Gigolo Ch. 05

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A new hooker, friends re-united & romantic heartbreak.
3.6k words
4.11
11.2k
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Part 5 of the 11 part series

Updated 10/10/2022
Created 05/15/2008
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"Can I thank you? Because a girlfriend told me that wasn't the thing to say," she said. I just giggled, snogged her and fell off of her.

"You're welcome," I chuckled some more, standing off of the bed. "Night's still young, champagne and a Jacuzzi?" I asked, well aware I'd see her again if I gave her the Presidential Suite in Central to solicit from whilst she earned enough money to buy her own place, which, if she was half as hot as I thought she was, would take less than a week.

"Nah," she replied, to my surprise. "Where's this website of yours?" she then asked to my delight.

After a little look at it, and a little plan, I broke her anal virginity, we shagged once more, had a 69er, then slept until about nine in the morning. I brought her breakfast in bed as a treat for sucking me off at six in the morning, swallowing, and then just going back to sleep, and then we got going.

The plan was to change the name of the website from cockfostersgigolo.co.uk to cockfosterscocklovers.co.uk, and then bring in not just Mickie, but many others, including Matt and Hannah.

Those two came around for Sunday lunch at the nearby pub, but did so at around eleven so Matt could set up his digital camcorder and film Hannah and the rest of us in action for teaser videos wannabe clients could watch before deciding who they would hire.

Mickie showed she was 'up for anything' as the introduction on her web page stated, by licking Hannah just before we went out. Matt and I didn't have full sex once more, although I could tell Matt was frustrated. He just stuck his cock in Hannah's mouth whilst I banged Mickie in her cunt.

After lunch, which Hannah paid for in its entirety, I paid thirty grand by wire for a secure payment system clients could use to pay by before, during or after we gave our services. I then paid five grand for a company to independently maintain it from a centre in Bristol.

Matt filmed me in a video masturbating for about a minute before I returned the favour. Hannah then left Mickie to ride him whilst I helped give the young slut her first taste of DP by shagging her up her arse. Matt and I cuddled her between us, groping her tits and snogging each other.

"Is she clean?" he asked as she, naked, prepared a Jacuzzi for us. Hannah was over hers preparing clothes for herself and Mickie, and would be back any minute to start sharing make-up tips and getting ready with her. I almost felt like asking Hannah to take her out with her, but I wanted Mickie with me tonight. And by the results on the website so far, some agreed.

I replied to him, us lying naked on the bed cuddled up with each other although we still weren't shagging. "Probably, although I will have her tested in no time just to make sure." I heard Hannah come in, and soon she was in underwear carrying a small rucksack entering the bedroom. She tossed the bag to one side, and stripped topless. "Hey Han, got five bookings for you."

"Sweet, let me see." She shamelessly got inbetween me and Matt just as I felt like getting off with him again and maybe letting it progress to some full on gay sex. "You two go and join Mickie, have some fun." She winked at both of us in turn and touched our knobs. "You know what I mean."

Mickie got even more fun in the Jacuzzi than she planned for in another threesome with Matt and I. Matt bent her over and started banging her in her tremendous arse whilst I lubed him up, put another rubber on and slipped into him. I tickled and grabbed his balls whilst kissing his neck, licking his tongue and helping him grab Mickie's bouncing boobs. He added to that by slipping two fingers into her cunt to try and make her cum as quick as he was.

Hannah came in, telling us she'd accepted all five bookings, all from at least semi-attractive female clients, dropped her thong and made me and Matt withdraw from him and Mickie.

She sat Mickie up on the edge of the Jacuzzi, opened her legs and began touching her boobs and getting off with her. On Hannah's direction, Matt and I then gave each other a handjob to spunk on Mickie's pussy, stomach and tits. Hannah then returned the earlier favour by licking her out as Matt returned my favour to him by banging my arse off with what was actually a pretty violent, but incredible shag.

The bookings came in thick and fast, Matt coming off the worse despite having two guys and two girls ask for his time. Hannah had one more booking as we already knew, and as Mickie and I were going together tonight, we'd arranged eight bookings with equal amounts of money each. We accepted seven, deferred one and giggled as a guy asked for Mickie to himself for a whole week for £10million.

