520 - A Surprise Customer

I take a lot of what customers say to me with a pinch of salt as I learned that only about 25% of them actually keep to their word which to me is an acceptable amount and I have built up a somewhat regular bunch of clients albeit with varying timeframes but it’s all cash coming in which is the object of the exercise, they weren’t all massage clients and they weren’t all sexual experiences either which actually made for a welcome change to go cut someone’s grass or clean their houses, even the odd DIY job was satisfying..

It was late on the next day when I had a call from Izzy which was a pleasant surprise and she apologised for not getting back sooner, she’d spoken to her daughter Suzy and she was considering my offer but just needed a break in her schedule which I said was perfectly fine but then she told me about her friend Jessie who she’d had lunch with that day and I became the topic of conversation..
It turned out that Jessie was an Anne Summers rep and did parties promoting their products and that her clientele were a mixture of young married ladies trying to spice up their sex lives, divorced ladies and even the older generation who weren’t getting the love and attention they once craved, there’s always a reason for ladies attending these parties..
Jessie herself was divorced and 40 and had lived life the best she could bringing up her two sons alone and was apparently very interested in my services and would even pass out my number to her own clientele if my service lived up to the hype that Izzy had given, obviously she didn’t tell all the details but told me that she thought Jessie had got the idea and would I be free in the morning for her to visit, of course I said that I was free and would welcome her with open arms..

I thought this was a splendid idea and word of mouth advertising is the best you can get and I thanked her for the call and went to bed excited knowing that I’d have to give a good account of myself in the morning..
I woke up early and had breakfast with the family before they all went their separate ways and it’s always nice to have an empty house when clients come although that doesn’t always happen and after eating I went up to set up the room and have a quick shower ready for Jessie’s arrival, I put on a pair of small white running shorts that didn’t leave too much to the imagination deciding that a top wasn’t necessary today which I’m sure will set the mood nicely, I had already decided that I wasn’t going to give her the option to keep her knickers on but if she does then she does..
I put some fresh coffee on thinking that a coffee is always a nice ice breaker before we get down to business and it wasn’t long before Jessie pull up outside, I stood by the window excited to see if she looked anything like I had imagined..

As she got out the car I could only see the strawberry blonde locks on top of her head and it looked like she was adjusting her dress or something before she came into full view and then oh my god, she was wearing a strapless tube type dress that was clinging to her figure like a second skin and only just covered her body, not something I was expecting a 40yo woman to wear I have to admit, perfect for going clubbing but who am I to complain, it’ll be coming off pretty soon anyway but will certainly get the blood flowing while we have coffee and at least she was wearing sensible shoes..
I wouldn’t say she was a stunner looks wise which is probably why she dresses that way but there was certainly sex appeal as she approached the door quickly ringing the bell before I could get there..
As I opened the door our eyes met briefly before we both scanned each other’s framework..
Jessie: “Hello Frankie, Izzy was so right, you are a little cutie aren’t you” she said excitedly and straight away I could see her personality shining through..
Me: “Good morning Jess, I just made some coffee before we start, you fancy some” I stuttered my reply feeling myself slightly blushing by her openness but it sure did break the ice..
Jessie: “Sounds like a plan darling, I’m in no rush, I do like it hot” she said as I showed her into the kitchen noticing not only did her legs go up to her armpits but I could just make out the string of her tiny undies as I focused my eyes on her bulbous arse cheeks, her dress was so short and clingy that I could almost see her gusset and as I motioned her to take a seat she quickly eased the hemline down being careful not to pull to hard or there was a likelihood of her tits popping out and it was plain to see that she had no bra on..

I poured the coffee and handed one to her and it was like impossible for her to sit without showing her knickers, even with her knees tight together I had a clear view and it was like a magnet to my eyes and she could see me looking too, I wanted to find out exactly what Izzy had told her about my services or at least as much as she wanted to tell..
Me: “So you had a good lunch yesterday then Jess, I hope Izzy is well after her treatment” I said fishing for answers..
Jessie: “Oh yes, and I think she was still glowing so you must’ve done her well, I’ve never seen her so happy.. I hear you going to give Suzy one too, that’s so sweet” she said cheerfully with her wording sending mixed messages but it was nice feedback..
Me: “Yes, I hope so.. so have you had a massage before” I asked getting that question out of the way, she smiled as she tipped her coffee and I could see where her eyes were focused..
Jessie: “Not professionally no, I had an ex boyfriend who tried it but it was just a way for him to get his hands on my body, no rhyme nor reason and his technique sucked, that’s way he’s an ex” she said with a chuckle as the conversation flowed and I could feel rapport building..

We spoke about her job which I could see she was enthusiastic about saying she had so much fun showing off her wares and how much fun her clientele was, each party she did led to more bookings and she said she’d be able to get some referrals for me, ‘If I was good’ which obviously I had to prove, I could feel a lot of sexual tension in the room and it was now up to me to take that upstairs for justification..
Me: “Ok then Jess, let’s go up and put a smile on your face” I said as we finished our coffee and being the gentleman I am I motioned her to lead the way.. she didn’t complain either..
In a dress as short as that there was no way she was going to climb the stairs without exposing herself and I know that in about ten minutes or so she’ll be naked and I’ll see it all anyway but there’s just something so exciting about the sight up the back of a dress, the gusset of her panties was so thin and tight I could see her beef curtains hanging either side and the sight of her shaded crack had my blood flowing and how the hell I got up the stairs without achieving a boner remains a mystery but my bulge had definitely started to grow, we got into the treatment room and her eyes lit up seeing the relaxed and cozy atmosphere..

