My Anna

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OpenMouth
OpenMouth
202 Followers

She had told me at length of her hope to eventually study psychology- this did not surprise me in the least, as the subject obviously fascinated her, especially combined with sex. I thought this would be a way into us talking about our strange relationship.

"Anna," I ask her, "live with me. Share my new place!"

My business interests had taken off recently, and I found I could afford a penthouse apartment in a recently-completed block. I showed her the promotional shots and watched her eyes widen with excitement. I knew she couldn't hold off for long.

"Here's the plan. You live with me, enrol on a psychology foundation course at the university. I'll never cramp you..."

"But..."

"...And I don't care what you were when I met you! I love you. You excite me beyond belief. You are gorgeous and clever and funny..."

She descends upon me, kissing and caressing, pulling me onto the bed. "Just tell me what I can do for you, any time, day or night baby." The sincerity in her eyes tells me all I need to know.

*****

Our new apartment is spacious and opulent, offering the space for us to be apart when I work, or Anna studies. She has a natural probing mind and an aptitude for language which help her immensely and as she progresses through her course, and soon we find our fascination with the psychology of sexual desire to be at the heart of our physical relationship. She says she will make this a major subject for her degree course; maybe even her life's work!

I am happy to help, and we indulge ourselves completely. She enjoys being 'Doctor Anna' on occasion, complete with crisp white nurse's blouse (revealingly open, of course) and spectacles. She sits behind or on her desk, chewing her pencil and asking frank questions about my fantasies and desires, sometimes taking my pulse or blood pressure or writing down notes.

"Veryinteresting..." she says, scribbling notes with wide eyes as I blushingly reveal at length a certain fantasy that has always made my heart race.

She gasps, and purrs "Would you like to try that?"

I nod.

"Would you like to try thatnow?" She asks, unsmiling and unblinking. "OK, c'mon."

Anna has long ago overcome that initial shyness and hesitation that a 'nice girl' uses to score points. Within seconds she has lit a cigarette, which never fails to get me interested. Within minutes I am in the fantasy; a fairly benign one but something I would only ever reveal to her.

I am naked, feet apart and hands on her desk. On her large computer screen she has started a movie clip playing; I watch in increasing arousal as an impossibly-cute young blonde is double ended by two muscular and hung black men. I hear the squirt of lube and feel the coldness as Anna's fingers expertly work it into my anus.

"Relax," she breathes smokily into my ear, and I feel that acute tightness as I involuntarily close up against her probing finger. Eventually, I loosen enough to accept her gentle two- and three-fingered thrusts.

Continuing to rhythmically penetrate me with one hand, she opens her desks bottom drawer. I gasp as she brings out an enormous, black rubber dildo, which must be nearly a foot long.

My heart misses a beat, the mere sight of it causing me to drip precum. I realise I am not erect, as I relax for Anna's fingers. "Oh, god..."

"OK," she says, glancing at her notes. "Fucked like a slut, it says, by a woman. While you watch black cock porn. Open wide..."

"Oh, g..." I manage, as the head starts to penetrate me, feeling impossibly large.

She giggles. "Only the head today, darling. But you're going to be a bitch for me and my big, black cock from now on..."

She applies pressure gently but insistently until I feel myself swallow the massive head; the realisation alone causing intense waves of pleasure which are increased tenfold as she reaches between my thighs, clasping my dripping, flaccid cock between her thumb and index finger. She starts to stretch me down and I stiffen, clamping the dildo even harder with my anus.

I am erect now, and she wanks me off briskly and efficiently, my cum flowing and splatting to the hardwood floor.

I scream silently, laughing and as she slowly withdraws the tool, a fall onto a nearby sofa. Unsurprisingly, she lights a cigarette and blows smoke towards me with a look of bitchy satisfaction.

"Well, well," she says admiringly. "Enjoyed that, didn't you? I think you're going to be a proper little anal whore..."

*****

In the subsequent days I struggle with my conscience. I had left Anna with some reluctance but felt she was uneasy despite another night of protracted lovemaking. I sense she is contemplating the film noir futility of such an obviously doomed relationship and I know we must overcome that substantial hurdle.

The similarities with the film Pretty Woman were glaringly obvious also- a wonderful, vivacious girl, getting by the best way she can, falls for a (slightly) older, successful man. But had this ever worked out well in real life? The fact that this girl had never asked for anything other than her fee, indeed even remained dignified and aloof on occasion, reinforced my need to know...

