After people get beyond the novelty of talking with a former sex worker and I answer all of the questions that I did in my last post, the thing I most often get asked about is how it is possible for me to create connections with people right away.
In the context of the work that I did for Mistress Simone, this was trivial. I already had a certain amount of native talent in the area. I was fit, good looking, well spoken, and I have a fucking amazing voice. The people that I saw were already primed and seeking a connection – all I had to do was not fuck it up. Of course, I still sometimes did – and not being an idiot, I try to learn from my mistakes and do better the next time, or at the very least, make new mistakes.
All of those first-date like meetings served to teach me rather well in how to create a connection and how to maintain someone’s interest once I do. As a result, I’ve created the neural pathways to instinctively know how to attract and maintain the attention of almost anyone.
I don’t necessarily mean a romantic or sexual connection here – and it would be impossible for me to create such a connection with anyone, since there are at least a large number of people out there who would not find me attractive – at least, not right away. But even when you are not taking sex into consideration, it is often very useful to be able to establish a connection right away, even if it is shallow. This is a core skill for salesmen, or personnel managers, or product marketers, or just about anyone, actually.
People are already hard-wired to look for connections. Humans are social animals – without a clan, we die – and when an opportunity arises to meet a new person, you make a snap judgment – whether you want to admit it or not – about how you feel about that person. Is this a person that I want to fuck? Is this a person that I want to talk to? Does this person make me feel threatened, or does this person make me feel safe? I can almost guarantee that all of those questions are going through your mind about every new person you meet, every time you meet someone new. You may not be cognizant of them all at the moment you meet, and the answers to those questions can (and do) change – often quite quickly – but every person answers all of those questions, and dozens others besides, about every person they meet, within moments of meeting them.
The good news is that most people are actually pretty decent people, and that most people really do want a positive outcome to meeting anyone. That does not mean that everyone wants to fuck you, but it probably means that more of them do than you realize.
The worst part of this post is coming right now: there is a trick to it.
It’s not something that I started doing intentionally, but eventually I noticed the effect, and I can occasionally be something of a social scientist brat – so I performed experiments. I talked to my friends in new ways, I talked to their friends and watched their reactions intently, and I interacted with total strangers.
It’s actually much harder to do this in the context of a normal social club/bar/party setting than it is as a contracted sex worker, but the stakes are also a lot less and I really didn’t care about being rejected – I was inoculated to rejection when I was a younger, more instantly visually appealing man. Which is to say – I’ve been rejected a lot…
But I said there is a trick, and it would be really mean of me to mention it and not tell you, wouldn’t it? So here it is: if you want to create immediate connection with someone, no matter their gender, age, or motivation, the answer is always the same…
Make eye contact and smile.
Seriously. That’s all that’s needed. Most of the time, you get a smile back and then you can move to the next step, but often you will get a shy look away or a terrified turn of the head or even see them get up and run away. Don’t worry – you’ll get another chance, but there’s also the chance that they just don’t like what they see and you should give up.
If they look away but eventually look back towards you, you can try it again one more time – but more than that and you are being creepy and need to stop. Otherwise you’ll ruin my reputation. More often than not though, if you don’t stare at them and try to will them into talking to you, they will be intrigued by the non-threatening smile and return their attention to you and give you a better chance – but it’s a bold thing to hold someone’s gaze who isn’t expecting it, and it intimidates a lot of people at first.
The next step – and the crucial one, I’ve found – is to ask them for a favor. It has to be something trivial that they can complete without needing any skill in a short period of time, and it cannot be in any way sexualized. Anything creepy here is going to just push them away and tickle their ‘not okay’ vibes. Besides – you’re not in this for the sex anyway, because if you were, you’d be smart enough to realize that the best way to accomplish that is to just pay for it.
This will require you to actually think a bit, perhaps, but as a good example, imagine that you saw an attractive, clean-cut, non-threatening looking man smile at you and give you some time to react, then he gets close enough to ask a question and says, “Would you mind holding my drink for me for a moment? I’ve just noticed that my boot is unlaced and I’d like to fix it.” Then he hands you his drink.
Most of you are thinking, “well, now I roofie him and when he’s good and lit, get him to take me back to his place where I fuck his brains out and then roll him for any cash he might be carrying on my way out – hoping never to see him again.”
No.. wait.. That’s not what I want – and that’s only happened once…
But you do see the point, right? You’ve created a connection, immediately. You’ve engaged their compassion as well as curiosity and maybe lust.
But isn’t this all terribly manipulative and premeditated and awful, Rant? How is this different from any of that pick-up artist crap that you are always shitting all over? Aren’t you just using psychological tricks to manipulate people?
Well – maybe. But name any interaction that you have with anyone, ever, where there is not some form of manipulation taking place. The whole point of communications is usually that there is something that I want (even if it’s pretty mundane) and I want you to help me with it in some way. And more to the point – you do have to start somewhere, and while I could just stand next to someone until I hear something that I can talk about and then try to jump into the conversation… that is a really weak place to start, putting yourself in the submissive position before you even begin to communicate – verbally, at least.
By asking for a trivial task to be accomplished, you’re giving your conversant the power to say ‘no’ and walk away, or to pick up the gauntlet and do something trivial in the interest of more conversation. And conversation is the goal here, so you have to follow up after this and actually have something interesting to talk about. There must have been some reason you wanted to talk to this person. Maybe you overheard them talking about something you are interested in, or maybe you just really like the way they make that dress look and you want to fuck their brains out. Talk about it – whatever it is – or let it go and forget about it entirely.
Interesting – or perhaps the opposite, actually – is that this works equally well with people who are sexually attracted to me as those who are not. In either case, I’ve engaged their curiosity and given them a focus, and then all I have to do is hold it.
Of course – you must also be charming and debonair and have impeccable sartorial choices if you want to maintain this contact, and that becomes a much more involved process and there are no tricks for that – either you will establish a real connection, or you won’t – but that is entirely up to you. The vast majority of the work involved in making a new connection is in those first moments of uncertainty, and by looking for a smile and asking for a favor, you can short circuit a lot of that.
