I had got myself into a mess with a loan shark and was behind on payments.  His thugs had dragged me before "The Man" as he liked to be called.  I had heard lots of rumors about him.  He ran drugs mules as well as illegal gambling and used the loan shark money to launder his money.  I also heard that he had used lots of the women that owed money as prostitutes, even the married ones.  For a male like me, the chances were that I was in for a broken leg or worse.


He was sat behind his desk smoking a cigar and trying to hide his fat body.  "A good looking lad like you should be able to make good money," he told me and then added that he had a job I could help with.  I had horrible visions of being a getaway driver or doing a bank robbery.  Then he told me that he wanted me to be a gigolo and had just the right client for me.  I couldn't believe that he wanted me to service some of his clients.  It definitely wasn't a request when he told me that on Wednesday night to be in my best clothes as he had a client for me.  I told him I would rather take a broken leg than have some greasy old man shoving his cock up my arse.  He laughed and told me that it wasn't an old man it was an old woman.


It didn't sound that much better but what options did I have.  At a quarter to eight one of his thugs came and collected me and to my surprise there was already another well dressed man in the car.  We were dropped off at a very plush hotel room and told to wait until the client arrived.


The other man was probably in his late thirties and I was in my mid twenties,  As we sat waiting he told me that he had been given to many clients and still owed "The Man" loads of money.  I asked what were we expected to do and he answered anything the ladies wanted.  At that point the door opened and in walked this woman who I judged was probably in her early fifties.  She was dressed up to the nines and had far to much makeup on and looked like someones granny.   She was also more than a little on the plump side.


"Well what do we have hear, "she retorted.  She recognized Rory as he had been to her before, but had me do a twirl like a young girl showing off her new dress, but was instead sizing me up.  "Well hurry up and get undressed then," she snapped at us.  Rory was tearing his clothes off and I followed his lead.  By the time we were naked she had kicked her shoes off and was sprawled on the bed.  "Well undress me then," she snapped and Rory and I were soon relieving her of her clothes.


It seemed odd undressing a woman of that age and as each piece came off the more I could see she was more than plump, she was fat and had several rolls of fat around her stomach and gravity hadn't been kind to her either as everything drooped.  "You lick my fanny," she ordered Rory, "and you bring that to me," she was talking to me about my cock which was still soft.  She told me she didn't normally do this as she licked and sucked the end of my circumcised cock and Rory started sucking on her pussy.


She had been sucking me for some while and I still wasn't getting hard.  She took my cock out of her mouth and licked her own fingers and then as her other hand put my cock back in her mouth a finger on her other hand found my anus and plowed right in.  It was a complete shock.  Nobody had ever touched my arse hole let alone shove a fat stubby finger up it.  It hurt and yet felt good at the same time.  Then I could feel her finger moving and exploring my insides.  Then suddenly I was coming and filling her mouth with cum.  I found myself jerking my hips and my cock was now free from her mouth and splashing cum on her face.


She was less than pleased and was shouting at the two of us to clean her up.  I was looking for a tissue or towel, but Rory was up and licking the cum from her face and hair.  She grabbed my head by my hair and forced me face down between her large floppy tits and insisted that I lick my own cum up of her tits.  I didn't have much option and reluctantly licked my own cum of her tits and then when she was satisfied that I had got it all I was instructed that if I couldn't control myself I had better lick her fanny.


My face was then thrust into the the hairiest fanny I had ever seen.  I could hear her moans and groans as I licked her fanny.  Then I was being pushed out the way and she had Rory get between her legs and fuck her.  I had never seen anyone else fucking and was fascinated to see that he not only moved up and down, but also had a rotational actions with his hips.  The woman was crying out for him not to stop.  He didn't and she clearly had an orgasm and as soon as she could speak again she told him it was enough and he could finish up in the bathroom.  After he had pulled out I could see her used fanny was still wide open.  She told me to get dressed and as I did I noticed the huge rock on her wedding finger.


Rory had returned from the bathroom with a floppy cock and was also dressing.  She handed Rory an envelope and said she would see us next time.  As we made our way down in the lift I asked Rory was it always like that and he told me that some just want fingering others wanted just to play with his cock and some wanted sex for hours.  I asked him about his rotational movements and he informed me that if the woman was big down there it gave more contact and therefore more feeling.   He took money from the envelope and handed me what liked like two hundred pounds.  A asked wasn't the money for "The Man" to be told that she would have already paid him and this was a tip.  Although I felt dirty the money felt good.


A week later the thug again collected me along with a married lady.  He dropped her off at a dirty looking motel and me at a slightly better hotel.  The woman when she arrived was dressed like a high powered business woman in a suit.  Without even really looking at me she started to undress.  Unlike my first client this woman looked after herself and had quite a toned body and was fairly attractive.  "Well don't wast time.  Get undressed," she ordered.  This time as I undressed I could feel my cock beginning to grow.  She lay on the bed and splayed her legs showing her completely shaved pussy.  "Finger it.  I hope your hands are clean," she said.  I told her I had just had a  shower.  I was pushed down so my face was level with her pussy and I started to rub her pussy.


