What Is It Like Spending An Evening With An Escort? - An Escort's Diary
This post is a revised version of a client's first encounter that we shared back in March 2017 titled "Escort Diaries: Episode One" - originally posted on TheMadisonJames.com blog. I have since refined the post and added a little more detail that I felt was missing. The reason why I've decided to post this here on MJC is because many new escorts may be nervous or a little unsure what to expect so here is an honest account of a typical booking and what things may be like from a client's perspective. I hope you find it helpful - Any questions, you're welcome to leave a comment down below.
Last week Tuesday whilst tucked up in bed fast asleep, I received a very early morning call, which was a little unusual as I tend to put my phone on silent when I sleep. Half dreaming with my head still buried under my duvet, I was nowhere near recovered from the night before. Then I heard a well-spoken (and somewhat nervous) lady ask for ‘Madison James’. Her request slowly filtered through my brain as I started to register that it was, in fact, myself whom she was referring to.
With this new revelation, I attempted to form a semi-coherent response as I realised that this was a new client calling. With a deep clearing of the throat still lined with Gin and Tonic, I responded ‘Hi, Madison speaking, who’s calling please?’ She introduced herself and explained why she was contacting me. For the purpose of client anonymity, I’ll refer to her randomly as ‘Ms x’.
Ms x stated that I’d been recommended to her by a mutual acquaintance (a client) who informed her of my services as a high-class escort. There was nothing unusual about this so I asked her how I could help. She was clearly nervous but after some reassurance, she gathered up the courage to tell me that she wanted to meet for dinner in the evening.
‘Which evening?’ I wondered as I was probably going to be laid up in bed for most of the morning/afternoon. She told me she had already reserved a table at a swanky restaurant in Mayfair and wanted me to accompany her.
Let me weigh this up quickly I thought to myself. My powers of deduction were all but shot to shit at that time of the morning but she had already told me that the table was booked, which I assume was not originally for me. Now, this well-spoken, mature sounding woman was probably married to a busy husband who was unable to attend, and the fact that she was calling me indicated that she was probably being let down in other areas too.
These may be considered somewhat sweeping assumptions on my part but they turned out to be true, well mostly – it wasn’t a husband; it was a long-term partner. What also turned out to be true was the fact that this woman hadn’t had a genuine orgasm in the company of someone else for months. I should point out that this only became apparent later on as it’s not something a lady usually blurts out over the phone when speaking to a complete stranger.
My intentions were to take the evening off and spend time with one of my buddies who was in town for a few days and wanted to hang out. Most of my job focuses on pleasing others, which I thoroughly enjoy but every now and then it’s nice to be able to do nothing at all.
Ms x was fully aware of my services and my particular interests in BDSM/kink but she had something else in mind. She wanted me for 4 hours this evening for dinner and company, and was willing to send her driver to pick me up. Four hours is a long time to sit and eat, even for a foodie like myself so I assumed she’d be wanting more which was fine with me. I meet a lot of wealthy women in my line of work but I’m a sucker for a well-spoken lady with a sexy voice.
We discussed the details of our evening in terms of the dress code. I'm not referring to the venue’s dress code – I'm referring to whether she had any preference regarding my own. My default is a crisp black shirt (sometimes with a waistcoat and tie), well-tailored black trousers, black shoes and a suit jacket. A mature classy woman with money tends to have specific taste so I always like to inquire. I also asked about her favourite food, what type of shoes she tends to wear, her sense of style, the fragrances that she really loves, the music she listens to and anything else that would help me understand the woman I’d be spending the evening with.
We spoke for at least half an hour on the phone and then agreed to meet up later that evening at 7pm sharp. She offered to send her driver for me again but I politely declined, as I always prefer to make my own way. We said our goodbyes and shortly after a text came through with her name and postcode but by then I had already dozed off again. It wasn’t until I awoke a few hours later that I read her message along with a half a dozen or so missed calls from private numbers that I don’t answer anyway.
Right, so I’m up now, still the worse for wear but a good session in the gym usually helps even though I’m struggling to hit my daily calorie intake needed to add on the 5 kg’s that I’m after.
