Category Archives: sex work

My Personal Journey : Part 7

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.

“Hello?”

“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?”

“Yes, Mistress.”

“Are you kneeling?”

“Yes, Mistress.”

“Are you breathing?”

“Yes, Mistress.”

“Tell me ‘no’ so that I know your brain is still working.”

“No, Mistress.”

“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.”

“Yes, Mistress.”

<click>

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?”

“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?”

“You did?”

“Yes – and she was so grateful that she let me break you in.. at a discount.”

“Wait.. what?”

“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?”

“What?”

“When did Simone give in and fuck you?”

“Give in?”

“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!

“Uh..”

“Well, she’s definitely paying for this now… and you want Simone to get her money’s worth, don’t you, Rant?”

“Yes, Mistress.”

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.

“Hello?”

“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?”

“Confess?”

“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?”

“Four.” 

“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.”

“Good boy.”

<click>

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…”

“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.

Until then – I remain Rant.