"French" Postcard from the 1930s depicting the escapades of a red-haired whore by an unidentified (probably Gernan) artist
Amber O'Hara
04/08/2026
8 min
0

Confessions Of A Happy MILF Hooker: Twice As Nice

04/08/2026
8 min
0

Back in the 1980s, it was fun doing sex work with my best friend, Roxanne (real name Gabby), who had long red hair like me and as this seemed to make it difficult for some people to tell us apart, we capitalised by charging more than double what we would charge as singles for a “twins” or “sisters” fantasy, which turned out to be a huge success.


Besides having 9-5 day jobs in offices during the week, on Fridays and Saturday nights we also sang backing vocals for a band, who aspired to make the big time any day now.  Our band did not know that on Mondays and Wednesdays we moonlighted as sex workers at an exclusive (or so our boss Michael liked to think) gentlemen’s club known as The Lounge and it was one thing Roxanne and I were terrified of anyone finding out about us.


One night our band got an offer to audition as one of the support acts for a famous international group which, if successful, would be an opportunity to tour the country and would be a major step towards the Big Time.  It was afterwards at The Sebel Townhouse, an upmarket boutique hotel where the secrets of the music industry remain within its walls, that the lives of Roxanne and I were changed forever.  A tall, glamorous lady called Leigh introduced herself to us.


We had heard of Leigh, everyone had.  Her name was on the door list of all the posh after parties and she seemed to be connected with the who’s who of the whole world.   I heard she had been a casting agent for the film industry, or the wife of a music executive, or a model and sometimes people said she had even been a dominatrix in a high class dungeon, or maybe she had been all of the above.  We had seen her on TV and in magazines but we never thought we would see her in person, let alone meet her.  Not only did she introduce herself to us and seem to know our names, but she invited us to her house for lunch the next day.


High Class Hooker, 2022, Mixed Media by Simon Fleeman

High Class Hooker, 2022, Mixed Media by Simon Fleeman


Gabby and I were beside ourselves with excitement.  She lived semi-rurally and her driver collected us from the carpark and took us up to the house.  We had never seen such opulence.  She made us feel very welcome and already seemed to know all about us, including that we worked at The Lounge, although she took pains to reassure us that no one else knew that secret and neither would they know.


The night before at the Sebel, we had found out that our band did not get the touring support act job, but we ended up having an ongoing relationship of sorts with Leigh, which was lucky as our boss at The Lounge, Michael, was sick of us “mucking him around.”  We would be half an hour late - we were after all battling traffic to get to the Lounge an hour after our office jobs finished - and he would have 50 clients waiting for our “twins” bookings, most of them were waiting on the off chance we had a cancellation of a pre-booked client - that never happened.  Our original regulars were complaining that they could not see us and some were leaving in disgust.


At first Leigh was arranging “accidental meetings” for us with erudite, older gentlemen who were visiting the country for writers festivals and that kind of thing.  I do not know what she was charging, but we were being paid handsomely, about six times what we were earning for the whole night at The Lounge.


Our new working names were Roxie and Gabby which we used interchangeably, rather than Roxie and Roxanne (our two sex work names) and Gabe and Gabby (our real life names).  It just simplified matters so that if we bumped into our clients elsewhere or anyone who did not know we were sex workers, we could use either of those names as clients always seemed to want to say hello.  Respecting the privacy of sex workers was not considered important like it is nowadays.


We would meet Leigh’s clients, who were usually friends of hers, when they were visiting Australia.  It was always “accidental.”


For example, the first time we did it, we two girls attended a book signing or something then hung around afterwards to meet the author.  Nine times out of ten we would be invited out for a drink or a bite to eat with the author and mysteriously find ourselves back at their hotel room.  Actually it was ten times out of ten that this happened.

Hooker Painting by My Head CinemaHooker Painting by My Head Cinema


Our first client assumed that we were fans or groupies of his as we never discussed money and Leigh fixed us up the next day.  We never knew how much it would be but every time we were pleasantly surprised.  I did not know at the time where Leigh got the money from, but it turns out it was invoiced to the promoter as entertainment expenses and never questioned.  I guess these people had expensive tastes in wine and never expected anything to be itemised.  Leigh seemed to know every promoter and agent across all the music, film, literary, art and beauty industries.


