Barista Boy
She was my favourite customer, a regular who came in every morning for her cappuccino and pain au chocolat. She took the same seat by the window and would spend precisely one hour on her notepad, typing constantly while she sipped her coffee and nibbled her pastry so delicately.
She looked in her late thirties but could have been older. Sleight of frame with a slender almost skinny figure, a strikingly beautiful face with long brown hair that she would flick off her face constantly as she looked down at her notepad.
She always dressed conservatively but wore heels so high I would call them fetish shoes. She probably wore them just to give her extra height but to me they were something else, I had a thing for stiletto heels and dark stockings. She only went bare legged in the summer months otherwise her legs were sheathed in what I dreamed were stockings, hopefully not tights. Her hemline was never short enough for me to get a glimpse to confirm or deny my fantasy.
I will break off here to tell you a bit about me. I am a man in advanced middle age who had made a good career for myself in a highly stressful job in engineering. I had banked enough money to be comfortable, with shrewd investments and pensions to allow me to have escaped the stress and take early retirement. I lived alone, divorced years ago and my kids had fled the nest and started lives of their own.
I am confident, outgoing and friendly with a wide circle of friends, but I hide a secret from them. I am deeply into the BDSM lifestyle, a submissive masochist who has had many experiences in the lifestyle, having served my wife who took the dominant role in our relationship for many years. Since my divorce I had been in a few relationships with confident women who carried an air of authority and command, some were in the 'lifestyle' and other not but they were all women to whom I wanted to submit to.
Since covid struck I had shied away from any relationships so I now spent most of my time stuck in the house with just the occasion outings with friends and felt something missing in my life.
To relieve some of the boredom I felt from being on my own all day and to get out and have some social interactions with people, I took this part time job as a barista at a bistro near the railway station. I enjoyed it immensely, it got me out and meeting people, I developed good working relations with my colleagues in the bistro although I was old enough to be their grandfather, so we didn't meet socially outside of work.
Back to the tale.
Her name was Tilly, short for Mathilde I later found out and I had a huge crush on her. The heels and hopefully stockings she wore had me imagining her as a strict dominant woman who would enslave me and lead me to the fantasy life I always dreamed about.
Her demeaner was the exact opposite, she was always friendly and polite, showing kindness and a bubbly attitude, engaging now and again with some polite conversations and had the confidence I found so alluring in bucketfuls. I served her with all the respect I could give, while keeping things strictly appropriate and trying not to come across as some creepy old perve.
This particular morning I took her order to her table, giving her a big smile and an imperceptible nod of my head as I placed her coffee and pastry on the table beside her little notebook. I noticed the website on the screen, one I had looked at myself many times, Literotica.com was displayed in bold letters on the top left side of the screen.
I would have hidden the page as soon as I saw someone approaching if I was viewing that site, but she made no attempt to as her eyes flicked up and held my gaze.
"Your coffee Ma'am." I said cheerily but with a hint of emphasis on "Ma'am"
Holding my gaze a little longer than she normally would, a hint of a smile and mischief on her face. "Thank you, boy." She replied.
Her face held a look of serenity and calm while mine was the exact opposite. For a fraction of a second she held my gaze to see my reaction to what she had said. Satisfied the implication had hit its mark, she looked back down to study the screen in front of her as if to dismiss me. I felt my face turning scarlet and the heat rushing into my cheeks as I hesitated for a moment before walking back behind the counter.
"Oh my god, oh my god." I thought to myself. "She knows, she knows. Ohh shit!"
I made my way into the stock room for a moments privacy and to process what had just happened. My mind racing at all the possible meanings and implications of that single little word.... 'boy'.
After a few minutes of deliberation I had calmed somewhat. Okay, she had obviously worked out my submissive nature. My not so surreptitious glances at her heels and legs, the telltale giveaways of my demeaner towards her had obviously been picked up on by someone who was 'in the know' and I was busted but I felt so happy that I was.
Much calmer now and back to my usual self I walked back into the bistro. She knew, so what? I wasn't ashamed of what I am, it was at the core of me and to be ashamed of it would have meant denying to myself what I was, a proudly submissive male for the right woman.
I got back to work serving drinks to the queue of customers and when things got a little less hectic, I looked over at her table but she had already left.
The next day when she walked back in, I smiled to her and nodded my head in acknowledgement, a little more than I normally would to show a hint of my subservience. She smiled back knowingly and mouthed 'my usual' to me before taking her seat. As I prepared her coffee and pastry, I could feel myself blushing after I had glanced over at her, only to find her staring at me with a knowing look in her eyes.
As I took her order to her table I couldn't help but look down to look at the spiked heel shoes she was wearing, I could see seams along the back of her calves which convinced me she must be wearing stockings today and that thought made me tingle with excitement and I felt the needy submissive fire in me begin to flame.
