Anne Obeys Reluctantly

I watched Anne get out of her Executive's car and stride purposefully towards the hotel entrance, she was every bit the beautiful, professional, confident woman her husband, James had told me she was. She was a bit older than I was used to, I tend to like them in their mid to late twenties but for a woman over 40 she did not look bad at all as she stepped into the revolving door of the hotel and approached the reception desk. I was sat in one of the luxurious leather armchairs in the bar just off to the side of the reception area with an uninterrupted view of Anne's movements, I had a paper in my hand but that was merely a prop to hide my observation. She was dressed as instructed, that was a good start, it's always good when they do what they are told, I find. She wore a smart business suit and expensive looking white blouse together with a daringly short business skirt, its hem was a good six inches above her knees and her sheer black stockings were enticingly visible beneath.

She looked confident as she spoke to the receptionist and seconds later took the room key from him and strutted over the polished floor on her high heels to the elevator to reach the room I had booked for her. As she disappeared inside the metal doors I smiled and patted my erection through my trousers and thought about the fact that in under ten minutes that smart, confident business woman would have her mouth stuffed with my rock hard dick while my big hairy balls bounced off her chin.

*

"Her name is Anne. She is hardly a dog and I imagine there are plenty of guys who would love to fuck her. She is 40 years old but can easily pass for 10 years younger, 5 1/2 feet tall, usually within a pound of 120 pounds, plus or minus. She exercises and is quite trim. She has green eyes, a wide mouth with beautiful teeth, a dimple in her chin, is a natural sun-bleached blonde and wears her hair in bangs with it cut up in back and longer on the sides with the hairline following her chin. Her figure: 34C, 24, 35 hips. Her nipples are small and pink. She shaves her pussy to a small inverted triangle and her hair is light brown (no sun).

She is British, very smart, and has a graduate degree in international business and works full time as a Senior Director with a team of people reporting to her. The company is headquartered outside Boston (where we live) so she works from a home office and travels to headquarters, usually once a month. She also travels to business partners internationally and has been all over. She dresses well in business situations in (expensive) skirts, jackets, blouses, heels and often wears either pearls or a silk scarf. At home she likes jeans and pull-over polo shirts and sandals. She loves to cook, read, and listen to classical music and opera. We live in a historic district of a lovely city and can drive to town for the symphony, opera, ballet, or have dinner out which we do once a week. "

*

I don't know what I'd call myself, I suppose the nearest things would be a hitman or a bounty hunter, both in a sexual sense, I fuck and screw people to order, whether they like it or not. I don't know how James heard about me, all my business (and I do maybe 12 jobs a year) are from word of mouth and I decide whether I want to take the job or not. This one I was sceptical about because of Anne's age but when I saw a picture of her and heard from her shunned husband of her particular sexual peccadillo's and took possession of his carefully gathered evidence against her I would have been a fool not to take the contract. It was almost a gift horse.

The set up was straightforward enough, James had given me concrete evidence of Anne's apparent insider trading and wanted me to do my thing with her. I told him all I would do and rather than balk he actually suggested wilder, kinkier stuff to me. Which was fine, as long as he paid the bills I was more than happy to comply. He had insisted on giving me the reasons why he wanted me to do this but to be honest I didn't care – I am motivated by money and sex and not necessarily in that order. Anyway, a quick phonecall and e-mail to Anne convinced her I had sufficient evidence to harm her career if not her liberty was enough to convince her to play ball with me, although like most marks I think she was expecting the penalty for her indiscretions to by financial rather than physical. It would be fun setting her right, it always was.

Which is why she was in room 512 of this hotel right now waiting to meet me. She might have figured to set me up but I haven't lasted this long in the game without knowing some tricks so ten minutes after Anne departed in the elevator I followed her up and was soon knocking at the door. She opened it sharply but I was holding on to the handle from outside and with just a small gap between door and frame passed a black cloth hood to her and told her to go over to the window and put it on her head before I came in. She made to argue but I soon pointed out to her that she wasn't in a position to unless she wanted call my bluff and soon enough she was at the window, standing there, wearing the hood as I entered the room and closed the door behind me. I searched her bag and coat pockets for anything that would suggest being double-crossed though I doubted it, not with evidence she knew I had. I didn't hang around, I wasn't getting paid by the hour.

