Enslaved Advisor

Note: This is my first story submission and many thanks to Literotica volunteer editor, mrwriterfromd, for his help with grammar, tense and general tips. I hope you enjoy it.

I sprayed a little aftershave and checked my hair in the mirror before getting out of my car. A week after our first meeting I was back to see Miss Smythe again, and as I walked up the path of a very well kept front garden I reflected on how a therapist could afford such a lovely detached house. I had asked her about what area of therapy she practiced in, yet she only replied to say that she helped clients find their place in life. I didn't quite understand what she meant by that, but she quickly moved on without giving me the opportunity to delve further.

She had recently contacted me as she was looking for a new financial advisor to look after her investments. As a wealthy lady that gave me the potential to earn very well, so I was delighted when she called to let me know she had chosen me, as I knew she had spoken to other advisors. She was also a very attractive woman in her early forties, thus the thought of spending time in her company was an added bonus to the money. Despite her good looks and super fit body, I had found her a little intimidating in our first meeting, and had got a little tongue tied on a couple of occasions. Being 15 years her junior she had that air of authority that took me back to my school days and my old maths teacher who could silence a class of adolescent boys with a couple of words and a glare. She would definitely have been the subject of many a schoolboy's fantasies.

I rang the doorbell and, unusually, some of the nerves that had me tongue tied in our first meeting came back. The door swung open, and Miss Smythe stood before me. If I had thought she was hot last week she had upped her game. She wore a white blouse which struggled to contain her ample breasts, and a tight fitting grey pencil skirt with her black hair tied back in a bun. She looked like the stereotypical female boss that you saw in porn.

"Hi Miss Smythe, good to see you again."

"Hello Josh, do come in. You can call me Jessica," she said turning around and walking down the hallway.

"Err, ok. Thanks Jessica," It felt a little strange calling her by her first name after the formal atmosphere of our previous meeting, but maybe now that we would be working together she felt it more appropriate.

I followed her into the hallway, closing the door behind me. We entered the lounge, and I noticed that the curtains were drawn, although due to the bright sun it was still light. I couldn't help but sneak a look at her great arse and shapely calves protruding below her tight skirt. I was definitely going to enjoy spending time in her company. She didn't have kids, but otherwise was the perfect definition of a milf.

"Thanks for giving me the opportunity to look after your investments Jessica, rest assured I will be working very hard to get you maximum returns." I was starting to feel good about this relationship already.

Jessica stopped abruptly and turned sharply to look at me. I hadn't previously realised that in her heels she was a good four inches taller than me, and now at less than twelve inches between us she could look down on me.

"Well, you had better perform for me," she said, looking me straight in the eye. I wasn't sure if she was simply being firm, or if she perhaps meant something more.

"Erm... err no, I mean, yes of course Miss Smythe. Jessica, sorry." I suddenly felt like I was back in a maths lesson!

"Is that a 'no you won't perform' or a 'yes you will?'" she replied curtly.

"Sorry, sorry of course I mean I will perform, I mean - make your investments perform," God, what was happening to me?

"Are you ok, Josh? You look a little flustered." she sneered.

"Yes, I'm fine." I insisted, "I'm looking forward to getting started with your investment and making you good money." My attempt at regaining composure was betrayed by a little nervous laugh.

We were still stood very close to each other; normally if someone had invaded my space as she had I would have backed away, but my feet felt rooted to the spot. Jessica really was a stunning lady and simply had this... aura about her. Was it my imagination or was there some sexual chemistry in the air? Perhaps that was just wishful thinking on my part?

"There's something we need to discuss before we start, just so we are both clear on the terms of this relationship," her tone made it clear that she was in business mode.

"Sure Jessica. I'm happy to clarify and answer any questions you may have."

"Your fees."

Well, she was straight to the point, and my heart sank a bit as that normally meant only one thing. I had already given her a generous discount as I had really wanted to work for her.

I tried to meet this head on, "OK, well Jessica, as I explained in our first meeting, the fees I charge are based on the services I provide, plus a percentage of your investment portfolio, which I have discounted from the usual rates. That was all laid out in the follow up email I sent you. I appreciate that it looks like a lot of money, but my quote really is very competitive, and you will get a great return on it."

