Crazy or what? © Elaine 2021
Meet Catherine Reid a twenty-nine-year-old with a difference. She's successful, rich and can have any man she wants under her thumb. That is until they find out about her little secret. She decides to take on a house sitter to look after her exclusive house in the hills above Malibu. Only it turns out that the guy she has in mind is a bit of thief and jack the lad. They eventually fall in love though.
This story is very loosely based on the movie Me Too Madness which was recently released by Louise Linton but I figured I would give it a significant transgender twist. The setting, the persona and drive are much the same except this Catherine isn't homicidal. However, that said, she is by all means very atypical.
Many thanks go to Linda Coleman for editing help.
Chapter 1 - It's all about me, me and me
I'm proud to say that I'd made my first million by the time I was 19 years old, thanks to invaluable help from my late father. From then on it just became easier and easier to make more money. Our company was valued at 100 million by the time I was 25 and now we will report next week that we have a net worth of half a billion! My old man who was also my best friend tragically died suddenly of a heart attack when I was just 26.
Despite the enormous setback of him dying, the company has continued to boom and so it's also proved how energetic, successful and passionate I was. After my father died, I also decided that there was nothing that could hold me back from starting my next major project. Namely me.
It turned out to be more difficult than I'd ever imagined but with millions in the bank, it wasn't impossible. Besides the six-figure sum, it did take a lot of time, some pain and effort but just three years later at the tender age of 29, I'd become a really gorgeous blonde businesswoman called Catherine Reid instead of the geeky kid I'd been 10 years earlier.
My high maintenance look was hard won though, with many painful cosmetic surgeries that needed to be endured first. All my surgeries were now done except the final one. I had as gorgeous a pair of pert pear drop shaped breasts as any woman my age, I had straight veneered dazzling teeth, a trout pout pair of cocksucking lips, a nipped in waist helped by the removal of a couple of ribs that were then used to artificially widen my old boy hips and lastly several major facial feminisation surgeries.
My face now always features long implanted eyelashes, high arch tattooed eyebrows, ears that are pinned back and an oval face that shows no traces of masculinity. On my fingers my Chinese manicurist always keeps my nails long red and oval shaped. I always wear the latest Paris or Italian designer clothes and usually 4- or 5-inch stiletto heels are on my feet.
I recently completed the purchase of a large modern Malibu mansion complete with a garage for five cars, a deep swimming pool and a large landscaped garden, well away from any prying eyes but it does get lonely at times. So, I decided to advertise for a special lodger to look after the place, when I was away on business and for much needed company when I was at home.
Having set the scene, the story starts in the boardroom of my company with all my male directors facing me before we reported to our shareholders on our results the following week. I know some of them lust after me, but they simply don't know anything about my past as they all joined after I completed my transformation to blonde heartbreaker. One or two would have liked me as their trophy wife as I'd already had concrete marriage proposals, but I just tell them I'm not ready to settle down as I'm enjoying my career too much. Besides they would probably run a mile if they saw what was between my legs.
"Well gentlemen, I think we should be pleased with this wonderful set of results. The company has grown in leaps and bounds this year with major orders to supply the Gulf states with our equipment following the problems there nearby. I'll propose that these accounts be approved do we have a seconder?" I asked looking at their faces through my long lowered eyelashes.
Jeremy Wheeler our non-executive director meekly put his hand up. "I'll second then Catherine."
I licked my lipstick covered lips still relishing the effects of the lip fillers I'd had a few days earlier and asked, "Thanks Jeremy, are there any dissenters?"
There were none.
"That's good then gentlemen," I said happily with my bright pink lips parting to reveal my pearly white veneered teeth.
This year, Forbes ranked me the 47th wealthiest person in the country in my age group which was impressive. When the company results are announced next week, I already had excellent hopes of going further up that list.
"That will be all then gentlemen for this meeting I assume?" I asked as I was anxious to get back to my office.
"No sorry, not quite Catherine," said Mitch our Finance Director apologetically. "I've heard a rumour that we could ourselves be the target of a takeover from our big rivals on the east coast. If they took control of the business they'd probably shut us down and move production to their plants in Honduras or Mexico. We could all be out of a job if they succeed."
"Obviously I've heard that rumour too Mitch," I replied. "If our share price goes up next week as we expect after we announce these results, then they'll have no option but to bid top dollar to get us. Since we are all major stock holders then we could retire as very wealthy people if they succeed. Anything else to discuss before we go to lunch?"
They all shook their heads in the negative.
"Well the meeting is adjourned, and I suggest you get back to your desks to make some more fucking money," I suggested with my eyes twinkling wildly under my long eyelashes.
One by one they filed out of the boardroom before me back to their plush offices. I got up last relishing the sound of my new 5" gold stilettos clicking delightfully on the tiled floor as I walked out. I was dressed in a pair of pristine white knee length culottes, a pale-yellow silk blouse and a white jacket of the same material that I'd had specially made to match the culottes. I walked into my office on the top floor and eagerly sat with my feet up on the desk to admire my elegant new Jimmy Choo shoes. They cost a lot but they are so worth it.
The phone rang, and I picked it up. It was Gloria my ever-efficient secretary. "It's George on the line and he wants to speak to you urgently."
"Put him on!" I ordered punching the speaker phone button with the tip of my nailed finger. I noticed my recent manicure already needed attention again badly with chipped polish uncovering half my false nail.
"Catherine, I have some very good news for you," he said happily.
"I'm listening. What did he say?" I asked referring to the boss of the company we were trying to buy.
"He says we can have his company for nothing less than 5 dollars a share," George replied.
"Tell him he's fucking crazy! Tell him that we know the market value of his company is just over 3 dollars a share and that we'll only go as high as 3.50!" I replied. "Also tell him if he accepts, we'll pay him personally another 100 thousand in hard cash and he can continue to run the company as our new subsidiary."
"I will do and I'll call you back as soon as," he replied.
"Also tell him that when he says he's turning his company around, he's really fucking not," I replied. "The stupid fuck failed to secure the funds he needs to invest in the business. If he doesn't accept our offer, his company share price will plummet and they'll fucking fire him. Have you got that George?"
"Sure Catherine," he replied.
"Oh, and George very good work," I said switching off the speaker phone before he could say thanks.
At one time we'd been lovers and George was really amazing in bed. He'd winced at first when he found out all about me, but he soon got into the anal sex and became really good at receiving and giving. Particularly the latter.
I sat back in my executive chair and kicked off a heel to reveal my lovely pink coloured toes happily knowing I was doing well against all these idiot men. I may have been a man too at one time but now there was no maleness left except perhaps what was in my ruthless brain. I looked and sounded completely female, in fact I looked drop dead gorgeous and they all knew it.
I had to deal with a few more problems before I poured myself a well-deserved cup of unsweetened decaffeinated coffee for lunch. If there was one thing that sucked about being a girl, it was feeling permanently hungry most of the day. Until I ate my dinner at around 7 pm I lived on coffee and maybe the odd stick of celery or a carrot.
Later that afternoon, George rang back to say that he'd finally bought out the company for 3.50 a share and with a 120 grand brown envelope pay off to the owner.
"Well done George," I said warmly. "You just saved us another 30 grand. Has he signed the agreement yet?"
"Yes, I got Cheryl to email me our standard agreement and he's signing it now."
"Right scan it and email it to me and to Mitch so that he can work on it over the weekend," I replied. "I just hope our new company doesn't go tits up on us now."
"Catherine, I really don't think that the fundamentals in this company are as bad as you might think," he replied.
"As soon as he's signed, then tell him you want to see the real company books immediately," I replied. "If he doesn't agree then threaten to tear up the agreement and tell him we would need to quickly reassess our possible investment in his fucking company!"
Men being men they want sex so badly. George closed off by saying, "I hope that we can get together again when I get back."
