My instructions were pretty simple. Arrive at 8:00pm, enter through the library door, remove my clothes and assume the position of a submissive. I did as I was instructed and waited.
I waited like a good boy for what seemed like an eternity before they walked in. Not knowing who they were was of no concern. This is what I do. All I know for sure is, I was sent a first class ticket on Delta to Atlanta where an Uber picked me up and delivered me to the house. And the most important thing, the money was deposited into my account.
I am an escort. That sounds better than male prostitute or my least favorite, call boy. I work through an agency that is headquartered somewhere in the Caymans. I receive a text. I say yes or no. Money is wired and that's that. My resume is quite impressive. Men, women, groups, senators, a judge or two and more business people and the lonely than I can count. I don't have sex with all my clients, but it is always on the table, and it's not cheap.
To be successful in this business, you must keep your body in great shape. The grooming impeccable. I read three books a week and every newspaper and magazine available. I can quote poetry when needed, the stock exchange and sports, when required.
Any new hotel I enter I always give the concierge and desk captain a small gift. The bartenders are tipped embarrassingly. As are housekeepers, bellboys and anyone else I come in contact with, all expensed to the client. As I said before, it's not cheap.
But what would you be willing to pay for a night or weekend full of fine wine, theatre and great sex? Or Shiner Bock beer, a rodeo and great sex?
I did not enter into this line of work like others. I had a couple of mentors. A married couple that was thirty years my senior. He was a real estate developer and she, a judge. I was originally hired to work on their estate taking care of the gardens, the pools. I was paid a small salary but given a room in what, was loving called, "the bunk house." There were three of us when I moved in. Ali, the girl who worked in the stable and Bart, an ex high school jock, whose job mainly was to do all the heavy lifting, already had the bigger bedrooms so I took the smaller one at the end of the hall, which worked in my favor as I was in my last three semesters in college. My employers knew that and allowed me flexible hours.
One summer, weekend night, after I had been there a bit, I was working out in the gym they provided for us, when the Mrs walked in. Never had I seen her in our little gym.
"Good evening, ma'am. Is there something I can help you with?" I released the bar I was using, wiped my face and grabbed for my t-shirt.
"No, I was going for a swim in the lower pool and I saw you working out through the windows."
"I'll remember to close them from now on ma'am."
She giggled. "No, I'm sorry. I wasn't complaining, I just thought I'd drop in and say hello. But you're busy..."
"No ma'am. I was finishing up."
She was wearing a thigh length robe that more or less covered her barley there bikini. Remember, she was fifty years old, or there about. Her body was tight. Her dark hair flowed over her shoulders. Her legs were perfectly diamond shaped. It was not my first time to see her in a bikini, but that night things seemed different.
"Well good. I was wondering if you'd like to swim."
"Me, ma'am?"
"Yes, you, Marcus."
"I'll grab my suit."
"I'll meet you there."
The lower pool was the one the employees used when it wasn't being used by the family.
It was very cool. Secluded. And one of my favorite places on the estate. I once saw Ali getting off on an air mattress. I waited an appointment amount of time before letting her know I was there. I don't think she ever found out I saw her.
She dropped her robe and dove in. I followed.
My head was not thinking sex. Why would she risk all this for a fuck with the yard boy? My cock was thinking something other. With her every stroke I got harder. She did that swimmers turn at the other end and came up in front of me. As she popped up, she put her right hand behind my head and kissed me. I kissed her back. And again. Her left hand went to the small of my back bringing me even closer. My hands went straight to her ass. She removed her top revealing some magnificent breasts. She had a daughter a couple years older than me but I would guess mom is in better shape.
"Grab that foam mattress," she said as she stepped out of the pool. I did as I was instructed. "Put it here."
She took a towel and pitched me one too, before she stretched out on the pad and indicated I should join her. I did.
She ran her hand across my chest and looked me in the eyes. I was busting out of my suit. She kissed me. Her tits on my chest felt wonderful. Her breath had a lingering taste of wine. I wasn't that experienced with women but I had always been the aggressor. This was new territory for me. But I learned quickly. I nibbled her nipples and then moved straight to her pussy.
"Slow down, Marcus. We have all night. And, evidently, you have a few things to learn."
At first I was pissed. She wasn't my first fuck. But it didn't take me long to realize what she meant. It was the most amazing night of my life up to that point. Everything I tried she either shut me down or at least slowed me down.
"The mark of a great lover," she whispered, "is taking care of your lover." She removed my trunks and began to play with my already hard cock. "You see, it's not all slam bam thank you ma'am. It's slowly teasing your partner." She stroked my cock, occasionally running her nails along the underside causing me to jump.
"See? It's not just about your orgasm. It's the whole experience."
Just when I thought I couldn't stand it anymore, she stopped. She ran her hands all over my body, carefully avoiding my genitals.
I was going crazy. She kissed my nipples and my belly. She ran her nails up and down my torso. If she had even looked at my cock I would have exploded. But she didn't.
"Remove my bottoms." I grabbed at them and began to jerk them off. "No, sweet Marcus. You remove them gently, letting her lift her hips, thereby giving herself to you."
She lifted her hips allowing me to gently remove the bottom part of her bikini. Her eyes never left mine. At first that was weird to me, but before long, my eyes were linked to hers. Erotic as fuck!!
I received an education that night. At least, my first lesson. All night she taught me how to please a woman. She was amazing. We made love a couple times before falling asleep outside on that mattress. At 3:00am I was awakened by her blowing me.
"You know what I want?"
"No ma'am, what do you want?"
"I want you to fuck me."
"I have but will be glad to again."
"You didn't hear me. I want to be fucked. Fucked hard. No romance, just fucking."