I lost my anal virginity when I was nine and by a friend of my sister's father. I’ll give a little history leading up to that wonderful day.
His daughter had told him of my always insisting I was a girl and constantly wearing my sister’s clothes when I was seven. Most all that knew me knew of my beliefs and demands that I wasn’t the boy they all said I was but that I was really a girl. It was then that he began to take a great interest in me. Talking to me when over at his house playing with his daughters and my sister. I remember that day when I was seven that he asked me to come inside while we all were playing in his backyard. Inside he offered me a glass of soda and then asked me to follow him. We left the kitchen and I thought we were going into the living room but instead headed down the hallway. We were soon in his bedroom. There on his bed all laid out were beautiful dresses, socks, shoes and hats. He told me he had heard that I felt I was a girl and he believed I really was one and he wanted to help. He said that whenever I was over at his house I could wear clothes such as those lying on his bed. I was so excited and started touching the cloth of the dresses and the shoes, not like what I was always made to wear but cute girl shoes. I was so excited and so happy. He told me that those were mine and more could come. He had three daughters, two older than I and one my age. Thinking today clothes for me to wear were not a problem. He asked if I wanted to change and dress as a beautiful girl rather than the boy things I had on. Without even thinking I began taking my clothes off and was soon bare except my sister’s panties I already had on. Mr. H, as I’ll call him said I should remove the panties I had on and wear a pink pair that he held with ruffles. I was then standing there completely naked and was shaking in my excitement of being dressed as I always dreamed. He then began telling me how beautiful I was. He then explained that I should tell no one what we did with the exception of his daughters and my sister and only about his allowing me to dress as a girl at his house. It was our secret. I now I know that “it” was what would come later in my education that was the real secret.
My uncle had helped me when I was five when my parents ask him, a bachelor, to help me understand that I was a boy and I began spending time and weekends over at his place. Instead of teaching me that and having me be a boy he would let me be the girl I knew I was. It also included learning things a girl needed to do to please men. He had explained that yes I was a girl but that I was a special girl and as such needed to be good at being just that kind of special girl. I was really happy when I was with him. Soon that was discovered and all contact was cut off. I was devastated.
Now here was another adult and one that believed me and wanted to teach me how to be a proper girl when everyone else kept saying I was a boy and that was just plain wrong. I knew I was a girl, my mind and heart were that of a girl and I hated my parents and others saying I was not. So when he said it was to be our secret and the results that happened because of my uncle's help, I kept it a secret. It was one I kept till he died. I saw him most everyday till I left home at 18 and every time I was home till he died when I was 26.
Anyway up till I was nine all our sexual play was mostly oral; I had continued my education of orally pleasing a man that my uncle had started. There was never a better student than I was. When I was nine he offered to take my sister and I along with his daughters to Salton Sea in the California dessert for a week of boating, swimming and just fun away from the house and neighborhood. I was so happy because I knew that the whole time we would be gone I was able to wear only girls clothes I was so excited. It was so wonderful. As soon as we left home we stopped at a service station and in the Bathroom he dressed me all up. A pink pair of panties, pink socks and sandals, he then had me raise my arms and slipped a cute sundress over my head. He kissed me and called me his special daughter. I did notice the bulge in his pants as he dressed me but he told me that later we would take care of that.
We walked out of that bathroom and when we got in the station wagon the girls were all saying that was more like it. They all said that I looked so happy when I was dressed as a girl. Every kid in my neighborhood knew I said I was a girl and when I could I wore girl clothes so to his daughter and my sister they always saw this happiness and excitement when I was in my world, the world of femininity. So away we drove with me sitting right next to him and the girls in the back seat and the rear of the station wagon. Five young girls and him singing and just having fun. Every so often his hand would find its way up my sundress and under my panties. Mummm it felt so good. We stopped to eat and walking into the restaurant I was at last the girl I always knew I was and everyone in there could see me. Mr. H held my hand as we walked to our seat I stayed and he kept me always at his side.
