The Path to Happiness Pt. 10

As I stood looking at myself in the mirror dressed in my bridal gown, just over my shoulder Becky was looking beautiful in her bridesmaid dress as she fussed with my veil. She had aged well, and looked great for a woman in her early 50s. I mused we had both aged well, like fine wine, I thought to myself.

There was a knock at the door and a young girl dressed the same as Becky entered. The 15-year-old smiled at me as she approached.

"Mum, Dad is here and ready to Go." She spoke.

"Thank you, Sarah," I said to my daughter.

I turned to my mum; she was busy playing with her hat.

"Ready Mum"

"Yes dear," She replied.

I turned back to the mirror and my mind drifted back through time where my journey had begun...

The Week following the photoshoot was hectic. I had lectures, shifts at the restaurant and preparations for my New York trip. Stephen took me out on another date, this time to the cinema. I decided to take it slowly with him and not jump into bed with him. Though I found this very difficult. We did share a kiss as he dropped me back to my flat.

The night before my trip, I spent the evening packing my suitcase. I also had a long chat on the phone with Becky who was having her first surgeries whilst I was in the States. I felt guilty I would not be there for her, but she reassured me Alison would take good care of her. After the call I hit the sack for an early night.

My blissful sleep was interrupted by the blaring of my alarm clock. Why did all flights take off so early? So, at 4.30am I got up and showered. When the car came to collect me at 5.30am I was looking pretty good in my business attire. The uniformed chauffeur took my case and placed it in the boot of the Mercedes. Richard my client was waiting in the back of the car.

On the drive to Heathrow, he was all business, going over all the details of the trip. Most of the trip he had several meetings setup, as well as dinners in the evening to network with his clients. It turned out he was in to arrange high-cost financial loans between large corporations and the banks. I was pretty good with numbers so I followed along with his explanation.

As we hit the M4, Richard put his hand on my stocking covered thigh and gave it a squeeze. He told me he would like some pre-flight relief. I knew I'd be used for his sexual gratification during the trip, but I thought he'd wait till we were in New York. Never mind I mused as I opened his trousers and fished out his cock. I leaned down and licked his head, and sucked him into my mouth. He told me to be quick as we were only a couple of junctions from the airport.

I shoved my hand into his pants and cupped his balls as I bobbed my head up and down his hardening shaft. His moans told me I was hitting his right buttons. Feeling a little naughty, I pushed my hand passed his balls and pushed my index finger into his rosebud. His eyes widened as I sank my finger deep into his arse. Bingo, I found his prostate and he lost control and fired his load into my mouth.

I pulled my hand back out his trousers and let his cock drop from my mouth as I swallowed his load. His face was flushed and I was worried he might have a heart attack on me!

As he regained his composure, he closed his trousers as we approached the terminal at Heathrow airport. As the car pulled up curb side of the VIP lounge, I had just finished touching up my makeup.

The driver opened the door, as a porter collected our bags. After a quick checking and expedited security checks we were led in to a lovely lounge far away from the general public. We shared a champaign breakfast until we were called to board our plane.

Thanks to the wonder of engineering that was Concorde, 4 hours later we were checking into the Waldorf Astoria Hotel on Park Ave. Richard had booked a suite and I was surprised to see I had my own room. I thought I'd be sharing his bed. When I quizzed him about it, he told me that I might be called upon to entertain one of his guests in there. So, he was happy to pimp me out to win business. To be honest this whole trip I was his travelling whore so who did it matter whom I slept with.

With the time difference it was 4.30am, Richard said the first meeting was at noon so I could go catch up with my sleep. I went into my room and stripped to my underwear and went to bed, it did not take long for me to drift off to sleep in the king-sized bed.

The phone buzzed a few hours later, it was the front desk with my wake-up call. Richard must have arranged this. I checked the clock and it was 10.30am, I had 40 minutes till we had to leave for the first meeting.

20 minutes later I just put the finishing touches to my makeup after a quick shower to wake myself up. As I slipped on my pinstriped jacket there was a knock at my door. Richard called out that he had ordered some coffee and toast.

I took one last check in the mirror before declaring myself ready.

