Anne Obeys Reluctantly

"I think she is completely loyal to her dildo but I think she could use a good dose of one or more thick, hard, stiff cocks. I'd love to see her get it that way. We have no kids, no financial problems. In reality, I don't screw around and I am almost positive she never has although she is very attractive and I'm sure could get fucked easily if she wanted it. She must know that I jerk off when I want sex and I have fantasies about her getting fucked, sometimes with me watching (either with permission or being made to) or sometimes being gang-banged, starting out resisting and ending up begging for more."

*

With her husbands words still strong in my head I watched Anne continue to slip the dildo in and out of her pussy. Her cheeks burned with shame as I watched but she did it nonetheless, I think she believed me when I said I would open the blinds on time whether she was done or not. She certainly knew what to do, that could not be argued, she was slipping that fake cock up into her with some pretty deft movements and at some unusual angles and from the faces and quiet noises she was making I guessed she would orgasm well before time, it would be fun to watch. Her hand got faster then slower, harder then softer and I could see the sides of the dildo were slick and shiny with her juices when I called for her to stop.

"Stop! Stop Anne. Get up on top of your desk, you're going to be nice and on display for me when you cum and I don't want you stopping your juices coming out either, just let them flow on whatever's on your desk bitch."

Anne shot me as hateful a glance as you could imagine but I just flashed my pearly whites back at her and pointed her up to her table. It was quite the journey for her, what with her almost on the verge of climaxing and holding the dildo half in her pussy as she clambered up her office chair to squat on top of her cluttered desk. She looked at the door again as if it would swing open at any moment but of course it was still locked.

I casually walked to the door seeing as she was so interested in it and clicked it off being locked and smiled at her.

"Better make it fast, eh?"

She wanted to curse me out but of course couldn't waste time doing that and as I leaned against the door I admired her form with a vibrator. She was, as her husband had told me, quite the expert with a lump of plastic. She managed to simultaneously rub her clit with the dildo while spearing it deep within her and I am sure her technique and the risky situation she was in brought her to climax very quickly. I smiled as she had to bite her lip to stifle and exclamation as she burst forth and sprayed hot, clear cum all over her thighs and the papers scattered below her. I toyed with the door and the lead to the blinds but that was just to play with her mind, she had done what I had asked and once she had got down and licked her dildo clean (at my request and again much to her obvious distaste) I bid her my leave and told her to make her excuse for tomorrow because I would be picking her up at 4pm for our next adventure.

*

Pussy Galore's Pole Cat's is just the kind of establishment it sounds like – a cheap, tacky strip club very nearly in the wrong part of town. I've enjoyed quite a few good nights in there and a good few of my marks have endured a bad few nights in there. It's not my first choice as a strip joint, there are places with a better quality of slut but it does enjoy one glorious advantage – amateur night. Which is something I hadn't exactly told Anne as I drove into the parking lot having picked her up straight from work.

Her nose turned up when she saw the gaudy neon sign above Pussy's and I genuinely think she didn't realise what type of club it was immediately, just that is was a low level place that scum hung about in and I guess that fitted in fine with her opinion of me. I just shook my head and chuckled to myself, knowing that she would have a serious attitude adjustment by the end of the night about where she really stood in the scheme of things.

In her expensive business suit Anne was way overdressed but then that wasn't going to be a problem for too long, was it?

Anne moaned and whined as I opened her car door and led her into the gloom that was the entrance area of the club and positively groaned when a trashy blonde behind the desk asked her to pay for us to get in (you didn't think I would pay did you?). I think she was beginning to figure out what this place was once we got in the door and entered the main room and the mixture of smoke, music and lust that lives on in any strip club. It was early yet and there were not many girls on and I led Anne to the bar and demanded she buy us a drink as I set about explaining what she would be doing that night.

"Are you having fun so far Anne? No, oh well. Listen up bitch, because things get really fun from here on, you know I did a bit of digging and from what I gathered that insider stuff you were doing could even see you in jail if it were discovered, something about fraud? That would be too bad because a nice dame like you could really suffer if you got the wrong cell-mate, you dig? Now we both know that ain't gonna happen Anne because all you got to do is what I tell you to and you're doing so well so far so lets nor let that standard drop. Now as for tonight...."

*

I let her buy three drinks at the bar. Dutch courage, I guess. It made no difference to me, all it meant was that the club got progressively busier but Anne didn't seem to figure that part out. Maybe it was the drink or maybe she was still recovering from being given her task. She was a highly paid, high powered executive on a huge salary but something told me this would be the hardest $100 she had ever earned. I was watching her as she queued with three other 'amateur strippers', waiting for their turn to get up on stage and entertain the clubs patrons (there must have been fifty or so in the club by then and most of them would never get to see a classy woman like Anne in the nude in their life) but once she was through the door leading up to the stage I moved back through the gloom to have a quick conversation with James, her husband who was nicely hidden but well able to watch his wife's efforts. He passed me over a drink and I thanked him before moving through a group of guys to get nice and close up on the stage they set aside for the amateurs.

The first of the amateurs was a young slut called Karen (according to the DJ), she looked about 21 and was pretty cute though had a bit too much puppy fat for my liking and had that look about her that told you she was doing this for the money but was actually enjoying it too. As I sat mere inches from Karen's wide open legs and perused her freshly shaven young pussy I thought she could well have a future in stripping and turning tricks if she lost a little weight. But if Karen looked like she was enjoying herself there was no way you could say that about Anne. She looked like she wanted to be just about anywhere on earth right then than up on that mini stage / podium hanging onto the pole.

