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Tales of a Mature Prostitute Ch. 01

By: GabbyBX



Let me introduce myself: I work under the name of Gabby and I am a mature (60+) prostitute who specialises in clients with erection problems. (I could call myself by all kinds of euphemisms but, at the end of the day, I am a prostitute.) But before we go any further, let me make it clear that this is not an advert for my services because my diary is more than full and my client list is closed. 

I do what I do primarily because I need the money, but I won't burden you with how that unfortunate situation came about. Even if this was not the case, I would hope to have a few gentleman friends whom I could take care of, just because I'd get very aroused in doing so and it would give me tremendous satisfaction to please them (and myself).

I've decided to write this short piece about what I do in the hope that there are people out there who might identify with what I have to say and so gain some re-assurance that the problems of aging are not necessarily an end to sexuality. 

Before I continue, perhaps you would like to know a little more about me (If not, just skip this and the next two paragraphs.) I have a university education which was followed by a career in the arts from which I retired some 10 years ago. I am twice divorced but have no children. 

I was introduced to swinging by my first husband and that lifestyle was renewed with my second husband. As a result and by choice, I am sexually flexible. While there are activities in which I don't wish to participate, there is little that I have not encountered at some time. 

Despite the accumulation of years, I take good care of myself and am in reasonably good shape. There are a few too many saggy bits for my liking but I don't have very much excess weight and only a few wrinkles. I'm on the petite side with medium length dark hair that is naturally wavy. I don't have big boobs but my nipples are relatively large and dark coloured. I keep my pubes well trimmed and shaped, my inner lips are also dark coloured and on the long side, and my clit protrudes a lot when I am turned on. My bum and thighs are still well toned and probably my best features. 

As I have already said, the main reason I got into prostitution was the need for money, which was essential to maintain my standard of living. I was of the opinion that there was a niche in the market for women who would cater for older men, especially those who had wives that had lost interest in sex. And then there were those with whom aging was catching up while erections were going down. I tried various discrete adverts in the local paper but I didn't like the responses I received. They were along the lines of "How much for a fuck?" and "Do you do anal?" which were not the kind of services I wanted to provide. 

Eventually I hit on a form of words that got some attention from the kind of men I wanted to attract and the day came for me to entertain my first client in my apartment. On the telephone he had seemed very nervous, even more than me, and he was no less so when he arrived. He was probably in his sixties, greying hair and a little overweight, and very well dressed and groomed. He paid me my fee for a 1 hour session, I offered him a drink which he accepted and we sat down to talk. 

It was clear that the situation of prostitute and client was new to both of us and it took a good 15 minutes and another drink before I managed to turn the subject to sex, as I felt obliged to do. That's when his floodgates opened. For the next hour, with ever deeper intimacies, I heard the story of his sex life and all its disappointments. 

We were well over the hour for which he had paid but I wasn't concerned about that; I wanted to give him some value for his money. I pointed out the time and told him that we needed to bring things to a close but that I really wanted to please him in some way before he left. I asked what he would like and he thought for a while. Almost apologetically he said that it would be perfect for him if I would lift up my skirt and bend over for him to masturbate on my bottom. 

I told him that it would be my pleasure and he asked if I had any massage oil, which I duly provided. Looking around the room, it seemed that the best place for me was against the back of the sofa and so that is where I positioned myself. He walked around behind me, I slipped of my g-string, raised my skirt and bent over with my legs apart. To say that I felt vulnerable would be an understatement. I would have been more comfortable if it had been straight sex but this was what I had let myself in for and for which he had paid. 

I didn't look around but I guessed he had dropped his pants and was lubricating himself so I thought I had better do a little more than just stay still. I stroked the backs of my bestockinged thighs, slowly wiggled my hips and ground against the sofa. From what I could sense he was rubbing himself and quite close to me, and he was telling me how good I looked. It went on like that for a few minutes and then the sounds I heard suggested he was increasing the pace of his wanking. He told me he was very close and asked me to spread my bottom apart. I did as he asked and a moment later I felt his cock head and his hot cum on my bum hole. He was groaning and seemed to be trembling as he unloaded against me, and I have to say that my pussy juices were flowing. 

When it seemed to be over, I stood up and went to the bathroom to get a towel. He was in the process of re-dressing himself but I insisted that I clean him up and knelt down in front of him. His dick was very sticky with oil and cum and had shrivelled to a very wrinkly little thing but I did my best to clean it before he put it away. 

I think he was a little bashful and embarrassed but he assured me that it had been the most erotic experience of his life and that he would like to return to do something with me again. After a visit to the bathroom, he finally left. 

For me, I had an enormous sense of elation that things had gone so well and, alongside that, I was very aroused. There was only one thing for it: a session with the dildo and vibrator. I went to the bedroom, dropped my skirt, took out the toys and started to play with myself. There was no need for lube to get the dildo planted inside and the vibrator had my clit sticking out in no time. Thoughts of my earlier vulnerability, the lewdness of the way I had displayed myself and the sensations of his cock cumming against my most private place brought me to a very fast and furious orgasm. 

For all my experiences of swinging, and all the excitement and orgasms that I had in those days , I never had an encounter that touched me much as that with my first client. And what's more, when I went to the bathroom, I found he had doubled my fee. 

As I have developed confidence, and my client base has expanded, I have had many varied experiences with older men, almost all of which have been intensely personal and intimate. If enough people are interested, I will take the time to relate them in detail -- just send me a message so that I know where I stand. 

Thank you - Gabby. 

Tales of a Mature Prostitute Ch. 02



Looking back in my diary, after my first client, I entertained nine other men over the course of the next three weeks. Mostly there was a good outcome but there were a few that I considered so-so. Importantly for me, nothing bad happened. I think two or three are worth writing about but I'll leave them for another time. 

It was my eleventh client, a man I will call Harvey, who is especially memorable because he introduced me to the idea of using internet porn with my clients which has been a foundation stone of my repertoire ever since. He also deepened my understanding of how men's sexuality can change as the years pass by. 

In my adverts I try to make it as clear as I can that I am interested in older people and that penetrative sex is not on my menu, and I clarify in straightforward terms when I answer calls. For Harvey that was more than OK. What he wanted was for me to look at and talk about internet porn with him. 

Did I have a computer, could he bring a CD and would I wear a short skirt, fishnet stockings and stilettos? Yes, of course, and what else? A short pause and then the answer: would I masturbate with him? Yes, I would. Would a two hour session be OK? Yes, and thank you for being so specific, and can we agree on a fee?

(I do understand that many guys are reticent about asking for what they would like and that I have to coax it out of them as part of the service, but when a client is specific, there is a great chance that it will work out well for both of us.) 

Dressed as he'd requested, with the addition of a blouse that exposed a good amount of cleavage, and generally looking rather too sluttish for my liking, I opened the door to Harvey. He had told me he was 61, and that is more or less how I would have placed him. He was quite short and stocky, a full head of silver hair, a round, flushed face, a nice smile and a confident stance. 

Over the preliminary drink, he told me in a very straightforward manner that his only source of sexual gratification was masturbating secretly to porn. His wife's libido had dropped to zero after her menopause, and his erections weren't up to the job anyway. He had tried the blue pill but it made him feel ill. He'd fantasised about looking at porn and masturbating with someone else, saw my advert and decided to call me to see if I was interested. He loved his wife dearly and didn't think he was cheating on her because his arrangement with me was purely professional. 

During our chat I had been sitting opposite him. Even if I had wanted to, wearing a short skirt made it impossible to avoid the display of leg and stocking top that I was giving him, and that is what brought the conversation to an end. He told me that he was getting aroused by what he saw and asked if we could go to the computer.

In my study, everything was prepared: two chairs covered by large towels in front of the screen; baby oil; a silicon, cock-shaped vibrator; water-based lube; and a few hand towels. Harvey seemed to approve, commenting on how well prepared I was, and I loaded and opened his CD to find a folder named For Gabby. We sat down and I passed him the mouse.

