Anal At Last Ch. 05


[This story is one of a sequence I’ve written. You can read the other parts of the story for more details, but here is a summary;

I’ve recently divorced my wife, and am raising my son on my own. After a long abstinence, I’ve met a woman (Angela) and we’ve just had our first night together. She’s had her first orgasm in the missionary position, thanks to a little tip I’d picked up online. We’ve not yet had anal sex, but a little anal play has been involved….

The cast:

Me: 36 yrs male

My son: Daniel

My girlfriend: Angela, 40 yrs

The babysitter: Samantha, 18 yrs

Samantha’s dad: Bill

Samantha’s brother: David]


I slid up the bed so that I was laying on to top of her, my hard, hard cock lying between the cheeks of her ass. I rubbed it up and down a bit, feeling the moisture from her previous come and my rimming spread around my cock. Then I reached down and pushed it down, under the curve of her ass so that my head was touching the lips of her cunt.

“Fuck me, fuck me now,” Angela moaned, and tilted her pelvis back to give me easier access. I rubbed my cock along her wet lips for a bit longer, and then pushed, feeling her cunt separate as my prick entered. God she was hot. I kept pushing all the way, until the cheeks of her ass touched the bottom of my stomach, at which point she ground against me. I pulled out almost all the way again, so my head was just parting her lips, and then pushed in again, harder this time. She grunted, spreading her legs a little bit more to make it easier for me to get even deeper in. And that’s how we fucked: her face down, flat on the bed, beads of sweat collecting on her toned back; me above her, feeling the mounds of her ass bounce as I plummeted into her.

After a few minutes, I pulled out altogether (“Oh, no,” she groaned), and pulled her hips towards me. She got the message, and came up onto all fours. I pushed in again, going deeper than before with the new position. “Oh Andy, fuck me baby, fuck me,” she told me, as she pushed back against me each time I entered her.

I grabbed her shoulders to pull her against me, pushing as deep and hard as I could each time my prick plowed her cunt. In and out, in and out, feeling my orgasm get closer. But I remembered how much she enjoyed the small bit of rimming I’d done, and I could see her tight ass below me, her asshole still moist from all the sweat, come, and saliva that had collected there.

I leaned back again, letting go of her shoulders and sliding my hands down to grab the cheeks of her ass. I played with them, massaging them, moulding them, separating them from the other, and making her asshole wink at me as we fucked hard and fast. Then I slid the thumbs down, underneath her ass to get some moisture from the bottom of her cunt, and then backup, over the perineum, until they were pressing either side of her rosebud.

“Oh god Andy, that feels so good baby,” she moaned as she dropped her arms and shoulders onto the bed, making her ass stick up even further. I played with her asshole, running my thumbs over it, pressing, stroking, rubbing, spreading her cunt juice around, until I pressed one a bit harder than usual, and saw her sphincter spread, letting the intruder in, resisting a little bit but not enough, and my thumb entered her asshole. Angela groaned beneath me. As I pushed harder, my thumb went into the knuckle, and she started to come, hips trembling with the force of it, her juices flooding my prick as I continue fucking her. I could feel her moisture running over my balls, she was so excited.

I kept on fucking her, intent now on getting my own orgasm, wanting to come inside this tight cunt as I watched her asshole clinging to my thumb, knowing that at some point soon it would be clinging to my hard cock. The thought of it sent a spasm down my spine to the tip of my prick, and I knew it wouldn’t be long. I reached forward to grab one of Angela’s hands, leading it down her cunt, and I felt her tunnel tighten as she started wanking her clit, then I straightened up again, grabbed hold of her hip with my spare hand, and starting giving her a good hard fuck, pulling her onto me with one hand as the other thumb continued pushing into and out of her ass.

It only took a few minutes of that for me to come, my man-juice spurting inside that hot sweet cunt as she came again on my cock, pushing herself back so hard that my thumb went all the way into her asshole. As my spasms subsided, I collapsed down beside her, panting hard. She took a moment to get her breath back, and reached down to fondle my still swollen prick.

“Baby,” she whispered, “that was real good, but don’t even think about trying to put this monster in my ass – it’ll tear me apart.”


It was a couple of weeks later that we went one step further. Don’t get me wrong – during that couple of weeks we had some great sex. A bit of anal fingering, some rimming, and more traditional sex, as well as just wining, dining, almanbahis and getting to know each other.

