Naomi and I have been going out for about six months. I’m Jamie, divorced, and she’s widowed. Now we’re approaching forty, I suppose we’re a bit old to be calling ourselves boyfriend / girlfriend. I’d like us to live together but she has a daughter at university. Wants to keep ‘the family home’ as it is, until she flies the nest. Makes sense, so we see each other weekends and some evenings.

Our sex life is a little unusual. Took a while before it kicked off, and a month before we got round to oral. She was unsure and, with hindsight, probably didn’t know what it was. I had lots of porn clips on my computer, so I spent a couple of evenings sorting them into categories. That way I could introduce her to, shall we say, non-standard sex, a little at a time. I was very matter-of-fact about it, implying that every woman did this, she’d just been leading a sheltered life. Once she’d watched a few, she got the hang of it. Better – she got really good at it.

So what’s unusual about that? Well, she had never done anything except straight missionary position with her husband. There can’t be many English women who get to their late thirties and have never had a bloke go down on them. Seems her old man had some Victorian attitudes to it all. Theirs had been pretty much an arranged marriage, a family agreement anyway, and he only had sex with her sufficient to get her pregnant. His real sex life was with prostitutes and ‘girlfriends’. In his eyes, they were all dirty sluts. Women were not supposed to enjoy it; all sex was disgusting. And with a spectacular display of ignorance, for the twentyfirst century anyway, he walked out on her when the baby was not the son he’d ordered.

His life went as it had before. He had nothing to do with his daughter except pay maintenance for her. But no divorce; that was not allowed. And over the years she knew he was keeping an eye on her. She had no boyfriends. Or many friends at all, come to that. Then, just after Susan got into university, he dropped dead of a heart attack. I met her soon after and brought her out into the real world.

Thus, I coaxed her along the path towards more interesting aspects of sex. She felt she had somehow failed in her marriage, and wanted our relationship to be a success. So I persuaded her she should try everything. She went for it enthusiastically, believing what we did was normal for every loving couple. She swallowed, let me withdraw from her cunt and finish in her mouth.

And soon we got to anal. She watched the videos and took it all in. She queried arse to mouth and I assured her we would get into a rhythm where we did when she was ‘empty’. She was also relieved when I told her the porn models had lubrication first, and that wasn’t always shown. The first time we did it, I proceeded slowly, teaching her to push against me at the moment of penetration to allow my penis in comfortably. She took to it like a duck to water. I’m not claiming she enjoyed it more than vaginal or oral, but it wasn’t long before she could take it with no more lube than a gob of spit, or the slime from her cunt.

So here we are; me, fairly sexually experienced, and getting more so. And Naomi, same age, the mother of a eightteen year old who’s probably had more men than her. She once told me her husband was the only man she had ever had sex with. And then less than a dozen times in total! There are few things more satisfying to a man, than to hear naïve questions like: ‘I swallowed it all, is that right?’ and ‘That felt nice, but can I put some more lubricant up there next time?’. I taught her nearly everything. The only thing she wouldn’t do was fuck other guys; with or without me watching. Pity, I’ve always been a voyeur.

Naomi is gorgeous, a genuine head-turner. Brown eyes and brown hair. The latter in a shoulder-length style similar to Rita Hayworth in ‘Gilda’ and it has a tint of red. She’s just a fraction over five foot tall, and extremely slim. Her daughter towers over her – well, everyone does. She complains she’d like to have bigger breasts, but I love them as they are. They like a twelve year old’s, but with a woman’s nipples. I told her big ones are all very well bouncing along the beach, or being manhandled in porn movies, but in bed many men preferred smaller ones. Me? I’m just an average looking bloke - with a better than average sex life. “Is it true, men say more than a handful is too much?” “Some do. I say more than a mouthful is too much!”

I soon became aware Naomi had a low tolerance to alcohol. She had barely been old enough to drink when she got married, and her husband had not allowed it. Claiming wine made her thirsty didn’t help and rapidly pushed her over the edge. The upside was the sex was really wild when she’d had a few. She’d take it up her arse, then suck me clean, and remember nothing the following day. I wondered about those blackouts. She seemed to know what was going on when we were doing the dirty, yet recalled nothing the following morning. It didn’t bother her when I told her either; she just smiled and said ‘I hope I had a good time, I’m sure you did!’. I just hoped her memory lapses were not symptoms of something more serious.