That’s the question I get more often than anything else. It’s a part of my past, and there are posts about it here on this blog (starting here, and then going through parts 2, 3, 4, 5, 6, 7, 8 – and more to come) but once people learn that I used to be a sex worker, that is the question that I get more than anything else…
What was it like?
Well – it’s not really an easy question to answer… I could come up with some suitable metaphor if I spent a moment trying to do so, but that would only give you a part of the answer, and the real answer is quite complicated.
It was different things at different times.
In the beginning, it was fucking awesome… literally and figuratively.
Oh sure, I was terrified at first, but once I got over that and sort of jumped into it with two feet, it was really pretty amazing for awhile. Though eventually I started to become unhappy. I had no control over my own schedule, no choice in who I saw, no vacation days, no benefits, and while partying all of the time can be great for a while, eventually I started to burn out and then I just wanted to be a real boy again.
And this is where I start getting interrupted with questions about specific things…
Did you ever have to have sex with a client that you didn’t find attractive?
No – not really. I worked for what amounted to a high-end brothel that operated right under the noses of everyone around, and maintaining such an enterprise required a lot of money, so my Mistress (Simone was her name) charged a lot for my time and kept the client list pared to those that properly fit in with her aesthetic. I am still not 100% sure that I know what that was, but nearly all of my clients were married women in their 30’s and 40’s, and they tended to spend a lot of time and money on their appearance. They chose me not because I was younger/hotter/better than the men they could get – almost any of them could have easily found sex for free in the wild, but they were paying for discretion and often for a very particular set of interests.
It did happen that I would have to see clients at times when I was not particularly “in the mood”, and unlike my female counterparts, I did not have the option to just lube up and lie there, so I learned all about pills and creams and pumps and rings, and I employed them all from time to time.
But did you ever have to have sex with someone who was just fat or ugly?
No – I had clients who were overweight by society’s standards, even obese in some cases, but I would never classify someone as fat unless it was a name they claimed for themselves, and the only ugly I ever see is the kind that stains a person’s soul – and has nothing to do with their body.
Did you ever have sex with men?
No – or at least, I don’t think so… I was offered money to on several occasions – sometimes it was quite substantial, but trauma in my past has always prevented me from being sexual with men – at least from the active position, and if I were ever used as an inactive participant, I was not present for the act.
I used to be adamant that this never happened, but I get glimpses of memories that make very little sense otherwise, so I have to wonder what I don’t have full memories of…
There was certainly a time where I could not conceive of the possibility that this may have occurred, and I will fully admit that even writing these words causes a spike of anxiety for me, but in retrospect it really makes very little sense that I never saw male clients.
I was certainly involved in several group-sex scenarios where men were present. I can remember those pretty clearly.
Where is the most interesting place that you have had sex?
Interesting is such a strange word… but my answer to this question is actually pretty easy, and it has nothing at all to do with my life as a sex worker.
I had sex in the confessional of Saint Mary’s Cathedral in San Francisco. The only thing that would have made it better is if she had been wearing a nun’s habit when we did it.
I know.. I’m a blasphemous devil who will burn in hell for all eternity…
I’ll keep the lights on for you.
How much money did you get?
Not as much as I should have… this is not to say that I didn’t ‘sell’ for exorbitant prices – my time went anywhere from $200 to $700 an hour, depending on duration, activities, and when in my ‘career’ I was engaged. However, Simone managed and held the money in almost every case. There were a few outcalls where I would be expected to collect the fee and return with it, but more often than not I saw people in the apartment that Simone provided for me and she handled the money before they ever arrived at my door. She covered my expenses, kept me clothed and fed and housed, and gave me chunks of cash from time to time with the idea that I would use it to splash out and have fun of my own. It probably contributed to some of my idiosyncratic spending habits now… all of my day to day expenses were handled for me and I didn’t have to worry about them, and while I did have bank accounts and credit cards of my own – for the most part I always paid cash for everything and carried large amounts of it.
I honestly have no idea what my income was for the not-quite-two-years that I spend under Simone’s direction, but as I was her property, I didn’t decide many things and I didn’t really keep track of what I did.
I probably spent close to $50k in cash across the time I was with her, and my expenses probably ran close to $100k per year, but I was living at a much higher standard of living than I would have chosen for myself and didn’t have much choice in the matter.
All told, if I had to do some diner napkin mathematics to guess at the totals… I probably cost Simone close to $200k per year, and I probably earned her about 3-4 times that, quite possibly more.. Most weeks I ended up with appointments for at least 15 hours – sometimes as much as 50 – but those were generally inclusive of longer sessions with discounted rates, so I’m not quite sure how it evened out.
The important thing to realize though is that I never really got to keep any of that. Perhaps I could have been more responsible and pocketed or even deposited some of the cash that I was given, but I tended to spend it – just as Mistress Simone had instructed me to do, and often at the places where she instructed me to do it. But it was not all bad – she took me shopping somewhat regularly and put me in expensive clothes (that I also didn’t get to keep) and generally kept me up well – I just had nothing to call my own, not even my body, and I viewed it all as normal and expected.
Did you ever have sex with any famous people?
Depending on how famous you are asking about.. yes, but no one on the A-list or anything like that. More often they were important people than famous people.
Who were they?
I’m not telling you that.
How many clients did you have?
I had several regular clients who I would see on a regular schedule – or sometimes an irregular schedule, but I also saw a lot of clients only once. I’d say it was close to a 50/50 split between clients that I saw only once and clients that I saw more often than that. Some of them would see me at the same time every week – almost like going to see a therapist or a chiropractor, and I suppose I served a very similar function to some of these women.
All told though, I don’t really remember how many it was over the span of my time working for Simone. I tried to stop counting at 150, but ended up keeping track up to about 180 and then I really did lose track.
What was the weirdest session that you had?
