Gigolo Ch. 11

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The gay four-way continues; a lesson learned.
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Part 11 of the 11 part series

Updated 10/10/2022
Created 05/15/2008
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I originally had had in mind a shower for just me and Oliver, and was disappointed when Leo wanted to join. I quickly realised that this was because Tom would then have to join, and I didn't want this because despite him being absolutely beautiful and a terrific lover (from memory), I guessed I just didn't want to be in a position to witness incest. I didn't mind it, it seemed kinda natural if the truth be told, but the thought of watching Oliver fuck his son, or vice versa, just filled me with dread. But I recalled something Hannah had said to me pretty early into my 'career':

"Are you open-minded? Good, because you will have to see, perform and tolerate things beyond public conception. The weirdest, freakiest and quite possibly most illegal things are going on out there on the streets, and you have to be prepared."

The bottom line was; if I wasn't, my life as a gigolo was over and I was back to trying to scramble myself a job as a £20k a year bookkeeper. So if Oliver and Tom got under the hot jets of water with me and Leo, and proceeded to get up to all sorts of sexual activities, I had to take it. Whether or not I wanted to. It was the first sign of not having a choice I had seen in this line of work since I started. And I didn't like it one bit.

Luckily for me, and for my conscience, there was next to no contact between the two of them. My shower was big enough for more than two, maybe not four separately, but two pairs of guys fucking certainly.

Oliver was so keen to re-ingratiate himself with me physically and sexually, he helped me wash my face and hair whilst doing the same to himself and mixing in a few tender kisses to get me all worked up. And it worked. The touch of another hot man was sending me pretty crazy, and added to that Leo was fucking Tom to the side of us. Oliver spanked his son just once before I just bent him over next to Leo and tried to penetrate him.

I realised, just as my cock began to slide into his ass that I wished I had installed video cameras around here just so I could film this. It looked amazing; four hot guys in their physical prime with big cocks going at it with wet, sweaty bodies rubbing together. It was quite possibly the hottest thing I'd ever seen and experienced. And it was about to get much better.

You know when your hole just shifts slightly as if suddenly ready to take phallic intrusion? Well, Oliver's hole went just like that as my dick teased the crack of his ass, and all of a sudden I found myself inside him groaning in pleasure as he did the same and told me he wanted me to fuck him loads more. But right now, he'd settle for a really good hard fuck. And that was exactly what I gave him.

I liked cumming inside people; asses, pussies and mouths, and thankfully for me, Oliver liked people cumming inside him too. Namely his ass. My attitude to unprotected anal sex was avoid at almost all costs; even if you were both clean, you could still catch something. But Oliver was always clean up there, so there was never any issue. I grabbed hold of his shoulders and just rode his ass off until I came hard inside him. Oliver enjoyed it for a second before standing, turning, snogging me, licking me clean and then bending me over next to Leo -- who was still getting fucked -- and giving me the fuck of my life.

Unable to keep his hands off me, he grabbed my dick, got me hard again, and by the time he climaxed in my ass, I was about ready to blow my load again; this time in Oliver's face.

"Oh baby, that was good," I said after he'd wiped his face clean and Leo and Tom were just about to finish off.

"You're telling me," he grinned. "Worth every penny."

He pinned me against the side of the shower cubicle and saw to sharing with me the longest single kiss I'd ever shared with a man, and it was so good and with such a good looking and sexy man, by the time we finished, I was hard again. And so was he.

Leo had just finished fucking Tom, and suggested we go get dried off. I was about ready to go again, but maybe not here, so I agreed and led Oliver back to the bedroom where we dried one another off quickly and got back on the bed. I lay down on my side and Oliver did the same facing the other way. Cocks in each other's faces, we gave each other an almost loving 69er right there.

It was the end of the night before long, and I went to prepare some drinks. I was joined by Leo who I wasn't getting in with much because that would leave Oliver and Tom alone together. I forgot all that though as his sexy naked body strutted to me, dropped to his knees before my nudity and took me into his mouth. And I discovered Oliver, Tom and I weren't the only natural cocksuckers in the penthouse tonight. He swallowed my sweet cum before I shoved him to the sofa and soon swallowed his.

