Chaperoning Matthew

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Oh, are the ladies free?" Matthew asked.

The huge squat bloke making a mockery of smart black-tie looked up at him, then at us, surprised. "No. They're not coming in."

"We are, actually." Gail's voice was remarkably assertive.

"No, you ain't. You wouldn't like it."

"Actually, I'm pretty sure we both would, unless those pics are all false advertising." I thought that was a clincher.

"Wasn't saying you ain't a dyke, love. You wouldn't like the staff inside, throwing you out, forceful like. The ladies on stage, they don't like being looked at by women, so no women coming in, geddit?"

We got that we weren't coming in, though I'm pretty sure none of us comprehended why strippers cared whether it was men or women looking at them.

"Try the Raymond Revue Bar. They let anyone in." I think he didn't intend that to be quite so insulting as he sounded.

"Where's that?" Gail asked me. It's one of the biggest neon landmarks in the area, so I led them round a couple corners and there it was, clearly more upmarket, at the end of its own alley, looking more like the entrance to a casino.

Steve went ahead again, almost without any support to keep him vertical. "Four, please."

The bouncer counted, looked mildly surprised at me and Gail, "Don't get many ladies in here, off-stage I mean. Fifty each, so that's two hundred, please."

Steve was reaching into his pocket for a wallet and credit card, as Matthew stepped back gasping in horror while Gail shrieked, "How much? No way!"

He fumbled getting the card out, and mumbled something like "It'll be fine. Fiiine!", when Gail slapped him across the face and apologised to the bouncer. Matthew and I helped her drag Steve back out of the alleyway to the street, him kicking and shouting abuse at us.

"Fucking tightwads! Right, I'm going in here to find something to watch!" He tore himself away from us and hurled himself into the adjacent sex shop, then ran down into the basement, where the explicit stuff would be.

I'd been in some sex shops, half of them window- shopping with Matthew in fact (well, we'd had to go inside seeing as no windows, but you get my drift - lots of inspiration gained from magazine covers and ensuing visits to DIY stores, but no purchases of overpriced filth. Students, remember?) But this one was a bit different - besides the aisles of video cases and magazines, and the displays of 'clothing' - if you can call sets of straps and buckles that - and 'accessories', there were white chipboard booths at the side, containing large TV screens. Well, a couple also had small strategic holes in the wall, but we didn't go in those ones.

By the time we'd got down the stairs, Steve was waving a video case at the assistant and asking to watch it. Some pound coins changed hands - Gail sighed in relief at the much smaller cost - and Steve was gesturing us to follow him.

"Come on, it'll start!"

We all squeezed into the seat in the four-by-three melamine cubicle - easy to wipe clean, I supposed. Steve was sat across my and Gail's laps. I wondered what the film would show. What would be Steve's taste in porn?

The video started, and showed slim men in scanty leather - there were blow jobs, lots of chains and bondage, some beating, some penetration. It was pretty well done, especially compared to mainstream porn with women.

I enjoyed it a lot - relevant to my interests and I was drunk, remember - but part of the charm was Gail on my right reaching round and fondling Steve's crotch, opening his trousers, while Steve's head fell back next to mine and I could feel his warm skin, and inhale that wonderful scent of another human close enough to fuck.

On my left, Matthew had failed to extract his right hand from where it was crammed between me and Steve, so had managed to open his fly with his left and was stroking his long, slender cock with it. It still looked good.

"Still gorgeous, love," Steve commented lecherously from his vantage point above us. I murmured agreement.

"Yup. Not for you, though." Matthew was more brusque than usual.

"Mine." Gail confirmed, holding Steve's cock passively.

"Sorry," Matthew said to me, for reasons unknown.

Both men were stiff and starting to clench in a run-up to orgasm, when the film cut out and the light went on more brightly. Gail pushed Steve off her so she could get up. He and Matthew both lost the moment and reluctantly did up their flies, still semi-hard underneath.

"Right, I'm having this one," Steve grumbled, waving the video case wildly across the shop aisle. "And this one, and this, and how about this one for you, love? And this. For you, Karina?"

I picked out a magazine, and another when Steve told me to. So did Matthew. Steve grabbed a couple more. Between us, we'd got most of queer sex and consensual kinks covered. Gail helped him carry the pile to the counter, nodding agreement to it all. It was probably still under half the price of the strip club. I did wonder if it was going on Steve's expenses.