I was happy that I had regained my composure and was sure that I was coming across confident.

"Well, the problem is," Jessica paused and looked me straight in the eyes with a fixed gaze, "that I don't pay men anything to do things for me. Men do things for me for free."

I waited for what she was going to say next, but nothing came. She just stood there with that alluring gaze. What was she saying? Was she offering me sexual favours in return for financial advice? I mean I would love to have sex with this hot milf, but I couldn't just gift my services for free in exchange for a fuck.

"I don't understand."

"It's quite simple Josh. I have a gardener, a chauffeur, a handy man, and a cleaner. They all serve me for free."

I had no idea where this was going, or quite what she meant by serve.

I laughed nervously, "Well, I guess you must have some very good friends. You are a lucky lady." I laughed again, but Jessica remained straight faced, fixing me with her glare.

"They are not my friends, Josh. They are my slaves."

What the hell did she just say?! I was shocked. Was she messing around, was this a joke? I really wasn't sure how to react, or what to say. Her features gave nothing away and she was starting to make me uneasy, and a little vulnerable.

"I'm not sure what you mean..." My mouth was going dry, and I felt like I was losing control of the situation.

"Well, I told you I was a therapist. I teach men their place in life." Jessica continued, "You look confused Josh, let me explain. I am a lifestyle dominatrix. Men pay me to let them be my slave. You, however, are in luck. I am offering you the same opportunity for free. Of course, you are expected to work for that privilege, which is why you will be managing my investments for free."

Now I was truly shocked, but at the same time, I could now easily see her as a dominatrix. I knew about the scene beforehand and have to confess to being turned on by watching some porn, but I had never met or visited a dominatrix. The thought had never crossed my mind. This was all very surreal, and I really should have just left and forgotten about the deal. Yet for some reason I was still rooted to the spot, looking up at Jessica.

"This is not what I want," I began, "or what I am into, Jessica. I'm not sure if you are winding me up with this, but if you and your friends play games then that is your business, but it's not for me."

"Slaves Josh!" she corrected.

"Sorry?"

"You said my friends. I have already told you that they are not my friends, they are my slaves. Don't you listen?"

"Yes, I do listen, sorry."

"You say sorry a lot, Josh. That's normally a sign of somebody who has low self-esteem. Do you have low self-esteem Josh? Do you often consider yourself not good enough?"

"No, I don't. Look, I'm sorry, I'm just a bit confused."

"There you go again, Josh. Saying 'sorry'."

"I'm just being polite, I don't know what you want me to say?"

"So, you want me to tell you what to say and do. That's what my other slaves want as well. I think you will fit into my stable of slaves perfectly, Josh."

"No, Jessica, it's just that", I hesitated, trying to find the words.

"It's just what Josh? Spit it out."

"This wasn't what I was expecting. I want your business, but all this talk is awkward for me and it's making me uncomfortable."

I was breathing heavily and was clearly flustered. I couldn't work out if I was nervous, embarrassed, or maybe just a little excited by being in the presence of this woman. There was definitely something intoxicating about her.

"Stop talking, Josh, and breathe slowly."

I did as I was told and tried to gather my thoughts.

"Let me explain something Josh. As I told you last week, I interviewed several advisors to handle my finances, and I chose you. Do you know why?".

Before I had a chance to reply, Jessica continued.

"I assume you probably think that it was your slick presentation, or your polite manner. Perhaps you even thought I chose you because I fancied you. You know, middle aged woman romping with a younger man. Did that thought come into your head?"

"No" I protested. "I am professional in my conduct and relationships."

"I told you to stop talking Josh." Her tone had suddenly changed, and she now sounded angry.

It took all my restraint to stop the word sorry falling from my lips again. I stayed silent and involuntarily bowed my head.

"Look at me, Josh, when I am talking to you," her stern tone was enough for me to raise my head and regain eye contact.

"I will tell you why I chose you. You were the most submissive."

