Cute Girls

To Take Advantage Of A Friend

I would never have thought it. I had known Jane eight years, and although she was cute-pretty - five nine, blonde, with a narrow boyish figure - we had never moved beyond low key flirting. Truth be told, despite her niceish looks she wasn’t that sexy. Too cold. So the possibility that, for a week, she would submit herself to my every whim and fancy, well it wasn’t even fantasy, because I had never considered the details of fucking her.

Then she screwed me over big time, a monstrous piece of selfish shitty behavior, that cost me money and even risked my career. A groveling e-mail followed, but my fury and disappointment led me to simply ignore it. For several months silence, then this e-mail:

“I miss our friendship. I’m so sorry for what I did. I would do anything to put it right. Please reply. Jane.”

I deleted the mail, my anger still burning too brightly. But a little later in the day I remembered Jane bending across a table and the way her jeans had pulled a little into her ass crack. A boyish figure, yes, but not a bad ass.

And she’d just said she’d do anything.

I felt a rush, a burst of excitement. My whole body tingled with just the possibility. Anything? I couldn’t, could I?

I checked frantically for her deleted mail, and thank heavens it was still lurking in the system. If nothing else happened, it could still form the basis of many a happy fantasy.

“Anything?” I clicked Send. I felt so powerful, because I didn’t care. If she reacted the way I expected, then I could go back to how I’d been before, with Jane receding into that part of my memory devoted to former friends.

And yet it was all to evident I really did care. The next hour and a half was a high tension waste of time, as I waited for her reply. We were both at work, she was usually in her office, so there was no reason for a delay. Each ping of a new mail caused my cock to stir, only to be disappointed when I found out it was not Jane.

Then “Sender: Jane Re: I’m Sorry”. Her message was brief, and something of an anticlimax. “What do you mean?”

I wondered briefly what to say, but the momentum of my excitement wouldn’t let me think too long about my reply.

“I mean will you do ANYTHING to put things right?” I clicked Send, the awkward throb of my cock pulsing in my suit pants telling me this was one of the most exciting games I’d ever played.

Jane’s reply was almost immediate. “I’m sorry Mike, I’m not really sure what you mean but yes I do want to be your friend, and if you tell me what I have to do to make up to you then I’ll try to do it.”

I still wasn’t sure that Jane totally understood exactly what I was implying. It was time to make the final pitch.

“If you want us to be friends, Jane, you have to agree to do ANYTHING I want for the next week. ANYTHING. If you don’t agree, then this e-mail is the last thing that you will ever hear from me. If you do agree but then refuse to do something that I ask, then you will never hear from me again. But if you do anything I want for a week we will be friends.” Given some of the ideas I already had in mind this last sentence seemed a little inaccurate, but that didn’t matter for now.

There was a longer pause now, which was agonizing. I felt as if I was so close to the most extraordinary thing, but I knew that surely Jane must say No.

Then: “I’m really not trying to be difficult, Mike, and I so want us to be friends again, but I do want to know what I’m getting myself into! Can you please give me an example of what you mean by ANYTHING?!?”

Surely she didn’t think I was expecting her to cook cordon bleu meals for me every evening? Or to rob a bank?

By now the pressure of my cock was almost unbearable. Being at my desk in my office (at least I had my own room, as did Jane), made my discomfort even sweeter.

I took a deep breath. This really was it. “Okay. At the very tamest end of what I mean by ANYTHING, tell me what color panties you’re wearing.”

The reply was swift. “I see. Navy.”

“When did you last make yourself come?”

“Sunday morning.”

“Have you ever had a cock in your ass?”

“No. Is that what you want to do to me?”

I looked at my watch. Four thirty. I couldn’t possible leave for another hour. How beautiful and agonizing that would be. “You’ll see. I’ll be at your apartment by six.”

++

I got to Jane’s apartment block early. Partly it was sheer excitement and need - that first day I was in a daze. But I also wanted to catch her off guard, to stop her having any time to prepare herself or to divert me from anything I might want.

Jane was dressed casually - a career in the media - and walking quickly as she made her way to the entrance to the block. Jeans, a pale cream sweater, all setting off her tall skinny figure well. She was so absorbed in her thoughts - now what were they I wonder - that she was almost on me before she saw me.

“Hi.” I decided not to smile. It wasn’t appropriate for our new relationship.