"Sure you want video, not DVD, sir, ma'am?"

"Our hotel's only got VHS," Gail explained politely. Her giggling made clear she was still drunk. "Only got VHS at home, too."

"At least it's not Betamax!" Steve added, which I found hilarious given I'd grown up with Betamax for a good decade longer than sensible, and the dodgy petrol station which rented Betamax videos - the only place that still did - was half blurry horror and half grainy porn.

"One moment." The assistant returned to the middle-aged man before us in the queue. "Are you having them, or not?"

"I'm just saying," the man whinged, "last month it was only two pound for poppers, and now you're charging ten, and it's plain robbery!"

"Yeah, but last month they was legal. Poppers is illegal now, so price goes up, innit?"

The customer argued that if a shop was still selling leftover stock, it should be the same price or even discounted, everyone knew that. The assistant failed to get across that it was nothing to do with leftover stock, more was on order in fact, but everything to do with the fact that he was breaking the law while selling it. Eventually Steve interrupted. "You got another bottle?"

The assistant put another on the counter, wordlessly.

"Right, I'm buying both these. Now, here you go, and piss off."

The customer glanced at the small bottle pushed into his hand, confused.

"You heard him. Present for you; now fuck off." And, still grumbling, off the man fucked.

Our shopping, possibly with generous bulk discounts if I'd been sober enough to calculate, was rung up and put into a couple discreet plain bags with newspaper covering the merchandise, which in retrospect probably looked more dodgy, as who else uses non-logo bags? Oh, the Italian which had bagged our booze. I could look forward to some more of that, now. We staggered upstairs into the night.

"You're coming back with us, for drinks." It was a statement from Gail, not a question.

I guided us to the Tube - Matthew desperately pleaded with Steve not to open any of the plastic-wrapped magazines on the train - and to Kensington, where Gail then took the lead to the very smart, modern hotel where porters in black-and-gold hailed cabs and nodded to us.

I was rather intimidated by the grandeur, but as the doorman assisted a very drunk woman, quite likely a prostitute given her clothes, calmly into a cab, and greeted a suited man who responded by puking over an ornamental hedge, I relaxed.

"We should sit in the bar," Gail suggested. "They'll still be serving."

"Nah! Up to the room, immediately!" Steve retorted.

I had to agree with Steve. I hadn't forgotten my promise to Matthew, but I did want to see at least one of those videos. And we had plenty to drink with us already. Matt didn't look like he was likely to be shagging anyone anyway; I'd be impressed if he didn't fall asleep. It was pushing midnight; we'd never get home tonight.

We got in the lift; thankfully the bellhop only called the lift for us and didn't come inside, as Gail thought that the lift was an excellent place to push up against me and run her hands up and down my body. I wasn't objecting and tried to sound encouraging as she rubbed up my thighs, my chest, and down my breasts, all very pleasant, though it would be easier if I didn't have to stand up. I doubted Steve would mind, if he noticed at all.

We shuffled down the thickly-carpeted corridor and entered the totally bland, albeit luxurious, business hotel room. Matthew immediately spent quite a while in the bathroom, releasing that tension from earlier, I guessed, while Steve hamfistedly figured out how the video worked and Gail poured out tumblers of wine for all of us.

We all ended up sitting up on the king-size bed, again with me in the middle with Gail and Steve tangled on one side, Matthew safely on the other.

The film we'd been watching earlier was steamy, but the more so because we knew what would happen in the first twenty minutes, and various aspects appealed significantly to each of us. Starting with Steve and Gail, clothes were shed, and soon all of us were playing with ourselves casually as we continued chatting about anything and everything, having another drink, all totally relaxed. It was odd, though, as while Steve and Gail were stroking each other, Matt and I were carefully keeping our hands to ourselves, as it were.

Steve was naked, the rest of us had underpants on. I'd missed the moment when Gail's bra had vanished, but suddenly, those breasts, more than a handful each of perfect pleasure, their flesh wobbling ever so slightly as she moved, shimmering in the dim light from the telly... Though as the film reached its climax along with the protagonists, none of us could pretend we weren't focused on watching a cute chap being enthusiastically fucked and screaming his enjoyment. Inspired, Steve grabbed the poppers, defeated the child-proof seal, had a good snort, and lay prone across the bed - Matt and I had to pull up our legs - so Gail could reach her fingers inside him. Matthew and I watched, spellbound, the film forgotten; now we had real life theatre, starring a perfect body, in front of us to look at, him purring as Gail moved her hand in between his legs.