The next time something significant happened, Daniel was staying over with a friend, Stephen. The friend’s mum (Simone) was a right hottie. She’d had Stephen real young, so she was only about 28 or so now, still fresh and tight. And she knew it. Her midriff was always exposed to show off her flat, taut stomach over deliciously curvy hips. Her tops were tight enough to show that her tits were firm and more than adequate. She wasn’t tarty, mind: the midriff gap was only a couple of inches, just that bit above the waist of low-slung jeans or trousers, where the hips curved inwards to her narrow waist. And that was all you saw – never a large midriff PLUS loads of cleavage PLUS bare arms and legs. She kept herself covered up apart from that one little bit that let you know she was very tasty underneath the rest of her clothing. A classy dresser.

She was married, and apparently very happy with her equally tasty husband. Ah well. She kept me going in wank material during the period when I was seeing nobody.

Anyway, Daniel was there for the night, and Angela and I had the place to ourselves. I’d invited her round for dinner, cooked by my own fair hands. Of course, we didn’t quite make it to the first course…..


She turned up wearing a chinese-style silk dress. High at the neck, tight round the body, long to the ankle, but slit up to the upper thigh. Very tasty indeed. When I let her in, I deliberately let her walk down the hallway to the living room in front of me, just so I could see her bum wiggle in the silk. Like two pigs in a sack. I just wanted to throw her to the floor and take her doggy style right there and then.

But Daniel was still her, so that put the kybosh on any plans for instant sex. Angela didn’t have kids herself, but she had a couple of nephews, so she knew how to get on with kids. And Daniel seemed to like, which is a relief. He even took her up to his room to show her his favourite toys, so we was in special favour – he normally reserves that for friends who have been round longer.

Then Simone arrived to pick up Daniel. Oh fuck me, she was looking good. Tight, cropped top over those delicious boobs; her midriff showing; and some sports-type bottoms on, slack round the legs, but clingy enough to show the lovely curve of her ass. She and Angela chatted for a few minutes whilst Daniel put his coat and shoes on (which always takes a long time), and I could see Angela taking the occasional opportunity, when Simone was looking at me or Daniel, to look at Simone’s tits or ass, and waggle her eyebrows suggestively at me.

Eventually, Daniel got his stuff together, and was whisked off Simone for an evening of fun and games with Stephen. As the door closed, Angela just said “Nice tits. Bet you’ve wanked off plenty of times at the thought of getting your man-meat between those mammoths, eh?”

“I plead the fifth,” I countered.

We did do some small talk first, whilst I was preparing the food. Unfortunately, she made the mistake of sitting directly in my line of sight, legs crossed elegantly, showing her legs off right to the inner thigh as the material parted along the slit.

Just the sight of that, and the memory of our anal play previously was enough to get my dick rising in my pants. I was wearing casual trousers this time, rather than jeans, so there was nothing to keep the old boy pressed down tight against my thigh. I think she must have noticed, because she stood up, walked over as if she was going to the fridge, and then cuddled up into the back of me, pressing her breasts, stomach, and groin against me, running her hand down my chest and stomach to stroke my growing bulge

“Oh, Andy, what am I going to do with you?” she breathed into my ear as she rubbed her hand up and down.

“I can think of a few things,” I answered, as I carried on chopping some carrots. At which point she lowered my zip and slid her fingertips inside to rub up and down my straining cock, outside my boxers. I kept on chopping.

She brought the other hand round, and with both hands she undid my belt and the button of my trousers, and then she pulled the fly apart to get better access to me. Then she reached into the top of my boxers, pulling them down at the waist a bit, and reaching down to lever my cock up so it could taste the fresh air.

She grabbed hold of me just below my foreskin, and started wanking me, just moving my foreskin on and off my helmet. I kept on chopping, but with slightly less interest this time.

When she saw my apparent lack of interest, she grabbed hold of my hips and pulled me away from the worktop, worked more of my cock free of my underwear, and resumed wanking me, but this time with longer, firmer strokes. I kept on chopping.

Then she slid around me so that she was standing up between me and the worktop, right in the way of my chopping. She reached behind her, and almanbahis yeni giriş pushed the chopping board away to the side, then grabbed the knife from my hand, and put it off to the side as well. Then she looked me in the eye, and slowly slid down onto her knees. As her head reached my groin, she tilted her head and licked up my cock. I groaned, and then groaned even louder as she opened her mouth and swallowed the head of my cock. Her tongue swirled around me, as she started bobbing up and down.

