The first time I saw Zoey was on a hookup site.  Asian. Mid-twenties. Long black hair. Dressed in a royal blue satin corset, panties, black stockings, and high heels.  She didn't show her face or her cock. Just a sexy body in lingerie.

It was just still photos on that first post.  But over the course of a year, I saw more ads posted to different sites.  Sometimes there'd be videos. In one she rode a dildo in a leather dress and stroked her cock.  She was getting bolder. She posted links to an Amazon wish list and promised to share pictures if people bought her lingerie.  

At first, I assumed she was just a crossdresser who got off on exhibitionism and wanted to trick men into buying her gifts.  But then she started hinting at more. She wanted to show off for a sugar daddy in person. She wanted to give a man head. In one oddly specific post, she offered head for a mechanic who could repair a sports car.  I have no idea if she couldn't afford the work or was just getting off on the idea.

That when we started corresponding for the first time.  I told her about my experience training submissive sissies.  I mentioned I'd be happy to buy her lingerie. She seemed very intrigued.  Then she disappeared. No responses to my messages and no new posts on her usual sites.

A few months passed before she popped up again.  It was another personal ad looking for fun and a sugar daddy.  We reconnected. She admitted she'd never gone all the way with a man but it was a constant fantasy.  The closest she'd come was giving a guy head in college and it didn't involve crossdressing.  

I was very open about wanting to fuck and being willing to spoil her like a princess.  Zoey admitted she liked the sound of that but also found it intimidating. She wasn't sure she was ready to go all the way.  I promised that as long as she sucked cock I wouldn't push for more. We went back and forth with dirty emails. And then she ghosted a second time.

They say the third time is the charm, but that wasn't the case with Zoey.  We reconnected and she ghosted again. The same thing happened the fourth time we started messaging with one another.  We got as far as making plans to meet and then she was gone. I didn't hear from her for months. It was the longest time she'd been away since I first noticed her posts.

Then out of the blue, she sent me a message one day.  I knew right away she was serious. She'd decided the fantasy wasn't enough and she wanted the real thing.

Actually making plans was still a chore.  She suggested we get a hotel room and I was fine with that, but I told her she needed to arrive dressed.  The idea of that made her nervous. She wasn't ready to dress in public.

So then I gave her my address.  I told her she could pull right into the garage and nobody would see her.   But even the idea of driving dressed made her nervous.

The only thing she would agree to was me coming to her.  The problem was she lived her fiancee who had no idea she crossdressed or wanted cock.  It had to happen during the day when the fiancee was at work.  

Finally, we agreed to meet on a Tuesday during the day.  We exchanged phone numbers.  

When she told me she fantasized about being manhandled, my dominant nature took over.

"I'm not wasting my time on a boy in lingerie," I texted.  "When I arrive I expect you fully dressed. Feminine. A good girl who is sissy and willing to please.  Hair styled and wearing makeup."

She protested and said she only owned lingerie.  I told her to go shopping or borrow her girlfriend's things or she could keep having sex with toys alone.

"Yes, sir," she responded.

"Don't disappoint me," I told her.  "Don't open the door in yoga pants. I want you dressed like a slut ready to hit the town. Otherwise, I'll walk out the door."

She tried to play it bratty.  

"I don't believe you'll leave if I'm just wearing lingerie."

"Try it and find out the hard way," I responded.

We kept exchanging dirty texts. She'd tease with pics in lingerie.  She emphasized she wanted to be used by a man but never had the courage. We agreed a safe word might be a good idea.

I showed up an hour after her fiance left for work.  I was dressed in jeans and a button-down. I knocked on the door.  No response. I knocked again and waited a minute. I started getting the feeling she was ghosting again.  I got my phone out and started to text her when the door opened just a crack. A meek voice invited me in.

Zoey was taller than I expected.  She was close to five-feet-ten-inches in heels. Very slender with feminine features and long black hair parted in the center and chiseled cheekbones like a model. She had on red lips stick, black heels, a silky white blouse, and white skirt with black polka dots that hugged her tight ass.  She had on black stockings held up by garters that were peeking out beneath her skirt. The blouse was so thin I could see the pattern on her lace-trimmed blue bra.

She shyly asked me if I approved.  

"Show me what's under your skirt."

She slid it up and revealed a blue satin garter belt with black lace trim and matching panties barely containing her bulge.

I told her I approved.

"When is the last time you did something like this?" I asked.

