I was in my early 20s just out of college when I had my first experience with a man. I was attending a conference in my home city for a training with my new job and it had just let out for the afternoon break. It was at a hotel near downtown and I went to the bar for a quick bit of refreshment. It was next to the lobby and mostly empty except for some people, mostly men, in business attire. I sat down on a stool alone at the bar, ordered a beer, and watched the TV. I had worked out and lifted for years and it showed with my tight polo around my shoulders and khakis tight around my thighs and ass.
As I was sipping and looking around, another man came into the hotel bar. He was in a business suit and we caught each other's eyes for a second as I was staring a little too long. I turned back to the TV a little nervously. Next thing I knew, he was sitting at a stool just one away from me. As he ordered a drink, I turned and we caught eyes again. I smirked and nodded a little nervously and looked away.
He was older than me, maybe early 50s but had taken care of himself. He was a little taller than me and, though not a linebacker, was in good shape. I casually looked around and as I looked his way could see he was eyeing me up. It seemed like he was almost checking me out. I smiled nervously and said hi. He smiled back and slid over to the stool next to me.
"How's it going?" he asked with a confident smile.
As he slid over, our knees touched and gently pressed against each other. I looked down quickly but froze, unable to move my leg away.
"Oh, uh, hey, not bad. I'm not bad. How are you?" I replied while fidgeting with my drink, my cheeks starting to redden slightly.
"Rough week at work, but the bourbon is helping!" he said cheerfully.
I smirked shyly. "Yeah, I bet it helps everything, doesn't it?"
"Who's winning?" he asked as he looked up to the TV.
"Oh, I don't know. Wasn't really paying attention." My legs were still frozen and I finally adjusted slightly. My leg barely brushing against his. Neither of us pulling away.
He set his empty glass down after draining it. "You need another?" with that same knowing smile.
I gulped and finished mine too. "Uh, yeah, sure." Smiling and trying to hide my nerves. "I never turn down a free drink."
He signaled the bartender and had our glasses refilled.
"Cheers!" he said as he lifted his glass.
"Thanks, cheers," I replied as I tapped his glass with mine, my arm lightly touching his shoulder as I did and my leg pressing harder against his as I turned.
"I'm Bud by the way. Good to meet you," he said as he extended his hand.
I set my glass down and shook his hand feeling his strong grip. "Hey, nice to meet you Bud. I'm Zach." I caught his eye for a second and looked down nervously. My cheeks felt warmer.
"Just out of curiosity, Zach. What do you charge?"
"Um, what was that? Charge?" I asked as I looked over confused.
"I mean, you are an escort, right?" he said as he smiled and nudged my shoulder, my body twitching at his touch slightly, resting his hand there long enough for me to see the wedding band.
My mouth gaped a little as I turned with my eyebrows raised. "Uh, you think I'm an escort?" I said with a hushed voice leaning closer to him so no one would hear.
"I mean a good looking young man in here, looking around at all of the older men. I just assumed! And you were looking around like you are expecting someone," he said as if it was obvious.
"You think I'm an escort?" I asked again a little surprised as it still was sinking in with a stunned face. "Uh, no... I'm not sure if I should be flattered or not." I smiled and laughed nervously.
"I'm sorry. I hope I didn't offend," he apologized. Still neither of us had pulled our legs back from touching.
I cleared my throat and smiled as I adjusted in my seat. My leg slid against his and I didn't pull it away. "So you thought I was and..." I paused at the thought of what it implicated. "I mean, you were interested in buying my services for the night?" Looking over at him incredulously with my cheeks burning.
"Well, if you were, and now I know you are not, what would your rate be?" he asked clearly enjoying the topic of me being his escort for the night.
I cleared my throat again and swallowed. "I have no idea what a male escort would charge," I said taking the question seriously. Unconsciously, before I turned back to my drink and before I knew what I was doing my hand patted his thigh playfully.
"Well, I think it depends on what you were willing to do. But a young, fit guy like you could earn a lot of money," he said while he looked me over once.
I looked down at the bar still processing all this biting my lip just slightly. "Really? How much?" I asked feeling my face grow hotter and smiling shyly.
"Gosh, I would think you could probably pull down $1000 a night easy. I mean depending on what you were willing to do."
"A thousand bucks!" I said as I turned towards him a little surprised, my leg pressing harder against him. "What would you have to do?"