In a couple of clicks the image that appeared was of a MILF type of woman perched on the edge of a desk dressed in an outfit that was remarkably similar to mine. I commented that she was lovely and would like to see more of her. Another couple of clicks and there she was again with skirt around her waist, one breast out of her blouse, her legs apart and her bare pussy on display. Harvey said that he liked up-skirt shots and I asked him what he liked best about her; as well as her outfit and pose, it was the shape of her thighs and the way her pussy looked so delicate and tight. I suggested that, if she was sitting in front of us, we could each use a hand on either side of her lips to open her up and then he could slip a finger inside her and, when she loosened up, I could slip one of my fingers into her, alongside his. He asked me if I'd ever had it like that and I told him that I had but I didn't pursue it. Rather I suggested that he might like to get some clothes off. 

Together we undressed him so that he was only wearing a polo shirt (as I insisted he remove his socks - a prejudice of mine). His cock looked thick and swollen but far from what I would call a hard-on. 

As he clicked on the next image I hitched up my skirt and slipped off my g-string. The picture was of the same MILF lady, this time bending over the desk with a hand reaching around to spread one of her cheeks and expose her rear entrance. It immediately brought to mind the session with my first ever client when I had posed in a similar fashion. Harvey seemed unsure where to look but I was sitting with my legs together so there wasn't much of me for him to see. 

I thought about telling him of my first client and how I had exposed myself but decided against it. I learned a long time ago that talking to a man about sex with other men was not such a good idea. It tended to arouse either jealousy or their competitive instinct and in the case of Harvey, the last thing I thought he needed was to feel that he had to prove his virility.

We browsed through more similar pictures, me stroking his thigh and him unable to resist touching himself from time to time. It soon became clear that he had a liking for women in stockings bending over with a rear view of their pussies. As he relaxed with me, he spoke more about what was on the screen: the crease between buttock and thigh and the swell of thigh flesh at the top of a stocking; the curve of a narrow waist swelling into rounded hips; the definition of a well-toned leg and, of course, the slits between their legs. What I liked about all of this was the detail he noticed and the way he described it, and how he seemed to be relaxing with me, feeling free enough to talk about it all. 

After a while he asked me if he could show me something that was a little more hardcore. I told him to go ahead and up popped a close-up, black and white picture of a wet-looking pussy, spread open, with a large, hard cock just at the point of penetration. I immediately responded by saying that the first thrust was always the best because you knew that you had been taken and there was no turning back. Harvey smiled and said that it reminded him of when he was younger and could get it up without a second thought. 

I didn't think it was good for him to dwell on the past too much at that moment, and we were well over an hour into the session, so I decided the time was right to touch him and keep him in the present. I reached out and wrapped my hand around his cock, feeling that lovely, velvety, warm flesh. With my fingers close to the base of his shaft, I slid my hand downwards to ease his foreskin back and gave him a soft squeeze which managed to get the head to swell a little and caused him to murmur in appreciation. I told him that, if his cock could talk, I was sure it could tell all kinds of stories and that it would soon have a new one to add to the index. 

As I fondled him, he turned back to the computer and clicked on a series of images of women masturbating, and finally of a man and woman sitting opposite each other, both of them jerking off. It was what he had fantasised about a lot but never experienced, he told me. 

At that point there was little more to say but plenty to do. I moved my chair back so that it faced him, eased one breast out of my blouse, squeezed a little lube into my right hand, slid down to the edge of the chair and parted my legs. Harvey lubricated his cock with baby oil and our mutual masturbation began.

I'd much enjoyed scenes like this in the past for their certain, special intimacy but like many things in a sexual encounter, for me it depended on the context, the man and his demeanor. Harvey was far from the answer to a maiden's prayers but I liked him and enjoyed the rapport we had created. His body was not unattractive and I liked his strong looking thighs and especially his hands which at that point were smoothly and steadily stroking his cock. For all that, I thought I might not achieve a real orgasm for him to see; the context just wasn't right for me and perhaps things were moving too quickly. My focus had been on his pleasure rather than my own and I wasn't particularly aroused. I decide to take it a step at a time and see what might happen.

Harvey was supporting his cock with one hand wrapped tightly around the base and the other rubbing up and down the shaft. On the downward stroke the head would show itself and it looked very purple and bulbous. I was massaging my exposed breast with one hand and a finger of my other hand was stimulating the magic spot at the upper left part of my clit. From time to time I would place a finger on either side of the hidden stem and pull the hood back so that the pink tip would show itself. With a little of such attention, my clit engorged so that the tip was permanently displayed. 

Perhaps it was the sight of my miniature dick that did it for Harvey because he was no longer needing to support his erection with one hand at its base; it was standing up all by itself, his strokes were getting stronger and he was moaning and sighing. I encouraged him to continue, telling him how big and hard he looked and how much I liked the way he was rubbing it. 

It seemed to me that he was getting close so I quickly grabbed the vibrator and added some lube. Raising my thighs onto the arms of the chair and parting my pussy I began to slide it inside. As my pussy gradually accepted the penetration, I started to deliberately fuck myself, easing the vibrator back slowly and then pushing it back firmly in, all the time with Harvey's gaze riveted on the action. It didn't take him long to cum, first a loud groan and then a series of many little spurts each accompanied with a gasp. His face was that amazing combination of agony, pleasure and relief. For a good few moments he sat quivering and taking deep breaths before finally slumping back into his chair with his eyes closed and a hand gently fondling his softening dick. He looked quite exhausted. 

After watching his display, I was more aroused than I had been at any point in our session. With more time I would have easily got myself off with my fingers and the vibrator, but it wasn't to be. 

I let him take his time to come around and when he opened his eyes he kept repeating that it had been amazing. I asked what he would like and he said a strong black coffee and a cigarette. 

Before Harvey left, we chatted for a while and I was especially curious about what he had said earlier: that he was no longer up to the job. On the other hand, I had seen him maintain a very solid erection for a good period of time. He explained that it was a combination of things: my talking so explicitly about sex; the visual stimulation of the porn and then the way I had exposed myself, live in front of his eyes, just for him; and that he didn't feel any pressure about having to perform. It was interesting feedback which confirmed many of the things I had read. 

I had hoped Harvey would return and I'd thought about how I might develop things with him but I have never heard from him since. Who knows? 

PS -- A big public Thank You to all of you who sent me such great feedback on my last story. I hope you enjoyed this one just as much. 

Next time, I think I will tell you about encounters where my participation is very passive and about a client who wants nothing more than to please me. 

A final thought - in one of the feedback messages, I was asked about my reasons for writing and it occurs to me that others might have a similar query so here is how I answered: 

"You ask why I write - a good question and one that I asked myself. The superficial answer is that I like writing and I like sex. Looking a little deeper, there are a number of factors which fit together to provide the motivation.

Acceptance is important to me. Anyone involved in sex work knows that many will look down on them, so there is a strong need to find a pocket of society where you are accepted. Idealism is another factor and in writing honestly about sex amongst older people, I hope I am waving the grey flag. And then, I have always been involved in the arts (don't get me wrong - I'm not trying to pretend that my writing is great literature) and, in common with many in that field of life, I have a strong urge to give of myself, in some ways to provide a counter-balance in a world that often seems dominated by takers, and also it ties back to wanting acceptance." 

Until the next time -- Gabby.



Tales of a Mature Prostitute Ch. 03



I am now well into the second year of my new career and have a good number of regular clients. Many of them like to talk at length and sometimes a session ends without anything sexual taking place at all. At times I feel more like a therapist than a sex worker but I'm not qualified for such a role so I tend to offer empathy and encourage them to keep talking rather than trying to make any smart psychological intervention. 

