Crossdressing memories

[Deborah Jane]

Hi everyone :)

What are your favourite crossdressing memories from when you were younger?

One of my favourites is from when i was about 13.
I was rumaging in the back of my mums closet and i found a white PVC miniskirt and a pair of white PVC knee length boots, which she had last worn during the 60,s. I dug them out and tried them on and loved them straight away. After that, whenever she went out i couldn,t wait to go into her closet and grab "my" favourite skirt and boots and wear them. I often teamed them up with a "skinny rib" jumper, a pair of tights and a white silky bodyshaper she also had.
This was during the "Glam Rock" era [70,s] and at that time i had long mousey blonde hair and loved experimenting with makeup, like the "pop stars" of the period!!

I,m always hoping one day i,ll find a white PVC miniskirt and a pair white PVC knee boots in a charity/goodwill shop, as i,d love to try and recreate that look again :daydreaming:

[TommiTN]

I guess it'd have to be the tingling anticipation I'd get when I knew my parents would be gone and I had an opportunity to dress. Since I'm on my own and have been for many years I rarely get that feeling anymore. I miss it somewhat but I still really enjoy CDing.

[Donna tv]

My very 1st shopping trips created such a "rush" of excitement for me. My parents would sometimes go away for the weekend and I would have the whole house to my self . I remember purchasing Leggs Pantyhose when they came in that egg shaped plastic container. I would get the Q size Taupe get a couple of other non femme items and to the checkout I go. Back then no one ever cared either. My next trip was to Payless for a pair of white strappy 4" heels, I did not try them on just picked them up and right to the register, I think I might have said something like Can she return these if she doesn't like them? Off I went and loved my late night drive arounds. I think I was about 16 at the time

[Karen__Starr]

Mine was when I was around 30, my former sister-in-law daughter left a ton (and I mean a ton) of clothes at our house that she did not want anymore. Everything was size 5 just like me (not anymore, size 7 now) so I snatched up lots of new outfits all in excellent condition. After that I spent hours trying them on, kind of like an early Christmas since they were all great outfits.

[Nicole Erin]

hahaha don't laugh now...

I guess aside when I got serious into this, it would have to have been when I was like 13. I would be up real early in the morning, wear a pair of hose and one of my really long tees that looked more like a LBD than a tee. I would wrap a belt around it and that was my first version of "dressing up".

The only thing that didn't really work with my "LBD" was the fact that it would be a metallica or megadeth shirt. I would ignore that detail and just enjoy.

[Rikidee]

One of my fondest memories was when our church collected clothes for charity. I was about 14 years old at the time. The church had a recreation area with pingpong tables in the back and the clothes were stored in the closet. My brother and I went over to play pingpong and I found the clothes in the closet. Some of the clothes were from girls that I went to school with and I recognized them from seeing the girls wear them. I got my brother to dare me to wear some of them (we are so sneaky aren't we). So I would go into the closet and put on an outfit and prance around and even go outside and run around the building. I will never forget the tingly feeling I got trying on those clothes.

[muggsybear]

I'd have to say..."Exploring" followed closely by "Borrowing".
Too numerous to list all but I had a ton of wonderful opportunities to check out the lingerie drawers of quite a few women and girls.
After the excitement of my mom's, sister's and sister-in-laws' stuff wore off, I discovered the neighbors, aunt's, cousins' and friends stuff. I also had a friend who had finally confided in me that he liked to wear panties and a girdle when he got off. We were at that age when jerking off was the norm so I feigned a little amazement and called his bluff. He dropped his jeans and showed off one of his moms girdles. I kind of nonchallantly dismissed it and we moved on to other things. Shortly thereafter he invited me to sleep over and asked me if I could bring some undies along. I still hadn't told him I was doing the exact same things at home so I told him I'd try. When I showed up later that day he was so excited he came while he was putting on one of my mom's girdles and some pantyhose. Later that night he finally convinced me to try on some stuff and he was amazed that I actually knew how to put on pantyhose.

[Cathytg]

At the long passed and tender age of 24 I discovered pantyhose. Oh, my goodness! Who said Heaven is denied to the living?

[Melanie R]

My favorite crossdressing memory is when I was 17 and several times dressed up completely in my girl friend's clothing when her parents were out of town and she was home alone. She wore a size 12 dress that fit me perfectly as well as her size 8 heels. We did go to a drive in movie with both of us dressed to the hilt. The rest is up to your imagination. Now if I could only wear a size 12 again.

[katrinacd]

Having a girlfriend in high school that allowed me to dress in her, her sister's and her mother's clothes when we were alone at their house. I was really having a hard time dealing with my CDing at the time, and having someone like her in my life was a godsend. I still catch myself thinking about her from time to time and how well she treated me.

[Erin Campbell]

I still consider myself young, so hopefully I have a few "favorite" memories ahead of me. However, my favorite memory so far is probably when I went and got fitted for my first real wig. At that point, my look had gone from guy in dress with cheap wig to passable with a little work. It was a BIG step for me and one that I look back at now and am so thankful I took it.

[Joy Carter]

I was thirteen and one of my sisters dresses fit me perfectly. That was the first time, I felt really good about my dressing. No wig though. I wish I could have gone out and be myself. I was fifty seven before that happened.

[CD Susan]

I have been crossdressing for about 50 years so I have so many memories of doing this. One particular day does bring back memories though. It was about 25 years ago and I was married at the time. I had the house to myself that day and was dressed up in a cheerleader dress that I had at the time. I was in the basement rec room and had the stereo really cranked to some rock and roll music. I was dancing while watching myself in the mirror. The strange part of this is I have always hated dancing. For some reason I liked it that day and really enjoyed the music and watching myself in the mirror. That cheerleader dress was lost in a purge years later. What a shame that is as I think I could still fit into it. Maybe if I still had it I would want to dance if I was wearing it. LOL

[Desiree2bababe]

One of my first memories was riding my bike in nothing more than my sisters slip at night. Caused my first orgasm. Another was donning her body suit sweater with water balloon boobs and riding my bike around, stopping at a house and asking for directions. I was so bold........

[tammie]

Hi Everyone: Well lets see, I guess the most vivid is the afternoon in Nov in Tenn. when I first tried on a bra.

It was my older sister's brassiere discarded carelessly on her hardwood bedroom floor.

It was a black lacecup underwire Vassarette 36B. I put my arms thru the straps grasped the ends of the band leaned forward (like I had seen my mother do so many times).

It fit me like I had been measured for it, when I got my little boy breasts into those cups, it was like an electric shock.

I almost feinted from the sensation of my breasts being held up and the feel of the lace against my to large nipples.

I was changed in that instant forever into a CD.

Being caught 2 weeks later by my mother, in her bra slip pantygirdle and stockings was another milestone.

The last really memorable experience was when a few yrs ago I realized its OK for me to be a CD,and I am at peace with being me.