“Hi.” Before we’d kissed when we met, but this was very definitely not before any more. Her uncertainty was both exciting and slightly scary. Having got her here I didn’t want her walking out.

We didn’t kiss. “Shall we go up?” Her tone was brusque but I guessed that was nerves.

Up in her apartment she poured us both a glass of an expensive little Chablis. I sat on a chair, studiedly alone, and she was on the couch, sipping nervously.

“Listen, Mike, I really am sorry about…”

I cut in quickly. “Forget it. We’re resolving things a different way. But I will say I really hope this next week works out okay.”

“Yes. So do I.” Now that she was there, in the flesh, my friend Jane, it was so difficult to start. I’d sat here so many times, talking about anything, could I really start issuing sexual orders? I was so close to blowing it, to giving up, when I found a way to get started.

“So, navy panties.” Jane nodded. “Do you ever wear other colors?” Another nod. “What colors?”

“White. Gray. Sometimes red. I don’t really think about it.”

“Do you ever wear thongs?” I was easing us into intimacy.

“Sometimes. Usually if I’m wearing a skirt.”

“But you’re wearing panties now.”

“Yes.”

“Navy blue panties.”

“Yes.”

“Show me your navy blue panties Jane.”

She put down her wine glass and stood up. Was she walking out? “Do you want me to take my jeans off?”

“No. Just pull them down so I can see your panties.”

Jane fiddled with the metal stud, her hands shaking, then the zipper was sliding down and a vee of blue material was visible before she pulled the rest of the jeans down to her thighs.

“Come here.” She walked awkwardly with her jeans like that, but then she was standing so close. “Show me your titties.” It was a conscious decision to be coarse - I wanted the brutality of our respective positions to be explicit.

Jane raised her eyes a little - what had she got herself into? - but then she reached to the bottom hem of her sweater and lifted it up and over, tugging up her bra as she went.

I had always thought that Jane was a little “light” up top, and sure enough her poor little breasts didn’t stand out too much, but what she lacked there she made up for in the length of her nipples. They must have been an inch long, chewy brown pencils just aching to be bitten and tugged. It was also the first sign she was turned on by what we were doing or, rather, what she was doing for me.

“Your nipples are stiff Jane.”

“Yes.”

“Are you turned on?” She shrugged. I could feel a little battle of wills coming on, and I was determined to win it. “Are you turned on, Jane? I want to know. I want you to tell me.”

“I guess. Maybe a little.”

But her feeble little act of resistance had worked against her, spurring me on to more.

“Is your cunt wet?” Again Jane raised her eyebrows. I knew she didn’t like the C-word, even in a social context, let alone when it was referring to her own genitals. “Answer me. I’m going to find out in a second anyway.”

“Yes. I guess. A little.”

“Show me your wet cunt, Jane.” Again the eyebrows raised, then Jane slipped her hand into the elastic waist of her much-discussed navy panties and pulled them down to join her jeans at the top of her thighs.

I was intrigued to see that Jane had a neat but full triangle of mid-brown hair, a clear but pleasing contrast to her straw blonde head hair.

“Show me your wet cunt properly, Jane.” She paused, wondering how to comply, then thrust her hips forward, bringing her pussy even closer to my face.

I could now see clearly that Jane’s labia were swollen and puffy with her excitement. “Your cunt is soaking Jane. Tell me your cunt is soaking.”

“I’m soaking Mike.”

“Tell me properly. Tell me your cunt is soaking.”

“I… Mike, please, you know how I hate that word.” How weird, that she could expose her naked body to me but she balked at saying something.

“Tell me your cunt is soaking.”

“I…my c-c-cunt is soaking.”

“Good. Now show me your ass.”

Jane turned slowly around. From what she’d replied in her mail and from what I knew of her personality anyway, I guessed she’d always been more of a front end girl. Well that was about to change.

Jane had a lovely rounded bum, a slightly surprising contrast to her flat chest. “Pull your ass cheeks apart for me. I want to see your asshole.”

She reached around, maybe a little shocked at the level of intimacy I expected, and separated her cheeks a little.

“More.” She pulled again and her tight little anus winked at me. Her virgin anus. I reached out and gently pressed a fingertip against it. Jane jumped a mile - it was, after all, our first physical contact. I gently stroked her grimy little hole. “So you’ve never been fucked up there?” She shook her head. “Never had anything up there?”

