Feel like a Woman

I was only 6 or 7 when I started dressing up in some of my sisters clothes. I was a small boy named Oliver very thin but tall, my sister was 5 years older than me and had hit puberty and was wearing training bras and nylon knickers. I loved to try them on and looked in the mirror and wished I was really a girl instead of a boy.

Fast forward 7 years, my sister Roseanne was now 18 and driving a car and had a boyfriend. She had developed a knockout body she was tall and slender with long legs and good sized boobs. Meanwhile I was still slim and had grown tall, I grew my hair long and had virtually no body hair even though I was well into puberty.

Every chance I got when know one was home, I tried on my sisters underwear and clothes. I didn’t have the hips or boobs but I still fitted into her underwear and padded the bra to simulate boobs. I loved some of the dresses she had and I particularly loved the stockings and suspender belt she had.

I would dress up and walk around the house, I even wore her high heels, they were a bit big but I managed. I tried to walk like her, putting one foot in front of the other. After a while I found it quite natural to walk that way. I sat in front of her mirror and started to apply makeup and did my hair. The first few times were pretty bad but the more I practiced the better I got. It really felt natural when I was dressed up and when I looked in the mirror I saw the person I wanted to be.

I had a pretty hard time at school, I was not that athletic and preferred to hang around with some of the girls rather than the guys. I think the girls thought I was gay and they were safe with me, the guys also thought I was gay and but picked on me. The thing was I had no thoughts about guys, I had no interest and the last thing I wanted was to have sex with a guy. My wet dreams were always about making love to a girl, I wanted to make passionate love to them but never fucking them as a guy I wanted to be a girl when I made love to them.

By the time I was 18 I realised that I was transgender I was sure I had always been a girl in my mind, just born in a boys body. My body was like a girl, I was tall and thin, I had no body hair except my underarms and pubic hair. I had virtually no hair on my legs, arms or chest and didn’t even have facial hair. I had long shoulder length hair and when I was wearing say jeans and a t-shirt, I frequently had boys mistake me for a girl especially from behind. Even my voice was feminine it was high pitched and on a phone I frequently was mistaken as a girl.

Roseanne had realised a few years earlier and she helped me in buying some of my own feminine underwear and she let me wear some of her dresses. I had no problem as we were almost the same height and weight, even the same shoe size. I only ever dressed up at home but I was doing it all the time, I was obsessed with being a girl.

I went to a clinic and they referred me to a psychologist, it was hard opening up to this women but the more I talked about it the more I realised that I wanted to be that person of my dreams, I wanted to be a women. The psychologist said that there were drugs that they could prescribe that would help with a change and even gender reassignment eventually. First however I had to be sure that is what I wanted, she suggested that I go out into the world dressed up and experience that before I went too far. She did however give me estrogen tablets that would suppress any testosterone my body produced and slowly start the change.

I spoke to my sister and she agreed to help me to go out into the world dressed as a women, at least for one night. She suggested the following Saturday night we go to a nightclub that had a big bar and dancefloor and she would invite along a number of her girlfriends to have a “girls” night out. I couldn’t wait.

Saturday arrived I woke up early I couldn’t sleep my mind was racing, I was both eager and scared. I took a long hot bath, I shaved my legs not that there was much to shave, my underarms and trimmed my pubic hair. My cock was very small especially when it was flacid. I could get erections but even then it was only 4” long and not very thick. When I dressed it my silky underwear I was able to tuck it back with little trouble.

After finishing my bath and drying my hair, I put on a robe and went to my room. My sister said she had a surprise, she had arranged a girl to come and give me a manicure, pedicure, false nails, false eyelashes and even do my hair and makeup. She was even going to give me a full deep massage with exotic oils.

A girl named Jan turned up at 11am, my sister introduced me as my little sister “Olivia” who was going out on the town, a real coming out party. Jan said she had a few special customers like “Olivia”. I spent most of the day getting the works, it was wonderful. I felt some feminine, all the pampering, all the fussing it felt so natural.

When Jan finally left at around 4 o’clock , Roseanne took me upstairs to her room and on her bed she had laid out my underwear and a number of dresses. She had 4 matching bras and panties, garter belts, stockings and there were a number of dresses and pairs of shoes. I spent the next 4 hours trying on different underwear, dresses, shoes my mind was spinning, every-time I looked in the mirror I couldn’t recognize the person looking back.

I ended up with a black bra with white lace frills, it was an underwire bra and I had a pair of silicone fake boobs that I had been bought that gave me a C Cup. The panties were also black and fitted high on my waist, I slipped on the garter belt and then carefully pulled on he silk stockings. The dress I chose was little black dress that had straps and a v neck not to deep it was body hugging and it was mid thigh length. I slipped on a pair of 5” open toed stilettos to complete the look. I turned around and Roseanne was just looking at me smiling “ Now that is my little sister, you look amazing” , I looked it the mirror and had to admit I really did, I felt wonderful I really felt like a women.

My sister got dressed, all the while I just sat there thinking about the night ahead. It was time to leave it was after 9 already, Roseanne gave me a black shoulder bag to complete the outfit, I opened it up there was lipstick and perfume inside. I applied the lipstick and turned to Roseanne “How do I look”, she responded by saying just great and snapped a photo of me, next she got a selfie of both of us. Before I knew it she had posted it to her face-book page with the comment “Big night out with my cousin “Olivia”.
Roseanne drove into the city it was almost 10 o’clock by the time we got to the nightclub, we walked straight up to the door and the security guy just smiled “Welcome Ladies come right in”, I could see him looking both of us up and down, I felt his glare, I didn’t feel embarrassed, I felt empowered for once I didn’t care who was staring.

We walked down the stairs into the club, I could see some people turn and stare, I felt sexy, I looked sexy and I was loving it. One of Roseanne’s friend was waving us over, they were seated off to one side. There was 5 girls, Roseanne introduced me as Olivia her cousin from out of state, she said I was visiting for a while and if I liked it I might stay.

I looked at the girls they were all a little older than me probably similar age to Roseanne. They all looked incredibly hot they were all similar height, they were all great looking girls dressed in sexy clothes. One particular girl, Maxine was stunning, I couldn’t take my eyes off her. She had long black hair, luscious full lips with red lipstick and a red dress that was struggling to hold in her big size D boobs. The dress was also short and when she sat down it revealed her magnificent legs. I am sure she saw me looking so intently at her. Roseanne bumped me and whispered in my ear “I thought you might like Maxine but you need to take your eyes off her, the nights still young” I turned my head and looked at some of the other girls, they were asking me questions about myself, the music was loud, the drinks started flowing.

Most of the girls got up and started to go to the dancefloor, they pulled my arm and urged me to join them. I was really getting into this, there were guys everywhere just looking at us, several guys came across and tried to get one of the girls dance with them. They were all turned down. The whole group of us were just dancing together, the music was thumping, I was really getting into it. I noticed guys looking at me but I didn’t care or respond I was having to much fun with the girls.

The dance floor was crowded we were all close to one another we were rubbing up against one another Maxine was next to me, I felt her rub her boobs over my arm, her legs were rubbing against my leg, she pushed in front of me and without missing a beat kissed me on the lips as she dropped her arms around my neck. I kissed back, I was in heaven…………….that was just the beginning.