Hi Susan,

I wanted to tell you my story. When I was about 13, I started putting on my sister’s dresses and skirts when no one was home. This went on for a couple years. I think I did it because I was too shy to even wear shorts outside, and I couldn’t figure out how girls wore the stuff they did and it didn’t bother them. Well, when I was 15 years old everyone went out and I was home alone, and I went and put on one of my sister’s skirts. It was black and was about three inches above my knee. My legs looked so white in contrast to the black. Usually I was always extra careful to put everything back before anyone got home. This time I was so lost in the contemplation of my legs that I lost track of time.

All of a sudden I heard the door opening, and my mom and sister were coming in. I hurried and took off the skirt and put my jeans back on. I barely made it before they walked into the room. What I forgot was the skirt lying there. They didn’t notice at first, but all of a sudden my sister asked what her skirt was doing on the couch. She told mom that she had just hung it up before they left.

My mom asked me if I had taken it out and I denied it. All my mom wanted to know was why I had it out, and she would forget it. Well being a guy I wasn’t going to tell her I wanted to try it on. I still denied it. Mom sent me to my room and said she would decide what to do about this. I never thought she would do what she did.

When she came into my room I thought I would be spanked or made to stay at home for a week. I wish that that was what she had planned. Instead, she brought in one of my sister’s very short skirts. It was 'ra-ra' style, with layers and layers of ruffled eyelet lace. She told me if I wanted to be a girl I was going to dress like one. She made me put on the skirt and I was so embarrassed I was shivering. She looked at me and asked how it felt. She then said get used to it because you will be dressing this way for a long time yet.

My legs were so cold I was shaking. She then made me take off my socks, saying that girls don’t wear socks with skirts. I kept trying to pull the skirt down to hide my legs. I was told not to pull at it again, and that it was meant to be worn short. She then lifted up the skirt and told me girls don’t wear boxers either. She said to go get a pair of panties from my sister. I pleaded not to make do this. She said my sister should get to see me like this, as will many others see me in the future.

She took me into my sister’s room, and my sister looked at me and started laughing. She said I had nice legs, and that she didn’t know she had a sister! She made me put on a pair of her panties - they felt all soft and slippery and they had lace on them. I was made to stay dressed like this the rest of the evening. I was told that if I tried to hide my legs the next skirt I wore would be even shorter. I begged Mom that I learned my lesson, but she said I wasn’t getting off that easy. She said I would be doing this and more till she felt I was going to act like a boy, and not a girl.

Well it got worse every day. The next day I got home from school and Mom was waiting on me. She said go change into a skirt and come into the bathroom. In the bathroom she said girls don’t have hair on their legs, and she shaved my legs and told me it was my responsibility to keep them that way. Again I had to stay in those awful clothes all day. Lucky no one came over, but my sister kept whistling at me and saying she couldn’t wait for her friends to see how sweet and cute I was.

A couple of days later things got even worse. It was a Saturday, and Mom said we were going shopping, and to go upstairs so that my sister could help me get ready. Mom said my sister had all the clothes I would need to wear. I was trembling and feeling hot and cold when I saw what was laid out on her bed. I had to put on a lacy bra, a pair of her soft cotton panties with lace around the legs, and she had a skirt for me that was very short, and a gauzy white blouse.

She said that when I was dressed to let her know. The worst was yet to come, after I put the clothes on she came in and said Mom wanted me to be pretty. I had make-up put on me, and she painted my toenails light pink. I was made to wear a pair of her sandals. I thought I was going to be sick. When she was done I couldn’t believe that I was to be made to go to the mall like this. I was so embarrassed I could have died.

We went, and no one said anything to me. I guess I looked like a girl. I was bought skirts and panties and bras, and Mom also got me some panty hose to wear. When I got home I found out I had to wear girl’s clothing every Friday night for the next six months, and if I did it I could have my own clothes back. Also I had to go out with my sister like this wherever she was going. I did this for the set six months, and I vowed never to wear girl’s clothes again. None of my friends ever found out, but my sister always had the threat that she would tell them if I didn’t behave and do as she told me. So needless to say I learned my lesson the hard way, and despite my vow, girl’s clothes have had a magical fascination for me ever since.

Thanks,

Dan

Spoiler:

Dear Auntie Helga,

Hello my name is Adam. I wanted to talk to you about my many experiences of being dressed as a girl. Over my life I have been dressed as a beautiful girl many times but I will only talk about my first two today. The first happened when I was 13 years old. I was at my friend Jessica's birthday party. Her mom had gone over to her aunt's house at the time. All the other male guests had gone home and it was only me and four girls. We where playing truth or dare when I was dared to dress as a girl and stay like that all night. I accepted thinking they would put me in a dress and that was all.

They took me upstairs into Jessica's room and told me to strip naked. I told them no and they said I could do it or they would help me. I stripped naked and was taken to the bathroom. They shaved all my body hair off and I was in shock at this point. They got some hair dye from her mom's drawer and dyed my hair pure black. Then they added pink and purple highlights making my hair very feminine. They plucked my eyebrows and put bright red fake nails on all my nails. At this point I had given in and let them do what they want. They took me back to her room and got a matching pair of pink bra and panties. The bra was stuffed with tissue paper. Then they went to find an outfit. Jessica was at the time taking ballroom dancing classes and had a lot of very feminine dresses.

They soon picked out a bright red dress was strapless and went all the way to the floor on me. They also grabbed a corset and stockings. They put the corset on very tight to give me a feminine figure and put the stockings and dress on me. They then gave me a full makeup job and curled my hair. If you didn't know any better you would think I was a girl. When her mom came home they told here what happened and she called and told my mom. I was left like that for the rest of the evening until my mom picked me up. As I left they made me promise to let them do this again or they would tell everyone in school.

The second time happened in the middle of June. My parents were going to a town to look at houses because we where about to move to a new town. I really didn't want to go with them and decided to stay with a friend. Sadly all my male friends where away and my only friend left was about to go to Puerto Rico to visit her family. Her mom said I could come and I readily agreed. On the way her parents told me that where would be staying in a different hotel room because her parents would mostly spend time with her grandparents and we would want to explore. Later at the airport we were waiting to board the plane when my friend asked if she could work on my nails. I said yes, being bored out of my mind. She quickly pulled out her makeup bag and started filling my nails. When I thought she was done I started to pull my hand back when she told me she wasn't done. She then pulled out a bottle of pink nail polish. Before I could react she had painted one of my nails and I knew I would have to let her finish.

When she was done with my hand she did my toe nails. On the plane she shaped my eyebrows into a girly style. She also plucked of all my facial hair. When we landed she seemed to be very eager to get to the room. When we got to the hotel she told me to strip naked. I said no and she started to look all sad at me. I couldn't stand seeing anyone cry and said I would and stripped naked. She then took me to the bathroom and waxed all my body hair off. She then had me sit on the toilet and styled my hair, which went down to my shoulders, into a girly hairstyle. I already looked like a girl but the clothes were a final touch.

She pulled out a corset, black lingerie, bra and panties, jean mini skirt, pink tank top, and pink flip flops. After being dressed we went down to the restaurant to eat. During the whole dinner I felt like everyone was watching. After we were done I quickly went back up to the hotel room. She gave me a lingerie pajama set and put my hair in traditional curlers and told me to go to bed. The next day would start my week as a very feminine girl.

Thanks for reading.
Adam