Placing the mug of coffee and the plate of pastry on her table, she teased a strand of hair behind her ear and looked at me, fixing me with her gaze.
"Do you have a minute?" She asked.
I looked around, there was nobody waiting to be served and the supervisor was on her break so I decided it wouldn't do any harm to take a short break.
"Yes Ma'am." I replied. I pulled out the chair opposite and went to sit but hesitated, she nodded her approval, and I sat down.
She fixed her gaze on me again, even through the glasses she wore her eyes were striking. I struggled to maintain eye contact with her as my natural deference to her made me want to look down.
"You enjoy your job here?" She questioned.
"Yes Ma'am, I do. It helps pass my time" I replied.
"Hmmm? Have you ever thought about finding another job, would you be open to working somewhere else?" She enquired.
Curious as to where this was leading, I replied to her. "I haven't thought about it, but that doesn't mean I wouldn't consider doing something different. I don't work here for the money, more for the company."
She smiled at my reply then leaned in a little. "I own a small private club with a select clientele. I am looking for a barista come barman to serve drinks to my guests and I think you would be ideal for the job."
Let us say." She hesitated for a moment. "Let us say you could be more your Natural self when working there, you are a submissive aren't you...boy?"
Her stare fixed me as I sat there in shock. I knew she knew that I was probably submissive, but to come out with it so matter of fact rocked me a little bit. I was intrigued and I just nodded me head dumbly.
"Errr, yes I am Ma'am." I felt a sudden sense of relief as I confirmed what she already knew. It felt like she had peeled away the persona I showed the rest of the world and was talking to the real me. I felt myself relax and slipped easily into my submissive mindset.
She just sat there looking at me, waiting for me to reply, I felt a little on edge but having piqued my interest I coughed nervously.
"I have to say I am intrigued and very interested in finding out more Ma'am." Feeling more confident in calling her by that honorific.
She smiled broadly. "Splendid. Do you have transport?"
"I do.. Ma'am."
"Good, pick me up here at eight sharp tonight." It was an order more than a request.
"I will show you around the club and discuss your duties further before you decide."
"Of course, Ma'am." The subservient tone in my voice more apparent.
"Now...boy.. you need to get back to your work, customers are waiting."
I looked around, suddenly back in the present and got up from my seat, giving her a little bow and got back to work.
I pulled up in my car at precisely 8 pm and I saw her waiting there, wearing a long coat and her high heels. Getting out of the car I walked round and opened the passenger door for her, the coat she was wearing although buttoned split from the hip as she sat and I instantly looked at a long expanse of thigh with just the hint of a dark band of stocking top as the dress she wore was much shorter than she would wear during the day. The sight sent signals directly to my cock and I felt it start to swell inside my black slacks.
Shutting the door and hurrying back to sit in the driver seat, I sat and took another look towards her legs but she had pulled the coat around her. Inwardly sighing that the sexy view had been denied me I started the car and set off, following her directions towards the club. As I drove, she started to explain to me about the club and my duties.
The club, 'Emilys' she explained was a private club that catered for lesbian ladies primarily, but bi-sexual ladies were most welcome there too. It was a place for them to relax and escape from the outside world and to help fulfil their desires.
My job would be to run the bar, to serve drinks and snacks to the ladies. Ordering and control of the stock, cleaning and keeping the bar orderly. All of this sounded good to me so far and I was looking forward to seeing the place, to appraise what I had already decided would be my new place of work.
I was directed across town and we eventually pulled up on the car park of the club. I switched off the car and got out and opened the door for Tilly, getting another view of her thighs as she got out. She caught me looking and gave me a knowing smile as I looked away quickly, embarrassed for getting caught.
I followed her across the asphalt, she swiped a card over the electric lock on the main doors and walked in. I followed behind her into a small lobby come cloakroom where she hung up her coat. She looked stunning in the short dress that she wore; it clung to her slender frame and emphasised her pert arse, her legs looked endless as she walked in front of me as she walked with ease on those killer heels.
I followed her into the main room, it was opulently furnished, with booths around the outside walls, tables and chairs that would be at home in a posh gentleman's club on the main floor. I could see the bar over to my left, it was quite large and took up most of the wall on that side of the room.
It must have only been a few seconds after I walked into the club and looked around when someone came out of a side door and walked swiftly over to us. A woman in her early to mid-fifties I would guess, her figure much fuller than that of Tilly but very curvaceous and looked hot.
"Hi Tilly!" She greeted my hopefully new employer. She strode across the floor, her hips swinging and full breasts bouncing and her hair, a mass of unruly curls that came to her shoulders softly moving as she swept across the floor.
