Cross dressing journey

Hello everyone I wanna tell you all about my cross dressing fetish and how it all started. Before I begin let me start by telling you all a bit about my family and myself. We are a family of three, my mom, dad and myself. Both my parents worked which gave me a lot of time to be alone. Although both of them worked it was my Mom who was the main bread earner of the family. Her name is Shikha and she is the vice president of a private company and earning a good salary apart from amenities like housing, car etc. We lived in a large 3 bedroom apartment in one the posh areas of the city. To be short my Moms earning were more than enough for the three of us. Dad on the other hand had a small time desk job in some govt office. It was not high paying but it kept my dad occupied. In short my Mom was the dominant person in our family not just due to financial reasons but also physical. My dad and myself were quite short. We stood at around 5” 3 and my mom was around 5”5. Moreover she had a habit of wearing long heels so when we were going out my mom towered above us by more than 3-4 inches. Mom took most of the decisions at our home and dad complied with each and every one of then. He knew he could not oppose mom in any way. Mom had instructed dad to submit his monthly earnings to her account. Whenever he needed some money he would have to request it from mom. She would make sure it was for a valid reason before handing it over.

Moreover my mom had a very active social life. Since she had a very important job she had to attend a lot of office parties. She also had a lot of friends with whom she would go out on weekends while me and my dad used to remain at home. I remember one night my mom was out partying with her friends she was quite late. At around 2 in the morning the doorbell rang and my dad ran and opened the door. Mom was leaning on a guys shoulder. She was dressed only in blouse and petticoat and another guy was carrying her sari behind her. They told my dad “We are friends of Shikha, she drank too much in the club and we had to carry her home. That’s when her sari opened”. They came inside and placed mom on her bed. It was really weird seeing my semi nude mom being carried by two guys while my dad stood in the side helplessly carrying her sari. One of the guys scolded dad for being so careless with mom. Dad hung his head down as the guys kept on insulting him.

Now my mom had always wanted a girl as her child from the very beginning. In fact till the age of 8 mom used to make me wear a frock at home. After that I started wearing male clothing’s till a few years ago. When I was 16 I suddenly had a feeling to wear girl’s clothes again. Now my school holidays were on Thursdays and Sundays. On Sunday everyone used to be at home so I couldn’t do anything on that day, but on Thursdays I was completely free. Both mom and dad would leave for work in the morning; the maid would come and would finish cooking and everything by 12. After that I used to be completely alone. I started to go through my moms belongings and would often smell her bra and panties. Now one Thursday after everyone had left I decided to try them on. I went to mom’s bedroom and stripped off completely. I stood in front of the mirror and looked at myself. Now there is one thing I hadn’t told u guys yet, I am very poorly endowed. My lund when erect stands at a length of 3 inches. I was very excited then and as I looked at myself in front of the mirror I got my tiny erection. Any way I selected one of mom’s panties and put them on. It was black in color and it fitted me quite nicely. Then I selected one of her bras and put it on. To make my breasts look bigger I stuffed it with cotton. Soon I was feeling very feminine and my erection was as hard as ever. After that I tried on one of mom’s nighty and I realized that I looked quite sexy in this dress. By this it was getting quite late and I slowly opened everything and put them back in the proper place so that mom did not suspect anything. The next week I did the same thing but this time I tried on some of mom’s jewelry like bangles and necklaces.

I kept on doing this every week till it was time for my summer vacations. Now I had everyday to myself and I decided to make full use of it. By now I used to dress up completely like a woman. I also used to wear nail polish and used lipstick. I used to spend my time dressed like this till 4 PM after which I would set everything back to its normal place. One day I was lying on my bed wearing a red salwar. I had done complete make up that day. I was also wearing bangles and a small red bindi. I was lying in bed fondling my fake breasts and I fell asleep. I was suddenly awaken by someone sitting beside me. I got up immediately and realized in was mom sitting beside me in her blouse and petticoat. After coming home from work she always used to go to her room and take off her sari before checking on me. She had the most astonished look on her face and she asked me” beta what happened to you, why are you dressed like this”. I didn’t know what to say and just sat there like an idiot. After a while I muttered something about being sorry. By this time mom was smiling and she said” beta since when have u been doing this and please don’t lie to me”.

I was caught red handed and there was no point in lying. I slowly replied that I had been doing this for the past 4 months. Mom was quite amused and began scanning my entire body. She stopped at my breasts and asked me what they were. I said “I have stuffed cotton in there to make it look real”. Mom slowly squeezed them softly and said” beta your breasts are bigger than mine”. As mom said this I began to blush and mom said” Its ok beta, I am not going to scold you, in fact you look quite cute in this dress and I want you to have it”. I was scared and told mom” I will take it off right now”. Mom scolded me saying” didn’t you hear what I just said, I want you to wear this at home, in fact I want your father to see you in this dress”. I was a bit scared but said ok to it. The rest of the day my mom asked me questions about my habits. I answered everything truthfully and was feeling quite happy that mom was not angry but was encouraging me to wear this. When dad came back at 7, mom told him to come to the bedroom where I was sitting. On looking at me even dad had the same reaction. He was bewildered out of his mind. Mom looked at him and said” from now on this is our daughter”. Dad didn’t say anything and just left the room. Mom then turned to me and said: don’t worry I will explain to him later on, but now there’s a lot work to be done on you if you want to become a girl, from now on I will call u Sneha”.

