a couple minutes sort of in a daze thinking about what just happened. From then on I sucked cock!!!
So now I was dressing in my wife?s clothes when she wasn?t home and I was looking for men to suck me but now also looking to suck them. My ass was out of bounds remembering the rape.
After a couple years we moved back to the mid-west. I was still dressing when my wife was gone. And looking for men when out and about. I don?t know if my wife knew or not, but she started buying me bikini briefs. She would tell me how nice they looked on me and wanted me to wear them all the time. I also like the way they felt so I wore bikini briefs and all my tighty whities slowly disappeared. More bikini briefs would show up. I had bikini briefs in many colors and a few had different patterns. I loved wearing them and my wife?s encouragement.
Every once in a while she would have me dress in her panties and bras or a nightie of some sort. We would have our laughs and giggle but it never amounted to much. She tried to tie me up a couple time, but I would never let het. One time she had me crawl into our dog cage we used when traveling. She said she wanted to see if I could fit. I did! She looked me in and there was nothing I could do. Trapped! She verbally humiliated me some. I got pissed off and she finally let me out. I didn't get mad but I sure put on a show on my displeasure. Inside I sort of enjoyed it but I could not let her know.
Around this time, a growth of tissue started growing within and extending outward form my ass hole. It was getting long and thick extending outward about half an inch. After a while it started bleeding when I would wipe. I finally went to the doctor to see what it was. They tested it to see if it was cancer. It was not. They said they could probably cut it off but they recommended against it because of the location. So I left it. Along comes the internet and all the resources and references available. I started searching the growth to try to figure out what it was and how to cure it. After many searches over many days and many hours, I came across a German reference on how to get rid of the growth. The article said to use a butt plug. The plug would put pressure on the growth. The pressure would cause the body to absorb the nutrients rather than the growth. After a while the growth would start to shrink and would totally disappear over time and continued pressure.
I was already going to adult book stores where they sold all the adult toys and butt plugs. So I went and bought my first butt plug. It was about as big as my finger!
I was excited at the thought of getting rid of my growth. I also bought some KY jelly per the instructions. I got home, stripped off my clothes (no one was home) and began the process of inserting the butt plug. I lube it up brought it to my asshole and slowly pushed it in. This was the only thing that entered my ass other than when I was rapped years ago and the visit to the Doctor a few months ago. It hurt and was really uncomfortable as I pushed it in. I felt like I was going to pass out and got hot and sweaty. I didn?t like it at all, but I wanted to get rid of the growth. I finally got it in and my ass closed around the narrowing before the pad that keeps if form total insertion. I could only keep it in for a few minutes before my muscles would start spasming, cramping and trying to push it out.
I had an office to myself so I brought the plug to work the next day. I inserted it every day and left it in for as long as I could stand it. It got easier and easier to insert it and I could leave it in longer and longer. My ass was loosening up. I would pump it in and out and I started enjoying the feeling. I got to the point where I would leave it in all day long. I would go out and about and do everything with the plug inserted. One day I was in a liquor store and I sneezed. I blew the plug out of my ass. I had a big lump in the back of my pants ? it was so embarrassing.
The next day I went and bought the next bigger size. Again I struggled to get it inserted. It really stretched me out. As before, I left it in all day at work going about doing my business. I was liking the way it felt. I would take it out before I went home and re insert it when I got to work. Over time I stretched out more and more and it got easier and easier to insert. I started pumping it in and out when I inserted it and before pulling out to go home. I was really beginning to love this feeling and having the plug in my ass. It got loose enough that it would fall out into my pants, so I bought the next bigger size. My ass was plugged nearly every day for probably a couple years by this time. Some place along the line the growth totally disappeared. I have no idea exactly when, but one day I was searching for it and it wasn?t there. But by this time I loved having the plug inserted and I kept doing it.
I started buying dildos and began fucking my ass. I started with small ones and worked my way up. Sometimes I would use the dildo at the same time as I was plugged. I really just loved having my ass filled and stretched. One thing lead to another and the next thing I knew I started looking for men to fuck my ass. So now I was looking for men to suck and to fuck me and dressing at home when no one was home.
My marriage starting failing for many reasons not associated with dressing or being bi. My wife never knew. We separated and I rented a small house about 20 miles away. For the first few months I did nothing but to find men for sex. I had several and several had me. Then I started dating women I met online on adult sex dating sites. I met several, but one in particular would encourage me to find men. She was the first person I ever told I love having sex with both men and women. She didn?t know about my cross dressing but she would help me find men and I would help her find other men. She was married and just wanted to be fucked by as many men as she could. We started setting up some threesomes but her husband found out about us and put an end to it.
During this time I also found a boyfriend. I would go to his house four or five times a month. He would stay hard for a long time and I loved it. He would fuck me over and over in every position imaginable. I was his boi. One Friday I went over there. He answered the door completely naked anticipating my arrival. I entered his house and we passionately embraced with our tongues playing with each other. As we were standing there embracing, I felt another person come up behind me and I got sandwiched between two men. Both naked. My boyfriend said he had a surprise for me. Two cocks for my pleasure.
I was fucked and sucked cock in more positions I knew existed. I absolutely loved my surprise.
My divorce came through and I bought another house. After a few months a girlfriend moved in with me. Panties and bras were back. Again I dressed when she wasn?t home. I did tell her I was bi and had sex with men. She wasn?t too thrilled but was curious. We were out one evening and we met a gay guy. He and my girlfriend flirted to no end. We ended up meeting him at another bar a couple nights later. One thing led to another and we ended up having a threesome. My girlfriend wanted to see two men doing each other. We both enjoyed it but we never did hook up with him again. We tried a couple times, but she lost her interest.
I also told her about wanting to dress a woman and go out to see if I could pass. She never thought it was a good idea and we never did, but I continued dressing when she wasn?t home. We split up and I took a job on the West Coast in Oakland. Gays and cross dressing was a lot more accepted here than in the Midwest! It was an education!!! I stated buying my own panties, bras, blouses, shirts, dresses, hose, jeans, makeup, lingerie, shoes and heels. I also bought a wig and some breast forms. Now I was really playing. I really enjoyed dressing but was afraid to go out. I was always searching the internet for cross dressers and dating sites. I started conversing with men telling them I was cross dressing. I ended up having several dates and was being fucked like the woman in me really wanted. I really enjoyed it and still do. (subjet of many other stories.)
One other thing, as long as I remember I always get emotional and would tear up when watching chick flicks. If no one was around I would cry like a girl. If others were there I would always have to be a man and hold them back.
Now I am dressing and going out more and more as a woman. I have dates with men and couples as a woman. I just ordered some hormones to see if I can grow boobs and to widen my hips. I am scared to death about family, friends and job knowing but I really enjoy being woman. I haven't dated a woman in over three years and my cock gets hard thinking about being fucked by a man or sucking cock. It does not respond to woman anymore.
Am I woman or am I man? What am I to do?