He Was  A Little Sissy

A friend of min was having a girls night and it was a lot of fun. More than I expected, actually. I arrived and a few of our friends were there, but one of them had brought along her brother. And I burst out laughing as soon as I walked in the door. I’d never met this guy before, but he was walking around in heels and a slip and had curlers in his hair. I asked what was going on and she introduced him as her brother the sissy. She said he’d come to visit for the weekend. And then she got this invite for girls night and she knew she just had to bring him along.

We All Had Fun Dressing Him Up

He was very slightly built and finely featured, he truly could have passed for a woman. Especially when all made up like they were doing to him. He sat back down and we all stated to put makeup on him and experiment. He was happy as a clam to let us do his hair and nails and makeup. She said she’d caught him many times when they lived together at home trying her things on and using her makeup. She would lord it over his head and threaten to tell their parents if he didn’t do as she said. He was pretty weak willed so he always went along when she threatened to tell the parents he was really a sissy.

He Was The Perfect Sissy

And He sat there and chatted away with us drinking apple martini’s and Cosmopolitan’s and talking about girly stuff,

he fit right in! I asked if he’d ever had a girlfriend and he blushed and giggled. He sister said he’d likely wanted a boyfriend, lol. It was hilarious. He got around in high heels better than I did. He said he had a good sized wardrobe at home, but he was too shy to actually wear it out in public, so he kept his sissy secrets to himself at home.

I asked him if he’d ever sucked cock before and he blushed and said no but he wanted to. One of my friends called a bi friend of hers and asked him if he was game to come over and get his dick sucked by a sissy. He said sure, he’d be right over. Within ten minutes, this guy was at the door and we were all egging the sissy on to suck this guy’s dick. He was a bit shy, but with us all encouraging him, including his sister, he gave his first blow job to the friend and he giggled when he got his first mouthful of cum.

This Would Be His First Blow Jobdana dresses up a sissy

To celebrate the sissy’s first giving of a blow job, we all ordered a pizza. Our little group had a fun little party and we had some wine with the pizza. We ended up doing pedicures on the lot of us, and the sissy had fire engine red painted on his toenails. He usually had them painted anyway, so he helped us paint ours as well. I never dreamed when I was invited for a girls night it would turn into the coming out of a sissy giving his first blow job. Strange things can happen with a room full of tipsy girls.

Sexy LiL Dana

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