"Regrets?" Steve asked Matt, lifting his head from his forearms and raising an eyebrow coquettishly. "It could be you here."

Matthew didn't say anything for a minute. He'd always been a man of few words - one reason we split up. He watched that pert little arse, squirming from side to side, that golden naked body, seeing Steve impale himself on the ends of Gail's fingers, wantonly, desperately, not quite managing to come. I nearly did, though, watching the filthy boy writhe...

"You're too pissed," Gail concluded after we'd spent a good ten minutes watching, withdrawing her hand as Matthew finally replied,

"No regrets. Just - nostalgia." He smiled. "Still a beautiful arse."

"I could say the same to you," Steve said, snuggling up to Matthew. "Would love to fuck you one more time? You ain't married, yet. And we know they'd love to watch," - he indicated me and Gail with a circling of his head - "if they weren't too busy with each other." I shrugged. It was all true. "Come on. You know how much you love it up your arse. I'm even better than any pegging!"

Matthew didn't answer immediately. I realised, despite the drink, that this was my cue:

"What would Kathy say?"

"A lot, probably." He sighed, his worries suddenly visibly pushing his shoulders downwards. The silence became oppressive. A minute passed, and finally, he spoke. "I'm going to have to tell her, aren't I? That I can't. I can't do it."

One of us asked, "Do what?"

"Marry her." Matthew deflated even more. "Be the man she wants me to be."

"What, exactly, is the problem?" That was me, blunter than ever when shitfaced. I've always been better at investigation than tact, but this time Matt didn't seem to mind.

"Be a proper bloke, rogering her properly."

I must have looked nonplussed, given how he'd had no problems at all providing me with a damn good rogering. Frequently. He'd never mentioned impotence becoming a problem...?

"No, no, not that. Fully-functioning dick. No. Me, not wanting stuff she can't give. I make her happy, why can't I be satisfied with her?"

Steve roused himself from his drunken stupor, tilting his head from his position face-down on the bed, and queried, slurring, "Thought you'd decided you were fine with pegging, didn't need a bloke's cock to be doing it?"

Matthew's face went beetroot. I nodded, understanding, and Gail went "Aaah", while Matthew tried to sound matter-of-fact as he replied, choking the words out, "Would be. If she were into it. Which... she isn't. Just isn't," he repeated, dully.

"You said you'd done it, it was great, you said?" Steve jabbed a finger at Matthew, accusingly.

"Oh, we did. It was. I thought. Only, turns out she doesn't like it after all, not just it doesn't do owt for her which is fair enough, but what it is, is she really hates the idea of me not being a proper man, all masterful, on top, strong and silent type... Doesn't want to have to think of me differently... "

Given Matthew had managed to be plenty masterful when required during our relationship, and the main reason we'd split up was he was too taciturn and silent, basically couldn't recognise an emotion if it hit him in the face, I reacted strongly to this. "Is the girl mad?"

Matthew shrugged, no words left in him, and Steve answered instead, harshly, his voice gravelly from the booze. "Nah. Just righteously homophobic. Anything in bed that reminds her that blokes don't have to stick to women and cock-in-cunt sex, let alone might bring yours truly to mind, it's going to repulse her." He spat, bitterly. "Her loss."

Thinking about this for a minute, I realised Steve was right. I'd appreciated Matthew's imagination in bed, with penis-in-vagina sex only a small part of his interests, and the fact that he didn't feel constrained to behave in 'manly' fashion appealed to me. Personally I thought his empathy for someone being penetrated was a good thing! And knowing that he was choosing to be with me, despite being able to get a bloke any time he wanted one - "seriously, you think Cindies is a meat market? Back room of the Dun Cow, look left and right and get a nod, and it's blow-jobs a-go-go in the toilets a minute later!" - I found that really quite reassuring.

But for other women, his open mind just brought up jealousy, fear, and things they didn't want to think about. Daft bints! I wanted to go out and advertise Matthew to the world as a damn good shag, poor love.

"Definitely her loss," I agreed. "Turning down fantastic sex just because she can't handle anything unusual. Mad."

"Matt, hon, it's OK. It's not you being wrong. It's like with Karina, the two of you just aren't compatible." Gail spoke sense, calm and neutral.

