It took a week for the agency to approve my profile, after which it didn’t take too long to get my very first client. She was an adorable little old lady called Dorothy. Her husband had died and she wanted someone to go out to dinner with her from time to time and keep her company. I remember her once telling me she was ‘too old for all the faffing about that goes with dating’ and that by hiring me she could both enjoy the view and avoid the constant discussions about dentures and her date’s latest ailments that the conversation inevitably descended into when she went out with men that others might deem as ‘age appropriate’. Her and her husband had never done anything appropriate for their age, and she had no intention of starting now.

The very first time we met, I was so nervous. We chatted through the agency a little to set up all the arrangements but I didn’t know what to expect. We met at The Ivy on Buchanan Street, a chic and stylish restaurant which I would never have even considered going to with my budget. Miles had given me some tips beforehand, so I’d dressed up in my best suit, styled my hair just right, and didn’t wear anything that might make me stand out or look out of place. Dorothy certainly appreciated it when she first saw me cooing, “My, my, you’re even more handsome than your profile picture.” I’m sure I was blushing, “You look beautiful yourself,” I replied trying to turn on all my charm.

She giggled as the maître d’ came over and asked for the name of our reservation. Dorothy and I had discussed this in our initial communications through the agency, so trying my hardest to sound confident I replied, “Nelson, table for two.” We were shown to our table and once we were alone with our menus, Dorothy passed me across a small envelope which I tucked into the inside of my jacket. Thankfully, Miles had warned me not to check it at the table where everyone could see as I’m sure would have been my first instinct.

We chatted about the menu while we were deciding and once we’d placed our order I excused myself to go to the toilets. Following Miles’ advice, I slipped into a cubicle and checked the contents of the envelope. Inside was the money Dorothy and I had agreed on for my services, plus money for tonight’s meal. I slipped the money for the meal into my wallet and left the rest in the envelope inside my jacket. Dorothy liked to appear traditional to the outside world so that she could really surprise them on her terms.

After I returned to the table, the dinner went really smoothly. We chatted and laughed, everything just felt easy and much to my surprise there were no awkward moments where neither of us knew what to say. I’d always been one to speak my mind and found this was something Dorothy and I had in common. She told me about all the cool things she’d done during her life, and she genuinely wanted to hear about mine too. I’d tell her about my studies, about my life growing up, even my practically nonexistent dating life which she seemed quite saddened about. As the meal came to an end and I paid the bill, I found myself hoping that Dorothy would want to see me again. Not just for the money, although that was certainly good, but also because I genuinely did have a good time.

A few days went by when I got another notification from the agency of a booking request. When I was between my classes, I logged in to my account and saw that Dorothy had requested a repeat booking, I guess I didn’t do a bad job after all. Bookings from Dorothy went on like this every couple of weeks, she would pick the restaurant, wanting to experience a wide variety of sometimes quite surprising delicacies, and I would show up playing the role of the perfect attentive gentleman.

Each time Dorothy would book my services, my rating on the agency’s website would improve and as it did I started getting requests for more bookings. Mostly, they were older women looking for company for dinners or the theatre. But I still made sure I made time for Dorothy when she would make a booking request, as without her giving me a chance, I don’t know if any of the others would have given my profile a glance. That’s why when Dorothy mentioned one night at dinner that she had a special request, I decided to give it some serious consideration.

When it came to our next booking, instead of a fancy restaurant I found myself in the lobby of a far too nice hotel heading straight for the lift to take me up to the 5th floor where Dorothy had a suite booked. When the lift doors opened, I stepped out, took a deep breath and walked to room 507 where she had told me to meet her. I knew exactly what was planned once I stepped inside this room, yet still, I was nervous. I’d never done anything like this before, and I think back then, if we hadn’t already built up such a great relationship with one another then I probably wouldn’t have considered it.

