Ever since I was a little boy I’ve always loved wearing girl’s clothes. I remember going through my mother’s lingerie drawer and trying on her panties and bras. I loved the way the silky sheer material felt against my body. As I got older I had less opportunities to indulge in my fetish until I got married. When my wife was away or at work I would wear her panties and bras while I masturbated. Luckily she was as tall as I was so the fit was pretty close. I would encourage her to buy plenty of sexy lingerie knowing that I would be wearing them later.

My wife and I eventually divorced and I moved out. It was not easy being on my own again especially being in my 30’s but I was able to rediscover my fetish with the help of internet shopping. I could buy all of the women’s panties and bras I wanted and they would arrive at my door without anyone knowing my kinky little secret. I collected all kinds of sexy panties, garter belts and thigh high stockings. I even started to buy dresses and perfume and would spend my day taking a long hot bath, shaving my legs silky smooth and then trying on my sexy clothes. I grew my hair long, wore makeup and could easily pass for a woman. I ordered a big fat dildo with a suction cup base that I would use to fuck my ass with. I love dressing up as a hot slut, wearing makeup, setting up my dildo and fucking myself silly, all the while pretending that I was a sexy girl getting fucked by a big stud.

I would ride the dildo with my eyes closed whispering, “fuck my ass” to my imaginary lover. I like wearing sexy lingerie under my regular clothes and going out in public. The feeling of the sexy panties and bras under my clothes keeps my cock hard as I go about doing my daily errands and I always have to jerk off when I get home. One day, I was walking through the supermarket and I squatted down to look at something on one of the lower shelves not realizing that the sexy pink panties with the ribbon tie up the back that I was wearing were peaking out of the back of my jeans. I stood and walked down the aisle passing a good looking guy who was smiling at me. I smiled back but thought that maybe he was just kind of a weirdo. The guy turned back and walked up behind me and whispered, “I like your panties.”

I was so busted. I turned to him and said, “Excuse me?”

“It looks like those panties you’re wearing are pretty sexy. Maybe you’d like to show me them.”

My face burned with embarrassment. I tried to look away but couldn’t.

“It’s laundry day. They’re my girlfriends,” I said.

He laughed loudly. “Bullshit.”

“Alright. They’re mine. I like to wear women’s panties. Big deal.”

“Hey it’s cool. I think it’s hot. I’d really like to see what you’re wearing under there.”

I smiled and blushed. “Oh yeah?”

“Yeah, my name’s Rajeev”

“I’m Jeff. Listen I’m not gay or anything, it’s just a little fetish of mine.”

“Uh huh. Sure,” he wasn’t buying it. “Who said anything about being gay? I just want to see what you’re wearing under those clothes.”

I thought about it for a second. Nobody had ever seen me dressed as a girl and the thought of it was really turning me on. “Why don’t you follow me back to my place and I can put on a little fashion show for you,” I said.

“Sounds great.”

Rajeev followed me back to my apartment. I made him a drink and told him to make himself at home while I freshened up. Just to tease him a little bit I stripped down to my bra and panties and I walked into the bathroom. I put on some sexy makeup, topping it all off with bright red lipstick. I put on a pair of white thigh high stockings, a white garter belt and a pair of sexy white bikini panties. I then put on a lacy white bra and slipped a pair of falsies into them to make it look like I have tiny tits. I slipped on a pair of red high heel pumps and a flirty white summery sundress. I checked myself in the mirror and had to admit the transformation was quite remarkable. I looked just like a pretty girl. I took a deep breath before leaving the bathroom.

The look on Rajeev’s face as I entered the living room was priceless. His eyes were practically falling out of his head and his mouth was on the floor.

“Like what you see?” I asked.

“I-I can’t believe it. You look amazing. If I didn’t know it was you I’d say you were an incredibly beautiful woman.”

“Thank you.” I did a little twirl, my sundress lifting up a little exposing my stockings and garter belt.

“Wow,” Rajeev replied. “Do that again.”

I spun around again, bending over a little so he could see my ass. He grabbed his crotch and shifted in his seat a little.

“What’s going on over there?” I asked.

He unzipped his pants and pulled out his cock.