I grabbed the back of her head with both hands, helping the up and down movement, but preventing her from slipping away. With her hands, she started to pull my trousers and boxers down, pushing them down to my ankle, as her hot mouth worked wonders on my prick.

She grabbed both cheeks of my ass, and took even more of my cock into her mouth. She wasn’t quite deep-throating (I’ve not yet found any woman who could), but she was doing a damned good job. I relaxed into it, enjoying the blowjob without any thought of having to give her pleasure or hold off my orgasm, just getting into it.

After a few minutes, she stood up, kissing her way up my body, all the way to my mouth. A lot of guys don’t like it, but it fucking turns me on when a woman kisses me after going down on me for a bit. No idea why, it just does. I kissed her back ferociously, grinding my groin into hers, pushing her back into the worktop. I grabbed her ass, and started working her dress up her, rucking it up around her waist.

When it was all tucked up, I grabbed her ass again, and lifted her up onto the worktop. She opened her legs and wrapped them around me, then shuffled forward so that she was rubbing her crotch up against my cock. It felt odd, so I looked down – no knickers.

“You dirty little trollop,” I said, as I licked her ear and rubbed my cock up and down her in return.

“Well, what was the point on putting knickers on? I knew they wouldn’t stay on for long. I’ve been wanking myself silly all day at the thought of us having sex again, so there’s no way I was going to wait till after we’d eaten. Besides, sex on a full stomach absolutely has gotta be bad for you.”

“I’ll tell you what’s bad for you…” I responded. “Trying to have sex in this position. Get down, turn around.”

She slid onto her feet as I kicked off my trousers and boxers. She turned round, pulling her dress back up again, exposing that delectable little ass and the dark cleft beneath it. Wasting no time, I grabbed my cock and positioned it ready for penetration, and she pushed herself back, sighing as I entered her.

“Oh god baby, that feels so good,” she breathed, working her hips to get me completely inside her. I bottomed out, feeling her tight buns against me, and I reached one hand round her waist to stroke her clit. She pulled away again, and I could feel the walls of her cunt close behind me as I withdrew. I pushed in, quite hard, and heard the slap as our flesh made contact.

We fucked, hard and fast, with her juices dripping down onto my balls and the sound of our fucking filling the kitchen. I wet a thumb in her juices, and pushed it hard and firmly into her ass. She grunted, telling me to “fucking fuck her”. I started really going for it, fucking her like I’d never fucked anyone before. She was rocking back and forth as I pushed my cock as deep into her as I could. I gave up trying to play with her clit, and just grabbed her hip with my spare hand to pull her onto my cock even more, whilst still playing with my thumb in her asshole.

She started to come, screaming out loud as she did so, but I didn’t stop. I just kept on thrusting my cock into her wet cunt, watching her ass cheeks bounce around as we fucked. I wet the other thumb, and started pushing that into her ass alongside the first one. I didn’t push too hard, just a slow gradual pressure. Well, as slow and gradual as I could manage when fucking her so hard. I could see her asshole spread, her sphincter muscles opening up like a flower to accept both my thumbs.

Angela was gone, moaning and groaning and shouting all sorts of obscenities into the kitchen air, which now smelled only of hot sweaty sex. Her asshole was clenching my thumbs, tight but unwilling to let them go. I spit onto them, making sure she was very wet, as I had plans. I could feel her cunt tighten again round my cock, and my own orgasm was approaching, helped by watching her asshole beneath me.

We got even closer to orgasm, and she put both her hands on her ass cheeks, pulling them apart to allow me better access to her ass. She was shouting now, just pure grunts in time with my thrusts, and I could tell we were both on the verge of coming.

As I pulled my cock back, I pulled a bit further so I came out totally, the first throbs starting to happen in my cock. I squeezed to hold it in, and whipped my thumbs out of her ass. I pushed down on her hips quite hard, whilst knocking the back of her knees with the front of mine, making her ass drop a bit… almanbahis giriş nicely in line with my cock.

