Playing Away Anal Literotica.com

Playing Away

© Bad Hobbit 2024

“OW! Shit! Stop! It hurts!”

“Baby, just relax.”

“RELAX? Fuck, how am I supposed to relax when you’re OW! when you’re trying to shove that somewhere it was never meant to go? You told me it wouldn’t hurt!”

“Look, I promise that, once it’s in, it’ll feel good. Just push out. Like you’re having a shit.”

“Oh, very romantic! OUCH! Please please stop.”

“Just be patient, baby. Grit your teeth, push out, and it’ll soon feel better.”

In truth, I didn’t have a choice. He was lying on top of me, and it would have been virtually impossible for me to get out. It wasn’t that his cock was particularly long or thick I’d guess not much more than six inches, and my hand went around the shaft but the knob on the end seemed out of proportion. It had felt sublime, rubbing insistently on my Gspot, barely thirty minutes earlier, as he’d brought me to my second orgasm of the evening. But now he was trying to force it through my virgin anal sphincter, and that was a different matter.

I mean, it wasn’t as if I hadn’t been asking for it. It was the last night of a threeday conference. I’d been working on one of the exhibition stands, but I’d managed to get away to see some of the presentations. Simon’s was one of the best. He was relaxed, made his key points well and answered all the questions succinctly and fully. And he absolutely oozed charisma.

So I made sure that, on the last night, I flirted with him over dinner. I’d had a real stroke of luck; a guy came onto our stand and started enquiring about jobs with my company. I took his details and, when I checked later, I found that he was meant to be seated at the same table as Simon. I called his mobile and asked if he’d like to swap with me so he could get to know my colleagues, and he seemed very grateful. But not as grateful as I was.

I put a lot of effort into getting Simon’s attention. I arrived at the table early and rearranged the seating labels so I was sitting opposite him. My dress was rather low cut, and my breasts are good, even if I say it myself, so whenever I bent forward, he had a great view down my cleavage. The skirt was very short and the heels possibly rather too high. The makeup was perhaps slightly too heavy. And adding a black leather choker was maybe a bit too much.

But it worked; he certainly noticed me. I complimented him on his presentation and tried to ask intelligent, businessrelated questions at least at first. He was wearing a wedding ring, but that didn’t put me off. I’ve fucked a few married men, and they’re often better than single guys. And anyway, at a conference, anyone is fair game.

We chatted, and ate, and I drank quite a lot of wine. The afterdinner speaker was entertaining, and then a band started playing. I wasn’t sure whether he’d ask me to dance, but I needed a pee first. In the ladies, I realised I was quite wet from looking at him; his strong, square jaw, his broad shoulders and his piercing blue eyes. I’d worn cheeky black lace thong panties, but on an impulse, I slipped them into my handbag, cleaned up with a wet wipe, then adjusted my makeup and headed back out.

He was standing waiting? near the door. He looked quite imposing in his expensive, nicelytailored suit. He smiled at me.

“Do you want to go back to the table? Or should we head off somewhere more private?” His look seemed to say ‘I know your little game and I’m up for playing it.’

The lift was quite crowded. We were at the back, and I felt his hand slide down and gently squeeze my bum. Excellent! He’d definitely got the message.

We went to his room. It’s a rule I have; if I invite someone back to mine, it could be hard to throw them out, but if it’s his place I can always make a run for it if I have to. Not that I’ve ever needed to.

He didn’t say much. I mean, what was there to say? ‘Do you want to fuck?’ was an option for either of us but, instead, we kinda said it with our eyes. And the answer for both of us seemed to be ‘YES!’

He held the door open for me, closed it behind us and immediately threw his arms around me. He was at least six inches taller than me, so my head went back as he bent over to kiss me. I could smell his expensive cologne, feel the strength of his body. It felt good.

Moments later, I was pulling his suit jacket off his shoulders and unfastening his tie, our lips still joined. Yes, he was a very good kisser; just enough tongue, soft lips, no slobber. He pulled the shoulder straps of my dress down my arms as I tried to unfasten his belt. We both knew where this was going, even though we’d not said it out loud.

He helped me unbutton his shirt, and the chest and shoulders underneath didn’t disappoint. But then he was cupping my breasts, palming and occasionally tweaking the nipples. That tends to drive me wild.

And then we were on the bed, my dress pulled down to my waist, his trousers still on, and his mouth alternating between my nipples. As I was trying to unzip him, his hands moved to my thighs and slid up, under my skirt, until they found my pussy. I gasped.