"Listen up bitch, I don't want to have to repeat myself and this is actually really straightforward, especially for a smart woman like you."

She gave a groan under the hood and swayed a little as if she couldn't believe this was happening.

"I don't want money from you, OK. So you can rest easy on that, I don't need it. What I want is your obedience for the next week. And I mean sexual obedience. You're going to do what I say and when I say it and let me use that fine body of yours as I see fit to get you out of this situation. You do that and you get this paperwork and all the copies I made. One week. We do something each day and you do it exactly like I say. It's easy. What do you say?"

She deliberated and tried to talk her way out of it but we both knew she was going to do it, all she had to do to avoid all the danger and risk of being exposed as a criminal who was defrauding her own employers was submit to be my sex slave for the next week. Her compliance was as inevitable as it was enjoyable and it was not long before she was reluctantly agreeing to my terms.

"Take the hood off bitch we can make this day one!"

*

"The first years Anne and I were married we had conventional sex using birth control pills. One night she said she wanted to get off the pill and neither of us liked the idea of condoms. She first admitted that before marriage she used to masturbate a lot, sometimes several times a day. I admitted that I also love to play with myself and, in fact, prefer it to fucking. So we agreed to try different ways to cum and not fuck for a month. The night that she used her last birth control pill was the last time we fucked. I couldn't tell you the date of our last fuck, but we have lived here for 20 years and we have never fucked here. "

*

It never fails to turn me on having a woman, naked, kneeling at my feet sure in the knowledge she is about to orally pleasure me, especially if she is reluctant about it. You can see in their eyes that they hate and despise you and are turning the thought over in their mind of whether to bite your dick off, but they never would. It's they last bit of power they have down there, but my targets, especially one fitted up like Anne was, know that they have no power, no choice and I like that, I like that a lot.

Despite not really caring about James and Anne's story I have to admit I was intrigued how Anne would react to a real cock inside her. I guess from her coolish exterior she was happier taking it than risking that evidence being revealed but she would be getting a whole lot of cock over the next week so I would be getting a chance to find out exactly what her limits would be.

She was naked because I had ordered her to strip all her clothes and reluctantly she had complied, neatly folding her clothes on the hotel room bed and standing, looking embarrassed as hell as I openly stared at every inch of her cute white body. It would contrast nicely with my shiny, jet black skin.

I made her wait. Standing in front of her once I had guided her to her knees before me. I played with my cock slowly, letting her watch every inch of my nine-inch penis as the head pushed at my foreskin and a slight sheen of pre-cum emerged to make my helmet even shinier. I ran my fingers up each side of my shaft, feeling every vein stretching against it until I reached my balls and gave them a little squeeze to make sure I was fully aroused – no problem there.

"Open up Anne, let's see how good a cock sucker you are."

I quickly discovered she wasn't very good. I guess her husband hadn't been making it up after all, she sucked (pardon the pun). Then again maybe it was because she wasn't exactly enjoying this. Whatever the case no way was she getting away with just lapping at my member like it was some kind of disgustingly flavoured lollipop.

"I guess you're shit Anne, so how about I show you how to be a good cock sucker."

She had had her chance and blown it (again, no pun intended) so I reached down, cupped my hand around the back of her head and pulled her mouth right onto my cock until the tip touched the back of her throat. I could feel her pushing to get it out but I held it there for a second or so before relenting and settling into my own rhythm for face fucking her and while I didn't go quite that deep again she got the message and took a good five or six inches in for the next few minutes as my cock got wetter and harder and her mouth got more used to having my big, black cock inside it.

This was better, even if I was doing all the work myself, she reached up to try and use her hand to guide my cock but I wasn't having none of that and slapped her hand away and told her she'd had her chance, it was my way now. All I had to do was stand here and fuck her mouth and ponder exactly where I should shoot my load. Her hair? Her mouth? How about her eyes? Or nose? Decisions, decisions, it can be a hard life sometimes.