Now I come to think about it, our current situation may have come about at Bill’s house-warming do. We’d both had a few. It was getting late, some people had gone home, and Christine, Bill’s wife, collared me in the kitchen. She’d started flirting with me the moment we’d arrived. I’ve known Bill since uni, but never liked his wife. It was pleasant when she pushed her soft tits against me of course. But they were a bit on the big side for my tastes. “So Naomi picked you then?” “What do you mean?” “She’s gorgeous. Could have had any man she wanted. I hear she was beating them off with a stick after the funeral. Not a very big stick apparently. You’ve landed on your feet there – if you can manage to keep up with her.”

I didn’t have to put up with this kind of sarcastic insinuation. We were the only ones in the kitchen so I thought it best to stop this bitchiness in its tracks now. “It so happens that Naomi and I got together less than three months after her husband’s death. If you’re implying she had loads of men in that time, you’re misinformed.” “Well, perhaps not all at the same time!” That was her parting shot and she flounced out, oozing jealousy. I’d been drinking beer that night but grabbed a discarded glass of red, and downed it. Better calm myself and give the mouthy cow time to get well away. I decided to get Naomi out of there. She’d be pretty drunk by now anyway. Time to see if she was ready to try some anal.

In the lounge, there were a few women chatting on the huge settee. Pretty knees and thighs on display and a couple of knicker flashes, getting me horny. Most of the guys were in the garden smoking; not allowed in the new house. Suddenly there was a loud screech from upstairs. “Come on!” I went up to find two women banging on the bathroom door. One was crouched up, gripping her crotch through her jeans. She turned to me saying: “Oh good, it’s you Jamie. Naomi’s fallen asleep on the loo!” “There’s another toilet downstairs ladies.” “Someone’s been sick in that one. Christine’s cleaning it up now.” Not all bad news then. I banged on the door too. “Naomi?”

“Go down and get Bill would you? I think there’s a way of opening this door from the outside. Needs a screwdriver or something.” I went back down and found him. “No problem mate. You could have done it yourself with a coin. It was designed for exactly this kind of situation.” But when we got to the top of the stairs, the women had gone, presumably into the bathroom, and Naomi was slumped against the wall.

“Sorry for all the fuss. I must have nodded off.” “No harm done.” said Bill. “Come on babe, let’s get you home.” She fell asleep again in the taxi. And once we were in bed, she insisted on vaginal only. Never mind, early days. Next morning, she had no recollection of falling asleep in Bill’s bathroom. This blackout business was worrying, but it did give me an idea. Not one I’m particularly proud of, but, hey, I forgive me.

We’re into anal by July, and my boss is invited to a Saturday evening event. On the Thursday before, I’m in his office. His wife is ill and he doesn’t want to go on his own. He’s called the customer who is happy for me to take his place, and invite a partner of course. “It’s only fair that you should get some of the perks anyway. You did most of the work with them, so you’ll know more of their people.” I’m hardly about to disagree. It’s to be held in the grounds of some stately home. There will be a couple of marquees and a free bar. The theme is The Roaring Twenties. And all attendees are to dress appropriately.

That evening, straight after work, I met Naomi at the hire shop. The manageress assured us no-one else had asked for fancy dress of that style. The venue was near Guildford, well over the county border from us, so we were probably the only local people attending. I plumped for a white gangster suit with matching shoes, a white felt fedora and white tie. I already had a black shirt ... Naomi chose a short black flared dress with sequins, and a sparkly headband with black feather. No need for a bra. She already had suspender belt stockings and matching frilly panties – all in black. I had no doubt the sexy undies would be carelessly on display soon after her third glass of wine. But who cared? No-one would know her.

We drove over on Saturday afternoon and got into a nearby hotel, who booked us a taxi. “We have someone else staying here who’s going to that bash.” said the receptionist. “Shall I call their room and see if they want to share your taxi?” She did, and they were delighted. Townies – it hadn’t occurred to them they couldn’t just step out of a country hotel and flag one down. We met them in the bar. I wasn’t sure what he was supposed to be. Top hats in the twenties? He looked more like a wedding guest.