"We'll see George. Just close the fucking deal first!" I replied harshly. "Don't come crying to me if it all slips through your fingers and I then fucking fire you!"
As you know by now my name is Catherine and I'm not fucking going to tell you what my name used to be because it doesn't matter. I'm most men's wet dream now thanks to the most amazing surgeons who gave me the kind of body I'd craved all my life.
Since my transformation, I make sure to take very good care of myself. From Monday to Friday I wake up at five a.m. to the sound of my phone alarm. When I wake up and realise who I am again, I smile happily to myself. My life is nothing short of incredible, given what I used to be. No more, geeky kid thank you very much.
For breakfast, I just have a cup of black coffee, with two small pieces of rye bread toast and a boiled egg because it is just enough calories to burn off as I hit the gym at 6am on the way to work. I really work out every morning particularly on the peloton bike I have. I enjoy the class as everyone is so friendly and nice.
Then sometimes some of my employees join me for a class at the office because they need an enthusiastic leader in the front row. That's obviously me out front in my cute pink leotard and pink pantyhose as we ride our peloton bikes, or we do step aerobics.
Obviously, I don't like it when people in the front row don't keep up with the hard pace I set. That shows a lack of commitment and drive not to mention that it is incredibly disrespectful to the rest of the class. After the exercise, I'll shower next to my office and I exclusively use the beauty products I do because they're not only the best, they're also environmentally friendly, and importantly they don't test on animals any more.
Did I tell you yet that after my company, fashion is the most important thing in my life? I'm incredibly happy to tell you then that I'm due to appear in next month's edition of Vogue showing some of my favourite clothes from my favourite designers. One drawback I've noticed is that I've found that I'm rarely if ever comfortable these days but I'm always looking incredibly stylish which is obviously much more important.
Sometimes having to wear high heels and tight-fitting clothes can be a bind and even fucking painful but you just have to grin and bear it, if you want to have style.
After that, the next important thing for me is the accumulation of money. Thanks to my dad, I was born with money, but I soon learnt its value from an early age and I never take it for granted. Put simply having lots of money means I can get the many other things that I like in life. Having money means power and I can get things done when I want. It also means I can avoid the things I don't like, such as fucking awful restaurants, cheap fashions and detestable commercial air travel.
You've probably already figured out that I'm very materialistic, a narcissist, positively self-centred and I don't deny it. I also have severe personality disorders, which manifest in various antisocial attitudes and behaviours. There is also an acute lack of conscience so I don't really care how annoying I can be.
Of course, when I started my transition I had to see a gender therapist and I chose the best one I could find. Anna was the most respected and I was able to easily convince her of my ongoing struggles with my gender dysphoria. She was the one who agreed that I could start taking female hormones and who sanctioned all my surgeries in the beginning. She has given me the go ahead for the final surgery, but I'm in no hurry to remove my pleasure centre just yet. I'm also not sure I'd like having to sit down to pee for the rest of my life and I'm still able to tuck it all out of sight. All the extra oestrogen I take is countered with a few pills beginning with the letter V from time to time.
Now I go to see her not for treatment, but just to prove that I've overcome all my problems and that I'm obviously successful living as a woman. I also want to show her that I possess such extreme intelligence that there is nothing wrong with my life and that I'm happy and content as a feminised male. Lastly I want to prove that I'm also very lovable and a sexy woman so I can enjoy the best of both worlds.
I think women are leading the gender revolution and I'm just so glad to be part of it. In fact, I feel I'm leading the revolution in which women excel. I also employ more women than men in my company but sadly none are as yet in top management roles but that suits me just fine. During the week I stay about 10 minutes away from the office, but on the weekends I go home. Usually I leave the office about 7 or 8pm during the week but on Friday its about 3pm when I get up and head out for my gorgeous mansion in the hills.
Today is no exception and as I pass by my receptionist she very nicely called out, "Have a great weekend, Catherine!"
"Thanks you too, Jenny," I replied not looking at her as I walk in my usual determined stiletto fashion towards the elevator down to the basement and my amazing Ferrari. My feet were on fire after a long day wearing heels, so I was just keen to get home and relax.
"Oh, Catherine my name's Heather but it's okay," she replied but I pretended not to hear. I'm just very keen to get inside my newest toy - my blood red Ferrari.
I've had lots of cars but nothing quite like this one. It has the more powerful V-12 engine mapping, improved aerodynamics and grand prix style gearchange controls. It has an amazing top speed and jaw dropping acceleration and it cost me a lot of money, but it was worth every penny. Driving in stilettos is not for the faint hearted but I'm an expert now, so I don't remove my shoes as I operate the controls.
As I drove home, sadly obeying the strictly enforced speed limit, I noticed that chip on my nail polish again, so I called the nail technician who usually does my nails.
"Can I help you?" he asked.
"It's Catherine. You will recall I hope that you did my nails two days ago," I said. "I have a large chip out of my polish already. You assured me this new gel polish you recommended wouldn't chip and it fucking has!"
"Maybe you hit it against something hard?" he suggested.
"I can assure I didn't hit it against anything, but now my fingernail is missing a big chip and it needs fixing pronto as it makes me look cheap," I replied
"Okay, okay, I'll come to your house tonight at seven," he said apologetically.
"I'll see you at seven then. Don't be late!" I commanded. I could almost hear him call me a bitch as I hung up.
I work long hours, but the weekends are purely for fun and pleasure. There's nothing I look forward to more than my Friday night drive home as I ponder my weekend ahead. I expect this evening to be
particularly interesting as I have someone paying me a visit at five. Unfortunately, I'm running a little late despite the Ferrari's amazing turn of speed.
Then suddenly a car comes out of a side street straight in front of me without stopping. Fortunately, not only is the Ferrari blindingly fast, it's also impressively good at stopping too. I drove on after giving the other driver a finger and shouted, "watch where you're fucking going in future!"
He mouthed back, "bitch!"
I quite like being called a bitch but shouted back, "cocksucker!" just to prove I am one.
I resumed my drive home enjoying the power and the feel of the Ferrari through the bends and swoops through the hills. I do love driving fast. It's an addiction I have and it's one of many I possess. I'm also addicted to good cocaine, fine champagne, exercise, sex with hunky men, expensive designer clothes and shoes and playing mind games.
Just as I drew up outside my driveway gate, another car arrived.
"Hi, I've an appointment at five about renting a room," said this scruffy looking guy who looked as though he hadn't shaved in a week. His car looks to be in serious need of a service or scrapping because of the oily smoke coming from the exhaust. He wore a pair of jeans that best could be described as fit for the bin, a T shirt covered with food stains, a pair of leather boots that he forgot to tie the laces on and then he'd wrapped a sweater around his waist using the arms.
"You're a little bit late," I replied checking my diamond encrusted Rolex. "Follow me in."
"You were late too," he said cheekily as I went to retrieve my Gucci handbag from the passenger seat.
"Well I had a big business deal to conclude today, what's your excuse?" I asked coming back with the bag slung on my left forearm and my gem encrusted iPhone in the other hand.
"Oh, I had to stop for gas," he smiled as he introduced himself, "I'm Clay Mitchell by the way."
"I'm Catherine Reid, so follow me," I replied reluctantly shaking his greasy hand.
"I'm sorry," he said as we headed up the garden path towards the front door.
"What are you sorry for?" I asked turning back to look at him.
"For being a little late," he replied. "Sorry I didn't realise how far it was from downtown L.A. and my car isn't very fast compared to your Ferrari."
At that moment, the wind picked up and it started to blow my long blonde hair everywhere, so I walked as quickly as I could to get inside the door.
"Come on in," I said holding the door open.
"Welcome home Miss Catherine," the house computer then suddenly announced with a feminine voice.
