Anal At Last Ch. 04


[This story is one of a sequence I’ve written. Each part is sequentially numbered, 01 upwards, but also given a chapter number for a particular storyline. So this is part 4 in the sequence, and also part 4 in the “Anal At Last” part of the story. Other parts of the story will come later.

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



That Saturday, Samantha knocked at the door to start baby sitting. She was a pretty girl, not your typical blonde tart with a council-estate facelift (you know, hair pulled back in a pony tail so tight that it pulls the face back like a facelift…), but a brunette, with a bobbed hair style. She wasn’t that good at making the most of her looks, however, which was a bit of a shame. I’d always thought the boys at college would love her if she dressed up a bit.

Still, by not dressing up, it meant she could baby sit rather than being out with a boyfriend, so I was glad of that. She asked where I was off to tonight.

“Out with Angela, the woman you met the other day,” I said as I put the kettle on to make her a cup of tea.

“Oh yes?” said Samantha. “Getting serious are we?” she asked, smiling.

“When you’re old enough to know what serious means, come back and ask that again and I’ll give you a serious answer. Until then, get in there and put the TV on. I’m sure there’ll be a good episode of The Teletubbies for you to watch – I know how you college students like a challenge”.

She laughed, and walked through to the lounge, rucksack over her back with her course work inside it. Daniel must have heard her talking, and came helter-skelter down the stairs, shouting her name as he did so.


Angela arrived a bit later, silently lifting her rather large handbag as she licked her lips and put her hand up behind her head, sticking two fingers up like rabbits ears, thrusting her hips subtly a couple of times. I lead her through to the lounge with my hand on her arse, squeezing en route. Then I moved my hand up to her lower back as we went through the doorway and into sight of Samantha. The two women chatted a bit whilst I finished getting ready and settling Daniel down to bed, and Angela and I set off down the road on foot to the restaurant I’d booked.

“Nice girl”, she said.

“Yeah, Daniel loves it when she’s early enough to play with him; she’s really good with him”.

“Yeah, right,” she said, elbowing me gently in the ribs. “I bet in return you’d love to play with her one night, eh?”

“Now now Angela, be nice. She’s a sweet young girl who doesn’t need a randy old goat like me drooling all over her just because she’s under twenty and quite good looking.”

“Well, they always say the quiet ones are the worst,” she said, looking at me meaningfully.

“So how is it that you’re so noisy and yet not the best?” I asked. And so the banter began, both of us knowing that the rabbit was in her handbag, and a good night was ahead.


Angela was wearing jeans this time, nicely fitted to make the most of her ass, which was superbly shown off thanks to the leather boots that she also wore – you know that way that boots subtly shift a woman’s balance, making her legs longer and more toned, and her arse more pert and bubbly. Thankfully, the jeans weren’t the ones that had no rear pockets – I hate them with a passion, as they ruin the curve of a woman’s ass that jeans normally emphasise so well.

On top, she had a cardigan, and I think that was it, leaving her cleavage undone with no obvious bra showing. All during the meal, I kept glancing to see if she had a bra on, and it I obviously wasn’t being too subtle about it.

“Will you stop gaping at my tits!” she whispered a little fiercely. “If you keep that up whilst I’m trying to eat, you won’t be seeing any more of them tonight.”.

“How can I help it,” I asked, “when almanbahis you’ve left them on display for all to see?”

She sighed theatrically, the deep breath in only serving to push her breasts out more. I smiled appreciatively, at which she rolled her eyes, and tucked into her food again.

I looked about, and started another train of conversation, speaking quite loudly.

“The food’s good here, isn’t it? This chicken is lovely. Quite delightful.” She looked at me, a quizzical look on her face, and answered that her chop was also nice.

“Mind you,” I said, “I’ve heard that the rabbit here is even better”, placing emphasis on the word rabbit.

She snorted, shaking her head in disbelief. “Yes,” she replied, raising her volume a bit, “It is good here. Almost orgasmic. The best I’ve EVER had, in fact.”

I nodded my approval at her comment, and retorted with “I’m sure it is, but it can’t compare to the real thing, can it?”

She looked at me, unsure what I was getting at. “How do you mean?” she queried.

“The real thing. You know… a nice bit of PORK,” I said, smiling at my own wit. She almost choked on her food. I reached across to pat her back. “There there. You’re alright. What’s the matter? Is the pork a bit much for you?” I asked, keeping my volume higher than I would normally.

She got her breath back before answering with “No, no, it’s fine. A bit on the small side actually. I prefer a bit more meat personally speaking.” She pursed her lips, leaning back with arms crossed to see how I’d respond.

I thought for a moment. “Mmm. It’ll need to be big so that you can feel it going down, right?” She stared, disbelieving. “Otherwise you won’t even notice it touching the sides?” Two young women, in their late twenties I guess, sitting near us, started sniggering under their breaths, one of them looking at us to work out whether we were doing this on purpose or unintentionally providing them with some entertainment.