Unlike with the fat old lady, I was actually enjoying this.  As a young single man I was being paid, even if it was paying off my loan, to play with this mid thirties woman's pussy.  She not only looked good but she also smelt good.  I lent in and stroked her clitty with my tongue as I continued sliding two fingers in and out her pussy.  "You bad boy.  I didn't tell you to lick me.  But now you are don't stop.  Arghhhh," she groaned.   I was now lashing her pussy hard with my tongue and enjoying every second.


Then she was pushing me away and getting into the doggy position.  "Fuck me until I tel you to stop, but don't come in me," she demanded.  She needn't have demanded as I was more than happy to oblige and fuck her and would have willingly fucked her for free.  After ten minutes of banging away at her pussy I was struggling not to come.  Without being told I leaned forward and groped a tit whilst I reached around and frigged her clitty.  Fortunately for me she came like a freight train rumbling through her climax.  As she passed the precipice she shouted at me to pull out.


I did and came all over he arse.  "Clean me up," she insisted.  I assumed she meant with my tongue like the old lady and started licking.  She giggled and suggested that a towel would have sufficed, but then added that now that I had started I should finish.  Some cum had run down her pussy lips and as I licked it up she squealed and gasped loudly at my tongue touching her pussy again.  She asked if I could perform again and I told her given a little while I could.  She asked me to hurry up and get hard again.


I was really enjoying this and getting another erection wasn't a chore it was a pleasure and as soon as I was able to tell her I was hard she had me lie on my back and she straddled me and lowered her pussy onto my willing cock.  The ride she gave me seemed to go on for ever and I was loving it.  Then sadly like all things it came to an end as she came and slumped onto me with her tits in my face.  I started sucking them as I continued to hump up at her pussy.  She was moaning as she came down from her orgasm.  I was expecting her to tell me not to come in her again, instead she told me to keep going.  Then she had another mini come and it tipped me over the edge and I held her tightly as she trembled and my cock spewed my cum into her pussy.


Afterwards as I dressed she took her purse from her bag and put some money in an envelope which she handed to me and said that she would be booking me again.  I suggested that we make our own arrangements without "The Man" being involved and taking his cut.  She agreed and put my number in her little red book in her handbag.  On my trip home I was happy to find another three hundred pounds in the envelope and used the two payment to pay a lump off my loan.  The thug collected the woman who looked like she had gone through a ringer and had several marks on her chest.


"The Man" laughed saying that at this rate I would be debt free in about a year.   I just hoped that the clients would be more like the second one rather than the fat woman.  The next client wasn't fat in fact she was positively skinny and also the wrong side of sixty and her husband wanted to watch.  It was the first time ever that I had been watched fucking someone.  I was nervous that he was there and also that the woman looked so frail that I thought that I might hurt her or break something.


I didn't enjoy licking her and even less fucking her, but I did what I had to.  After I had come in her the husband was between her legs licking my cum back out of her pussy.  The tip he gave me was just fifty pounds, but every little helped.  The next woman was in her thirties, married and fairly attractive and wanted me to attend a party with her.   I was hung off her arm like an accessory all evening and in her car, as her chauffeur drove us back to her house, she had me lick her pussy until she came.   She wasn't interested in me getting my cock out or fucking her and after she was dropped off the chauffeur drove me home and handed me an envelope with some money in it and her phone number and a message to ring her.


She became another regular without "The Man" knowing.  Between my second lady and the fourth lady, they had also introduced me to several other women in their circles and I found myself with bookings about once or twice a week.  Some wanted just to have me with them, others wanted a variety of things up to ones that just wanted fucking.  In fact one of them didn't want any conversation or foreplay.  She would already be naked on my arrival and wanted me to undress in silence and just climb on and fuck her until she had come.  Whether or not I had come she had me get off when she was finished and dress and leave.  I couldn't complain at walking away with a raging hard on, as she was a very good tipper.


I re-payed my debt in ten months and "The Man" offered to continue finding me clients as he said I was popular with the married ladies and brought in good money.  I declined as I now had a fairly large clientele list of my own.  I was also able to select the clients that I wanted and not some of the fat old rich women that he pimped me out to.  Then I was passed a phone number by one of my regulars and told I would like her.


I called the number.  She was a very young woman and had inherited quite a lot of money.  She wanted me to be her plus one for the evening.  On the way to a function, in an art gallery, she had the chauffeur drive twice around the block as she had me lick her pussy out.  The function was boring.  On the way home she straddled and rode me as the limo glided along and she had the chauffeur drive until she had come.  She became my favorite even though I soon discovered that it wasn't just me that was servicing her.


Instead of just fucking her I worked harder to find what she liked best and hit on that she liked her nipples pinched hard as I licked her clit.  It always made her climax and then fuck her long and hard usually from behind.  Then I was being booked sometimes twice a week by her.  It wasn't a job and certainly not a chore to lick and fuck her and she obviously felt the same way as she started asking me to become exclusive to her and forego my other ladies.  She said she would give up her other men.   At first I said no, but over a period of time Helen booked me three sometimes four times in a week.  My other ladies when they couldn't get a booking slipped away.


When I was down to just two other clients Helen again asked me to be exclusive and said she would financially keep me.  This time I gave in and stopped my other clients and moved in with Helen.  That was almost thirty years ago and I never regretted a single thing.


Two things come from this, firstly don't ever get in debt and secondly If you ever get the chance to service women take it.  You will probably enjoy it, especially if you get to choose your clients like I did.