Men I’ve Loved Fucking

The Other MILFs — John

That was the game he chose, so that’s what he got: a bored, business-like BJ

Tori regales her therapist with selected highlights of her sexual history. This is part 10 of a 26 part episodic series; each chapter is a stand-alone story and will be published here on Tantalizing Tales each Wednesday. You can find them all here…

Doctor Bonner scribbles a few notes, possibly on impotence, then looks up with a smile. “Thank you, Tori. That was… enlightening. It sounds like you’re usually extremely submissive with Ian, but as I recall you were aggressively dominant with the cyclist. Would you say you enjoy playing with power in your sexual encounters?”

“Sex revolves around power, Doc: it might flow and shift, but it’s always there. As long as everyone’s playing, and no one forgets where the power truly lies, that’s cool. Like, Hansel thought his money gave him power over me. It didn’t, but I played along while I was enjoying it.”

“And you enjoyed it because sex work is an enticing taboo?”

I hadn’t thought about it that way, but he has a point. “I guess. I’ll tell you John’s story, then perhaps you’ll understand. Or maybe I will? John is his real name, by the way, but it would be a perfect pseudonym.”

John was another guy I met in the early days of Tinder. We’d hooked up a few times: he had a small cock but he knew how to use it, and he encouraged me to explore my boundaries. I learned a lot from him. I wasn’t always comfortable with his kinks, but he’d always accept a hard no, so we had a lot of fun.

One time he messaged me to arrange a date, and when I said yes, he asked if I’d wear something special for him. ‘Special’ turned out to be a crop top, a miniskirt, my highest heels, and fishnet stockings. I had no problem with that, except I had to buy the fishnets.

Five minutes before he was due to arrive, he asked if he could pick me up outside the newsagents rather than come up to my flat, because he wanted to take me somewhere new. That sounded fishy, but John had sprung some interesting surprises on me before, so I went with it.

He was late. For twenty minutes, I had to stand at the end of the street, seriously underdressed for the weather, enduring the stares of passing drivers and wishing I’d worn something less eye-catching… and panties.

When he finally showed, he pulled up beside me and I tried to open the passenger door. It was locked.

He rolled down the window, and as I leaned in to give him a piece of my mind, he said, “How much, darlin’?”

That’s when realisation hit me: the cheeky bastard had got me to dress and act like a hooker, and I’d been daft enough to let him.

I had to smile, but I shook my head anyway. “I’m out of your price range, pal.”

He said, “Yeah, right. A cheap tart like you? I’m not paying more than twenty for your worn out pussy.”

Then he actually pulled two tenners out of his pocket and waved them at me.

I looked at them for a second, then thought, fuck it, why not? A little bit of roleplay might be exciting, and if he wanted to buy what he could have for free, at least I wouldn’t be out of pocket on the stockings.

“Okay, mister. But no kissing, no bareback, and I don’t do kinky stuff.”

He grinned, and unlocked the door. “Yeah, you do. But a quick suck’n’fuck will see me right.”

I got in and asked him where we were going. He said there was a car park on Church Lane which was unlit, always empty in the evening, and backed onto the woods.

That was the new place he wanted to take me to. I gave him the side-eye, but to be fair, blowing him in a car park did suit the game we were playing.

Except he couldn’t wait that long. As soon as we turned onto the quiet roads, he unzipped, whipped his cock out, and said, “Might as well put your mouth to work, darlin’. Just don’t make me cum. I paid for a fuck too, and I want my money’s worth.”

This was supposed to be a date, so I had a condom in my bag. I rolled it on and got to work.

I always loved sucking John’s cock. Back then, I didn’t have the throat skills I do now, but I didn’t need them: he was small enough that I could have gone deep without gagging, and he didn’t want that anyway. He preferred to lie back and leave me in control, and I liked to worship his knob with my tongue, teasing out moans and groans with each sharp flick and lingering lick.

