A Crossdresser Gets Fitted

Not long ago I was out shopping and stopped at one of the clothing outlet stores that I frequent when looking for sexy clothes and shoes to wear when I go out clubbing or to wear in my adult videos. I was looking through the display rack of my favorite brand of pantyhose, trying to find the colors I wanted in my size, when I noticed a cute guy checking me out. He was about 30, slim and kind of feminine and holding some items of clothing he had picked off of one of the racks. I noticed right away that he was holding women’s clothes.

As I continued to sort through the bins of pantyhose which were all disorganized from the hundreds of women who rummage through them every day, I pretended not to notice my new admirer. It was a Friday night, about a quarter to nine, which meant I was dressed to go to one of my favorite clubs after I picked up a few pairs of pantyhose and some makeup. I was wearing another of my very short hemmed, skin tight bodysuits, with a sheer black nylon top and sheer to waist, tight, silky black hose and my 5 ½” black patent leather stiletto heel pumps.

I made sure to bend over as sexily as possible when looking through the bottom bins so that my firm round ass filled out the tight, black nylon/spandex of my bodysuit and the hem came right to the edge of the cotton crotch of my hose. I continued to pretend not to notice the cute cross dresser as I seductively bent over straight legged, crossing my ankles and absent mindedly stroked the back of one silky calf as I picked up a pair of suntan hose with the other hand.

I was pretty sure that my new friend knew I was not a genetic female, since CD’s can usually spot each other pretty easily, knowing what to look for. I stood straight up and turned around, smiling at the cute guy with the miniskirt, blouse and high heels in his hands, pretending to have just noticed him standing there. I took the couple pairs of pantyhose I was going to purchase and walked over to where he was pretending to sift through the clearance racks. He was about 5’8” 130 lbs, clean shaven, very smooth and femme looking and dressed in loose fit jeans and a t-shirt.

He nervously returned my smile as I approached him and asked, “Are you going to try those on?”

“I wasn’t,” he said, blushing a little and looking down at his selection.

“You should definitely try them on,” I said with a wink, taking the clothes from him, “you don’t want to get home and find out they don’t fit properly.”

I tugged on his t-shirt sleeve and said, “Come on,” as I lead him to the fitting rooms.

“I’m Vennessa,” I told him as we weaved through the racks in the nearly deserted store heading to the fitting rooms.

“I’m Mike,” he said shyly.

“Nice to meet you Mike,” I said turning and smiling a him as we arrived.

“I could use some help getting into these things,” Mike said winking at me, seeming to overcome his initial shyness at being caught buying girl’s clothes.

“Ok,” I said with a sultry grin and led him into the fitting rooms.

I found a large room at the back, and we went inside and closed the door. The fitting rooms in this store offer better privacy than most because they are large, heavy wooden doors that go all the way to the floor and can be locked from the inside. Not like the usual saloon doors that most places have. They also have large full-length mirrors inside.

I closed and locked the door behind us then told mike to strip. I was pleased to see that he was wearing taupe pantyhose under his jeans and was completely smooth and hairless all over. His toenails were painted a dark red and his stiffening cock was nice and thick, about 7 inches long. I rubbed it with my hand through the sheer nylon and it got even harder, beginning to throb. Mike let a little gasp as I squeezed and stroked it.

“Here,” I told him, holding out the little plaid miniskirt and the white silk blouse, “put these on.”

Mike did as he was told, putting the silk blouse on first then stepping into the miniskirt and pulling it up to his narrow little waist. I turned him around and zipped up the back of the skirt, giving his firm little ass a squeeze. Then, I handed him the 5 inch strap sandal heels he had picked out and watched as he slid his femme little, nylon-clad feet into them and buckled the straps around his ankles.

“What do you think?” Mike asked as he admired himself in the mirror.

I stood behind him, looking at our reflection in the mirror over his shoulder. “Not bad at all,” I purred in hi ear as I slid a hand up under the miniskirt and stroked his hard cock through his pantyhose, “now all you need is some makeup and a wig and you are ready to go out.”

“Mmmmmm,” he agreed.

Mike then reached around behind himself with both hands grabbing my tight ass, pulling me against his own firm little but as I continued to jack him off through the tight, silky nylon. He moaned as he ground his ass against me.

I nibbled and licked at his ear and his neck then whispered, “I want to fuck that tight little ass!”

“Mmmmmm, sure!” he eagerly agreed.

I reached up to the waistband of his hose and pulled them down just below the cheeks of his smooth, firm ass, letting hi hard cock swing free of its nylon prison. Mike slid a hand between my thighs and stroked my hardening cock where it was tucked tightly away. I then pulled my own pantyhose down enough to reveal my big hard cock and heavy balls. Mike jerked it slowly for a few seconds then turned around and dropped to his knees.

I let out a little moan as his hot mouth engulfed my stiff rod. He jerked it into his mouth with one hand while he stroked himself with the other. I watched in the mirror as my new little sissy slut in her school girl skirt, white silk blouse, pantyhose and heels sucked my 7 inch cock, deep throating it all the way to my cum filled balls.

I needed release and I wanted to be balls deep in that tight little sissy ass so I pulled out of “Michelle’s” eager mouth and gently pulled her to her feet, guiding her to the little bench near the mirror. I turned her around by the shoulders and pushed her down onto her hands and knees on the bench. Then I grabbed both of her as cheeks, spreading them wide and rubbing the head of my throbbing cock against her puckered little asshole,

“Mmmmmmm,” Michelle moaned as I pushed my cock head against her hole.

I dribbled some saliva into the crack of her ass for lubrication then pushed the head of my cock into her ass with my hand. It was tight and hot and hard to get my cock into, but in a second the head popped in through her clenched ring and she let out a moan.

I grabbed her hips and pushed, sliding smoothly up her chute until my balls rested against hers. I moaned with ecstasy as my whole cock was engulfed with hot, tight, twitching ass! I pumped my cock, slowly at first, letting her ass adjust to it then began to urgently fuck her. I was incredibly horny by now and just need to get off hard and fast.

Michelle furiously jacked her cock as I pumped her tight little ass, balls slapping together. Her ass was so tight and hot it didn’t take long for me to near climax. Michelle was moaning now, too, her orgasm fast approaching.

“Mmmm! Fuck my ass! Oh, baby! Cum in it! Cum in my ass!” she gasped as I pumped harder and faster.

I felt the hot surge as my balls tightened up and a huge load of hot cum erupted from my pulsating cock. I moaned deeply as I pumped load after load of hot juice deep inside Michelle’s tight ass.

Michelle let out a groan as I filled her ass with my white hot cum and shot her own sticky load all over the mirror and down the front of her pantyhose clad thighs. I lurched and jolted as I pumped the last of my load deep in her ass then let my hard, wet cock slip out of her reddened hole.

Michelle turned around and eagerly sucked the remaining cum from my dick. We rested for a moment as the swelling of our cocks went down, then Michelle returned to being Michael and we headed back out into the store.

“That was fantastic,” he whispered to me with a sly grin as we headed to the checkout.

“Very yummy!” I said.

We paid for our items then exchanged numbers in the parking lot before Mike headed home. I on the other hand headed to my favorite club and even more erotic adventures.