The next few days mom used to come back home early and used to train me to become a girl. Within a week I could wear a sari properly. Then one day mom brought me a wig and told me to put it on. After fitting it properly and applying make-up mom told me look in the mirror. I was completely astonished. I was looking at a good-looking girl in the mirror. Since my arms, fingers and stomach were slender there was no way someone could tell me that I was a boy inside (or was I). Mom then told me that there was one small thing left to do but that could wait for a while. That day for the first time I went outside dressed as a girl. I was so nervous that I was literally shivering. My mom told me to relax and said that I looked beautiful. I was wearing a green sari with a white blouse and mom was wearing a green salwar. First my mom and me went to a movie. This was ok because the movie theater was dark and my face was hardly visible. After that we went to dinner in a nice restaurant. This was the place where I was very scared once again but no one seemed to notice anything out of the ordinary. In fact the waiter referred to us as “ladies”.

This was all very exciting for me and my small penis had become quite hard. All the time I was thinking that I would go home and masturbate. After a nice dinner mom told me” bet you are learning very beautifully, tonight your training will be complete”. I was very happy on hearing these words and said,” thank you mom you are the best”. On reaching home I was going to my room to masturbate when mom called me and said “beti come to my room I have a small present for you”. When I went there mom told dad to give us some privacy and he quietly went to the living room. I was standing in front of mom and she was looking at me. She then said” beti take off your clothes I want to see something”. Soon I was in my panties and mom looked at me and said,” its ok, you can take it off”. I was quite scared coz I had not shared the secret of my small penis with anyone even my mom. I was so scared that my penis had shrunk to about 1 inch by now. I slowly slid down my panties and stood there. Mom looked at my shrunken member and looked at me saying” It is true that penis size runs in the family, your lund is even smaller than your fathers”. I hung my head in shame and mom finally spoke again” tell me something how many times do u masturbate”. I quietly replied “twice every day”.

Mom smiled and said” from now on you cant masturbate until I want you to”. Saying this she took out a small plastic device from her bag and put it on my penis. After she had finished fixing it I saw that it was a chastity device. Mom looked at it with an unsatisfied look and said” thank god, I ordered the smallest size, but even this is big for you”. I was a little shocked at this and asked her” mom wont you ever take it off”. Mom smiled and said” don’t worry about all that now, its too early to think about opening the cage. You will soon learn to love it. Even your father has one fitted on his lund. Initially he was scared too but now he loves it.” Seeing me confused my mom continued” I put the chastity device on your father a month after our marriage. This is one of the secrets as to why he is such a loving and obedient person even after all these years. He knows that if he disobeys me he stays locked up longer. In fact why don’t I call him inside now?” Dad came in and looked at me. He didn’t seem very surprised until mom told him to drop his pants. He hesitated for a few seconds but soon opened his shorts. It was the first time I was seeing dad naked. Like mine his pubic region was completely shaven and his small penis was enclosed by another kind of chastity device. Dad’s chastity device was white in color while mine was pink. Mom was smiling as she stood between us and she finally spoke” this is a very happy day for me; today the happiness of both the men in this house is controlled by me.

Let me go through the rules for Sneha. I have put the cage on your lunds because such small lunds are of no use to anyone. I cannot allow you to play with yourselves whenever you are alone like dirty boys. Moreover both of you are never allowed to tamper with the lock in the device. If you try to break it, it can cause serious damage to your private parts. When it comes off is completely up to me”. After saying this mom told me to put on my nighty and go to sleep. Even dad slowly pulled his shorts up and went to bed. This was about three months back. I now have my own personal wardrobe of female clothing. Whenever I am not in school I am dressed like a girl. In fact I spend most of my time dressed as a girl than as a boy. I have my own dressing table and mom has taught me how to use everything properly. I get my release about once a month now when mom opens my cock cage for about half an hour. Now the fact that I dress up like a girl is not entirely a secret. My mom told it to her sister who now knows everything about me including my cock cage. On my last birthday I received gifts like saris, lingerie, and worst of all another cock cage from mom. Mom smiled and said” Happy birthday beti, I had this one custom made to fit your lund”. I blushed and said “thank you mom”.

By now everyone must be familiar with my dressing habits and my family. It now became a normal habit for me to dress up like a girl at home and even while going out. My chastity device is still fixed on my lund and I get release only when mom wants me to. No one could tell that I was not a girl when I was dressed like one. In this part I will tell you how I got sexual with my uncle. It was summer and mom had taken a small break from office. She decided that we would all go to our aunt’s house. It was around 3 hours drive from our place. Dad had some work in office so he could not come with us. Mom drove all the way. She was wearing jeans and a t shirt. I was wearing a sari and some light make up. By this time I just loved wearing saris. Anyway we reached there at around noon. Both my uncle and aunt knew about my habits but uncle had never seen me in a woman’s attire before, so I was a bit nervous. After reaching their house we went upstairs and when I met uncle I could see that he was very surprised. At first he didn’t say anything to me but soon he got close to me. After initial greetings uncle came and sat beside me. He touched my hands and began stroking them slowly. No guy had touched me like that before so it felt a little strange.

