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.