Lift Your Skirts, Emily

"Sir Joshua, I cannot comprehend how you could imagine that I actually want to submit to the humiliation and pain of - of buggery."

"But Emily, my dear, please trust me when I say that you will want to. Indeed, I suspect that, once you have experienced the delights of having your sweet, peach-like arse fucked and stretched by my very capable and prodigious prick, you will not only look back on the experience with a glow of pleasure, but you may find yourself returning to me so that we may repeat the experience. But first, despite your evident enjoyment of the fucking I've been giving you, we need to remove any annoying threat of pregnancy. So Emily, I think you are aware of the sequence of actions required. Please tell me what I should do. Do not omit any stages."

I sighed. Since my humiliation seemed to be without end, I resigned myself to getting it over with as soon as possible.

"Please, Sir Joshua. Please - please remove your prick from - from my cunt and, if you must, slide it as gently into as you can into - into - oh, into my arse. There, Sir Joshua -is that what you wanted me to say?"

"That, or something quite similar. Now, hold still my dear while I extract my cock from that delightfully-wet cunt of yours, and remove my fingers from your tight little arsehole."

I suddenly felt empty, his large penis and his insistent fingers having stretched and filled me beyond what I would normally have considered my reasonable limits. I braced myself for the inevitable - the insertion of that large, swollen organ into my tightest of holes, but instead he said to me "Turn around, my sweet."

I turned as he'd requested, to find that impressive penis only inches from my face.

"Suck me again, sweet Emily. I need to be as hard as can be if I'm to fuck your delectable little arse."

Although sucking a man's penis was not something I felt a lady should do, I complied without complaint. I knew now that it would be futile to protest, and I reasoned that if I were to excite him sufficiently, he might spend his seed in my mouth and spare me the sodomy that was to follow. But it was not to be. I dutifully took as much as I could of his manhood into my mouth, tasting what I assumed were my own emanations on him, and sucked and licked until I felt him swell to even greater proportions, but after barely a minute, he gently pushed my head back and freed the now-throbbing organ from between my lips.

"Beautifully done, Emily. Now please lie back and spread your legs wide."

I was puzzled. "Sir Joshua, why so? Surely you mean to sodomise me?"

"And I will not disappoint you, my dear. But I want you to witness this final invasion of your oh-so-delightful body. Lift up your bottom please. There, perhaps two cushions should suffice. And now..."

He dipped his fingers into a small bowl by the side of the couch, and brought them up, glistening with whatever lubricant he had procured, and proceeded to plunge one, then two, then three fingers into my tight anus. Again, the stretch, but not as much discomfort as before. He moved them slowly around, separating them to pull on the tight ring. Then, apparently satisfied with his work, he slowly withdrew them, smeared even more lubricant onto the tip and shaft of his penis, and lowered it to the tight entrance of my back passage.

"I want you to watch, Emily dear. I want you to witness the defloration of your delectable tight little hole. I want you to be aware, totally focused on this act of sodomy. Now, do you see my prick, my dear?"

"Yes, Sir Joshua."

"Where is it now?"

"It's - it's pressing on the ring. It's in the opening of my back passage."

"That's right. And what must happen next, do you think?"

"I - I think you have to - to push - to push it inside."

"That's correct my dear. Now watch carefully. And try to relax."

How could I possible relax when he was about to inflict this vile deed on me. I watched with a mixture of trepidation, horror and fascination as he held the shaft of his penis in place with one hand and slowly increased the pressure on my tight ring. I could feel myself slowly opening. Unlike my vagina, which adapted quite quickly to his girth, my anus seemed more reluctant to accommodate him. The stretch became more uncomfortable, even as I watched the bulbous head of his penis begin to invade me. Wider and wider he stretched me, and I felt he might tear me open. The sensation moved from mild discomfort to something much closer to pain. His fingers had already opened me somewhat, or this act would have been impossible. I could hardly bear it any longer.

"Oh Sir Joshua! Please, I beg you, no farther! I fear I'll be torn apart by your - your insatiable prick!"

"Patience, Emily. Just a little more. You simply need to relax a little."

"Relax? Sir Joshua, how am I meant to - OH!"

At that moment, his penis slipped in deeper. The bulbous head seemed to finally force its way past the resistance in my ring and slide inside. Although I would be hard put to it to describe the situation that now presented itself as 'comfortable,' it certainly felt less painful. Before I could protest or even comment on what was happening, I both saw and felt him push deeper.