The day flew by, I went to the gym for a good sweat, then I made my way to the dry cleaners to pick up a few suits and then get a massage on the way back home from ‘Magic Fingers’. Magic Fingers is a good friend of mine who taught me how to give a Tantra massage. She’s super hot but as I’d be out with a client later that night, I never have sex before work – but her massage is orgasmic in its own right.
Fast forward to the evening and I arrive at Ms x’s address, which is in a gated community somewhere in central London. I’m always early when meeting a client so I rang the intercom and waited for her to buzz me in. Now usually I’d ask a client whom I’d never met before to send me a picture but as she was referred to me by a ‘mutual acquaintance’ I gave her the benefit of the doubt.
This is one of the reasons why I've worked as an independent escort for so many years instead of joining an agency. I’ve been with escort agencies before in the past and I’ve never really been a fan of their client selection process. I call a spade a spade; I’m a male sex worker who charges £1200-£1800 a night but if I’m not attracted to the woman at all then I wouldn't accept the booking. There are many who may feel very differently which is fine as it's about your own personal preference, but we should also try to be fair to the client.
In reality 75% of the women who I meet 'professionally' I find attractive in some way. They usually have something sexy, quirky or cute about them physically or mentally and I tend to be drawn to that. Now I know many male (and female) escorts who’d take the money regardless, close their eyes and think of Beyoncé but that doesn’t work for me.
I digress; Ms x came on the intercom, (No, I’m not going to touch that line - too cliche) ‘Hi Madison, come in'. I pushed the heavy metal gate which swung open on its hinges and I made my way in past a shiny black Range Rover and a black Aston Martin DB9 to a white house with a large black door. Straight away I knew what perfume she was wearing before she opened the door. It was Shalimar by Guerlain, I knew because I’m a perfume addict with a ridiculous fragrance collection of my own so I pay close attention to things like this.
A fragrance says a lot about a person and I already had a good idea of what she’d be like. I expected her to be very well dressed but casual-chic, stylish and in her mid 40’s with long dark hair, olive skin, looking something like Nigella Lawson.
Turns out I was wrong, she had short hair like Audrey Hepburn, her style was more quirky than chic but by all accounts, she was very pleasing to the eye, more like Melanie Sykes from the Boddington ad. She was about 5,9, I could tell she gymed, had lovely teeth, smooth skin and she’d had her lips done (and maybe a few other bits but I'd need a closer inspection to be sure). She invited me in through a long hallway lined with artwork that lead to her open plan kitchen and her dining room. I smiled as I came in and greeted her with a slow kiss on each cheek.
We hug people every day but Ms x’s hug was different, her back arched more than usual for a first embrace and she nestled the side of her face deep into my chest and held it long enough for me to notice. I wasn’t sure what to make of this, maybe it was my fragrance, I mean I was wearing Chopard, Oud Malaki so I knew I smelt good but still.
She poured me a glass of white wine, we chatted for a bit and then she handed me an envelope, then she had her driver drop us to the restaurant where she had the table reserved. Dinner was absolutely lovely and Ms x and I were getting on like a house on fire as she was very open and very sexy, but also very lonely. It turns out that her partner was a wealthy businessman in the city who was always away. I was the first escort she’d seen so she wasn’t really sure what to expect. What she really wanted was to be noticed, to be felt, and maybe appreciated which seemed to be lacking in her life.
Being a male escort is very different from a female escort, you’re catering to a completely different market with very different demands in most cases. When a man hires a female escort it’s often because he would like sex at the end of the night, I find when a woman hires a male escort it’s usually for the company and attention and if it feels right then she’ll more than likely want to get intimate - but definitely not always.
We sat and spoke for at least an hour and a half whilst eating dinner. We spoke about attraction, desire, lust, life, fantasies, ambition, failures, sexuality, weird habits, weirdos, nice locations to visit with a partner, Pokémon Go and last but not least, when she’d last been touched. I don’t mean masturbation, I mean when she last had someone touch her body in a way that made her feel wanted. It turns out Ms x hadn’t been touched in that way in months, she’d actually forgotten what it felt like. This is something I come across a lot and to be honest, it’s a large part of the reason why I have a job.
By the time the driver dropped us back to her home Ms x was clearly in the mood for something more. Her tone of voice, her body language, the look in her eyes, not to mention the 3 large glasses of wine she’d consumed during dinner all indicated that she wanted me to make her feel special.