Me: “Here we go Jess, if you would be so kind as to get yourself ready and lay on your front with your head in the headrest and the centre cushion under your belly for me, there’s a modesty towel there if you need it, I’ll give you a few minutes privacy” I instructed as she looked around the room totally amazed at the professionalism on show, I left the room leaving the door slightly ajar preparing myself for what I hoped would be a wonderful experience for both of us..
I went back in and was pleasantly surprised that she was totally naked on the table without using the curtesy towel and her legs were already slightly spread, I looked down at her raised arse which was going to be a pleasure to work on..
Me: “That’s good Jess, are you comfortable and are there any issues or areas that need special attention” I asked as I walked around the table looking down at her framework which for a 40yo woman wasn’t bad.. she raised her head as I oiled up my hands standing in front of her, I could see exactly where she was looking too..
Jessie: “Yes I’m very comfortable Frankie and yes I do have a few issues, my lower back gives me grief sometimes and also my bottom, that’s coz I sit on it all day hehe.. can I ask you a question” she said which was all good information but was keen to answer whatever was on her mind..
Me: “Sure, ask anything you want my lovely” I replied as I stood a couple of inches away from her face and started to work on her shoulders.. she cleared her throat..
Jessie: “Sorry for asking but don’t you find it weird massaging a woman old enough to be your mother” she asked rather hesitantly but certainly with excitement in her voice..

Me: “Actually Jess I get asked that quite a lot and to be honest I do massage my mother and father too so it’s no big deal, look at it like I’m a mechanic working on cars, some of the older cars need a bit more love and attention which is my job to provide” I said which I thought was a damn good explanation and I could feel that she did have lovely skin as I worked those shoulder blades, her arms were dangling down the front of the table and I could feel myself starting to respond..
Jessie: “That’s a great way of putting it Frankie, a bit kinky but good, my son is about your age too, maybe I should get him to do me too.. (she giggled).. oh and you have great hands and such a lovely touch” she said as she rested her head back into the head rest but I knew that my impending boner was still visible to her as I had the headrest adjusted just right..
I could feel her arms swinging with the motion of the table and as I found a hard spot I felt her grab the back of my leg which she was very apologetic about..
Me: “Oh don’t worry about that, I see I’ve found a tender spot there Jess, we’ll soon have you fixed” I said softly as I worked on the area however as I didn’t complain about her contact she kept her hand on the back of my thigh but I could feel myself growing in my shorts..

I finished the troublesome area and then slowly started to work down her spine towards her lower back knowing she had issues there but it did mean stepping closer to her and she felt my bulging shorts making contact with her forehead..
Me: “I’m really sorry about that Jess, I wasn’t blessed with long enough arms” I said making a joke out of it but for all intents and purposes I don’t think she minded..
Jessie: “Oh that’s alright darling, it seems you were blessed in other areas though and I ain’t complaining” she said as she lifted her head up slightly and I could feel her face pressing against me..
Jessie: “Shame you’re wearing those shorts darling otherwise who knows what might happen.. Oooh that’s alright does feel nice, that’s the spot right there” she gasped as I found the troublesome spot on her lower back and because she felt the discomfort her jaw dropped and I could feel something getting very close, she now had both hands on the back of my thighs and I could feel them moving slowly upwards as I worked her problem area and what’s more I could feel her mouth now pressing against the boner that had appeared very quickly, she was even nibbling at the waistband of my shorts testing the water to see how I would react, I suppose it didn’t help that I instinctively pressed harder against her..

My dick was now angled slightly and pressing against the waistband of my little shorts and as she grabbed the back hemline of my shorts I could sense her applying a bit of pressure and I knew it wouldn’t be long before something popped out the top, I was right in my assumption..
Jessie: “Oops.. looks like the mouse has left the house, so sorry darling.. but WOW!!” she gasped as my shorts started to slip..
Me: “It’s ok Jess, I didn’t think they would stay on long” I said jokingly as gravity took control with a little bit of help and left me naked in front of her face as I continued to work on her lower back..
Jessie: “Now this is what I consider kinky darling, not seen a teenage cock in a while, so big and hard.. mind if I give it a little suck” she said excitedly as her hands moved up to my arse cheeks squeezing them gently as her tongue flicked across my dick vying for position and very quickly she had her lips around my bellend and her head started to move up and down dribbling her saliva down my shaft, she knew exactly what she was doing but at least it took her mind off of the discomfort in her lower back..