“No.”

“But you’re going to let me fuck you there?”

“I…I suppose so.”

“I’m going to fuck your asshole?”

“Yes.”

“Say it.”

“You’re going to fuck my asshole.”

“Good. Now kneel between my legs. Facing me. That’s good. Now pull out my cock.” Even the touch of Jane’s hands on my zipper was nearly enough to send me over the edge - it had been a long few hours. And it was the most exquisite release as she sprung me free just inches from her nervous face. “Okay Jane, for our first time you’re going to bring me off over your face. Later on I’m going to fuck you in each of your holes, but for now we’re taking it simple.”

Jane reached up, without even being asked, and began stroking her fingers around the shaft of my cock. Her grip was a little hesitant at first, but that almost increased the delicacy. “Tell me what we’re going to do later Jane.”

“You’re going to fuck each of my holes.”

“Tell me about what I’m going to do to your virgin ass Jane.”

“You’re going to fuck it.”

“Say everything properly, Jane.”

“You’re going to fuck my virgin ass.”

“Am I going to come inside your tight virgin asshole Jane?”

“If you want to.”

“Then say it.”

“You can come inside my tight virgin asshole if you want to, Mike.” The look on Jane’s face was positively coquettish as she said this, and it was all too much as I boiled over, shooting thick white gobbets of sperm onto her face, Jane still stroking carefully and slowly, obediently keeping her face in position as I shot my come all over her.

I flopped back, briefly totally spent. But the sight of Jane - my friend Jane - still kneeling dutifully between my legs, her face spattered with my come and her nipples poking out even more stiffly, started an almost immediate reaction in my cock. I looked at my watch. “Six days, twenty three hours and thirty minutes to go.” Would you believe it, she almost smiled?

++

In fact I didn’t take Jane’s anal cherry that evening. It seemed far more piquant to allow her to anticipate it for a while, and so I told her that she would be ass-fucked the following evening.

All through that next day I sent her e-mails, reminding her what was going to happen, forcing her to describe in ever more detail and using ever filthier words to tell me what would be done that evening. It was tempting to get her to start doing things to herself while at work, but reminded myself that drawing things out would be more fun.

Once again I beat Jane to her apartment, and although once again she was walking quickly as she walked around the corner, I thought this time maybe the motivation was excitement, not fear.

For just a few minutes upstairs the same “being face-to-face” awkwardness surfaced, but then Jane fetched us some Chablis and we seemed to fit back into the previous night’s roles.

I told her to strip, kneel on all fours on the bed, and pull her ass cheeks apart for me. I spent a little time pointedly and carefully inspecting her ass, knowing that such an intimate exposure would be embarrassing and maybe exciting for her.

Maybe for some people in my position and with my control over Jane the obvious thing would have been to simple fuck her ass straight away, driving hard into her tender hole regardless. But I was far more interested in cold hard Jane discovering that she loved to be ass-fucked, just like she’d found - so I believed - that she got turned on being subjugated to my will. Far more exciting for me to see coming and coming from the sordid pleasures of ass-fucking than the simple buzz of her face contorted with pain. And the pain would happen anyway, I knew that.

I told Jane to ask me to lick her asshole. Starting cold, so as to speak, she struggled to begin with but soon managed the request. She actually gasped as she felt my tongue press against her hole, and quickly she was pushing herself back against me, loving the firm wet sensation as I probed her sphincter.

“Feels good, huh?” I asked, momentarily pulling away, and her nodded response persuaded me to try a little diversion from the main task at hand. “Lick my asshole then Jane.” She rolled over onto her side, looking at me warily. She hadn’t expected that.

I lay back on the bed, lifting my knees up to my chest, exposing my asshole to her. She looked away. As I’d figured, doing my asshole was a whole different proposition.

“Come over here slut.” It was the first time I’d used an abusive term, and Jane flinched. I could see she was calculating whether to give up on the whole deal. Slowly, reluctantly, she crawled across the bed. When she was close enough I grabbed her hair, and she flinched more than before, expecting a strike. But instead I coaxed gently, drawing her face ever closer to my ass. The look on her face was so repelled by what I wanted that I could almost hear her whimpering. As she got close to my ass she began to resist, holding herself away. But my grip was firm and impassive and she found herself just inches from my bare ass. Her eyes were closed.