Mostly, I am a very active participant in the games my clients like to play but there are many occasions when I am required to be passive. The most common situations involve my feet and legs, and shoes and stockings. One of my regular clients likes to worship my stockinged feet and calves, stroking and licking and rubbing his cock against them, while I pretend to be oblivious of his attention, reading a book or watching TV. I have forgotten to wear panties so he gets an upskirt view as well. By the end of the session he "accidentally" cums on my feet, I chastise him and make him clean up his mess and then send him away. 

With another client it is a similar feet and legs scenario but I am fully engaged and instructing him as to what I would like. I have to say that he gives a wonderful foot massage, which ends with me asking him to give me some of his "special protein enriched lotion" to keep my feet in the best possible condition. 

Stocking tops and that gap of naked thigh between them and my pussy is another popular area of attention. And my bottom is never short of its admirers, as I described in my first story.   

In all of these little scenes, I know there are those who would say that I am not only degrading myself but also degrading all women by allowing myself to be used as a sex object. I don't choose to frame it in such a way at all. For me, the sight of a man masturbating is a compelling vision of masculinity, and I get a powerful surge of exhilaration when it is my body that it is providing the stimulation for him to cum. 

...

Once in a while, I have a new client with whom I am surprised at the outcome. One such client was "Greg". He called me and said that maybe I would benefit from a full body massage and would I like one. It was a curious choice of words but I went ahead and gave him my standard piece about non-penetration. He said that there was no need to worry because he always respected boundaries. We agreed on my fee and he booked a session with me, but something about his approach made it seem that it was me who was hiring him.

I have a regular client who also likes to give me a massage. He gives me a nice back rub, works his way to my bum and eventually cums between my thighs. With Greg, however, I suspected it would be something a little different. 

When Greg arrived, the first thing he did was to take an envelope from a small leather bag he was carrying and to hand it to me, saying it was my gift. He then asked to use the bathroom and, of course, I checked that the envelope did indeed contain my fee, which it did. I realised that his visiting the bathroom was to give me the opportunity to count the money and it was clear that he wanted to control things.

He declined a drink but we sat and talked, unusually with the emphasis being very much on me. He was an attractive man, medium height and slim, probably in his early sixties, and with a soothing, deep voice. After a short while, he got around to asking if I had a problem in reaching orgasms. Despite that I have never had such problems, I somehow knew that the answer he was looking for was a "yes", so that is what I gave him. 

He nodded knowingly, saying that it was very common for women in my line of work. He went on to say that his massage technique was especially designed to help cure my lack of orgasmic response and he was sure that it would be of great benefit to me. 

We moved to my bedroom where I almost never entertain clients but for a full body massage I had no other option. I had prepared by spreading a large towel over the bed, setting the heating to a nice temperature and spraying the room with a soft-smelling perfume. He looked around, nodded his approval and asked me to undress. As I did so, he began to do the same, explaining that it made the job easier for him and that he didn't want to get oil on his clothes. He stripped down to a pair of blue briefs which he didn't remove. His body wasn't especially muscular but he looked very fit and toned with a light tan and little body hair.  

He took a bottle of oil from his leather bag, asked me to lie face down and then straddled my hips. At first I wasn't too comfortable with the situation because it gave me very little control over what might happen. I think he sensed how I was feeling and talked about trusting him. He began with my shoulders and upper back and it was soon clear that he knew what he was doing. There was no need for me to pretend because he had the touch of an expert and somehow it did ease my concerns. 

As he worked over my body, down to my lower back, then up from my feet and along my legs, inner thighs and finally my bum, he talked throughout in his lovely soothing voice which seemed to match the rhythm of his hands. I have little idea of what he said because I was getting into something of a trance, though his hands on my buttocks aroused some very sensual and erotic feelings.  

The time came for me to turn over and Greg dismounted from his straddle. He took a pillow and said he wanted it under my hips. When I was arranged to his satisfaction, he half sat, half knelt on the edge of the bed by my side. He told me that he could sense a lot of sexual energy in my body and that he was going to gradually focus it and then release it. I translated this in my mind as meaning that he thought I was getting turned on and he was going to get me off. I had to hide my smile, though I had little doubt that he would succeed so I closed my eyes and let him get to work.

He didn't dwell for long on my breasts but found all those zones that seldom get attention: the sides of my waist and hips; inner thighs; lower abdomen just above the pubic bone; and the V of the creases between my thighs and tummy. I was unaware that I had parted my legs so much until his hands found my outer lips which he massaged and softly pinched for quite a while and which was especially arousing. By the time he got to my inner lips, the tip of my clit had popped out and was screaming for attention. He knew exactly where to find the magic spot (upper left quadrant, in common with many women) and with some soft pressure and slow rubbing I had my first orgasm. 

I was still trembling when he asked me if he could insert a finger because it would give me another orgasm. I told him to go ahead, one of the few occasions when I have allowed penetration. 

He maintained the pressure and rubbing on the side of my clit, slid a finger inside my pussy and found my G-spot. I think it is easy to find when I am in a state of arousal. He gently circled it with the tip of his finger and the pleasure was so intense that I didn't so much have a second orgasm as a continuation of the first. 

I'm often asked what it feels like when I cum but I find it very difficult to describe and also it varies. Sometimes it is nice and quivery; other times, when I am really aroused, it is a full body release; and then there are the ones which are in between, such as with Greg, but I didn't tell him that. 

I felt drained at the end of it all and would quite happily have fallen into a one of those lovely post orgasm sleeps but I had to remind myself that I was with a client and not a lover. I roused myself and sat up to see a very self-satisfied smile on Greg's face. 

He said that he was expecting a knock on the front door from the neighbours because I had made so much noise and he asked if I realised that I had ejaculated a little. I know that I do that sometimes but I wasn't aware of it at that time. Nevertheless I pretended to be amazed and sure enough there was a very damp patch on the pillow beneath my hips.

I felt obliged to ask what I could do for him though I really didn't want to do anything more. He said that I had already done it and then stood up for me to see a damp patch on the front of his briefs. It was quite a surprise because, as far as I knew, his hands had been busy with me the whole time. He didn't seem to want to explain so I just smiled and said that it was amazing. 

Before he left, Greg told me that his treatment would have opened up new passages through which my sexual energy could flow and that I would have a lot easier time in future in reaching orgasms. Of course, I thanked him profusely and left him with his fantasy. I have not seen him since and somehow imagine that he is working his way through all the other women in the area who are in my line of work. 




PS – Many thanks again to all those who sent me feedback on my last story; it is much appreciated. And an extra thank you to the ladies who responded – I put great value on your interest and the thoughts you share with me. 

Until next time – Gabby.



Tales of a Mature Prostitute Ch. 04



As I've explained before, I specialise in entertaining older men, and offer "outercourse". Most people understand that means non-penetrative sex but I always stress the point when taking calls from new clients. 

I live close to an upmarket retirement "village" which has around 600 units, and there are also many retirees in the larger area. The vast majority of my clients are well-funded for their late years but, unfortunately, as they have aged, their bodies no longer respond as they would like, though they have not lost the desire for sexual contact. The problem for them is that they don't have an understanding and willing sex partner, even though they may have wives. 

I never want more than two clients a day and I rarely take weekend bookings. Demand exceeds supply but I'm as busy as I want to be to maintain a good standard of living. If all that sounds mercenary, well, I suppose it is, but I put a lot of effort into what I do and I think I provide a service that is very much appreciated. 

As well as those men who have age-related erection problems, there are those that seem to suffer from performance anxiety. I hear about this from several men, even those that are somewhat younger. In summary, the problem seems to be that fear of not getting or of losing an erection actually cause it to happen. To compound the issue, they feel bad about not being able to satisfy the woman they are with, let alone themselves. I think it is one of the reasons that, by offering only non-penetrative sex, I attract some clients, because with me they don't feel that pressure to perform.

