Derby Day Surprise — Chapter 5
By Julie D Cole

As I looked around the place was half full. What a strange experience to be in this wonderful tearoom that was nothing at all like Bettys tearooms in York, Ilkley and Harrogate. No waitresses in black uniforms with little white aprons and no dear old ladies chatting away sipping tea out of a saucer and nibbling on a ‘Fat Rascal’ or a cucumber sandwich. This was bliss. Such a beautiful place with very friendly waiters. Maybe they were so friendly because they had the odd sip of Vodka on the side. I’d been told New York waiters weren’t the friendliest in the world.

Carole was very kind and played ‘mum’ pouring my tea and I told him to put the milk in first to avoid staining the china cups. Good old mum. She always says that. He offered me the first choice of cakes. I could get used to this attention and I selected a nice Chocolate eclair. Normally I’d stuff this straight in my mouth and something inside me slowed my action down and I put it to my lips and licked the cream with the tip of my tongue. I hadn’t meant anything provocative but my sense of humour took over. Carole was speechless and I saw him adjust himself under the table. I took a small bite and let the chocolate melt on my lips. Stef was grinning and so I realised I might draw attention to myself. I licked the chocolate from my lips. Mmm, the combination of chocolate and lipstick was delicious.

The danger was I was becoming a little bit too adventurous and I must have been flirting a little bit too much because Carole because he moved alongside me onto the couch. I tried to edge sideways but not much chance to move with cushions in the way. I decided to decline any more drinks except tea and luckily Stef saw that I felt a bit threatened and offered to show me where the restrooms were. I almost jumped over the table.

Carole just moved his legs and didn’t stand up to let me pass. I had to squeeze past him and it was obvious that he’d done it on purpose. My hand brushed against him and I realised I’d gone too far. His knapkin couldn’t hide his excitement and I had to lift myself up to avoid my butt coming into contact.

‘Nice butt, you should show it off more.’

When we arrived to the restrooms Stef was laughing as she pushed the door open. “Are you trying to get him to explode you minx?’

‘No honest it’s just a bit of fun.’

‘Take care because he’s worked up and he obviously is attracted.’

Stef opened a cubicle door for me and I scurried inside to relieve myself. Mmm nice butt eh? I’ll have to take more care as much as I was enjoying myself. I had wanted to touch him.

Stef was very friendly and watched as I tidied my hair and freshened my lips. ‘You Brits aren’t so tall are you? I hope we can fit you out OK. Why don’t you wear higher heels or wedges? They’d help your butt even more and then old Carole would be putty in your hands.’

‘I don’t want him to be putty in my hands. I hardly know him and we only met today.’

‘Oh forgive me I thought he was treating you and that you’d found a nice sugar daddy.’

‘No way. Whatever gave you that impression. I am not really with him. He is just looking after me and we work for the same Company.’

‘Oh sorry. But take care because I think he has the hots for you already.’

I felt frightened. What if he does make a play. What would he think of me. It’s not like I do this all the time and I’ve been forced to do it. I looked at the girl in the mirror. I did look OK very much and didn’t seem to have any problem convincing either of them I was a girl. Stef looked me up and down and said ‘I will have to lose a bit of weight. I’d kill for a waistline like yours and a bust that doesn’t knock over the flower vases when I turn.’

Well I was at least grateful for the complements that gave me a spurt of confidence so off we went to our table.

Carole paid up and rang for his driver and soon we were whisked away to spend some dollars. Carole showed no sign of leaving us and said he’d be happy to handle the scoreboard as I paraded around.

I had the most fantastic two hours of my life after we reached Stefs fashion store. I was parading around in underwear one minute and out in the store the next walking up and down in front of Carole. He was making me laugh with his expression and his marking. I must have tried on at least 10 dresses and a dozen pairs of shoes before we all decided that my colour was pink. Me in pink!! Steff insisted and I liked the material and the length that was just below the knee. Carole preferred a shorter style to show a bit of leg to our client but was overruled by Stef and I.
Stef selected some heels and a matching white bag and that was the basic outfit and as Carole said ‘our new racing colours for the Derby.’

We selected a variety of more casual clothes and bra and pantie sets as well as a tight skirt and a bright blue blouse and I hadn’t realised until later that this was deliberate to show my nice butt as much as possible if we went out for dinner the day after the Derby.

Carole picked up most of the bags and loaded them in the car. Then Stef produced the hat to match and that was it. All kitted out for $2000 in 2 hours all covered by Carole’s card on Company expenses. I felt a bit of a fraud and yet if truth be known I didn’t really know just how I felt. It seemed to be like a fantasy and that somebody was going to nip me and wake me up. I’d realised that I had a nice pair of pins, at least according to Carole and I didn’t exactly struggle walking in the heels. Something inside me made me react in a most feminine way. Somehow a butterfly had appeared from nowhere and I liked it. What would mum think if she saw me now?

We said goodbye to Stef and she gave me a girly hug. ‘Have a great time and let me know how you go on.’ She smiled and winked and luckily Carole was facing the other way. The driver smiled though. I kissed her lightly on both cheeks. I wished she was coming with us to help me prepare and also to act as chaperone. I hadn’t even met my client ‘007’ yet. I might be in danger of losing my virginity at this rate. Mmm now where did that come from again?

We soon arrived back at the hotel and Carole jumped out to open my door for me. I held his hand and tried to be as ladylike as I could. He patted my butt lightly as he let go of my hand and the driver handed my bags to a porter.

‘I’ll wait in the lobby and make a few more calls. I thought we might pop to an Italian Bistro style place that is less than 5minutes walk and my driver will pick me up later. Is that OK for you?’

‘Err, yes that’s fine.’ How strange that he was treating me like a girl. Didn’t he know?
My first dinner date. I’d better freshen up again and get rid of the vodka breath.

As I passed the reception I saw my friend who’d checked me in and he smiled and waved. I gave him a little wave back. The porter was following close behind me with my bags. Mmm my very own manservant. I was enjoying this and he went left as I went left and stopped when I stopped. My friend was laughing by now.

I fumbled in my bag to find my door key and the porter said ‘Here miss let me do that.’

Miss? Miss, how strange. Still it’s all for a good cause and so far so good. No arrests and no strange looks from anyone. I gave him a tip and quickly freshened up. I’d not felt myself get excited but my panties were a little damp so I had to change. I decided to get some panty liners at the small hotel shop if they had one, before I ran out of panties. As a precaution I quickly washed the two pairs I’d discarded and hung them to dry. They’d probably be OK by tomorrow. The room was definitely looking all girl as I hung the new things in the wardrobe and in the drawers. My make-up bag was in the bathroom along with all the other bits and pieces I’d need.