What got you interested in crossdressing ?

My experience is rather different . I started dressing up at the request by my then fiancé . She knew I was bi and wanted to see if she could get me to dress as a woman . Without thinking about it , I agreed . I told her that if I do it I will want my own clothes . Within 2 weeks she ha bought me 3 dresses , bras , panties , shoes , a wig and breast forms . After struggling to get dressed , I really liked how the clothes felt on me and how I looked . That was 25 years ago and I still do it to this day .

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HumanEarth · 51-55, M

I have a similar story and I posted this story on another social media website and the photographs were found on-line

This is my story how I got started wearing ladies lingerie

This was back in the middle 1980s. When all of this started, and I was about 18 years old. I just meet this girl through a mutual friend. Let’s just call her Heather for the sake of the story. Well she is the one that asked me out and very much eager to get to know me better. We went out on a date and hit it off. So we became an item after a few dates.

So while after a while we start with the make-out sessions. We would get to the point of going too far. That is when Heather would stop me and send me home. With some of blueish balls no man wants. Heather would continue this game for quite a while. But it seems that she would let me get a bit farther each time. Then all the suddenly she would stop me again.

I would be so sexually frustrated. Oh! I am leaving something out. Let’s back track for a bit. I forgot to mention, that I was a total virgin at the time. I never even kissed a girl or seen one naked at this time in my life. So you young men out don’t feel ashamed for still being a virgin at 18, because I was there in your shoes.

Well Heather kept this game up every weekend I would say for at least two months. The one-day Heather somewhere between the date of the usual dinner and movie. She said “I have to go back to my house for something, I forgot it.” So we headed back to her house where she lived with her mom.

We get back to the house and Heather quickly disappears and leaves me in the living room with her mom. So while I wait, her mother want to start talking to me. Trying to make small talk. She starts off be saying “ You and Heather been seeing a lot of each other lately. I see.” and “What do you have planed for the rest of the right?” But she said it a different way, kinda like with a shit eating grin. Do you get what I mean?

Well Heather comes back into the room. This time holding this fairly large boxed all gifted wrapped and topped off with a bow and all. Well I played stupid and said “Did you want to drop that off somewhere?” She goes “No silly. This gift is for you.” I had a puzzled look on my face, and I was thinking in my head. It’s not my birthday or some holiday. So I said “For what the reason for this. It’s not my birthday or nothing.” Heather moves her eyes downward and starts to say “I want to take our relationship to the next level and this gift is to mark the occasion. And I want to know if you want to continue and see where this goes before I give you this.”

Well I said “Yeah sure.” (I was more curious what was in the box than anything else) and she handed me the gift box. I was about to open it, and she said “You might want to open this in the other room. My mom is sitting right over there.” I basically said “So what. What in there?” and just start ripping and opening it before she could stop me.

Do you want to know what was in that box? It was packed for a lady's lingerie. From about a 15 – 20 pairs of panties, a yellow baby doll nightie, a green satin teddie, black & hot pink floor length long nightgown, a garter belt and few pairs of stockings. She must have had maxed out her credit card or something. I know lingerie is not cheap. I wished I should have listened to Heather and opened it in the other room.

Here I am holding up and picking though a box of lingerie. That so happened to opened in front of her mom. Man I was so embarrassed. Still, at that moment I was still thinking all this lingerie is for Heather. So I said with my reddest face and trying not to look at her mom. “Heather! You are going to look great in this stuff.” Without no pause she said “Nope! These are not for me, (she pauses and then continues) but these are for you to wear.” To top it off she said it in front of her mom, and I was even more embarrassed than before.

I said “Why for me? I don’t wear this stuff. If you didn’t notice, but I’m a guy.” “You see” Heather said and continue to say “I really like men wearing these things and I got you everything in your size.” I really didn’t know what to say to her. The only thing that came to my mind is “ Are you freaking nuts? I will not wear that stuff!” I told her that.

Well convinced me to wait on it and talk about it later. So we were going to out to movies, But the whole ordeal took longer, and we missed the start time of the movie. We went down to corner to the video rental store and rented movie instead.

So after we get back home and started to watch the movie. Her mom already went to bed, and we had the living room to ourselves. Well it was not before long we were making-out and getting all hot and bothered. Then Heather stops again, but this time she says “It you want this to go farther. You have to wear what I got you.”

Do you remember a little while back, when I said “I don’t wear this stuff. If you didn’t notice, but I’m a guy.” Well guess who wore lingerie that night. Hey before you judge me. Keep in mind I was a virgin, and I was constantly being teased sexually. To the point I was going to explode. So I caved in, dig deal.

Well shorty after we moved into together and Heather slowly replaced mine mens undies with pretty lingerie and panties. So after about two years that all I was wearing, and I loved it every bit of it.

I may not be with Heather no more, but I still wear lingerie till this day. That’s all because of Heather’s influence. Now I have been married 25 years and my wife is just as happy as Heather was with me in lingerie. To top it off I have a lingerie collection that would choke a Victoria's Secret Angel or a Fredrick's Of Hollywood lingerie model.

This has been my story on how I got started wearing lingerie and it got me to wear other ladies clothing.

Mr. Human Earth

Ramon67 · 61-69, M

@HumanEarth thank you for sharing your story .

BonnieWillRingsYourBell · 22-25

When My grandfather’s friends brought me clothes to wear. I was almost 12 yo.

Uniformed · 46-50, M

My experience was similar ..years ago a girlfriend got me to try on one of her big skirts as a laugh and I enjoyed it.. one day I surprised by wearing it with little white socks, and a pair of cute looking women keds copies I bought with a grey t-shirt saying "womens prison inmate".(I like the dressing up as punishment fantasy)We both thought it was funny and a turn on. I' m straight big and clumsy and not a a "sissy" by any means but still think it's fun and I think lots feel the same..