Anal at Last

[The story so far: I've recently divorced my wife, and am raising my son by myself. After a long abstinence, I've met a woman (Angela) and we've been indulging in anal sex, new to both of us. My babysitter (Samantha) has watched us have sex, and confessed to Angela. That set Angela thinking, and she said she wanted me to flirt with Sam, and let Sam flirt with me, but without letting Sam know that it was planned.

Also, Angela and I have been watched by Angela's neighbour, Peter, while we had sex in the garden. The next day, I'd got Peter to agree to come round that night to see us, without telling him that we'd gotten off using him in a fantasy three-some.

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

Bill's late wife: Michelle

Bill's girlfriend: Barbara

Angela's friend: Jules

My ex-wife: Sharon

Daniel's friend: Stephen

Stephen's parents: Ken and Simone

Peter: Angela's young neighbour

]

I had a plan. For the next four hours, till Peter arrived (assuming that he did actually follow-through), I'd tease Angela like mad. Then give her the time of her life with Peter. I hoped she would appreciate everything I was doing for her...

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I went back indoors after speaking to Peter, and dropped the milk into the fridge. Angela was loading the washing machine, bent over to sort out the clothes, her ass nicely thrust out. She'd not really got dressed after our afternoon sex, instead just throwing on some underwear and a thin dressing down.

I went up to her, and quickly lifted up the dressing gown, displaying her panty-clad ass. Then I bent to kiss it, as Angela murmured something like "Jesus Christ, not again."

Turning, she spoke loudly. "Andy, I'm in the middle of housework. Get a grip on yourself."

I pulled her close into me, taking hold of her bum and having a good fondle, the dressing gown still up around her waist. The smooth skin of her bum just underneath her knicker-legs was my target, and it felt fantastic. "Sorry honey, your ass was just too delicious to pass up the opportunity." I kissed her neck a few times, pulling her groin onto mine.

She returned the kiss, saying I was incorrigible. I slid my hands up, and then down into her knickers, feeling her naked bum again. Her hips ground into mine a little bit, my cock coming to attention with the pressure, as I fondled her ass cheeks. She put one hand behind my neck, pulling my head down as she opened up the top of her dressing gown with the other hand. I took the hint, and kiss her cleavage and her breasts left exposed by the bra. She sighed, and ground into me further.

After a few kisses, I lifted my head. "Baby, I've had an idea. Remember how turned on you were the other night, when I teased you all evening, but kept backing off because of your period?"

Angela put on a fake pout. "Yes, Andy, I remember. It wasn't very nice."

"Let's do it again. Let's tease each other for the rest of the evening till we go to bed, get each other worked up but without coming, and then go to bed and I'll let you give me a good hard fuck."

"Did you say 'You'll let me'?? Don't you mean 'I will let you'?. Didn't you know that sex is always at the discretion of the woman?"

I bent my head again to kiss her cleavage, whilst running one finger down the crease of her ass, lightly touching her rosebud. "Are you sure?" I asked. "You can always say no."

"Oh god Andy, you bastard. You know there's no way I'm saying no... as long as you promise to rim me later."

"Me? Rim this delightful little ass of yours? It'll be a pleasure, my lady."

"Good," she responded. "Now let me finish this washing, and then you can start teasing me by pouring a glass of wine, getting some baby lotion, and massaging my feet. Those shoes I had on today were murder. If you do it nicely, maybe I'll use the lotion to massage a part of you, in return."

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We sat having the wine, Angela in the armchair, still clad in her dressing gown and underwear, me knelt at her feet. I did give her a foot massage, as it's kind of a sensual thing to do anyway. Luckily she had nice feet.

As I massaged one foot, she rested the other foot on my thigh. Of course, it didn't take long before she was rubbing it up and down my cock, through my jeans. I finished both feet, and then started massaging her calves, slowly working my way up her legs.

At one point, she sighed, and parted her thighs, giving me a glimpse of her now uncovered quim. "Do you like what you see Andy? I thought I'd slip my knickers off earlier, to give you a cheap little thrill."

I reached her knees, and gently parted her thighs even more to give me access to the soft creamy flesh in-between. Adding more massage lotion to my hands, I asked her to pull her dressing gown out of the way, so I wouldn't get it marked. She laid back in the chair, sliding down slightly, her thighs opening more, and I leaned in to get a better position. I could smell her arousal in the air as I rubbed and stroked her inner thighs, working closer and closer to her groin.

