Walking the Path

"Go ahead sweetie. He's pre-lubed and that ring will wrap around your big cock like a warm embrace." She assured me.

I pushed up to his hole and sure enough it gave way. I played around. poking and backing off until I had enough and decided it was time to get to business. I pushed my head inside and I slid an inch or two. Fuck it was hot and really, really tight! It felt amazing!

I put may hands on his hips and began moving in and out, going deeper with each gentle thrust until my balls rested against him. I honestly would've burst if I didn't hold still and collect myself. Like he knew what I was doing, he graciously stayed still and moaned. After a few minutes, I felt the desire to breed this tight ass and began thrusting short and deep. He was bouncing his ass back and now I know why Mr. Jackson moaned so loud when I did that to him... it felt incredible! I increased the lengths of my thrusts until I was at the verge of coming right out. I pounded his cute butt like this for quite some time until Lola encouraged him to move forward a bit more causing his head to go down, and his ass to come up.

"Squat behind him and drive straight down. You'll make him cum in no time!'

The thought that I could make him cum from fucking really spurred me on and, doing as Lola instructed, I was now piledriving into the deepest realms of his bowels, and he was squeaking and moaning like a bitch about to....

"OHHHH FUUUUCCCKKK YYESSS!" He yelled out.

"You got him Sam! He's cumming all over the place!"

Well, that news sent me over the edge, and I was soon flooding the man's ass with a lot of cum. A feeling of euphoria come over me as I squeezed out the last of my cum, making it abundantly clear... I loved fucking!

**

The first few months at X-generation had flown by and in that time, I had made more money than I ever would have made at the old bar in 5 years. I was able to rent an apartment closer to the strip and in a much better neighborhood. I made a lot of new friends thanks to the club. Most of them were girls like me but I did meet some of the guys who worked there and of course I had developed some regulars. Thanks to Lola, not only was I put in a place to succeed but she made sure my oral talents were used on the biggest cocks with the fattest wallets. I became a very popular top girl due to my sexy petite build and a big cock that had developed incredible stamina. I wondered... in some weird and twisted way, if my dad would be proud of my sexual prowess,but I never let myself think like that for very long.

I was just coming back to work from taking a ten-day absence. I bit the bullet early and decided to get breast augmentation surgery. Nothing large, just feminine, and relative to my body size. I suppose I could've gone for the Lopez version, but I decided my sister should be the true benefactor of mom's genes. The doctor Max had lined up was beyond skillful and they looked very natural. I liked them more than I thought I would and everyone at the club was impressed, including Max. While I was now in hawk for 20k, we had come up with a three-year commitment contract and a blowjob. Well, actually I suggested the blowjob, it was more of a thank you than a payment, besides sucking a cock like Max's was all pleasure as far as I was concerned.

"Sam honey, I know you just got back but I was hoping you can pick up a date for me. Nina had to go to the hospital, something about her father, and she was booked with a newbie. I have nothing on this guy other than he's got no criminal record works for a huge financial company. I hate to blindside you, but I'm really stuck."

Blindsides were always a crap shoot, especially if you had your preferences. He could be the exact opposite of what your chosen tendencies are, but you have to act like you're into it. I learned that the hard way when some rich kid figured he was a porn star, destined to top the trannies. A girl could live with that if said porn actor actually had a dick built for it. It doesn't have to be large, but 4 inches was pushing the envelope. All the fakes cry's of pleasure and moans, I felt like I should've been up for an Academy award for best fake sex scene.

"Don't sweat it Lola, I can take it off your hands. Any special requests?"

"No, the guy left no details. Wants to meet at the Excalibur lobby bar at 6pm. Said he'll be wearing a sports coat with blue jeans, and a white baseball cap... his name is Kyle."

"So not James Bond then?" That got a chuckle from Lola.

"I'd say I owe ya, but guess who's in town tomorrow and asked for you?"

"The Sheik?!" I blurted.

"Uh huh. Wants you for the night. You may want to skip lunch... hell even breakfast." She was giggling now.

'The Sheik' as we nicknamed him is a very handsome middle eastern guy. He has numerous wives, but he has a kink that fits right in my wheelhouse. Apparently, he can't get a good blowjob anywhere back home and his wives were forbidden to do it. I was lucky enough to meet him my third week on the job and there was a definite connection... my mouth and his 9-inch cock. Our last date was 4 hours and I swallowed three very tasty loads. I couldn't wait to see what a whole night would get me!