"Wow what a place!" Clay declared.
"It's home sweet home," I declared dropping my Gucci handbag on the sofa for later. "Do you want something cool to drink?"
"I'm good," he replied and so then I added the 'Thank you' that he forgot.
"Sorry, I'm good, thank you," he corrected.
"Don't mind me then Clay, but I'm dying for a fucking drink!" I said heading to the bar where I made myself my usual vodka martini.
"I see you stir and don't shake your drinks," he said observing my expertise behind the bar despite my long manicured nails.
"Yes stirred, wet and just a little bit dirty," I replied. "Are you sure you won't join me?"
"If you have one, a beer would be fine thanks," he replied before asking "So what does your husband do?"
"What makes you think I'm married?" I replied incredulous.
He pointed to the big diamond ring on my left hand wedding finger.
"It was a lovely birthday present from a friend recently," I replied remembering George's big surprise with a smile on my face.
"A nice present from such a generous friend," he declared taking an inelegant swig from his beer bottle, while I sipped my martini. I held my finger out, so he could take a good closer look at the large stone.
"That's quite a stone," he said.
"That's four carats of South African de Beers diamond," I replied.
"He must love you a lot," he said looking impressed. "So, are you a hot shot lawyer or something to afford all this?"
"No do I look like a fucking lawyer?" I replied annoyed and before he could answer I added. "I own my company in Los Angeles."
"That's very impressive Catherine," he said. I could tell he was overwhelmed as he looked around with his mouth open as we stood at the bar.
"What do you do?" I asked knowing there was a gaping chasm between us. Not because he looked unemployed but because of his apparent stupidity. I began to feel that killing this guy would probably be a service to humanity.
"I'm in between jobs at the moment," he declared indicating that he was basically unemployed and most probably unemployable too.
"So, Clay tell me then, what did you do last?" I asked.
"I'm an engineer, or at least I was an engineer for Tesla until a few months ago, when I was suddenly laid off," he replied. I knew he was lying but I carried on.
"So, can I ask why are you looking to move out from L.A.?" I asked.
"Just why are you looking for someone to live here?" he replied with another question which can be annoying for someone like me. I decided to humour him.
"I travel rather a lot on business and I live in L.A. during the week," I replied. "So, I need to find a babysitter for my house for when I'm gone." Then I repeated, "Why are you looking to move?"
"My roommate is a complete asshole," he replied and that was obviously lie number 2. I already knew that Clay was just a thief and not a very good one at that. It doesn't take much to realise that he now responds to online ads for room rentals so that he can then rob the owners. What he's doing right now is casing me and my house, or so he thinks but what he doesn't realize is that his being here is entirely by my own design. I wanted to see how he would react to what is about to happen when my cute Thai girlfriend gets here.
"Ok the rent is not cheap at 2000 a month. You have full use of the house except access to my bedroom. That's completely off limits. Got it?" I said making sure he understood the ground rules.
"I got it," he confirmed nodding.
"Great, now wait a moment please while I go and change out of these work clothes," I replied. "I'll be right back in a couple of minutes, so make sure you relax right here while I change."
I quickly walked into my bedroom and decided that I would change into my favourite long white cotton house dress, with my comfortable white 5" stiletto sandals. I quickly brushed out my long blonde hair, letting it fall over my shoulders and then redid my make-up changing my lip colour to a sultry signal red and then darkened up my eyeshadow. I took out the diamond studs from my ears and put in some earrings which were long, sparkly and dropped almost to my shoulders. Fastening the clips of the earrings behind my pierced ears used to be a problem with long nails but it's not now.
"Another striking outfit Catherine," he said as I joined him a few minutes later. He was looking out of the living room window down into the valley below.
"Thank you, so let me give you a quick tour of the house. Obviously this is the living room," I said. "As you can see it's an impressive living area with lots of glass, light and space."
"I'm truly very impressed," he said.
"The only rule here is there is no red wine," I said. "A red wine spill would destroy the soft chamois leather of my sofas."
"Well I'm more of a beer guy myself as you can no doubt tell," he replied. "So that won't be an issue."
"Good, it better not be!" I replied leading him into the dining room. "This is the dining room which I only use rarely for dinner parties. As you can see it can seat a dozen people easily."
"That's a lovely painting Catherine," he said taking a closer look at it. "Was it very expensive?"
"That's an absolutely revolting question, Clay," I replied walking out and added. "Follow me please."
So, I walked out in front, with my spike heels clicking on the tiled floors towards the kitchen. "I have a housekeeper who works here three times a week and she does the laundry, cleaning and the dishes."
"Would she do mine too?" he asked.
"Well yes of course," I replied exasperated. "That was my whole point of telling you."
"That's sweet," he replied lamely as I led him towards the gym.
"Do you lift weights too Catherine or are these just for show?" he asked pointing to the expensive rack of weights.
"Yes, I lift some weights every single day. Why do you ask?" I asked showing him the weights I had and despite my now feminine shape I showed him that although I wasn't as strong as I used to be I could still lift some weights.
"Can I use this stuff in here too?" he asked. "I like to keep fit."
"Well yes of course but if you break anything then it's your responsibility to get it repaired," I replied.
"Got it?"
"Got it Catherine," he smiled.
"This Clay is my garage," I said, and he was impressed with the only car I'd parked inside.
"It's a gorgeous looking Camaro Catherine," he said taking a keen closer look inside the cockpit. "I must say I'm surprised that you own a vintage muscle car like this."
"Just why is that?" I asked impatiently.
"Of all the cars a chick like you could own, I wonder why you didn't go for an Audi convertible, or a Ferrari Dino or even a beach buggy," he said annoying me considerably.
"I own a Camaro because simply I bought it after I'd made my first million," I replied annoyed because he's more stupid than I expected and I think he's about to make some other wisecrack. Fortunately, he doesn't.
We stepped outside to look at the view down to the coast. I'd selected this dress on purpose because there is a lovely breeze blowing which is giving a lovely lift to the fabric. This gives it an almost slow-motion ghostly quality.
"So do you like my house?" I asked.
"It's a dream house," he replied enthusiastically. "I think you're very lucky to own it."
"Thanks I feel very lucky to own it," I replied. "I'm glad you like it."
"I do very much. Up here there are no neighbours, so you could throw some pretty wild parties and not get any complaints," he said.
"How observant," I replied sarcastically. "Activate party mode."
"Party mode activated," was the computer response and loud party music started playing from all speakers around the pool and patio.
"Sometimes I come out here on a warm summer night and just absorb the ambience," I replied swaying gently to the music. "Up here the sky is crystal clear and so at night you can look up at the universe spread out like twinkling diamonds. One day I'd like to fly to Mars."
"Mars? Why Mars?" He asked as he started to move with me to the music.
"I'm just fucking with you. God, you should've seen your face. You're so easily fooled," I said laughing. "That was way, way too easy."
"Yes I'm an idiot," he admitted. "For a moment there, I really thought you were serious about leaving all this behind for an alien world."
"Well, my company supplied components to Space X launch vehicles so perhaps we can't rule that out can we?" I replied. "But no I don't want to go to Mars. At least not until a proper city has been built."
"Sorry but I gotta use the toilet," he said pointing down to his crotch sweetly just like a little school boy. After I switched off the music, we walked back into the house so I could show him the guest restroom. When he was inside, I went into my CCTV room and watched what he was doing.
As he sat on the toilet taking a dump but he then chatted eagerly with a guy called Chad on his mobile phone.
"Chad this Catherine is one foxy lady, she's loaded, and a total MILF. I'm talking serious pussy and her mansion is just insane. I would actually want to live here if only I could afford the two grand a month rental," he said.
"That's not the plan!" replied Chad angrily. "Don't get carried away man! Keep your focus on the task at hand! We can't afford any fuck ups."
