Escort Diaries: Her First BDSM Session

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Ms. D initially contacted me because of her curiosity about the world of kink and BDSM. Like many women the world over, her understanding of BDSM was largely shaped by the hugely popular and now infamous ‘Fifty Shades of Grey’.

Ms. D had hired me on two previous occasions but was now looking to take things further. With trust being a key element in BDSM, I’m always reluctant to engage in anything too intense with a client until we have spent some time getting to know each other.

Ms. D is a professional woman in her late 40’s with no children. She comes from a tough corporate background surrounded by men in grey suits. She deals with the usual testosterone fuelled egocentric characters that often exist in this environment. Ms. D had a tough exterior that soon melted away once our mental chess began and she realised I was wired a little differently to most.

Ms. D was accustomed to getting what she wanted, especially from people who were paid to be ‘nice’ to her. ‘Nice’ is when someone invites you out for a drink, or offers you their seat on a train, or pays you a kind compliment – she can get ‘nice’ for free. But that’s not why she pays me; she pays me to make her feel amazingly special, which requires a lot more than kind gestures and compliments. It’s about leaning how to push her buttons in a way that excites her and allows her to let go whilst she’s with me.

Putting a BDSM script together for a client is always a turn. No two people are the same so everything has to be tailored to that specific client and focused on what they want to gain from our time together. During our last encounter as we lay in bed, we spoke in detail about what she liked and how she wanted to feel. We spoke about the toys that really turned her on and how she wanted to be handled. We also spoke about her boundaries, safe words and any concerns that she may have had. All the while I’m building up a mental picture of how our session would play out.

Sitting at my desk in the early hours of the morning I was able to create an experience for Ms. D that I knew she would love. BDSM aside and the fact that I’m a paid escort, I think this is something that we should all do at some stage. It’s a beautiful thing to be able to create an experience of pure pleasure for someone based on what you know will drive them crazy. With the script pretty much complete I could hear the birds chirping so I decided to shoot off to my 24 hour gym for a sneaky workout while I was still wide awake.

Fast-forward to the day when Ms. D and I were due to meet up, everything was prepared. A fresh black suit, immaculate black shirt with starched creases in all the right places and a lovely pair of black John Lobb Oxford shoes. I also packed my bag of toys complete with oils, cuffs, dildos, a handmade leather flogger and some other goodies. Lastly I selected just the right fragrance for the occasion ‘Black Orchid by Tom Ford’ as it oozed dark mischievous sexuality.

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All set, I hopped in my car and made my way to Ms. D’s home which was located in a lovely remote part of Cheshire. When I arrived the large antique wooden door was already unlocked and she had told me to come in and make myself comfortable.

As I gently pushed the door open I could hear her voice travelling from one room to the next which meant that she was on the phone probably dealing with some work related issue. As I sat down and waited for her in the reception I saw an envelope with my name on it on the side table. I flicked it open, fingered the cash and slipped it in my pocket.

She was soon off the phone with her arms wrapped around me and playfully smothering me with warm kisses. It’s very sexy how she could switch between work mode and personal time so effortlessly. She was clearly looking forward to our play session. After her delightful barrage of kisses I pulled back slightly, looking her directly in the eyes and told her to behave herself, which only provoked her more. Ms. D was use to getting what she wanted but she knew that I loved to tease so she turned on her heels in quiet protest and invited me to join her in the kitchen.

Ms. D was tall, about 5’9 and I’m guessing a size 12 although I never asked. She had very good posture, with long shiny brown hair that was always tied back in a high ponytail. She had light brown eyes, sharp features and pale skin.

As this was her first BDSM experience there were still some rules that needed to be clarified. There was ‘no alcohol’ permitted before or during our session as we both needed to be fully aware. We also covered a few important topics again like her boundaries, safe words and any general concerns.

Putting all the excitement aside, making Ms. D feel safe and comfortable was my main priority because without her mind being in the right place, it wouldn’t matter what I had planned as she wouldn’t be able to enjoy. Sex is mental so that’s where I started and with that, Ms. D and I were ready to begin our first session together.

