I was a sissy before I knew what a sissy was

Looking back I guess it was my first gay experience, but at the time I didn’t even think of it as sex, much less gay. I was only 11.

My neighbor 2 doors down was one of my close friends growing up. He was a few years older than me. We hung out all the time. His name was Jim. One day his parents were out and he called him me to come over. His sister was quite a bit older and was off to college. He said, let’s go through Nancy’s stuff. He had dirty magazines and stuff and we had looked at those before. But, never gone into his sister’s stuff.
It sounded fun, so we started looking in her closet and drawers. The underwear drawer was especially enticing to two young boys. She had bras and panties, and slips and girdles. This was the 60s, so different styles.
We were holding up the bras to our chests and wiggling around in front of the full length mirror. Basically being goofy boys. I liked how silky and soft the stuff was and was rubbing it on my face.
Jim said if I liked the way it felt, i should put it on.
It sounded good, so I took off my shirt and put the bra on. It was too big, but it hung there. I was looking at myself in the mirror and saying stupid things like, ooh, look at your sister’s big boobies Jim.
He said, put on the panties and slip too.
I hesitated, and he urged, come on. Take off your clothes and put on her underwear. So, I did.
I loved the silky underwear on my skin. My little dick got hard as i rubbed it through the panties. Now I was in panties, a silk slip, and a bra; nothing else.
He looked at me and said, you need a wig. She had one on her make up table. I sat down there and put it on my head. It took a little maneuvering to get it strait.
That looks good Jim said. Now some make up.
I wasn’t thinking sexual at all. I was just having fun goofing off. But, i put on eye shadow, rouge, and lipstick.
I stood up and stood in front of Jim.
Do I look like a girl?
Yeah, you do.
Then kiss me you big handsome man, I joked.
He pulled me to him and kissed me. I was shocked. I didn’t think he would really want to kiss me. I was just playing. But when his lips met mine, i liked it. He looked at me. I said, can we do that again?
He kissed me again this time more passionately. I was kissing him back. My mind was flooded. I’m kissing a boy. I’m gay, i like it, I’m gay, we shouldn’t do this, i like this.

He pushed me onto the bed, took off all his clothes, and climbed on top of me. He was caressing my body as he kissed me. He kissed my lips, face, neck. It felt amazing.
He was dry humping me as we made out. I coukd feel his cock, much bigger than mine, pushing against my body.
Then he came. Sperm all over me and the slip and panties and the bed.
He panicked and said, I’ve got to get this cleaned up. I still wanted to have him kissing me, but he said, hurry, get out of that stuf so I can wash it. I changed clothes and he sent me home.
I walked in my house and mom was on the couch watching tv.
What have you been doing?
Nothing, just playing with Jim.
I went in my room. A little while later I went out to get a drink. Mom said, you better wash up before your dad gets home. I thought, that’s weird she never says that. I went in the bathroom and looked in the mirror. I had forgotten my makeup. I was so embarrassed. I washed up. My mom never told dad, and never brought it up again.

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