Based on how my 'date' was dressed I went with a little more casual look and wore some black stretchy jeans, a bright pink silk bouse that hung off the shoulders, my hair up on one side and I finished the look with a pair of 4-inch strapped heels. I made my way into the Excalibur and filtered my way through a bus tour of people lined up to get their rooms. As I moved past the lobby partition, I could see a few people sitting at the bar and just on the other side had to be my guy. As I got closer, he must've sensed my movement, as he looked in my direction. His surprised eyes locked on mine, and I felt a twinge in my stomach. *Is that butterflies?*

"Hey there, I'm looking for Kyle. You wouldn't happen to be him, would you?" His eyes were a deep blue, like the tropical ocean, warm and inviting...

"Uhm, yes... yes, I'm him. I mean Kyle is me." He looked down to the floor then back up to me. "Hi, my name is Kyle."

I giggled at his cute nervousness. "Hi Kyle, I'm Sam. I'm from X-Gen." I was a little puzzled as he slowly shook his head.

Catching my reaction he stopped. "I'm sorry... I... how does one say this without being rude? You're not what I expected, I thought I'd be able to tell... you know?"

I smiled at his confusion and even felt flattered. "With all this political correctness, it's hard to tell, but thank you for being confused. May I sit?"

"Yes, yes, of course! Where's my manners?" He stood as I sat on the stool beside him, and he removed his ball cap. He was a very attractive man, and his dirty blonde hair was a cute mess from the hat. Instinctively, I reached up and corrected a few strands trying to put them where they looked like they should go.

"I'm sorry, but I suck at hairdressing, either way you still look handsome!" I gave him my widest smile and he looked pleased at my remark initially, but his smile dropped quickly. "I'm sorry, did I say something wrong?" I inquired.

"No, it's fine. I just remembered; you're paid to give compliments." He gave me a half smile.

I was a little hurt and maybe offended by his remark, as my assessment was genuine, but I had to realize how he might perceive things from a customer point of view.

"I suppose you could take it that way, but I assure you any and all compliments that I offer are genuine. I'm not into pumping ego's, if I don't have something nice to say... I say nothing. My momma taught me right." I could see him ease up a bit.

"I've never done, this (he pointed to the two of us) before, can I ask you personal questions or is there a protocol?"

I giggled. "There's nothing written in stone. Everyone has different comfort levels. How about we proceed in this manner. We can ask anything we want but if the other chooses not to answer it, we respect it and move on. How's that sound?"

"That sounds great." He smiled at me.

Kyle was quite the conversationalist and we gabbed back and forth sharing biographical info and stories from our past and present. Originally from a small town in northern Ontario, Canada, Kyle was fast tracked through university as his skill and knowledge of global economics was in high demand. He was recruited by a financial firm in San Diego and has been headhunted twice since then and now works for some major global investment company in New York. He was 32 years old, making him the youngest partner of the acting 14.

"So, what brings Mr. important business guy to Vegas Kyle. Looking to blow off some steam? Need a break from the Mrs.?" His whole face tightened, and I cursed myself for being so gregarious. "I'm sorry Kyle, it's none of my business why you're here."

He looked back at me and took a long sip, downing the last of his drink. He made eye contact with the bartender and motioned for another and looked at my wine glass, but I declined. As he put his glass down the bartender dropped a fresh whisky-coke in front of him.

"No need to be sorry Sam. That's a legitimate question." He took a gulp from his new drink. "I'm currently on a hiatus. I'm just roaming around trying to clear my head and get my game back." He took another sip. "And yes, it had something to do with a woman and no I'm not ready to talk about it."

I sat quietly and just nodded my head. I wanted to know more but my brain was busy asking me why did I care? I took a sip of my wine, and I gave him a soft smile.

"How long do I have you for Sam?" He looked at his watch. "Wow! 8:30 already! It's true... time flies when you're having fun!"

"I believe you booked 4 hours," I offered.

He looked at me and then back at his watch. "That gives us 90 minutes. You want to go somewhere fun?"

His sudden enthusiasm startled me. "Yeah, sure! Whatever you want?"

"Customer's always right!" He said. I don't think he meant it as a zinger, but I felt a little uneasy at his comment.

