Gay Male / 27
When I was younger--preadolescence--I started wearing pantyhose. I would find a pair of my mom's or sister's that they had discarded and I would wear them to bed at night. When I was 13 and my sister was 16 she confronted me about it, I think she had known for a couple years. I told her I liked the feel and she asked if I would like to try the rest. So one day after school we did.
I went straight home from school and my sister was waiting. She had a lace panty, hose, heels, a lace bra, leather mini, and blouse all laid out for me. She helped me dress, then told me to sit on the bed. She got her makeup out and gave me the works. Once she was done, she sat down beside me and told me--Wow, you make a better girl than most of my friends. Other than my sort hair, I looked like a typical 13 year old girl.
I just stood, awkwardly because of the heels, in front of her full length mirror and stared. I couldn't believe I looked that much like a girl. My sister asked if she got me a wig, if I would be interested in posing for some pictures. I gave her a sheepish smile and said sure. Being dressed that way felt wonderful and if she was going to help me do it again, I would go for her taking a few pictures.
About a month and a half later she had the wig, it was a blonde shoulder length one that looked fairly natural. One of her friends worked at a clothing store and had given my sister her employee discount so it was a fairly nice wig. We got right to it. black lace panty and bra, stocking and garter, one of my sister's knit tube dresses (green), and heels to match. She did my makeup and topped it off with red lipstick and nail polish. It felt so wonderful, and, I thought, I looked even better than before. I heard the doorbell ring, and my sister told me she would be right back. When she arrived back, she had one of her gf with her. I started to panic, but she told me to relax--Sarah was going to take the pictures.
Sarah took the pictures with my sister helping, my sister would help position me while Sarah told her what she was looking for in the shot. Both of them kept joking with me and getting me to smile, so the pictures looked fairly natural. After about an hour, of shooting and positioning me, Sarah said, "OK, now what about some boudoir pics?"
My sister convinced me to take the dress off and I started posing in the lingerie and heels. I have never been hairy and at 13 I had almost no body hair yet, just some very light almost non existent pubic hair. Well, the pictures were taken all the way down to me in just the panty, stockings and garter, and heels. They put them up on the computer for me to see and they were marvelous. I couldn't stop smiling, I just loved how I looked and especially how it made me feel to be made a girl. My sister gave me a thumb drive with the pics on them, and helped me get the nail polish off. That was all that was said about our photo shoot for a couple weeks.
A couple weeks later my sister met me after school and told me, "I want to show you something." We went over to her laptop and she opened it up to a discussion site. She told me, "Look." She had posted my pics and asked what everyone thought. At first I was horrified, but she told me read the comments. I started reading and wow, they were all very nice. My sister had not told anyone that I was a guy, and nobody on the site could tell. All the comments were asking for more or for a date. My sister looked at me and said: "See, I told you that you make a better girl than a lot of my friends do." Then we had a serous talk. I told her I really like being a girl, and always had. She told me that she would help if I wanted her to. The next day I started my training. How to walk in heels and how to apply makeup, nail polish, and how to sound like a girl. After a couple of months I was getting fairly good at it. My sister decided it was time I met the world as a girl, and said she and Sarah would take me to a party if I wanted to go. I really did.
To make a long story shorter... The party was great! I had a couple guys hitting on my most of the night, and one even kissed me. I started going places with my sister and her friends. Only Sarah and my sister knew my secret. By the time I was 16 I only partied as a girl. My sister graduated and I continued with the friends I had met. I never went far enough making out to get found out, I have a little cock and I learned to tape so if anyone tried to grab a quick feel, I was able to slap their hand away before they could feel anything.
After I graduated I came out and started living as a girl. Now only my family and a few close friends know I am not a girl. I have done hormones and herbals and I have a nice set of 40C breasts, so I very much do not need any fake forms. I kept my male clitty and it still works, but does not get as hard any more after the hormones. I date and have fun. I'm the girl with the extra surprise for those that want more than just engaging conversations.
I went straight home from school and my sister was waiting. She had a lace panty, hose, heels, a lace bra, leather mini, and blouse all laid out for me. She helped me dress, then told me to sit on the bed. She got her makeup out and gave me the works. Once she was done, she sat down beside me and told me--Wow, you make a better girl than most of my friends. Other than my sort hair, I looked like a typical 13 year old girl.
I just stood, awkwardly because of the heels, in front of her full length mirror and stared. I couldn't believe I looked that much like a girl. My sister asked if she got me a wig, if I would be interested in posing for some pictures. I gave her a sheepish smile and said sure. Being dressed that way felt wonderful and if she was going to help me do it again, I would go for her taking a few pictures.
About a month and a half later she had the wig, it was a blonde shoulder length one that looked fairly natural. One of her friends worked at a clothing store and had given my sister her employee discount so it was a fairly nice wig. We got right to it. black lace panty and bra, stocking and garter, one of my sister's knit tube dresses (green), and heels to match. She did my makeup and topped it off with red lipstick and nail polish. It felt so wonderful, and, I thought, I looked even better than before. I heard the doorbell ring, and my sister told me she would be right back. When she arrived back, she had one of her gf with her. I started to panic, but she told me to relax--Sarah was going to take the pictures.
Sarah took the pictures with my sister helping, my sister would help position me while Sarah told her what she was looking for in the shot. Both of them kept joking with me and getting me to smile, so the pictures looked fairly natural. After about an hour, of shooting and positioning me, Sarah said, "OK, now what about some boudoir pics?"
My sister convinced me to take the dress off and I started posing in the lingerie and heels. I have never been hairy and at 13 I had almost no body hair yet, just some very light almost non existent pubic hair. Well, the pictures were taken all the way down to me in just the panty, stockings and garter, and heels. They put them up on the computer for me to see and they were marvelous. I couldn't stop smiling, I just loved how I looked and especially how it made me feel to be made a girl. My sister gave me a thumb drive with the pics on them, and helped me get the nail polish off. That was all that was said about our photo shoot for a couple weeks.
A couple weeks later my sister met me after school and told me, "I want to show you something." We went over to her laptop and she opened it up to a discussion site. She told me, "Look." She had posted my pics and asked what everyone thought. At first I was horrified, but she told me read the comments. I started reading and wow, they were all very nice. My sister had not told anyone that I was a guy, and nobody on the site could tell. All the comments were asking for more or for a date. My sister looked at me and said: "See, I told you that you make a better girl than a lot of my friends do." Then we had a serous talk. I told her I really like being a girl, and always had. She told me that she would help if I wanted her to. The next day I started my training. How to walk in heels and how to apply makeup, nail polish, and how to sound like a girl. After a couple of months I was getting fairly good at it. My sister decided it was time I met the world as a girl, and said she and Sarah would take me to a party if I wanted to go. I really did.
To make a long story shorter... The party was great! I had a couple guys hitting on my most of the night, and one even kissed me. I started going places with my sister and her friends. Only Sarah and my sister knew my secret. By the time I was 16 I only partied as a girl. My sister graduated and I continued with the friends I had met. I never went far enough making out to get found out, I have a little cock and I learned to tape so if anyone tried to grab a quick feel, I was able to slap their hand away before they could feel anything.
After I graduated I came out and started living as a girl. Now only my family and a few close friends know I am not a girl. I have done hormones and herbals and I have a nice set of 40C breasts, so I very much do not need any fake forms. I kept my male clitty and it still works, but does not get as hard any more after the hormones. I date and have fun. I'm the girl with the extra surprise for those that want more than just engaging conversations.