"All right Chad, but I'm pretty sure she wants me for sex, man," Clay replied.
"You're a cocky little bastard!" I said out loud when I heard his comment as I watched on the monitor. "You could be in for a rude awakening."
"How old do you think she is?" Chad asked.
"It doesn't matter what age she is, her body and her face are gorgeous. I'm beginning to think she wants a man around the place just to keep her serviced. Do you know what I mean?" Clay asked laughing.
"Yes but you're not a stud anymore," Chad replied. "Maybe you should give your mind a rest. Just stick with the plan, grab what you can and get the fuck out of there!"
"All right," Clay agreed finishing his business on the toilet.
As I watched him wash his hands. I decided he wasn't going anywhere just yet. As he emerged from the toilet and waited in the living room, I quickly changed into a red mid-thigh dress and my red stilettos. I freshened up my lipstick and then joined him in the living room.
"Are you going out tonight Catherine?" he asked when he saw me walking into the room.
"No, what gave you that idea?" I shrugged.
"Your new dress wouldn't look out of place at a nightclub so I thought maybe you were going out later," he said giving me a face to face compliment. "You really do know how to show off in a dress like that."
"Why thank you for that kind compliment," I replied heading for the drinks cabinet to make up a fresh martini. "Do you want one this time?"
"No I'm good," he said and then made the comment. "You really like your spirits huh?"
"Come on, let's have a drink and maybe chat about you moving in here," I replied pouring him a drink and slipping in a mickey at the same time.
"Cheers," he said as we clinked glasses on the sofa.
"Do you like it?" I asked. "It's really smooth tasting."
"It's not bad thanks," he said obviously not really enjoying the ice cold martini. Only his had a little extra sideways kick in it.
"So do you have any family, Clay?" I asked.
"No not that I see anymore," he replied. "Dad ran off with another woman and my Mom died of a broken heart. My brother died in a car crash about five years ago and my sister is married to a stockbroker and is living on the east coast."
"Hmm, that sounds very sad," I replied feeling genuinely sorry for him.
"I'm not too bothered," he said. "I'm used to being on my own. What about you?"
"Well I have a sister who lives down the coast from L.A. and my maternal grandmother lives up north a little," I replied. "She's an incredible woman and we've become very close since my dad died. Would you like a top up?"
He nodded, so I poured the last of the contents of the mixer into his glass. "You need to take it slower as these martinis can be lethal," I cautioned.
After about 10 minutes or so he started drifting in and out of consciousness so I called out loudly, "Clay are you okay?"
"Yeah," he said but he was closing his eyes.
"You were wrong earlier my friend I'm an ILF, not a MILF," I replied but he was already unconscious. "I've never had kids and sadly I can't."
Just then there was ring from the driveway gate speaker-phone. I just knew it was my nail man who'd arrived so I let him in and having been here a few times he knew where to go. I ushered him into the dining room as usual where he set his box of tricks up on the glass dining table top. Clay was sprawled out on the sofa unconscious.
I sat beside him and proffered the chipped finger nail. He asked, "do you want the same colour or a different one?"
"The same darling," I replied and that pleased him no end. He carefully removed all of the old chipped polish using a battery powered tool and then applied the new coating. It didn't take him very long and within 20 minutes he was off home to his wife and kids. He still wanted paid for the visit, but I told him that I didn't expect my nail polish to chip just two days after it was applied. I gave him just ten dollars for his fuel. I was happy as I never allow my nails to go naked nowadays.
After I showed him out, I went back to check on Clay. He was still stretched out on his back unconscious. So with plenty of time before Tukta arrived at 9pm, I changed into my pink leotard, legwarmers, sweats and even pink wrist and head bands to do some rigorous exercise routines in the gym for a quick little workout.
After an in and out shower following 45 minutes of sweaty exercise, I decided I should check on Clay again.
I found that his pulse was quite strong and slow. He was still unconscious, so I must have put too much in his drink. Then I checked on his breathing and was relieved to see that was fine too. "I'm glad you won't die Clay."
That done, I moved into my office to finally have a check up on the day in Wall Street. Small cap stocks outperformed with my company up another 5 percentage points, while the Dow Jones industrial average stood still. I'd just added another 20 grand to my share valuation because of the stock market price increase. I find that making money is incredibly arousing. Then I suddenly wonder what I'm going to make for dinner.
Then I remembered that Mary, the maid would have prepared some meals for me earlier and put them in the freezer. I removed two of the meals, put them both into the microwave oven and re-heated them for several minutes. With the food almost done, I thought I better check up on sleeping beauty yet again. He's still just like a baby so I prodded him with a sharp painted fingernail on his nose.
"Good evening," I said as his eye suddenly opened.
"What the hell happened?" he asked rousing himself. "What the fuck was in that drink?"
"Oh I thought perhaps you didn't like the taste of strong liquor," I replied innocently.
"Wait, I can't tell if you're being funny again," he replied.
"Have some water and dinner's almost ready," I said pointing towards the kitchen.
"Wow look at you, are we going to a party?" he asked seeing me in yet another glittering new dress.
"I don't think I should abandon my commitment to fashion style just because I'm at home," I replied haughtily.
He got up quickly and spied my nephew's BMX bike still on the floor in pieces where I'd left it a week earlier. "What's that bike lying there for?" he asked.
"I gave up trying to put it together," I replied. "The pedal won't go on for some reason."
"Yeah, but what's it doing here?" he asked looking at it.
"It's supposed to be a present for my nephew's birthday," I replied.
He stooped down low and picked up the pedal and then started to screw it onto the bike.
"What did you just do there?" I asked totally astonished that he'd managed it when I couldn't.
"I can put the pedal on for you," he replied picking up the wrench to tighten it. "You have to remember the thread is reversed for that left side."
"Wow aren't you a clever guy," I said. "I thought it was completely broken."
"No it's not broken," he said happily tightening up the pedal and then putting the front wheel into the front forks. "There all done."
"I have a huge IQ and I just couldn't quite figure what was wrong with it," I said.
"You know what it's getting late," he said. "I think I should go."
However, at that very moment my girlfriend Tukta waltzed into the house using the pass key I gave her.
"Oh forgive me Tukta this is Clay, Clay this is Tukta my Thai girlfriend," I said introducing them.
"Nice to meet you," she said to Clay smiling as I walked towards her to greet her with a big hug and a loving kiss on her lips.
"Hello," he replied but she was looking directly at me. We kissed again much more passionately feeling our lipsticks merge.
"Tukta doesn't speak much English," I explained to Clay after we'd kissed passionately for over a minute.
"So how do you guys communicate?" he asked.
"I know a little Thai from my many visits to her country," I replied remembering my trips to the hospitals that specialise in gender change surgery. "She knows a little English too, so we get by."
"She has a lot of tattoos. I never saw so many gorgeous tattoos on a woman," Clay said watching us kiss. "What are you guys talking about?"
"We were wondering if you'd like to stay the night," I replied. "Tukta seems to like you."
"Then I'll stay," he replied instantly making up his mind.
"Oh that's great then. Be a doll and open the bottle of white wine in the refrigerator," I asked him. "Don't you think she has a beautiful smile?"
"She's absolutely gorgeous," he replied.
"Yes she is," I replied. "It's so hard to believe that she used to be a boy."
"What?" he asked his jaw dropping.
"Tukta is a kathoey," I replied and a puzzled look on his face appeared so I explained. "A lady boy if you will."
"You're seriously joking with me again Catherine," Clay replied.
"I'm not you know," I said and prompted her to hitch up her dress hem to reveal a tiny cock and a pair of small balls where a pussy should be.
"Wow I'd never have guessed that," he said mouth wide open.
"I have another shock for you Clay. In case you didn't know I'm one too," I said pulling up my dress to reveal my hard 5" cock wedged up inside my panties.