He threw down two $100 bills for 3 drinks, grabbed my hand and off we went. We walked through the lobby and up the ramp as we began to cross over to New York-New York. Like every other couple we held hands and truth was it felt so nice! It was like a real-life date with a new boyfriend. *What's wrong with me? Keep your shit together Sam! It's a job!*

"Have you ever been to the piano bar here?" He looked at me and I shook my head. "You like music, right? Like classics and new stuff?"

"I love music!" I smiled.

"You're going to love this place!"

We continued down the escalator into the main belly of the giant casino and he walked us to our destination. He paid our $20 cover and found a small stand-up table by the bar. It wasn't very busy yet, but he assured me it was going to get packed. He ordered us each another drink, as I took in the set up. In the middle of the room were two grand pianos facing each other, both with microphones. I could see on the one closest to me that the old ivory keys were replaced by a more high-tech keyboard with lots of bright buttons. There was a small dance space on either side of them and then there were tables and seating from the that point back. I had no idea what to expect but Kyle was sure looking forward to it!

We continued to chat and sip our drinks as more and more patrons came in. When the place was more than half full, two guys walked up to their prospective pianos and sat down. I had no idea what was going to happen, when suddenly one of them started playing. I recognised it right away, Piano man by Billy Joel... My father loved Billy Joel's music. The talented performer started singing into the microphone and his melodic voice put a smile on my face, as a rush of good memories came over me. Lost in my own thoughts, it took a moment to notice that Kyle was singing along. Not, like to himself singing, he was belting it out. *Not a bad voice.* I thought.

Then I realized that the bulk of the people were singing along and the mood in this bar was calm, yet electric with fun. The two piano players took turns, playing requests and the compositions were amazing thanks to the electronic keyboards filling in for bass and drums and the occasional brass. Everything they played seemed to be so popular everyone knew the words. They did a couple of Micheal Jackson songs which everyone knew, and people even started dancing. Kyle was singing Beat It, when he looked at me and we smiled as we both started to really get into it. Neither of us had a clue what time it was as the music just kept coming and the bar was getting louder and louder. We were all smiling at each other and raising our glasses in acknowledgement... everyone seemed so happy, including Kyle, and yours truly.

With hoarse voices we finally exited the bar and Kyle escorted me to a washroom, since we both had to pee really bad. When I came out, he was standing close by waiting for me and he put his hand out. I welcomed the intimate gesture and once again we started walking through the Casino.

"Kyle, that was soooo much fun! Thanks for taking me. I haven't sang like that since I was a kid!"

"So, you had a good time?"

"The best! You sure know how to treat a girl!" I leaned in and gave him a kiss on his cheek.

"Sometimes a customer gets it right." He smirked and that pissed me off.

I took his hand and turned it up so I could see his watch.

"Sorry, your bullshit means nothing now. I've been off the clock for three hours, so I guess you have to take a fucking compliment Kyle." I was surprised at how that came out and I was regretting it when I saw the pain on his face.

"Kyle? Why did you book this date? You clearly weren't looking for sex... and why a trans? Couldn't you just go on a regular date that didn't cost you a fortune?"

He gently pulled his hand from mine, and we walked in silence for a few minutes.

"I'm sorry I wasted your time tonight, Sam. You're truly lovely and I had a good time, so thank you. I'll square up with the club for your extra time."

"I don't want money Kyle... just a conversation, maybe even an explanation." I could see he was torn about sharing anything further with me. He settled himself and put his hand out, so I reached out.

"Thanks again Sam. I had a wonderful time with you." He proceeded to shake my hand and walked away leaving me stunned.

The next day, I shared my story with Lola and a few other girls, and they all agreed that he seemed sweet if not a little weird. I was reminded of my good fortune having got paid to go on a date, have fun, no sex required and made $300. I guess perspective was everything. That night I spent the whole evening in a high roller suit at the Cosmopolitan with the sheik. The bulk of my time was devoted between his legs, having sucked him off on the bed, in the shower, outside the jacuzzi, inside the jacuzzi, in front of the window, only to finish the night back on the bed with him lying supine and me lying prone between his legs, face full of his hard cock. The man was a sex machine and even though it was now 3am, I wasn't sure he didn't have another load after this one. There had been a reduction in the volume of his cum but after 5 blowjobs I was amazed he was still hard as a rock. At what worked out to $250 a load, it was a good night of work and pleasure.