What was she saying, submissive? That wasn't me. This woman was crazy, and I needed to leave.

"You look a little surprised Josh. You probably thought you came across as a confident man, but I could tell it was an act. I knew you were in awe of me the moment we met. Yes, I caught you looking at my breasts, arse and long shapely legs, but it wasn't all about fancying me. You were drawn to my natural dominance, and desperately wanted to serve me. That's why you offered such a generous discount without even negotiating. You just wanted to make sure you were back in in my presence. Isn't that right Josh?"

I didn't know whether to respond or stay quiet. Jessica soon made it clear what she wanted.

"Answer me Josh. You desperately wanted to be back here with me. You have fantasised about me, you know that I am a strong woman, and you like that. You just haven't admitted it to yourself yet."

"I, I want to help you with your investments." I replied, unconvincingly, "I like you, yes, but on a professional basis. Please Jessica, can we focus on the business? I just need you to sign the terms," I needed to get back in control of this situation, but I was simply making her angry.

"I've told you the fucking terms Josh. If you want to look after my investments, you will do so for free. You will also submit to me and become another slave under my control. Do you understand me?"

This was getting out of hand. I didn't know what to say or do at this point. As I was stood there feeling intimidated by this woman, my thoughts were all over the place. Before I had a chance to think Jessica made the next move.

"I am going to make this easy for you, Josh, by giving you a simple choice. You can leave right now and never contact me again. If you choose to leave, I will be making a complaint to your company about your inappropriate sexual advances in our first meeting."

"But I didn't! You can't do that!"

"Shut up, Josh. I haven't finished. I can and I will if you don't do as I say. The other choice you have is to get down on your knees and tell me that you are ready to serve me, to obey me, and do everything that I tell you to do from now on. With only two options it can't be that difficult for you to decide."

My mind was spinning. I knew I should leave, but I had been frozen to the spot ever since I got there, and I still couldn't move a muscle. Jessica was right, I was drawn to her in a way that I had never felt before, and I couldn't understand my feelings. What I did notice, however, was that I now had a hard on. I needed to leave, get out of there, but it was like I was under a hypnotic spell.

"Let me help you decide, I haven't got time for your procrastinating. You have ten seconds to make up your mind after which I will throw you out myself."

My heart was pounding, and I couldn't believe that I had found myself in this situation. My instincts told me to leave, but could Jessica really make a complaint against me? What would happen? Would I lose my job? Was she bluffing? I still had an erection and there is no doubt that, despite my predicament, I absolutely adored this woman. She was like nobody I had ever met.

"Ten, nine, eight, seven."

Jessica's counting was like a time bomb ticking in my head. Leave Josh, get out of there! I screamed to myself, and yet I remained still.

"Six, five, four."

Get out Josh get out! Just turn around put one foot in front of the other, you will be back in your car in seconds, and this will finally end.

"Three, two, one, times up Josh."

I think back to that moment, and even now cannot work out why I did what I did.

"Well Josh, have you made up your fucking mind? The door is right there. Go." Jessica barked.

That was the moment my life changed in an instant. It felt like I wasn't in control of my mind and body anymore when I sunk to my knees and found myself looking up at Jessica, a satisfied grin across her face.

"There you go, Josh. We both know you want this. It just took you a while to realise that. Now tell me, why you are kneeling at my feet?"

"I want to manage your investments for you for free."

"That's not quite it though, is it Josh? Tell me more, what will you become Josh?"

"Err... I will become," I knew the words she was waiting to hear, but couldn't say them.

"Come along Josh, I haven't got all day."

"I will become your slave, Jessica."

I felt a slap across the face that took me by surprise.

"It's Miss Jessica to you from now on, slave, and we need to establish some rules."

"Sorry Miss Jessica, it won't happen again," I said still in shock from the slap.

"It better not or your punishment will be more than just a slap across the face, do I make myself clear?"

"Yes Miss Jessica, I am sorry."

"Say it again," she demanded.

"I am your slave, Miss Jessica."

"That's better."

Jessica tugged my hair so that I was now looking up at her.