She told me she'd met two guys since we'd first corresponded almost a year earlier.  She went to the first guy's hotel room wearing lingerie under her clothes. It was the first time she'd given a blow job since college and the first time anyone had ever seen her in lingerie.  

The second guy was also at a hotel and still only oral.  She'd made a video at that time. I told her I'd love to see it.

She led me to her laptop and pulled up a video.  There she was in a black bodystocking. I watched that pretty face go to work on some anonymous man's cock.

"Looks like you're pretty good," I said.

"I'm very good," she responded.

"Do you get excited?"

"I get so hard," she said.

I asked how she handled that.  She told me she jacked off later.

"So you never fuck?" I asked.

She shook her head.

"But today you're giving me that virgin ass, aren't you? I've seen those videos of you riding a dildo.  You want this. You've been training."

She looked away and blushed.

"I don't know," she said.  "I don't know if I'm ready."

I stepped forward and took her hand.  I pulled her to me. I could tell it was the first time a man had been assertive with her.  She had probably only been with guys who were curious and nervous. I lifted her chin. Those high cheekbones looked sharp enough to cut glass.  If she walked outside she would have no trouble passing.

I kissed her aggressively.  I slid my tongue into her mouth.  I guided her hand to my throbbing cock.

She moaned softly as our lips parted.

"A man has never kissed me," she said.  "Normally they just..."

"There isn't anything normal about me," I interrupted.  "I'm experienced. I know what I'm doing. I know what I want. You're not dealing with some curious married guy trying to sneak out for some head."

She smiled.  I pulled her close and wrapped on arm around her slender waist.  We kissed again.  

I ran a hand up her thigh and under her skirt.  I touched her stiff cock.

"Show me your bedroom," I commanded.

"We can do it right here," she said.

"No.  You made me come all the way over here.  You're going to suck my cock in the room you share with your fiance."

She led me down a short hall.  The bedroom looked like a bomb had exploded.  There was a pile of tiny panties and other clothes on the floor. They looked too small to contain Zoey's bulge.  They must have belonged to her fiancee.

There was a full-length dressing mirror in the corner.  I pushed Zoey to her knees in front of it. She knew what was expected.  She unzipped my jeans and took out my hard cock.

"Look in the mirror," I told her.  "I want you to watch my cock slide in and out of your beautiful lips."

She did as she was told.  She left a trail of lipstick on my shaft as her lips slid up and down. She started getting into it and moaning like a good whore. She knew how to please.  Any trace of shyness disappeared.

"I want your cum," she moaned.

"It's yours," I grunted.  "But not like this."

I pulled her to her feet.  I went back and pulled the dressing mirror to one side of the bed and then led her to the opposite side.

"Take off your skirt.  Unbutton your blouse, but leave it on."

She did as she was told.  I pulled her close and kissed her sensually.  Then I spun her around so her back was to my chest. I bent her over the bed roughly so she was facing the mirror.  I started undressing behind her.

"I don't think we should," she protested.

"I didn't ask what you think," I said.

I lubed up my cock.

"I'm not ready. I changed my mind."

She started to stand up.  I put my hand on the small of her back and forced her back down.

"I'm taking that virgin asshole," I said.

"Please don't," she whimpered. "Please, sir.  I changed my mind. I can still get you off."

"I'm going to let myself out," I answered.

I pulled her panties aside enough to expose her hole.  I gave her hair a firm pull.

"Don't," she whined as I put the tip of my cock between her cheeks. I hesitated, just to make sure she was really consenting.

"Did you forget your safe word?" I asked

She shook her head.

I jerked her long hair roughly. She cried out and arched her back and ass.  My cock slid right in.

"This ass belongs to me now, Zoey, doesn't it?"

She just whimpered.

"You like it, don't you?  Is this better than your toys?"

She nodded her head assertively and moaned.

"Tell me you like it or I'll stop," I commanded.

"Yes, sir," she said.  "Please. Fuck me, please."

"Is this where you fuck your fiancee?"

She nodded.  I alternated slow, deep strokes with a quick pounding.  We watched one another in the mirror. She balanced on one arm and rubbed her cock with the other.  Her moans got louder. When she started cumming it was all I could take. I fucked her as hard as I could.  And then I blew my load right in her ass.

Afterward, I left a hundred dollar gift card for Victoria's Secret on the dresser and told her to buy something nice for next time.

She didn't ghost again after that.