Ms x was not silly, she knew women pay me to sleep with them and it’s my job to make them feel desired but I guess the reason why I came recommended is because I genuinely enjoy it and my emotions are real. Obviously, she’s paying me for a service, but the truth is I would usually turn down a booking if there is absolutely no attraction. When I am attracted to a woman, it’s very natural for me to express that emotion, even with someone who I’ve just met.
Ms x told me to come upstairs to her bedroom and make myself comfortable whilst she had a shower. There was steam billowing out of the bathroom and I could smell her vanilla scented shower gel, which smelt gorgeous.
She emerged wrapped in a large white towel. As she came in to view amidst the steam that was quickly evaporating around her, she revealed an amazing body with beautiful curves. Clearly, her personal trainer was worth every penny. I couldn’t wait to feel her and that’s exactly what I did for the next half an hour or so.
I lay Ms x down flat on her back on the super-sized bed in the centre of the room. I gently stroked her body and asked her to focus on her breathing and relax – nothing else. I started with a soft feather light touch, which glided over the beads of water still resting on her back. I unwrapped her towel fully to reveal her shapely size 10/12 body as I leaned in around her neck to inhale the warm vanilla scent that surrounded her. She stopped breathing momentarily in anticipation of my next move.
I continued gliding my hands softy around her body watching to see how she responded. I stroked her from head to toe occasionally squeezing and gently scratching certain parts like her inner thigh and around her midriff but I avoided her erogenous zones for now. Her hips started to roll in response as she let out a muted, almost guilty moan of forbidden pleasure.
I took some scented oil that I had made myself using my fragrance kit and slowly started to drip it on to parts of her body from the base of her neck, along the grooves of her spine, in between her thighs and down to her pedicured feet. She tensed up ever so slightly in response to each drop as the cold oil trickled down following the natural contours of her body.
Essential Fragrance Kit by Vetiver Aromatics
I told her to imagine channelling her energy to the different areas of her body as I touched her. I took my time massaging the pressure points on her feet slowly working my way up her body. By this time I could see that Ms x was completely aroused and finding it difficult to keep still. She was like a beautiful instrument that had been left on the shelf gathering dust just waiting to be played. Her face flushed red from the endorphins pumping through her body and she had tears in her eyes as she held my hand tightly against her stomach.
The human significance of the skin’ by Ashley Montagu
I asked her what was wrong and if she wanted me to stop but I already knew the answer to both questions. Ms x was experiencing what a lot of women in her position feel when someone like myself takes the time to appreciate them after such a long period of neglect. Nurturing this emotion in a woman like Ms x gives her the confidence to embrace her femininity and express it freely.
She smiled and apologised feeling a little embarrassed but there was no need to feel this way I told her. It’s good for us to tune in to these feelings so I encouraged her to let go and not worry about anything. Crying is so inherently linked to pain and misery that we automatically try to stem the flow and in doing so we sometimes miss the nuances that can also take place. Ms x was experiencing an overwhelming sense of feeling desired which brought in to contrast what she had been missing in her life for so long.
After giving Ms x a warm hug I continued but this time I directed my movement towards her erogenous zones, gently running my hands past her breast, down her stomach and on to the lips of her vagina which was already dripping wet. There’s something extremely erotic and primal about a woman in this state, full of feminine energy coursing through her veins just waiting to erupt. She took hold of my wrist and tried to guide my fingers inside but I stopped her and made my way up her body following every curve with my warm breath until I reached the side of her neck. “Not yet” I whispered softly in her ear to which she responded with a deep sigh in an attempt to relieve the sexual tension.
Now that I knew she felt safe and relaxed I decided to take her a little further down the rabbit hole. Again I told her to focus on her breathing but this time she was to close her eyes and follow my soft kisses moving around her entire body. As I inhaled and exhaled deeply I could see her body responding to me like ocean waves coming back and forth with increased intensity. Her involuntary reactions as she felt me move past her midriff, along her pelvis and then down towards her inner thighs told me she was fully tuned in. I played with this sensation going back and forth and with one hand wrapped firmly around her neck she suddenly felt my wet tongue massaging her swollen clit. She moaned and ran her hands over my head and down my neck with an intense exhalation of sexual tension that had probably been building up for a very very long time.