His wife had already downed a few and was dressed as a flapper girl, like Naomi, but she didn’t carry it off as well. They had smaller busts in those days. Fantastic strong legs though, and an even shorter skirt than Naomi’s. When we piled into the taxi, the guy had to sit in front, refusing to take his topper off. I was not about to complain, wedged in the back between two be-stockinged flappers.

His wife didn’t mind in the slightest when the taxi lurched, and I ‘accidentally’ squeezed her thigh. In fact, checking that Naomi couldn’t see us in the dark, she pushed my hand up to her stocking tops. She was wearing a very small g-string, and was completely shaved. I copped a feel and got my finger wet. That, and their combined perfumes gave me a rush. When we arrived, I had a raging hard-on. We lost them soon after. Pity in a way. She was a good looking woman and someone other than her husband was going to up there before the night was over.

The bigger of the two marquees was traditional blue and white stripes. Lots of seating inside, free bar, and a buffet being uncovered. A smaller open marquee nearby, sheltered the band, who were decked out in striped blazers and playing an old fashioned trad jazz set. But the centrepiece of the event was the dance area. Huge, genuine parquet flooring; presumably pegged into the grass. Everyone had made an effort with the costumes. There were more striped blazers and straw hats. One man sported a monocle. And there were more short dresses and black stockings on display than I’d ever seen in one place. Everybody was laughing. I’ve always said fancy dress is worth two drinks, in terms of losing inhibitions. The atmosphere was ripe with sexual possibilities.

It turned out this was a higher management sort of do. I only knew one of the hosts. The evening flowed gently into darkness. Every woman had a go at Black Bottom style dancing. Lots of high kicks with associated squeals, and deliberate flashing of their underwear. I got the impression Naomi’s slim legs were getting more attention than most.

Then suddenly, the heavens opened and everyone ran for cover. There was a crush in the marquee as they crammed in. The smaller one was doing its job, keeping the band dry, and they kept playing. Then all my theories about fancy dress were correct. A load of female revellers went back out onto the floor and continued dancing in the rain, getting soaked. They shrieked even louder when one of the girls fell; legs splayed and little black undies on show.

I went to the toilets, leaving Naomi dancing. Both urinals were occupied so I went in a stall. Once the urinals were unoccupied again, and I heard two more men come in. “You’re never going to believe what happened.” “Go on.” “I signed in Accounts for five thousand pounds to go and pick up the wine from the wholesaler. We have an account, but they’d offered a cash discount. When I came to pay, I found five thousand, five hundred in the envelope.” “They’re fucking hopeless in Accounts. You keep it mate. They’ll never even discover it’s missing. Spend it soon though and don’t put it in your bank, just in case.”

I was ready to leave but waited, as I didn’t want them to know the ‘theft’ had been overheard. “I know who I’d like to spend it on.” “Who?” “That little flapper girl.” “They’re nearly all little flapper girls!” “The one with the gangster in the white suit.” I grinned. That could only be me. “Her? She’s got no tits!” “I know, that’s why I fancy her. I reckon I could slip one up her arsehole, without bothering to take her knickers off! Or my trousers!” “Yeah, you’ve always been one for the ladies’ arses. Well go and talk to them. They might be into sharing.” “Tempting. Maybe I will.” I opened the door a crack to identify Naomi’s admirer. Grey pinstripe suit and spats.

I rejoined the throng. The rain was easing, but the parquet floor was still slippery. As I reached my target in spats, Naomi fell over with a scream. Her legs flew into the air, displaying her stockings and lacy undies. I thought the wine was probably as much to blame as the wet floor.

There was a communal grunt from some of the nearby guys and an ‘Ooh!’ from the girls. Her panties more French knickers than thong, and had ridden up her hips, forming a tiny wedgie. They were now see-through. She slid towards us, a puddle of water pooling around her crotch, offering a clear view. Not just a camel toe, but a nest of pubic hair, each side of the wedgie. I don’t think the overall effect could have been sexier if she’d been naked.

Her admirer shot forward and grabbed an arm as she skidded to a halt. He deftly got her to her feet and I could see she was out of it. Her eyes glazed as she held onto his arm to stop from falling again. He helped her to my side and I put my face close to hers. “You ok?” “Bit pissed. Better go home.” Her legs buckled. He pulled Naomi away from me and gently lowered her onto a chair. It was now or never. I looked straight at the guy and took a deep breath.