“Open your eyes, slut.” Nothing. “Open your eyes and look at my asshole.” I gave a gentle tug on her hair and her eyes opened. “Look at it.” Her gaze turned. There, it wasn’t so bad. “Okay now lick it.” I drew her in, she wasn’t so much resisting now, then at first Jane was kissing my anus with her lips and then as I held her tightly in position I felt her tongue poking against it too. “Good little asslicker,” I murmured, “now open your eyes and look at me,” and then our gazes met as my friend Jane tongued my asshole for me.

++

Because I wanted to see Jane’s face as I penetrated her asshole for the first time, I told her to lie on her back. She seemed confused, maybe relieved, as if this meant she wasn’t going to experience the unavoidable agony of being assfucked.

I told her to put her knees up and realization dawned. To prepare her properly, I rubbed around her anus with my fingers, slicking up my fingers with her juices (yes she was soaking). I pressed a fingertip against her asshole and she tensed, sensing what would follow, and I moved my mouth to her clit to lick and relax her. As my finger slid into Jane’s asshole I could hear her breath in, but I was confident that the combination of a finger in her ass and my tongue on her pussy would quickly be delicious. Sure enough she soon relaxed, and I could hear her moan each time I poked my pinky up her butt.

The sensation for me, too, was exquisite, Jane’s anal canal so tight and hot around my finger. Once she was comfortably into me finger fucking her ass I repeated the same slow delicate procedure with two fingers. This time her tension took much longer to subside a little, and I could feel that she was struggling to cope with such an alien presence in her bottom. But as I continued to lick her clit while my fingers poked in and out I could sense that she was beginning to understand how delicious her discomfort could be.

As I slid my fingers out the look on Jane’s face turned to true apprehension, sensing that the time had come for the preparations to end. I experienced a strange mixture of emotions, the part of me that remembered my friend Jane concerned and tender, but another, far greater emotion was pleasure that I was about to do this to her poor innocent behind.

I slicked my cock in Jane’s cunt juices then rested it right up against the entrance to her most private hole. Her eyes were wide open now, looking directly at me, wanting somehow to connect with me as we shared what was about to be done to her. As I began to press into her asshole Jane’s eyes opened wider, as nothing that my fingers had done had prepared her for the monstrosity of what was entering her bottom.

I moved quickly, knowing that that first penetration is the worst part, but relishing the extraordinary sensation of the walls of Jane’s tight sphincter gripping my cock. I began to slide slowly in and out, Jane’s mouth making a permanent “aaah” shape, her eyes never leaving mine. I lent down to chew on those extraordinary nipples, providing Jane with an entirely new set of sensations. I reached to stroke her clit, which I found was throbbing away at this multiple assault.

Still chewing Jane’s nipples, I began to urge Jane on. “Come for me slut. Come for me with my cock in your asshole. I want you to have an assfucking orgasm. Come on my cock, slut.” Looking up I could see that Jane was in an amazing place, overwhelmed by the intensity of her first experience of anal sex. Then she was bucking and thrusting, her face contorted with the pain and pleasure of her violation. That was enough for me, and I released too, shuddering at each explosion, releasing my sperm deep into Jane’s bottom. Our eyes were locked, and I knew from her expression that I had just taken Jane to a dark and wonderful place.

++

Although the physical and mental sensations of assfucking Jane were exquisite, the nature of our relationship and the time limit on it encouraged me to be ever more adventurous with her tasks.

The next incident worth recording was inspired by some idle chat while we had been eating. Jane mentioned that her sister Anne had got into a new job. I had only met Anne once, about a year back, and she had struck me then as almost the other side of the coin to her sister- laid back, sexy, always fun. Oh, and nineteen years old.

Later that same evening, Jane was tied to her bedposts, a slim vibrator buzzing away in her asshole and clamps on her nipples. I had been teasing her for over an hour already, and her skinny body was sheened with sweat. I knew that she was turned on enough for anything. Anything? Well we would see.