He broke the kiss. “Well, well; who’s an adventurous young lady, then?”

I smiled back up at him. “You like?”

“Very much.”

“You lick?”

He grinned. And, pulling away from my attempts to get his trousers off, he lifted my skirt and trailed his tongue up my thigh, across my pussy lips and down the other side. Then back again. And then back again.

I opened my legs, and he licked slowly across and then along my slit. “Tasty,” he murmured from somewhere between my legs, before dipping the tip of his tongue into my drooling hole. Fuck, I was so wet, just anticipating this. And I got wetter and wetter as he explored my pussy with his mouth.

Usually, I like a lot of foreplay. I’m very skinsensitive, and I melt when a man teases me with his fingers or his tongue. One guy tied me up and used my makeup brushes on me. He got me so turned on that I started to come just seconds after he touched my pussy.

But the thought of Simon had already got me going and drooling very quickly and nicely, and he accelerated the process. He went on a voyage of exploration around my flooded valley. He circumnavigated my outer lips, then moved inward, his lips, tongue even his teeth probing and nibbling into every crevice. He rimmed my arse that makes me tingle all over and tonguefucked my fuckhole. He teased my neat little inner lips, making me moan and squirm, and then went for the ‘overload’ button; my clit. I came.

And kept coming, as his tongue fastened on my clit and kept on licking until I was bouncing off the bed and begging him to stop.

Because, right then, I just wanted raw, dirty . I wanted to be fucked. Hard.

“Fuck me. Fuck me now,” I breathed.

He smiled, pulled my crumpled dress down over my hips and opened the bedside drawer. His trousers and pants slid down and off, and he didn’t stop to gather them up. I looked at his cock in some bemusement. It wasn’t as big as I’d hoped. With his confident manner and my rather slutty approach, I guess I’d expected to be dominated, and it always helps if the guy doing the dominating has an extralarge cock. Simon’s wasn’t really above average in length or girth but, as I said, the large knob intrigued me. The condom he retrieved went on with what appeared to be practised skill, and he adjusted it to allow that big, bulbous head to offer its full profile.

And that was something I only fully appreciated after he’d moved between my spread legs, kissed me and then thrust most of his length into me in one go. I let out a kind of shriek.

“God, you’re so gorgeous when you’re being fucked,” he panted after he’d pulled back and thrust in several times. After the shock of that initial, brutal thrust, that big, bulbous cockhead started doing really interesting things to my Gspot. The ridge on the top rubbed it up the right way on every thrust and every withdrawal, giving me double the fun. And yes, I suppose there was the sense of him dominating me, with his fit, quite muscular body pressing down on me, his broad chest rubbing on my titties each time his hips drove than rod of flesh into me. I still had on my slutty heels, so I crossed my feet over behind his bum, being careful not to scratch him, and rode his cock, lifting my hips to meet his on every downward stroke, easing my thighs apart to swallow him, then squeezing more tightly to suck at him as he withdrew. And he was making me moan with pleasure.

“Mmm. So tight, Megan. I wish I could feel how wet you are. Do you like what I’m doing?”

“Oooh yes! OH! That’s that’s oh yes!” All I could do was moan incoherently because that big, knobby cockhead kept pounding my Gspot, both ways.

“Are you going to come for me, Megan?”

“Oh yes, yes. Harder, please. Harder!”

He increased the pace and the ferocity, stabbing his cock into me hard each time, rocking backwards as he withdrew, obviously realising and relishing what his cockhead was doing inside me. Then he lifted off me a little, resting on one extended arm and smiling down as his other hand settled over my pussy and his thumb rubbed my clit while he kept thrusting with the same intensity.

And after less than a minute of this, I came. Of course I did. A fit, powerful man between my legs, pounding my Gspot in a way few guys have managed to do, rubbing my clit and whispering things like ‘Your pussy is so tight’ and ‘You’re such a delicious, y slut, Megan. You’re a great fuck.’ Yes, I couldn’t have held back if I’d wanted to.