Ms. D’s room was perfectly suited; I don’t mean it looked like a dungeon with red and black leather lining the walls. I mean it was spacious but imitate with lovely dark fur rugs, thick blankets, oversized cushions and a large bed in the center of the room. There was original artwork on the walls and long hanging curtains that threw the room in to pitch darkness. Ms. D turned on a large lamp in the corner that created a warm glow and then hopped in the shower whilst I prepared her evening’s events. When she was finished in the shower she agreed to come out and present herself to me awaiting further instructions.

I laid out my toys, handcuffs, restraints, bondage ropes, a blindfold, my flogger, a paddle and some strawberry scented oil. As this was our first session together I wanted to ease Ms. D in at her own pace so she always felt a degree of control. She came out of the shower in an oversized bathrobe, seeming nervous and somewhat out of her comfort zone. I’d never seen Ms. D like this before. I walked over and slid my arms around her waist inside her robe and pulled her close. I asked if she still wanted to go ahead to which she responded with a cheeky smile and a nod, I removed her robe and we began.

I presented Ms. D with a thick leather collar that I placed in her hand as she stood in front of me naked. In BDSM the collar is much more than a kinky accessory, it signifies submission on her part, and me taking responsibility for her whilst she allows me to Dominate. This collar represented a mutual agreement between the two of us based upon a set of defined rules as laid out below:


During session you are to address me as ‘Sir’.

You will do as you are told as all times.

If at any stage you disobey me you will be punished.

If you orgasm without my permission you will be punished.

If you need to use the ladies you will ask for permission.

If you need time out, or some water or anything else, you will ask me.

Your safe words are ‘YELLOW’ if you want me to slow down and ‘RED’ if you want to stop. You can use them anytime you feel the need and I will stop immediately

I will only push you as far as you’ll allow me based on what we have discussed previously.


Once I put this collar on you, your body and mind will belong to me for the duration of our session. Do you understand? I asked her. ‘Yes’ she replied.

I stepped in to her space with my arms folded behind my back and in a firm voice I repeated the question, only this time she replied with ‘Yes SIR’. ‘Good girl’ I told her and with that I placed my hands on her hips and turned her around slowly to fasten the collar around her neck. The last thing I did before we began was whisper in her ear that I was there to please her. Ms. D stood there in submission with her naked figure fully exposed with the innocence of a woman far removed from her everyday life. And with that I grabbed her around the throat and pushed her up against the wall. She inhaled deeply in shock as I stepped back admiring her body. I picked up my flogger and swung it over my shoulder as I moved towards her with my hand running down her side. I moved up and down her body inhaling and exhaling as goose bumps started to appear on her skin. I ask her how she was feeling to which she responded ‘I’m fine Sir’. I stroked her face and told her to turn around and face the wall.

Ms. D had always wanted to be tied up and dominated; this was one of her fantasies. I took my bondage rope and tied her hands firmly behind her back. I grabbed her long hair and gave it a good tug, she moaned as her head snapped back. I bit the side of her neck and pulled her over to the beautiful leather upholstered bench at the foot of her bed. I forced her on to her knees and pushed her face in to the leather. I could feel her trying to resist in an act of defiance which given her character was no surprise. I explained to Ms. D in no uncertain terms that her behavior was unacceptable and with that I pulled my flogger from over my shoulder and started spanking her bottom. Ms. D gritted her teeth and invited me to flog her harder. She was definitely no shrinking violet. I knew she wouldn’t just roll over and comply. In order for me to be allowed do dominate her, I would need to prove that I was deserving of her submission – women submit to men, not boys.

Ms. D raised her head and stared at me with squinted eyes and perched lips, which was her way of testing me. I placed my hand on her head open palm and pushed it back down and flogged her harder. We repeated this process enough times for Ms. D’s arse to turn red and she was now winching from the sting of the flogger. I stopped and asked her if she wanted to continue resisting to which she replied “No Sir”. This signaled that she was now ready and willing to submit as I had proven to her that I would administer punishment consistently if required.