“I bet Anne’s a hot fuck,” I whispered softly, my fingers making lazy patterns around Jane’s cute pubic thatch. I could feel her tense at the unexpected turn the conversation had taken. “Quite a body too.” Where Jane was skinny and boyish, Anne was all voluptuous curves. “Wouldn’t you love to see Anne on all fours, Jane, those beautiful titties hanging down as I fucked her from behind.” I brushed Jane’s clit. Still slick and throbbing. “Maybe I’d titty-fuck her for a bit, she could do that, couldn’t she, with her beautiful titties?” There was no reply. “Couldn’t she, Jane?”

“So you fuck your husband in the ass with it?” Sheila questioned still amazed by the whole idea of the device. “Have you ever fucked a woman in the ass with it?”

“Yes my husband really enjoys a good screwing in the ass once in a while. And yes, although anal is sort of taboo I have found many women do have the most intense orgasms when I fuck them that way,” The mentor explained smiling at Sheila.

Mandy was totally turned on by the thought of fucking James in the ass. She held up the device and looked at it. She looked at all the toys in the room set up for display and then pointed to the horse cock Sheila was holding and asked, “So a woman could fuck a man in the ass with something like this?”

“This is perhaps larger than most men would enjoy, unless… well never mind,” the mentor stopped short.

“What? What were you going to say?” quizzed Mandy.

The mentor continued, “Well unless they have had experience being fucked in the ass. This particular toy takes a little work to get in, but it has the right shape and flexibility to reach the prostate and rub things the right way deep inside the male rectum,” She continued to inform Mandy.

A knock at the door cut the conversation short. Mandy opened the door. “Hello come inside. We are still getting things set up. Take a seat it will only be a few minutes before the other guests arrive,” Mandy said as she motioned for the woman to sit. She was one of the gals from the gym. The woman blushed a little at the sight of all the toys.

“Sorry, we usually start with the items covered up. You are getting a chance to see them all at once like this,” Mandy apologized. I had better go get the model ready now,” Mandy said as she slipped into the bedroom.

James was drying off with a towel. “Hurry honey, the women are starting to show up. Oh, and I need to oil up your muscles here stand up with your arms and legs out,” Mandy said in a rushed tone.

“Hey this thing isn’t going to get out of hand is it? I mean you wont let these gals pinch my ass or anything will you?” James quizingly asked.

Mandy began rubbing oil up each leg and then ran her hand between his gorgeous ass cheeks right up to his puckered anus.

“Well if you do feel anything it will be me. So just go with it. Remember tonight is all about sales and we will have your tush to thank for it. Quick put the chaps on!” Mandy said as she continued to rub oil on his back and shoulders.

Mandy walked him through the living room. James looked at the woman from the gym and stopped short. “Gina what are you doing here?!” James questioned somewhat confused.

“Fancy seeing you here James. And from the looks of it we will be seeing you all night. Nothing I haven’t seen before,” Gina said in a condescending voice as if to admit she was upset at James for taking advantage of her.

Mandy pulled James around the chairs to the opening. “Here lean your elbows on the counter while I go around to the kitchen,” Mandy instructed.

She went into the kitchen and placed the wooden pillory under his neck. “Here put your wrists up here,” she instructed in a sweet unaffected somewhat sexual way. She placed the top piece over his neck to complete the pillory. Then she closed the hasp to hold everything in place. James was now totally isolated from the living room with the pillory closing off the opening between the two rooms entirely.

“Here honey, here is the remote control. Remember to stand like a stud with your cute butt perched out for us to admire. If you need me just raise your foot and shake it a little I promise to come right away,” Mandy instructed as she looked at James’s somewhat embarrassed face against the dark wood.

“Mandy that gal Gina, she means nothing to me. Really, she just has the hots for me or something,” James tried to smooth over the uncomfortable encounter.

“James, I have invited all the women from the gym. I don’t know if they will all be coming or not. Don’t worry though they probably wont recognize you… well unless they have seen you naked,” Mandy snided obviously upset.

“Oh here, now that you are all secure and tidy lets do one more thing to help you enjoy the night all that much more,” Mandy said as she picked up a small tangerine and shoved it into James’s mouth.

She took a dishtowel and rolled it up lengthwise and tied the tangerine firmly in place. She took the remote from his hand and pressed the scan button and placed it just beyond his reach. The channel would change automatically every 15 seconds… all night long.

James had a look of panic as she walked slowly away from him towards the kitchen door. She winked at him and blew a kiss, staring at him intensely while she slowly closed the kitchen door.