I joined Richard for brunch as he explained who the clients, we were meeting are. They are a multinational restaurant franchise company, and they were looking to expand into the UK. Richard had already secured interest from a UK based food chain to take on the UK roll out of the US brand.

After we ate, I grabbed my notebook and pen to take notes of the meeting and Richard put the presentation slides into his brief case.

A black town car was waiting for us downstairs, and the driver took us downtown to lower Manhattan. I could not help but stare out the window as we passed the famous New York landmarks I had only seen on TV.

After the car dropped us off, we were met kerbside by a woman in what could only be described as a power suit. The shoulder pads were very extreme, and her makeup was applied more as a war paint. Clearly, she was out to battle in the male dominated industry, and I guess she usually won.

She introduced herself as Tiffany Barstow, Junior VP for foreign markets. She ushered us straight pass the security desk and in to an express elevator. On the ride up Tiff informed us that Brad Frederickson was waiting for us in the board room.

When we exited the lift Tiff led us through an open planned office where men and women dressed in power suits frantically barked into phones whilst looking at mono screen computer terminals. It was all like a poor knock off of the film Wall Street.

The Wall Street theme continued when we entered the board room and we met Brad. He was Gordon Gecko personified. Balding slicked back hair and overweight, but the sharp suit, with red tie was a business cliche. Probably back in the 80's he looked like Michael Douglas. I'd say the years of excess had not been kind to him.

Tiff made the introductions, and I felt Brad's clammy hand when he shook mine. I could also feel his lecherous eyes checking me out. It was at that moment I had the sinking feeling that it was Brad I would have to "entertain" for Richard in my room.

Richard jumped straight into his presentation. I had to alternate between taking notes and changing the slides on the overhead projector. The meeting went well, but I could not help but feel Brad's eyes on me. I could also feel some hostility from Tiff as she was in her mid-30's and she felt threatened by my youth.

Brad and Tiff left the room to have a private discussion whilst I started to clear our papers away. Richard came up to me and said I was doing a great job. But tonight, we were going out with Brad and Tiff and I was to be "nice" to him.

When Brad and Tiff returned, they brought the contracts with them. After they were all signed Brad brought out a bottle of whiskey and poured us all a glass. Technically as I was 18, I could not drink in the US but Brad thrust a glass in my hand.

The mood in the room relaxed now that the business was done. Brad and Richard started to talk sports. Tiff came up to me and asked me how long I had worked for Richard. I explained that I was only temping for him as I was a full-time law student. She had also studied law so we chatted about that.

A young girl came in and reminded Brad he had another meeting in a few minutes, so he and Tiff left. The secretary led us back out of the building and our town car was waiting for us.

The car took us back to the hotel. The whiskey had started to hit me as I looked out the window. Richard called to me snapping me out of my daze, he told me we had a few hours till we go out for dinner. I was hoping to grab a bite to eat and have another nap, but when Richard put a hand on my thigh, I knew I would not be getting much rest this afternoon.

Back at the hotel we headed to the restaurant for lunch. Richard had a glass of wine but I stuck to water. In the lift back up to the room, Richard cupped my arse. Though I was not in the mood for sex, my arousal started to stir.

Once in the room, Richard pulled off my clothes and soon had me naked. He loosened his tie and opened his shirt collar. He led me over to the sofa and bent me over the arm. He parted my cheeks and spat in my hole. He started to work his fingers in me and was telling me he was going to wreck my boy pussy.

He pulled his fingers out of me and I heard his zipper, as he fished his cock out. He pushed into me and started to grunt as he fucked me. I had hoped he had used some more lube, but his pre-cum started to grease my anal canal.

Richard grabbed my hair and pulled my head back roughly, calling me a dirty sissy whore.

He was clearly reverting to his dominant role in sex. His thrusts were short, but hard. This was definitely a fuck, pure and simple. My own cock had also grown to full length, and the fabric of the sofa was very stimulating as my cock rubbed back and forth on the sofa arm.

Unfortunately for me Richard gave out a loud grunt and unloaded into me. He collapsed on top of me breathing heavy. Has he recovered his hip twitched and made small thrusts into me as he recovered from his orgasm.