I licked and teased and frustrated the hell out if her until she was so close to orgasm that she had lost almost all composure. She was wild and untamed and ready to release but again I decided to take her a little further. I moved away from her vagina and began massaging her midsection and working my way around her body until she was able to control herself again. I really enjoyed watching her in this state, she was so in tune with her feminine energy and now felt comfortable enough to share that with me openly. When you consider that we had only known each other for three or four hours and we were able to connect on that kind of level tells me that we have an innate primal response when pure masculine and feminine energy combine.
With my tongue wrapping around her clit and my finger inserted in her vagina angled upwards towards her g-spot I could feel her entire body tense up as she arched her back. She let out an uncontrolled gasp full of sexual repression that had found a way to the surface. This was a beautiful orgasm to witness and I genuinely enjoyed sharing that experience with her. By now Ms x wanted to f**k, her eyes were glazed over and I could see she wanted me deep inside her. As I finally entered her world she wrapped her legs around my waist and pulled me in even deeper - she felt lovely.
As I stroked her insides I told her to contract her pc muscles (pubococcygeus) so she could intensify the experience and control me inside her more freely. I took my time feeling every intricate part of her pussy to discover what she liked and how she liked it. When I found a sweet spot I teased her with it by making her wait in anticipation of my next thrust. I was moving forward, pulling back, circling it, stopping halfway, going deep, then shallow, exploring every angle, pausing to look at her in admiration, then sinking deep back into her vagina unexpectedly. She threw her head back in delight as she realised what I had been doing to her all along.
Ms x came again but this time she slapped me in the face so hard that I growled and bit her neck in response as I also released. This was a clear signal that she may enjoy exploring my world of kink at a later stage. What Ms x realised is that from the moment we had met I was focused on tuning in to her and understanding what pushed her buttons and how best to fulfil her desires. This is not just a case of me giving her what she wants, exactly when she wants it. It’s a case of me giving her what she wants when all her senses are tingling and crying out for release because this is when it’s the most enjoyable. When I was inside her she could feel me doing exactly that and she loved it.
After we had freshened up we lay in bed with her head on my chest as she stroked my stomach. It was soon time for me to leave but Ms x had other plans. “Will you stay Madison?”, she asked as she got up to get her purse from her bag and hand me enough money to cover my time until the morning. Most women in this situation do feel a sense of reality kick in because as much as I'm affectionate and caring, I’m still paid to be there. Having said that, no amount of money could have taken her to the places she visited during her time with me. I could have just given Ms x good sex and she’d have been satisfied because she wouldn't know any different but the reason why I do what I do, is the reason why I became an escort in the first place.
I enjoy nurturing a woman’s sexual desires and allowing them to open up and embrace - this is what turns me on (and of course the money is good too!) I’m not suited to all women and that’s ok because I know and understand the type of clients who I want to inhabit my world. Ms x and I spent the remainder of the night sleeping comfortably next to each other in her oversized bed, which probably felt a lot cosier to her than it had done in a long time.
We awoke early the next morning with a beaming sun peeking through her blinds which was strange for the month of March but who am I to argue. She handed me a coffee and called me a cab. We sat around the kitchen table waiting as I listened to her explain to me how much she enjoyed last night. I’ve been here many times before with many women but everyone is different. We all have our own story to tell, our own desires, our own demons and our own way of expressing ourselves.
My cab soon arrived and Ms x walked me to the door and gave me another warm full-bodied hug but this time she cupped my head firmly in her hands and gave me a sensual kiss on the lips. “Thank you, Madison” was all she said with a look of realisation in her eyes. I gave her a smile, pulled the door behind me and hopped in my cab. As my driver weaved his way through traffic I zoned out and relaxed amidst the hustle and bustle of central London on a Wednesday morning.
We'll talk again soon.
Privacy Note: Names and locations have been amended to protect client confidentiality. Posted with client consent.
▪️ Do you disagree with any of the points I’ve made above?
▪️ What other topics would you like to see covered in this blog?
▪️ Feel free to leave a comment below as I’d really like to hear your thoughts.
▪️ If you like this post, don't forget to subscribe to receive more in your inbox.