I’d seen May around on the normal websites for pervs. She was easy enough to spot. Asian. Mid-twenties. Long black hair. Almost always featuring pics in a royal blue corset, stockings, and black heels. Sometimes there were videos. Usually playing with toys are doing a sexy little dance. She never showed her cock or her face. There was never a partner.
The blurbs were typically the same. Along the lines of living with a girlfriend and could only dress up on certain days. May liked pic requests and had links to an Amazon wish list filled with cheap stripper lingerie. Occassionally it looked like someone would buy something and she’d model it in a little video of photos online.
It was probably a year after I’d first noticed her when May started asking for more. There were posts made seeking a sugar daddy. A strangely specific offer to model for a Lexus Certified Mechanic. Maybe she had car repairs she couldn’t afford. Or just didn’t want to pay for.
That’s the first time I sent a message. I told May that I was a very experienced, dominant man and we could have a lot of fun together. I got a couple of responses and a request for pics. May seemed interested. And then she disappeared.
A few months later she was back posting personal ads. Once again we started to correspond. She admitted she’d never been with a man before, but it was a constant fantasy. So far she’d only gone as far as giving head several years earlier. She was intimidated by me because she knew I wanted more. I promised I’d be content with good head and I’d spoil her like a princess if she acted like a good girl. We went back and forth a bit. Then she disappeard again.
The saying promised the third time is the charm. With May it actually took five attempts over the course of a year. We’d write. She’d get interested. Then she’d disappear for several weeks. The interval after the fourth time I’d reached out was the longest. When she finally showed up again, I knew she was serious. And that’s when I asserted control.
There was a lot of dancing back and forth about when and where. May suggested that I get a hotel room and I was fine with that–as long as she came dressed to thrill. She didn’t like the idea of potentially being seen in the lobby. Maybe even by someone she knew.
I offered my place with the same instruction.
“Nobody has to see you except people in other cars,” I said. “You’ll leave your place and pull right into my garage.”
Again she protested. It appeared the only solution as a daytime hookup when her girlfriend is away.
“I’ll expect you to great me fully dressed. And makeup. Lipstick at the very least. Hair styled.”
“I only have lingerie,” she texted.
“Then get something else. Or use your girlfriend’s clothes. And I don’t want to see that blue corset that’s in all your pics. Let me down and I’ll leave. Go fuck a real girl instead.”
“Yes sir,” she responded.
“And don’t half ass it. There’s nothing more disappointing then a sissy who only wears yoga pants. Skirt or dress.”
“I don’t believe you’ll leave if you see me in sexy lingerie and nothing else,” she wrote.
“Try it and find out.”
May worked from home on Tuesdays. She sent a text with her address as soon as her woman left. She told me to come by on my lunch break for some head.
I showed up in jeans and a button down. I knocked on door to her downtown condo and waited. A few minutes past and I was certain she was backing out. Then finally the door opened just a crack. I saw someone move away quickly. She meekly called for me to come in.
She was taller than I expected–almost 5’10” in her heels. Slender. Sexy. Her face was feminine. Her long black hair was parted in the middle and down. She wore black heels and black stockings. Red lipstick. A thin white blouse and flirty polka dot skirt. I could see her black and blue lace bra through her silky top.
“Do you like my outfit?” she asked bashfully.
“Show me what’s under your skirt.”
May lifted the skirt to reveal a blue satin garter belt with black lace trim and tiny matching panties that were barely holding in her hard cock.
“I approve.”
She smiled and dropped her skirt.
“When is the last time you’ve done something like this?”
“I’ve met with two guys. Just wearing lingerie under my normal clothes. And I sucked them both off. That was in the last year. Before that it was back in college.”
“Then are you any good?”
“Very good.”
“Does it make you hard?”
“Very hard.”
“What do you do about that?”
“I jack off later.”
“And you never fuck?”
She shook her head.
“I want that virgin ass. I’ve seen your videos. Watched you ride those toys. It’s time you try the real thing.”
“I don’t know,” she said.
I stepped forward and took her hands in mine. I could tell it was the first time a man had ever been aggresive and treated her like a woman. I lifted her chin and kissed her. I took her hand and led it to my crotch. My cock was already hard.
I pushed her skirt up and rubbed her through her panties. She stepped back quickly.
“Men don’t normally do…”
“I’m not normal men,” I interruped. “I’m not some nervous guy sneaking out for head. I’m experience. I’m good. I know what I want and I’m not afraid to enjoy it.”
She stepped back toward me and I pulled her close. We kissed again. I pushed my hand back beneath her skirt and rubbed her cock.
“Show me your bedroom.”
“We can stay here…”
“Show me your bedroom,” I repeated. “You’re going to suck my cock in the room you share with her.”
She started walking down a short hall and I followed. There was a full length mirror in the corner. I had her get on her knees in front of it. I unzipped my jeans and let them drop. My hard cock sprung free.
“Look in the mirror,” I said. “I want you to watch my cock slide in and out of your slut mouth.”
She did as she was told. I guided her head as I slowly slid my cock in and out of her hot little mouth. She left a trail of red lipstick on my shaft.
May started getting really excited. She moaned and went faster. It felt amazing.
“Can I have your cum?” she asked.
“Yes. But not like this.”
I pulled her to her feet. I took the mirror and moved it next to the bed.
“Take off your skirt. Unbutton the blouse, but leave it on.”
She did as told. I kissed her again and then roughly spun her around and bent her over the bed. She was facing the mirror. The reflection showed me behind her, quickly undressing.
I pulled her panties down as far as the garters would allow. I lubed up my cock and her ass. Grabbed her hips. I could tell she was nervous and thinking about stopping things. So I didn’t hesitate.
She groaned like a little slut as I slid my cock in. I pulled her long hair.
“This ass is mine now. You like me fucking your ass?”
She could only nod.
“Is this better than a toy?”
She nodded again.
We both stared in the mirror. Her little hard cock swung back and forth as I mine slid in and out of her ass. Her mouth was wide open. She kept moaning.
“I’m fucking you right here where you fuck your girlfriend, May.”
“Yes.”
I started driving faster. Her sissy ass was so tight. She was so sexy in lingerie. I reached around and started tugging her cock. She put one hand over mine and helped. I grabbed her head and shoved it hard down into the bed. Her hips were even higher. She grunted and started to cum and that was my signal to finish. I pumped as hard and deep as I could and came inside her ass.
I tossed a $100 gift card to a lingerie store on the dresser before I left.
“But yourself something nice and invite me back.”
After that, she didn’t go AWOL any more.
Source: reddit.com/r/gonewildstories/comments/912hp8/mt_the_asian_crossdresser_who_kept_posting_on