Crossdressers?

Question

Did anyone start dressing as a teenager? How did you get started? Did someone help you? Did you enjoy it? Do you still crossdress?

Answer 1

I started around 8. We were at my uncle and aunts house for the weekend and my cousin and I were playing in her room. Her older sister came in and the next thing I knew she had me dressed in panties and a dress. We all enjoyed it and have been doing it ever since.

Answer 2

OK, the short answers are yes, tried some of my sisters clothes, no, yes, and yes.

I would get writer's cramp if I tried to give you the long answers, so we'll settle for something in between.

Crossdressing, for me, is a process, and an ever evolving one at that. It is though, at the end of the day, only crossdressing. I don't have any plans at this time to take it further, although I am open to exploring spending longer times dressed to see what it is like. Crossdressing is something I do, but it does not define me. I have many other interests and I can go for months without dressing. I can then spend weeks on end dressing and playing around with my feminine persona. I would like to think that having reached the ripe old age of 40, I have achieved some balance between crossdressing and the rest of my life. It is not always easy. I get a great deal of personal satisfaction from dressing, but I have also experienced a considerable amount of fear and self loathing. Hopefully, in 20 or 30 years, I will be able to look back on it all with fond memories and think it was all worthwhile and not just a little fun.

Answer 3

I had a friend who's wife started him. She dressed him for some sex play. He liked it so much that he started dressing up just because he liked the feel. So his wife got in contact with a crossdressing organization and they started going to meetings. All the crossdressers at the meetings thought that crossdressing was such a good thing. They encouraged my friend to crossdress more and more. Eventually it lead to his divorce and he had an operation to become a female.. Completing this transsexual journey.. But he's no happier now... and he considering it all an addiction trip.. Lots of pain along the way. So, does crossdressing make you want to go further and further and seek the ultimate high - - does it lead to transsexuals and depression?

Answer 4

yes,ive been dressibg since about 10 years of age.if i remember right,i got my start we i found a large bag of cloths that wre pitched from a house we the girl was evicted. she was a dancer and the outfits were very sexy.i felt a strange desire to try these things on. Ihave prefected my look/style sense then and at times i even go driving while dressedup.ilove the feeling i get so i now have a bigger female wardrobe then male.There is nothing wrong with crossdressing, cloths are just cloths .Its lots of fun too

Answer 5

A lot of crossdressers do. I started in my teens and have carried on ever since. At the beginning I was on my own but once I came out as a CD/TV I found plenty of people who are willing to help.

Answer 6

The earliest memories I have about crossdressing was trying on my mother's nylons when I was about six or seven. I remember my mom caught me and told me to take them off, or she would make me wear them to school. I took them off, but secretly thought it would be great to wear them to school. I was lot more careful after that.

In my teens, I started to wear more than just nylons whenever I could. I got my first real girlfriend when I was about 17, and thought that would take away the desire to dress up, but it didn't. She was close to my size, and I would borrow her clothes (without asking), take them home and wear them whenever my parents were gone. After a week or so, I would sneak them back to her house. She could never understand how she could lose outfits on the floor of her closet and find them a week or two later. I think she had her suspicions, and that may be why she broke up with me.

I continued to dress up every chance I got all through my late teens until now. When I got married when I was 29, I thought I could give it up, but after about six months of marriage, I started dressing in my wife's clothes whenever I could. I bought my own lingerie and hose, but would wear her dresses, skirts, and blouses whenever I was home alone for more than an hour.

A week after we moved into our house (a year and a half after we got married), she found my stash of lingerie, and almost divorced me. After a lot of screaming, crying, and arguing, she finally came to accept me. She still doesn't like it, but she occasionally will go shopping with me and help me pick out new outfits. She doesn't mind if I dress, but I have to do it when she and my daughter are not around. She does let me take a weekend away about once every three months to dress up for a full 48 hours at a time.

Answer 7

Yes i cross dress even right now I am wearing a mesh thong and a silk camisole under my shirt and shorts. Love the freedom it gives me from the BVD's and the fruit a loom for guys. It is very conformable to wear all the time.

Was teased by my sister when I was a teenager she even went out and brought me my first bra and panties set really enjoyed them even though my family was against it.

As for going all female and become transgendered that won't happen to me I like who I am today.

Answer 8

I began to dress feminine when i was about 9 years old,One day i just started doung it and never quit.Yes i loved doing it and still do it,as a matter of fact i am dressed in a skirt and heels right now

Answer 9

i started at 3-4 years old and still do

Answer 10

i began as a teenager, surpressed it , but it returned all in a while.

One year ago I let it go, no resistance at all, and now it has disappeared.

I talked in a grouptherapy about ir, that hepled,but did not solve the problem.
So I am suggesting that letting go may help.