tagNovels and NovellasGigolo Ch. 01

Gigolo Ch. 01


This is a long-term story with potentially an infinite life in it, and it revolves around a man (written from a first-person perspective) finding himself in deep financial trouble and finding money and enjoyment in becoming a high-class male hooker. This chapter, as well as the ones to follow, will hit on more than one particular genre, which is why it's been filed here instead of anywhere else.

If you are open-minded, like something different and are not easily offended, please read on and give me your honest, constructive views. This series will contain scenes of lesbian, gay, teen, first time, group, interracial, mature and incestuous sex.


"Right, you've completely lost me," said my buddy and housemate Will as we sat in the living room of our Cockfosters apartment. "You move up here to be a bookkeeper, which you studied to be for eighteen months, and... hold on, let me get my head around this... a gigolo?"

"Uhuh. I've done it for a couple of nights, enjoyed it... two nights, fifteen grand."

"Hot clients?"

"Not always. But, you know what they say; when sex is great, it's great. And when it's bad, it's still pretty good."

He chuckled and scratched his hair. "Erm... hours aren't very sociable."

"True. But it's cool, I enjoy it. Besides, it's not a career choice, I'll still be a bookkeeper soon, it's just that I can't spend my life getting turned down for twenty-five g's a year vacancies because I don't have any experience and nobody will give me any. Before Tuesday night, I was down to the last hundred quid in my overdraft. Talk about selling your body to pay your way through college."

"I got bar work, dude."

"Eighty quid a week, two nights... big whoop. That's bagels for breakfast, and no cream cheese. And an eviction order," I added, but Will was already waving me down.

"Fair enough. Telling Joe and Claire?"

"Sure. They'll find out." I checked my watch. "Dinnertime. I'm hungry. What do you fancy? Nothing big, I'll be out tonight."

"Let me grab my shoes, we can drive to that Chinese the top of Mount Pleasant."

Being a gigolo had been easy this far, mainly because I liked sex so much, men and women (yes, both) agreed to the charges, and partly because I hadn't come across any real ugly clients, aggressive clients or cops. I knew I had to be careful and take precautions, so standing and / or walking around in a dark street in normal clothes was necessary, as was carrying a switchblade I'd bought off a drug dealer the last night I solicited.

Thursday night Will worked at a local pub, so I waited a bit longer, put some nice clothes on and drove two miles away to near the street I had stood before. Someone else had had that spot, but now they had 'retired', the spot was all mine. The road was dark, badly lit, rarely frequented by cops who had knife and gun crime to worry about without prossers and kerb-crawlers, and well-known as a red light district. I was a high-class hooker with good looks, a large penis and high charges the rich businessmen / women of Central London could come north for.

I'd been around for about half an hour when a Mercedes pulled up and the window wound down. I moved to the window, looked in and saw a pretty attractive woman in her late thirties still dressed in her suit. I had to turn on the charm.

"How can I help you, darlin'?"

"Erm... how much do you charge?" she asked slightly nervously.

"What are you after?"

"A shag," she giggled. "Nude. Plus kissing. I got a hotel room."

"Great." I tossed my bag -- full of condoms, plus a change of clothes if needs be -- in the back and sat in the passenger seat. "Let's go, we'll work out rates on the way."

"Oh shit yes, oh shit," she moaned as, in the hotel room, she rode me in the nude. Despite the fact it was strictly against 'the rules', I'd agreed to take her five grand and agree to snog her and tell her -- truthfully -- how attractive she was.

"You like that, you slut?" I asked, grabbing her tits.

"Well worth the five grand, best fucking sex ever you fucking stud," she screamed. "Just one shag, or can I get more?"

I was cool to bargain with them because I didn't have a pimp and I was completely independent. Prostitutes, male and female, weren't supposed to drop the veneer when around punters, but I couldn't be assed. "For your fucking hot body, I'll lick your cunt and fuck your arse."

"Evening," I was greeted with as I stepped out of her car back at the spot. I'd given her what I'd promised, plus letting her suck my dick for five grand and her moist panties. Those panties plus the five grand in a hundred fifties were in the bag, and the person greeting me was a lady prostitute; a 18 year-old girl called Hannah was a little dirty, but popular and quite well minted because of it.

"Hey baby," I replied, meeting her and snogging her with my hands up the back of her short skirt. "Good night so far?"