It was great, and we bathed in the afterglow for a little while before I noticed that my bedroom door was now shut. I got up, left Leo on the sofa and went to check it out. No sooner had I opened the door then I saw Oliver fucking his son's brains out. Quickly, and in a slight panic, I brought the door back to almost a complete close before returning my sight back to Leo. He was on his back stroking his penis; looking at me as if to beg me to join him. I had absolutely zero right to interrupt the incestuous goings-on in my bed, especially as I was being paid for tonight, so I grinned at Leo, mounted him and got a little more kissing from him.

"Grant?" I heard later that night, as we were all about to go to sleep. I was preparing myself a drink of water for the night, and turned to see Oliver.

"Hey."

"You saw me fucking Tom, didn't you?"

"Yeah."

"We've been caught before," he confessed, perching on the arm of the nearest chair. "The man sent the police to our house, we managed to convince them it was all a massive misunderstanding."

"You're waiting for a knock on the door?" I asked. He just nodded. "No, not going to happen. I'm not here to judge you, Oliver, I'm here to fuck you."

"And? I'm paying you a lot, but I wouldn't blame you."

"I've seen less tolerable things than a man fucking his son." I looked down with a coy grin. "It was kinda hot, too."

"Wanna watch next time?" he asked, but I was already waving him down.

"No thanks. Leo and I had some quality time together, and it was very good."

"I'm glad." He looked behind to where Leo and Tom were kissing in bed. "They're ready, coming?"

"Right behind you."

In the morning, we repeated the shower and bedroom exploits almost exactly but for the fact me and Tom fucked instead, and Leo and I didn't get alone time in the living room to exchange blowjobs, cum and saliva. Oliver got himself ready to make the wire payment for my actually rather exorbitant fees, and then he and Tom left. Leo was right behind him after giving me a kiss and his number. Despite everything, I wasn't sure I'd use it. I didn't make a habit of seeing clients outside of the job, and had only done so with Elizabeth and Emma (not counting Mickie).

I checked the place was nice and tidy before hopping in the Maserati and heading to my project house (not the one I'd inherited from Vera). I was in expectation of a visitor, but maybe Claire telling me about her first female clients and giving me some hot stories to fuck her over. I certainly was not expecting to step out of the Maserati to see Sam at my door.

"Sam?" I called.

She turned around to face me, smiled and half-heartedly waved as if she was pleased to see me but didn't want to show it. I couldn't blame her. "Hey."

"What's up?"

"Nothing," she lied, "how are you?"

"Sam, I'm serious," I replied and met her at the door. "I don't mean to be rude, but what are you doing here? I've only seen you once since you walked out on me, and that was a threesome with a client."

"I miss you," she confessed all too readily. I sighed, and let her into the house. Damn, this place was a mess, and certainly not the greatest venue for a make-up conversation. "I met someone else," she then confessed.

My head dropped and my heart almost broke again. I was in the most un-emotional job I could think of, and the moment I stepped out of it, I met a girl who'd taken my heart and ran off with it. I looked up. "I need to know this... why?"

Confused, she replied, "What?"

"Why come all the way around here, tell me you miss me, and then tell me you're fucking off again?"

Now she looked down. "I came around because despite how nice he is, I won't let him so much as even kiss me... because of you."

"Do you want my permission?"

"No. I want you to know that despite the fact I walked out and I sucked someone's cock in front of you, I want you. And nobody else."

I walked through to the kitchen and put the kettle on. She didn't follow; instead just leaving. Matt suddenly appeared by me. "Hey man, what was that about?"

"Women suck."

"Yes they do, and they fuck, and they..."

"Not what I meant, dude."

"Hey, chicks aren't all bad, man, some are great. Hannah, for example..."

"I know, but I don't want to be with Hannah."

Matt appeared to ponder hard. "Black chick, hot, frizzy hair, fantastic ass... that was Sam, wasn't it?" I just nodded. "Ah. I'm crap at advice."

"Oh, I don't need advice. I need to choose between Sam and this job."

"Is she making you choose?"

"Yes. She just doesn't know it yet. Coffee?"

Matt looked around the place. "Grant, I met this guy two nights ago, sucked his dick you know? Anyway, he imports RV's from the States, and I reckon you could do with one."

"Why?"

"Better to run the business from then a crappy table in a bomb site of a kitchen." I laughed, and then smiled. "He's in Central, come on, you can drive."