We arrived at their one room cabin which also had a travel trailer next to it late in the afternoon. The four girls he said were to sleep in the trailer and he and I being a "special" girl would sleep in the cabin. To the girls that seemed natural. I was excited because this would be the first night sleeping with him. I was wearing a pink nightgown he had given me. He said he bought it especially for this trip and me. I so loved him. Under the covers I just snuggled up against him and listened to him tell me what a beautiful girl I was and how I looked so happy on the drive. I told him that I was very happy and just wished I could always live at that and I always hated to go home. His hands began roaming all over my little body and kissing me. He removed my panties and I only wore the gown. He took my small hands and placed them onto his now hard cock. He asked me to rub it as he had taught me. As I was doing this he began playing with my little “thing”. I never called it my dick or cock but Mr. H always called it my girl clitty. He was really excited and asked me if I wanted to suck his cock. Wanting to please him for all the wonderful things of the day I said yes. I scooted down the bed and using my hands took his cock into my mouth as I had learned he liked it. I was soon sucking and wanted to make him cum because I knew that made him happy. It was what I had learned well making a man happy. He told me I was getting almost perfect and that I was making a beautiful girl and would always please a man as he should be pleased. Soon his cock was pulsing in my mouth and those moans he made just before he came started. I never before wanted him to cum more than at that moment. It had been a wonderful day a day that I was out where everyone could see me as the girl I was. I sucked softly normally but I was pushing my mouth down on his cock like I never had before. It was all slick with my saliva. He then began bucking his hips and coming. He held my head tight against him and soon his cum was filling my mouth. More cum than I ever felt he squirted into my mouth before. I was trying to do as I had been taught, swallow it all, as best I could. He was crying out how wonderful my mouth was and how good it felt. I softly suckled his soft cock licking what cum I had missed. He then said we should get some sleep as tomorrow would be a busy day. I snuggled up against him with my nightgown up around my waist and fell asleep tasting his cum in my mouth. The last thing I remembered was him fondling my girl clitty.
The next day was one out on his boat and swimming. I had a wonderful one piece bathing suit that belonged to Darlene his daughter. Being able to wear a girl’s bathing suit was so wonderful. At the marina he introduced me and my sister to his friends as friends of his daughter's. I was always called sissy Michelle by everyone in the neighborhood and school which was a derogatory slur of Michael my name. For me though it never hurt because to me it was an affirmation to what I was, a girl and yes a sissy. So I was introduced by name as Michelle. That has to me always been my name. Now it for six years has been my legal one.
On returning to the cabin we had a Barbeque and off the girls went to play. Mr. H said I should get out of my bathing suit and wash the sand and salt off me. There was a large galvanized tub on the deck. He told me that’s what they used to bath in. You must understand that their cabin was really isolated. No other place could be seen from their place. I was just flat dessert. So there on the deck Mr. H filled the tub and I was going to take a bath. He was going to give me a bubble bath. The girls were off playing somewhere so it was just us. He bathed me and tenderly washed me all over. As he did so he told me that that night he had a wonderful surprise for me as I had been such a good girl. I enjoyed being out in the open naked being bathed by him. After the bath I sat on the chaise lounge naked and dried in the sun. When the girls returned they all teased me about being naked and that girls were more modest than that. Darlene just looked at her father then me and smiled. Darlene and I were very close all our lives f dressed in growing up. I had later had a crush on her but she always denied my advances because as she put it “I belonged to her father” So into the cabin I went and put on my night gown with a cotton pair of panties. I went back out on the deck. As evening came we all sat up playing games in the cabin. Later he said it was time to go to sleep as tomorrow was going to be another long day on the water. Away the girls went to the trailer with Darlene smiling and giving me a wink. Once they left and Mr. H asked if I was ready for bed. I said yes but wanted to know what the wonderful surprise was. He said just get into bed and I would soon find out. So I hopped onto the bed giggling in happiness. This was my second night sleeping in bed with Mr. H and a wonderful surprise waiting there. Mr. H went over to the sink and cleaned up. As he walked to the bed he took off his clothes. He climbed into bed naked. I started removing my nightgown but he said to only remove my panties. I did so quickly.
Once in the bed he hugged me closely and began rubbing me softly saying how beautiful I was. He said he was so lucky to have found such a special girl as I was and what a good learner I was. He told me that several of the guys at the marina told him what a find I was. I was so drawn into his spell. He said I was truly a girl and truly a special one and as I grew I would be a man’s dream. He said I was one of only a few girls with a body and the exceptional talents in the way I was able to use it. I was just so happy. As we hugged and his hands wandered around my young body I noticed a difference that night. It was his new interest in playing with my butt. He asked me to suck his cock which I was so happy to do for him. I started sliding down but he said no. He asked me to lay with my head at his cock and my feet at his head. As I took his soft cock into my mouth he just moaned “that’s my girl”. As I was sucking his cock which way hardening with what my mouth was doing his hands again went to my ass. He kept rubbing it and running his fingers along the crack and stopping at my little hole and pressing. He asked me if it felt good and was it alright and I just nodded, my mouth filled with his cock in acceptance of this new wonderful feeling. I never knew that that part of me with his rubbing could feel so good. I then I noticed his finger was all gooey with something and he pressing his finger on my hole and he was getting firmer in his pressures against its opening. The feeling was amazing and all I could do was press back against his hand as it felt so good. I was soon lost in a pleasure a young child as I was normally could never experience. I know today that what was happening is considered wrong but to me it was what saved me from misery of being something I wasn’t and al my life never wanted to be, a boy. I was a girl and Mr. H, even my uncle let me be one and even taught me things I needed to know to survive later in my life. I loved doing what we were doing, it felt good, I wanted it thus even in my child’s mind it was consensual.