“Got a car?” I asked. “And a driver.” “Got five hundred pounds?” To his credit, he didn’t even flinch. “I could lay my hands on three hundred.” “I’ll take it and I need a few favours.” “Name them.” “A lift to the Forester’s Hotel. Help getting her undressed. And help checking everything under her knickers, in case she damaged something when she fell.” “I want her cunt and her arse.” “Her arse puts it up to four hundred. And I watch.” “Agreed.”

His driver waits in the car. Her admirer carries Naomi. Quite right too. He’s about to have one of the best fucks of his life, and end up a hundred quid ahead. We lie her face down on the bed, unzip her dress, and tug it off. “No bra.” “She doesn’t need one.” He puts the bundle of notes on the bedside table and strips of his clothes. A decent sized boner – similar to mine. I let him yank her soggy panties off. He lifts them to his face, inhales deeply and puts them on the bed next to her. His dick seems to grow another inch as he sniffs. He thumbs her buttocks open and stares at her tiny rosebud.

“Lovely arse!” The guy, his name is Saul, rolls her onto her back and gasps as her breasts do not even move. His dick jumps forward again, All right, maybe he’s a bit bigger than me. He gets on the bed and massages her tiny buds, muttering ‘Oh God!’. Then kisses her. We are both delighted when she responds with some reciprocal tongue action. He moves down to her nipples and sucks. She winces as he bites one too hard, but puts one hand on the back of his head, pushing him down harder. Her suspender belt and stockings are soaking, but he wants to leave them on. She moans loudly when he slips a finger into her cunt. “I’ll fetch some lubricant for her arse.” I offer.

As I return with the lube, he has two fingers busy up her cunt. He removes them and puts them in her mouth. No question of asking permission; he’s paid for this. She sucks greedily and her eyes flutter open briefly. He lifts her legs over his shoulders and parts her cunt lips, and she whispers ‘Yes!’. I quickly get undressed. He slides into her, and her hands come up and pull him down for some open-mouth kissing. He ploughs roughly into Naomi’s cunt, and shafts her, ramming her a lot harder than I do.

Now, he’s grabbing her hips and her with every thrust, getting his dick in as far as it will go. Naomi grips his buttocks and digs her nails in, as she pulls him in harder. The same way she does with me. Her eyes shoot open and she shouts ‘Oh! Oh!’ as her climax arrives. I confess to feeling a bit jealous. Drunk or sober, she has never climaxed this quickly with me. Can she see it’s not me? She probably doesn’t know who’s fucking her. Saul stops thrusting as she arches her back off the bed, and pulls his buttocks so hard her fingers go white. They both grunt and she collapses under him.

“Now I want your arsehole!” he told her. “Ooh, yes! Let me suck you clean first.” That’s the first time Naomi’s spoken to him. Surely she’ll remember this tomorrow; his voice is nothing like mine. She moans as he pulls his dick out of her mouth. “Pull your legs back and open up those arse cheeks.”

No ‘please’ just orders. I watch goggle-eyed as she complies, displaying her anus. He squeezes some lube onto one finger, pushes it up her, wriggling it around. She smiles. She’ll be getting some real cream soon. Saul repeats the process with two fingers, shoving them in all the way up to the last knuckle. His thumb moves across her clit like windscreen wipers. When he pulls his fingers out, there’s a slight brown streak on them. He picks up her panties and wipes his fingers off.

“I’ll keep these.” I nod. Her knickers are not worth four hundred pounds. He can have them. He’s spreading a little lube on his dick now. Somehow it contrives to look even bigger. Saul intends to fuck her arse, while she’s lying on her back. Good, it means I’ll get a better view. I grip my cock and hope I won’t cum too soon. I want my turn with her.

He positions his dick at the entrance to her greasy hole, and instructs her to bring her knees close together. It’s well oiled up there, but he obviously wants it to be tighter. Good for him. I watch fascinated, as she obeys. “You have to make a choice now.” he tells her. She looks into his eyes again. “How do you want me to do this? Gentle and romantic like a lover? Or hard enough to hurt you?” She doesn’t even think about it. “Fuck my arsehole as hard as you can! Make me cry!”