Some of my clients take Viagra before seeing me, others have tried it but don't continue with it because of the side-effects, and others just don't wish to use it. From those that use it I have learned a lot about the do's and don'ts and perhaps some readers would like to hear about such things. If not, just skip the next paragraph.

Please don't take what I have to say about Viagra as a qualified medical opinion; it is just the experiences that I have been told about over a period of time. The first thing is that Viagra does not combine at all well with alcohol, which negates its intended effect and aggravates side-effects like stomach acidity, nausea and blurred vision. Then there seems to be a recommendation that it is taken on an empty stomach so that it is more easily absorbed into the system. Although it can work after twenty minutes, they say it is best to wait for about an hour. As regards dosage, I have heard that more is not necessarily better, again because of those side-effects. Finally, it is not an automatic erection generator; without the right kind of stimulus, a cock will still not respond. 

So now I think it is time to tell you about what engages me by far the most with my clients and is the reason I think I am soon going to need a wrist support. 

I never gave it much thought but, for years, I just assumed that a man needed a proper erection in order to cum. It was an older lover who taught me otherwise when he had an off day and couldn't get it up. To my surprise, I was able to make his semi-hard cock cum with my hands, following his instructions as I went, and it seemed to me that he had an orgasm that was even stronger than normal. It was fascinating. (I must add that he was a gentleman and afterwards saw to my needs as well.) 

If I were to write about every handjob I have given, I would be here for months so I will have to generalise. The most important thing for me is to discover what really turns on the man to the extent that he is going to reach a good, satisfying climax. This is very individual and small details matter. 

The most common subject material is anal sex. It enthrals the majority of my clients and many like to know how it feels for the woman, step by step, from the initial probing finger to the final few thrusts. I think that for those who have only seen professional porn, my descriptions are quite a revelation. 

The second most popular topic is spanking (maybe I'll write about that at another time, if sufficient people indicate an interest.) and then there are a host of other things, lesbian sex, and sex with older women being quite popular. 

As I have mentioned before, it is the internet that plays a major role in most of what I do and my study, where I have my computer, is where most sessions take place. Before getting started with a client, I'll get him out of as many cloths as he wishes and I'll be down to a g-string, stockings and heels. I'll sit on a chair by his side and we'll look at some internet porn images for a while, with me stroking his thigh. I usually do most of the talking, at least at the beginning, trying to create a relaxed and fun mood, and being quite explicit about what we are looking at. 

We'll then move on to watch a video clip, usually one that he has brought along, and by this point I will start to fondle his cock and balls and apply some baby oil so there is physical stimulation as well as visual and verbal. 

If he gets hard quickly, usually because he has taken Viagra, I know I have to go easy for quite a while and will just use one hand to gently stoke the shaft. The challenge is to find the balance between keeping him hard but not getting it so stiff and sensitive that he cums all too quickly, and much before the end of a twenty minute video. 

If he is soft, I'm much more busy. I'll use two hands, one to at the base and the other around the head. I'll be sideways to the screen so I will have to keep glancing around to see what is happening so that I can talk about it. With the hand at the base stretching back the loose skin and squeezing, and with my other hand sliding around the tip, I can usually create a pseudo erection. The tricky part is getting the right grip at the base and I will often ask my client to do it himself while I concentrate on the swollen upper half. 

As things progress, it becomes a matter of timing because ideally I'd like my client to cum at the same time as the guy on the screen. This takes good teamwork and I'll ask if he wants his cock rubbed harder or faster or whatever. I will often be kneeling between his thighs so that I can't see the screen and some clients will give a running commentary. 

With men who find it difficult to stay hard or pseudo hard, they will sometimes take over the job themselves and then ask me to give the final strokes to finish them off. Those final strokes can vary as well. Some want them hard and fast, others slow and squeezing, and still others just want their cock to be held. And then there are different kinds of spurts, which vary between volcanic eruptions to meandering woodland streams. 

Like many women, I find it incredible how something that starts off so small and soft and pliable can turn into something so big and hard, especially so when it is gripped and held at the base. Quite amazing! 

I don't like to take facials but I'm OK with having my tits splashed and pressed against because I like the lovely feeling of warmth that comes from a well rubbed cock and fresh cum. By this time I have a great sense of achievement for what has been accomplished, even if I have a very tired wrist. 

As you might imagine, there are many variations on what I have described. What starts out as a handjob may turn into mutual masturbation or the guy finishing himself off on my stocking tops or bum. 

Two of my regular clients never get hard at all, not even a pseudo erection. With them I will play with their cocks for a while but I have still to learn how to get them to orgasm. I just can't get the right pressure and pace, and so they do it themselves. I find it quite fascinating to see a flaccid cock cumming and they say it is just as intense as it used to be when everything was in full working order. 

One of my clients always arrives pretending to feel very dirty and sweaty and so needs to take a shower with me. His cock is especially dirty and so I have to give it a thorough wash, which somehow just happens to cause it to let loose a jet of sperm. Fortunately for my water bill, he cums quite quickly. Afterwards, he talks about his day as if nothing had happened and then goes on his way.

If, like me, you have an interest in useless information, then I calculate the following: 

assuming that a man ejaculates 5 millilitres of sperm when he cums, and given that I have entertained an average of 8 clients per week for 80 weeks, then I have overseen the production of more than 3 litres of sperm. 

Through all the encounters I have described in this story and in my previous efforts, I would describe the sex I give as being social. It's not the kind of sex that starts or ends with cuddling in bed together, whispering sweet nothings; I don't think it would be very professional of me to go in that direction. I am well aware that some clients would like to get personally close to me but that's not what I want because I am more than happy with my private life as it is. I have to guard against encouraging anything that might suggest otherwise while still giving them what they pay for. It can be quite a challenge but it's part of the job. 

Thank you again to all those that have sent me such positive feedback. I'll write more soon. 

Gabby.



Tales of a Mature Prostitute Ch. 05



Hello again,

At last there is some peace and quiet after a busy spell of ups and downs and time to do a little more writing. As I mentioned to several people who emailed me, I thought that some readers might be interested to hear about encounters with couples, of which there have only been a few. (From what I read on various blogs, a number of escorts are reporting that "couple-calls" are on the increase with some saying it is around 10% of their business. I wish I could say the same and I have modified my advertising -- let's see what happens.) Before I tell you more, I think I must offer a little about my background, an extract from my sexual CV or resume, in order to provide some context. 

It was back in the late 1960's when I was introduced to wife-swapping, as it was then termed, and I had my first serious encounters with women. Many of the "swapped" wives were not at all bi-sexual but most would accept a little physical intimacy as part of proceedings. And then there were a few, including me, who were as much interested in the other wife as in the husband. One of them with whom I had a short fling, an actress, later made a name for herself on British TV. With another I had a 1-to-1 relationship that lasted for several years and, since then, there have probably been as many women in my life as men. 

Today in my personal life, my favourite sexual activity is to join with a certain couple that I have known for several years. 

*

The three couple-calls I've taken led to four sessions and were all from people on vacation (I live in a small resort town). On the first call it was the wife who spoke and she was very specific in describing what she wanted. Clearly, it wasn't the first time she had hired someone like me. 

I met them in their hotel room where she greeted me dressed in a bathrobe. She was quite tall, at least in comparison to me, gaunt and probably in her 50's. Her demeanour confirmed what I had gathered from her call: that she was used to being in charge. I imagined people got used to doing her bidding. She handed over my fee and ushered me into the room where her husband, also in a bathrobe, was sitting in a corner, just as she'd told me he would be. He greeted me with a smile and a nod, and with no more ado the wife asked me to undress. She looked me over, said I was very nice, then removed her bathrobe to reveal her own nakedness and guided me to the bed. 

From there things progressed just as she had described which amounted to her playing with my body whilst her husband fucked her. I lay on my back with her straddling me and her hands began to wander, stroking and squeezing and exploring. It was very impersonal, much like an examination, and she made no effort to arouse me, but it seemed to turn her on. 