“Yeah, I know what you mean. However if it’s too big, it does sometimes need some lubrication to go down, it it’s too big… although that’s not a problem at the moment, obviously.” She had one hand up to her rubbing her chin at that point, and lifted her little finger, curling it back and forth in the universal sign language for “small prick”.

“Obviously not,” I said. Then I paused. “Still, I’m also really looking forward to the pudding here. I’ve heard they’re very good. Will you be having cream with yours?”

She shook her head, pityingly, although I could see her nipples pushing her cardigan out. No bra then. “Maybe. Although I suspect that you won’t be lucky enough to be getting any tonight,” she said. More laughter from the girls nearby.

“Oh, I think we’ll be lucky enough. Double helping, I think. Some CREAM and PIE will be good for you I think, to put some meat into your skinny-assed frame,” I said looking up and down her suggestively.

“I’ve already had the only meat I’m having tonight,” she said, casting one eye at the girls to let them know they were in on the joke.

“And there’ll be no fish near these lips tonight. So shall we call it a night and head back?” I asked.

“Oh god yes”, she said, under her breath and deeper in her throat, raising one eyebrow suggestively as she ran her fingers up and down the neck of the wine bottle. Then she ran one finger up the bottle, collecting the condensation, and sucked her finger deep into her mouth, gazing deep into her eyes.

I settled the bill while she went to the ladies, and then I lead her out, my hand in the small of her back as we left. The two young women watched us as we left, so I threw them a knowing wink. They raised their glasses to us, which made Angela laugh.


We started on the walk back to my place, her arm in mine, continuing the banter. At a pre-planned point, I grabbed her arm and pulled her into a dark alleyway, pushing her up against the wall.

“Mmm,” she said, wrapping her arms round my neck and pulling me close, “couldn’t you wait till we get home?”

“I could wait, but I knew you were desperate for it, so I thought I’d give you a little treat.” I started kissing her, and ran my hands down her back to her bum, pulling her in closer still. She squirmed against me, her hot breath coming slightly faster, as she squeezed one hand down between us to rub my groin.

I pulled one hand up to her front, under her almanbahis yeni giriş cardigan. I was right, no bra, so I gently squeezed her nipple, feeling it harden in my hand. She groaned, and grabbed my hand, twisting away to lead me back into the street and towards my house.

We got back, chatted with Samantha a bit whilst she packed up her college books. Angela undid her boots and took them off, leaning forward in my direction so I could see her cleavage. Samantha was surprised we were back so early, and I responded that I had a big day ahead of me tomorrow and wanted an early night. She looked between Angela and I, nodded, and said “mmmm-mm”, like she knew what that meant, and let herself out. I picked up Angela’s handbag, and then lead her by the hand up to the bedroom. Then I lay back on the bed, putting her handbag down beside me, then put my arms behind my head, waiting expectantly.

“Yes? Are you waiting for something?” she asked.

I nodded towards her handbag. “For the show to begin.”

“If you think I’m just going to whip down my pants and give you a free peep show, you’d better think again,” she said, faking anger. “I’m not one of the other women that normally take pity on you, some cheap slut who’ll do whatever you want just to get some attention from a man.”

“Damn. Obviously I was mistaken about you.” She picked up her handbag and threw it at me. I opened it, and pulled out the rabbit. “Come here,” I said, and held my arms out for her.

She clambered up onto the bed, and straddled me. We kissed for a bit, her hot tongue searching for mine, and then she leaned back and slowly undid her cardigan buttons, like a slow striptease. When she’d undone the last button, she held the sides together for a moment, and then pulled them apart, arching her back to push her bra-less tits towards me. I growled and bent my head to take one in my mouth. She pulled my head closer, moaning as I gently bit her nipple. I slid my hands down to her bum, pulling her into my groin.

I feasted for a while on one tit, and then pulled her down to my side, turning myself so I was half on top of her. Whilst I lowered my head to her other tit, I slid a hand down to her jeans and undid the button and zip. Then I rose up to straddle her legs, and she lifted her pelvis up to allow me to pull the jeans off her waist. I left her knickers on, however, and wriggled myself back to the bottom of the bed so I could pull her jeans off. She lay there, just her knickers on, whilst I started stripping off. She must have remembered what we had planned for tonight, as she slowly slid one hand from her neck, down over her breast, tweaking the nipple as she went, over her flat stomach, and into the top of her panties. Her hips bucked as she pushed her hand deeper, and she moaned deep in the back of her throat. Her other hand came up to her breasts, rubbing and playing with one of them, and she closed her eyes, licking her lips at the pleasure she was giving herself.

I finished stripping, and sat back in a chair I keep in my bedroom, my erect cock standing up proud. Angela pushed herself further up the bed, so that she was leaning against the headboard, knees drawn up and legs spread. She looked me in the eye as she reached down with one hand to pull the gusset of her knickers to one side, as she reached with the other hand to run a finger up and down her now-exposed slit.

