I decided not to name this guy myself like I often did for male escorts because he was not officially working at the time, but eventually he chose the working name of Tyson for himself.
The first booking was easy to make, as I already knew he was wanting to be an escort as he had reached out to me. We had a few texts then I asked him to call me. A price was discussed which we were both happy with. I had no idea what he looked like but I could tell from his accent that he was African American.
He told me he was in his thirties (so more than a few decades younger than I) and we superficially discussed his background etcetera and made time to meet. As he was not working officially yet and did not have premises, I arranged for him to come to my unflashy but well-appointed working rooms.
When he walked in, I was very happy with his appearance. He is a good looking man. He also smells great. I asked if he would like me to run the shower and it was when I came back from there that I first saw his cock. It was not hard, yet it was already enormous – definitely an XL condom for him.
It reminded me of an incident many years in my past when I had been a timid housewife and office worker and curiosity had gotten the better of me. I had overheard someone making a reference in passing to a famous man with an 18 inch long penis which they had seen online - I could not believe that and had to see with my own eyes. Yahoo search was in its early days as Google was not yet widely used and I had entered “penis 18 inches” into the search bar of my work computer - I did not own a personal laptop or other device at home yet. I did not know about deleting history or even closing tabs.
Later in the day, my boss and several other staff members came over to help me investigate setting up an online video call with new phone software called Skype. My boss entered “phone call Skype” into the search bar, and while he hesitated to check the spelling of Skype in the newspaper article which he had saved, all the previous searches which began with the letter p like “penis 18 inches” appeared for us all to see, There was another lady in the office who shared my computer who was younger, sexier and far more likely to have gone searching for penises online, at least that is what I hoped they thought.
"Interracial couple" by Michael Dowson
Anyway, Tyson unzipped my dress and we chatted while I removed my shoes and undid my stockings from the suspenders. Then I waited while he showered.
The huge cock could be a deal breaker for some ladies if he was a boring one-speed kind of guy, as most ladies find fast pounding quite painful. Fortunately he was not that guy, instead he was a great lover. I won’t go into details as that would be unsavoury at this point other than to say that we could have easily gone over the hour with our roll in the hay and he let me cum multiple times.
Size of course doesn’t matter but his cock was by far the largest I have ever had out of the thousands of cocks I have come into contact with over the years, however his size would have been irrelevant if it wasn’t for the fact he knows how to please a lady. Holding his cock made my hands look tiny. I couldn’t take all of it in to give him a blow job, but I did my very best.
Tyson and I got on really well and his personality was excellent but of course it was his skills in the sack that were memorable. The fact that he was so much younger than I made no difference as he told me he found mature ladies super hot.
Also, meeting with him sight unseen did not feel like a risk because I could tell from our phone conversation that his personality and attitude appealed to me and this is probably a more important factor to ladies my age than appearance since it was purely a bedroom booking rather than an outing somewhere. Even if it was an outing booking, I would be really happy to be seen out with him: he’s a great looking man and anyone who saw us and wondered could think whatever they want.
I concluded that I would definitely see him again and would highly recommend him to any ladies that got in touch with me if I thought he was the right one for them.
Like Raewyn. She was the sister of a previous lady I had matched with a client from my group of male escorts in my newly formed business Handsome Man Agency. Raewyn’s sister was a born romantic with specific needs and desires that were unable to ever be taken care of by her loving but normal husband whom she was happily married to. She had thought of having an affair but men who frequented the dating apps were even less capable of understanding the special way her sexual fantasies ran.
However, one of my Handsome Men, who went by the name of Chad, was briefed by me about exactly what she needed him to do - we even role-played a little script I wrote for him in my office which was gently adjusted in a few places as we worked through it. He dressed according to my suggestions and I set up my working premises exactly according to what Raewyn’s sister had required.
"Naomi " by Fabian Perez
Raewyn’s sister and Chad became a regular thing - all purely transactional of course as she intended to remain entirely faithful to her husband and would never dream of having an affair. Raewyn had enquired one day about the changes her sister had made in her life which appeared to be a result of an improvement in her self-esteem. That is how Raewyn came to contact me, in fact, this was how all of my lady clients came to find me.
Raewyn opened up to me knowing I was completely non-judgmental, about a long-held fantasy of hers. Because of the size of her bosom, Raewyn was a walking bodice ripper. She could not help but put a twinkle in every straight man’s eye. But she wanted a bodice-ripping romance of her own design and on her own terms and Tyson would fit the bill perfectly.