With the script memorised in my head and broken down in to three main scenes I proceeded to take her on a journey with me. I cuffed Ms. D’s ankle to each corner of the large leather bench, which spread her legs apart exposing her vagina. I stood up pacing the room slowly behind her with my flogger gently stroking the skin occasionally whipping it against hand so she could hear the sting. The flogger is more than just an instrument of pain and discipline. It can also be used for gentle and sensual pleasure. Ms. D indicated her preference at any one time by her compliance or lack there of. This particular flogger is unique because it was handmade by myself using the best soft Italian leather and was balanced perfectly to administer pleasure or pain depending on the situation.

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I started to massage her back with deep sensual strokes helping to circulate the blood around her body. I explored her with my hands paying close attention to her every response. I slid my finger down the crease of her backside and over her wet vagina to which she responded with an inhalation of pleasure. She sounded beautiful, but tasted better as I licked her juices off my finger and then inserted it in to her mouth, which she licked fiendishly. I stopped for a moment to appreciate her in this state. My job as an escort was to make her feel special and she was obviously enjoying it but I always found it flattering that a woman would literally gift her body and mind over to me to play with like a beautiful instrument. With that in mind I suddenly bent down behind Ms. D and pushed my tongue deep in to her vagina, rubbing past her clit. She moaned and rolled her head back as I pulled out. ‘There’s a good girl’ I whispered as I gently ran my fingers through her hair. I intended to push every one of her buttons and leave her senses tingling.

I teased Ms. D with my tongue for long enough to bring her to a state of hot steaming orgasm. Just as she was about to release I stopped, grab her face and reminded her that she was not allowed cum until I permitted it. This drove Ms. D crazy to the point of frustration. She let out a stream of expletives expressing exactly how she felt towards me at that time. Given her strong character I knew that most of her partners in the past would have given in at this stage but it didn’t work like that with me as we were in session and these were the rules.

For her sins I pulled out my flogger and began to spank her as I politely requested an apology for her rudeness. Ms. D was reluctant but the sting of the flogger soon loosened her tongue.

It was now time for a new act and with that I released her arms and legs, attached a lead to her collar and slowly walked her over to the bed. I grabbed her hair and threw her down as the bed recoiled from the force. With Ms. D on her back I secured her arms and legs to the bedposts with her vagina in full view, waiting for my attention. Before I went any further I leaned in between her legs and gave her a soft sensual kiss. I felt to enter her right there and then but resisted as I had other plans.

I pulled out a magic wand vibrator, which is probably one of the best devices I’ve ever come across. With Ms. D tied up and lying on her back I rubbed the large vibrating head slowly up and down her thighs and across her vagina. Ms. D tensed up and rolled her hips in response. She was breathing short and fast so I instructed her to slow down and inhale deeply whilst focusing on my touch. I alternated between the sensation of the vibrator and the feeling of my tongue as I gently licked her outer labia. This drove her crazy as she wriggled and fought against the straps that were restraining her. After some time of dialing up the tension I placed the head of the vibrator directly on her clit and watched her body contort as if possessed. With deep inhalations and moans of ecstasy I knew it wouldn’t be long before she was close to orgasm again.

This for me is the moment where communication and connection is so important. I removed the vibrator momentarily to get her to focus on my voice. I instructed her to let me know on a scale of 1 to 5 how close she was to orgasm. Still not fully coherent she agreed by nodding her head frantically. Her pussy was swollen and red from the pressure of the vibrator so I slowly licked her clit and massaged the sides of her vagina to prepare her for what was yet to come.

As she was now focused again I began building her orgasm slowly by bringing her back and forth, trying to keep her in a state of intense arousal. There came a point when Ms. D was clearly overwhelmed by what was going on. She begged me to let her cum – I told her ‘don’t you fucking dare’. I kept on pushing her and eventually she gave in to the sensation and released her orgasm. It sounded was like music to my ears – she let out a deep sensual moan of pleasure as she kicked and fought against the restraint straps still holding her firmly in place. The bed was shaking, she was covered in sweat and I could sense the energy coursing through her body as she reveled in the moment.