"You belong to me now. You are my slave and I own you. If you obey me and do as you are told, everything will be fine. Cross me and there will be consequences."

"Yes Miss Jessica, I am your slave and promise to obey you at all times."

Did those words just come from my mouth? What had happened to me? My life had changed completely in less than ten minutes, how could this woman do this to me? It was like she had some special power that put me completely under her control. The strange thing was, I was scared, confused, but also part of me was excited to be there, and I wanted to please my new owner and worship her.

"Good boy. I know you are submissive, and you will learn to serve me and see it for the privilege it is. I will train you on how to serve your Mistress and be a good slave."

I had no idea what was coming, but quickly found out.

"Stand up," Jessica ordered as she pulled me up by the hair, so I was up straight.

"Strip," was she serious?

"Sorry," another slap met my face.

"Obey me slave, or I will be forced to punish you," I had no idea what punishment she could dish out, but I didn't want to find out. I was now actually scared of this woman.

"Sorry Miss Jessica."

"You keep saying sorry. Stop saying sorry and start doing as you are told."

"Yes Miss Jessica."

I bent down and removed my shoes and socks, I undid my shirt and removed it, folding it and placed it on nearby sofa. I took off my belt, undid my zip and pulled my trousers down and placed them on top of my shirt. I wasn't sure how far to go with this so hesitated for a second as I stood in my boxer shorts.

"I said strip, slave."

I supposed this was going all the way, and so I slowly removed my boxers and added them to my pile of clothes.

I stood there stark naked and humiliated before my new Mistress, the lady who I had just promised to obey and serve. I still had a mixture of feelings going through my head but without a doubt there was a part of me that really wanted to be there, as evidenced by the boner that I was still sporting.

"Pleased to see me slave?" A wicked smile formed across her face. I suddenly felt pain as Jessica grabbed my balls and gave them a squeeze.

"These also belong to me now."

"Yes Miss Jessica."

To my relief she let go.

"Kneel," I quickly dropped to my knees.

Miss Jessica walked across to the sideboard and took something out of one of the drawers. She turned back towards me and slowly walked back to where I was knelt before her. I couldn't see what she had in her hands as she walked behind me.

"Hands behind your back," she demanded.

I quickly complied and felt leather cuffs being secured to my wrists. The thought now dawned on me that I now could no longer escape, even if I had wanted to. She moved in front of me and stood close, which was very arousing, which I suspected was her intention. She placed a collar around my neck that was attached to a lead.

"Up slave."

I got up as quickly as I could with my hands tied behind my back.

"Your training starts now."

With that she walked towards the door, pulling me by the lead. I had no choice but to follow. I was led into the kitchen, and towards a patio door at the back of the house. She slid the door open and stepped outside. She tugged on the lead as I hesitated to go over the threshold. My slight delay was a combination of feeling a little unsteady stepping over the threshold with my hands tied behind my back, but also the horror of realising that I was now going to be outside and potentially in view of neighbours.

I quickly tried to recall how close her neighbours were and what view they had into her back garden. My heart was pounding now, and I felt so exposed and humiliated with the situation that I found myself in. We headed towards an outbuilding about 10 metres away across a very well-kept garden. Her gardener was obviously doing a good job of serving his Mistress. Miss Jessica was quiet and didn't look back at me, she just kept pulling me along by the lead. If people could see us, she was not concerned. We reached the outbuilding, and she pulled me by the lead so that I was now in front of her facing the open door.

"Welcome to your training academy, slave. This is where your training begins, and you will surrender yourself to me completely in every way. I will own your body, your breath, your mind and your cum. I will control it all."

Suddenly I felt a hard shove in my back as I was pushed forcefully into the building, nearly stumbling as my hands were still bound behind my back.

"Haha, it's not so easy keeping your balance without your hands is it," she laughed.

"Now get down on your knees slave," she ordered, "Your new life starts now."

"Yes Miss Jessica," I knew I was beaten by this lady and powerless to resist her, I was an owned slave now, and my new life was about to begin serving my new mistress.

The end.