Derby Day Surprise – Chapter 7
By
JulieDCole
Quick update : Here I am in New York all kitted out to accompany guests to the Kentucky Derby with a business associate who has the hots for me. Nobody has realised I am not the girl they think I am and this is a short term arrangement after my female boss had to drop out at the last minute. I’m right in the deep end and I haven’t even met our client and his wife yet.

I’ve not had any difficulty passing so far and only the hotel front desk assistant manager seems to know my true identity. I’ve been persuaded to switch to a female identity at extreme short notice to maintain a relationship with a key client. I have been kitted out for the Kentucky Derby Day in the corporate entertainment section with an emphasis on a look that would please our key client that is a challenge for tomorrow.

Today I have to manage advances from our USA Sales Agent who is supposed to discreetly accompany me. At the moment he is proving hard for me to handle and I’m in need of some assistance before he explodes.
We came across two German residents of the hotel in a local restaurant, Fritz and Helmut, who coaxed me into the hotel bar for a nightcap now our USA Sales Agent had left.

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I was remarkedly clear headed when I woke early the next morning after a deep sleep. I was glad I hadn’t drunk much of the red wine and had taken care to drink plenty of water.

Having said that I must have been more drunk than I thought since I was wearing the nightdress that had been packed for me and matching panties. I had sworn to myself that I wouldn’t wear them. My wig was hanging on the lamp on the side table. I’d at least left my clothes neatly folded. I hadn’t done a very good job of removing my make-up. I used the toilet and washed my face but the make-up was hardly affected. I needed a coffee so that was my next priority. Somehow I worked out how to use the machine. No sign of any instant coffee or milk but needs must.

I found some make-up remover in my cosmetic bag and set about cleaning my face and then took a shower. My new clothes were still in packages and on hangers where the porter had left them. I wondered what had happened to Helmut and Fritz. I might have had a lucky escape because I suddenly remembered what I’d heard. I wouldn’t have been surprised if they’d tried to spike my drink.

I didn’t really need to shave but I had one anyway just to be safe. Carole might try to kiss me at any opportunity he found and I supposed I needed to do cheek to cheek greetings with our female guests. I sorted out the outfit we’d purchased for me to wear that was appropriate for travel and meeting my client and his wife at hotel. We were booked for 2 nights at The Brown Hotel so we could dine together before the race meeting and then recover before flying back to New York. Then back home for me.
My outfit consisted of lightweight jacket and trousers and a silk blouse. Luckily, I was wearing flats but there was no chance of me passing as male if that was needed. I needed a purse opted for a white panties and bra set and a light blue jumper over the since it was still cool in a morning. I managed to put on a pair of tights without much difficulty having watched the technique used by my first girlfriend who I’d coaxed to stay over one weekend. I opted for sneakers rather than the heels that I wanted to keep scuff free for dinner and the races.

Looking in the mirror was a very effeminate young man or probably a slightly butch looking young woman. I found the inserts that completed my feminine image and I knew it would catch Carole’s attention again. I should probably have brought some pepper spray or even a taser to keep him under control since he was like a dog on heat.

Was this look enough to fool Carole and the airline staff? Without inserts Carole might finally guess but with them inserted I’d have to rely on my identity card rather than my passport and hope that airport staff were familiar with the trans community commuting. The trouble was the two documents weren’t consistent. My identity card had a photo that had been photo-shopped to give me a feminine appearance and it referred to me as Ms rather than Mr. The rest of my details were the same as my passport. I decided it was better to try to split from Carole at check-in and security if it was possible in case I was challenged. Fat chance really. He was like a limpet around women.

I made the decision and inserts were in for the rest of the day. I’d need to carry a bag and I couldn’t use the one we’d bought for the race day. My computer bag would have to do for now and I could buy another bag at the airport if we had time. I had my overnight bag and 2 dress bags to try to accommodate all the clothes I’d brought and purchased. Should I call Carole and ask him to loan me bag or not?

There was a shop in the lobby and I decided to by a sports bag and filled it with my travel clothes and male accessories such as they were. I could leave the bag with the driver and use my holdall and zipper bags. Hopefully, I could drop them as we boarded the aeroplane and collect them as we disembarked.

I felt like I was skating on thin ice and I might need to level with Carole before much longer. I felt calmer after I’d eaten breakfast. A nice plate of scrambled eggs and delicious American bacon with a muffin and lots of fresh orange juice.