By this time Ms. D was due a well-deserved break so I untied her, placed a cover over her legs to keep her warm and poured her a glass of water. Ms. D was silent and she wasn’t moving much at all. I knew exactly what was going on, she was tuning in to her body and enjoying a different kind of sensations that she wasn’t used to. We lay in bed next to each other while I stroked her hair. I nestled my head in her neck and nibbled her ear repeatedly teasing her back to reality. She giggled and curled up to get away as I ticked her. As she sat up and sipped her water she turned to me and said, “You’re very bad you are – very,” like a well spoken head mistress telling off a naughty schoolboy. I winked and smiled at her with a troublesome smirk as I thought about the events I still had in store for her.

Now for scene two I had included a little role-play. I told her to stand in the middle of the room naked and wait for further instructions. I made her put on a pair of black high heel stilettos and wait for me while I took my time admiring her as she fidgeted in anticipation. Ms. D, already being 5’9 struck an awesome figure in heels and we were now eye to eye. “Get on your knees now” I commanded and she obeyed without hesitation. I stroked the side of her face, grabbed her by the throat and bent down to kiss her. I told her to take out my penis and lick the head. She done as she was told and looked up at me for approval as she licked and slurped with her hands firmly gripping the shaft.

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(Not actual image)

I was so turned on I could have let her take me all the way but I had other plans. Snapping back in to character, I slapped her in the face and told her to slow down. I pulled out and teased her with the tip by placing it on her tongue and rubbing it over her lips. She leaned forward trying to get her mouth around it but I pulled away again. “No Ms. D, you’re a very naughty women aren’t you, I’m going to punish you”, she replied with “Yes Sir, I’m sorry”. I picked her up with force, bent her over and placed her hands on the bench with her legs spread far apart. I picked up a paddle and began to spank her bottom. She moaned and gyrated from the repeated blows of the paddle. ‘Harder” she said so I stepped it up a little more. Her arse was turning red and she started to winch but she was enjoying the stinging sensation. I teased by reminding her about the safe words and asked if she wanted to use them. “Fuck you Sir’ she said as she giggled and turned away knowing that swift punishment would be meted out.

I smiled and I told her to keep facing the front while I rummaged through my bag of toys and produced a black 9-inch rubber dildo complete with bulging veins and a circumcised head. With Ms. D still lent over, I knelt down, licked her juices and inserted 3 fingers in to her vagina. She inhaled as she leaned back causing all 4 of my fingers to slide in. I finger fucked her briefly to moisten her up and without warning I inserted the black 9-inch dildo half way in to her pussy. She yelped and took a deep breath as she tried to compose herself. I guided the dildo in and out going slightly deeper with each thrust. Ms. D let out an exasperated quiver as she slapped her hand on the leather bench in an attempt to control the overwhelming sensation. “Fuck who” I asked her. “You Sir, fuck you” she replied with another moan. I like her spirit;) so naturally I inserted the dildo even further until she had taken the whole 9-inches. By now she was making enough noise to wake anyone within a 5-mile radius, but the sexual deviant in me encouraged her to let go and so she did.

I grabbed my flogger and started spanking her arse with the dildo still buried deep inside her. I asked her to repeat what she’d told me previously, “Fuck you Sir” she blurted out again. Clearly she wanted more so I gave it to her. After full lashes from the flogger she soon screamed ‘Yellow Sir, yellow’. This time I threw the flogger on the bed and grabbed the magic wand again. With the 9-inch dildo thrusting back and forth I placed the magic wand directly on her clit. What a fucking response – she was totally in the moment with her legs shaking and her head snapping back and forth like Beyoncé on stage.

I massaged her clit with the wand and before I could even gauge how close she was to orgasm she began to cum. I wanted to prolong the experience as much as possible so I adjusted the intensity and got her to focus on channeling the sensation to different parts of her body. This very loud and uncontrolled orgasm lasted well over a minute and by the time she had climaxed the carpet was wet and sweat was running down her thighs. With her body shaking, she gently collapsed to her knees with her arms spread wide, face down on the bench. She was thrilled and exhausted in equal measure and very much in need of another break.