"Well, I mean there are guys who will only suck dick, they make the least."
I looked over and couldn't stop my eyes from looking down to his crotch for a second. "Oh, well, how much for the most?" I asked while swallowing again in disbelief that I was having this conversation. Embarrassed by how hot my face felt. My mind racing I asked, "You wanted me to... do that... to you?" Looking over at him and catching his eye but not able to keep his gaze. I looked down and bit my lip nervously.
"It's really a la carte, you know? So it depends on your limits"
"Hey, is this just a joke?" I asked while smiling and looking around expecting a camera or someone watching to laugh. "Like a prank or something?"
"No, I am dead serious," he said emphatically.
"Really?" I said still in disbelief smiling nervously and blushing. "What were you thinking you wanted me to do?" I looked back over to him and bit my lip and adjusted in my seat again. I couldn't help but look him up and down.
"Like some guys will only want to give you a handjob and that's like $50. They say they aren't gay, so they won't go down," he said with knowing smirk.
"You just wanted a handjob?" I asked while gulping nervously and unable to stop myself from peeking down at his crotch. I felt my cheeks get hot again as I realized I was trying to see how big his cock was.
"Rarely!" he said with a laugh at how naive I was.
"Well, I've never been propositioned like this before," I replied a little bashfully as my face felt hotter. I picked up my drink with a slightly trembling hand and downed it quickly.
"But it is usually a good place to start!" he said with a friendly smile as he looked at me. "How would you like to make a grand the hard way?" he said with a teasing laugh.
"Hmm, yeah, I wouldn't know. Never done anything like that. But it is interesting that you want, I mean, you want..." I paused again thinking about the implication, thinking about what this man wanted to do with me. "You want me, I guess." I trailed off and blushed bright.
"Well, I guess I should thank you for not getting mad at me," he said with a warm smile.
I laughed nervously. "Yeah, um, no problem. Maybe I should be mad but I kinda take it as a compliment," I assured him as I smiled back shyly and blushing.
"I bet you would probably be pretty good at it! I mean, if you ever needed or wanted the money."
I smirked and looked at him with an embarrassed sideways glance. "Why do you say that?"
"Just a sense or feeling, I guess. Is there anything you wouldn't do?"
I reflexively gulped nervously. "Uh, I mean, I've never done anything like that, you know, like with a guy before..." I trailed off as my cheeks grew warm.
"I believe you, but you didn't answer my question."
"I mean, I'm not like that, that wouldn't be me..." I said quietly. My tongue unconsciously feeling my lower lip before I bite it and my face growing hotter.
"Well, I am heading up to my room to drink some more there," he said as he opened his wallet stuffed with cash and then threw a couple bills on the bar to cover for the drinks. "If you would like to discuss your financial opportunities, let me know." He stood up and slid his room key in front of me on the bar. I couldn't help but notice a bulge at his crotch.
"Uh... okay," I half mumbled while biting my lip and looking sideways thinking and unsure. "Well, it was nice talking with you... I mean, thanks for the compliment." I smiled and could feel my face growing hot. I turned back to the room key in front of me and finished my drink then turned back to watch him walk to the elevator.
"Oh fuck," I whispered to myself feeling my heart beat harder.
I sat for a while finishing my drink and staring and fidgeting with the key. Biting my lip hard, I finally picked it up saying to myself, "I should take this and just return it so no one else gets it..." My face was still hot as I put it in my pocket and walked to the elevator. My hands started to tremble a little as I walked to his room and knocked.
Silence. I checked that I had the room number correct and knocked again. There was still no answer so I tried the key and turned the knob thinking I would just leave the key inside since he was away.
I pushed the door open and started to walk in slowly towards the dresser with the TV on it. When I got further in I saw that he was lounging on the couch and I froze. We locked eyes and he smiled.
I swallowed hard and motioned to drop the key on the dresser. "Uh, I was just going to bring your room key back. Didn't want anyone else getting it," I said as I set it on the dresser. "I'll just leave it here."
"Come on in! Want a drink?"
"Uh, no, I mean, I was just dropping off the key," I said but didn't move to leave and stared as I felt my face get red hot.
"Come on. One drink won't kill you, or make you do anything you don't want to do."
I could feel my face burn and couldn't seem to move. I bit my lip and swallowed hard again. "Uh, yeah, I guess, sure..."
