Chaperoning Matthew

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As she knelt up on the bed to the side of where I lay, I held the protruding end of the dildo which had the harness dangling over its middle, to stop it sliding out of her cunt while she did up buckles behind her and then to her far side. Then two on my side, and suddenly it was all held in place: she looked, in the dim light, exactly like a woman with a cock. A wild Amazon, penis in proportion...

"Karina. Take that lube and get Steve ready. Even if he is pissed enough not to mind without. Twat."

Matthew spoke without malice, and we all knew Steve drank rather too much. Gail had been a good influence, meaning he didn't go on benders alone any more, but we did still worry. He'd been beaten up enough times. I figured his booze issues weren't my problem, and his failing to be able to fuck any of us might be the lesson he needed. I squirted lubricant over two fingers, pulled him across my lap, fondled him a bit with my palm, and jabbed both fingers at once into his arsehole. It took some initial force, but then he relaxed and moaned happily, chin propped up on his hands.

"That's right. He loves that. Such a filthy bum boy, aren't you, Steve?"

"Mm-hm," Steve agreed, gleefully, as I bent my fingers and knuckled him.

"You want her cock, don't you? Just gagging to get fucked up the arse, aren't you? So queer, you don't even care if it's a real bloke or not if they can just fuck you... That big, thick cock, pushing into your hole..."

"Takes one to know one!" Steve sang out both tunelessly and tactlessly. I don't know who slapped him first out of me and Gail, but we both made red handprints on his arse. Mine wasn't as good - I'd had to use my left hand, what with the right being occupied.

Luckily Matthew was relaxed enough by now to find Steve's comment hilarious, and retorted, "Yeah, and I also get off on watching blokes get fucked, so that's what's going to happen. Go for it, Gail!"

She pulled Steve off me, and shoved his knees under him so he was on all fours, resting on his forearms, arse in the air. I snuggled back next to Matthew to get the full side-on view, of this beautiful lad all naked, dishevelled, and totally desperate to be fucked. And Gail approaching him from behind, kneeling up, huge mane of black wavy hair swept back by her hand and not yet falling forward, her neat breasts jutting out perfectly for me to admire them, and her large dark brown cock, all wriggles and bumps, sticking out even further, finally touching Steve's crack as he awaited her, bent forward to take it.

Gail grabbed the lube bottle, starting to drip on the bedding, and squirted it all along her dick like mustard on a hot dog. She smeared her palm along to spread the lube out, jerked herself up and down a few times - I had no idea if she would feel the benefit of that from the other end, but it looked as if she might - and leant forward, her cock forced right into Steve's hole as she walked each knee forward and thrust further into him.

Steve moaned loudly. That bit where it hurts and the pleasure hasn't kicked in yet, I guessed. "No screaming," she told him with another slap on his bottom. "Actually, if you can't do anything useful with your cock tonight, the least you can do is make your mouth useful." With nudges of her knees and whacks on his arse, she made him turn 90 degrees, towards me. "Lie back on the pillows, Karina. Open your legs so he can get his face in there. He's getting the hang of it, but he needs more practice."

This was Gail's order, but Matthew was staring at Steve's arsehole stretched by the thick plastic cock, stroking his own up and down, mesmerised.

With a bit of wriggling and an extra pillow, I got myself comfortable on my back, my cunt open and right under Steve's face. And he was good, which was quite a feat given his wife's cock banging him hard at the same time. His arms round my thighs kept us together, his mouth to my cunt, and he could suck and lick exactly where I needed it. I wanted more and more, but at that time of night I couldn't be bothered to say anything - just letting him keep going, slurping happily over my clit, was fine by me.

Gail reached her hand round to Steve's cock, which was showing some glimmerings of life, she told us - I couldn't see and wasn't going to move to look.

"No." Matthew spoke sharply. "Don't just try to get him hard by rubbing. He needs CBT. Hurt him. Pull it and pinch it and scratch him. Squeeze his balls till they crunch. Actually..."

Matthew slid off the bed to rummage in Steve and Gail's suitcase, where Gail's cock had been. Steve tried to turn his head but I hung onto his lovely hair and wouldn't let him. I wasn't letting him go. That mouth was staying put, if I had any say in anything at all!

He managed to bend an arm underneath himself, reaching his hand forward under his chin and then two fingers pushed into my dripping wet cunt.

Oh, yes. Payback was good, I felt.

"Here you go," Matthew said cheerfully, standing over us. "I thought he wore this all the time. I would highly recommend it; it makes him much more well behaved."

Gail chuckled, and wobbled Steve as she took the item from Matt and then lifted both hands from the bed so as to fasten straps round Steve's cock and balls by feel. Matthew watched and told her when she'd got a bit twisted, but didn't touch any of us. I got the impression he was slightly enjoying not being able to touch. It made the looking all the more fun.

"I don't need him well behaved all the time. Though you're right, sometimes it is sure handy!" I guessed she started rubbing him up and down again, as Steve groaned. In fact, as she thrusted in and out of his arse, playing with his cock so that it tried to get hard but couldn't, now because of the tight straps, not from brewer's droop, he was groaning more and more. He couldn't control his mouth any more so I just tried to hang onto his head with my thighs to muffle the screams when they came.