I did as much work as I could on her lower back but knew I could do more from the other end if I lowered the table which was an option for me but her oral skills were so good it wasn’t long before I was shooting my load down her throat swallowing every morsel I could throw at her and knowing that the next area of concern was her arse I had plenty of time to recover..
Jessie: “Wow darling, that was awesome, is that all part of the service.. I have a feeling this is going to be a good experience” she mumbled as my semi had dick slipped out of her mouth, I had to chuckle to myself as I knew there was more to cum, pardon the pun it was intended..
Me: “I like my treatments to be of mutual benefit Jess, it can be hard to work on such a beautiful lady like yourself, how does your back feel” I said as I walked around the side of the table knowing that I’d earned a brownie point, she took a breath and I could tell she was feeling special..
Jessie: “Aww that’s so sweet darling, hard is good though right and you do have some nice equipment, and yes my back feels a bit better” she said and I could tell the excitement in her voice..
Me: “That’s good to hear and I have another method that I’ll do shortly and work on it some more once I’ve sorted out your buttocks” I said as I started to massage her raised arse feeling the soft skin under my fingertips, she was a bit fleshy as you’d expect fem a middle aged woman but that made it more fun..

As I worked one side pulling and pushing exposing her pigmented crack I could see a fine line of hair running up from between her legs to her darkened sphincter which I have to say excited me and I could hear her soft murmuring as my fingers ran down her crack, I could quickly tell that this was a very sensitive area and it wasn’t long before she brought her arms up resting them by her sides..
Jessie: “Oh that feels so good darling, oh yes” she mumbled as I worked my hands down the backs of her thighs and back up the inside slowing down as I reached the top and feeling the wetness of her hairy labia and then slowly easing back up into her crack, I could feel her body tremble as I hit all the right spots and as her hand eased over she quickly wrapped her fingers around my shaft feeling it regaining its strength..
Jessie: “Oooh I think you’ve found the problem area there darling, spend as long as you want there” she said as my finger massaged around her softening hole and it made me wonder how many toys she’d experimented with up there which is all well and good but I was going to give her the real thing..

She was showing all the right signs which didn’t surprise me with her being in the industry that she was, you don’t get prudish women selling adult toys and paraphernalia so I knew she was up for anything and after finishing one side I moved around the other to give the same treatment paying close attention to her softening starfish and I could tell the scale of her enjoyment by the pressure of her squeeze on my penis..
I will happily admit that I am very partial to a nice arsehole as gross as that may sound but I grew up with parents and a sister that taught me well and also enjoyed that activity so my experience far outweighed my years which I think Jess found very interesting and even pushing a finger inside her gave her much pleasure but it t was now time to move on..
Me: “I’m going to lower the back end of the table now Jess and work on your problem areas from a different angle” I said grabbing the remote and I could tell from her body language that she hadn’t been treated with such attention like this before and as the table smoothly lowered she was soon in the perfect position for rear entry, but I wanted to taste the delights first..

I knelt down behind her and reached up rubbing my hands in a circular motion around her fleshy cheeks spreading them wide as I did so exposing her succulent ring that was crying out to be licked and with her exposed lips glistening in the dim lighting just below I moved in taking a head full of her musky scent with just enhanced the euphoria and when my tongue made contact she very nearly jumped out of her skin..
Jessie: “Oh fuck yeah, I so love this darling” she cried out enthusiastically as I got my tongue working on her dark pigmented hole feeling the softness of her fine hairs on my tongue..
I paid the most attention to her ring but did flick down to her pussy a few times but I could tell by her body language the was lost in her own dreams and after a good few minutes rimming her now soaked arsehole it was time to move on..
I slowly rose to my feet grabbing hold of my not so secret weapon and gently ran it down her crack keeping it wide open with my other hand and then as I found my position I eased it inside her much to her very audible delight..

Jessie: “Oh god boy, you’re good with that tongue and yeah, get that cock in me.. I love it there” she gasped as I pushed further into her finding it a very comfortable fit which confirmed to me that she’d had plenty of plastic up there in the past, I was in deep and could feel my balls swinging back and forth as I gave her long and hard strokes which she seemed to like..
Jessie: “Yeah baby, fuck my arsehole, give it to me darling.. that’s it.. ram that cock into me” she cried out enthusiastically as I started to give her a damn good pounding, there was no pretence, no innocent games with Jess, she liked it and she wanted it hard..
I didn’t have to use the transfer of energy line with her, she wanted fucking and made no secret of that fact and the massage had basically gone out the window as I hammered away at her, she was loving it..
My orgasm eventually came but although intense it wasn’t as intense as I thought it would be but it did leave Jessie gasping and almost screaming in delight as I filled up anal cavity and with sweat dripping off my brow and both of us needing time to gather some composure it was all but over..

I returned the table to its original position and walked back to the head of the table and Jessie raised her head looking at my genitalia..
Jessie: “Wow darling, that was just amazing but I got to ask you.. do you give that sort of treatment to your family too.. just the thought of that makes me wet” she asked and she deserved an honest answer..
Me: “Oh yes, we’re a very close family and I do like to give the full treatment, they actually encourage it” I replied which she found very interesting..
With time getting on and realising I’d spent far too long on her back there wasn’t time to do the front but I think Jess had experienced enough to offer a good recommendation, she had to get ready for a party and didn’t even stay for a coffee making me wonder if I’d done something to upset her, time will tell on that one..