There were a few that stand out, but I do think the mother/daughter doubles session that I had was probably the strangest. The mother of the pair was a regular client of mine, and her daughter was a purported virgin at 26 and that was apparently a problem for both of them. I would honestly have had no qualms at all about seeing the daughter in a separate session, but her mother brought her along to hers and was present the entire time.
I did not end up interacting – physically – with both of them that day, I only interacted physically with the daughter while the mother watched and provided commentary and instruction – to her… it was all very odd.
Did you ever have a problem ‘getting it up’ with a client?
Yes, I did, but it was not frequent – and it was almost always because I was pushing my body too hard rather than anything else, though I can occasionally get in my own way, psychologically, as well. I had a pump that I could use if I absolutely needed to have an erection, and strangely enough – even though I suspected that it would cause problems, it almost never did.
There are exceptions, of course… and I was punished for those.
Did you always have sex with your clients?
We always performed some sort of sex act, yes, but it was not always penis-in-vagina sex that was happening. I had one regular client, in particular, who would visit me at the same time every week and have me spend her entire hour just going down on her as she climaxed over and over again. We almost didn’t even speak about it. It was all very utilitarian, but she would usually orgasm around 20 times in the hour.
Some of my female colleagues would talk about their clients who would just want emotional intimacy and often only limited physical contact, but I never had a client like that.
My theory is that the women who would come to see someone like me had already made their choice and were not going to be dissuaded by last-minute cold feet that affected many of the men, or that the men sometimes rationalized things… right up until it came time to make the action that would be the point of no return in their mind. The women had already passed the point of no return before they walked through my door.
Did you ever get asked to do something you didn’t want to do?
Sure – that was pretty frequent. Most of the time I had to do them anyway, but sometimes I was allowed to say ‘no’.
Okay – what kinds of things?
Well – I was not terribly keen on the mother/daughter virgin team that I talked about previously, and there were some of my clients who really enjoyed degrading me or physically causing me pain, and while I found that I could lean into the physical pain, my reactions to the degradation were all over the place and never positive.
Did you ever fall for a client?
No – though I did have clients fall for me.
I was emotionally walled off from the ability to care for anyone other than Simone at that time of my life. She was my world, and everything I did was to please her.
Did you ever run into clients in ‘the real world’? And if so, what did you do?
Yeah, I did – though rarely.. The places that I would go to socialize catered to a different caliber of folks than the pool of people from which Simone’s clients was taken.
If I saw someone who I recognized from the job, I would pretend that I didn’t know them, even when one of them once made the mistake of recognizing me and then perking up to start to say something, realizing the company she was in, and then didn’t know how to handle things. I told her politely that she must have made a mistake and that I have ‘one of those faces’ that everyone finds someone recognizable in. It helps that that is actually true.
I have been asked other questions, of course, but these are among the most common. If you have other questions that you would like to ask – I respond to emails as quickly as I am able, and you can always write in the comments section as well. I will do my best to answer anything you ask.
Mistress Simone was confusing – at times she seemed entirely without compassion. I do not know the full details of her operation, and in retrospect, that is a very good thing, but I did catch glimpses from time to time – especially when she left town on one occasion after I’d been in place for a few months and I took it upon myself to look after what I could – in an ill-fated attempt to impress her. I do know that the weight of keeping things running smoothly got to her from time to time, and I do know that anxiety was one of her demons as well.
But sometimes, she was incredibly caring and empathetic. She seemed to always know what was going to happen before it did. She not only seemed to know the specific details of what would occur, but she seemed to always know how I would feel too. There was brief period of time where I entertained the notion that she could actually see into the future, but that wasn’t it at all, she was just a master of understanding the human condition, of reading the desires of people and finding ways to fulfill them. It was as skill that she attempted to impart on me – and one that I would like to think that I have become adept at myself.
On this particular occasion – I didn’t even know that I needed support, but Simone did, and she was there for me.
I had just met with my first client, Mary, (the details of which you can read about here, if you wish) and it had gone amazingly well. Subsequent meetings with other clients, and even with Mary herself, did not always go so well. I was very fortunate to have had the first time experience that I did – something which I suspect Simone had specifically engineered, but I do not know for certain, and as I said, Mistress Simone was often confusing.
I was confused to see Mistress Simone when she showed up at my door after I’d run around tidying and getting clean after Mary had left. I was certain that I’d done something wrong to earn her visit, but she had something else in mind.
She walked into my apartment, looking stunning as always, and not knowing what else to do, I dropped to my knees in front of her. She looked at me, but walked past me to go sit at on the edge of my bed and placed her hands to her sides at the edge and regarded me.
“Rant. You did nothing wrong. Stand up and come over here with me…”
I stood up and walked over to the base of the steps below where my bed was. Even sitting as she was, her head was level with mine as I stood below. Not knowing what else to do, I stood there at parade rest and regarded her. She was dressed more casually than I was used to seeing her, in a lengthy flowing skirt and a loose-fitting top. Normally, her clothing was tight, fitted perfectly, or she was wearing little more than underwear, but now she looked … ordinary. It was unsettling.
“How did it go?”
I wasn’t sure how to answer. I felt like it had gone very well, but was considerably less sure of that after being visited by Mistress Simone. I began to go over events in my mind, disassembling them and looking for all of the points of failure along the way. I was about to answer with a list of perceived faults, when Simone interrupted me.
“No, don’t answer now… It’s okay. Come, kneel at my feet, toy.”
I did as she asked, stepping up onto the platform where my bed rested, and knelt to the right side of her. She scooted over a bit to the right and centered herself around me, and then spread her legs and motioned for me to come closer, so I knee-walked until I was kneeling between her legs, and then she patted the inside of her thigh and I somehow knew that she wanted me to rest my head there, so I knelt lower, and then rested my head on her thigh as she began to pet my hair.