After a while mom and aunt went inside leaving me and uncle outside in the living room. Uncle said to me”Sneha you look very beautiful, you look a lot like your mother”. Saying this he lifted and kissed my hands. It was the first time some guy had kissed me in a sexual manner. I was a bit scared but my small penis was pressing hard against the cock cage. Uncle then told me to stand up and saw my entire figure. He was scanning me like a hungry dog looks at its food. He then stood up and hugged me and said” Sneha we will get to know each other better in the next few days”. I simply smiled and said nothing not completely understanding what uncle meant. Then uncle told me to change and get ready for lunch. My small lund was really hurting at this point. I had never been this excited before in my entire life. I opened my sari and was dressed only in my blouse and petticoat. When I came out of the bedroom uncle’s stares had become even more intense. He slowly began to touch my stomach and navel when no one was looking. I didn’t oppose him because I was enjoying all this attention from a guy.

After lunch when mom and aunt had gone for an afternoon sleep uncle called me to a separate room and told me to sit on the bed. I meekly did as was asked of me. I knew that uncle was taking advantage of me but something inside me just told me to obey him. Uncle then lifted my feet and kissed them. My fingers all had polish on them and I think that excited uncle a lot. He licked each and every finger of mine. When he had finished he got up and sat beside me. He slowly put his hands on my breasts and started rubbing them. I now put artificial external breast implants made of rubber inside my bra. They look and feel real from outside. Uncle fondled them for a while and then moved his hands to my back. Basically for the next 30 minutes he fondled my entire body and I knew he was very excited because of the big tent in his shorts. He didn’t even try to hide it from me. After playing with me for some time he told me” Sneha you are a very beautiful girl, but I want to see you in all your glory”. He then indicated me to open my clothes and stand naked in front of him. I was very happy to hear this and slowly began to open my blouse and petticoat. Soon I was stark naked in front of him in nothing else other than my ornaments and cock cage. Uncle smiled and kissed me for a while in every part of my body. Uncle then played with my caged cock for a while and asked me” how often does your mother open it”. I replied that its sometimes once in 2 weeks. Uncle smiled and kept on playing with the cage.

Then uncle told me to bend down and show my ass. I did as he asked me to do. Uncle slowly parted my ass cheeks. He looked at my asshole and said “wow Sneha you have a very sexy ass”. I smiled and thanked him. Uncle then told me to dress up and said” Its enough for today, I will make you feel like a complete woman tomorrow”. Saying this he kissed me one last time and told me to go back to my room. I went away but after a while I quietly came back. I saw uncle was stroking his long dick and was moaning. I suddenly had the urge to go there and give him a nice hand job but I resisted the urge and went back to my room with my cock twitching like never before. Anyway that day passed with me horny as hell. The next mom went out with aunty and a few of her friends. I knew that uncle would not miss this opportunity to fulfill his wildest fantasies with me. In fact I wanted to satisfy him. As soon as mom and aunty had left uncle came to my room with a jar of Vaseline. I was sitting on bed wearing nothing but a nighty. He smiled and took the nighty off. I was sitting naked quietly on the bed and uncle began to open his clothes himself. As soon as he had pulled his shorts down his beautiful lund was in view. It was around 8” long and was as hard as iron. Compared to his lund I had nothing. Uncle slowly turned me around and applied Vaseline nicely in my ass. He plunged 2 fingers in and out of my ass for some time. Then he kissed me and said” today you will lose your virginity Sneha, are u ready”. I was very happy and nodded enthusiastically. He then slowly inserted his lund inside me.

It hurt when his thick member entered me but soon the pain was turned into pleasure and I started moaning too. I wanted him to fuck me forever. In fact my cock had started to dribble cum through the cage. I was basically being milked and I was enjoying the experience a lot. This continued for about 15 minutes and after that I could hear uncle give a loud grunt and I felt something hot oozing inside my ass. Uncle and me stayed in that position for a while and after that uncle slowly took his cock out. It was juicy and had cum sticking all over it. I really wanted to lick it clean and when uncle brought his dick close to my face I immediately gobbled his lund. I licked in it for a while and then uncle told me to stop and told me lovingly” Sneha this is the best sex I have ever had in my entire life. Please promise me that you will always surrender your lovely body to me anytime I want”. I smiled and said “yes uncle, this body is yours”. Hearing this uncle was extremely pleased and slowly put his cock back in my mouth. I began to give him a nice blowjob and soon he came in my mouth. I was more than happy to drink his cum. Anyway the entire day passed with uncle fucking me 2-3 more times. Mom and aunt returned at night and by that time I was completely spent and was sleeping. They don’t know about my affair with uncle and hopefully I can maintain this relationship forever. Anyone wanting to talk to me about my mom or abt my cross dressing habits can email me at [email protected] which is also my yahoo messenger id.