After a short time she was down at the bottom of the bed on her knees between my legs and spreading my pussy, no licking just fingers, and that is when her husband came into the picture. Gradually he entered her from the rear and began at a slow pace. At this point she was resting on her elbows and she asked me to play with myself. Both of them had a clear view of me and before very long he was pumping into her quite vigorously and she was grunting and groaning. She had a hand rubbing between her legs and her gaze was fixed on me so it was easy to tell when she started to cum and I pretended to do the same. Her husband followed very soon after. 

The whole thing had lasted barely half an hour but they seemed happy enough and for the first time I saw her actually smile. I was more than happy to get back home. 

The second couple-call led to two sessions with a middle-aged man and wife, both somewhat over-weight and not especially attractive. My role was little more than being a hand maiden, letting them see my body, playing with the husband's cock while he fingered her and then getting my hand between them to hold it while he fucked her. It was quite awkward because of his plump stomach and small cock, and all I could do was grip him between the V of two fingers; even then there was no real depth of penetration. It would have been far better if he'd taken her from behind. When he was ready to cum he pulled out and I jerked him off which seemed to please him well enough. The wife was very indifferent, not surprisingly because it was all about him, but at least she acknowledged my efforts in a kindly way. 

A follow-up session with them was mutual masturbation, the three us watching each other play with ourselves. The wife was much happier this time and talked a lot more. She used a vibrator on her herself and offered one to me but I said that I preferred fingers. We sat in a triangle, the husband perched on the side of the bed and the wife and myself in chairs. Obviously, I was the centre of attention because that is what they had paid for. If you have read some of my earlier tales, you will know that it is a performance that I am well accustomed to giving, though very rarely for a female spectator. 

So now let me get to Deborah and Paul and I'll describe what happened in more detail because it was a session that I enjoyed a lot. Paul made the call and explained that he and his wife were on vacation, that her greatest fantasy was to have an older woman make love to her and "take her lesbian virginity". They had seen my advert in the local paper, thought that I sounded a little different to the others and perhaps Deborah's moment had arrived. Would I be interested? 

Yes, of course I was interested but how would he fit in to things? He said he would be there, just to hold her hand, if that was OK by me, and he understood from my advert what the limits were and had no intention of even approaching them; it was about her, not him. I agreed a fee with him and that I would meet them in the bar of their hotel but I wasn't happy that all the boxes had been ticked. Paul, with an English accent, sounded like a nice man but it had all been a bit too perfunctory for such an important event for Deborah so I asked to speak to her. 

Straight away, I was struck by her lovely, soft, North American voice and she told me she was from Vancouver. I said that Paul had told me what they had mind, which of course she would have overheard, and that it was not unusual (though in truth it was for me in a professional context) and I would love to meet her. I went on to suggest that I felt it was important that she took a liking to me and that it might be best for both of us if she could check me out without any commitment. She seemed to understand exactly what I was getting at so I suggested I would appear at the hotel bar, sit at the counter and they could stay anonymous. If she liked me then she could approach me, if not they could walk away. I could have a drink with them and at that stage she would still have the option to back out. She was concerned about wasting my time but I persuaded her that it would really be best for both of us because if we weren't comfortable together then it would not be much fun. In the end she agreed providing that I would also feel free to walk away.

Two days later, at the appointed hour of 8.00pm, on a warm evening, I entered the South Beach Resort and Spa Hotel, probably the best in the area. I walked through the foyer and out across the pool deck which led to the patio of the bar with its busy tables. I'd given Deborah a description and added that I would have a turquoise and orange bracelet on my right wrist and be wearing loose fitting light pants -- pretty standard evening resort wear. I avoided looking around except to choose a spot at the bar counter, declined to order a drink and wondered how long I would have to wait for Paul and Deborah to make their evaluation of me. Thankfully, it was perhaps less than a minute before I sensed a woman in a pink dress approaching from my right and then heard a soft Canadian voice asking if I was Gabby. 

She introduced herself with a nice smile, and then led me to their table out on the patio. I was introduced to Paul who was tall and slim, bespectacled, and reminded me of a youngish Michael Caine. He called the waiter and I ordered a glass of Chardonnay (which always reminds me of Sue Ellen). If they were feeling nervous, they had enough savoir-faire for it not to be evident and we slipped into an easy conversation about their vacation. 

I placed them in their late-30's/early-40's, probably professional people and certainly well-educated. They had clearly been enjoying the sun and had lost that city greyness which would identify them as visitors. Deborah especially had picked up colour, her arms and legs looking nicely tanned. 

She was about my height with something of an athletic posture and she obviously cared about her physical condition. Something about her features, especially the shape of her eyes, and perhaps the line of her jaw gave her an unusual ethnic look which I found intriguing and very attractive. She wore only a touch of make-up around her eyes and a light lipstick on lips that I was imagining and hoping soon to be kissing. The pink dress was nicely styled and detailed, and revealed very little, mainly because her breasts were rather small. Her hair was dark brown, naturally wavy and shoulder length, mane-like, and she occasionally pushed away imaginary strands from her face, maybe a tell tale sign of her true feelings. 

As the drinks were gradually emptied, I felt that Deborah had become a little quieter and I sensed that she was stealing herself. To my surprise, at a pause in the conversation, she took the initiative and said that, if it was OK with me, she would like us to go up the room. I think it took Paul by surprise as well. Clumsily, he reached to his back pocket and took out an envelope but I told him that it wasn't necessary. Perhaps for a moment Deborah thought I might be declining so I touched her arm and said that I didn't want to wait any longer either. 

In their room, the air-con had been on full-blast and the place was freezing. I suggested we turn it off and open the doors on to the balcony, and Paul complied. I took Deborah by the hand, led her outside and we stood together for a moment looking down on the pool and out over the sea beyond. It was a perfect setting. 

Deborah and I looked at each other and I noticed a tear roll down her cheek. I took her in my arms and she let out a sob then took a deep breath. She said she was OK, not upset, just the emotion of finally being in the situation that she had imagined for so long. Paul was close enough to be aware of his wife's state and seemed to want to get involved but I shooed him away telling him everything was fine. 

With a little hugging and some tentative kisses she regained her composure and our kisses became deeper and longer. Our tongues engaged in that languid circling dance and I began to explore her with my hands. She was even slimmer and more toned than I had imagined and I told her so. I told her everything I was feeling, about her mouth, about her body, about her perfume, her voice, and the sensuality of it all. And then I asked if I could undress her because I wanted to see her and feel her skin to skin, and she murmured a "yes" 

First I pulled my top off and discarded my bra and then I reached around her and unzipped the back of her dress. I eased it off her shoulders and over her slender hips and it fell to the ground. If anyone down below was looking up at that balcony, they would surely have witnessed a very erotic little scene. But I wasn't interested in anyone else's view, just my own view of Deborah, naked but for a silky red thong. 

I took a step back to take her in, knowing she would feel vulnerable but vulnerability can be erotic and arousing. She was very thin, too thin to be classically beautiful, and angular as well. Her breasts were small but rounded, pert with only a hint of a sag and showing the tan lines of a bikini top. There was no trace of a tummy bulge and her thighs looked strong and capable, almost out of place against her slenderness. To my mind it was the body of dancer. I loved its elegance and I told her so. I had a thought to ask her to turn around but decided against. 

While all of this was happening, Paul had been perched on the edge of the large bed looking quite mesmerised, doubtless beginning to see his wife in a whole new light. As I guided her back into the room, he got to his feet, took her face in his hands and kissed her, telling her that she was amazing. It was very sweet. 

I suggested he might want to get comfortable and lose some clothes, and that he might like to sit in the chair in the corner of the room. From my handbag I took out the indispensable little bottle of baby oil and placed it on the bedside table then pulled back the bedcover (you never know who has done what on hotel bedcovers), slipped off my pants and panties, and held out an inviting hand for Deborah to join me on the cool white sheets. 