"Oh my God, Sir Joshua!" I gasped, as several inches of his thick penis forced their way into my tight passage. The overwhelming sensation was of fullness. Looking down, the sight that greeted me was one of erotic depravity. My wide-open, distended and very wet vagina and vulva glistened with copious secretions that our previous intercourse had drawn from me. But behind that, I could see that a significant part of Sir Joshua's substantial penis was now embedded in my rectum. Looking up, I could see Sir Joshua's lean and muscular body, covered in a sheen of perspiration, and on his handsome face a wide grin of satisfaction.

"How does that feel, Emily?" he asked, as his penis withdrew slightly, pulled a little at my tight ring, and then slid deeper than before.

"I - I ..." Once again, I was speechless. The entry had frankly been painful. I felt I could never possibly accommodate the monster that Sir Joshua wielded inside my rectum, and pined for the pleasure it had given me inside my vagina. But, strangely, this was now not only much less painful but, I would hazard to say, was beginning to give me some very unusual sensations of a bizarre form of pleasure.

"Admit it, you young strumpet - you're enjoying having your arse fucked. And it's only going to get better."

Even as I was indeed admitting to myself, albeit reluctantly, that this was much less unpleasant than I thought it would be, Sir Joshua added to the slow, languid but insistent strokes of his penis a stimulation with his thumb of my vulva. There is a point towards the front of my cleft where a very sensitive bud of flesh protrudes. I've heard in gossip among the staff that it is called a clitoris, though that term is not widespread among polite society. My clitoris now seemed to be the focus of Sir Joshua's manual attentions, and the sense of pleasure I was gaining from it now seemed to offset any ongoing discomfort in my back passage.

I moved my gaze from Sir Joshua's grinning, passion-filled face to the pink, wet area between my legs, and to the hard, thick rod of flesh that was probing inexorably deeper into my intestines. I watched with a mixture of horror and erotic fascination as, at its deepest thrust, perhaps two-thirds of that substantial organ was now sheathed in my rectum. The strange thing was that, although the sensations were bizarre, unlike anything I had felt before, the forbidden thrill of what I was seeing and feeling was making me go wild with excitement, and to crave more.

Then Sir Joshua lifted his other hand under my chin, pointing my face to meet his gaze.

"Now Emily; tell me how that feels."

"Quite - quite extraordinary, Sir Joshua. Like - like nothing - I've ever felt before."

The sensations from his penis were becoming more intense by the moment, as each thrust took him fractionally deeper. I could feel the strange stretch and a pulse deep, deep inside me.

"Watch," he commanded, as he pulled slowly back until I could feel that tantalising - and now remarkably pleasurable - pull on the inside of my tight ring. Then he thrust deep inside me, one long, slow but irresistible thrust that made me cry out. For this time there was no slow, probing exploration - just a rushing sensation as the tunnel of my rectum was pulled open to receive his full length. I was momentarily stunned, not just by the sensation of deep penetration and total fullness, but by the sight of a bulge in my abdomen as the end of his big penis pushed to almost its full depth, pressing the skin of my belly upwards.

"Oh my GOD!" I gasped, as I felt the faint tremor of something approaching a climax. Sir Joshua's clever fingers teased my clitoris, even as he withdrew most of his penis - and then thrust it in again, a little faster, possibly even deeper. Our bodies touched, and I knew that I had all of that powerful rod of flesh buried where no man had any right to go. And I was almost ecstatic.

He stopped his thrusts, simply making small movements with his penis that I could feel deep inside me. His fingers were now languidly stroking my clitoris. And I was approaching delirium, now becoming desperate for release.

"Emily, my sweet. You look absolutely divine. You are a creature of sex and sex alone. Please, insert one of your delicate fingers into your sweet, wet cunt, and stroke it against that spot I found earlier."

I was in no position to protest, to say that a lady does not pleasure herself like this. My finger found the place, so sensitive now after so much sexual activity, and the level of my arousal became even greater.

"Wonderful, Emily. So beautiful, so coyly yet blatantly sexual. A picture of wide-eyed innocence and wide-legged depravity in one. A sweet virgin harlot. Now tell me, Emily, do you want release?"

"Oh God yes, Sir Joshua!" I pleaded.

"Then while our fingers join together to pleasure your luscious wet cunt, my prick needs instructions. Tell me what you most want, dear Emily, to complete and consummate your pleasure."

I now knew exactly what I wanted - what I needed. I was desperate for this final act that would give me the release I craved. I no longer cared what was decorous, what was ladylike, what was proper. This was raw, naked, carnal lust of the most wicked kind - and I needed more!

"Sir Joshua. Please - please fuck me. Fuck me deep with your amazing prick. Fuck me - fuck my arse now, please Sir Joshua. Fuck my arse and give me release! Please, sir! I beg of you. Fuck my arse and make me climax."