After what felt like ages, his cock plopped out of me and he got off me. As I stood up my cock was sticking straight out. Richard saw my cock, and reached out and grabbed it. Using it as a lead, he led me to the sofa and pushed me down on to it. He knelt in front of me and licked my shaft. He then swallowed me as deep as he could. He started to bob his head on my knob.

I closed my eyes and leaned my head back on the sofa. Richard coughed, and as his throat opened the head of my cock slipped into his gullet as he deep throated me.

That was it for me and I lost my shit and fired into his throat. Richard swallowed my load as I fired 3 thick ropes of cum into him. As he let my cock out of his mouth, he licked the last drops of cum off my slit.

Richard stood up and wiped the corner of his mouth and told me he would see me later, and left the room. I was out of breath, so I pulled the throw from the back of the sofa and wrapped it around me. Within a few minutes I was fast asleep.

Richard tapped me on the shoulder to wake me up. As I came too, I could see he was dressed in a new suit, more casual with a lighter colour and blue shirt without a tie.

He smiled and said, "hey sleepy head, time to get ready for dinner".

I looked out the window and the sun was setting. As I got off the sofa, I felt a damp patch under my butt. Richards cum had leaked out as I slept and pooled under me.

Back in my room I used a tissue to clean out the remains of Richards issues from my arse.

20 minutes later, I had reapplied my makeup and fixed my hair. I slipped on some black underwear with sheer black stockings. I topped it off with the crimson dress Chris had brought me after our he took my virginity.

Richard gave me his approval when I entered the living area of the room. I put a black wrap over my shoulders and grabbed my clutch purse.

Our town car took us to Le Bernardin, down midtown Manhattan. Richard held his arm out and I threaded my arm through his as he led me into the restaurant.

Brad and Tiff were already at the table when we walked in. Brad was still in the same suit as earlier, but Tiff was wearing a dark blue gown. They rose as the matradee escorted us to the table. Brad held my chair out for me as I sat.

Dinner was casual, and I had the best steak in my life. The only issue was Brad's hand had wondered under the table a couple of times, and rubbed my leg. It almost put me off my food.

I stuck to water as I was clearly under 21, but the others downed a couple of bottles of wine as well as brandy at the end of the meal.

Richard invited them back to our room for more drinks.

Back in the room Richard passed me a glass of wine and I drank it quickly as it dawned on me, I would soon be having sex with Brad. I have had sex with several men in their 50's and even 60's but Brad was no turn on for me with his sweaty overweight body, and he smelled.

My worst fears came true as his hand wondered under the hem of my dress. I caught sight of Richard who nodded at me that was to let Brad play with me. He then started to kiss Tiff.

I downed my second glass, and Brad started to kiss my neck. I could smell his breath and I nearly lost my dinner. Brad was roughly groping my left breast, every fibre in my body wanted to push him off, but I was a whore I had to suck it up. I just hoped he would come quick and get it over with.

I glanced over at Richard, and Tiff had his cock out and blowing him. Brad moved my hand to his crotch and I did not feel anything. Brad pushed my head towards his crotch, for the first time I engaged Brad, and opened his trousers. I pulled out the most pathetic excuse of a cock I have ever seen. It was about 2" long and flaccid. I tried to stroke some life in to it, as he pushed the back of my head towards his worm. His fowl musk was worse and I did gag as I took his dick into my mouth and sucked.

It took a lot of effort to get him to firm up, but he finally grew to a whopping 3.5 inches.

Tiff was bucking up and down on Richard's lap, she had lost her dress and was naked except for her stockings and heels. Brad had started to pull the zip of my dress down, so I let go of his cock and stood up and shrugged my dress off. I followed this with my bra and panties.

Brad licked his lips, and pulled me onto his lap. His mouth lapped my nipples, and they did react. I decided to try and get him to the end so I knelt on the sofa and presented my arse to him. He lined up behind me and pushed into me. He panted has he fucked me, but I could barely feel him. Bless him he was giving me his all but it was officially the worst shag I had. Not to be rude I pretended that he was good and big and to pound me harder.

Richard and Tiff had swapped positions he was on top of her pounding her pussy. Brad had slipped out a couple of times, I did my best to encourage him. He pulled out with a grunt and blew his load over my lower back and arse. He grabbed my hair and forced me back to his crotch telling me to clean him up.