The orgasm went on for quite a while, and it was powerful. I was writhing around, moaning deliriously, and Simon kept thrusting and rubbing. Finally, he pulled out, still rubbing my clit. My mouth was wide open and I was still moaning when I realised he’d changed position, straddled my body and pushed the bulbous head of his cock now minus the condom between my lips. He hadn’t given me the option to say no, and now my mouth was rather full. I can’t say I’m a fan of the taste of spunk, but the guy had given me two orgasms so far, including the best shag I’d had in months, so I dutifully sucked, rubbed with my tongue and let him fuck my mouth for maybe half a minute before I felt and tasted the first spurts. It was weird and a little uncomfortable to have that oversized knob in my mouth, but I guess I felt that I owed it to him to do as he wanted. And, to be honest, it didn’t taste bad. A bit sticky and slightly bitter, but I’ve tasted much worse including my ex’s cooking!

Finally, he pulled out and rolled over onto the bed beside me, breathing heavily with his eyes closed. I looked at him and thought ‘Yeah, he’s pretty hot. And he knows how to fuck.’

Then his eyes opened, he smiled, rolled closer and kissed me. “You’re amazing, Megan. I don’t think I’ve ever fucked a woman as responsive as you.”

“Not even your wife?”

If I’d expected him to be fazed by this, he didn’t show it. “No, not even her. And I guess your husband doesn’t fuck you as well as I just did.”

“Husband?”

“When you take your rings off, they leave a paler mark and impression on your finger. If you were divorced and you’d taken them off some time ago, the mark would’ve faded, but it’s fresh, so I guess your rings are in your bedroom. Is that correct?”

“Oh, officer, you’ve got me bang to rights,” I said with a slight blush.

“And I was right to bang you you naughty little slut,” he replied with a smile. “So we’re both playing away. And the night’s still young. What next? Should I fuck your arse?”

“What? No! I don’t do anal.”

“Never? So your husband isn’t up for it?”

“He’s asked, but I’ve always refused.”

“Why?”

“I’m amazed you even have to ask. Because it’ll hurt, stupid!”

“I’m not stupid, and it doesn’t hurt. My wife loves it.”

“Well, go home and fuck her arse.”

“Perhaps I should, but she’s not as deliciously slutty as you are. I’m surprised you don’t want to try it. My wife orgasms from it every time and strongly.”

“Really?”

“Yes. Anal orgasms are the best. I’ve fucked several women up the arse, and all of them have said it beats having their cunt fucked every time.”

I tried to ignore the throwaway obscenity. I liked dirty talk, but I felt there were limits.

“Well, I don’t think that’s anything I’ll experience any time soon.”

“Really? I promise you it’ll feel good. If we prepare well, it won’t hurt, and you’ll come like never before. Let me tease you with my fingers first and see what you think. Then maybe a plug or vibrator while I tease your pussy again?”

He took some lube, an anal plug and a tapered vibrator out of the drawer. I looked on in surprise. “It seems like you’ve come prepared.”

“Yes. And if you’re properly prepared, I promise you’ll come,” he grinned back. “Turn over and I’ll show you what I mean.”

Reluctantly, I rolled onto my front and watched as he squeezed some lube onto his fingers.

“Pull your cheeks apart. I need to put plenty of lube in there.”

I reached behind me and did as he asked, and as he bent over me I felt the cold lube being dribbled and smeared around my arsehole. He paused, and then I felt a finger, covered in lube, slowly press into my bum. It felt weird but strangely erotic; a kind of taboo frisson. Then he pulled it out, poured on some more cold lube and, after a moment, slipped the finger back in.

And I guess he was right. Having his finger pushing into my bumhole, going deeper, swirling a little, pressing against the sides, pulling on the inside of my ring actually, that felt very y, and despite my misgivings, the sensations were turning me on. I could feel my pussy juicing up again.

Then he dribbled even more lube on and started to press a second finger inside. That was a bit uncomfortable at first, but then it started to feel good again. And then the naughty boy slipped a third finger in. At that point, I began to wonder. It was just on the ‘pleasure’ side of the pleasure/pain divide. When he pulled his fingers apart it became more borderline, as he dribbled still more lube between them. But then he curled them a bit more and stroked them around the inside of my ring and a little deeper, seemingly pushing the gallons of lube inside, and it was a bit like ‘Wow!’

Then he slid his other hand underneath me and started stroking my clit, and I thought “Oh, what the fuck!” I looked at him and he snuggled down beside me and kissed me as one hand stretched and teased my bum and the other stroked and teased my clit.

And then his fingers slipped out of my bum, and I let out a disappointed “Oh!”

“Wait a moment, Megan,” he said, reaching behind him. And the next thing I knew there was something hard and coated in cold lube the tapered vibrator being pushed into my sphincter. It slid in fairly easily, up to a point, and then I could feel the stretch again, but the buzzing of the toy set up some very interesting sensations inside my ring. Meanwhile, his other hand was doing amazing things to my clit.