Mistress Simone’s skirt was split up the sides, which is something that I didn’t really notice until she sat and spread her legs, allowing her bare thighs to protrude from the sides, one of which my face was now pressed against as I tried to look up into her face and she pet my hair, which invariably caused my face to turn towards her body – and her pussy – instead. At first, I kept trying to crane my head up to look into her face as I lay there, my whole body tense with the weird angles required to accomplish such a thing. Once I started to say something, to ask my Mistress questions about what she wanted from me, what I should be doing, because to just be kneeling there, leaning against my bed and her thigh, having her pet my hair, was making me anxious. I felt like I had done something to displease her, I thought that I should be doing something differently…
Opening my mouth to speak the questions that were flooding my mind, I changed my posture slightly, and it became clear that despite her silence, Mistress Simone was watching me intently, because the moment that my mouth began to open, she shifted her hand from petting me, to wrap around my jaw and gently push my mouth back closed. When she moved her hand away for a moment, I began to open my mouth yet again, and she repeated the same action, with the same levels of both deliberation and tenderness. Once again, she moved her hand away, and when I did not try to open my mouth again, she resumed petting my hair. I still had no idea what to do, and my anxiety was making me restless. I shifted in my position on my knees, and when I moved, Mistress Simone’s hand would stop.
After several minutes of this – what seemed like an inordinately long period of time – I eventually reasoned that she wanted me to just relax and be there, kneeling loosely, head on her thigh, with her petting my hair. Eventually, I did just that, letting go of the tension, relaxing into my lean against the bed and her thigh, allowing myself to feel the comfort present in her strokes of my hair.
My breathing slowed, I could feel my body temperature dropping, and the anxiety that I had been holding on to – all afternoon at least, perhaps all day – finally began to flow out of me. I felt grounded for the first time in a long time, peaceful in a way that I had only experienced a few times in my life before, and those were all what one could only properly describe as ‘religious’ experiences. It may be the closest I ever really came to feeling in subspace myself, and perhaps it actually was, but it was fleeting, and replaced by the most unexpected of things for me at that time.
I began to cry.
I don’t mean that I sat silently as tears streamed down my face as I am oft wont to do today, nor that I was overcome by emotion to the degree that I commonly see in people when they try to hide their tears from me. This was crying of a primordial sort. A part of me broke in that moment, and I sobbed. Eventually, it became impossible to stay as I was, the sobs causing me to curl into a ball at Mistress Simone’s feet, uncomfortably straddling the top step up to my bed and the floor in front of it.
I don’t know for how long I cried, and I don’t know for how long Mistress Simone petted my hair and wouldn’t let me speak before I began to cry, but I was on the floor crying for what felt like a very long time. I could not control my body, and I must have looked a fright with tears and snot when I finally did look up again to note that Mistress Simone was no longer sitting on my bed. I pushed myself up to look around and noticed Mistress Simone in the kitchen area, working on something as I glanced over to the clock to see that about an hour and a half had passed since she arrived at my door – significantly longer than I was expecting to find, even though it had felt like a long time to me. In retrospect, I wonder if I didn’t fall asleep for a short time somewhere in between beginning to cry and looking to see Simone no longer above me.
I completed pushing myself up into a sitting position on the stairs where I could see well into the kitchen and my senses began to return to me. I cleaned the snot and tears from my face as best I could with my hands and the ends of my shirt and focused my attention the smell, sound, and sights from my kitchen.
Mistress Simone was in my kitchen, cooking. It was something that I never expected to see, and something that I would never see again. She looked over at me and smiled – which was also something that I did not often see from her.
“It’s funny how the smell of breakfast food always seems to bring the attention of the exhausted and the forlorn,” she said in my general direction as she was plating the eggs that she had just been cooking and putting the mixing bowl and pan in the sink for me to clean later.
She pushed the plate across the island towards me and indicated it with her hand as she said, “Rant. Eat. Please. You need the calories and comfort.”
I wordlessly rose to walk over to the place she indicated, pulling a bar stool over to sit on as I did so. I settled onto the chair and looked over at her, unsure of what I should be feeling, of whether or not I was doing the right things, worried that my emotional outburst was going to put me on the outs with her, thinking about three hundred different things all at once.
“Stop,” she said, reading the anguish on my face. “Just stop, Rant. You have done well today. You have done extremely well. I am pleased with you today, and I am certain that this will become easier for you with time.”
I instantly felt relief. I was still emotionally raw, and I still did not really understand what it was that I was feeling or why I was crying the way that I was, but I did at least know, in that moment, that I had not displeased her or somehow screwed up, and that was enough. The relief must have been obvious in my posture, face, and voice as I looked up again at Mistress Simone and asked her, “How did you know?”
“I wasn’t sure what to expect, honestly. Every person is a little bit different. What you just went through was an intense experience to cap more than a week of increasingly intense experiences, and it would be surprising if you didn’t show any weakness anywhere along the way.”
That word. Weakness. It took the wind right out of my sails again, and it was probably evident in my posture because it was immediately rebuked in compassionate, but certain terms, “Rant. Stop. You must not let every minor nit turn into a major upheaval. I gave you your kudos, and I will continue to do so for now, but while this episode was understandable and will be excused, you must not let yourself get carried so far away again, do you understand?”
“Now eat your eggs. I’m not much of a cook, and I can count the number of times I’ve cooked for a man – my husband included – on the fingers of one hand still, but you have performed very well and I am very proud of you and you deserve something special.”
“Thank you, Mistress,” I said with ecstasy as I began to dig in to my eggs. It was only then that I recognized that there was no other plate; that Mistress Simone had cooked for me in my own kitchen, and only for me. It was not that she intended to eat and was allowing me to have the surplus of her portion, she was doing this as a service to me, and it felt strange and wonderful all at once.
The eggs were not particularly good – simply scrambled with some salt and pepper, but the method in which they were delivered ensured that they were among the very best that I had ever had.
“These are delicious, Mistress,” I said, with complete honesty.
“I do expect flattery and devotion, pet, but I will not tolerate dishonesty – you are not being dishonest with me, are you, toy?” she asked me, with just a hint of a smirk.
“Oh, no! I swear, Mistress! I don’t even like eggs, and these are amazing!”
“You don’t like eggs, and yet, these are amazing?”
“It’s a good thing that you’re adorable, Rant, because sometimes the shit that comes out of your mouth is just completely unbelievable.”