I took his shrinking cock into my mouth and licked it clean. Brad finally let me up and told me to get him a drink. I poured him a whiskey as Richard fired his load over Tiff's mouth and face.

I handed Brad his drink, and he told me to clean Tiff up. She stood and our mouths locked as I scooped Richards cum out. I also licked around her face, and then fed her his seed.

My cock started to grow and it pushed against Tiff's pussy. She pushed forward and I entered her. I perched her arse on the edge of the table, and started to pump my cock into her. Brad and Richard were enjoying the show and for the first time this evening I was starting to enjoy myself.

Tiff wrapped her legs around me as our tongues fenced between our mouths.

Tiff through her head back as she came and I was soon to follow suit filling her pussy with my sissy seed. The legs locked me into her as she had a second orgasm.

I caught a glimpse of Richard looking a little sheepish as he had not gotten Tiff off.

When we recovered Tiff let me go and started to dress, but I just grabbed my drink. When she was redressed, they said their goodbyes and left. Brad put his arm around me and kissed the nape of my neck telling me I was fabulous. He patted my arse and took his leave to his room.

I had a quick shower and slipped on a nightie and went to bed.

The next morning, I was up and dressed before Richard. I had gone for a pin striped skirt suit with a white oxford blouse. I was just pouring the room service coffee I had ordered when Richard emerged from his room. He was suited and booted ready for another day of business.

Over breakfast he complimented me on my performance last night. I gave a coy smile, but I told him Brad was a real struggle. He laughed and admitted the man had a serious personal hygiene problem. With that we both burst out laughing.

Richard informed me today's meeting was a potential client looking for some finance to expand their business into the Asian markets. It was an escort agency that caters to individual fantasies.

Most Japanese men had sexual fantasies for girls in school uniform. I laughed and said I knew that market well. Richard gave me a sideways glance and I explained that I have dressed in various uniforms to please clients. I even told him I dressed as a schoolgirl for a couple of porn movies. I could sense he was getting aroused so I thought I'd better stop explaining my sexual exploits before I got more than my bacon and eggs for breakfast!

I went to my room to fix my makeup and grab my bag. When I came out of the room Richard was on the phone, our car was here. He grabbed his brief case and we headed down to the car.

As we drove out of Manhattan across the bridge to Brooklyn, I lazily stared out of the window. Richard spoke to me breaking my idle sightseeing.

We were booked on the first Concord out in the morning, but if the client took a shine to me, I would be required to please him. I said OK, I'm sure it could not get any worse than Brad!

We pulled upto a small office complex, and Richard and I headed into the reception. Richard announced we had an appointment with Mr Takagi. The girl on the desk pointed us to a waiting area whilst she called upstairs.

5 minutes later she called us back over and told us to take the elevator upto the 4th floor where we would be met.

We were greeted off the elevator by a young Asian man dressed in a black suit with white shirt and black tie. He introduced himself as Mr Wong with a slight bow. As he led us to the small conference room, I noticed the walls were lined with pictures of girls in various costumes ranging from School, airline and police uniforms. To black leather clad dominatrixes.

As we entered the room an older Asian man, in his early 40's rose from his chair and bowed as we approached. Mr Wong introduced him as Mr Takagi, CEO of Fantasy Fulfilled. Richard bowed and I followed suit.

Soon the meeting was in full swing as Mr Takagi explained the services his company offered. It was basically a specialised escort agency where the client would specify a particular request. They did not offer sex, but if the escort wanted to make their own arrangements, then that was up to them, he said with a wink.

Richard launched into his pitch about how he had loads of potential investors for this service in the Pacific rim. And how this business would thrive in that market area.

As the details of the business were being discussed they only offered a private date with a girl in costume. I chimed in and said they could also offer a stripper and kissogram service. I explained these were also lucrative to the agency and the girls. I also mentioned that they could expand their portfolio to boys and T-girls.

Mr Takagi looked at me with a long stare. For a second, I thought I might have spoken out of turn. But his face broke out into a large smile, and asked me to continue.

For the next 20 minutes I went over the business model I had worked for in the UK. I even let it slip that I was a T-girl and I was popular with the male clients. At first Richard seemed annoyed I had hijacked his meeting but soon smiled and realised I had helped land this fish.