"Not bad. Old dude with a grand shagged me hard, I actually almost came. You?"

"Fit bird from Central, real tight cunt. Not as tight as yours, though."

"Bet her tits were smaller too," she grinned. I groped them; large, pert double-D cups attached to her otherwise thin body. "Around the corner for coffee?"

Another car pulled up; an old Audi convertible driven by a good looking guy. "Doesn't look like it. One for you, I think." Unsurprisingly, he called Hannah over and they soon drove off.

A problem I was having money wise was all the cash I had built up in three nights so far; thirty-two grand in total, with no bank account to put it in. Knocking up to my local branch of HSBC on High Barnet High Street every day with five figures worth of money in hard cash would look dodgier than a Mafia godfather hanging out the window of a Beemer 3-series holding an Uzi.

I had to think up a plan.

As I drove back from the road to the flat, Hannah in tow as she was going to stay the night away from her crappy parents, I formulated a plan involving myself, computers and the world wide web. If I created a website, I could hand my clients my business card, and they could check me out and maybe make advance bookings for all-night sessions. Then if I carried my laptop around with me, I could do exchange internet banking with relevant clients and get the cash straight into my account.

The next day, a Friday, Will was at lectures until early afternoon, so I stayed in bed fucking Hannah until late morning, and drove us into Enfield Town. She went house hunting to use her ninety grand nest egg to put a deposit on a nice place, and I went to my branch of HSBC with two grand, paid it in and moved my money into a business account with a 8.9% interest rate (with at least £1,500 paid in per month), telephone and internet banking. I treated myself to some CD's, DVD's and Xbox games (spending about a grand), met with Hannah who had as yet had no luck, drove her to her folks house and returned home to chill with Will.

Again, that night, I headed on out and was sitting on the bone dry kerb reading the classifieds -- looking for something new to move onto before I got too attached to this life -- when a fellow guy gigolo came up and sat next to me. His greeting of a snog was slightly forced, but enjoyable and afterwards, he introduced himself formally as Matt, although I already knew him as Hannah's cousin.

"How long you been doing this?" I asked, putting the newspaper down behind me. There it would stay; my bag was primed for more cash and was already carrying my laptop and business cards.

"Twenty months," he replied.

"You like it?"

"I love the money, and most of the sex sure. I live in Central, got myself a penthouse suite on the Docklands and a Lotus. I introduced Hannah to this because her folks want her to become a nurse, and with all respect to her, she hasn't got the brains. What she has is the rack and technique. What's your story?"

"Don't have one. This is night four, I'm just enjoying making a bit of cash until I can have some holidays and settle into a career as a bookkeeper."

"Cool. You worried you'll enjoy yourself too much?"

"Too late, already am. It's not a career choice, though."

"Course not." He gave me a card with his mobile and home numbers on it, plus his e-mail address. "See you around, and take care of my baby cousin."

"Already do." I handed him my card, including the website address of the website Will had helped me construct called cockfostersgigolo.co.uk that was still under review. A car pulled up; a brand new Rolls Royce Phantom Limousine that was twice the size of the original. The back passenger side window came down and I was there to peer through it. To my surprise, I saw a very old lady there. "Hey there love, what can I do for you?"

"I'm 104," she doddered, standing unsurely. "Good heart, but about a week to live. Any chance of some good loving to send an old woman to heaven happy?" she asked. I looked her up and down; she was actually pretty hot. But the sob story plus the fifty grand she promised me was even more pivotal to me saying yes. "Good. Get in, I have a Presidential Suite in Central. Is this all night?" she asked once I'd stepped in.

"Don't know. We'll see. Fifty grand will get you at least five hours of me however you want me."


"No lady, I don't go bareback," I immediately and rather admirably if I say so myself replied. "House rules."

"That's a shame. I haven't got any diseases."

"Sure, neither have I. But things can still happen." The car moved off and the lady leaned over to what looked like a mini-bar. "I'm not drinking, I have to drive home afterwards."

"Drink now, then you stay the night yes." She pulled out a big bottle of champagne. "This costs five grand a bottle, enough of an incentive?"

I grabbed a glass and leaned in for a kiss. "Should we get started?"

Within an hour we were on her bed; her naked as I shagged her. "Good, yes?" she said.

"Holy crap yeah," I panted, looking at her breasts. "How are they so pert?"