"Whoa," he said totally astonished. "You're a tranny too?"
"Yes Clay. I thought you knew," I replied. "Do you want to join us? We're going to bed shortly after a little dinner."
"What go to bed with two trannies? Me? Fuck it why not! I'll try anything once with you two," he said approaching us both with his arms out. Tukta smiled and let down her long dark Thai hair so it cascaded down her back.
"She really likes you," I told him.
"And I like her," he said. "She shouldn't have been born a boy that's for sure."
"She gets her gender operation next week back home in Bangkok so I suspect that this is the last time for her," I said. "So no more lady boy but a fully-fledged lady." Tukta nodded approval and smiled.
"So what about you Catherine?" Clay asked.
"I don't have a date set yet. I'm in no hurry for now," I replied.
After sharing the two meals split between the three of us we eagerly went off to my bed. It was certainly a wild night of passion with Clay stuck in the middle. If he didn't like that we were transsexuals, then it didn't show because he had a good solid hard on for most of the time. There were lots of good oral and anal sex, as Clay got into the act of his life as he tried hard to pretend that we were genetic women. He would first fuck me in the ass then push into Tukta with equally great energy. Eventually it got to the point where he really needed to cum, so Tukta gave him fellatio until he did. He fucked her pretty mouth for about ten minutes while all the while he was kissing me and rubbing my tits.
"You have such great tits Catherine," he said as he erupted cum all over her face. "Not too big, not too small."
"You covered her face in your spunk," I said. "The very least you can do is to lick her face clean."
So he shrugged and eagerly cleaned her face with his tongue. After that he drifted off to sleep leaving me and my Thai girlfriend to give each oral sex until we both erupted. Her jism was quite watery and clearly she'd been chemically castrated with the huge amounts of female hormones coursing through her system. I knew that she took more hormones than she needed.
Chapter 2 - In the morning
When the light streamed into the bedroom the next morning, Tukta had already gone off early to catch her plane from LAX to Bangkok and her impending date with the surgeon. I'd seen her off and wished her good luck before returning to bed beside Clay. I went back to sleep as I was pretty tired from all the sexual activity.
"Ah so you are finally awake. Good morning," he said. I struggled to open my eyes thanks to my long mascara clogged eyelashes. "You look really beautiful in the morning."
"Flatterer," I said stretching. "I bet I'm a mess. How did you sleep?"
"Slept like a baby," he said. "I never imagined that I could cum so hard as I did last night. Did I dream it all?"
"Dream what?" I asked.
"That you have a dick Catherine?" he asked.
"Yes you saw it and I'm sure you felt it too in your mouth and ass," I replied laughing.
"Oh, I thought I dreamt that. I thought I'd drunk too much and did you drug me last night?" he replied. "Last night was just amazing!"
"If you say so lover boy," I replied putting my legs over the side of the bed on my way to using the toilet again.
"Come on, come on, you definitely had a great time too," he said watching me paddle over to the toilet on tip toes and then lift the lid. I stood and peed into it to prove a point to him.
"You know you're drop dead gorgeous Catherine," he said looking at me as the sun hit my face making me blink as I walked back on my toes into the bedroom.
"I need my make-up on before you can say that and it's really much too bright in this bedroom," I said pointing to the window where the light was streaming in.
"Why did you buy a house with so many windows?" he asked sitting up in bed as I pulled my shapewear panties up over my little soft cock. "You do know that you're really special I hope."
"Because I'm a tranny?" I asked clipping on my bra and nestling my breasts into the cups.
"No because you're way too convincing as a woman," he said. "I think you're amazing. You're beautiful, elegant and charming. You're also so smart and as sexy as hell."
"Take it easy," I replied and laughed. "My ego is big enough already."
"I'll prove it to you," he said as reached over and pulled me back towards him. I tried to resist, but he was much stronger than me, so I had to let him bear down on my mouth and kiss me passionately.
"See?" he asked. "You even kiss like a woman. Maybe you should go with Tukta to Bangkok too?"
Gasping for breath I replied, "One day I will but not right now. Besides I'm not in any hurry. As you can see I like to stand up when I take a piss. Plus, I like to fuck as well as be fucked."
"I noticed you walked on your tip toes Catherine to the toilet and back," he said lying back.
"So?" I asked.
"You like to walk that way?"
"No it's just painful if I try to walk any other way now." I replied. "When you don't wear anything but high heels then your legs adapt. Now I can't walk except on tip toe or in my heels."
"Your legs look amazing in heels," he said. "I liked seeing your feet in heels above my head as I fucked you in the ass last night."
"It's funny I liked seeing that too Clay. It gives me a nice feeling to know you liked it too," I replied. "What size shoe do you take?"
"I take a size 10," he said.
"Pity I was going to let you walk in my heels but I'm a size 7," I replied. "So what do you really do for a job, Clay?" I asked knowing he was more likely to open up since we were freely chatting.
"I do odd jobs here and there. Nothing consistent, I just pick up the work where I can find it," he said in a quite melancholy way. "One day I might pick fruit or another serve drinks in a bar."
"Don't you have any desire to get something better?" I asked. "Maybe join the corporate ladder? Perhaps I could find you a job worthy of your talents at my company?"
"I mean I would if I could," he said. "The truth though is that I dropped out of university in my second year because I couldn't afford the fees. I'd lost my funding."
"What did you study?" I asked.
"Engineering," he replied.
"What kind of engineering?" I asked.
"Mechanical engineering," he replied.
"I think that you've an obvious talent at that," I replied. "You should go back into it. I think you're really smart, clever and witty. Maybe even just a little bit handsome. You shouldn't waste that talent on odd jobs. I really think you owe yourself a better life than that. I'll make you some breakfast and then I'm going out to the gym and get some food from the deli, so rest up and I'll be back soon."
I put on my pink stretch pants, pink sports top, I quickly pinned my hair up into a high ponytail and headed for the kitchen. I pulled out a few strips of bacon, cracked two free range eggs open and cooked him some bacon and eggs. I did some pieces of toast for him and for me. Finally, I made us a cup of coffee each and then headed back to the bedroom.
He'd dosed off again so I ate mine quickly and left. I decided I would wake him by phone on the way to the gym. I tried several times to call but his phone was engaged so I figured he'd seen his breakfast.
Chapter 3 - He fucking robs me
The following information I was able to find out, when I looked at my CCTV system after I got back from the gym just 90 minutes later. I looked at him sleeping and saw him answer his phone only the call wasn't from me. The call woke him up and he started to talk loudly into the phone.
"I'm still here man. You won't believe the night I've just had. I was with two gorgeous trannies last night. Catherine the MILF I told you about, unbelievably she's one too," he said then he put it on speaker as he obviously had to get up and visit the toilet. "She's not here right now and shouldn't be back for an hour or so."
"Ah so that's what you've been doing," his friend said. "Get out of there and take what you can get."
"I really don't think I want to take any of it, man," Clay said pulling up his boxers.
"Don't be stupid, see what you can carry and get the hell out of there," his friend advised.
"You don't understand man, I think I really like her," Clay said.
"Don't you mean him?" he asked referring to my birth gender. "What the fuck are you thinking? Do you really want to take pity on a tranny? Your brain has definitely fried and suddenly you think you can have a relationship with a dumb broad. Do you need any reminding that this is all fake?"
"It's not that easy man," Clay replied obviously annoyed at his friend.
"She's not your girlfriend or your boyfriend come to that, so get your sorry ass out of there," he said getting angry. "We're in a con game and this is just a hustle so don't fucking lose your edge."
"I don't know, man," Clay replied dithering. "It just doesn't feel right after the immense hospitality I got given last night."
