To Take Advantage Of A FriendbyMikeWrites©
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?"
"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."
"Navy blue panties."
"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."
"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?"
"But you're going to let me fuck you there?"
"I…I suppose so."
"I'm going to fuck your asshole?"
"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?"