How did you started crossdressing?

Crossdressing as a part of or type of selfbondage.
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Lillan
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Joined: 18 May 2018, 19:23

How did you started crossdressing?

Post by Lillan »

Hi there,

This is probably already asked in the past, but how did you start crossdressing?
Generally it must have begun as a child, but I was not interested at all when I was young.
However, I was interested in bondage. And all started with the bondage.
I´m now 27 yrs old guy.
I had been a slave to my mother-of-law´s sister for a couple of years. Yes, this may sound a little weird, but we kept it secret and nobody knows about us two.
Today, I live alone, so it's easy.
Anyway, just over a year ago my mistress told me to put on the bras and dress and women's shoes. This was really embarrassing to me, but I did as he told me.
I did not feel very comfortable, but on the other hand, I like being humiliated.
Later, I had to keep more women's outfits and the shoe's height increased.
One day around half a year ago, my mistress tied me to the chair. She then started making me makeup. Finally she put me a wig and after that I got a perfect woman outfit. And after that she let me to look at myself in the mirror and I did not believe my eyes. I looked like a very young woman.
Today, I have already walked out in full makeup and outfits with her at parks and suburban areas.
I also started to like women's clothes, so I guess I have become a crossdresser.
I also got more outfits and now I can wear for example a little girl´s or a French maid´s outfit.
Jess
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Joined: 22 Jun 2019, 21:43

Re: How did you started crossdressing?

Post by Jess »

I grew up using a small town school in Nebraska.
When moving up to the ninth grade in this school it was normal for all boys to dress a girls for the day.
Soon after the start of the new school year in September us freshmen ninth grade students were ushered into the upper classmen's home room.
On the blackboard was written what we were to wear that next Monday.
A hoop dress at knee length to be made out of a thick wire sewed into the hem to be three feet in diameter.
A garter belt with stockings hooked to it.
And of course real girl panties.
Three inch or higher heels.
A purse with lipstick and eye shadow with other makeup.

The freshmen girls were to wear long underwear.
They were allowed to wear their girl shorts and bras under them.

I had been for years trying on my moms old stuff upstairs.
So this excited me to no end but it was the first time I had ever gone out dressed.
Needless to say the short hoop skirts were a real pain to keep from showing our panties.
Soon found out sitting down was a whole new lesson.

I still think back to that time and wish.
I still dress.
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bounddosster
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Joined: 30 Jan 2014, 23:23
Location: England. East of Midlands.

Re: How did you started crossdressing?

Post by bounddosster »

I'm not sure if I could claim to be a cross-dresser, I dabbled a bit here and there with cross-dressing games, mostly on an enforced cross-dress basis. The first time I cross-dressed to of any sorts was when I was seventeen and my girlfriend had tied me up and she removes her tie side black silky knickers and put them on me. I was very embarrassed but also aroused, she had me lick her to a few orgasms before going off to phone her friends while I was left tied up. then she made a meal and came and released me put insisted I worn her knickers and nothing else while we eat, this took place in her parents front dining room and I was scared someone would call around and see me sat there in her knickers. After the meal I was sent to wash the pots while she watched TV then we went up to her room and she finally removed the knickers.

When I got home the following day I found her knickers in my pocket with a note saying "wear these tonight", That night we were to go to the cinema and as I sat there in the seat after the lights went down my girlfriend reached across and popped the button of my jeans undone then pulled down the zip and slide her had inside my jeans. "just checking" she said " oh, you are a good boy". She kept rubbing my cock through the knickers and I was getting desperate not to cum, she sensed this and rubbed harder, then I orgasmed into the knickers put only just in time for the lights coming up for the interval. As I hurried to do my jeans up I could my cum being squashed into my body. My girlfriend looked at me and smiled.

From then on wearing her knickers was a regular thing until she bought me a pair for my birthday a few weeks later.
That's my excuse and I'm sticking to it.
CD Tammy
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Joined: 22 Sep 2010, 23:42

Re: How did you started crossdressing?

Post by CD Tammy »

I was 4. My step-monster used my closet for her overflow. She was one of those socialites that never wore pants. On a Sunday, she had to do a quick change after church to get ready for some social event. On the floor she left a pair of LLegs pantyhose, suntan, size B. I don’t know why I put them on, but I did. I could pull the waistband way up. It was sort of like a bodystocking. That was the start.
Karka
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Joined: 19 Aug 2019, 12:48
Location: Poland

Re: How did you started crossdressing?

Post by Karka »

Hi. I'm new here

I started wearing woman clothers, when I got my own room in work, away from other workers. I always liked shirts and dress, that have buttons on the back. I went to second hand shop, and bought shirt, skirt and hills. Next there was pants, bra nad stockings. I feel excited when I'm dressed like that :) I got two pairs of handcufs, for hands and legs, butplug and ballgag. I tied myself 2-3 times a day, and lowe to cum, when i'm tied :)
Maid_Lauren
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Joined: 06 Feb 2012, 16:56

Re: How did you started crossdressing?

Post by Maid_Lauren »

I'm older and than dirt. As a child in the middle of last century, I would fantasize being dressed as a girl and would wear my mother's panties when I was alone in the house. I also had a bondage and diaper fetish which I couldn't explore until I was an adult.

You children don't know how great you have it. All the info on your favorite kink at your fingertips.
TicleMeEndless
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Joined: 20 Nov 2018, 17:53

Re: How did you started crossdressing?

Post by TicleMeEndless »

That was at i was a kid. Sweet summer, early morning. My mom's swim pants and bra was drying on rope in the courtyard. I was want some hot and scary. I stealed that swimsuit, weared it, took rope and scarf. With all of that i walk to the street. Before that i coiled rope into rings. I checked length: if i help to my hands with corner of something, i can wear and get off the rope from my hands, but i can't do this without something. So, i walk to the street (early morning, sun is raising) and stand close to the fence. I blindfold myself with scarf, wear up rope to hands behind my back (fence helps). Then i took a few steps from fence and spins! After that i realize: I trapped. City is waking up, every seconds something can spot me. I standing at center of street, dressed as girl, blind and i don't know where something what can helps me release my hands. Heart pounding furiously, I blush like never before in my life. :oops: I don't know what to do, and i realize what i don't know if someone looking at me. I went at random forward. I was lucky twice: firstly, I quickly stumbled upon a lamppost that helped to remove the rope, and secondly, after all no one spotted me, or shame could not have been avoided: everyone knew me on this street. Since then, I have loved the sensation of women's clothing on my body, the fear of being exposed, playing with ropes and of course the blindfold.
Not all dreams must come true. Choice with a cold mind. Be careful. Not crazy as me.
PJ67
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Joined: 25 Oct 2019, 16:12
Location: UK

Re: How did you started crossdressing?

Post by PJ67 »

I started to cross-dress back in the late 1950s when I was about 6 or 7 years old, my older sisters stored their bridesmaids dresses in my room and when I could I would wear them, and they felt so right. Like many here, I did not start dressing properly until I got my first bedsit when I would buy underwear as well as dresses, but as there was no internet back then, I had to use catalogues to order things. So much better now-a-days with the internet and so many stores. But for me, it was never so much a sexual thing more that it just felt "right". As I am now soooo old and have put on weight, I don't "dress" as much as I would like too. :cry:
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