“Nevermind. It is not important. I am pleased that you are enjoying them, and more pleased that you are eating them.”
“Please be sure to drink lots of water,” she said as she grabbed a glass and filled it from the tap to place in front of me, “and do not get used to this sort of treatment. I expected you to have an emotional reaction, and you did. I expected you to do well with Mary, and by her accounts, you did – though we will talk later about what you should and should not reveal to my clients. I expected you to be just as you are, and I was not disappointed.” She said the last with an air of finality to it that left me feeling a little off-balance.
“Thank you, Mistress,” was all I finally managed to get out, after what was probably too long a period of time to be comfortable for either of us.
At this, Mistress Simone gathered herself up, stood taller – though I had not noticed that she was not keeping her normal, extremely rigid posture until just this point – and looked me square in the eyes with the largely unemotional gaze to which I became accustomed.
“I will leave the dishes for you to do, Rant. I am glad that I was able to give you this time after your client today, but this is not likely to be something that can happen again. You will need to be able to be resilient and care for yourself moving forward. Do you understand, Rant?”
“Good,” she said as she walked to the door, grasping the handle and looking back at me before opening the door. “You really did do well today, toy. Keep this up, and I foresee a long and fruitful partnership.”
“Thank you, Mistress,” I beamed at her as she opened the door and disappeared behind it.
I sat there, on the barstool, in front of an empty plate and an empty water glass for quite some time, examining the thoughts and feelings and visuals that played themselves over and over again in my mind, wondering at the sort of partnership that Mistress Simone was speaking of, and wondering at my own emotions and whether or not I could continue to do this. But ultimately, I decided that I could – I could do anything – for her.
I still don’t really know what possessed me to do so, but I pulled all the bedding off of my bed and slept in it on the floor that night. I remember waking early in the morning hours, having forgotten to close the blinds the night before and with the glare of morning coming in. I remember feeling like I was completely alone in the world, with no one beside me apart from Simone – but in that moment, that felt right, comfortable, even good.
My schedule was clear for that day, but that would be the last day that I had to myself for a very long time afterwards.
To my readers: I apologize for the length of this piece. I normally try to keep my entries to near 1000 words, and I began with the intent to do so this time as well, but as the story developed on the page I found that I could not tell it with so few words and so I chose to cull far less than I normally do.
I have never lived in as nice of a place as I did when I was with Simone. I have no idea how much such a place cost, but it was well beyond my means at the time and is almost certainly beyond my means now – though it would also be impractical today for a number of other reasons.
It was a very modern loft style studio apartment. There actually was a small loft area reachable via a staircase that was above the entryway of the apartment, but walking in the first thing you would see is the kitchen island, then the windows, then the St. Andrews cross in one corner, a telescope in the other corner, a dining table and chairs, a small sitting area with a love seat, overstuffed chair and a low coffee table, and a raised dais upon which was a massive (though not as large as my current) bed.
It was a really nice kitchen – I wish that I had had the confidence and knowledge of how to cook back then because I’m certain that I could have made some very nice meals in that kitchen, and probably could have provided even yet another service to my clients, although in all honesty most of my appointments were too short for that to be viable.
However, my very first appointment was to be for a duration of four hours. I was more than a little nervous about this. What am I supposed to do for four hours? I mean, I was young and in great shape and athletic enough to know how to be at peak performance, but four hours is a long time and I was envisioning trying to actually be physically active for that entire time and not only finding the duration daunting, but I was not at all sure that I would be creative enough to fill that much time, and I like to think that I’m pretty creative.
Every client that I saw was scheduled through Simone’s office. This was both a good thing and a bad thing at various times. It was a good thing because everyone that I saw was a known quantity – vetted and approved by Simone or someone on staff, they tracked my schedule and made sure that I was never overbooked, but they often left me literally no time for myself. I never had clients scheduled closer than an hour apart, but because of the nature of the business, not everyone leaves precisely on time, and late arrivals have an expectation of being allowed to make up that time on the back end. However, there was a protocol in place to deal with these sorts of things, with the aim of accommodating a certain level of uncertainty baked into the process. For clients that I would see away from my apartment (outcalls) there was a different procedure, but for clients that I would see in my own apartment (incalls) – which was the vast majority – there was a security door with a buzz-through system for the building. Clients would know to buzz me and give a certain name and then I would buzz them in and meet them at my door as would be appropriate for the appointment.
Before each client – time permitting – I was given a dossier of sorts on the client, any special requests, known preferences, and a little bit of personal information about them as a way to relate and have something to talk about. Despite the obvious and intensely personal nature of the visits, most people are not completely comfortable just jumping into sex right away with someone that they known nothing about apart from some pictures and a little bit of back story. Of course – some are…
In the information that Simone gave me about my first client, Mary (which wasn’t her real name), she said that this was one of her best clients and a personal friend besides, and I was to give her anything that she wanted. She had interest in horses, travel, fine wines, and finding new young artists. Well, at least I knew something about horses, and I thought I knew something about wine too – but it turns out that some wines are made outside of California, and I was not very familiar with anything else at the time.
Mary was not a Domme, and had some interest in kinky play, but was mostly interested in very physical sex acts – the more physical the better. I was to act in a confident and physical manner with her, but not to command her to do anything or to engage in any sort of non-sexual play. She liked to be taken, but only on her terms. Even more than that though, she liked to be aggressive herself and have that met with equal aggression. I was to be deferential while simultaneously making her feel like I was not.
How the fuck was I supposed to do that?
In the hour or so that I had before she was set to arrive I think I must have walked every inch of floor in that apartment, adjusted the music that I was playing about 20 different times, trying to figure out what sort of music would best accompany physical sexual acts with someone who I knew next to nothing about – not even how she looked.
With the exception of regular clients who would return multiple times, this was often something that I would have to contend with as I waited for a new client to arrive. They all knew exactly what I looked like, of course, having picked out my profile in a catalog of such things that Simone kept, but I rarely had any idea what they would look like and the amount of information that I was given about Mary was generally greater than I would see in most cases.