She looked so out of place up there, dressed as she was in her designer suit, her real expensive shoes, jewellery and haircut and not like any of the other girls. But rather than turning the guys off, her reluctance seemed to draw and even larger crowd around her podium that seemed to sense something rather different and special was going on here.

For a woman so used to being in control this must have been terrible, she tried, bless her to get into the music and sway her hips and body but she was so damn awkward up there and her dancing was excruciatingly bad. So bad that more guys were checking her out! She got herself in a bit of a mess getting her suit jacket off and dropped it at her feet as her blouse was fully revealed and those enticing breasts were hinted at below. In all it was probably the least sexy strip tease you would ever see in an establishment like this yet, for all together different reasons it was a complete turn on. To watch this woman reluctantly degrade herself (in her eyes at least) in front of a bunch of hicks and grease monkeys tossing dollar notes at her as she stripped was giving me a hard on to die for as I watched and I could only imagine her husband was ten times worse by that point.

After much fumbling and stripping she was down to her white silk bra and panties and I could not wait until they went. By this time she had found something approaching to rhythm and maybe the booze was kicking in because she was getting better. I could visibly see her take a deep breath before reaching her arms behind her back to undo her bra and slowly let it slide her forearms and exposing her pert little titties, so pale against her tan. Still that got a real cheer from the guys and they waited for her to finish the show and expose herself completely. She looked at me making one last hopeless plea but I just smiled and held up a rolled up five dollar note and nodded for her to lose her panties.

My cock stiffened as I watched Anne finish the job, peeling her panties off and swaying before the crowd completely naked, I could see her pale cheeks blush furiously and got off on the knowledge that this had to be totally humiliating for her to have done this – to strip completely naked in public. She finished her set by making sure all the guys around her podium got a great view of her entire body and at my insistence she opened her long legs nice and wide for everybody to a great cheer. I also told her to crawl around the podium on hands and knees and pick up all the five and ten dollar bills using just her teeth which was something that obviously made more than just me hard judging by the comments she goy. I also had an idea what I wanted to do with Anne next and slid away for a second to whisper to her hidden husband and tell him what I planned to do later, he just smiled at me and easily agreed.

Minutes later Anne emerged hurriedly from the backstage area and made her way over to me and hissed.

"Are we done now? Have you seen enough? Humiliated me enough? Can we go now?"

I nodded and demanded the cash that she had made dancing, no way I was letting her keep it.

"Yep, we're done in here, let's go."

I led Anne out the front entrance, right past all the clubs patrons who had seen her naked body. I loved the looks on their faces as this smartly dressed business woman walked past them and they recognised her as the recently departed reluctant stripper. Anne scowled at them and gave them as much disdain as her face could muster but I kept her moving and soon we were back at the car in the now darkened parking lot. She grabbed the car's handle to get in but I grasped her wrist and spun her around to face me, our bodies mere inches apart.

"Not so fast Annie! You've got me all excited, see (here I deliberately poked my erection hard against her thigh) so I need to do something about it. Get round to the front of the car and bend over it and pull that sexy business skirt of yours up!"

Her temper showed and she made to protest but one look into my harsh eyes stopped her and like a spoiled child she stomped around the car in the gloom and laid herself prone across it in the most inviting of positions. I did not hesitate, I strode around behind her and easily released my pulsing, stiff cock from her trousers and slid my had up her hitched up skirt and gripped the thin fabric of her panties. I yanked them aside and thrust two fingers at her pussy lips and was delighted to find them soaking wet – the bitch may have hated her humiliation but she could not hide the fact that was aroused by this situation.

I removed my fingers and easily slipped my hard cock in between her legs and reached forward to hold her hands tightly behind her back as I began to fuck her across the bonnet. This was past being business now, right here in this secluded area of the Club's car park, where I could look up and watch guys enter and leave while I thrust harder and hard into Anne from behind and she grunts and slides forward then back on the shiny metal. It is almost too much for me to release her hands and dig into my jacket for a scarf and to reach forward, grab her blonde hair and wrap the scarf tightly around her eyes so she cannot see, all the while I continue to pound into her pussy with my dick.

Her husband can conceal himself no longer and as soon as the blindfold is positioned he emerges from the shadows and pulls his own cock from his trousers and stands by the grill next to me. I grab Anne's hands and guide her to her left until James can shove his meat into his wife's unsuspecting mouth. And he experiences his first oral sex in so long. Anne's grunts became swiftly muffled as her mouth was filled and for a few minutes the only noise was that of we three's bodies as we moved to a hard rhythm. James had to almost bite his hand to keep himself quiet as he came, he grunted and squeezed his eyes shut and started to shake and filled his wife's mouth with his cum. As he shook the last drops on her blindfolded face I waved him away as I came myself, flooding her tight pussy with my own sperm.

Finally Anne sprawled off my cock and against the car, she tore the scarf from her eyes but her husband was long gone and she searched the gloomy lot for my accomplice. But he was gone. Her hand wiped at her lips, disgusted.

"Who was that?"

I wagged my finger mockingly at her.

"Perhaps you shall find out, perhaps not. We will see but first you have half a week to go before I and my client are finished with you. So go home and ready yourself for tomorrow. Who knows what it will bring!"

*

Who knows indeed? Well I do and I can tell you that the rest of the week will bring Anne down into the murky, perverted world of lesbian domination, watersports and gang bangs and much, much more. Until then dear reader be sure to vote and leave comments and feedback and please be forthcoming with ideas for Anne and her husband, who desired and requested this story