James knew he had made a huge mistake. This was not going to end well for him. He went trough the list of women he had nailed at the gym. His mind was spinning.

When Mandy rounded the corner to the living room both her mentor and the other women were found staring at James’s butt. Mandy looked over at him. It was amazing seeing his naked well oiled buns protruding out of the chaps. He looked amazing in that position.

There he stood nearly nude with his skin all shiny from the oil. His muscles had nice shapes. His muscular legs stood two feet or so away from the wall and his torso bent forward so his neck would line up with the hole in the dark wood pillory. They could hear the channels changing on the TV.

“See that proves he is all man isn’t he? Even standing nearly naked in a pillory he can’t watch one channel for more than 15 seconds,” Mandy joked winking at Gina. They all laughed. Mandy and her mentor carefully placed a linen cloth over the toy displays.

Other women began to arrive. Slowly the room filled. Each woman gasped at the sight of this male slave on display. Without fail their chins would drop and no noise would come out as if to say, “oh my… what a hunk!”

Somehow, without the annoying cocky face, James took on a Greek God dimension. His body by itself was a delectable treat. The black leather chaps accentuated his perfect ass.

And the pillory added the illusion of unbridled anonymous access to this near perfect well oiled male body only a few feet away from the chairs.

Dare say, had any of the women been left alone by themselves in the room each would have not been able to resist at least giving that rump a gentle pat or something.

Mandy nervously started the meeting, “Ladies thank you for coming to my party. As you can see we have afforded only the best of luxuries as we discuss this taboo topic of sexuality.”

She pointed to James in all his glory as she continued, “I can assure you the model can not hear a word of our secret conversations, as he is busy watching TV.” All the women chuckled.

“Here are clipboards with a pen. Each clipboard has a list with a checkbox next to each description. As I show each toy and describe it’s use please check the box if you would like to order one, ” Mandy instructed

One by one, Mandy pulled each toy out from under the linen and carefully described the use. There were every shape and size imaginable. Everything from a short slender butt plug to the enormous life like black horse cock Sheila had looked at.

It was fifteen inches long and three inches in girth with a head the size of a man’s tightly clinched fist. The women were squirming in their seats and the actual odor of sexuality filled the room. Then Mandy’s mentor took over.

“Now ladies we have a more intense group of toys which are not for the feint of heart. Is everyone up for it?” She asked.

The women all looked around at each other and nodded. The Mentor slowly pulled out the thick black leather panties with the hard plastic base. She handed them to Mandy. “Here Mandy put these on so we can show the ladies,” the mentor said in an insistent but pleasant tone.

Mandy blushed and slipped into the bedroom. Her mind was spinning. She wondered if her mentor was hinting at actually fucking James in front of this group of sexually aroused women?

He certainly deserved it. She quickly pulled off her skirt and panties, stepped into the device and pulled it up. It felt secure and fit perfectly.

Mandy came back into the room The women gasped. Mandy walked over to her mentor not sure what to do next. “Remove your blouse but keep your bra on,” the mentor instructed Mandy. Slowly Mandy unbuttoned her blouse. It had a sort of strip tease effect on the women.

Her mentor picked up a slender smooth bright pink toy about an inch in diameter and about seven inches long. She fastened the toy to the base and then pulled on it moving Mandy forward a few steps.

She winked at Mandy and gave the dildo a few hard tugs. “See ladies, the dildo is firmly attached and locked in position, ” the mentor explained.

Mandy felt the bumps inside the panties rub her clitoris when the mentor tugged on the dildo. It made her pussy damp. She knew the mentor had done this to get her going.

The mentor stood up and walked over to James. “This is the night when the tables are turned, who would like to see Mandy slide this pink dildo into the model’s ass?” she asked.

All the women raised their hands. The mentor looked into Mandy’s eyes. Mandy smiled a very naughty smile.

“Gather closely around Ladies,” The mentor instructed. The women all left their chairs and sat on the floor in a semi circle around James, who was quite unaware of what was about to happen next.

The mentor removed a jar of lube from her bag and smeared some onto the pink dildo, deliberately moving the dildo up and down pretending to be concerned that the lube cover the entire dildo.

This drove the little bumps inside the panties up and down Mandy’s clitoris. Mandy blushed as the mentor looked at her and winked.