One of the next clients we met was Edward.  We attended an exhibition opening with the who’s who, except Gabby and I did not know who anyone actually was, so all the lording over was wasted on us.  Leigh was there nibbling on hors d'œuvre and she pointed us in the direction of the man whose every word we needed to hang on to.  He seemed to be quite important but we knew that he had noticed us and there was some intrigue as he kept glancing at us, and we would smile and giggle from the edge of the circle where he was holding court.


When we got him back in the room, we realised he had a number of fetishes, threesomes being one of the more familiar of them.  He also liked long hair.  He wanted to sniff it, stroke it, this alone made his cock hard.  The two of us naked, leaning over him and whipping him with our hair was almost too much for him.


He also liked pubic hair.  His complaint was that we were not hairy enough, he wanted to rub his face into pubic hair that grew down our inner thighs, almost to our knees.  (Damn you, Veet Hair Removal for the summer swimming season!)  Gabby was due for a shave so had some shave-ready stubble in her armpits which delighted him.  Alas, as natural redheads, aside from the inner thigh depilatory work, neither of us were hairy enough to need to shave our legs.  Yes, there was hair on our legs, but it was thin, pale, wispy and far between, not exciting enough for Edward.


"French" Postcard from the 1930s depicting the escapades of a red-haired whore by an unidentified (probably Gernan) artist (In Premium you can find the complete postcard set!)


Edward liked to lie on the floor and have us both stand naked with our feet on either side of his body and look up at us.  We spent about 30 mins just walking around and over him in our sky-high heels while he looked up at our vaginas and arseholes and masturbated.  He wanted us to do this on the bed initially but we both had sharp stilettos which would have damaged the mattress and our heels were so high (8 inches), they needed somewhere solid to balance on.


I knew it was coming and he eventually wanted us to stand on his body and put all our weight on him.  This is called trampling and it is a form of bondage, discipline, sadism and masochism, which both of us needed confidence and training with.  Also, standing on a human body is as stable as standing on a mattress.  I eventually mastered this for a moment and this was enough to send Edward into the celestial reaches of ecstasy, as he came with a thrashing about and I had to quickly step off him lest I fall.


Another client, John, we met through Leigh was at a small council swearing in ceremony.  Present were the newly elected mayor and councillors and a few close friends and family.  I have always found politicians to be boring outside of the bedroom but especially kinky inside it.  The one that we went home with was a divorced man who lived in a large inner city apartment.  He told us he liked two ladies, especially identical ones.


He had a collection of disposable diapers in adult sizes, all of them were in pale blue with bands decorated with teddies and rattles.  But we did not know this until we all got out of the spa.  He lay himself on the bed and asked us to open his bedside cabinet.  Expecting a collection of sex toys, we were surprised to see a pile of nappies, a rattle and a bottle of baby powder.  He asked for the rattle which he shook as he made baby noises.


“Mummy, new nappy,” he cooed.  “Call me good boy.”


We took the baby powder and sprinkled it all over him.


“Good boy!” I said.“Good boy!” Gabby said.


He snapped out of character to instruct us,


“Say it in unison, it’s my twin fetish.”“Good boy!” we said together.


We gently rubbed the powder which we had sprinkled over him and together we lifted his bum to put the nappy under him.  I heard Gabby start to say “who’s a good boy,” so I joined in to say it at the same time.


By the time we fastened the bits of plastic on both sides of the nappy, he had splurted out a big load of come into the nappy.


“Baby boy need new nappy” he said.  So we started again.


This time we combined our two personas and began to sing to him, in unison, in a sexy drawl, like Marilyn Monroe singing to JFK.  Our John was, after all, also a politician.


“Row, row, row your boat,”  We stood there naked with our heels on and got into our back up vocal dancing positions.“Gently down the stream” we sang steamily.


“Wow!” he said and propped himself up on his elbow.  “You two are something else.”


“Why thank you” we replied in unison.


“I want to see you more often. Can you do twice weekly?”


“Of course,” we said together.

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