I spent the quarter of a million I'd just earned, plus another two hundred grand on a massive double-decker RV with a proper kitchen, living area and desk to work from inbetween the laborious parts. And I put them all to good use; interlinking hard graft and sweat with paperwork and relaxation. Plus if I ever fancied a break for a holiday, I could just drive out in this and forget a hotel.

The place was now just a shell, and I was working on some interior design when Matt came onboard.

"Hey man, it's getting to early evening. Checked your bookings?"

"No, not yet." I turned the laptop to him. "I'm gonna christen the bathroom, help yourself."

After a night full of gay sex, I was keen to get myself some tits and pussies, and so after confirming the three postponements I had from yesterday (all women), I confirmed two other potentials (both women too) and postponed a guy until tomorrow.

Matt left and I left the RV in the double-length drive before driving back to the flat in the Maserati. Expecting to see Claire there, I was surprised to hear from Joe she was out, so was Will and he was also on his way down to the pub. I was alone, until he told me I had a visitor.

I entered the living room to see Sam.

"Hello again," I said.

"Sorry I walked out earlier," she replied.

"I'm not," I confessed. She looked almost upset by that; I had to admit, it was a pretty harsh thing to say. "Why are you here now?"

"I came to ask you something."

Prepared to hear what she had to say, I perched on a chair near her. A quick check of the watch told me I had 90 minutes until my first client. "Shoot."

"Do you like selling yourself?"

At that moment, I realised what was coming. "I have fun, I enjoy it."

"Would you ever consider concentrating on property for me?" I looked down and actually thought about my answer. Apparently, though, I waited too long. "You know what, forget it," she said, and went to leave.

"The first time you left," I said, standing up. "That was before you knew what I did. Why?"

She stopped. "I was scared. I really like you. But I won't disturb you again. Bye Grant."

"I fell in love in this job once," said Hannah down at my spot. We were sitting on a bench waiting for our first clients and I'd just enjoyed a long tit fondling session.

"Oh yeah?"

"Yep. Didn't work. He found out I was a hooker and fucked off."

"Sam's right. I'd have to choose."

She shook her head. "No way you can have both, sorry babe. Do you love her?"

"I don't know. I've been in love before, and I'm still here. I'm not confident enough that it's the real thing."

"Want some advice?" she asked as my first client showed up; a brunette woman in her late thirties driving a Mazda. "Love conquers all. If she really loved you, she'd tolerate this."

"I wouldn't," I replied, and snogged her before walking to the Mazda. I put my head through the open window. "Laura?"

"That's me. Hop in." I did so and she drove us just around the corner before parking up. In fact, she ended up behind my car. "I've never had sex outside before," she said. "Have you?"

"Of course. Hop out." I stepped out and she did the same before meeting me by the bonnet of her little convertible. "Any number of places we can do it. On the bonnet, on the ground, against that wall..."

"I just wanna get fucked by that big cock of yours," she said and removed her top. This revealed a braless pair of very impressively pert CC cup boobs that I fondled.

"Show us that pussy, then."

She showed it to me more than readily, and perched up on the bonnet naked. Some of these clients... honestly, I didn't know why they had to pay for sex. Maybe they just wanted to. I opened her legs, treated her to some oral foreplay, and then put on a condom before fucking her so hard, she almost fell off the bonnet and onto the ground. I made sure I lasted long enough to make her cum twice, before following her instructions to drop her to her knees and spunk down her throat. With a little time left, I licked her hot pussy out and fucked her one more time before taking the standard fifty g's in cash and getting dropped off at the spot.

"Evening baby," said Mickie, meeting me after I'd left the car.

"Hey sexy," I replied and gave her a hard tongues-in kiss whilst putting my hands up her top. "Damn, have your tits got firmer?"

"I'm getting plenty of exercise," she giggled. "And all the spunk makes my skin nice and smooth. Staying with me tonight?"

"Definitely." I looked right to see my next client arriving five or ten minutes early. I didn't care, though, any bodily contact with Mickie was enough to get me going again. "I'll call you later."

"Bye babe."

I walked to the car and saw my second client through the window; a largely unattractive woman in her late twenties. "Hey, you wanted to fuck?"

"Get in."

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READ MORE OF THIS SERIES

Gigolo Ch. 10 Previous Part
Gigolo Series Info

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