My company was sending me off on a business trip for a few days. I’d be flying a few hundred miles away and then staying in a nice hotel. I’d have seminars each day, but my nights were totally free, as I was the only one sent from my company. My flight was smooth and easy, and I found that the hotel was even nicer than I thought. The first day’s seminars weren’t too bad, and I finished off the day with a light dinner in the hotel restaurant.
Back in my room, I slipped into my slippers and wondered what I should do. I thought about renting a car and seeing what the area had to offer as far as nightlife. But my hotel room was so nice, and I felt so relaxed and comfortable there, that I quickly changed my mind. I knew there was only one thing to do…
Hire an escort.
I jumped up and grabbed my laptop and started surfing away. Back home I had been seeing an escort named Bianca on a weekly basis. She was a sexy Latina, who after over a year of “dates”, still made me weak in the knees. She wasn’t particularly affectionate and seldom looked me in the eye, even when we weren’t having sex, and never once called me by my name, but she was drop dead gorgeous, and I was hooked on her. She’d even stolen a few things now and then from my apartment, but I was so pussy-whipped that I never said a word about it.
Now, being in a new place – a place where no one knew me, I started thinking that maybe it was time for a new beginning. Maybe it was time to start demanding better out of life. I’d only be here a few days, but if I changed my attitude here, I thought maybe it would stay changed when I got home. It was worth a shot at least.
After about fifteen minutes on the pc, I found a lady who fit my personal taste, and who looked like she was cut from a different cloth than Bianca and the other girls who’d taken advantage of me in the past. Of course, looks can only say so much, but I had to start somewhere, and choosing her over the sex-pots was definitely a change of attitude for me.
Her name was Ivanna, and she was Latin like Bianca. They had the same hair color (black), but that was just about where the similarities ended. For her look was demure and refined, while Bianca’s was hot and sexy. I knew that there was no guarantee she’d be any nicer than Bianca, but I felt like she was a good choice for my “new beginning”. But above everything, I reminded myself that I was the only one who could guarantee I was treated with respect. I was the final decider on in which direction my new beginning would go.
I called up the agency and spoke with a nice gentleman, who told me that Ivanna would be over within forty-five minutes. I looked at her pictures for a while and even saved each one. Then I brought a chair over to the window and positioned myself to have a perfect view at the front entrance. After about fifteen minutes, I saw a black Lincoln roll up, and I instantaneously got hard, thinking it could be her. Out of the back passenger side stepped a female figure. She had shoulder-length black hair and was wearing sunglasses. She was wearing a yellow blouse and black skirt with black high heels. and carrying a large black purse.
Within two minutes, my cell phone rang with a blocked number. I answered it before that first ring even stopped. It was Ivanna, and she said she was down in the lobby. Her voice was as sweet as her pictures. I told her I’d be right there, and I tore out of the room and headed for the elevator. The elevator seemed like it took forever to come…and then forever to get down to the lobby. But finally I was out and walking towards the female in the yellow blouse who looking down at her phone.
“Ivanna?” I asked.
She turned towards me, and her face was just as lovely as it had been in her pictures.
“Steve,” she said. “How are you?”
“I’m well. How are you?” I asked her.
“Just fine, thank you,’ she replied.
“Shall we go up?”
“Yes, certainly,” she said with a smile, and I led her to the elevator.
“Nice slippers,” she said, looking down at my feet.
“Thank you,” I blushed.
The elevator ride seemed long again, but I didn’t mind. There was a definite attraction on her part, as well as mine, and we just kept looking at each other and quietly laughing.
Once we got to my room, I paid her the hourly rate, and she thanked me. I told her to make herself comfortable and asked if there was anything I could order up for her or get from the vending machines. She politely declined, slipped out of her shoes, and sat on the bed. I came and sat down next to her, and we restarted our game of looking, smiling, and laughing. She brushed the hair away from my forehead and studied my face. while wearing a warm smile. Then she leaned closer and gave me a soft kiss on the lips. I held her cheek with my palm and returned the favor. Soon we were kissing each other in earnest, caressing each other all the while.
It was a big difference from Bianca, who never let me kiss, no matter how much I begged. There was one time that Bianca finally agreed to kiss me, but she wanted $50 for it. I felt that I just needed to kiss those lips, just once, so I ran and got a fifty and put it in her hand. Bianca walked over and put the $50 bill in her purse and came back to me. I felt like a little kid on Christmas when I leaned in for the kiss. But instead of her lips, I got the palm of her hand covering my mouth. I angrily asked her what the hell she was doing, and she snottily said that she was teaching me the hard way not to ask for kisses.
Now, with Ivanna, I was not only feeling respected and desired, I was also feeling quite alpha. I was holding her slender body in my arms, and I had an overriding feeling of “man conquers woman’ that I hadn’t had in years. She was a delicate creature, and as I held her I was dominant yet protective; I was part cave man, part knight in shining armor.
As we quickly began to undress each other, my confidence continued to grow. I actually started thinking that there was no way she would charge me any personal fee on top of the agency fee I’d already paid. Then I realized that I might be expecting too much, for as far as I knew, even the most studly of men were not exempt from paying the personal fee when hiring an escort. But I was absolutely sure that she would give me a good deal. I was convinced that she’d just ask for enough to cover her expenses or what not.
Once we were both naked, I tried to pull her towards me and fully up onto the bed for lovemaking, but she resisted.
“Hold on,” she whispered. “I have to get something from my purse.”
I figured she was getting a condom or some other kind of birth control. I pushed myself up onto the bed and lay on my back waiting for her, while looking at the ceiling. Within a few seconds, I heard her coming back my way. I picked my head up and saw her carrying her whole purse over towards the bed. I supposed she was having trouble finding the birth control. She then climbed onto the bed, purse and all.
I went to grab her, but she evaded my touch.
“Wait,” she said. “There’s something I want you to see.”
She reached into the purse and pulled out a grey, glistening dildo. Her eyes were dancing, as she held it towards me.
I was utterly shocked. “Why do you want that? Mine works pretty well,” I said, although my throbbing, dripping erection was now just a limp noodle.
“Oh no, honey. It’s not for me. It’s for you,” she said, pulling a type of strap out of her purse.
I couldn’t believe my ears or my eyes.
“Why? Why do you think I want that?” I demanded, as I watched her attaching the dildo to the strap.
“Oh, I could tell. I know about boys like you.”
I felt so prejudged, so misunderstood. I couldn’t believe she would make that assumption about me, especially since I had been doing everything like a true man would.
“I’m not like that, Ivanna. I want you to put that away and let me have you.”
She sat motionless for a moment and then gave me an ultimatum, “If you don’t want this, I will put it away. But understand this: once it’s away, it stays away. So you decide. Do you want to put your cock in me, or do you want me to put my cock in you?”
All the confidence and manliness that had been growing inside me earlier was nowhere to be found, and I wouldn’t have been able to get it up anymore anyway. And plus, the thought of her fucking me with the strap-on was making me feel all warm and fuzzy inside. In fact, I was starting to feel like myself again, and said a silent thank you to God for getting all that alpha nonsense out of my head.
“Ok, Ivanna,” I smiled. “I want your cock inside me.”
Her eyes sparkled and she smiled a wicked smile, as she donned the artificial dick. I felt like I was in an erotic trance; I was so at peace with myself. I was delirious with anticipation, yet fully calm and patient. I was just enjoying being who I knew I should be. All was right with the world again, and I started to assume the position.
“Oh!” Ivanna said as if she’d just remembered something. “By the way. This is not included in what you paid me. I’m gonna need another $200, sweetie.”