Early crossdressing

I was lucky enough to have 2 older sisters and an ‘open minded‘ mother when growing up. I was the youngest and the only boy.

When I was about 8 or 9 years old my sisters decided to play ‘dress up’ with me one day when we were all home alone. I had no idea what to expect, other than I’d be wearing a dress at some stage.

The girls are 2 and 4 years older than me, and very open with each other and their needs.

I reluctantly agreed to get dressed up by them in underwear and a pretty girlie dress and stockings. I was put into a training bra and silky panties, followed by an open bottom girdle and light tan stockings. This was making me dribble what I now know to be pre-cum as well as getting a little boy erection, which they thought was cute.

Next came a full length slip which felt sensational, and lastly a pretty little pink cotton and lace dress. I loved all the wonderful girl clothes, particularly the silky slip and nylons - wow what wonderful sensations.

My middle sister was teasing me and asking what all the wetness was and why I had a stiff boy thing. I looked and felt wonderful and loved being fussed over like a girl.

My oldest sister said to take off the girdle and dress, lift up the slip, and pull my panties across to expose my little hard dribbling dick. I think she had some experience with boys as she told me to rub it and it would feel good - and she was right!!

I was hard and enjoying the soft silky girl underwear next to my skin. I knew what happened if you touched yourself too much, but I was encouraged to play with my sissy dick more and more while touching the soft panties and bra.

My middle sister was watching quietly as my stroking became more rapid and I began groaning. My oldest sister was laughing at me and saying I need to show them what sissies were good for.

Finally I shot a little boy load on my exposed tummy and the side of the panties. It was the strongest orgasm I had ever had at that time, and shot some distance onto the nylon slip. It felt great for me, but surprised my middle sister as I don’t think she’d ever seen a boy cum. She was told to taste it because she’d be getting lots of it when she started dating boys.

I so love my sisters for sharing their things with me.

I used to go to moms room when she wasn't home and go thru her pantyhose drawer and her slips and put them on.

Been a bit inclined to like female clothes for years without knowing why, ive only just realised it may go back to a next door neighbours daughter whose house i was in when we were children, and she tried to dress me in her petticoat/slip, i didnt let her ,but maybe this is where it stems from.

At age 6 my sister 13 & her friends put me in her little girl party/easter dresses with petticoats and frilly panties. My grandmother loved it....mom not so much. When I was 13 my sister left for college mom got a traveling sales mom and grandmom moved in. She would go thru sisters old clothes and encourage me to wear at home when mom traveled. She bought pastel pink,yellow,blue panties which my mom found in my laundry and my Gmom told her I asked for them ' mom gave me quite the look. One Saturday morning when mom was gone she wet and rolled my long hair sat me at her vanity and put mascara, pink blush, eye shadow and lipstick on my face. Then she gave me a XS high waisted panty girdle with padding in the butt and hips. Pink back zipp Capri's came next with her presenting me my first padded bra. I pulled a thin white scoop neck over my small 32A padded bra paired with pink pumps with 1 inch heels. She brushed my hair out and put me in a mirror , I didn't recognize me , I was very pretty girl , turning around I had the cuties little curves and my bra was obvious thru the top. Gmom told me to wait in the den later she walks in wearing skirt,pantyhose,high heels,full makeup and white satin blouse I could see her bra through. She handed me a small purse and told me to get in the car.I was panicking at the thought of going out in public , she drove to a nice restaurant at the mall. We went in and as we were approaching the reception desk she said we were meeting mom for lunch , just then mom walked up , looked at me and the look on her face I will never forget

Not sure if it counts as real crossdressing, and it was only a couple of times in my early teens: I’d often go over to my best friends house to swim with him and his two sisters. I liked to swim, but the real incentive was the opportunity to hang out close with girls in bathing suits, ogle, and store up fantasies for future JO sessions. They didn’t have a pool house, using a curtained off space in the garage as a changing area instead. This particular time it was just me and my bud in the pool; his mom and the girls were gone for the day. We’re in the garage peeling out of our wet bathing suits when we see his sisters underwear in the basket by the washer. We were just horse playing around being naked when he went over to the basket, took a pair of his oldest sisters panties and slipped then on. We were both skinny so they fit sort of OK, but there was no pouch of course, so the front got really stretched as we instantly got hard. He tossed another pair to me, which I eagerly put on, totally turned on by the naughtiness of what we were doing together, and harder than I’d ever been. We resumed our horseplay, but this time as “girls” sort of, dancing around, swinging our hips provocatively as we could at that age. Pretty soon the pantries got really uncomfortable in front, and we took to adjusting ourselves for some relief. The next thing we knew we we’d taken the panties off and were chasing each other trying to force the other to smell the panties we’d been wearing. There was some self-stroking to get comfortable again. It didn’t take long before the stroking became mutual as we smelled the panties and talked about what it was like to look like a girl; pushing our cocks down and back into our crotches, then squeezing our thighs tightly together, so that part of our bodies looked like girls. My bud said “C’mon” and we went back into the curtained off area of the darkened garage…where my bud kept a jar of Ponds cold crème and some old rags. We jacked off together, the slipperiness of the cold crème making for an incredible sensation. He had Vaseline, too, and we took turns showing each other what it would feel like to be “a girl.” We observed how our boy holes were probably tighter than any girls pussy, an intriguing thought. Afterwards, we tossed the panties back into the laundry basket, washed ourselves at the laundry sink, got dressed and hung out the rest of the afternoon watching TV and reading comics and purloined Playboys until it was time for me to go home. By the time I went away to college, bikini panties and thongs were the most popular girls styles; those were even more fun to put on than that day in the garage with my bud.

@Dixon, I totally thought your fun romp with your bud was gonna end in a different way lol.