She moaned as at last my fingertips touched her mound, and her hands came up to start playing with her tits through the dressing gown. I slid one finger up her moist lips, parting them, and she moaned my name under her breath. I pushed that finger in slightly, and her hips pushed forward to get more into her.

I fingered her for a few moments, and then grabbed her behind the knees and pulled her further down the armchair, so that her bum was hanging off the edge. Then I lifted her legs up so that her knees were on my shoulders, and lowered my head to her groin, kissing her inner thighs, licking, and nibbling, working my way towards her hot hole. She held the back of my head, urging me on.

I ran my tongue up her lips, and she groaned, "Oh Andy, that's good. Lick me baby, put your tongue inside me." I did as she asked, making my tongue firm, pushing it as far inside as I could, sliding my hands under her to grab her bum and pull her into me. Her thighs clenched on the sides of my head, preventing me from pulling away.

I licked up and down her slit, spreading her lips, tasting her juices, flicking at her clit, as I wormed one hand further underneath her, aiming for her asshole. She lifted that cheek to give me easier access, saying "Oh, that's it baby, lick me, give me your tongue, taste me... further Andy, push your hand further, finger my ass while you lick me baby."

I got one finger to her asshole, and started rubbing around it, hearing her moan above me. She was dry there, but I had plans for that. When she was starting to get really turned on, I pulled my hand away from her ass, and used both hands to push her knees even further back towards her shoulders, exposing her asshole to my gaze.

I eased her thighs apart to give me room to move, and looked her right in the eye as I started licking lower and lower towards her rectum. She grasped the back of my head again, pushing me in hard to her. "Oh, Andy, do it, rim me... stick your tongue in my asshole baby... you're so dirty... but you make me so horny... oh yes, Andy, that's it... oh god I can feel your tongue... I love your tongue in my back passage honey... oh fuck that's good... please tell me you'll fuck me there later... I want you to baby, I want you to stick that big cock of yours in my ass and make me scream as you push it inside..."

I curled my tongue up, stiffening it, and pushing it into her ass as far as I could, and ran one of my hands up to her cunt, fingering her while I rimmed her ass. Her hips started bucking, and I could tell she was getting close to coming. I kept it up a bit longer till she was very close indeed, and then pulled away from her, kneeling on the floor in front of her.

"Andy, baby, don't stop," she panted.

"Angela, remember our deal? Teasing only, till we have sex tonight. Don't worry, you'll definitely enjoy what I've got planned for you."

She pouted again, and then slid off the seat and knelt in front of me. She reached forward, undid my jeans, and pulled them down as far as she could. Then she reached into my boxes, and pulled my cock out of the fly.

She started wanking me, saying "Baby, let's just have sex now. Look at us; we're both as horny as fuck. Let's just fuck each other senseless... we can tease each other later, or another night. Come on baby, take this big boy and stick it where your tongue just was."

I said nothing, but just pulled her hand away, and stood up, taking a hold of her head and pulling her towards my rampant cock. She took the hint, and opened her mouth to let me in. She sucked for all she was worth, gazing up at me as she swallowed my cock, wanking the lower part of my shaft with one hand, fondling my balls with the other. Damn that felt good. She was definitely getting better. Maybe she had been taking lessons off the mysterious Jules after all.

I stood there and enjoyed her mouth for a while, and then pulled out. I lifted her up and threw her gently onto the sofa on her back, and then lowered myself on top of her. "Oh, yes, baby, fuck me... fill me up... make me come on your hard cock," she moaned as she spread her legs wide to let me in. I didn't try to enter her; instead, I just rubbed my cock up and down the outside of her lips, grinding into her clit. She tried to push me away from her, grabbing my cock to line it up with her cunt, but I resisted her. Instead, I just rubbed away, up, down, left and right a bit, seeing her getting more turned on.

I craned by neck, bringing my mouth down to her breasts. She took hold of one, lifting it up to get her nipple in my mouth. She moaned as I took it in and sucked hard on it, gently nipping it with my teeth, as I slid my hands underneath her to grab her ass cheeks and pull them apart to stretch her asshole.

Then I got off her and stood up. "That's enough for now Angela. I told you. Teasing only, till my little surprise later."