He kept rubbing the small hole and pushing against it. Each push against it went furthering into my hole. As I was sucking his cock, his hand and that wonderful finger was pressing against my tight hole pushing and suddenly it slipped in. I jumped in surprise. He held me tight and pushed his finger deeper. He then pulled it back but not all the way out then pushed it back in. As he was pushing it in then out he whispered, “How does my girl feel?” With my mouth filled with his hard cock all I could do was moan and nod my head. All this, I learned later as preparation for what was to come all took place over an hour. So he had gently taken over an hour to loosen me up enough to push his finger in. It had surprised me but soon I just could not concentrate on sucking his raging cock. I could only concentrate on that wonderful yet sting feeling of his finger in my tight hole. I was lost in a pleasure I’d never felt before or even imagined possible. He continued to push his finger in then pull it out, then back in again.
As the rhythmic motion was so wonderfully exciting, he asked how it felt and all I could do was moan. I wanted more. He said my girl pussy was so tight and felt so good. I heard his words “girl pussy” and I was in heaven. My body was his for whatever he wanted. He put more of whatever he was using on his finger and pushed it into me all the way in one fast motion. I may have been a nine year old child but there in that bed at that moment I was a withering mass lost in sexual pleasure. I never knew something could feel so good. He again asked how I felt, and again all I could do was moan ever so weakly and nod my head yes.
Then he asked if I wanted to do something only a woman could do to please her man and he knew I was a woman even if I was a young girl. He said this was my surprise; he was going to make me a woman, his woman. He said he wanted to put his cock in my pussy and by my letting him fill me I would be giving myself and my body to the man who loves me. I said yes so excitedly, all I wanted to do was to please him in whatever way I could. He was my man and I was his girl and my body belonged to him. I was there because of his love for me and yes I was his girl.
He had me get on my knees with my elbows down and my butt in the air. He again pushed in his finger up inside me and by this time it was easily going in. He then added a second. I was completely lost in lust; even as a young nine year old girl I wanted his cock in me. I needed his cock in me. He then suddenly pulled them out and the emptiness saddened me. As I kneeled there wondering I felt him move up close to me and him holding his cock and rubbing my ass with it. He then rubbed it around my hole. He began pressing it against the entrance. All the time he was saying what a wonderful girl I was. I felt his cock which was much bigger than his two fingers pressing into me. Suddenly there was a real sharp pain. He had pushed the head of his cock into my ass. He was rubbing my butt and whispering how wonderful it felt. He was telling me how beautiful I was. He told me how sexy it looked to see me bent over with my ass in the air and his cock pushed into my stretched hold gripping it tight This he said was what girls were meant to do, offer their body completely to their man. I so wanted to do that that I just had to bear with the stinging and please him. I wanted, I needed to show him I was his girl and by giving him my body for his pleasure he would see and believe it.
It took what seemed like hours but soon I felt his dick hairs against my butt. He leaned over and began kissing my back. He kept saying over and over hot it was inside me and how wonderful it felt and how wonderful I was. He then said I was truly and without any question a girl and now a woman. He had only got it all the way in when I felt his cock start to pulse and it seemed to get bigger. He began that moaning when he cums. He leaned over my back once more and whispered he was sorry, he said he had climaxed. He then with his cock still inside me explained that his cum, the same cum I had many times tasted and swallowed when I sucked his cock was now in me. It was put inside me as it should be. He said that he had fucked me as a man should fuck a girl and filled me with his cum. He had me roll over on my side in a spoon manner with his cock still with his cock still up inside me. As I fell asleep I now knew I truly was a girl, even a woman. I now really truly believed it. I had taken a man into my body as a woman could and he squirted into me that gift, a gift both he and my uncle always said was a man's gift to his girl, his cum. It was his gift to me for making him feel and experience pleasure only I as his girl could. I slept so soundly that night as I knew no matter what anyone said or what ever they showed me, I was a girl, I had proved it.
The next day, our third, my butt was sore but I was just glowing. The girls noticed my giddiness and happiness the next morning. Darlene kept smiling and when no one was looking kept asking if last night I had a good time. All I could do was smile and nod my head. I learned as I wrote earlier that Darlene knew that her father and I were having sex. I also learned later that when we talked about what her father and I did it got her excited. I never told her boyfriend that many of the blow jobs and fucks he got was because our talks got her horny.
All that day I could not wait till bed time and again do what he had said we had done, “fucked”. That night he said I should let my pussy rest, so I sucked him till he came in my mouth. I really wanted to feel his wonderful cock fucking my ass and I was not a happy girl. He kept telling me to stop pouting; but all I wanted was to feel him in me again. Too fill me with his cum.
Well during the remainder of the seven days there I did everything I could no matter what time of day it was to get his cock in me. I was hooked; I loved as he said "fucking" He told me that I was a natural. From that day till I was in my twenties I loved him and loved him deep inside me. Fucking me long hard and deep and fast for as long as he wanted, I was his girl then I was his woman.