I had to convince her that a 'conventional' relationship was not interesting to me, that her personality, her past were vital to us. Her vast sexual experience felt like superiority to me; knowing what she had done would always remain arousing. I explained all this at length the following weekend. I went as far as to suggest she should keep dating, which we soon pinned down to the idea of her taking another regular lover. This would have many benefits to us- I would ask the reader to suspend judgement at this point; such an arrangement may seem rather bizarre and suffice to say you will either find the subject erotic or quite the opposite!

1. I found the prospect of her dressing and making up to have sex with another man to be electrifying. Indeed, I could think of no better way for her to keep me hot for her.

2. We believed such an arrangement would give her a measure of- perhaps even overall- control in the relationship. This would help to build Anna's self-esteem and would have the delicious side-effect of adding the possibility of a female domination situation arising...

She told me of one of her 'regulars,' a black guy called Don, with whom she'd had something of an understanding. He was good to her, and being married (and working away from home from Monday to Friday), was clean and very discrete. She said he was open minded and had a good sense of humour as well, and would possibly be interested in some kind of 'unorthodox' set up...

I admit my heart leapt at this news; while not wanting to appear racist I had imagined this imaginary lover to be a black man and a well-endowed one, at that- Anna confirmed this was the case! The more we discussed the subject, the more we couldn't stop touching each other and ourselves. I asked what she thought would be the best way to broach the subject; she said to trust her, honesty would work. "I happen to have this rich boyfriend," she practiced, "who isenormouslyturned on by the thought of me getting a regular fucking by a big, black man. Now, here's the deal- you promise me you'll only have sex with your wife and me. You get yourself tested and so will we. Then we play, every week, and it won't cost you a penny! Either I come to you or you can come 'round to our flat, don't worry, it's a big flat!"

She didn't waste any time, sorting it with that businesslike, matter-of-fact efficiency of hers. Don was more than willing and they started putting things into place the next week. As he was a blood donor, a fresh test was very quick, and we were able to go to a private clinic for a quick, discrete test also. So within a week or so, Anna came home in a taxi at 3am for the first time, fresh from several hours of attention from Don. I opened the door to find her standing in a very short dress, stockings and raincoat with her hands on her hips and a cigarette hanging from her lips. I held the door open, and she took a drag, clomping slowly past me and exhaling creamily in my direction.

'Wow!' This was all I could think of to say as she lay on the bed and showed herself off. I'd never seen a woman's sexual organs so inflamed and engorged; she virtually glowed with use and the heat and the smell of Don's spunk just made me think one word- Goddess.

*****

Over the subsequent months we develop this new dimension. Initially, we enjoy the simple pleasure of me using my tongue on her when she gets home, licking out every trace of her lover. Sometimes she'd come home with no knickers and we'd meet friends for a drink- I'd sneakily slide a finger into her below the table and smear the slimy cum around her lips while we kissed, innocuously.

Next came the video camera- Don agreed to this if his face did not appear on the clips so she'd set up the camera for a closeup of her face while she sucked him, all the while looking at the lens. Sometimes she'd email the clips to me then arrive home to find me enjoying them, other times she'd wank me while I watched them, or use a black dildo on me- she was convinced I wanted that black cock for myself, which we talked about at length. I did have an enormous envy for her big, pneumatic body; I imagined how it would feel to stride down the road in a floaty dress and heels, boobs quivering with every step.

I'd help her dress to go and meet him- sometimes smartly, in a pinstripe suit with a silk scarf, occasionally trashy with a short skirt and hold ups. We decided she'd invite him back so I could sample his spunk within seconds of him depositing it in her- I heard him exit, and barely giving her time to light a cigarette I was between her thighs and drinking rivers of hot cum from her as she purred and smoked.

We used ever-bigger black dildos in the bedroom- both of us would enjoy them in turn. She'd enjoy dressing me in stockings, suspenders and heels with just a pair of frilly knickers between my lubed anus and an 18" black rubber dildo; I'd love her to suck on one as I fucked her, or just watch her stretching herself round the bulbous head, as she told me what a slut she'd been with Don that week, letting him assfuck her all the way with video evidence.

With each new sexual adventure we talked about refinements, fantasized about how far we could go. We talked about setting up a webcam to allow me to watch her in real time, blowing smoke at the camera while getting fucked from behind, but we both knew we wouldn't be happy until I could be there in person, watching Don fuck her in front of me. Anna took this fantasy a stage further, suggesting she discuss with him the possibility of him assfucking me while she watched! I imagined how it would feel, his rock-hard length flooding me with hot spunk as she sat and smoked, a look of satisfaction on her face.