She closed her eyes again as she played with herself, and I could hear her breath coming faster. She pushed that fingertip inside her, just a little bit, and she moaned quietly. She opened her eyes to look at me, and looked down to my hard cock. She pushed her finger in deeper, as I reached a hand down to grab the base of my cock. As I slowly slid my hand up, she reached down to pull her knickers off, and as I slowly slid it down again, pulling the foreskin tight, she reached into her handbag and pulled out the rabbit.

She turned it on, setting the “ears” buzzing, and then turned it round so that it pointed down to her feet, the ears just touching her cunt. Then she pressed it down, setting the ears vibrating against her clit. Her stomach clenched, drawing her knees further up towards her, and she murmured “oh god, that’s good” under her breath.

She kept this up for a few minutes, running the rabbit around so that the ears rubbed all over her clit and lips, and then she turned it around and started pushing it inside her. almanbahis giriş I could see her lips split, clinging to the rabbit as she pushed it inside her. She pulled it out again, and it pulled her lips out with it, the wet flesh gripping the intruder, unwilling to let it get away. Again and again she pushed and pulled, each time going a little bit further in, each time pulling it out a bit more wet, glistening with her flowing juices.

Eventually, she was pushing it far enough in that the ears were on her clit again, and she writhed at the feeling. Her speed increased, and as she pushed it in as far as she could, she rotated it to get maximum feeling to her clit. Her other hand was wandering, to the inside of her thighs, her tits, her stomach, and then down to her groin, underneath the glistening rabbit to where her lips joined at the bottom of her cunt. Then a bit lower, to her perineum, between her cunt and asshole. She snatched her hand back, opening her eyes to see if I’d see her reach towards her ass.

I had, so I just nodded slowly, growling “Go ahead baby,” still wanking my cock with one hand, while fondling my balls with the other. She closed her eyes again, and let her spare hand slide back down. As she carried on using the rabbit, she used that spare hand to spread her juices down past the bottom of her cunt and to her asshole. She groaned, just once, as her finger rubbed her asshole, and she slid slightly down the bed to give herself better access. But she couldn’t really reach, and I could see that she was straining to get better contact. I stood up, went over to the bed, and reached down to slide the rabbit from her steaming cunt. She sighed as I pulled it from her, and I lifted it up, sniffed it, and then licked some of her juices off it. She groaned at the sight.

“Get on all fours,” I told her, the lust making my voice deeper and huskier, and she complied, turning over, spreading her knees and arching her back to thrust her ass back at me. I slid the end of the rabbit over her cunt, from the front all the way to the back, collecting her juice. Then back up again to the top, pressing it against her clit. She pushed back against me, and I slid it down again, this time going a little bit further down, towards her ass. Backwards and forwards, a bit further each time, spreading her juice all around, until I was sliding it between the cheeks of her ass. I didn’t press it in, just sliding back and forth, then for one last time, I pushed it down to her cunt, and then pushed it inside her. She grunted, and sighed her pleasure.

I reached up, and tugged at one of her hands. She shifted her weight into her other arm, and let me pull her hand down to her ass. I took one of her fingers, and slid it down from the start of the crease of her ass, downwards, towards her asshole, as I carried on fucking her with the rabbit. She took the lead, and slowly, gingerly, carried on moving her finger down to her asshole, rubbing it, pressing it, stroking it, but not pressing inside. Not yet, I thought, but next time you’ll finger your ass yourself.

She was panting now, her orgasm approaching, as her hips pushed up and down to get the leverage on her pleasure centers. I could see her thighs trembling with the pleasure, and the muscles in her asshole clenching and unclenching as she brought herself closer. I leant forward, real close, my hot breath on her rosebud. “Oh, please, do it, Andy, do it,” she moaned.

“Tell me what to do,” I whispered back at her.

“Lick me, please lick me”.


“Lick my ass Andy, lick my hole. Oh god, Andy, lick my ass, please.”

I pulled her hand away as I lowered my head. “Oh, yes,” she moaned as my tongue touched her asshole. I felt it spasm underneath me, and I pushed harder, licking up and down and around and around. I pulled out the rabbit, dropped it, and wrapped my hands round her thighs, pulling her close, I felt one of her hands reach down to her clit and start wanking herself, and then I really went to town on her arse, curling my tongue up and pressing it in, feeling her rectum open as my tongue slipped inside. At the same time, I pushed two fingers into her cunt. Suddenly, she came, shaking all over, murmuring “oh fuck oh fuck oh fuck,” as her juices flooded out down her thighs. Her asshole tightened on my tongue, forcing it out, but I kept on licking on the outside as her orgasm continued, feeling her cunt walls tighten on my fingers, finally relaxing as she flopped down onto the bed, panting, the sweat collecting in the top of the crease of her ass.

“Oh baby,” she murmured when she got her breath back. “That was so good. Now get your big prick up here and fuck me senseless.”

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