"So... we need to find Matt someone with my enthusiasm for all kinds of sex, and Kathy's patience and stability and liking nature and country walks and all that. Erm... Steve?"

I'd meant it as a chance for Steve to contribute - he knew all the people they'd both grown up with - but he and the others all took it as a suggestion, and laughed.

"Moi? Stable?"

"Been there, done that, no thanks," was Matthew's deadpan comment.

"Not sharing! Well, not for a major relationship-like thing, which I'm guessing you want, still? Friends with benefits I'm perfectly happy about, as you well know if you do want Steve again." Gail summed up that idea.

Matthew looked thoughtful, then sad again. "Shit. You guys are right - it's just never going to work with her, is it? Either I spend the rest of my life unhappy, or I cheat and then I'd be unhappy anyway." Another, unbearably heavy pause, as we all willed Matthew to figure out another option.

Finally, in a voice quieter than I'd ever heard, "Or - I go home and call it off." I thought I spotted moisture in his eye.

There was a breath, then a long, slow sigh. "At least we haven't paid for the reception venue yet." He took another deep breath, realised he'd come to a decision. "Mum'll be gutted."

"Not as gutted as she'd be if she knew number two son was unhappy about being married," I snapped back. His mum was incredibly practical and protective of her family. Great woman. I'd actually missed his parents more than him when we'd split up.

Matt nodded and reached for the wine to pour himself another glass. "Yeah. Or if she thought I'd be cheating on my wife." He downed the glass, refilled it and knocked back half again. "I don't cheat on my about-to-be-ex fiancée either, but don't let me stop you guys."

It took us a minute to parse the implications of that. Steve had clearly had Matthew-related plans for the night, but wasn't going to look a gift woman in the mouth, as it were. I wasn't going to turn down either of them. And Matt would be there, watching...

Gail and Steve blinked at him, then gazed at me, mirror images, each raising a questioning eyebrow at me. I nodded, not having any guilt to deal with. I had a sort-of partner - OK, a bloke I was shagging reasonably frequently - and a few other people, less frequently; there's only so many hours in a day - but we'd never seen the point of monogamy - in fact pushing cute women at me was more his style. He'd approve of Gail...

I figured I just wanted to reassure myself that Matthew wouldn't feel left out. I cared for him - we all did - and he was having to wrestle with a huge emotional decision, which he'd never been at all good at dealing with.

"Seriously? You'd be OK with us... doing stuff, and you just watching?"

The side of his mouth twitched subtly, in a way I still found endearing. "Depends what I'm going to be watching, doesn't it?" I decided the signature dry humour was a good sign of him coping.

"We take requests," Steve confirmed. "You're the director, you've got your actors, what's your pleasure, mister?"

And suddenly, the atmosphere in the room was re-set. Matthew in charge of all our performances, yes, that was a scenario to get my cunt throbbing in anticipation...

Matthew's whole mouth was grinning now. "Your pleasure is my pleasure, I think. Quite literally. Take it away, Gail. Um - Karina? He's well up for it if you are. Trust me, I've heard a lot about what he'd like you to do to him and vice versa... Filthy boy, he is... "

"Shit! That was a confidential conversation, you bastard!" Steve yelled, sitting up, and Matt grinned, all guilt suddenly gone.

"Whoops. I'm drunk." he replied sarcastically. "The jury must ignore that statement."

I shrugged. "If I must. If you don't want me to touch you like this," - I reached over and ran my hand down Steve's pronounced cheekbone, his neck, then down to his nipple, and gently pinched the one that wasn't pierced - "then do say, won't you?"

He didn't say anything. Probably because Gail was straddling his knees, bending in half and sucking his cock, squeezing the base with one hand to try to coax some life into it. He looked very happy, even as I pulled both his nipples and he gasped.

"Pinch them both, hard. He loves it, the slutty boy." Matthew's voice was deep and aroused behind me. I did as suggested and Steve moaned, reaching for me and managing to kiss me deeply. It was a good kiss, not too wet, and I could taste the booze on his tongue. We rolled over as Gail gave up on coaxing his cock into life, so I got to lie on my back, him warm on top of me, and to squeeze his bum in both hands. It was adorable.

Matthew spoke again. "Gail. You like pegging him, don't you? Show me."

Gail grinned. "Oh, yeah!" She peeled herself off the bed and went to rummage in her suitcase. Returning with a leather harness and a double-ended dildo, she started buckling straps around herself. "Karina, can you hold this for me?"