I'm particularly good at maintaining an erection so Anne's out of practice mouth was going to be getting quite the workout. I decided to let her lie down, see if that helped her. I popped my cock from her lips, enjoying her look of distaste as slimy trails came from the tip all the way to her lips before breaking and falling against her chest, let her have a brief moment of hope that this was as far as I wanted to go with her today then shattered it by ordering her up onto the bed. I made her lie across the length of the bed and carefully positioned her head so that it was actually off the side. I supported it in my big hands and even then I don't think she figured out what I was going to do. I stepped up so my thighs were either side of her head and gently eased her forehead back and her mouth open and then plunged my messy cock back inside her. She hadn't expected that and wasn't quite ready for this position that allowed me to get my dick even further down her throat. My balls too got to play a part, resting as they were on her nose and sliding down either side to press against her eyes as I continued to press further. After a while of that I removed my cock from her gasping mouth and chuckled at the trails of saliva that spilled from her upside down mouth to fall against her own cheeks and forehead.

With my slippery cock still out of her mouth I inched forward so that my ball sack hung over her lips and I squeezed it into her mouth now, wanting Anne to taste what a black man's sweaty balls tasted like while her nose was now dangerously close to being buried in my ass. I let her suckle on my balls for long enough before going back to fucking her mouth and by now I was at the point of cumming. I let her lips push my foreskin right back and after a few thrusts like that I could hold off no longer and exploded with multiple ejaculations into her mouth and onto her tongue. Anne tried not to swallow it but in that position all that happened was that my thick, white cum spilled from her mouth and dripped down her face, up her nose and all over her eyes and forehead mixing with her own saliva, her face truly was a sight to see by the time I stepped away from her.

I left her laying there gasping and got dressed quickly and she saw still in that position when I made to leave and left her with instructions for the next day.

"I'll pick you up from your office at one for lunch, you better be ready!"

*

Anne's offices were exactly as James had described them to me, inside a new looking building that was wall to wall windows and concrete. I had thought about showing up in real shit kicker clothes, ripped jeans and a white T-shirt maybe, but figured I'd maybe save humiliating her at her work until later in the week so I was a lot smarter than usual when I entered the building, dressed as I was in my expensive navy Armani suit. The cute receptionist certainly got a shock when I strode up to her desk and loomed over her (getting a none too subtle glance down her pristine white blouse at some nice cleavage) and asked to see Anne and that she would be expecting me. I guess I am quite an intimidating guy, six foot five tall, built like a football player and really dark skinned – I certainly stand out in a crowd. Her surprise seemed to be doubled when Anne buzzed down that I was to be shown up to her office immediately and that she was not to be disturbed until further notice. I flashed a self important smile at the receptionist and followed her up the nearby staircase, watching her tight ass wiggle al the way to Anne's office.

Anne waited until the receptionist was well clear of her office before closing and locking the door behind. It was a closed off office in a wider open plan one and the front and side of the office had large glass panelling that looked out onto the main office.

"I think you'd better shut those blinds, I doubt you'll want everybody to see what you are about to do" I stated pretty bluntly.

She locked eyes with me for a moment, the hard nosed business woman in her coming out, but I stared her down and she quickly realised that she wasn't making the decisions here, I was. She got up and deftly pulled the draw strings on the blinds and blocked us out from any prying eyes.

"Look, whoever's doing this (I assume someone's set you up to do this?), I can pay more than them if you stop. Tell me."

I smiled my shit eating smile at her and shook my head, I wouldn't even tell her a deal was a deal, I didn't even want her to know that there was a deal. Instead I reached into the satchel I had carried up with me and put an object on her metal/glass table as she slumped back into her chair across from me.

"No Anne, what you see on your desk is a top of the range Black Mambo vibrator. Bought this very morning from Dirty Harry's sex shop on 42nd Street. What I want you to do this lunchtime is to break it in, give it it's first use, understand? You're going to get off with it right here and right now, better get going."

She looked at me like I was crazy for a moment, like it was the craziest suggestion she had ever heard. But I guess she remembered the hotel room the day before and realised I was deadly serious. But she still didn't make a move, instead she scrutinised the obscene sex toy parked on her work surface. I knew it wasn't the first the bitch had seen, that was for sure.