We lay together side by side, kissing, murmuring and caressing. I had her lick my fingers, telling her that they were going to explore her body in the most intimate of ways. I got her to taste my tongue because it, too, was going to find its way into all of her crevices. As well, I told her not to be afraid to guide me, to stop me if it became too much, to ask for more when she wanted it. 

Her hands were tentative as she touched me, stroking my arms and shoulders but not sure about where else they might travel. Maybe I was distracting her because my hands were wandering further: the ribs by the side of her breast, her waist, the hip bones -- yes, she liked it there. I freed myself from our embrace and eased her on to her back so that I could really get to explore her. How sensitive were her breasts -- mostly around the upper half; her nipples -- yes, she liked to have them sucked; her tummy, so lean and smooth -- my stroking made her purr; the crease between body and thigh -- a steady rubbing that stretched her skin was getting to her; that area of lower abdomen, just above the pubic bone -- that really caused her hips to rise. 

I straddled her and leant forward, offering my breasts to her mouth and she duly gave attention to my nipples, licking one, then the other and, with a little encouragement, sucking on them in turn. I felt her hands on my waist, a light touch, still unsure, but this wasn't so much about me as about her. 

Cat-like, I crawled down her body, caressing her skin with my nipples and tongue, over her breasts, her waist, her tummy and her thighs until I was at the bottom of the bed where I slid down to kneel on the floor. Time to remove the red thong and she raised her hips so I could free it and slide it down those well-shaped legs. Paul was sitting quite close to me, now wearing just a pair of briefs and I threw the thong to him with a smile. 

Back on the bed, I crawled back by her side and reached for the baby oil. With a slather of it in my palm, I put my hand between her thighs and covered her pussy. She trembled at the touch, took a deep breath and looked at me with wide eyes. I told her I was going to give her a very slow rubbing and then kissed her face and mouth. Her eyes closed and her legs parted, and I began to work on her inner thighs and around her outer lips. There was very little hair and no stubble, just a trimmed landing strip, so my fingers could massage her smoothly along the outer crevices. 

She was responding readily, grinding against my hand with thighs partially closing then opening again. Her breathing was deep and she was moaning a lot but I kept a steady pace, taking my time to prolong things for her. 

I was very close to her face and could see her perspiration, and it wasn't the only part of her that was dripping. She told me she was very close to cumming so it seemed like a good time to go down on her but I wasn't going to rush. If her arousal subsided a little, I was sure I would be able to build it up again because at that point I had hardly touched her clit. I got her to move down the bed so she was at the very edge and I could kneel on the floor between her legs. I told Paul to come and hold her and play with her tits, and I got the chance to take a close look at her pussy. 

I don't think there is a woman alive who hasn't wanted to hear that she is beautiful down there so I gave her a description, in glowing terms, of everything I could see. For you, dear reader, I will give you a more objective view though don't think she was anything but delightful and delicious! She was very wet, swollen and open, especially the outer lips where I had given her so much attention, and she was very red around there. The inner lips were quite small and crinkly and very spread to reveal the pinkest of openings. The stem of her clit was hard but only the tiniest of pale tips was visible. Gently I pushed back the hood which exposed a couple of millimetres at most. I gave it the slightest of flicks with the very tip of my tongue and she responded instantly, almost recoiling -- clearly she was extremely sensitive. If I possessed a cock, at that very moment I would have been unable to resist thrusting it into her, but instead I had to make do with a finger. Again she didn't seem to like that too much, not unlike a lot of women. (Perhaps I will try to explain that at another time.) 

Whilst all of this was taking place I kept an eye on Paul. He was half lying behind her with her head resting close to his stomach and his hands lightly on her breasts. When I caught his eye he smiled and nodded which I took as an indication that all was well. 

Knowing where to avoid, I started to work on her again, this time with my tongue as well as my hands and her response was to purr with pleasure. Not surprisingly she tasted of pussy flavoured baby oil, not unpleasantly so, as I licked at the inner folds and around the stem of her clit. I used my hands to caress her inner thighs with my thumbs stretching down to graze the soft flesh of her bottom and to continue the stimulation of her outer lips. She especially seemed to like it when my tongue passed over her little pee hole. 

As I increased the pressure and pace of my licking, her hips began to rise from the bed and we found a mutual rhythm, almost as if we were fucking. Hoping to take her over the edge, I placed my whole mouth over the area of her clit and, without touching the tip with my tongue, I sucked in pulses so that her clit was popping in and out of its sheath. It worked for her and, after the long build-up, her climax came quickly with strong convulsions, trembling thighs and a lot of gasping. 

Before her orgasm could resolve, I told Paul to come and take my place between her legs and he didn't need a second invite. He was quickly out of his briefs and a nicely sized cock was standing to attention. I had only the merest moment to get a feel of it as he positioned it against her slit and, with one quick thrust, went all the way into her. It was the right thing to do -- this was no time for smoochy, squelchy, wiggling around. 

As for Deborah, I don't think she really knew what was happening until he started the fucking. I took over Paul's position on the bed, holding her and sensing the power of her arousal. I don't know if she actually came a second time or if it was one long continuation but by the time he was done, which wasn't long, I would say it was the latter and I think she would too. 

As things started to calm down, I had the sense that it would be best to leave them to themselves and their private moments so I went to the bathroom to dry-off before wandering out onto the balcony. I thought to myself that I had given Deborah what she had asked for and hopefully a little more. For me, I had used her body, taken every pleasure from her sensuous flesh, felt all of the exhilaration that came from evoking her lust and desire, then giving her the final release. And if you have ever held a woman whilst she is being fucked, then you will know how great a turn-on that can be. For all of that, it had been a very one-sided affair and an ego trip was of no use in quelling my own state of arousal. I would have loved to be taken, just as Deborah had been but it wasn't to be -- it kind of goes with the territory when you are in my shoes (which is not to say that I don't have my moments). 




Tales of a Mature Prostitute Ch. 05



In writing this short account of Paul and Deborah, I can't help but reflect that I could have managed things differently. Perhaps I should have given Deborah more opportunity and encouragement to explore my body as I had explored hers. Perhaps I should have stayed with them for longer and things would have developed in another direction. But whatever, it was as it was and, before I left, the two of them were very gracious in expressing their gratitude. Perhaps it was enough of a first time for Deborah and I think they will always remember me, just as I remember them.



Tales of a Mature Prostitute Ch. 06



Hello, and the first thing to say is a big thank you to those readers who contacted me with such great feedback. I responded personally to almost all of you but several of you decided to stay anonymous so my thanks here is especially aimed at you. 

I have the sense that these stories are becoming more like blog posts and I notice that there are lots of blogs around that are authored by sex workers. Be that as it may, rather than get involved with blogging, I will try to keep writing here at Literotica for as long as the positive response continues. 

In whatever business, they say it takes around two years to become established. In some ways that has been my experience, not so much in building up a client base (that happened sooner than I expected) as in having a network of contacts in the same line of work. For a while, a number of them have been getting together, perhaps once a month, and I have now joined the group. The topics of conversation will usually include police activity, nosey neighbours and troublesome clients. Since we all operate privately and discretely, none of us have had problems with the police, who concentrate on the downtown street girls and those involved in drug dealing, but you never know what might happen in the future. Through these get-togethers, I have met two ladies with whom I have had the opportunity to do double acts, that is to say, both of us entertaining one client. But the one thing which is never discussed is money, even though we would all like to know who is charging what and how much are they making; it is one of those elephants in the room. 

I have also met the lady who runs the main escort agency in the area; I'll call her Laura, an ex-escort herself. She is roughly my age and fully understands the kind of things I offer. The other "girls" (I put that in quotes because the light would have to be pretty dim before I was taken for a girl), who have worked for her say she is very careful about vetting clients and that has been my experience as well. She has put several my way when I have been free, all of them outcalls to 4 or 5 star hotels and all of them to upmarket guys. Let me tell you about the most recent. 