Then I pushed – just enough to get the head of my cock inside her ass as she came, screaming at me, calling me a lying bastard and then telling me to come inside her ass, and her juices flooded out of her cunt to pour down my thighs. Her hot asshole clenched around my cock, squeezing it tighter than anything I’ve ever felt before, spasming as her orgasm continued, and that was enough to make my come spurt into bowels. Her orgasm seemed to last forever, and she was still having aftershocks as I started to recover from mine. Then she collapsed onto the worktop, body going completely limp from the force of her coming. She’d passed out.

Jesus wept, I’d made her pass out.

I was shocked, and was about to pull my cock out of her steaming ass, when I felt her asshole open up as she relaxed. Without even trying, my still-hard cock slipped another inch or two in. I froze, afraid of her going mental when she realised I’d gone further in. But she was still out for the count.

I could feel her hot ass walls around my cock, lubricated by my come, slippery and more relaxed than before. Experimentally, I pushed my hips forward a little bit, and my cock slipped even further inside that lovely ass of hers. An evil grin broke on my face, as I looked down to see her cute asshole split apart by my cock. My veins were bulging, making an even rawer image, and I pushed forward again. Another inch or two.

My mind was made up.

Slowly, I kept the pressure on, allowing my cock to ease further and further inside her. I could feel her sphincter pressure as it moved up my cock, and also the tight-but-flexible pressure of her inner ass walls – parting as the new intruder edged it’s way in. Ah, fuck me, her ass was exquisite. Grasping, clinging, but not too tight. Hot, kind of dry, but not too dry. Very different to the feeling of being in a cunt. I knew that once tonight was over, I had to have it again.

I started to nudge my cock in and our of her ass, going a little bit deeper each time. After a few minutes, and another inch or two inside, Angela had still not recovered, but I could feel her asshole start to get tighter again, so I knew it wouldn’t be long. I reached my hand round her waist, stretching down to her cunt, parting her lips and rubbing her clit.

She moaned, and lifted her head a bit…. then froze.

“Oh, shit,”I thought, “she’s gonna go ballistic,” and I got ready to withdraw.

But she reached around, and grabbed hold of the bit of my prick that wasn’t in her yet.

“Sweet jesus,” she said, “you’re almost all in,” amazement in her voice. “God, that feels good. I never thought you’d fit. How do you fit? Oh, fuck me!” she gasped as she reached back with both hands and pulled her ass cheeks apart again.

I took that to be a good sign, and resumed pushing my cock into her, slowly but surely. The thought and feeling of being in her ass, and watching my cock part her asshole as we fucked, had kept me hard, even after I’d come.

It was getting tight, so I looked round desperately for something to lube… the olive oil caught my eye, so I grabbed it and started undoing the top.

“Baby, reach into my bag there… there’s some real lube. Just be quick and fuck me,” whispered Angela. I reached into her handbag on the kitchen worktop, found the lube, and pulled out of her a bit. Then I spread some round the remainder of my cock, and round her asshole. I did wonder why she had lube in her handbag, but that question could wait for another day.

I started to move into her again, pushing in a bit and out a bit, letting the lube do it’s job. Gradually I got further in. Evantually, I got the last bit in, my lower stomach hitting the cheeks of her ass, and we both grunted.

“Oh, you fucking bastard, Andy. You feel so big. You bastard. … fuck my ass, Andy. Fuck me,” she whispered.

I took her at her word, and started pulling my cock out. I reached a hand down to her wet cunt lips, collecting her juices, then spread it round the rim of her asshole as more of my cock was exposed. Then I pushed in again, feeling her bowels open up around me. God knows why she wasn’t screaming… if someone shoved 9 inches of hot cock up my ass, I’d be raking their eyes out. But thank god she wasn’t, as I wasn’t stopping for any reason. She was pushing back at me a bit, straining to get more pleasure, and I saw her reach down to her cunt. As she started playing with her clit, I felt her asshole tighten around me, and I grunted at the extra pressure.

I reached bottom, and started pulling out again. The scene was one of my favourites from the occasional anal porn film I’d seen – a big cock pulling out of an ass, with the ring of ass clinging desperately to the prick, red raw with the effort. I wished I’d had a camera to record the fulfillment of many a wanking fantasy at last.

“Push out a bit, as though you’re straining over a shit,” I said, and I felt her do so. Her asshole blossomed, giving me a bit more room to maneuver. I began to fuck her a bit faster, and reached down to spread more of her lubrication around the base of my cock. Then I grabbed her ass cheeks, spreading them wide.

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