First clothes worn from opposite gender

[trekkyfrom21st]

The first time I put on Female clothes was a one-piece swimsuit when I was 12 or 13 and home alone. I wore it for less than an hour and I loved the feeling of it. I now regularly wear bikini undies and just ordered my first few bras.

 

[LuvMyDiapers]

You're right, I was going to say panties, and then I read the rules! lol ...

That makes it hard for me to pin down, but I could say an influential early experience from wearing girl's clothes was the first time I tried a one-piece bathing suit. It was awesome. I was about 14, and I was using my friends bathroom, which also had a section they used for laundry. I had already been wearing panties since I was 11, and my curiosity led me to peek in the laundry area. I saw his cute older sister's green and white bathing suit hanging in the laundry area. Since the bathroom was locked, I felt safe enough to undress and then slid the bathing suit on. It was so hard to keep my hands off myself wearing one, they are so soft and sexy to touch. I wish I could've worn it out of there.

This was 1984, and tolerance of gay or cross dressing behavior was not very well tolerated, and in school it was essentially social suicide among your peers. By this point I had already been riding my bicycle up to the local mall and buying panties whenever I had money, but I was always petrified browsing for clothes thinking I would run into a girl from school. Still, my next trip resulted in me buying a bathing suit of my own! The reason I think it was influential is that it lead to explore lots of body outfits. The 80s had a lot of lingerie options, and within a couple months of buying that swimsuit I ended up buying a corset, similar to the one in the linked below. This lead to another fun thing to wear back then, the aerobics workout gear. Talk about tight body suits that felt amazing!

First corset (looked similar to my memory)
https://s-media-cache-ak0.pinimg.com/736x/b5/aa/50/b5aa50f74c6ccef1473989e6ca11f4de.jpg

80's aerobics class!
https://img0.etsystatic.com/039/1/5444446/il_570xN.626127948_nh2u.jpg
https://s3-ap-southeast-2.amazonaws...ploads/2015/06/03100958/aerobics2-640x320.jpg

 

[Angelapinks]

You're right, I was going to say panties, and then I read the rules! lol ...

That makes it hard for me to pin down, but I could say an influential early experience from wearing girl's clothes was the first time I tried a one-piece bathing suit. It was awesome. I was about 14, and I was using my friends bathroom, which also had a section they used for laundry. I had already been wearing panties since I was 11, and my curiosity led me to peek in the laundry area. I saw his cute older sister's green and white bathing suit hanging in the laundry area. Since the bathroom was locked, I felt safe enough to undress and then slid the bathing suit on. It was so hard to keep my hands off myself wearing one, they are so soft and sexy to touch. I wish I could've worn it out of there.

This was 1984, and tolerance of gay or cross dressing behavior was not very well tolerated, and in school it was essentially social suicide among your peers. By this point I had already been riding my bicycle up to the local mall and buying panties whenever I had money, but I was always petrified browsing for clothes thinking I would run into a girl from school. Still, my next trip resulted in me buying a bathing suit of my own! The reason I think it was influential is that it lead to explore lots of body outfits. The 80s had a lot of lingerie options, and within a couple months of buying that swimsuit I ended up buying a corset, similar to the one in the linked below. This lead to another fun thing to wear back then, the aerobics workout gear. Talk about tight body suits that felt amazing!

First corset (looked similar to my memory)
https://s-media-cache-ak0.pinimg.com/736x/b5/aa/50/b5aa50f74c6ccef1473989e6ca11f4de.jpg

80's aerobics class!
https://img0.etsystatic.com/039/1/5444446/il_570xN.626127948_nh2u.jpg
https://s3-ap-southeast-2.amazonaws...ploads/2015/06/03100958/aerobics2-640x320.jpg

I remember trying on my first girls bathing suit in in the mid 60's, it belonged to a girl next door and was a two piece nylon one and I was in love. I remember sneaking into their back yard when I saw it on the clothes line one night and I grabbed it and some white nylon panties and dashed across the drive into our basement door. The house was quiet as my parents were out and I quickly tried on the panties and found they were a little tight. When I took them off I checked the size and found they belonged to the second youngest girl who I had a bit of a crush on so I was happy about that and then found the bathing suit was the same size. I was torn whether to keep them or not but decided that they could not afford for me to do that as there were four girls and a single mom who worked with my mom. I am not sure how long I waited but I did go and buy my own bathing suit and some panties not long after that.