He'd told Laura that he would like me to wear fishnets, heels and a short skirt, so she had to explain to him that, since he was staying in a resort hotel, I would look far too conspicuous on a Thursday afternoon but I would be happy to change into something when I got to his room. He'd said in that case, just fishnets and heels, and nothing else. 

That Thursday was a beautiful sunny day but not too hot and humid and, as I wandered through the grounds of the hotel looking for his room in one of the many accommodation blocks, I would have much preferred to join the other guests by the pool. But business is business. 

He greeted me wearing one of the hotel's white cotton bath robes, invited me in and offered me a drink. He was a 30-something Englishman, much younger than my usual clients, quite good looking, well-spoken and here on the coast on business. Best of all, he was very straightforward in asking for what he wanted. Just as Laura had briefed me, he said he'd been away from home for a week and was feeling lonely. Rather than jerk-off on his own, he thought it would be good to get some help and wanted a session with someone like me because older women were more understanding. He didn't want straight sex because he didn't want to be unfaithful to his wife. (Everybody has their own sense of what constitutes infidelity though it does seem to oscillate with context.) 

I think he would have liked to talk for a while but I reminded him that time was passing and perhaps he would like me to get changed. He didn't have any objections so I grabbed my bag and headed for the bathroom. I noticed that the shower was wet so he had recently used it which is usually a good sign. When I re-appeared he was on the bed, lying back against the headboard, naked. The conversation went something like this:

Client: Wow, I've never seen someone small and dark in the nude before. My wife is tall and blond.

Me: Perhaps it's nice to have a change.

C: Yes, and she never wears fishnets for me.

Me: What a shame. I wonder why not.

C: She says that I ought to take her as she is.

Me: Oh, well ...

C: Would you turn around for me?

Me: Yes, of course.

C: Would you mind bending over?

Me: You mean like this.

C: Wow, you are amazing. My wife would never do that. Do you like my dick?

Me: It's getting big – nice!

C: My wife likes it too.

And so it went on: how she never used oil on his cock; how she would give up if he took more than a few minutes; how she didn't like him cumming on her tits ... 

As well as guilt, another elephant in the room that I often encounter is insecurity, specifically (surprise, surprise) in regard to penis size. Many of my clients are getting on in years and they have difficulties with erections – that is why they come to me, as I have explained in earlier stories. For them, I can well understand and sympathize with their feelings of frustration and I go out of my way to show them that it isn't the end of the world. 

With clients who don't have erection problems and those that respond well to Viagra, I can't think of a single one who hasn't asked me, in one way or another, whether or not their cock was big enough. Even that Englishman, who had a good 17 or 18 centimetres (7 inches), asked the question, though with him I think it was more in the manner of a boast. 

Now, I fully realise that my clients know that I have had a good many men through my hands (in a manner of speaking) and therefore a lot of experience on which to base judgements. Also, I understand that, for many men, cock size relates to their perceived sense of masculinity and so, of course, I always find something complimentary to tell them about their equipment. If I feel that I have some rapport with the client, I will add that average works fine because it's who the cock is attached to that makes the difference. I will add here for you, dear reader, that, if I'd had that Englishman inside me, I'd have been angling my hips such that he had limited penetration, otherwise he would have "bottomed out" which is really not a good feeling. 

So, if you wish to know why, for most women, bigger is not better, then get to know about female anatomy – it's all on the internet if you look in the right places. 

I've written about money, guilt and insecurity and now for the matter of premature aging. It has often seemed to me that some people adapt the way they behave in ways that they somehow believe are appropriate for their age. I think it is often the case with my older clients and I have always felt like challenging them about it because they seem to be making themselves age unnecessarily. Then, quite recently, I found an article about some research that was done in 1979 by a psychologist called Ellen Langer. Briefly, she discovered that, by taking older men back in time in their minds, it had a positive effect on both their psychology and physiology. This simple concept is something I've been using with some of my clients and I have the sense that there are some positive results, though the only hard evidence is what I feel in their cocks. The best way to explain is to give you an example about a certain client and what he told me about his encounter with the lady from the accounts department, as well as I can recall it. 

Me (fondling client's cock): Would you like to tell me about the best sex you ever had?

Client: There's been a few that would qualify.

Me: What about when you were much younger?

C: Well, there was a woman in the accounts department where I worked. I'll always remember her.

Me: Tell me about her – what was her name?

C: Elizabeth - everyone called her Liz. She was 40 something and I was around 25. She was divorced.

Me: What did she look like?

C: She was quite dark skinned and she had a lovely face. She was always smartly dressed but a bit blousy as well, and she had a bit of a reputation. She had thick dark hair and it was always pinned back in a kind of bun. She was very curvy. I suppose she was a bit overweight but in a sexy kind of way. 

Me: You mean she had big tits?

C: Very, and quite a big bum as well.

Me: I get the picture. So what happened?

C: I always had the idea that she might like me but I didn't have much chance to find out for sure. And, anyway, I think I wasn't the only one who she had a fancy for. Then someone from the office was leaving and there was a farewell party after work. Somehow, I found myself talking to her and she was getting quite flirty. I guess she'd had a few drinks by then. Eventually I asked her if she'd like to go somewhere else after the party and she said she lived close-by and we could go back to her place. 

Me: I think she'd lined you up. And it was an offer you couldn't refuse, right?

C: I couldn't believe my luck.

Me: So you went back to her place ..

C: We'd hardly got through the door when she put her arms around my neck and we were kissing. 

Me: Wonderful! She was hot for you.

C: Yes, and me for her. Her hands started wandering and I followed suit. 

Me: What did she feel like?

C: Firm, much more than I expected. But her tits were soft.

Me: Go on, I'm enjoying this, tell me more ...

C: She said we should go to the bedroom and I followed her up the stairs. I couldn't keep my eyes of her backside and I'm sure she knew because she was really swivelling her hips. 

Me: Naughty lady - she would be teasing you, for sure.

C (his cock getting noticeably harder): In the bedroom she said, "Let's get undressed." She dropped her skirt and took off her blouse in a flash, and I was still trying to get my shirt unbuttoned so whilst I was doing that she started getting my pants off. 

Me: So you ended up naked and she was in her underwear.

C: Exactly. I can see her now, standing there in a white bra and panties with hold-up stockings. 

Me: And you with your cock standing up. I would have loved to be a fly on the wall.

C: Yes, it was standing to attention. And when we got on the bed and it was pressing into her thigh, I thought I'd burst. There was pre-cum everywhere. 

Me: Your big cock and her stockinged thigh ...

C: Yes, and on the outside of her panties, against her pussy. I was really on the edge. The only other time I'd felt like that was the first time I did it, with a girl I used to go to school with. 

Me: So what did you do? 

C: I think she knew that I wasn't going to last long. She got her panties off and said, "Come on, let's do it now." 

Me: Experience counts. Did you get a look at what she'd got between her legs?

C: Yes. She had a bush of thick black hair. And when she opened her legs I could see her dark flaps. It looked amazing. I got on top her and I went straight in at the first attempt. 

Me: The first thrust is always the best. What did it feel like inside her?

C (now with a very hard cock): Hot and wet, and kind of silky as well. I asked if I should pull out when I was going to shoot and she said it was OK to stay inside because she was taking the pill. 

Me: So this big cock of yours was balls deep in a hot and wet, hairy pussy. How long did you last?

C: It was the first time I'd done it with an older woman and I was so turned on by everything about her that I was cumming with just a few pokes. It just kept gushing out of me. 

Me: Do you want me to make it gush out of you now?

C: Oh God, yes please. 