"Oh baby, you're cruel," she responded. Then she ran her hands down to her cunt and started wanking herself, one hand pushing in, the other rubbing her clit. "But you didn't say I couldn't bring myself off... watch me, baby, watch me come..."

I grabbed her hands and pulled her to her feet. She stepped in close, wrapping her arms around me, bringing our groins into contact again, her nipples stabbing into my chest, grabbing my hands and bringing them down to her ass. I enjoyed myself for a few moments, kissing her, nibbling her earlobes, running one finger up and down the crease of her ass, not quite touching her asshole. She arched her back, pushing her ass onto my finger, and I let my fingertip rub her asshole, but only for a few seconds. Then I broke the hold, stepped back, and reached down to my rock-hard cock. I started wanking it slowly, and squeezed it a bit to make some pre-cum ooze out. I collected it on finger, and then lifted that finger to her mouth. She eagerly took it in, sucking it clean, giving it a mini blowjob.

Then I pulled away again, and strolled butt-naked into the kitchen, my erection bobbing before me. "Let's have that dinner we had planned?" I called behind me. I heard her growl her frustration at me.

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I made the dinner, and came back into the room. We sat and ate it, both of us still naked chatting about the usual sorts of things - work, TV, favourite holiday vacations. Then when we'd finished, I put the dishes away in the dishwasher and sat on the sofa. I reached down to my cock, and said to Angela "Watch....", as I started wanking. I leaned back into the sofa, closed my eyes, tilted my head back, as I wanked with one hand, and used the other to stroke my balls, my inner thighs, my stomach, my nipples. My cock quickly came to life, raising it's head, as Angela started playing with herself as well. She sat on the floor opposite me, kneeling down, her legs spread to let me see her cunt as she slid a finger inside her.

After a few minutes, I pulled her up to me, and then eased her down into a straddling position. She took the hint, and lined my erect cock up with her cunt, forcing herself down onto it. She was still not quite wet enough, so it took a lot of pushing. "Ah, fuck Andy you're big... you feel so good... ah... nearly there... fuck... oh yeah... that's it". As she pushed, I could feel her natural lubrication increase, and by the time she was down on me completely, she was wet enough to make fucking easier.

I put my hands behind her, cupping her ass, bodily lifting her up and down on my cock. It was great to see her lips cling to me as she rose up, inch after inch of my throbbing meat exposed, only to be swallowed up again a few minutes later.

I put one finger up to her mouth, and she took it in, licking it, making it wet. I then took hold of her ass again, and ran that finger round her asshole. She moaned into my ear, and then arched her back, exposing her tits. I ducked my head, and started sucking on one of her breasts as she rode me, still not penetrating her ass.

I lifted my head. "Do you want me to do it?" I asked, gently pressing against her asshole

"God Andy, yes."

"Say it, Angela, tell me what you want me to do."

"Do it Andy, put it in."

"Put what in? Put it where? Beg me..."

"Please Andy, do it, put your finger in my ass baby, finger my asshole."

"Tell me why"

"Because I love it baby... I love you playing with my ass. I want your finger in my asshole baby while your cock is filling my cunt. Then I want you to take that cock and split my asshole with it. Make it hurt. I'm your little anal slut baby. I love having you where no-one else has ever had me. I love your cock in my ass!"

She was getting turned on, her breath coming hard and fast, and I knew we should stop soon. I still wanted her worked up and very frustrated. It was getting on for six o'clock, so there wasn't long till (all being well) Peter should arrive.

When she was getting close to an orgasm, I pulled my finger out of her ass, and lifted her off me.

"Oh baby, this is so bad of you. I was getting close then."

"Trust me Angela, you're going to love it later. Now... let's have a look at your DVD player," I said, as I walked over to her TV stand.

"Why?"

"Remember me saying the other night that I wanted to watch one of your porn movies whilst we're on the sofa and I'm inside you? Well, now's as good a time as any."

"Oooh, that'll be nice. I'll leave it to you, Mister Geek Man."

"Now now, Angela, be nice. If you take the piss out of my geekness, I might have to withdraw the use of my tool," I said, wanking my cock in her direction.

"Andy, we both know that you'll last about an hour before you're begging me to let you in. Now get on and sort out this porn."

I worked out that her DVD would play AVI files, so I went up to her PC to burn a movie or two to DVD from her porn collection. One of them was a story (

A story? in a porn movie?