"Lots of exercise, a little plastic surgery to have them reduced. I used to have double F's you... oh fuck you young stud... you know. If I didn't have them down to single C's, they'd be around that fat cock of yours."

"Well, thank fuck for that, I get to stick it between these stunning pussy lips," I replied, looking between her legs to the shaven pink folds of skin that were her cunt. "Oh fuck, I don't think I can hold on much longer," I groaned.

She let out a squeal that almost made me forget she received a Queen's telegram when I was still in college. And as great as she looked naked, she was still wrinkly in places. "Same here. I haven't had an orgasm for twenty-five years, and I am going to cum... oh fuck, yes, yes, yes!" she screamed, before I felt and saw her orgasm. The contracting pussy tipped me over the edge and I fell on her, lips on hers as I came. "Ooh yeah, that was so good," she moaned, unable to cuddle me into her. "Drink?"

"Go ahead," I said, falling off and trying to maintain an air of not caring about the client. "I'll have something softer."

"In the mini bar, help yourself," she said, turning away from me to grab the glass. Her ass was a little wrinkly too, but as she was born in 1903, I thought I could handle that. "Oh, and be a dear and run us a bath, I feel like a dirty whore."

"You're on."

I did end up spending the night with her, taking the money by wire transfer before licking her pussy and being dropped off by my car, a 1979 MG Midget in good condition I'd bought a year ago, and driving home.

"Fifty grand?" said Will during breakfast we ate before Will probably spent the day studying or playing Skate over Xbox Live. "What are you going to do with that money?"

"Deposit on a nice house. I dunno, we'll see."

"Out tonight?"

"Probably. What were you thinking?"

"I wanted to go into Soho for some clubbing, but... I'm weighed under by study."

"C'mon dude, you have to take some time off from it."

"I'll see how I go this afternoon. Any chance you could give us a lift to and from Sainsbury's in a little while, I need some things."

"Sure, no problem. And I'll take care of those bills too. Don't tell the guys."

"They'll twig soon enough, bud."


Will's afternoon didn't go well, so he decided to stay in and I decided to go out. After handing Vera -- that was the lady's name -- my card, she'd made a booking on my website for another all-nighter at her hotel room. She asked me if I would go bareback for sixty grand, and I said no, but we agreed sixty grand would still be the fee if I treated her to some DP -- me and a guy who would get ten grand more.

"Darling, that was wonderful," she said after Matt had left. As Vera would give me a lift most of the way home, I'd given Matt the keys to the MG I'd driven us here in and told him to leave it where I usually left it.

"Glad you liked it."

"Thanks for kissing him too," she giggled like the oldest schoolgirl ever. Sometimes, she was just so sexy, but other times, I was really reminded about the fact she only had a few days to live before her developed lung cancer broke through the drug barrier and took her life 104 years after birth.

"No problem. What do you want to do now?"

She dismounted me and got on her hands and knees. "I used to love anal with my late husband Harold."

"Let me grab a rubber."

Only a few minutes after penetrating her, beginning to shag her and groping her fantastic breasts she'd revealed earlier to Matt and me from a sexy bra she must have bought from La Senza or some other lingerie shop, she actually came and collapsed on her front, telling me I could just cum and be done with it before we could have a little something to eat. I then spunked over her great tits in due course.

Over the next two days, I barely saw anyone else, even though the next night, I added to Vera's seventy grand fee with three grand to shag a thin kinda ugly chick in the back seat of her Vauxhall Astra early on before she picked me up, and then the next night an all-guy threesome with Matt and a punter that earned us twelve and a half grand each before Vera picked me up and treated me to another night with a woman I was unfortunately getting very attached to with eighty grand wired to me to sweeten the deal.

As I felt bad about getting emotionally attached to a dying old woman who had only met me because she wanted to pay me to screw her, it turned out she was very attached to me too, referred to me to her sole surviving friends as her 'toy boy', and wanted to tell me parts of her life story.

Not that I was bored or anything, quite the opposite, and actually told her more about myself, my pre-existing depression and bad luck with, well, anything actually. As soliciting was the only thing bar getting my bookkeeping qualification that had gone well for me so far, I was feeling pretty peeved and she was incredibly sympathetic.

