How much have you crossdressed?

My wife thinks she started me on cross dressing, but I never told her my mother started me. I had to wear a pair of my sisters silky panties when our washer died, because I forgot to tell my mom I had no clean underwear. 7 kids in the family, she was headed to work, did one of those open my sisters drawer, grabbed a pair and said put these on. Once I did I was hooked, I jerked off in them after school and kept swiping a pair of my sisters or mothers after that to wear and jerk off in. Once I left home I would wear panties when my girlfriend was at work or away. My wife never knew, she would always pull off her panties before we had sex and throw them at me, I would sniff them, when she got into bed we would sniff together. One night I slid them on and said now go down on me and you can sniff as well. After that she would save her worn panties and make me wear them, then she bought me some negligees and on sex days I would wear them and she loved it. When she was away I would wear some of her satin sun dresses and walk around the house. So I look forward to our sex days because she will tell me to get dressed if she is interested
 
Older sisters bras when a young teen, then progressed onto most of her things, stopped for a while, then started again, work from home a lot these days, love dressing in a secretarial style ( obvs waist down on video calls days!)
 
My first experience was a high school friends Mother's bra and panties. I masturbated quite a bit wearing them. I still like wearing bras, panties, heels, hose, lingerie as often as possible.
No better feeling in the world
 
I would wear my wife’s panties and bra and go to local ABS and suck dick in them, I was wearing her matching pink panties and Bra one time and it turned the guy on so much before I knew it he had me bent over and fucking me with them on and that was the first time I got fucked, you never forget your first time.
 
I would wear my wife’s panties and bra and go to local ABS and suck dick in them, I was wearing her matching pink panties and Bra one time and it turned the guy on so much before I knew it he had me bent over and fucking me with them on and that was the first time I got fucked, you never forget your first time.
I take it that it wasn't the last time
 
I don't call it cross-dressing, It's just how I dress. I haven't worn any male clothing since I retired almost six years ago, and even before that I only dressed male to work and had sexy lingerie under my male suit.
 
Mom had me wearing my older sisters clothes when I was real young and I just progressed from there. I wore her shorts and simple dresses in the summer. Didn't think much about it until I was about 10 and a friend talked me into sucking his cock. Turned me pretty sissy from then on.
 
I think I was 60 when I crossdressed at home for my Madame the first time. I love it now, especially because I know my "pussy" will be filled.
 
Back
Top