It was an incredible figure, and one Mickie couldn't turn down, especially as I couldn't dissuade her. She'd go with him everywhere he went during the day, like a young trophy wife, and have loads of unprotected sex during the night. I booked her in for a doctor's appointment to get her tested and put her on the pill, whilst deferring one booking until next week.

Our first client was a woman; quite cute and in her thirties, dressed in a pair of jeans ripped on one buttock that exposed cute pink panties and a bit of ass cheek. A single mother-of-three, she was bored and looking for excitement whilst her babysitter -- an ugly bespectacled girl Mickie's age -- looked after them.

Mickie licked her whilst I shagged the small-breasted but fantastic assed slapper (her three kids were by three separate fathers; her ex-husband, her ex-husband's father, and her babysitter's older brother (or her father, she couldn't work out which because she'd shagged both on the same night she conceived)) up her arse, and we got twenty grand each, cash.

Our next five clients were largely unspectacular, other than a woman who did want unprotected vaginal sex from me and for Mickie to sit on her face, for a hundred grand each. She was quite pretty, but wouldn't take her top and bra off. The word cancer came up once, and I knew that a mastectomy had taken some of her dignity and all of her sex life away. Once she'd taken her hands off Mickie's boobs, she wired us the money. And once she'd done that, Mickie and I had racked up a two hundred and twenty grand cash, each, and one hundred and fifty thousand pound wire transfer funds.

Client number seven arrived at three in the morning just wanting a quickie with the pair of us. Client number seven was also a rich young couple I used to know when they were poor; my old housemate Emma and her boyfriend Martin... desperately wanting, and in need of, some partner-swapping action.

Fifty grand each got them a warm-up in my house, on my bed... Emma and Martin romping nude together whilst Mickie and I had a good hard shag. Then, Emma -- not recognising me because I'd changed so much -- sucked my dick for a short period and then just rode me for ten minutes; Martin shagging Mickie doggy style in such a fashion, position and direction that I could snog the little slut and Martin could snog his girlfriend.

We all fell asleep, then woke up at ten o'clock to receive another ten grand each so Martin could get a blowjob from Mickie in the shower, and Emma and I could get some privacy -- her still oblivious to my identity -- so I could lick her and then shag her for no extra fee. I gave Emma my card, told her next time would be free, and then they left.

"That was so good," Mickie giggled as she remained in the shower washing Martin's cum off of her and I went to join her.

"You enjoyed it all?" I asked, entering with a hard-on in a rubber; I stood behind her, opened her legs, slipped her my length and began slowly moving as I groped her tits and kissed her neck.

"Definitely. Think I can buy a house?" she asked.

"With four hundred and thirty grand, definitely," I replied, moving a bit quicker now. She began moaning in pleasure. "But I'd wait a bit longer. I'm off tonight, so go out with Hannah, earn loads more, then we'll see what tomorrow brings."

"I wish I'd had that girl, she was gorgeous," she giggled.

"Yes, she was. An old housemate of mine; wish I'd fucked her a long time ago. I offered her a repeat one-on-one performance for free."

"Wish I could do the same for her boyfriend," she replied.

I chuckled; I remember Emma having very loud orgasms whilst with her ex; nothing like that had happened with Martin. They clearly loved each other, it was just he was actually quite small, and although Mickie did actually cum, it took a bit of fantasising and touching herself up to do it. "No night is ever perfect," I thought, thinking back to the hen night girls, then thinking of Sam and those lovely breasts I was dreaming she'd show to me tonight.

Hannah accompanied Mickie to the doctors' surgery to get her checked over, and for her to get the all clear. The GP was a very handsome Asian chap Hannah was so fond of, he only had to turn up to get half hour shags for free. According to him, sex with his wife by an arranged marriage 14 years ago was dearer.

As he knew the score, he got Mickie on the pill, gave her advice and leaflets, and had a five minute quickie with both over his desk.

As she was in the clear, she could accept certain offers; one virile looking man asked for unprotected sex with both; attaching proof of his health with the e-mailed booking order form. But, even though she did accept, I could tell something was bugging her as we lay in my bed; Hannah, Mickie and I.

"I want you to be my first," Mickie said. "You know, the first one to do me without a condom."

I grinned; thinking of how not even Hannah and me had gone bareback yet, and yet here I was about to do it with little ol' Mickie. "Baby, I would be honoured to spunk my hot cum inside your cunt," I replied and mounted her.