*****

We loved to relax together in the bath, discussing a recent session or two. We had two baths, arranged so we could look at each other as we talked.

From the earliest days of our relationship, she knew I loved watching her smoke. She said that before we met, she had been aware of men who obviously became aroused at this. She suspected that they had worthy, clean-living wives who would never understand such a fetish.

She was amazed when she discovered the depth of my fetish, just how much time I spent fantasizing. Over the next few months, we really had fun with her style; I'd tell her of her little mannerisms and ask her to try different ones, usually as we bathed. Already a supremely stylish and feminine smoker, we took this to the limit. She would hold her cigarette delicately between the tips of her fingers, inches from her lips between drags, slowly parting her lips to accept the filter and spreading her fingers as she let her mouth take over. After a deep drag lasting several seconds, she would open her mouth momentarily to treat the observer to the sight of the dense, almost liquid smoke swirl inside, before taking it into her lungs. Tossing her hair from her eyes was a nice touch, before exhaling endlessly. She could make the exhale go on and on by pursing her lips quite tightly, although I preferred her exhaling more messily with a looser pout.

Some aspects of her style were unashamedly showing off. As if her long legs, blond hair, big boobs and plump, sensual lips were not sufficient to draw attention! She said she could almost hear the bitchy comments from other women on a night out- 'look at her. Silly cow, fag hanging out of her mouth, who does she think she is?'- but we both knew, and both enjoyed, that men were looking at her.

She would sit on a bar stool, knees crossed, blowing perfectly formed rings into the air. She would use any excuse for letting the cigarette dangle; tidying her handbag or primping her hair in her compact mirror like a '40s screen diva. She would unashamedly walk down the street in this manner holding her bag and car keys. I liked it best when she was dressed smartly or demurely as the visual impact was so much stronger in a suit or pretty summer dress. Occasionally, as people in our party became slightly inebriated, she would start to openly blow smoke in my face, giggling and wafting her hand about as she apologised. Our friends assumed this to be an endearing little habit of hers as she became tipsy, never suspecting my heart pounding in my chest. On one occasion I pretended to tell her off; everyone laughed when she replied with "I do it 'cos you fucking like it, you slut!" I like to think at least one of the other girls, a slim brunette neighbour, understood what was happening.

Anna meticulously looked after her skin, cleansing and moisturising every night at bedtime, after her shower. I admitted to her, however, that I liked her a little more 'fragrant' occasionally... This usually took the following form- she would return from Don's, smoking in her car on the way home, pour herself a glass of red wine, strip down to her stockings and panties, apply a thick coat of Arden lipstick and climb into bed with me. Her breath would be thick with wine and cigarettes as she smeared me with her beautiful, fresh lipstick; I'd nuzzle between her breasts and smell her sweat and Obsession, trailing ever lower where the heady aroma of her sex would almost paralyse me. Venturing a tongue inside her would remind me that just half an hour earlier another man had enjoyed her, sending shivers down my spine and magnifying my excitement tenfold.

*****

We are planning a wedding! Yes, it's true, but as it will be an 'unconventional' wedding, the plans may take some time...

We will have to find a registrar who is willing to indulge our small idiosyncrasies; for instance we want a transparent white wedding dress with no knickers, no bra or a simple braless corset underneath. We want Anna in thick red lipstick and smoking throughout the service; I want her to stand opposite me with a hand on her hip, blowing smoke into my face while we say our vows. Most importantly, we want Don to fuck her in all three holes in the shortest possible time before the ceremony, so that his spunk is quite literally running down her legs from her anus and cunt during the ceremony. Ideally, though we believe this would be stretching things a bit far, she should have visible fresh spunk around her mouth as well.

We are also discussing the possibility of her coming off the pill briefly before; we love the idea of her being fucked while receptive by another man on her wedding day. We think this will remain a fantasy, however!

Our wedding night will hopefully be out of the ordinary, too- being fucked senseless in her wedding dress by three black guys while I watch is the favourite so far, but it may be difficult to convince Don. He gets a bit possessive about her sometimes...

OpenMouth
OpenMouth
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SimplyMe23SimplyMe23over 11 years ago
beautifully written.

The story has body, life, and great substance. I could feel the sordid love that he felt that he knew was lonliness and opened himself to her world, submitting himself in the name of "obsession". I think Miss Anna will be flipping the script and merely going from student to teacher, prostitute to pimp.

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