Attraction, being what it is, would mean that in some cases, I would be worried that I would not be able to perform to the client’s satisfaction – and prior to sitting there in my anxiety around meeting my first client, this was not something that had ever occurred to me.
Would I be able to get it up? Or perhaps even worse – what if I couldn’t keep it up when I needed to? Having already been on the receiving end of punishment from Simone, I could only begin to imagine how things might go if I were to fail to perform as required. There were some things that were available to me to help with this, but I would not find that out until later and for this occasion, I was left very much in the dark.
As I was pondering my potential failure to perform, my phone rang – which I was certain was from the buzzing at the door and I looked at the clock to try to understand how the time had passed so quickly and I realized that I should still have 20 minutes, so I picked up the phone and spoke with more question in my voice than anything else.
“Rant. Mary will be there soon. Are you ready?” Simone’s clear, concise, and somewhat cold voice came through strongly and I must have verbally exhaled my apprehension because she followed up immediately with, “Kneel for me. Now.” To which I responded by getting on my knees.
“Rant – are you there?”
“Are you kneeling?”
“Are you breathing?”
“Tell me ‘no’ so that I know your brain is still working.”
“What did you just say to me? Are you allowed to use that word with me, Rant?”
“No, Mistress. I mean, yes, wait… are you trying to make me more nervous?”
“<soft chuckle> No… Mary does enjoy intimidating her partners sometimes, but I want her to like you and she’s not going to respect you unless you give back everything that she dishes out. Can you do that, Rant? She will not make it easy for you.”
“Yes, Mistress.” I said, but I was much more nervous than the words that I spoke.
“Good boy. Now do me proud.”
I held the phone receiver in my hand and knelt on the floor for about a minute more, until the loud cycling tone to alert me to it being left off the hook began, which shifted me out of my reverie and made me realize that if I didn’t put the receiver back down, the door buzz would not come through and I could be in big trouble.
I had to stand again to replace the phone receiver, but once I’d done so, I decided to kneel again, thinking about everything that had come to pass to that point.
It was one of the more nerve wracking things to have happened in my life.
What seemed to be at the same time an eternity and merely a moment later, my phone rang again and I looked at the clock again and confirmed what I already knew to be the case – it was time for Mary to arrive.
“Hello – I’m looking for Rant.” spoke a very pleasant sounding female voice.
I’d been told what to respond. “You have found him. Please come up.” I pressed the ‘*’ key on the phone, heard the tone, and then hung up the receiver as I walked over to unlock and stand near the door.
A few moments later, I could hear the steps on the walkway outside my door and I tried to look through the frosted glass near the entrance, but only saw colors moving and then remembered the peephole in the door and looked through to see a distorted image of a gorgeous woman walking towards my door.
I stepped back just before she began to raise her hand to knock on the door. I recall internal conflict as I tried to decide whether or not it would be a good thing to open the door in advance of her knock, but ultimately the decision to let her knock and the inaction of trying to make a decision coalesced and I heard:
<knock knock> confident, not tentative in the least…
…it was enough to cause me to hesitate further, but eventually I pulled myself out of my head and opened the door.
On the other side of the door I saw one of the more beautiful women I have encountered in my life. She was tall, but still shorter than I am, athletic, busty, blonde, and she had the biggest brown eyes I’ve ever seen. Her makeup was understated but worked to alter her apparent facial structure, which was rounder than she probably would have liked. She reminded me a great deal of Drew Barrymore in her appearance, and she was wearing a short sundress and sandals: periwinkle with white polka dots.
I suspect that she was looking me over in much the same way that I was her, because she stood for a moment in the doorway just looking at me, and I quickly realized that I was both blocking her way and had failed to invite her in as yet, so I quickly moved to the side and gestured into my apartment with my arm as I said, “Please, do come in.” She moved past me, and I closed the door, turning to walk past her and into the open space of the apartment.
It requires a little bit of mental gymnastics to recall details of that day, but when I do, I am continually surprised at how immature I was in my sexual expression. The mainstays of my sexual expression today – raw physicality, breath play, growling, biting – were mere shadows of what they are today. Mary actually helped me to develop these skills. She was hardly the only one – and I have gone through periods of contraction again since then – but I will always have something of a special place for her in my pantheon of elder sex gods.
I could see and feel the hunger in her eyes. I felt invigorated by it. All anxiety that I had about being unable to perform was instantly gone as my own sex drive engaged again and I began to mentally undress the woman in front of me.
She stepped further inside and maneuvered herself to position me between her and the kitchen island and then she started to advance on me. It did not happen quickly, but she did it with such fluid predatory movement that I was still caught off guard and allowed her to get much closer than I realized, backing me into the kitchen island as she approached.
Her look was playful and predatory at the same time. She casually reached up and touched me on the chest, following her arm with her body, pressing herself into me, pushing me into the island behind me, and then she reached down and grabbed my cock through my slacks.
I’m pretty sure that I twitched. I liked it, but I twitched nonetheless.
I hadn’t yet started wearing waistcoats as much as I do now, and I was not wearing a jacket, but I was wearing a collared shirt and tie – Windsor knot. I don’t know if the Eldredge knot had been invented yet, but I was unaware of its existence, in any rate.
Mary reached up and grabbed my tie in her left hand while keeping her right on my cock, which was quite obviously stiff under the thin fabric of my slacks and the boxers that I was wearing underneath. She pulled on my tie, attempting to bring my face to hers for a kiss, which I was instantly ready to meet when it occurred to me that she had still not uttered a single word since she appeared at my door.
So struck was I by this realization that I straightened up, looking beyond her into the distance to parse the thoughts that were coming into my mind. This had the effect of pulling me up and away from her mouth, which was still closing in on me. She mistook my gesture as playing coy – thought that I was dodging her advance – and she responded by chuckling slightly and dipping to close her teeth on the skin at the base of my neck and then she purred into me, biting lightly and quickly disengaging.