Hannah lay beside us, as we slowly made love that culminated in one climax for me, and three for Mickie, fingering herself. The sex was awesome; Mickie's still tight and practically virgin pussy felt tremendous against my big dick, and I spunked inside her. Thankfully, she was on the pill, else I was sure our synchronized climaxes would have resulted in pregnancy.

I left her and Hannah to have a 69er and plan more bookings for tonight, as I checked mine and deferred all but one. Sam was due around the flat at eight, and Emma had already been on my website and asked for an hour with me in private.

Not seeing the point in waiting until dark, I kicked Hannah and Mickie out at four, welcomed Emma into my house and banged the absolute fucking stunning tits off of her naked, E-cupped and neat-arsed beauty, first through vaginal, then through anal.

Feeling more like two legitimate lovers having an evening in bed (hopefully a sneak preview of tonight with Sam), we continued on until seven; finishing up with Emma's soft lips around my knob as I climaxed down her throat after half an hour of incredible oral sex. She swallowed, asked for another repeat performance -- which I granted -- and then left after a two-minute quickie shag in the hallway in which she removed her thong and left it on my hallway carpet.

I saw her to her car, snogged her and asked to meet her on a more regular basis. If Claire was cool, and so was Sam, then to make Emma my third lover outside of the streets would be ideal. And Emma was so fit and so fucking good in bed, I actually almost didn't mind sacrificing Sam.

An hour later, I lay in bed with another hottie, though, and it was Sam. She'd asked me honestly if there were any other women in my life, and I answered honestly with an vague yes.

Now she was topless again as we snogged and I once more touched her lovely boobs. She was moaning, getting more into it and although we'd started off with a chat, as soon as I had her on her back with her gorgeous breasts naked to me, she was butter in wherever I put my hands.

Up her skirt went one, stroking the crotch of her clearly lacy panties. I put the other one under her, moving my tongue from her mouth to her tits and began licking her nipples as I fiddled around her fantastic arse and managed to pull her skirt down to reveal red lacy panties my top hand immediately went inside.

She groaned more, telling me she wanted more, and much, much more as I touched her naked pussy for the first time and my bottom hand began toying with the idea of removing the pants altogether.

Suddenly, though, I was on my back as she mounted me, pants crooked as a pussy lip poked out and began snogging me whilst tugging at my jeans. Soon, she knelt up between my legs, undid my jeans and pulled them down with my tight boxers to reveal a hard cock she sighed at. She then put her head towards it.

Fuck me, forget Hannah, forget Mickie, Emma, Claire... all the other male and female clients... Sam gave me the most incredible blowjob; sucking, licking, spitting, jacking me off inbetween mouthfuls, and then once I spunked down her throat, just swallowed, grinned, giggled and mounted me.

With a long snog, she gave me time to put my hands down the back of her pants and fondle her fantastic arse for the first time properly, only to, five minutes later, get off me, stand up on the bed between my legs and tantalisingly tease her thong-like knickers down to her ankles, where they remained as I made her crouch, and moved myself down the bed to suck on her cunt for about half an hour. She moaned to two orgasms, then just after the second, I moved back to my original position and handed her a condom to put on me.

She crouched back down, sliding her fine wet pussy around my knob and gently riding me for the first hour, until we just fucked each other's brains out for the rest of the night. In the end, little conversation passed, but we had loads of climaxes and orgasms each, exchanged oral more than once, and even had anal, which with her arse, was truly spectacular.

In fact, I was surprised at what I saw the next morning, when I woke up. It was Sam, in everything bar her skirt, dressing as I still tried to sleep. In fact, it wasn't even that light outside.

"Are you okay baby?" I asked, reaching out to grab a handful of her arse. She let me, which didn't allude to what was coming.

"Yeah. Erm... look, I think with more than me out there, this maybe shouldn't happen again."

I almost leapt out of bed, sitting on the edge with the quilt exposing my modesty. "Babe, what's brought this on? Last night was amazing, wasn't it?" I asked. No, it really was amazing, Sam was an absolute legend in bed, but with her looks and physique, it wouldn't surprise me if she'd had plenty of male partners to practice on from sixteen to what she was now... twenty.