He shoves his dick all the way into her arse in one go. As his balls slap against her buttocks, her head shoots back on the pillow and she screams ‘Ow!’. That definitely hurt. But what comes next is worse, or possibly better. Saul fucks her like a man who hates her. He forces her knees back onto her chest so hard, her tiny tits get squashed into her ribs and she gasps for breath. There are eight bright red arcs on his buttocks where she’s dug her nails in. It looks as if he’s taking his revenge for that.

It’s the most painful looking fuck I’ve ever seen. And through it all, Naomi kept her hands down there, pulling her cheeks open. It only lasts six or seven minutes. Still crying, Naomi brings her hands up to his face and pulls him down for a kiss. Her tears mingled with their spit as they fiercely do the tongue action again. A minute of this seems to be the trigger for his climax. He lifts his head to the ceiling for a final ‘Argh!’ and finally finishes. As he shoots his load, Naomi is weeping softly.

I stare at his twitching balls and his throbbing dick, as he empties into her bowels. Incredibly her cries die away as he fills her, though I swear she was in pain. But now she’s murmuring ‘Mm, mm’ in ecstasy. Like she does with me. But is this how she’d prefer to be treated? Something I should explore in the future. He pulls out as roughly as he entered and wipes his dick on her panties. A stream of cum flows from her arse, puddling onto the duvet.

He dresses and goes to the door. “That’s the best arse fuck I’ve had. Actually, I’d have given the full five hundred for it.” It’s a compliment I suppose, but I’m in no mood to put up with this arrogant prick’s sneering. “Well I always get it for free, but would have let you have it for two.” I sneer back. He snorts. “And you reckon in the morning, she’ll think it was you?” “That’s right.”

“Well if she tells you that, she’s lying. She is a genuine slut and knows exactly who fucked her. And if you can’t see that, you’re a bigger cunt than you look!” He leaves. slamming the door. Who cares what he thinks? Right now I want that arse while it’s still wet. So I fuck her too – sloppy seconds. It’s fantastic of course; anal sex always is. But not nearly as tight as usual.

Next day, as expected, Naomi knew nothing about our visitor. She recalled falling over on the dancefloor and thought we came back to the hotel in a taxi. “God, you must have given my bottom a good seeing to last night, you animal! It’s still running down my legs!”

I noticed it was back to being called her bottom now. Last night it had been ‘Fuck my arsehole as hard as you can! Make me cry!’. I wasn’t quite sure what to make of it all. “Have you seen my knickers? They’re my best pair.” “Sorry babe, I have a confession. We got started on the way home. The taxi driver is probably wanking off into them this morning! I’ll but you some new ones.” (I can certainly afford to!)

So, I’d always wanted to watch another bloke give her a good shafting, and now it had happened. She still objected to the idea in principle, so didn’t need to know And I decided to keep quiet about the money too. I might be behaving like a pimp, but Naomi was no whore. A bit sluttish when she was drunk, but no whore.

She works in the sales department of a large company and, in the spring, they landed their biggest ever overseas contract. A Friday night party was organised, to be held on their own premises. They have a nice bar and a massive conference room. Actually, I’d drunk with her in that bar a few times, but was not invited to that party. It would just be sales staff and upper management, and some of their counterparts from Dubai.

We had a long lingering kiss in the company carpark. “OK, you go and have fun.” I said. “Wait a moment, you’ve smeared my lipstick.” She reapplied it, while I went round to the passenger side, and opened the door. Wonderful flash of those slim legs as she got out. She was wearing a cocktail style dress which flared from her tiny waist. A classic little black dress, except it was a rich burgundy colour. Black hold-up stockings under it; well it was the weekend.

“Thanks for running me here Jamie. Your car seems to be running better.” “Yeah, I got all the problems fixed,” (You don’t know it but your arse paid for that!) “It’s a pity we aren’t allowed to invite partners.” “No problem, babe. Feel free to flirt a little, but don’t drink too much and fall asleep in toilets!” She laughed. “I’ll be careful. You’ll be here at eleven to pick me up?” “Of course.” She ran up the steps, and I noticed a couple of security guards open the doors for her. The company have probably laid on extra staff to impress their Arab guests.