Except I wasn’t me, I was some cheap whore he’d picked up off the street who’d been told not to finish the job. That was the game he chose, so that’s what he got: a bored, business-like BJ, just my lips around his shaft and my head bobbing up and down in a desultory rhythm.

I wasn’t enjoying it like I usually did, and I don’t imagine it was doing great things for him, but something about that scenario got my clit pulsing. Maybe it was the semi-public location — knowing anyone we drove past might see what I was doing — or maybe it was flirting with the taboo of sex work. I had no idea, I just knew that when he parked I was going to ride him, and there would be nothing desultory about that. He’d get his twenty quid’s worth, and then some.

The car park was deserted, like he promised. He pulled up in the darkest corner, close to the trees, but then he switched the damn courtesy light on. I figured we were far enough from the road that anyone passing wouldn’t see more than a vague flash of pink, so I took my top off.

He slid his seat back, reclined it a little, and patted his cock. “Hop on then, love. You’d better make me cum this time, or I want my money back.”

I’ve fucked on the back seats of cars loads of times, and it is always uncomfortable. But that has nothing on trying to mount a guy up front while wearing stripper heels.

I ditched my shoes, hiked my skirt up, straddled John, and reached down to adjust his cock for the perfect angle. By the time I sank onto him, I’d lost count of how often I’d banged an elbow, or a shin, or my fucking head on the roof, and I was rapidly losing the mood.

But once I had that familiar cock inside me, it was all good; I wanted what I knew he could give me. I clenched around him, and asked “So, how’s my worn out pussy? Worth twenty quid?”

I think John had abandoned his game the moment he felt my warm grip. “It’s worth a fucking fortune, Tori. Don’t ever go on the game, I couldn’t afford you.”

“I’d give you a discount, babe. Ten percent off for every orgasm.”

I wasn’t certain he would earn a discount that night, not with how awkwardly I was positioned. John couldn’t go deep at the best of times, but I’d never needed him to, and once I started rolling my hips, grinding on him, I could see satisfaction in my future. And when he reached up to play with my nipples, rolling and tugging in time with my tempo, I knew an orgasm was on the cards.

I was teetering on the brink of that orgasm when I saw something that stopped me in my tracks. There was a bloke standing in the trees, staring at us. He had his cock in his hand, wanking like a demented monkey.

John asked what was up, and he laughed when I told him. “He’s harmless. This is a popular dogging spot, so he’ll just watch unless you want more. I can turn the light off if you’re uncomfortable.”

I wasn’t uncomfortable, not when I knew what was happening and understood I was safe. Watching a man masturbate, knowing he’s thinking about what he wants to do to me, is one of my kinks, so I got back to business.

Business didn’t take long. I couldn’t tear my eyes away from that stranger’s cock, and watching him send jets of milky jizz in my direction was enough to tip me over the edge into orgasm. Luckily, my cunt spasming around John’s cock was enough to finish him off, so as well as having something like a three-way simultaneous orgasm, I got to keep that twenty quid.

John told me afterwards I could have beckoned the other guy closer for a better view, and we could even have asked him to join in.

I said, “Maybe another time.”

Doctor Bonner is giving me his ‘concerned but in a sympathetic, non-judgmental way’ expression. “I see. And was there another time?”

I’ve spent nearly two hours telling this man about my sex life, and he still doesn’t know me. “There were loads of times. Watching men cum is hot, but it’s so much hotter if it happens when another man is cumming inside me. John stopped taking me dogging though, after the first time I invited a guy over to the car. I gave him a handjob through the window, and it turned out John wasn’t so keen on seeing men cum. Not when spunk landed on him.”

The doc smirks, but quickly buries it under his concerned frown. “John seems a trifle manipulative. I don’t judge people’s kinks, but I believe they ought to be discussed with partners and agreed upon. You were tricked into scenarios you might not have chosen.”

“No, Doc. I chose scenarios I might not have considered if John hadn’t put them in front of me. And I had fun.”

Another by Marsha Adams

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