He worked the vibrator in and out, pushing it a little deeper each time, and the buzzing sensation, which travelled down from my arsehole into the back of my pussy, felt good.

“Ready?” I felt him straddle my body. His hand left my pussy and he removed the vibrator. I heard the soft rip of a condom wrapper, and then a dribble of cold lube landed on my bum cheek, as he appeared to be applying even more to his (presumably) rubberclad cock.

“Uh!” was about all I could say. He’d been doing some seriously hot things below my waist. I was highly aroused, but I wanted him to keep on doing more of it.

And then I felt the big knob of his cock pressing against my sphincter.

“Relax, baby. I’ll be inside you before you know it.”

And that’s when it started to hurt. His cockhead was wider than the vibrator, wider than his fingers, and it hurt. It hurt. And that’s when I started to complain. But he persisted.

“Just push out. Your arsehole will open, I’ll be inside in just a moment and it’ll start to feel great.”

So, willing to do almost anything to stop the pain, I pushed out. I had visions of shitting all over his cock hardly the most erotic thing but then, suddenly, that big fat cockhead popped through my ring, which shrank back to hug his shaft.

He held still for a moment and then pulled back slightly. And suddenly, something that had hurt like crazy felt crazy. My ring wasn’t being stretched to an insane extent it just gripped a slimmerthanaverage shaft while that insanely big head pressed on the sensitive inside of my ring. And then his hand slid back around my hip and that clever finger started working overtime on my clit. And I thought ‘I’m a dirty slut with a cock up my arse!’ And about then, I began to realise that I might just be able to enjoy it.

“How’s it feeling now?” he asked, softly.

“Better,” I whispered back.

He tugged back a little, and the inside of my sphincter suddenly sparked with some weird but very erotic sensations. Before I could say anything, he pushed in, slowly, a couple of inches, and then pulled back again. I gasped. And then he did it again.

“Better?” he asked again.

“Ye yeah,” I gasped as he repeated the action. And then did it again, this time going a little deeper.

The feel of that big cockhead pushing up my arse was strange. Not unpleasant or painful but, at least initially, not particularly pleasant. Thankfully, his clever finger on my clit felt amazing as did his other hand as it reached under my chest and started palming a nipple.

He pressed his mouth up close to my ear. “What am I doing, Megan?”

I could feel his cock sliding up and down in my tight backpassage. The friction was well, it was starting to become actively enjoyable.

“You you’re you’re my arse.”

“That’s right, lovely Megan. I’m your arse.”

He kept the pace about the same but slowly increased the depth.

“Where’s my cock, Megan?”

“It’s it’s in my ARRRRRRSSSSE!” I yelped, as he suddenly pushed it another inch or so deeper.

“Yes, baby, it’s deep in your arse. Going deeper.”

And I let out a long low moan as he did just that. As I said, the sensations were weird not really like being pussyfucked, but there were still some interesting little sensations from my Gspot, as his downward angle created a sort of pressure wave as he compressed my vagina from behind. I wriggled a little to try to increase this.

And there was something about being fucked up the arse and knowing that I was being fucked up the arse the sheer dirty sluttiness of it that gave a very powerful thrill in itself, quite apart from the Gspot pressure and the stimulation of my clit and my nipple. The weird sensations were becoming increasingly pleasurable, thanks, at least in part, to the copious amounts of lube that he’d inserted first. If he hadn’t been able to slide smoothly in that ultratight tube, I guess it would’ve been excruciating.

Finally, I felt his abs press on the cheeks of my bum and realised he was about as deep as he could go. Weirdly, I pushed back, wriggling a little to increase the penetration.

“Fuck. I I’ve got all your cock up my arse!” I stammered. And then shrieked as he pulled back in one smooth movement and almost slammed the rim of his cockhead against the highly sensitive inside of my sphincter. And, at around the same speed, thrust back in.

“Yes, you have, Megan. All of my cock. Right up your tight, slutty arse. It feels amazing. I think we’re both going to come soon.”

Whether it was the sensations themselves or the realisation of what was happening to me that I had a cock with a big, bulbous knob, rhythmically, deeply and mercilessly my arse I was starting to get into this. I tried to curl my abs, Pilateslike, to see if I could increase the ripples that were transferring to my vagina and Gspot.

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