Things almost went from bad to worse for her as I was awoken at half five in the morning by Vera who switched the light on, poked me, wheezed a lot and pointed to her lungs. An hour later, paramedics left.

"Thanks darling," she said, still lying back although she was sounding much better now the paramedics had dispensed an emergency ration of her cancer drugs to stave off death for another 24 hours.

I sat down on the bed in a hotel dressing gown, and sighed. "Bit scary, ain't it?"

"Oh darling, I'm sorry. You're so young, and I'm surrounding you with death."

"Not death. Spirit."


"Yeah, you ain't giving up are you? No, I'm not gonna close my eyes and let it all take me away, I'm gonna get some drugs and keep riding a gigolo."

She chuckled, undoing the strap on her gown revealing her body. "Grant, dear?"


"I want you to know something."

"What is it?" I asked, removing my gown and dragging hers off from under her. I put the quilt over us and cuddled up to her.

She smiled broadly. "I have got myself ashamedly attached to you. You're a wonderful young man, much more tolerable than my own family, which is exactly why I changed my will today."

A woman with -- so far -- a quarter of a million quid to toss away on a male prostitute had to have some serious funds locked away. And my expression gave away that I knew exactly where she was going and wasn't sure I wanted it to go there. "Okay."

"You are sole beneficiary and executor. But on one condition."

"Name it."

"I pick you up early tomorrow, we have a meal downstairs, then we come up here and you make love to me unprotected." She could see I was very unsure, and was actually about to just go ahead and say no when she shushed me and retrieved a document from a bedside drawer.

"What's this?"

"Test results. I got the full spectrum tested yesterday. I'm clean."

"What if I'm not?"

"Darling, I have about 24 hours to live, do you think I care about Chlamydia?" she asked with a raised eyebrow. I chuckled. "I thought not." She put the document back once I'd read it and cuddled me back. "Now, a little more sleep?"

"Sounds good."

As the next day, when we awoke again, was a Monday and I was likely home alone when I returned to Cockfosters, I shagged Vera twice instead of once, took eighty grand by wire again and went into Central instead of home to hook myself up with new expensive clothes costing me a fraction of my three hundred grand bank balance.

As Hannah was with me, she told me not all clients were as rich and generous as Vera and sometimes we just had to take what we could get. Last night she'd shagged a guy who could only give her two hundred quid. But once she'd found a sugar daddy in his mid-fifties who, shortly before being locked up by the Inland Revenue for tax evasion, treated her to twenty-three nights of passion earning her over two million quid. She'd since blown most of it on clothes, nights out and even a house she was renovating so she could move out of her parents home.

"I dunno, it's not like this will be my whole life, you know," I said as I tried on £350 jeans that had patterns on the buttocks to make my ass look even nicer. Hannah was with me in the dressing room alluding to a closeness we had from only ever shagging in my place and not with a client as I had with another woman, 36 year-old Paula who wasn't with us. "I've made so much money, I can just keep going for this part of it and live off interest in a nice home, with a career, maybe settle down with a fellow young professional."

"You're lucky, you've got that to fall back on," she replied, touching my bum. "I haven't. Yeah, I love these, buy them."


"Yeah, absolutely, do it."

"Okay, you're on."

"But before you do," she said, sitting on a bench as I undid the jeans and dropped them, "I'm horny."

She took my dick out of my pants and immediately began sucking it. I immediately wished a shop assistant would come in and help her. Not that she needed help; I came in minutes.

I asked her what the chances were of me returning the favour, and she grinned before naming a lingerie shop.

"Is everything okay in here..." a gorgeous shop assistant -- short but with perky large breasts -- asked, moving through the curtain in a changing room to see Hannah perched on another bench wearing just a bra as her naked pussy was spread before me; kneeling and licking her passionately. "Oh, erm..."

"Don't stutter when there's room for one more," Hannah panted, holding her hand out.

In moments, the girl -- named Ruthie and only nineteen -- was completely nude and holding Hannah's bottomless body to her as they stood and snogged. She unclipped Hannah's bra and had no sooner done so then was pushed to sit down and watched a girl a year her junior drop to sexy knees, open Ruthie's legs and begin sensually licking inside her thighs.

Meanwhile, I'd stripped naked too and was holding my hard knob out in front of Ruthie's face; stroking her fantastic 28DD tits. She looked up at me, winked and then just grabbed my huge appendage before ramming it down her throat.

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