I was checking out when Carole arrived on the dot and he came into the lobby to help carry my bags and remind me everything was pre-paid and not to forget my passport. Luckily, I got the same assistant manager as when I checked in who smiled and said to visit again sometime.

First kiss of the day from Carole and first complement logged in. I could get used to this. The latter I meant. Being spoiled was a real treat instead of looking after customers and girlfriends of course.

‘Carole are you alone?’

‘No the driver is here with the car.’

‘I meant where is your wife?’

‘Oh she never comes to corporate events because it makes it difficult for me to circulate and look after customers. I have to look after you as well remember since you are in a strange land far from home.’

‘Oh. Well can we leave a bag with the driver and collect it as I head to JFK on the way home?’

It was no problem, so we headed back to the airport in good time to take the Louisville flight. Carole sat in the front passenger seat and he handed me my travel tickets. The agent had used my security card details when booking my tickets and I felt slightly more confident. Should I tell Carole or not? I was a 50:50 decision between my heart and my head. My heart won.

There was a queue even for business class customers but it didn’t take long to reach the front and before I had chance to consider separate check-in agents Carole took my tickets and security card and handed them over. He seemed to know the agent and he said we would drop the bags as we embarked. The agent looked at me and panic over. She never asked for my passport and she waved us through.

When we passed through security the only comments I got were ‘travelling light Miss? Any spare tickets for the races?” I smiled as coyly as I could and shook my head. ‘Good luck anyway. Back Triple Echo for me please.’

I had no idea about horse racing and no idea which horses would be running nor which were good and which were favourites. I was there for the Company and to ensure my client had a good time.

The flight time to Louisville was scheduled for 4 hrs with me up close and personal to Carole. I was nervous and wished I’d confided in him about my situation and why I had agreed to do it. The problem I had was that I couldn’t justify it to myself let alone anyone else. Four hours seemed a long time. I could travel right across Europe in that time and it didn’t look that far on the map in the flight magazine. I was in the window seat so I was trapped. Could I trust Carole to behave like a true gentleman? How would I behave if a similar situation occurred? It made me realise how difficult it is for women travelling alone or with people they didn’t really know.

I flicked through the magazines focusing on items for sale from the cabin crew and there was a lot of choice for women with a few offers available. Carole insisted to treat me to a necklace and there was no way I could turn him down. It wasn’t as if I would ever wear it or even considered wearing jewelry and this cost him $100. What would his wife think? I opened the gift box and removed it to examine it and he insisted I put it on. Well in truth he insisted to put it on for me. I was feeling humbled and slightly embarrassed to find myself in this awkward situation.

I managed to find the right words to thank him without being over the top. With all this practice I was becoming accustomed to talking in a feminine voice and behaving in a more passive way. After a drink he even let me catch up with some sleep but I suppose that was so he could do the same. He was snoring a little when the stewardess came to check on us and she asked if I was OK and offered me a blanket that I accepted. That was a big mistake because after I drifted off to sleep I was suddenly aware of a hand on my thigh although luckily it was still.

I nudged Carole and moved my leg and tried to sit upright. He just grunted and blinked his eyes as he woke up and feigned embarrassment as if he was dreaming. I knew he wasn’t. He might have had a shock if I hadn’t reacted even though I was tightly packed. I hadn’t had much of an option with the cut of the trousers. They were snug and tightly fitted and I was conscious of showing my panty line when I’d removed my jacket that Carole had placed in the overhead cabin. Not a problem I’d encountered before from this side of the fence.

Carole made some feeble excuse about thinking he was at home in bed with his wife. I decided it was better to keep awake for the rest of the journey and headed to the toilet to keep a distance for 5 or 10 minutes. It worked because Carole behaved for the rest of the journey.

Another driver was waiting as we arrived at Muhammad Ali airport and he guided us to the car park where his BMW was waiting. It was very spacious and comfortable and even though Carole and I sat in the rear seats we had an arm rest between us. The weather was nice and according to the driver the forecast was good for Derby Day. He discussed the arrangements with Carole completely ignoring me even though I was there to look after MY client.

As we arrived at the hotel I was amazed. I thought I was back in England. It was full of character and elegantly decorated and furnished. I was offered a comfortable seat in a nice leather chair and a refreshing drink whilst Carole took care of the registrations. This time I didn’t need to hand over my passport that was a relief and Carole gave his credit card information as security. Our guests had arrived earlier and had taken a stroll down Main Street. We went to our rooms and naturally Carole had organised that we were side by side with a connecting door that I checked to ensure it was locked. I moved a chair behind it in case he had requested a key.