The mentor kneeled behind James. She slowly stroked the insides of James’s thighs. She bent over and kissed his ass cheek. James twitched a little but stood calmly.

The mentor swiftly ran her lubricated middle finger between James’s ass cheeks right up to his anus. Surprisingly he remained still, very still.

Mandy knew how confused James must be. But she did nothing to stop what was going on.

Pulling one ass cheek to the side the mentor quickly shoved her finger rudely up into James’s ass. A quiet moan could be heard from the kitchen over the noise of the TV.

The mentor rubbed James’s ass with her free hand and began to fuck her finger forcefully in and out of his anus. “They call this foreplay,” the mentor said jokingly. All the women chuckled.

Mandy wondered what James was experiencing. She waited to see his foot raise and wiggle but it did not. Instead his ass actually began to thrust back to take more of the mentor’s finger.

A bulge began to grow in the front of the chaps. The mentor motioned for another woman to remove the chaps. Mandy nodded.

James spread his legs apart as he felt the chaps come off. His penis bobbed up and down as the mentor’s finger dug rudely twisting and turning in and out of his anus.

A woman stood and asked if she could suck the model’s penis. Mandy was not sure what to do. The mentor pulled her half bent finger out abruptly and swatted James’s ass hard making James jerk out of surprise. “Ladies, lets not go crazy. The night is young,” said the mentor.

The mentor looked at Mandy as she explained, “There is a whole room full of toys here. If it is alright with Mandy, any woman who would like to purchase a strap on panty and one of the toys may fuck the model.”

The women gasped in excitement. Gina got an evil look on her face. So did several others.

Mandy blushed a little. She could see that James was enjoying the finger in his ass. “Yes that would be fine. Any woman who purchases a strap on panty and toy is welcome to fuck the model,” Mandy said not believing she was actually saying it!

“Each woman in line will begin by sucking the model’s penis, then taking a position to fuck his ass while the next in line sucks his penis and so on.

Mandy will begin the process. That way each woman will have the chance to suck the model and then to fuck the model. Sort of a love then hate relationship.” The mentor joked.

The mentor looked towards Mandy. Mandy thought of the money they would earn. She remembered telling James tonight was about selling.

Plus she knew the relationship was close to ending, and she was still furious about the obvious lack of fidelity James had clearly demonstrated. She nodded her head yes with a very naughty demeanor.

The women giggled with delight each grabbing a strap on panty and toy and forming a line behind James.

“Women, lets have you change the order of the line by the size of your toy, smallest toy first largest toy last. We don’t want to hurt the model,” the mentor instructed.

“Well at least not much at first,” she whispered in a dominatrix sexual voice to herself while running her hand down James’s back side down between his ass cheeks to his balls where she cupped her hand and gave an authoritative squeeze.

Meanwhile on the other side of the wall isolated from all the discussion James’s mind was reeling. His anus was quivering from the finger fucking he assumed Mandy had given him.

He imagined it was her that was cupping and firmly squeezing his balls. He felt he deserved a little humiliation after what took place with Gina earlier in the evening.

He wondered who else was in the room now. How many of the women he had screwed at the gym were sitting there steaming mad realizing it was Mandy that was living with him.

Then he realized all the boxes of sex toys which were also there. Surely Mandy would not allow anything to get out of hand. He felt ill in the pit of his stomach.

He decided to let Mandy have her fun getting even with him. He assumed she would be sticking a butt plug up his ass and maybe a few other odd toys, just to reinforce to the other gals that he belonged to her. He decided he could handle that.

“Ok dear lets get ready for the initial loss of anal virginity. Go ahead and suck the loverboy for a few minutes while I loosen him up a bit more. I will give you the signal when he is ready to have the toy up his ass,” her mentor instructed.

Mandy situated herself to suck James bobbing cock. She cupped her hand around James balls and slid her expert mouth down over the penis right to the hilt. She began sliding her mouth up and down slowly.

The mentor instructed the ladies, “Gather round ladies you need to see how to open a mans anus. They are a different animal. They like things to progress quickly and with vigor!”

The women stood up and gathered around James. “Start with one finger as you have seen. Then once it is lubed up go right on to the second finger. The first finger is just for lube,” the mentor instructed. “After two fingers will twist easily go right on to the third finger. Then check for a slight gape. I will demonstrate now,” the mentor said in an almost clinical tone.