"With two trannies? Yes, that was some hospitality. Stop dawdling and get out with what you can." He repeated sounding increasingly annoyed. "There's no time for that shit because if we don't pay our debts we'll be the trannies when they cut off our nuts and feed them to us."
"All right, all right!" Clay said reluctantly getting up and then pulling on his tired clothes.
When I got back home, I was at first pleased to see that Clay's car was still parked up but then that turned to disappointment and anger when I saw that the garage door was wide open and my prized Camaro was gone. When I got into the bedroom, I noticed that he'd also helped himself to the jewellery I'd left out of my safe from the night before. There was about 50 grand worth of jewellery stolen and the car was priceless. The fuck!
"I made him cum hard last night, made him a nice breakfast and then he goes and does this shit," I said heading for the shower to wash off my aerobics sweat.
Unbeknown to him though I'd accessed his phone and added it to mine, so I could see exactly where he was at any given moment. I had his number so I'd just call him to bring my jewellery and the car back or else he'd get time in an LA prison cell. So after I brushed my blonde hair out, I called him.
"What the fuck is wrong with you?" I asked him out front. "You stole my jewellery and the Camaro, and I want them back right now!"
"Get lost!" he declared. "I already fenced it all."
"You better not have," I replied. "I'm very disappointed in you. I thought we'd connected."
"I don't connect with trannies," he insultingly declared.
"It still didn't stop you creaming yourself last night though did it?" I said.
"No that was quite unique," he declared. "Last night was rather special but you should know that business is business!"
Then his friend Chad spoke, "why are you still wearing her fucking jewellery?"
"There's no safer place for it than where it is," he said back to him but I overheard. Then the phone went dead.
No time for underwear so I rushed to my wardrobe, put on a pair of skin tight black leather pants, my knee high black spike heel boots, my cream silk blouse and my black leather biker jacket. I tied my hair up into a high pony tail and put on my baseball cap. Grabbed my sunglasses and the keys to my Ferrari, and headed out again to confront him.
"Of course he'd fucking steal my car! Why had I been so stupid to trust him?" I shouted out angrily as I clicked my heels back towards the red Ferrari. As I headed out I thought I already knew the answer. I was falling in love and that had clouded my judgement somehow.
Only one thing to do and that was to get my property back. I'd just treat it as another challenge, but perhaps it was going to be a situation that I simply couldn't undo very easily. He was proving to be a big challenge and I needed to focus. And the best way to focus is to wear a fantastic sexy outfit that will show I mean business too.
As I drove out of the gate I declared, "You thieving treacherous little shit Clay. To think that I actually liked you and let you touch my body. I'm gonna slice your face off with a cheese grater and then feed your testicles to the lions at the zoo."
So I followed his location on my phone and sure enough I parked up right beside where my Camaro was sitting. They were inside eating Mexican food so I put on my sunglasses and walked out towards the restaurant.
"Hey baby!" Clay declared nonchalantly as he saw me approach their table in my dominatrix outfit. "Take a seat!"
"No thanks! Just give me my jewellery and the car keys back right now!" I declared with my hand outstretched. "Clay baby, I never told you to take my car and stuff and then leave!"
"You won't miss the car honey, you can just buy another one," he declared not in the least bit sorry.
"I wish it were that simple, baby," I replied. "I need that car back asap!"
"No can do honey," he declared in between bites of his taco. "The car has a buyer already. We're meeting him in an hour, so there's not much you can do about that. How did you find me anyway?"
"Did nobody ever tell you to turn off your location services?" I asked.
"No I didn't think about that!" he declared.
"You are juvenile," I replied. "I know where you've been and what you did at places all over L.A. which I think the cops would be very interested to know about. Shall I call them so you can give them your undivided attention?"
"What the fuck?" Clay said clearly unhappy.
"There are dozens of houses you've ripped off over the last six weeks. And I also know about all the cons you've played. It's quite simple that if you don't go back up to my house with the car and jewellery, then I'm sending all your details to the cops. You have 90 minutes to get there," I declared. "And then you can remove your heap of scrap from my driveway!"
"You win! Let's go," Clay said reluctantly heading back over towards the Camaro. He took off all the jewellery he was wearing and handed it to me.
"By the way that outfit you're wearing has given me a raging hard on Catherine," he declared. "I deserve to be punished by someone who can make looking like a dominatrix a fashion statement."
"Good to know. Then I shall take great delight in punishing you," I replied and I got back into the Ferrari with a big smile on my face. I'd emerged from the darkness and had regained full control. The fairer sex had won again.
As he pulled away I was just tempted to follow him back to the house, but the Ferrari was so much more fun to drive quickly. So I just went past him on the first straight and headed back leaving him well behind. I got back fully 10 minutes before him and was sitting on the wall beside the open garage door when he finally arrived.
I pursed my red lipstick coated lips and headed into the house. I pulled a bottle of Bollinger out of the fridge to celebrate. When he arrived in soundly defeated I pointed to the bottle and ordered, "open it!"
"Why should I?" he declared.
"Because I don't want to chip a nail or break one Clay," I replied. "Pour yourself a glass too before you leave."
Before long we were sipping the champagne which was chilled to the correct temperature.
As I drank my champagne, I thought that perhaps I should take the opportunity punish him severely. For that he would need to see inside my basement. I could easily strap him to the cross and then flay the skin off his back with my whip. It would be such a shame if I'd accidentally killed him.
Then I remembered the sex from the night before. I'd noticed he was blessed with an almost total absence of body hair. I detested hairy men and his genitals were certainly big enough which obviously I would no longer enjoy if I cut it all off. With the Camaro parked up safely in the garage, I went into the kitchen to pick up a carving knife.
"Why are you holding a kitchen knife?" he asked.
"I was thinking of cutting up smoked sausage for lunch," I replied. "Did you put any fuel in my car on the way back?"
"Yes, I did. I put back what I used," he replied. "I see you're still wearing the jewellery."
"Yes, I am. It's my favourite pieces that you stole."
"It looks way nicer on you than it did on me," he said.
"Thanks I've had more practice wearing it than you. Perhaps you could start a new trend of men wearing stolen women's jewellery?"
"Oh right yes I feel like I can totally pull that off," he laughed.
"Totally you could," I replied.
"Like why can't men wear women's jewellery stolen or not?" he asked.
"Well I'm a man and I wear it all the time," I replied. "So yes why can't they?"
"The big difference is that you don't look like a man to anyone who sees you though Catherine," he replied.
"Yes so I'm told," I replied. "That's a very good look to have at times. I'm very proud of that Clay."
"So do many people know your little secret?" he asked.
"You mean about being a transsexual?" I asked and then added when he nodded. "Not really no," I said wondering what he was asking that for.
"Do you think that your company directors would like to know that you're a tranny?" he asked.
"I doubt that they would be best pleased to know what I really am," I agreed.
"Perhaps I should tell them then. Kind of put them out of their misery so they know exactly what you are," he replied.
I decided to ignore his comment. "I'll make two plates of salad if you'd like to wait in the dining room, I will bring it in to you," I said.
"That would be very nice, thank you," he said taking his glass of champagne and the bottle as he walked into the dining room. He looked out of the window until I arrived with everything on a tray. "Here let me help you," he said taking the tray out of my hands. Once on the table I put the food onto two plates and poured more champagne into our glasses.
"Please help yourself to bread. I picked it up fresh at the deli today after the gym," I replied.
"That outfit you're wearing really is on the next level Catherine. You do make an incredibly sexy woman," he said sitting down and taking a napkin. "All I can think about is pushing my hard cock deep into your openings. I just wish you had a third one though like a normal woman."
"Thank you," I replied taking the seat next to his. "I don't have any plans for that."
"All right, so I brought your Camaro and jewellery back. Can you delete the information you hold on me now?"
"Nope," I replied smiling at him.