I knocked on the door and waited, time seemed to slow down in that moment. It felt like I was waiting hours for the door to open, but it was probably only seconds. When the door opened and Dorothy was standing in front of me, I greeted her as she’d requested, “Hello mistress.” 

“Hello my beautiful boy, come on inside,” she replied while making way for me to enter the room. I walked in and stood at the foot of the bed with my hands behind my back looking away from her as she’d instructed. I couldn’t see her from this angle, but I hadn’t heard her move from the door since it closed, so it came as quite a shock when I suddenly felt her whisper into my ear, “You’ve always looked so good in that suit,” which she emphasised by squeezing my ass.

I jumped at the action but it was all part of what we had agreed, so I was more excited than surprised when she next spoke in my ear, “Let’s take off this jacket and get you more comfortable,” after which she helped to slide my suit jacket off my arms and onto the floor at my feet. She took a step back and more firmly this time ordered, “Pick that up.” I quickly moved to comply and felt a sudden sting of her hand spanking my backside. “What do you say when I give you an order boy?”

I was still reeling from the spank to think what the correct answer was, but apparently, my thinking was taking too long because before I knew it I was being spanked again. “You are supposed to acknowledge each order with ‘Yes Mistress’ before you carry it out. Do you remember now boy?”

“Yes Mistress,” I quickly replied, still facing away from Dorothy.

“Good boy, now, pick the jacket up and hang it up nicely.”

“Yes Mistress,” I remembered to say this time before I bent down to retrieve my jacket and hung it in the wardrobe. Once this was done, ensuring it was as neat as possible, I returned back to my previous position at the foot of the bed with my hands behind my back.

“Good boy,” she cooed, before taking a seat in a chair at the side of the room, “Now turn around and face me.”

“Yes Mistress,” the response coming automatically before turning to face her.

“Remove the shirt and hang it up nicely,” she commanded. I acknowledged her order and unbuttoned my shirt while she watched. I hung it up next to my jacket and returned to face her once more. She was clearly looking me up and down to take in all of me. Part of me felt a little embarrassed, but more than that I was feeling horny. It felt nice to be looked at, to be desired and the praise she was showering me with felt good too.

Next to go were my shoes, socks and trousers all of which she had me put neatly in the wardrobe. Once I was standing before her in just my boxers, I’d picked a nice tight black pair that it was impossible to hide my obvious arousal in, she stood from the chair and came over and started running her hands over my arms and chest. I had a pretty good body from my days playing rugby at grammar school, I have my Papa to thank for that, it was something he had encouraged both me and my brother Nick to do because he thought it would make us ‘attractive to women’, it was certainly working for me right now.

Then there was a knock on the door and a man on the other side called “Room Service”. Dorothy called back, “Just a moment,” before she reached for the top of my boxers and gave a swift tug to send them down to the floor, causing my hard cock to spring up and hit my stomach. “Let the man in David,” she said calmly and for a moment I stood there shocked and lost for words. “He’s waiting boy,” she said more firmly this time. Knowing I had to do as I was told, I turned and walked across the suite to the door. That felt like the longest walk I’d ever done.

I took a deep breath and opened the door, completely naked and my hard cock pointing straight out at the man on the other side. I noticed his eyes snapped down to my cock and quickly returned back to my face. Blushing he repeated, “Room service”, almost like it was a question. “Bring it in please,” called Dorothy from inside the suite so I stepped to one side and held the door as the man brought the food Dorothy had ordered before I arrived into the room.

“Tip the nice man, David,” Dorothy said with a hint of a smirk on her face. I walked to the wardrobe and retrieved a £5 note from my jacket to hand to him. As I did this, with no shame at all, Dorothy said, “Good boy,” which caused my cock to twitch. Looking back now, this was definitely where my praise kink started. The man thanked me for the tip and hurriedly left the room. Dorothy picked up the plate she had ordered for me and placed it on the floor by her feet. “Down boy,” she grinned and being the good boy that I am, I did as I was told.

After that day, I updated my Artist’s profile with the agency.

• Sex: Open