“I’ve had my eye on you for awhile, Rant…” she spoke in low tones, huskiness behind her words.
“I haven’t been here long…”
“It’s been more than a week since I last saw you.”
I was confused, and the look was probably pretty obvious on my face. I hadn’t ever met Mary before… and then it occurred to me – she was one of the women in the restaurant with Simone when I first encountered her. Mary was the one who had her hand on the inside of my thigh when I was telling them about the ranch that I grew up on in an effort to get a better tip.
“I suggested to Simone that she recruit you, you know?”
“Yes – and she was so grateful that she let me break you in.. at a discount.”
“Why did you think she hasn’t fucked you yet?”
“But she has… ”
“HA! I knew it!” she interrupted me with glee in her voice and she literally jumped back to do a little dance.
“I don’t understand…”
“Oh hush, honey… I promise that I will be gentle with you, since this will be your first time…”
“My first time for what?” I am sure that I looked about as confused as I’ve ever been.
“Kneel.” It was a command, not a request, and I responded almost automatically, facing Mary and then dropping to my knees without a word and staring at the floor in front of her feet with my hands behind my back.
“Good boy – well… that was almost good.”
I continued to stare at the floor in front of her feet and she began to walk towards me. In my peripheral vision, I could see her pulling her dress up over her head and I desperately wanted to look up at her and see what she was wearing under that dress – along with what I imagined to be vast stretches of gorgeous, naked skin, but I knew what was expected of me and kept my eyes on the floor.
“Do you not want to see my body, Rant?” her voice was slightly mocking and I forgot my place and looked up to see a very beautiful, and with the exception of her sandals, a very naked Mary, standing with all of her weight on one foot so that she could bend the other one in front of her as she pulled her arms up into her hair, bringing her breasts up as she did so – looking every bit the pinup as she did so.
I think I opened my mouth to start to say something, but the words would not come…
“Oh, but that’s not being a good boy, is it, Rant?”
I didn’t move or make a sound – my brain had hit a sort of vapor-lock.
She walked up towards me, and I kept my eyes locked on her body, but it looked like she was smiling in my peripheral vision as she closed in on me and then grabbed my head behind my head, threading her fingers into my hair and thrusting her pelvis forward, grinding my face into her abdomen, and then she let go with one hand and lifted one of her legs, thrusting her pussy right into my face, putting her knee up on the edge of the island that was still behind me.
A low growl began to form in my throat, unbidden and unfamiliar to me at that time, but I opened my mouth and hungrily accepted her thrusts, meeting with my tongue.
She shifted back a bit to give her more angle and began fucking my face, pressing the back of my head back against the island behind me, so that I could not get away from her.
I was in heaven for those first few moments. She was running her pussy over my whole face, grinding on the bridge of my nose, coming back to my tongue, and I was enjoying every moment of it, but then she started to get rougher, bumping her pelvis into my skull, trying to bounce it off of the island behind me. I was still on my knees with my hands behind me and was pushed back into the island, leaning back from my ankles, which were in front of my center of gravity. I was being held up by the pressure on the back of my head, and she was exploiting that to keep me off balance and toy with me. Then she started to giggle and she brought her leg and arm back down, stood on her toes, and with me still off balance, straddled me with her legs, grabbed the hair at the top of my head in both of her hands and pulled hard, while grinding her pussy into my nose – laughing all the while.
The growl that had been in throat stopped and I started having a hard time catching a breath and was beginning to reach panic when I realized that I was not bound, was nearly twice Mary’s size, and fully clothed still, so I brought my arms up from behind me, dislodging myself from within Mary’s legs, grabbed her by the waist and lifted her off of me as I started to stand.
She tried to move back away from me and fell back onto her ass as I stood, and I thought I saw fear in her eyes for a moment, but then she was in control of herself again, drawing her legs up and pivoting on to her feet.
“Now that’s what I came for, Rant!” She gave me a smoldering look as I was undoing my tie.
She threw out her hand in a ‘stop’ gesture and exclaimed, “No! Leave the tie. Take off the shirt, but leave the tie.”
I looked at her evenly, hearing what she said but having no desire to comply. It was only then that I realized that I was growling again. I slid the tie over my head and while looking Mary directly in the eye, I threw it to the ground behind me and started walking towards her.
I was trying to be menacing, and I think I might have succeeded a little bit, but I ruined it by trying to be like the macho guys you see on TV and rip open my shirt by the buttons, but it proved much more difficult than I expected and I managed to get it free only after a few inglorious tugs and some grunting.
Mary was either being charitable, or my grunting and struggling was intimidating enough that she had the grace to not laugh at me as I was still walking towards her, but she had removed her sandals and was back on her feet. She took a step backwards, and then turned and fled, giggling as she did so.
She ran across the room and up the steps, jumping on my bed and turning to face me on all fours with a wide grin her face, laughing the whole time.
I was not laughing.
I kept walking towards her at the same pace, growling all the while and she once again held up her hand and said more firmly this time, “No. Go get the tie and put it back on. I want something to hold on to.”
I heard the words. I knew I should obey them. I was not in the right mind to do so, so I growled at her instead and threw my arms out to the sides of my body while pushing my chest out.
Much more firmly this time, she spoke again, “No, Rant. Go get the tie and put it on and then take off your pants.”
I came back to myself, remembered my place, stood tall and hung my head towards her, while saying as meekly as I could manage in that moment, “Yes, Mistress.” and then I went over and got the tie, picked it up, looped it back around my neck and cinched it tight, stepped out of my shoes, and then I took off my pants and stood there, bowing towards Mary.
“I meant those pants too, Rant.” Mary said, indicating my boxers.
Understanding what she meant for me to do, I reached down and took off my socks, then took off my boxers and stood again, bowing towards Mary.
“What happened to that hard cock you were sporting through those slacks just moments ago, Rant?” Mary’s voice was dripping with contempt as she indicated my semi-flaccid penis.