"Yeah, of course it was. It's just... I'm looking for a relationship, you're not." I looked down. "Look, we can see each other again maybe, some point in the future perhaps. I might bump into you at a club; ask to see that dick of yours, but... I'm sorry Grant. This isn't what I need. I hope you understand."

I asked her if there was anything I could say to make her change her mind, but there wasn't. It was made up, and soon her skirt was on and she had left. I was actually really fucking gutted; it was a proper heartbreak, but as I assessed other options, I realised all was not lost.

And so I put on my boxers, crept down the corridor, knocked on Claire's door, and woke her up by bending her over the desk and fucking her tits off.

"Ah well, her loss," Claire observed after I'd told her all about it and made her cum. She turned around, pulled her trackie bottoms up over no underwear, and remained topless. I held her by those lovely tits of hers. "She'll probably be back before long, though."

"I hope so. No offence."

"None taken, although... just to be sure," she continued, holding me around the shoulders, "better show me that you want me to stick around too."

I grinned, and just yanked her trackie bottoms back down before groping her arse so hard, I left handprints. Then, I sucked on a boob. "Thought more about solicitation?" I asked.

"Yeah," she groaned as I slid a finger between her butt cheeks and fondled around for her asshole. "A little, but not much. I've spent a little of the cash on course materials, and stashed the rest in a high interest bank account. I really enjoyed that guy, but..." she paused to move back to the bed and lie down, "... I thought it might have been a peak. Plus," she added as I took her bottoms off from her ankles, mounted her and continued licking her tits, "I don't do girls at all, not under any circumstances." I somewhat doubted that, but I wasn't going to challenge her.

"You don't have to," I explained and dismounted her, although I did remain next to her, stroking her boobs. "Come on my website, do some photos and a video with me and-or Matt, then you can pick and choose bookings. Baby, you can have a choice. I just have everyone because I like money. You pulled in five grand with a simple doggy style fuck; you can get yourself through uni in a week despite picking and choosing clients."

"You reckon so?" she asked, almost hopefully. I was surprised how so many girls were flattered at being told they could be the best damn whore going. I put Mickie's glee down to the fact she was, regardless of her beauty, body and fun nature, a moron. Maybe Claire didn't get that many compliments.

"Absolutely. I wouldn't condone being a hooker altogether, you're too good for that," I explained, forgetting that maybe Hannah was too. "But you've got the big tits and tight pussy men want. Plus you're black, which always helps."

"Make some calls," she suddenly replied.

Three hours later, we were at my new house and after I'd given her the guided tour, I introduced her to what was becoming 'the gang'; Mickie, Hannah and Matt. Mickie tried copping off with her, but was knocked back more than once and got the hint the sixth time. Hannah knew better, but just complimented her on 'the rack' (i.e. her titties), and entertained Mickie in a highly entertaining and sexually arousing fashion.

Matt went down very well, and not just in the introduction stakes. I filmed her stripping naked and then getting licked by Matt to an actual real climax. A spectacular scene I joined in on by shagging Matt to Claire's shock and stimulation, and one that would only increase Claire's chances of getting lucky tonight. And as if that wasn't enough, we also filmed Matt and me fucking her mouth and cunt.

Hannah and Matt took her into Central clothes shopping, making her miss her two Tuesday lectures, and I just shagged Mickie senseless whilst waiting for bookings to come in.

Unsurprisingly, Mickie was once again popular, after raking in half a million pounds yesterday for her exploits with Hannah, three guys and an old lesbian couple who just wanted to watch. Apparently, they'd taken three guys back to the Presidential Suite, had multiple orgasms, and Mickie let the hottest one go bareback before, this morning, they had loving girl-on-girl sex alone and promised to have some nights alone soon like Hannah used to have with me.

Mickie accepted client bookings worth another six hundred thousand that would only take her to three o'clock. I offered to meet her back here afterwards, and accepted all five potential bookings from a really old man whose gay lover died five months ago to a fit-as-fuck foreign chick from Kenya with money and absolutely no company.

Claire returned after being shouted ten grand's worth of tiny clothes and lingerie by Hannah, and accepted only one of her eight potential bookings; a fit guy who'd put on a picture of him, his buff abs, and large penis. He was to arrive at half six, so we all got ready and left.

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Gigolo Ch. 04 Previous Part
Gigolo Series Info

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