And then there were screams and groans and, when he came and spurted come into the counterpane, a thick rope of white goo. His grunts were replaced by an agonised whimper of pain, then a moan of satisfaction.

Gail held still for a moment, then fucked him as hard as her tired body could, as he collapsed under her, panting and whining. She sat back, exhaled, and came to lean back next to me. I let my legs go floppy and Steve came up for a deep breath, face red and sticky. He collapsed on his back at our feet, near the bottom of the bed.

We all looked at Matthew, who was flushed in the face, jaw rigid, about to reach his own orgasm. He gasped, "Karina! Want - to - see - you - come! Gail - can you?"

And when Gail smiled and slid fingers inside me and lowered her lips to my clit, Matthew ejaculated with a cry. As Gail's third finger stretched me and bent, thumb pushing my clit hood aside, little finger straying not-uncomfortably into my arse-crack, I exhaled, letting myself relax and enjoy the feelings of pure pleasure. Gail was regarding me possessively, another fun toy.

It was when I cast my eyes round to the chaps that I really realised the reality of the filthy situation - Steve was lying on his side, holding his eyes open so he could watch Gail - his wife, even, which somehow made it more dirty - going down on me. He caught my eye and gave me a slow, sleepy, sleazy grin. I concentrated on avoiding coming too soon - I didn't want this to end, but then I saw Matthew's face. Any slight sadness was drowning under his lustful gaze, getting a kick from his position of power, and as he came, he was staring right into my eyes. He still wanted me, my body, and groaned as the thought made his balls clench all the more. With all that around me, my body decided it was time to ignore any input from my brain and take off itself, shuddering, squeezing, and I began to scream, leading to Gail hastily putting her spare hand over my mouth - salt and cinnamon, she tasted of - and Steve dragging himself onto my legs to help hold them still.

Thus held down, I bucked and twisted but without much energy, and I whimpered as more, smaller climaxes bumped through me, and more, and more, until I finally collapsed, still, and Gail lifted herself of my sticky, sweating body, wiping her hands on the increasingly-damp sheets.

I felt a bit bad that Gail hadn't come, but when I mentioned the point some time later when I'd got the breath, she assured me that that wasn't what it was all about. Steve would help her sort that out the next day, she said, and in the meantime - she pulled me down to lie next to her and we practiced some rather good kissing if I say so myself, slow, deep, and increasingly sleepy, breasts rolling over breasts, my soft, smooth thighs rubbing against hers. We slowed down and lay quietly, my mouth round one of her nipples, nuzzling it gently. It was gently erotic, which was all we could cope with by that point.

Matthew broke the silence. "It's a wrap." He got some slow, quiet chuckles in response. "I would go for Scene Two - maybe tie up Karina and you two do pain and pleasure until she screams - but somehow I think she's just falling asleep. Right, petal?"

His pet name for me turned me on again despite my exhaustion. I applied my brain to the words he'd just said.

"Right, boss. So we'll have to do that another time, once you're a free man and can be a more hands-on film director."

Gail murmured agreement. "And when Steve's cock works again. Keep the director happy."

Steve said nothing. He was already asleep. Matthew threw a sheet over him, and the three of us crawled under the duvet, and we all made like logs until Steve's alarm went off way too early.

I'd vaguely noticed Steve get up, but only awoke properly when there was loud knocking on the door. "Room service!"

Gail leapt to the door, remembered in time to don a fluffy white dressing gown provided on the door for the purpose, and wheeled inside a trolley of fruit, scrambled egg and smoked salmon, most-welcome coffee and a mountain of rolls and pastries. "Wow, man, look at all this! Come, sit, Steve!"

Steve finished his ostentatious tie knot and added his suit jacket. I'd not seen him in normal trousers since he was a teenager, and certainly never in anything this smart, so well-fitted. He combed his fair hair back with gel on his fingers, and looked like a model, complete with hangover. "I can't. Need to be there for nine. It's a cryin' shame, believe you me."

He wasn't just speaking about the breakfast. At least I could have some of the food before I had to run.

Gail forced him to down some coffee and take a couple plain rolls with him, and on his way to the door he toed Matthew's naked body clear of the duvet. Steve looked at him from top to toe, fringe flopping over his face. "Good luck, mate," he said. Before he and his hangover left, he called to me, "Stay in touch, yeah?"

We did.

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3 Comments
RangeExpanderRangeExpanderabout 3 years ago

Your style is so direct, down to earth - I just love it! You sound like such a normal horny human being. I love sharing your explorations, and your willingness to just go for it in all kinds of different combinations. You always manage to see the sexy side of things. Thank you

AnonymousAnonymousalmost 4 years ago
So nice

Your stories always feel real and about just like the kind of sex I like to have.

WhiteNekoWhiteNekoabout 4 years ago
You where right.

I really liked it. I'm 100% convinced that European English is fucking with my American brain but besides that it was a nice wholesome story tha reallyt got my engine running. Thank you for writing it.

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