Cars were already leaving when I returned, but I got to a parking spot at five to eleven. A few people were still coming out in dribs and drabs. By ten past, there had been no sign of her and all was quiet. At twenty past, I was about to go looking when two women came out, one of them was wearing a short cocktail dress and staggering somewhat. Naomi had obviously overdone it again. The other woman was a little taller, with shoulder-length fair hair, and a long white dress. They melted back into the shadows and Naomi disappeared from view behind the blonde. It looked as if they were kissing. I couldn’t believe my eyes. She had never shown the slightest tendency towards gay or bi-sexual feelings before.

I wind down the window to get a better view. No doubt about it, that’s a long kiss. I start to get a hard-on. as a hand, clad in a long white sleeve, drops to the hem of Naomi’s dress. It moves, unhindered, up between her legs. Not bothering with her tits then. The hand stops when it gets to her crotch. It disappears from view under her dress. Someone is having a good feel. What concerns me is Naomi losing control. I’m not sure what to do. The last thing I need is for them to take off somewhere, leaving me high and dry. She’s drunk again, so that might well happen. If she believes that’s me kissing her, she might forget the real Jamie is here. But now the hand is removed and her dress falls back into place. Naomi lurches away from the wall but stumbles on the top step. The blonde jumps forward to steady her. Another surprise. Not a long white dress, an Arab robe. Not blonde hair, a head-dress. It looks very pale in this light. I get out as they approach.

“Ah, you must be Jamie.” says her dark helper. “And you must be some randy Saudi, who’s been kissing her and feeling her up!” “That’s correct.” I’m taken aback by his brazen admission. But then, he is a Muslim, so women are second-class citizens. Especially western women. I bundle Naomi into the back seat, so she can lie down. He stands next to me, blatantly looking up her dress. Hardly surprising, I am too.

“I want to fuck her, but she said she must go home with you. You are a lucky man.” “I guess so.” “I will pay you eight hundred pounds to fuck her. A thousand to fuck her ass. Cash.” He pronounces it the American way; like mass, not grass. However, it’s pronounced, it’s doubled in value! And I can’t help but notice it’s pay me cash, not her. She must be my property of course. I have nearly enough money for the kitchen extension, and a decision to make.

“Twelve hundred pounds for her arse. You fuck her at my house, and you only have one hour.” “Agreed. I will need you stop at a cashpoint. And when I am done with her, I need you call a taxi.” When he’s done with her. “Deal.” So much money for such a small thing. And he agrees so readily, I wonder if I could have got more.

We arrive at my house and he climbs out of the back of the car. One hand supporting the staggering Naomi, and the other passing me her panties. I’d been able to hear the activity in the back of the car, but thought it was only groping and kissing. Her panties were so wet, I could have wrung them out. Still, I like her to get excited; even if she doesn’t realise who’s making her that way. We went inside and he threw her unceremoniously onto the settee.

“I hope she is not unconscious.” “No. She will participate willingly. She just won’t remember much in the morning.” “Excellent. In a few weeks, I will not remember her.” Nice. It would seem I’m the only one who will remember tonight. It won’t hurt to take a few photos though. I get my mobile phone out.

The Arab, I never do get his name, drags her forward until her arse is over the edge of the settee. He removes his robe. There’s no sign of any underwear, but I can’t see his dick yet. Probably not much to see, he’s quite short. He places a cushion under each knee and orders her to take her thong off. He tells Naomi to put her hands behind her knees and lift them back to her shoulders. This is a replay of Saul. Once they reach her face, she pulls them apart without being told. He placed his thumbs either side of her vagina, and opens her lips wide. He does it with such force, it looks wider than it is long. I wince in sympathy. That must hurt, but she doesn’t seem to notice – just moans. And that sounds more like pleasure than pain. “Good. Small, and pink. She will enjoy this very much.”

His dick springs into view, big and black. Very big. Yet another ‘customer’ who’s bigger than me. Ah well. If I want to watch my girl get fucked by another man, there’s not much point in wishing for a small one. It’s darker than the rest of him, black, rather brown, and it’s curved. I guess about ten inches long, and the last three inches curve back.

He moves his thumbs to her vulva and forces them even farther apart. Her entire cunt is now stretched painfully. She gives a pathetic little whimper, which turns into a full-blooded scream as he plunged into her. No build up. He lifts himself off the cushions to enter her, accommodating the curve of his dick. But now he’s fucking her, he settles back onto his knees, gripping the tops of her thighs with such force, I suspect there will be bruising.