"Please can you delete it now?" he asked thinking he had to request it nicely and so added a, "Thank you."
"Nope," I repeated.
"I thought we had a deal?" he said.
"I'm not bound by any code of ethics, Clay and apparently neither are you. You are the one who stole from me remember even though we were fucking great in bed," I said.
"Yes we did some amazing stuff last night," he admitted. "That's beside the point. All right, you promised me that if I brought your car back you'd delete the information," he said anxiously.
"But Clay promises are made to be broken," I replied but he then lunged towards me. "Don't you dare ever hit me."
Instead he reached out and touched me gently on the shoulder and said "tag."
I used my fork and tried to stab his hand with it. I was successful.
"Oh fuck that really escalated," I said seeing blood oose out of four small wounds on his hand. "I'll get you a band aid."
"I'd ask if you were on your period if you behaved like this but then women like you don't have periods," he said wrapping his paper napkin around the holes.
"No I wouldn't get a period even if I had my gender change," I replied. "I don't have the plumbing which is a big plus. I can still be a bitch though."
"What about you delete the information you have on me and I don't tell your company that the CEO is a tranny?" he then said after a brief pause. I went to the kitchen and came back with the first aid box. I tried to undo a band aid but my nails made my attempt impossible.
"You should cut those long nails of yours Catherine. Though I do like to see you wearing them long and red like that," he declared opening the wrapper and applying a band aid himself. "See how easy it is?"
"Yes I see," I replied and watched him get up towards the wine rack. He studied all the bottles and picked up one.
"Fuck! Oh my God, what are you doing?" I asked as he opened it.
"Well I was thinking this might work instead. You being a materialistic bitch," he said heading towards the living room.
"The label says that this is a Chateau Lafite. It is inky burgundy in colour, it is a full-bodied vintage that is moody, complex and dense, fragrant with notes of chocolate, cedar wood, sandalwood, black tea and banana, it has an alluring whiff of mahogany and creme de cassis which pulls you in deep to its black currant centre. The beautiful tannins and intense cocoa beans are palpable too so this could be a calamity," he said reading the label on the bottle and standing beside my white sofa. "I will Chateau Lafite the fuck out of this sofa!"
"You wouldn't dare," I replied annoyed. "The Lafite is very expensive wine and that sofa is Italian. It had an eight-month lead time and cost me 70 grand. Please think carefully about what you're doing," I replied.
"Catherine have you ever wondered if there was something better you could spend your money on instead of wine and furniture?" he asked.
"Well no, I can't say I have. I mean like what else should one spend money on?" I asked.
"How about a charitable foundation for drop out mechanical engineering students perhaps," he smiled. "Or go and get your sex change too."
"Yes but you should know by now I'm a self-serving, materialistic, narcissistic, sociopath, Clay. I mean a charitable foundation is not exactly in keeping with my character," I replied. "As for the sex change you can forget that."
"Damn! No you're being really hard on yourself, Catherine. I don't think you're any of those things. I think you're a really wonderful girl or would be if you had a sweet pussy between your legs. You should really work on your self-esteem. You really are so sensitive and sweet sometimes," he declared.
"You know, I do try," I said as he hovered over the sofa with the bottle open.
"Do we have a deal then?" he asked.
"We have a deal Clay," I replied taking out my phone. "Put the bottle down first okay."
He stood back and I started to play with my phone. "All done see?" I replied showing him the phone screen.
"I can't see it from over there," he said coming round. I got up and met him in front of the sofa and sat down. I invited him to sit beside me. "Let me look."
He looked and I saw him smile. "Thanks Catherine."
"You're welcome Clay," I replied.
"Of course I could still mention to the board members of your company that you're a tranny, a sissy boy, a chick with a dick, who loves it in the ass and gives it in the ass too," he said getting up to leave.
"Stay there," I said. "Don't move! Don't fucking move, okay?"
"Sorry but I'm leaving," he replied. "You have your car and jewellery back. Let's not let this escalate any further."
"Clay I kind of feel like it's already escalated. I mean you stole my things and I think that's textbook escalated," I replied. "Now you're threatening little old me with blackmail."
"You're right, but there's no need to escalate this to the point of no return," he said. "I think we should be adult about this."
"I hate to be a party pooper Clay but I kind of feel like we're there already," I said.
"I'm inclined to disagree. All right I'm sorry I stole your car. I'm sorry I stole your diamonds; those were prick moves. I'm sorry I ever came to your house," he confessed.
"You're not sorry about last night though," I replied.
"True I'm not sorry about the epic sex, but for everything else I'm truly sorry," he said sounding apologetic and sincere. "Why don't we just pretend we never met, okay?"
"Sure, okay," I said. "The trouble is we can't just forget that I came while fucking you in the ass."
"Yes that's going to be hard to forget that," he agreed. "It hurt like hell at the time too. My first time ever having a cock in my ass."
"Strange it was my first time too having my cock in your ass," I replied thinking he would see the funny side. "Maybe we should do it again just to make sure."
"Sure of what?" he asked.
"To see if it still hurts like hell," I replied. "Maybe you'll find it won't hurt so much next time. Besides it might be useful to learn how to relax doing it, if you ever end up in prison Clay."
"That's funny Catherine," he declared laughing. "I'm not going to prison now you deleted all that stuff on your phone. You did delete it didn't you?"
"It's all gone you'll be glad to know," I said getting up. "I feel a change coming on now this leather gear is no longer needed. So relax I'll be right back."
I walked quickly into my bedroom, sat down and gratefully pulled off the boots which were killing my feet. I quickly disrobed, brushed out my hair and applied a thick creamy coat of red lipstick to my lips. I opened up my closet, pulled out my navy blue pencil skirt dress which showed off lots of cleavage. I found a pair of seamed stay up stockings, black thong panties and a push up bra and so put them on. I put the matching pumps on the ground and stepped into them before pulling up the dress. I was out in five minutes struggling with the rear zip.
"Be a dear and zip me up," I asked as I approached him turning to proffer my back.
"Gladly," he said pulling it up. "That's another knock out dress Catherine, have you got a cocktail party to go to?"
"We are the party baby," I laughed crossing my legs relishing the feel of the sheer nylons on my legs.
"I admit it you're a really beautiful woman and you're very rich," he said. "You fascinate me."
"Thank you because you fascinate me too," I replied. "I've been thinking."
"What have you been thinking?"
"Thinking about you Clay mainly. When I got changed I didn't just think about what I was going to wear that would please me but about what I would wear to please you too," I replied. "So the way I see it I'm fulfilling two important things by pleasing you and me at the same time."
"Yes I see that," he said. "I do find you attractive Catherine. I can't deny it. I just wish you didn't have a cock."
"Well I really liked the look of your cock Clay. It was lovely to suck on and to feel it inside me," I replied. "Did you know that I fancied you from the first moment I saw you?"
"Did you? I was the same. I couldn't believe what I saw when you got out of the Ferrari yesterday."
"I do think I should do what you suggest and start a charitable foundation. You do know it costs Californian taxpayers thousands of dollars to house an inmate in prison for a year. If I made sure you stayed out of jail, then we'd save the state a fortune." I smiled and saw his reaction then added. "I mean that's a lot more than the tuition for a mechanical engineering student."
"With plenty left over for pizza and beer," he replied.
"Exactly," I replied.
"Maybe you should treat yourself to that final surgical procedure too Catherine," he replied. "I don't think that there's a place for two penises in your bed."
"Oh I am sorry you feel that way," I replied.
"Well you kind of said it yourself, that mine is perfect while yours is not so impressive these days. Maybe all those female hormones you take have had a bad effect on it?" he asked.
"Yes ok but I love standing up to pee," I replied. "I'd miss that if I had it chopped off."
"It's no big deal," he replied.
"No big deal for you no doubt but for me it is," I replied.