I have given this particular client a good number of handjobs with various kinds of other stimulation so I know him quite well. Prior to the story session, I always had to grip the base of his cock with one hand, to create a pseudo erection, and stroke with the other hand. After telling me his story, he was hard enough not to need much gripping and I could mostly use both hands to stroke. He seemed to be turned-on more by his own real-life experience than by watching porn – how interesting. He left in good spirits. 

If you are wondering, in subsequent sessions he has also told me about rounds two and three with Liz from accounts and she sounds like she was every young man's dream. Each time he managed to hold a decent hard-on.

(Before I move off the topic, a question to readers who have more experience than I do in these things – Is it not the case that every company that ever existed has its own equivalent of "Liz from accounts?") 

My fifth elephant in the room is that old friend, lust. Let me take you back to Laura, the lady who runs the escort agency. I first met her in her office and it was lust at first sight, and from the way she looked at me, I think there was a reciprocation. She was very much in the mature Jane Fonda mould, though softer in her manner, and to me, much more attractive.

I've found that with bi-sexual women, it works this way: there is an attraction to another woman that is based on nothing more than a desire for sex with her. When it comes to a man, things are much more complicated and even contradictory, at least for me, but I won't try to explain that now. 

Back to the meeting with Laura. Despite the sexual tension, we kept things business like and I gave her a resume of what I had to offer, all of which you can discover in my earlier submissions to Literotica. She was surprised and fascinated that there was such demand for my services from older men and she felt there was an opportunity to exploit the market further. But things got really interesting when I told her about the couple calls I had done and what had happened with the various wives. At that point the elephant was straining at its seams and it finally burst as I was leaving when she asked me very straightforwardly if I thought the two of us would end up in bed together. I said that I hoped so, kissed her cheek and she said she would call me. 

I didn't have to wait long. She called me to ask if I was free and could she come over just after my final client had left and I was about to take a shower to get rid of the semen and oil that was all over my boobs. I asked her to give me an hour and she was at my door on the dot of 9.00pm. She left at1.00am.

During those four hours, I discovered that she was a great kisser, that she could almost cum from having her nipples stimulated (quite harshly), that she had a small heart-shaped tattoo on her left bum cheek, that with enough G-spot stimulation she could produce a series of squirts (just a little each time, about the same as an average man, not the kind of fountain that you see in porn) accompanied by some very deep groans and seriously strong body convulsions, and that she was very experienced in exploring the female body. 

As for what she learned about me, you would have to ask her, except that she discovered I was very partial to a nice spanking accompanied by lots of stroking and fondling. 

I also found out that she had a live-in man friend, twenty years her junior, of Italian extraction, by the name of Fredrico but she called him Rick. He was quite happy for her to have girlfriends, perhaps especially because it sometimes would lead to a ménage à trois. That is just how it was to work out with me and, having told you that, it would be most unfair not to tell you more. 

(In case you are wondering why I would agree to sex with a man I'd never met, in my personal life, the answer is that if he had passed muster for Laura, he would very likely pass muster for me too.) 

Before I get to it, let me say that Laura's philosophy was very rare among women. She told me that, with so much lovely pussy in the world, it would be most selfish to expect Rick to confine himself to just hers, and, besides that, if she was free to get her share, why shouldn't he have the same option. I endorse her view 100%. 

I first met Rick one Sunday evening at Laura's place, a well-appointed property sitting on the hill overlooking the South beach, and ample evidence of the money that can be made from sex work. I had expected him to have the sophisticated, refined look of a successful, middle-aged businessman, but not at all; he looked as if he would have been totally at home hanging out with the surfers down on the beach below, not for lack of grooming but on account of the suntan and especially the full head of wavy, long, blond hair. If you ignored the slightly greying temples and the laughter lines around his eyes, he could have passed for 30-something rather than a man of 50, the perfect boy toy for Laura. 

For all the many times I've sat on a patio drinking wine with another woman and a man or two, with the absolute certainty of what was to come, I still find it an intoxicating experience, especially when it is a first time, and it was just that with Laura and Rick. His conversation was almost irrelevant; it was impossible to look at him without thinking it was only a matter of time before he would be in me. And then Laura: I wondered what part she would play. 

Since I was the guest, it was for them to take the initiative. It began when Rick asked me to dance, which was more of a smooch than a dance, and my first real sense of him, his smell, his feel, his movement, his power – all very male, very masculine. 

Then Laura was behind me, hands on my hips, kisses on my neck, hands easing my dress off my shoulders, down to my waist. No bra and my naked flesh was free for four hands to roam and feel and stroke and squeeze. Then my dress on the floor and only panties, wet from arousal. I felt naked breasts against my back, so sensual, and Laura's murmur – "Now you're ours. You'll enjoy it." Best of all, there was the unmistakable feeling of Rick's desire: his erection pressed against my tummy. 

Through the sliding doors to the orange half-light of a bedroom, Laura ushered me in with a slap on my bottom – a reminder of a few days earlier. Onto the bed, she stripped my panties away, laughed at the wetness and grabbed my pussy in the palm of her hand so that I could hump against it. 

A naked Rick joined us and I had eyes for one thing only – a nicely curved, thick and very hard looking cock, the head swollen and angry. No foreplay necessary – I just wanted it inside me and I said exactly that. (If this doesn't sound like how it is supposed to be, I can only respond that I am how I am. With a man, 20 minutes of conventional step-by-step foreplay has its place but often it bores me to sleep. Generally, I arouse myself with anticipation in my head and that's where the foreplay happens. I would add that neither do I need to be slam-fucked for 20 minutes – that is tedious and very likely to end up being painful.) 

With a thick pillow placed under my hips and my thighs wide apart, Laura ran her fingers through all the exposed crevices while Rick, sitting back on his heels, edged closer and closer. The final seconds of anticipation brought a new flow of wetness from somewhere inside me and I felt it trickle down against my bum. And then the first contact as that cock took a taste of me, Rick working its head smoothly against my clit to join Laura's fingers. 

From there, Laura orchestrated events. She told him that she thought I would cum quickly (she was right) so to just push in a little way. I felt that momentary twinge as the big head went through the ring of muscle and he held it there as best he could, with her working my clit. Bumping and grinding my hips, it was more me that was fucking him than the other way around until Laura finally told him to give it to me. Those first few deep thrusts, powerful and determined, opening me up to the hilt, took me over the edge, and he continued with them through all of my release. It was so good it was almost unbearable. 

His cock came out in almost the same state that it had gone in: thick and stiff, but very slick and slippery. Laura went to it immediately, wrapped her mouth briefly around it, said it tasted of me and then, straddling one of my legs, took up a position on all fours with her head just above my tummy. She looked at me with raised eyebrows and a cheeky grin which turned into a grimace then a pout as Rick penetrated her. He started slowly and gradually stepped up the pace, and she held my gaze for a while but it couldn't last. Her moans became louder and more frequent, and then her eyes were screwed tightly shut as her orgasm drew close. Her head dropped onto my tummy and her hands grasped at my waist as she started to cum with Rick pounding her hard and fast. His hair was matted to his forehead with sweat and his body glistened almost like bronze in the orange light. As his thrusts turned into jabbing jerks, I watched that look of ecstatic agony develop on his face and then the groans as he filled up her pussy. It ended with three hot bodies in a heap with Rick's semen oozing out of Laura onto my thigh.




Tales of a Mature Prostitute Ch. 06



The upkeep of a swimming pool is time consuming and costly but, at that point on a very warm sub-tropical evening, worth every second and every cent. It wasn't the end of the evening, just a refreshment break which turned into some pool games. It is amazing how sensations are different with the buoyancy of the water. I wonder what it is like in space – does anyone know of a female astronaut who writes for Literotica? 

I've reviewed this story several times and have decided that the flow is not too great, what with all my bracketed asides and other bits and bobs. Nevertheless, I'm leaving it as is because real sex is like that. It seldom flows as smoothly as most prose would suggest but it usually comes to a good conclusion despite the distractions. 

Hope you found it worth reading, 

until next time - Gabby.