I thought, surprised) about a couple on honey moon who have their own side-adventures with the locals.

After all this, I hoped Peter DID turn up!

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I went back down with the DVD, and started it playing in the player, then stretched myself out on the sofa behind Angela, my semi-hard cock nestled between the cheeks of her ass, one hand cupping a breast. She nestled into me as the movie started.

I forget the title now, but it was about a typical porn couple - him bulging with muscles, her with great tits and ass. Instead of shagging his new wife, the guy gets off with someone that works in the hotel, including some oral, standard, and anal sex. His wife finds out, and then - joy of joys - indulges in group sex with two hunks who are at the hotel.

We got to the group sex section without any penetration between Angela and I, but our hands were busy. I had one hand down underneath her bum, two fingers in her cunt from behind, the other hand underneath her, playing with one of her breasts. My cock was tucked neatly into the crease of her ass, rubbing up and down slightly, working my foreskin and rubbing against her asshole, keeping us both on the brink.

Her cunt was sopping wet, my hand covered in her juices, after half an hour of teasing and fingering. Her asshole was also wet, covered with my pre-cum which flowed from my cock, making the crack of her ass slimy and slippery.

The girl on screen straddled the first guy, giving the other guy a blow job. I looked at the clock. 7:15. Time to take it to the brink. I lifted Angela's uppermost leg higher, giving me better access. Then I grabbed my cock, and pulled it down to line up with her cunt from behind. As the girl on screen sank onto the cock, I pushed my cock into her, easily entering her as far as I could in this position, her insides parting to let me into her sopping, and very hot, cunt.

Angela moaned into the air, pushing back onto me. I brought my wet hand up to her mouth, pushing two fingers inside just as the woman in the DVD took the other guy's cock in her mouth. "Is that what you want baby? Two hard cocks ready to fuck you senseless? Two men driven wild by how sexy you are, their cocks rock-hard, straining to fill your holes?"

She groaned onto my fingers, working her hips back and forth, helping to drive my cock in and out of her depths. "You do, don't you Angela? You want two hunks to serve your every whim. To take you and use you. To fuck you like you've never been fucked before. One of them to fill your cunt like I am now, and one forcing his hard cock into your mouth, making you suck his meat, his juice on your lips."

The guy that was getting a blowjob pulled out, and stood behind the woman, starting to finger her ass. "You want the other man to finger you just like that slut on the screen, don't you?" I pulled my hand away from her mouth, and squeezed it between us, sliding it down to her asshole, rubbing a finger around the outside, spreading juices from her dripping cunt around. "You want him to rim your asshole whilst you take another man's cock in your cunt. You want him to push a finger inside..." I did just that, sliding my finger in about an inch or so.

"Oh fuck Andy, do it, finger my ass, fuck me... you've got me so fucking horny baby... I love fucking you... I love your cock in my holes..." She reached behind her with one hand, grabbing my hip to pull my cock deeper. I pulled back, giving the hand on her ass room to maneuver. "Oh god Andy... you feel so good in me..."

"Angela, honey, we've got to stop -"

"No! Andy, keep fucking me, make me yours, make me come!"

" - as my big surprise will be here for you soon." I started pulling out, her cunt clinging to me as I did so.

"Andy, no, stay in me, fuck me, come in me."

"Angela, no. Now behave. You've got about half an hour to get changed. No showering. Just freshen up and put some clothes on. There'll be a delivery man here soon, and I don't want him catching sight of you."

I clambered over her to get off the sofa, and eventually she submitted and stood up. A second plan occurred to me. I stood behind her, coming close, I slid one hand round to her front, pushing one finger into her cunt. The other hand I ran behind, spreading some of her cunt juice around and sliding a finger into her ass.

I worked both fingers in and out. "On second thoughts, put some sexy clothes on. Something very sexy. Something that covers up most of you, but leaves enough on show to give the delivery man a hard-on as soon as he sees you. Then when you've hard your fill of flirting with him, I'll fuck you harder than you've ever been fucked before. You'll be coming so hard and so often, you'll pass out after losing track of how many times you've come. Then, when you're unconscious, I'm going to take your ass and use you to get me off. You'll sleep with my come leaking from your ass. Then I'm going to take some photos and post them online to let horny little men wank themselves stupid over the sight of my come dripping from your asshole." Angela groaned, reaching up to kiss me.