"You shower a lot so you could do it in the shower instead," he said.
"That would be hideous," I replied. "A shower stinking of urine."
"Yes you're right leave it as it is and I will just go and get on my way back to the world I know," he said about to leave.
"Oh that means you'll be stealing from old people again Clay, including sadly my dear maternal grandmother by the way." I replied making him sit down again.
"Which one was your granny?" he asked.
"You took her life savings from the kitchen. Does that ring any bells?" I asked.
"No well we have done lots like that," he said.
"You don't remember her? Her name was Elisabeth Sharp. You called her Betty, she had a pink hair rinse and you cleaned her out. It took a while to get you to answer my advert but in time you did and now here you are," I said.
"Wait she was your grandmother? Is that why I'm here?" he asked seeing why he was in my house.
"Initially it was yes," I admitted.
"Well for what it's worth, your grandmother was a really nice lady and I'm sorry now that I robbed her," he replied.
"She still is a really nice lady, Clay and I'm inclined to think that stealing from a lovely elderly lady
is exceedingly fucked up," I replied.
"Well what can we do to resolve this Catherine?" he suggested. "God, I'm thirsty, I'm getting that cotton mouth kind of thing, I'm dehydrated. Can we take a water break?"
"Yeah, that'd be nice. I'm quite thirsty too," I replied.
We drank in silence. Then he spoke, "If I remember I took about 3 thousand dollars from her. Perhaps I could pay her back?"
"I already gave her money," I replied.
"That was sweet of you Catherine." He said. "Does she have a problem with you being a tranny?"
"No she actually helped me with it when I was younger. When I stayed with her during the summer she would let me wear all her clothes." I replied.
"That's cool then. I can see why you would love her so much," he said. "I don't have a problem with you being a tranny. Well all right just one problem."
"I want to believe you, baby, I really do," I replied. "But you haven't exactly established yourself with a passion for honesty in your life."
"So tell me one thing, why the sex last night?" He asked. "If you knew I robbed your grandmother why go to bed with me?"
"That really was just for fun. I mean you're very sexy and you really liked sex with us. So why put that to waste?" I asked.
"You think I'm sexy?" he asked. "No one called me sexy before."
"Oh God yeah. Yeah, you're very sexy," I replied. "Particularly when you did me in the ass with my toes pointing the ceiling. I never felt more feminine than I did then."
"I'm flattered," he said.
"You know you've got it baby," I said sipping my water.
"Well yeah, but I mean it's nice to hear it sometimes," he replied.
"I even liked you enough to let you go this morning which trust me I've never done before. I wasn't even going to turn you in to the cops when you stole my car." I said seriously. "I wasn't even gonna call the cops when you brought the car back."
"That does speak volumes about your forgiveness or the size of my manhood. I think it's probably the latter. Am I right?" he asked.
"Yes you are right. I never had one so big inside my mouth and inside my ass before," I replied. "Maybe it would be a waste sending that to prison."
"Your mouth was great but doing it in the ass isn't exactly my cup of tea Catherine." He said. "I've always liked pussy fucking better. It's much less messy and it reaches the right spots in a woman. I still think you should go to Thailand and not just to visit Tukta."
"Oh you have a pussy fixation Clay," I said. "Does that mean you won't stay until I get one? Come on, I know you've got a soft spot for me."
"What well yes I do but then it would be perfect don't you think?" he said.
"Perfect for you maybe. Not so perfect for me," I replied. "I've heard all those stories of transsexuals being unhappy when they cut off their cocks, they can't get orgasms for months after it and it hurts like hell. I mean it really fucking hurts Clay."
"Yes but wouldn't it be worth it knowing you're truly a female and you have my hard cock desperate to fill you up every chance we got? Oh my God, that makes me hard thinking about it," he said.
"I'm not very good with blood," I replied. "Especially my own blood."
"You'd heal up quickly though. I can tell you're a quick healer," he said.
The truth is I really absolutely adored Clay but I wasn't about to lose my pleasure centre just yet. It might be an option in the future but not right now.
"Well if you can't do it, I'll head off then Catherine. It was nice knowing you," he said.
"Wait are you saying you won't stay unless I have a sex change surgery?" I asked.
"Yes in so many words," he replied.
I was lost for words and then said, "We'd make a cute couple if I did get one. Would you want to get married?"
"We are so damned cute," he said. "Yes I'd marry you Catherine and really make a proper woman out of you if you'd let me. I can't think of anything cuter than you with a fully healed up pussy and my cock moving in and out of it all night long. Maybe even have you sleeping on top of me with my cock buried inside you."
"You are obsessed," I replied.
"Just think adorably cute Catherine. You'd be that cute wife I always dreamed about," he said. "There would never be anything cuter in our life."
"Would you care to dance?" I asked.
"I should be delighted to dance with you," he said smiling. "Did you ever stop to consider that me leaving here would be an absolute waste?"
"Actually I have been thinking about it the last few minutes. If I go to Thailand will you come with me?" I asked.
"Sure I'll hold your hand all the way," he said.
"To be honest I even thought about it a great deal while we were making sweet, sweet love last night. I really wished I was complete and that you being inside me would make me completely female."
"Yes and I'd adore you as my female Catherine," he said. "You're the most special girl I've ever met. I can't breathe when I think about not being with you. I mean I know we're an odd fit but I really think we can make this work. I mean why can't we?"
"It will mean sacrifice for you and me," I replied.
"Your sacrifice is nothing compared to mine," he said. "You are almost there. I have to go back to college and get my degree. I then have to get a job and make an honest living. You make me want to be better baby, you make me want to be a better man so I hope you want to be a better woman."
"I think we're meant to be together," I said. "I think my sacrifice will be bigger though as I'll need to support you through college, get my cock inverted and keep my company going."
"I know it. Catherine I love you," he said.
However, I didn't reply as I was suddenly on the phone to Mitch to find out what he thought of our takeover.
"It's a good deal Catherine," he said.
"That's fine then, let's talk on Monday," I replied. "Thanks for the call."
"Catherine we are talking about starting a relationship and what it would take and then you go and talk business," Clay asked. "Here I am ready and committed to us and you go off and talk about business."
"I'm sorry," I replied.
"I'm so disappointed," he said.
"You're right. I apologize. It was selfish. What can I do to make it better?" I asked.
"You already know what to do," he said.
"Go to Thailand?"
"Correct," he said.
"Oh baby... of course I'll go and do it," I replied wondering why I was agreeing to something like that so eagerly.
"I really appreciate that," he said. "I just want to be a good man so you can be a perfect ten woman."
"Tell you what? Let's even the playing field let's get married," I said.
"What, get married now?" he asked. "After you get back we should."
"Fair enough," I agreed and added. "When I'm healed up we can fuck like rabbits, raise some adopted kids and live happily ever after?"
"Fuck it. I'd do anything with you," he said kissing me on the lips and I wasn't annoyed that he smeared my lipstick.
Six months later and we have an extremely chilled out lifestyle at my large mansion. During the week, we wake up late and I work from home most of the time. I've completely healed up from my Thailand trip so we can make love properly whenever we want. I love it when he penetrates me in my new pussy and although I have yet to get an orgasm, it drives me wild to see him all the way inside me. I am Mrs Catherine Reid-Mitchell now married to Clay Reid-Mitchell who is a hard working second year student studying mechanical engineering and who also works in my company and is definitely on the way up.
We're happy because we remember that we are us and our lives together are just incredible. And while he loves having the benefit and enrichment of my earnings, he's very enthusiastic about graduating, rejoining the workforce and climbing up the corporate ladder.
At around eight a.m. we get on our Peloton bikes and take our favourite class with Kathy together. Although I hate it my ass has a lot more padding now as he likes to have a cushion against him pushing into me.
The end.