Kyle

I ended my deal with Paolo a year and a half after it began.

Being with Paolo was strangely liberating. He never once brought up money.. he had it deposited into a bank account weekly. He never made me feel like I was a paid either. Every time we were together was filled with laughter, exciting adventures, and mind blowing sex. We had a lot of fun, but I slowly realized that I didn't want to be his anymore. I wanted to move on. The money that I was making with Paolo had allowed me to quit my job and live a lifestyle that I never thought would be mine. I knew I could do this for myself... I just needed to figure out how.

I met Sammy at an event when I was working with Paolo. He was one of his business associates from Jamaica, and frequently made his way to Miami for meetings or events. Sammy was an older man, maybe in his late fifties, with a son that was around my age.. 24 at the time. He took a liking to me right away, and I did to him as well. He was such a cheery older man, always laughing and smiling. I felt instantly drawn to him, in more of a fatherly way than anything else.

We kept in touch after I left Paolo, and although we never spoke about our private life, Sammy knew about our arrangement. Kyle, Sammy's son, was going to be in town for a week, so Sammy called me up and asked if I wouldn't mind showing him all of the hot spots... and then some. I believe his exact words were "Show my son a good time, the way you did for Paolo. I'll take care of the money." Until then, I hadn't worked on my own. I was nervous, yet excited. Kyle was going to be my first official client.

Kyle arrived on a Tuesday afternoon with his soccer team. They were in town for some training that would last Wednesday through Friday, but he was staying a few extra days. I didn't officially meet him until Thursday evening. We had been emailing back and forth and made plans to meet at his hotel for drinks.

Rule 1: Exchange email addresses, not phone numbers. (There's a trace in case things go wrong, and it's a lot harder for someone to find out where you live. Safety first!)

Kyle seemed sweet and shy. He knew who I was, and had heard all about me from his father. He admitted to not knowing what to do with me, and I assured him that I would handle everything. We agreed on meeting Friday for dinner at one of my favorite restaurants at Hollywood beach, which is about 40 minutes from my home in Miami. I figured it would be easier to take clients somewhere neither one of us would be easily recognized.

Our dinner went well, but I could tell he was nervous for what would come later. We had been drinking throughout dinner and by the time we made it to his hotel, Kyle was a very different man.. confident, sexual and borderline piggish. When he asked me up to his hotel room, I agreed. I was just as horny if not more so than him.

We entered the room and again he seemed nervous. I knew I had to relax him, or this wouldn't end well so I made him remove his shirt and lie face down on the bed. I came up behind him and placed one leg on either side of his body, sitting on his butt. One thing about Jamaican guys... they have nice plump behinds. I traced up and down his back with my nails, a relaxing technique my mom used on me as a child. His breathing slowed and I knew he was on his way. I stood up to grab some lotion from the bathroom and when I came back he was sitting on the edge of the bed.

I walked over to him and stood between his legs, rubbing his shoulders and the back of his neck. "Are you sure you want this?" I asked.

Rule 2: Never do anything you or the other party are completely uncomfortable with. 

He rested his head on my stomach and exhaled. "More than you know."

"Okay." I whispered. I pulled his head up and kissed him softly. He lifted my shirt over my head and undid the zipper on my jeans.

My pants were tight to my body so I had to physically bend down and peel them off. Not very sexy, but necessary. I stood in front of Kyle, in just my bra and panties, waiting for him to make the next move. I like leaving the client in charge, it needs to happen at a pace they're comfortable with. He rubbed his hands down the sides of my legs and back up, caressing my breasts.

"Take your bra off."

I did as I was told.

"Now the bottoms."

I removed my panties.

Standing completely nude in front of a half dressed man would intimidate most women, but to me, I felt liberated. I love the way a man's hungry eyes run across your naked body. My body is my money maker, so I always make sure I'm well groomed, and physically fit.

"Come." He signaled for me to walk towards him. He stood, switching places with me, and laid me back so that I was resting on the backs of my arms. He undid his belt and pant buttons, but didn't remove them.

I sighed unknowingly. I was becoming frustrated at how slow he was going, but again, I had to let him dictate the pace.

Kyle laid himself on top of me and rubbed his hand between my legs. "You want it so bad, don't you? You're already wet for me."

"Mmm... Yes."

He continued to work his hands between my legs. He wasn't as good at that as Paolo. Paolo left me wanting more of him. Kyle had me wishing he would hurry up and get me off.  He finally stood up, removing his pants and boxers in one motion. When I saw what he was working with, I needed it even more. I've been with my share of men, but none compared in size. Kyle was huge. HUGE. I watched as he fit the condom over himself, again taking his sweet ass time. I had a feeling he was doing this on purpose.

Rule 3: ALWAYS use protection. No excuses. No condom, no sex. 

Until this point, I had let him take his time, but I needed to make sure I got some in this century... so I pulled him down on top of me and kissed him aggressively, he got the hint. Slow and steady Kyle turned into the ferocious beast that I craved. He slid into me hard and fast, pausing for a bit allowing me to get used to his size, and when I gave him the okay, continued.

Kyle then spun me around, so that I was laying face down on the bed, and entered me from behind. I cried out as he hit every pleasure spot that I possess. He took my hand and rubbed my clit with it while he pounded in and out of me. I was a hot shaking mess within minutes. Kyle came not long after and fell on top of me. I could feel him still inside me, and even though I was spent, I wanted him again. I couldn't believe that this was the same man from an hour earlier.

We spent the rest of the weekend in that hotel room. Kyle fucked me in every position, on every surface. We ordered room service when we got hungry, and only left the room when he had to catch his flight home. Kyle promised to let me know the next time he was in town, but I never heard from him again. Sammy sent me a thank you email a few weeks later, promising to send me more business. A promise he kept. I will continue to be thankful to him. His endless list of business associates are the reason I have a career to this date.


**Disclaimer: All stories are true. Names and any identifying details have been changed.**