The Perfect Date - Part 6 (Patreon)

You can tell a lot about a person from entering their home; it was part of why I never innovated anybody back to my box of an apartment, besides the fact that there was barely any space. My half empty fridge, discount bin clothes and sloppily maintained furniture would scare off anybody; a pathetic, sad person lives here. That’s what it would say. Even with this new job and the money coming in, it would take time to make it look like any sort of respectable man lived there.

Calvin’s apartment on the other hand screamed try hard; everything was designer in the most gaudy ways, especially the things that didn’t need to be. His couch had french words embroidered on the edge, his kitchen full of shiny appliances with their brand names prominently displayed. His Gucci coats and other designer shoes lined the doorway, ready for guests to subtly notice so he could brag without ever opening his mouth.

It was clear this man had put ample effort into making himself look above his class; I wondered just how much credit card debt he was in, paying for all this. He was the last person you would expect to have such a fetish for trashy women; and yet here we were, necking in his entryway up against one of those expensive coats.

“Soft isn't it?” He cooed, running a hand down the lining and onto my face, “It cost almost as much as you did tonight.”

Ah, so that was it; Calvin just liked being better than other people. He wanted a dumb, trashy bimbo to make himself feel superior and smart. No wonder he’d sent so many women back to the agency, pride was a strong thing and most men wouldn’t bring themselves so low. To let themselves be talked down to by such a prick but I was over that. I was way too horny to have any sense of pride left and I was glad for it.

“Wow, I can’t believe you have that much money to spend on clothes.” I gushed as if it were the most amazing thing in the world.

Suddenly an idea formed.

“I’d love to have these sorts of clothes.” I sighed, with a pout. “The agency dresses me each time, imagine how good I would look on your arm in something designer.”

I was being transparent; yet Calvin grinned at the idea. I could see it in his mind's eye; imagining me all dressed up in finery still acting the part of the dumb bimbo.  I reached up to cup his face.

“I bet you could mould me into a real lady.”

He shivered, crushing his lips back against mine now with a full erection pressing into my crotch. God, he was such a trash bag, I loved it. I let his tongue pour into my mouth and my body sang; it was ready to be ravished and I was done fighting. I fully let the programming take over as my fingers dexterously unbuckled Calvin’s belt and pants, pulling them down and ripping open his designer shirt so hard that the buttons bounced on the hardwood floors.

“Oopsie.” I giggled.

“You should be more careful,” he growled between kisses, “This shirt is silk.”

“I’m sorry, you just turn me on so much I couldn’t help myself.” I pouted, “Can you forgive me, Cal?”

“We’ll see.”

He ripped off my own clothes with gusto, making me gasp each time fresh air brushed against my skin. I felt wild and out of control; it was intoxicating. For the first time since taking this job, I forgot all about the money, I was doing this because I wanted to.

Things seemed to move too fast for me to keep up, or perhaps that was the alcohol from dinner in my veins. Before I knew it I was fully naked, pressed up against the wall with Calvin’s pants around his ankles and his shirt barely over his shoulders. Thai was actually happening. I wrapped my legs around his waist and pulled him to me, shivering as I finally felt his cock penetrate me.

It was odd; the spike of pleasure that filled me as he slid inside was not as stark as I’d imagined it being, yet it was satisfying in a wholly new way. It wasn’t the kind of gratification I was capable of as a man and the moment I realised that I knew I would be doing this again. Many times, the extra money it would earn was just gravy.

Calvin held me up against the wall and continued to thrust into me; hard and fast with zero concern for my own pleasure. He was only interested in serving himself and for some reason that turned me on all the more. There was something degrading and yet freeing about being seen as nothing but a sexy object, I could give in to my own desires fully and know Calvin would never look down on me more than he already did.

So I threw back my head against the wall and wailed, I rolled my hips as much as the angle allowed and I came. I lapped up every bit of pleasure, half out of spite so that I came more than once before he was done. When Calvin finally thrust into me one final time I watched his face twist in ecstasy before slumping against my body and crushing it against the wall.

I waited for shame or embarrassment to wash over me, but it never did. In fact, a strange sense of pride filled me as Calvin lowered me to the ground; I thought selling my body for money would make me degraded and pathetic but really, I’d don’t nothing but win. I would soon have several thousand dollars in my pocket and the memory of some of the strongest orgasms of my life. Plus the knowledge that I just blew Calvin's mind. I could see it on his face, he was already thinking of hiring me again.

He slipped a bracelet, one he had for just such occasions I’d wager, around my wrist. The only clothing I had on now.

“Something pretty, I want you to wear it on all your dates. That way at least in spirit you’ll know who you belong to.”

“Oh yes.” I lied smoothly, “You’re the best date I’ve ever had.”

He grinned as if it were the obvious answer and I felt my wallet get heavier knowing more nights with Calvin were in my future.

~

Several weeks of consistent dates with Calvin had my bank account fuller than it had ever been. I was coming to enjoy my time as ‘Bambi’ as well, Calvin may have been an ass but he was an easy to manipulate ass. Especially when I had tits the size of melons. Not only did I earn a generous tip each time but he would send me home with expensive presents, some of which I sold but many I kept. I spent so much time as a woman these days that I was coming to enjoy having a few pieces to call my own.

Gregory had called upon me several times as well and the juxtaposition of Calvin against a true gentleman really was night and day.
With Gregory I got to enjoy being a sophisticated woman about town, with Calvin, a trashy whore. Both were fun in their own way and I’d long given up depriving myself of sexual pleasures as a woman. I even managed to coax Gregory into bed once and enjoyed a languid night of love making. With Gregory taking special care to make me cum several times over before seeing to himself.

“You’re becoming one of my best hires.” Peter praised at my first annual review, “I have to admit, I thought you were a flight risk, some people just get a few thousand and run before their pride gets too diminished.”

I just giggled, the girlish affectation bubbling up even now as I sat in my male form.

“I don’t see anything I do as degrading, if anything you’re paying me to have fun.”

“What a wonderful way to think of things.” Peter grinned.

“Both Calvin and Gregory have expressed an interest in hiring you long term.”

“Long term?” I asked.

“Yes, it is a service we only offer with our most experienced and trustworthy women.” Peter explained, “To be transformed for full weekends, sometimes more. I believe Calvin wants to bring you home to his family over Christmas, and Gregory wants you to accompany him on a week-long business trip to France.”

My smile couldn’t get any more excited; both sounded like a lot of fun.

“You’ll be paid well of course.”

“Of course.” I nodded, as if I even cared.

I had more than enough money to do whatever I wanted now, and I went on so many dates that I barely ever had to pay for my own food or entertainment anymore.

“Sign me up for both.” I grinned.

“Wonderful!” Peter clapped his hands together. “Keep this up and you’ll be spending more time as a woman than a man!”

He joked of course but if I was honest with myself; that didn’t sound half bad.