My initial reaction was to feel shame, but I’d been taught already to turn that around, embracing the situation as it is and knowing that it will bring pleasure to my Top, so I smiled and meant to say something like, “If it would please Mistress, I will do my best to summon what meager cock I have for her pleasure.” but what actually came out was, “It was momentarily fooled into thinking that some thing worth fucking was nearby…” and my voice was dripping with contempt of my own.
Mary’s smile could have split her face as she rotated her hips to bring her feet around to the side of the bed and stood up, walking over to me to – completely without preamble – slap me across the face harder than I’d been slapped by anyone prior to that point, Simone included. Then she grabbed me by the front of throat and pulled herself into me to kiss me passionately. I was confused and aroused and leaned into it, getting hard as a rock as I did so.
She let go, dropped back onto her feet and favored me with a look that said “I like this” and then she turned to walk back towards the bed and climb back up again, turning over onto her back and then to face me, knees bent, spread-eagle.
“Now, if you don’t get over here and fuck me with that nice, hard cock that I see right there, I’m going to have Simone cut it off and bronze it so that I can use it as a dildo.”
I growled at her, snapped my jaw in the air, and stalked over to the bed, putting my knee directly between her legs and then covering her with my body, putting my hand on her throat and growling in her ear as I did so.
She smiled, grabbed the arm that was attached to the hand that was on her neck, pulled it off of her – and I let her – and then she rotated her head like she was biting into an ear of corn and bit my forearm, hard.
I made an inelegant noise and snatched my arm back from her, pivoting back onto my knees to get away from her teeth, but she followed me, grabbing at me and trying to pull me down, but just lifting herself up instead. I rotated my shoulder around and brought my arm over her, swatting her down to the bed, and then covered her throat again this time, and pushed, pushing her down into the mattress by her throat. Her face went red instantly and I could see that I was hurting her. I didn’t care.
Her eyes got wide and she started to beat at my arm with her own arms – a futile attempt, and I looked at her with derision and laughed. Her eyes somehow got even wider and I let up, letting her gulp a huge breath of air, which she did, and then she launched herself at me, grasping at my head and pulling her face into me to give me frantic, desperate kisses, trying desperately to pull me down into the bed with her, into her.
Knowing what was required of me and coming to my senses again, I relented.
What followed was spectacularly rough sex, frantic moves to change position, followed by grasping and pinning and fucking – glorious fucking! She pushed me, hit me, bit me, grinded on me, thrust onto me, and I pushed back, pinned her, bit her, thrust into her, grinded into her, pulled her hair, and she pulled mine. We went at it like a couple of alley-cats, pulling the fitted sheets off of the mattress along with all of the other bedding, eventually to collapse in a heaving, sweaty pile upon piles of bedding and bare mattress.
Under an hour had passed by this time. I was suddenly not very sure that I could keep this up for four hours.
Fortunately for me, Mary was content to spend large swaths of time in between physical bouts with conversation. She revealed to me much about her relationship with Simone, and the ways that I was being manipulated behind the scenes…
“So, when did Simone fuck you?”
“When did Simone give in and fuck you?”
“Ah, of course… she was supposed to save you for me.”
“What do you mean?”
“We made a bargain – she was not supposed to let you cum until you fucked me. And I didn’t think she would be able to hold out, so we made a wager. If she fucked you first, then I would get this visit for free” and she twirled her hands in the air and lilted her voice as she said ‘free’, “but if I got to have you first, I owe her a bottle of Dom. Far better deal for me, either way…”
“Wait, what?” I can be a really smart guy sometimes.
“So when did it happen? I bet it was last week, wasn’t it?”
“Uhm, no, it was about three hours ago.”
“What?! That bitch!”
“Well, she’s definitely paying for this now… and you want Simone to get her money’s worth, don’t you, Rant?”
We reenacted variations on the theme above three more times over the course of the next four hours, and in between we talked about horses, and wine, and astronomy – she wanted me to show her things through my telescope, but there was too much light for that… I learned more about my Mistress and the people she associated with – trying to remember as much as I could – to be a better slave for my Mistress.
After Mary had left, my phone rang once again.
“Rant. How did it go?”
“I believe that it went well, Mistress.”
“I suspect you would know if it hadn’t… but I will confer with Mary – I’m sure that she will want to discuss things. Is there anything that you need to confess before I hear the story from her?”
“What was that, Rant?”
“Confess, Mistress? I am a bit confused, Mistress.”
“Did you meet with her expectations?”
“I do believe so, Mistress.”
“How many times?”
“Mistress,” I quickly added and hoped that omission would not draw attention.
“Well done. Good boy. Your next client will be there in an hour. Be ready.”
I was dumbfounded. There was no way I would be ready for another client in an hour – I’d need longer than that just to clean the apartment, much less to get to the point of being able to have sex again, but I didn’t have much choice, and I loved that I didn’t have that choice then. Suddenly, it didn’t seem so daunting after all…
“Yes, Mistress. I will be ready.”
I sprang into action and did the best I could to quickly shower, put on nice clothes again (I needed a new shirt, obviously…) and make up the bed as quickly as possible. It was hardly a perfect job, but it was not awful. I began to pace a bit as the implications of my new lifestyle were starting to coalesce in my mind, when the doorbell rang.
That was not the protocol. I don’t think I even realized that I had a doorbell to that point.
I walked to the door and looked through the peephole, to see Mistress Simone on the other side.
I immediately flung the door open and dropped to my knees.
“Rant, move aside so that I can come in.”
I quickly shuffled to the side and she walked past me as I tried to turn on my knees to face her.
“Mistress, I am sorry…”
“Why are you sorry, Rant?”
“I do not know, Mistress. I only was expecting to see .. not you .. and I fear that I have done something to displease you.”
“Mistress! I fear that I have done something to displease you, Mistress. I’m sorry, Mistress.”
“Rant. You did nothing wrong. Stand up and come over here with me…”
She walked into the apartment, over to my bed, and sat on the edge, looking at me as I followed behind her like a scolded puppy.
“Well, how was it?”
Next time I’ll relate a story of Simone’s kindness and compassion. So far you’ve only seen how hard she could be.