The mentor stood behind James and squirted more lube onto her fingers. She roughly shoved two fingers up his corn hole. She twisted them rudely and shoved in deeper swatting his ass hard several times.

The mentor twisted violently from side to side as far as her wrist would let her. “This particular man is experienced at anal sex and seems able to dilate rather easily. He is a regular at taking it up the ass which is a good thing considering what we are about to give him,” she said as she patted his ass gingerly. “See how he bucks to take me deeper? Yes this man is no stranger to anal play he is quite enjoying this process.”

She continued to instruct giving tips as she violently and relentlessly shoved a third finger inside his ass eliciting an audible moan from the kitchen, and prompting James to perch his ass even higher. “If you will notice his ass perches up indicating he is enjoying what I am doing. If a man ever turns his hips in and clenches his cheeks together that means we need to slow things just a tiny bit. Or maybe not!” she said jokingly as she swatted his now reddening ass four or five times quickly.

The mentor grabbed one of James’s ass cheeks and pulled it to one side to expose his anus. Then she abruptly pulled the three fingers out with s slurp.

“There, see when the anus stays open for an instant or two then it is warmed up. It is not as delicate as a woman’s anus. You have to be forceful to get the man to really relax,” she said as she shoved the three glistening fingers right back in, twisted around, and pulled them right back out showing the slight gape yet again.

“Mandy dear, I think he is ready now, “she said tapping Mandy gently.

Mandy stood up from sucking his penis wiping her swollen lips. The next woman in line eagerly climbed down in front of James and guided his now throbbing cock into her mouth.

Mandy stood behind James and began rubbing the toy between his ass cheeks. The mentor pulled his anus open with her fingers to expose the slight gape. “Relax!” she commanded swatting him three times quite hard. His anus actually peeked open a tiny bit.

She gripped the toy and placed the tip on his anus. “Honestly, now that he is warmed up the best thing to do is just simply drive the toy home. No sense in being gingerly about it, fucking is dirty business, fuck the toy all the way in like you mean business,” the mentor instructed.

Mandy’s hands grasped his hips and in an instant she shoved the whole toy right up his ass. No mercy from a scorned woman.

James’s whole body tensed. Partly because of how deeply she pushed the long slender toy into his rectum and partly because he knew now for certain more than one person was working on him. His mind reeled at the possibilities of what might happen next.

Mandy fucked him hard. The small bumps in the panties rubbed against her clit with each thrust. She moaned as she fucked.

The mentor reached around Mandy from behind and placed her hands on Mandy’s breasts, pinching and rolling her nipples. Mandy came. She had a satisfying orgasm and then pulled the pink toy out of James’s raw anus which was gaping and convulsing.

“Wow, that really is a different kind of orgasm!” Mandy said in a weak but sexy voice. “I have never felt so powerful. Having a penis for a night is not such a bad thing.”

The woman who had been sucking James’s penis now stood up and positioned her slightly larger dildo at James’s slackened anus.

The next woman in line dropped down to suck his penis. The women were becoming exited to take their turn fucking the male model in the ass. They were all feeling their oats with their new found penises.

The mentor applied lube to the new larger dildo poised to violate James. Once the woman sucking began to get a rhythm going, the mentor pried James’s anus with her fingers and whispered to the woman, “remember simply drive the toy home. No sense in being gingerly about it, fucking is dirty business, fuck the toy all the way in like you mean business!”

With that the woman shoved the dildo right up James’s ass to the hilt. James instantly shot his load into the woman’s mouth who was sucking his penis.

She promptly swallowed moaning at the waves of semen which never seemed to stop, trying hard not to let any spill from the sides of her lips.

After James finished the woman pulled her mouth free and asked the mentor, “what should we do now, he’s finished?”

“Just keep sucking until it is your turn to fuck him. The sucking is really more for you than it is for him. Remember, he is the slave tonight. This is your turn to have pleasure. Don’t worry, he will still enjoy the sucking. He will have several orgasms before we are done dear,” the mentor explained.

Mandy stood watching the almost brutal fucking James was getting. She began to worry if he was going to be able to handle the line of women waiting their turn. Some of them had selected fairly large toys to attach to their special panties.

Tags: Fetish, Story