Escort - Sugarbaby Offer

Several evenings ago I arrived at a midtown hotel where an older gentlemen greeted me by the downstairs’ elevators. We had never met previously, and his request to join him at the hotel bar made me very uneasy. “No, I will meet you at the elevators.” Was the last text message I sent his way before stepping out of the car.

The hotel reception area seemed vacant, at a glance a single hotel staff member scurried off down a corridor with a few plates in hand, and one unassuming man holding an iPad stood by the elevators. I walked a few paces past him, stopped and looked in his direction. “Hello.”

I smiled and greeted him back.

During the elevator ride he asked me if I was originally from here. “Yes.” I lied. And a few other pleasantries were discussed. The room was very nice! Modern and almost seemed like it had once been a condo suit. He asked me if I would mind waiting while he showered and brushed his teeth. I told him I would wait on the bed in the other room.

I sat down on the king size bed, and started texting my driver. “Buddy is really taking his time- showering, brushing his teeth. LOL”

“He must be a chill guy.” My driver wrote back.

I put away my phone and began to undress. If he’s getting all ready for me in the shower, I should at least strip to my lingerie! That evening I wore my violet bra and matching Brazilian style panties. Finally, he came into the room completely nude.

Slowly, while looking at him standing by the bedside, I crawled towards him on the bed. When I reached him, I paused, and looked up with a smile. He placed his hands on my shoulder blades and ran his fingers through my long hair. We spoke a little more while I stroked his body with my hands, teasing his genitals. And then I asked him if he’d like to lie down in bed with me.

I could tell he was trying to take his time and so I just took it easy. At first I removed my bra, straddled his body and started to slide my chest gently against his chest down to his groin. He played with my nipples and I offered that he kissed them. “They are very sensitive, in a good way.” I added with a wink.

“Would you mind taking your panties off?” He finally said. “Well of course,” I laughed, “Sometimes I get so excited that I totally forget that my panties are still on!” I joked while I took them off.

“Can I play with you?” He asked, with a motion of his hand toward my pussy. “Yes, but I like it gently please.” And after a bit of lube placed on my inner lips, I let him spread me with his fingers. It felt pretty good for a little while, until him rubbing became a little rough. A change of position took his focus off me and back to him. I opened the condom wrapper, placed the rubber tip in between my lips and rolled the condom down his erect shaft with my mouth. I could tell he enjoyed the blowjob I was giving, but I did not want to make him cum yet. I made long slow strokes and swirled my tongue only occasionally.

After a few minutes he gave me the cue - it was time for me to board the train. I straddled his hips with him lying on the bed below me. And started to slide his dick inside of me. It was an awkward position, and for some strange reason I could not explain why (even at this time, as I write this). He felt it too and suggested we try doggy style. Once we made contact again, this new position seemed to work well until he was finished.

We lay back on the bed and talked until the hour was over and it was time for me to go. From our conversation I learned that he was retired (in his late 60’s). Loved to travel and had got out of a long-term sugar arrangement just 6 months before. He referred to it as an ‘arrangement’ and told me about the woman who used to accompany him on trips. It was also revealed to him that I tried being a sugarbaby for a few months. He wanted to know some specifics and seemed interested in feeling out my thoughts on another such relationship. I did not let on.

The following day I received an email from him thanking me for the appointment and that he would see me again. A note at the end said, “If you would like to abandon the escort scene let me know...I would like to look after you!” 

Now, I did respond with a nice email but I left out any answer to his last comment. And here is why… after I have done some soul searching…

I cannot be exclusive with one man that I am not attracted to.

The perk of this job is having variety because at least 1 in 5 men will actually be somewhat satisfying to fuck.

In the scenario he is presenting to me, I would have to endure the same lame fuck over and over again. And I can do a lame fuck for 1 hour but when that hour is up, it is out of my sight and out of my mind. I know that there are greener pastures in some other hotel rooms ;)  LOL