*

At first we played with each other and she would let me go down on her. (She doesn't like to give blow jobs and has never broached the subject of anal sex.) Then she asked me to buy her a dildo and I got her a hefty black circumcised cock and over time, after fingering her pussy for a while to get it wet, she would ask for "her friend" and I would fuck her with the dildo. Sometimes while I was playing with her pussy, she would grab my cock and say, "No, not good enough. Get my friend." Then I got her a vibrator egg to use on her clit and that worked really well sending her through the roof! All during that time, after she would cum, she let me jerk off. She got so into the dildo that once (and ONLY once) I thought I'd like to fuck her and got on top and had my cock pressing against her pussy lips when she shouted hoarsely at me, "NO! Get me a REAL cock." And I rushed to get her dildo and she took that in. After years of fucking the black dildo, it was wearing down and she told me to get a new one that vibrates so now she has a slimmer and longer one of smooth, shiny, pink, plastic.

*

It had taken her ten minutes to realise I was deadly serious and to get the vibrator in her hands and pull off her panties and hike up her skirt, all the time I sat in the chair opposite and contemplated her with undisguised amusement. She had licked the tip of the plastic phallus and was easing it into her vagina when I decided to make things a little more interesting.

"You know Anne, I'm a busy man, I don't have all day today so how about this? You have until one pm to get yourself off with that thing. If you don't then I am going to open those blinds and if that dildo comes away from your pussy for any length of time other than if you have cum then I'm going to assume you just want me to hand over my evidence. It's 12.35 right now, better get a move on."

Man you should have seen the look that bitch gave me at that, pure anger, she obviously was not used to not being charge and was not liking it at all. Which, I have to admit was turning me on, seeing a powerful woman like that reduced to fucking herself with a moulded lump of plastic for my amusement.

*

Now, it is true that if I try to initiate sex, it is completely unsuccessful if she isn't interested; however, when she wants it there is no denying her. Over time, what I have found is that I can get horny as hell and if she wants sex, I do what she needs with her dildo and egg. Instead of sometimes touching myself (which distracts from what I am doing for her) she has me concentrate completely on her and I "tune in" to her reactions and rising need until she cums and when she does, I feel such a strong surge of emotion that, although I do NOT cum, I get relief from HER cumming. It is incredible!

I'll detail how she fucks her plastic. When she wants it, she just tells me, "Come to bed. I want you tonight."

We undress and I take a bag from the dresser containing her dildo and egg and put it next to me. She needs very little foreplay, none of it with her tits (but she has nice tits). We French kiss and she spreads her legs and I begin to rub her pussy. I play with her clit, sometimes rubbing it, sometimes stroking it like a small cock, until she begins to get wet. I finger fuck her a little, bringing her cunt juices to her clit to make it slippery and I rub it and jerk it off some more. I wish she would tell me to go down on it, but she hasn't had me do that in years. When she is well lubricated, she says something like, "Get the egg" and I know she wants it on her clit. I turn it on, not too high, and begin to rub it along her cunt lips and press it to her clit. I feel her hips pressing up to increase the feeling. After a few minutes of that, she will say, "I want my friend." and I get the dildo and turn it on to low. At first I rub it along her pussy making it wet and then s-l-o-w-l-y press the top into her. When it is in, I turn it up to half speed and begin to fuck her with it. I also press the egg to her clit and hold it there with my other hand. She will begin to hump the dildo, fucking it slowly at first but increasing her thrusts. As she does, she tells me, "fuck me...fuck me" and I turn up the speed on both to full blast. By then, my fingers are not touching her at all. It is all plastic that she is fucking. As she humps faster, I say things like, "Yeeeessssssssss ...fuck it...it is so strong and hard...fuck it good." And she begins to moan and lets me know, "I'm cumming" and I feel it too and tell her to "cum for us...cum for both of us." And god, she moans out a long sound with her release and I feel it too. It takes a few moments for her to come back down to earth and presses both her dildo and egg away. I always take the dildo a suck her plastic lover clean before putting it down. Then the both of us settle down, happy and satisfied, until the next time she wants it."