I'd thought about Kyle a few times over the next week, usually while I was hammering inside a guys butt, I don't know why but he popped into my mind at those moments. I currently had a smaller Asian man on the back of his shoulders, with his ass up in the air, pile driving him while I held his legs. He was squeaking like a mouse with every thrust, and I had a hard time getting serious. This kept my orgasm at bay, and I fucked him for almost 45 minutes straight until I conjured up Kyle's face in my head and that brought my orgasm on quickly. I shot my load into my condom, while he spurted all over his own face... it's what he wanted.

On the cab ride home, I was thinking about that. He was in my mind regularly and I didn't know why. I never had to envision someone else to get off, I was always able to be present and give my client the orgasm they earned. I was looking out the window pondering my latest revelation when my phone went off.

Feel energetic? Your friend Kyle is requesting a date tonight. 9pm, same location. You up for it? He's not interested in seeing anyone else.

"Well speak of the devil." I mused out loud.

Sure, why not. He was sweet and pretty harmless. Thanks <3

After a quick turn around at my apartment, I had just enough time to wash off my goodies and put on a fresh change of clothes. I checked myself out in my short floral summer dress and headed off to meet the mysterious hot guy. I arrived at 8:55 and he was seated roughly in the same spot. This time he recognized me and left his seat to meet me at the end of the bar.

"Hey." He said bashfully.

"Hey back."

"Thanks for agreeing to see me again. I felt bad how things ended last time and I was hoping we could... uhm.."

Boy he was nervous. I'm not sure what he wanted to ask, but he looked terrified. "It's ok Kyle. Whatever you're about to ask, I can assure you the answer is most likely a yes." I smiled at him and could see him settle a little bit.

"Are you hungry?"

I didn't see that coming! "Uh... ya... I guess I could eat. What were you thinking?"

"There's a super nice steakhouse not too far, or we can go to the Polynesian, whatever you feel like." He smiled.

"There's a Popeye's chicken upstairs here in the galleria." I offered.

He stared at me and smiled. "Then Popeye's it is!" We started walking through the heart of the casino when I felt his hand grasp mine like they were old friends. We walked in comfortable silence until we got upstairs and while I grabbed us a small table off to the side, he went to order our food. He looked really good in his black jeans with the off-white thin sweater. He had a very nice build and the naughty part of my brain wondered if he'd take it in the ass. He caught me staring when he turned back to give me a smile and it was my turn to blush. *BUSTED!*

He made his way back with a tray full of our goodies and we ate while we conversed lightly. In so many of my "dates" the conversation aspect was usually the hardest part. Like a bad porn movie, it was the necessary preamble before the big money shot. However, it wasn't that way with Kyle. We never seemed to be at a loss for words and I found our conversations enjoyable. We flowed seamlessly through topics like movies, movie stars, aliens, artificial intelligence and cooking just to name a few. He had a great sense of humor and the fact that he also loved Adam Sandler movies was a huge bonus.

We got up from our table and Kyle pushed our tray of garbage into one of the bins, giving me another chance to quickly check out his bottom. We headed back to the main floor and this time I reached for his hand, which he accepted.

"Thanks for dinner Kyle. What do you want to do now? Do you have a room at this casino?"

He looked at me with his eyebrow raised. "Uh... no. I'm actually staying at Caesars Palace. What would you like to do?"

I simply shrugged my shoulders. "You made the date. I'm at your disposal."

He seemed uncomfortable with that context and looked forward as we walked. "You up for more music? We could head to Fremont Street, catch a couple of the bands."

Was this guy even interested in sex? I mean, I'm the definition of a sure thing, but this guy wants to play first dates it seemed... oh well. "Sure Kyle. That sounds like fun."

A quick uber ride and 25 minutes later we were walking under the light canopy, checking out the street buskers and people watching. His grip on my hand was firm and protective as we walked through a few spots that were overcrowded.... why did that feel so good? We finally got down to the end by Main Street, where a cover band called HAIR NATION was belting out a lot of 80's rock. They were very good and had the crowd singing and dancing, it was contagious. I soon found myself gyrating my hips and swaying with the rock tunes and I could see, from my peripheral vision, that Kyle was enjoying my show.