Dressing Up

My friend Jessie had known for a long time that I liked dressing up in women’s clothes when I was alone, but he had never asked to see it before. I felt a little silly parading around my living room in front of him, wearing only a black silk bra and panty set with stockings and heels, but I was also pretty turned on. I had never let anyone else see what I looked like in these clothes, and now Jessie was sitting back, watching my every move and admiring me!

My cock was stiff, poking out against the front of the smooth panties, and I could see the pre-cum dripping from the head making a wet spot. I began dancing for Jessie, but as I moved, the sensation of my cock and balls rubbing against the incredibly soft fabric of my panties only turned me on more. “I have to touch myself,” I said.

“Do it,” Jessie urged. “You look so hot.”

I kept dancing, enjoying the feeling of the beautiful lingerie against my skin, even my legs rubbing together through the stockings was turning me on. I reached down and began to stroke my cock through the panties. I wrapped my hand around the shaft through the material, pumping up and down lightly, feeling my dick throbbed.

Jessie must have been getting as turned on as I was, because as I stroked myself and danced for him, because he undid his button-fly and pulled out his hard dick. It was dark and hard, the tip rounded and circumcised. It looked incredibly tasty. He reached inside his boxers and pulled out his balls, too, resting his entire package on the outside of his jeans as he stroked his dick and watched me.

We jerked off together, his cock in his fist, me rubbing mine through my panties as I showed off for him, turning around so he could see my tight ass. I may like to dress up like a woman, but I work out a lot and have a nice, muscular body. I turned back around and pulled down my panties a little bit so he could see my cockhead poking out above the waistband.

Jessie’s breathing was getting quicker and his hand was flying up and down his prick so fast I knew he was getting ready to come. I matched his strokes with my own and we came together, our cocks spurting cum into the air, jet after jet of hot spunk flying out of our cockheads.

We just looked at each other for a few minutes as our breathing slowed, and then Jessie said, “Come here and suck my cock hard. I want your ass.”

I felt my heart pounding as my old friend told me he wanted to live out one of my oldest fantasies. I walked over to him and got on my knees, my limp dick still sticking out of my panties, and wrapped my lips around his soft cock. I pumped my lips up and down his dick, first taking him all the way in so my stubble rubbed his balls, and then as his cock grew and hardened, just stroking over the head.

When his cock was shiny and wet and hard from my mouth, Jessie told me to go get some lube. I did, greasing up his cock until it was slippery, and then pulling off my panties and lying on the ground. He slid two fingers into my asshole, spreading the lube all around and loosening up the tight hole at the same time.

Jessie knelt between my legs, holding my feet and lifting my hips off the ground slightly as he placed his bulging cockhead at the entrance to my anus and eased inside. I reached down and grabbed my dick. As Jessie fucked my ass, his balls bouncing against me, I jerked myself off.

When I came, I let the jism run down, coating his shaft as he eased it in and out of me. In no time he was thrusting deep into my butt, emptying his balls as his cock pulsed. He pulled out of my ass, letting his cum run out, and bent over, kissing me firmly on the mouth. “You’re a good looking woman,” he said to me, and we both grinned.