Ms. D had a number of emotions flowing through her body at that stage. She was realising that there was so much more to her sexuality than she had previously experienced. Putting BDSM aside, what we we’re doing was exploring her sexuality and allowing her to express it in what ever way she felt comfortable. Throwing BDSM in to the mix allowed her to play out her fantasies with a shift of power and control like ‘orgasm denial’ and ‘reward and punishment’. Ms. D quickly learnt how to manipulate the situation in order to get what she wanted from me.

I helped her to her feet; she was so exhausted all she could do was wrap her arms around my waist as I carried her over to the bed. I lay her down on her stomach and poured some of the scented oil in to my hands. I then straddled her body and started massaging her back from the neck down. She seemed to melt as she exhaled the sexual tension that had been building up inside her. I wanted her to relax and let her mind drift.

After some time she floated back to me and we spoke for a while about how she was feeling and the sensations running through her mind. I didn’t say much as I was trying to take it all in. This level of openness is rare because it’s not often nurtured so I always enjoy moments like this.

Now it was time for the final part of our play session and I wanted take Ms. D to a more sensual place. As I lay between her legs with my head rested on her thigh I gently teased her clit by swirling my tongue around as she began to moisten up. I grabbed her hand and placed it on the back of my head gesturing for her to guide my tongue where she wanted it.

Soon Ms. D wanted to fuck, she wanted me deep inside her and she wanted it now. She grabbed my head, clamped her legs around me and maneuvered in to position. As I sunk in to her warm, pulsating pussy I watched for her every response as I tuned in. I slowly explored her world feeling for her most sensitive areas and teasing them with a variation of strokes. After some time I broke free of her legs still wrapped around me and rested them on either side of my shoulders. Now I was really in a position for deep penetration as I massage the walls of her vagina. With my hands holding her firmly around the waist and my knees tucked slightly under her backside, I angled for her g-spot and sunk deep enough to feel her cervix. She yelped and pulled me in deeper, she wanted more so I gave it to her again – and again and again.

I continued exploring her with deep controlled thrusts and then shallow, slow circular motions and then long pauses when I hit a sweet spot, teasing her until she started to thrust back at me. I peeled her legs back and fucked her deep and hard as she screamed. I could feel her pussy tense up so I asked how close she was, “3” she replied as she grabbed the pillow to muffle her screams. By the time she reached 4 my own orgasm was imminent. Flooded with Oxytocin and all the other chemicals running through our brains we fucked like bunnies with Ms. D giving as good as she got through gritted teeth and expletives.

As soon as I heard her cum I let go and released what was now a seriously fucking intense orgasm. I snarled like an animal with my hand wrapped around her neck. After the climax we just stared at each other, sweating and panting; no words needed.

I lay her legs down slowly and gently massaged her hips and thighs, running my hands down her legs to channel the energy to the tips of her feet. For a moment she lay completely still with her eyes closed. After a short while she looked at me, giggled and pulled me up along side her. She exhaled a long “Arhhhhhhhhhhh” like she was releasing years of frustration and at the same time playfully cursing me for being such a tease. After having shared such an intense experience together it was nice to be able to drift off and talk freely about sexuality, life and anything else we fancied.

That night I left Ms. D sleeping comfortably curled up in bed under her warm duvet. I gave her a kiss on the cheek and closed her bedroom door quietly behind me. I arrived home just after 3 in the morning; way too tired to hop in the shower I collapsed on my bed and slept until 11:30am. When I awoke a quick glance at my phone displayed a message from Ms. D that read, “Thank you Sir, I look forward to being punished again. Ps. Fuck you.” (Wink emoji and a bunch of kisses.)

I smiled as I imagined her back in the office among the grey suits, occasionally floating between work mode and the warm memories that lingered in her thoughts from the night before.


Privacy Note: Names and locations have been changed to protect client confidentiality.
Safe Sex Note: I always practice safe sex and never participate in penetrative intercourse without protection. I also receive regular check ups as do all responsible sex workers.
-Always practice safe sex.
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