Tyson was perfectly suited to Sharon’s desires too. And Moira’s. Jill was also taken by his smooth American accent and southern charm. So was Kath. The way Tyson operated was also intriguing for Mandy. The list went on. Ladies were finding out about him through word of mouth and wanting him for themselves. Tyson was on fire.
“I feel like a Freud," he texted.
“Don’t you mean fraud?” I replied.
“No, Freud. Sigmund Freud - the guy that did all the nude paintings”.
“Oh you mean, Lucien Freud. The grandson of Sigmund, the artist. Can you elaborate? Do you mean you don’t like looking at ladies’ bodies???”
“No, I LOVE NAKED BODIES. I just feel so spoiled with all these ladies wanting to get UNDRESSED for me. I have always had to work so hard for it. Now I'm getting paid”.
“First world problems, but I hear you”. I wrote. “Let’s meet for lunch and talk it through.”
When Tyson strutted through the Sizzle and Steam cafe, the head of every mature lady looked his way. He had a swagger about him but there was not one thing I could put my finger on that defined this. He was not ostentatious in any way, he just looked comfortable, with a self-respect yet also almost a shyness or humility that ladies found attractive. He was the kind of guy who opened doors, pulled out chairs for people and removed his hat when he was inside, not to make a statement but as a matter of course, just because being considerate was how he had been brought up.
I think well-hung men already have a golden key to life. So many clients who came to see me as Amber, a MILF escort, who were of perfectly normal-sized to big girth and length are convinced they have micro penises. Aside from the men who get off on small penis humiliation, size seems to be an ongoing anxiety issue that many men suffer from. It can really fuck some men up and cause all sorts of performance issues and one wonders if it spills over into other areas of their lives too, causing a bitterness in general relations, such as in business, or even towards women in general, due to what they feel is an insurmountable inadequacy. Small dick energy is the other side of the big dick energy coin, an insecurity that it is sensed has plagued their whole life. Hence the one thing that gives men with big dicks the self-assurance that is impossible to define but can be recognised as Big Dick Energy. Actually, I have met even less well-endowed men who have a similar composure, so maybe it is not related to penis-size. But it is definitely a thing.
"Penis contest" (c.1855) from the series "Shunkyo karami-dako (Spring Games: Grappling Octopus)" by Utagawa Kunisada II
Tyson poured his heart out to me and we tried to come up with a solution. As an owner of an escort agency in the adult industry, my responsibility was not just to take care of my clients, but also the staff, although strictly speaking they were not staff but independent contractors. This involved making sure that none of the clients overstepped boundaries and fully understood that the encounters that they were about to have with perfect men (for them) were not real and they can not expect anyone to fall in love, this was simply not part of the arrangement. (Although I was not trying to play God, they were consenting adults and love may occur - it was just best to be realistic and keep it within the time paid for.) In other words, I sometimes had to make clear for the safety, including emotional safety, of all involved that the time they spent together was a fantasy - usually for both of them. Yes, both of them. After all, what man in his right mind would not like to be paid to pleasure a lady?
This was the issue for Tyson - his needs were being met, including his financial needs - and he was feeling that he had won the lottery, but somehow the Inland Revenue Department was going to come along and snatch up 90% of it from him. However, he was a permanent resident of New Zealand, where sex work has been decriminalised. He had set up a company - New Zealand is one of the easiest countries in the world to do this, requiring about $160 and the filling out of an online form and setting up a business bank account, into which all his payments were deposited, and from which he was covering expenses including tax and his own salary. Everything he was doing was above board and correct. It was almost too easy.
Did he need a break? Was I sending too many ladies his way? Was he feeling exploited? We covered all of these issues but it was none of the above.
It turns out that Tyson had a fantasy of his own and he wanted to go back to seeing a mature lady escort, as per our original booking. He was pleasuring lots of bosses, babes and bitches, sure, but he wanted to be used and exploited by his very own boss lady, me. So the scene was set.
“Come to my office at 4pm”, I told him.
“I want you to come ready to convince me why I should still hire you.”
4pm sharp and there was a knock on my unlocked door.
“Come in,” I said coolly.
“Did you bring your resume?” I enquired.
“Yes, ma’am!” he replied as he unzipped his fly.
Out he flopped his perfect cock, soon to measure a perfect 18 inches.
“I have a few tasks for you” I said, as I sat behind my desk, leaning back in my executive chair and putting one of my stiletto heels up on the desk and beckoning him over to me. He soon noticed that I was sans panties.
How I loved being an escort again and working with the fantasies of my clients. I realised it was a need of mine that was not being met and things were about to change. Amber is back.
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