He did. It was as if some mighty machine sprang to life. His penis - his prick - began to travel like a well-oiled piston in the shaft of my rectum - my arse. Long, deep strokes, almost pulling out - oh the tug on my ring was divine - and then plunging deep into my tight depths. I stared open mouthed as the bulge in my belly repeatedly came into view, marvelled at how deep his penis - his prick - must be going.

The feelings this gave me were so strange and yet so overwhelming; the stretch and the depth and the delicious friction against my inner surfaces. All the while, his thumb pressed and stroked my clitoris, as I joined in with my own stimulation, now frantically rubbing that sensitive spot a few inches inside my vag... my cunt. Yes, my wet, recently fucked cunt, I reminded myself. Wet and longing to be filled again, just as my tight, abused arse was being thoroughly and deeply fucked by Sir Joshua's amazing long, thick prick. I was receiving, initially against my will and now with my full and enthusiastic consent, the fucking of my sweet, sheltered, naïve little life - and I honestly wanted it to go on forever.

And then... And then everything started to spin. My body shook involuntarily, especially from the waist down, while my loins seemed to surge with electrical impulses. My clitoris and my nipples throbbed with an unbelievable intensity, while my - my cunt and arse went into powerful contractions. There seemed to be lights flashing, even as I closed my eyes in the throes of ecstasy. I felt as if a fountain were drenching me. From faraway, someone screamed.

"Emmi? Emmi, are you OK, baby?" Josh was stroking my hair and looking down at me with concern.

"Wha - what happened?" I asked weakly. There was a warm glow in my pussy, a sensation of emptiness in my arsehole and a lot of wetness around my upper thighs.

Josh grinned. "You came; pretty explosively. Your body was shaking, you squirted and you were shouting out all sorts of stuff. Then you screamed - and passed out. It was a bit scary - like The Exorcist but with anal sex - and absolutely amazing. I think we may be able to get the splashes of pussy juice out of the bodice before we return it to the dress-hire place, but the stockings look like a write-off to me. Still, it seems like a good investment. I love the way you really got into the role-play. That drama-school training definitely wasn't wasted. Oh, by the way, happy anniversary, babe." He passed me a glass of prosecco. It hadn't got too warm and still tasted good.

"I've never felt anything that strong before, Josh," I said between sips. "You were incredible. God, you were fucking my arse so deep I could see the bulge your cock made in my belly. And getting me to frig my g-spot while you rubbed my clit just ramped it all up so much. I thought I was going to come when you were fucking my pussy, but when you went for my arse it was even better. I thought..."

Just then, there was a knock at the door. Josh and I looked at each other, then he picked up the towel he'd placed on the chaise-longue before we'd started our role-play, wrapped it around his waist and went to the door of our room. I looked around for something to put on. The only practical thing was a petticoat, so I pulled it on and re-laced the bodice over my breasts as Josh opened the door.

"Hello. Sorry to disturb you, but we've had a report of raised voices and a woman screaming." I couldn't see who was speaking, but it seemed to be the voice of a young woman with an Eastern European accent.

Josh was smiling. "Yes, sorry. My girlfriend got a bit - er - excited. We were having - er - fun and she got a little carried away. You know how it is."

"Hmm. Maybe not so much lately," she replied. I moved towards the open door so that the woman could see me. I realised it was Katja, who was on the front-desk and who had checked us in a few hours earlier. I could tell by the look on her face that she was rather turned on by the sight of Josh, naked to the waist and in just a towel, and perhaps a little intrigued by the sight of me in antique white linen underwear - underwear a little soiled by sex.

"Hi. As you can see, I'm fine. Never better, in fact. Josh hasn't harmed me. I'll try to be a bit less vocal next time. Sorry if we've disturbed anyone." I smiled at the expression on her pretty face.

She looked at us both with a shy smile. "I'm glad you're enjoying your stay with us. If there's anything you need - anything - please ask. I'm on the front desk until eleven."

"Thanks, Katja. And are you working the same hours tomorrow?" Josh asked.

"I - er, no. Tomorrow I'll be on duty from eleven AM to seven PM." I could see that she couldn't take her eyes off Josh's naked torso.

"Thanks, Katja," Josh replied. "Maybe we can come to see you tomorrow when things are a little quiet?"

"Fine!" Katja smiled at us both, then said, "Well goodnight. Please enjoy the rest of your stay." And then she turned away.

"You dirty boy!" I said after Josh had closed the door. "Flirting with the staff, just after you've thoroughly fucked and sodomised your wife. What a way to behave!" But I was smiling as I said it.

Josh hugged and kissed me. The towel fell from around his waist and I felt his cock start to harden again as it pressed against the front of my slit. Just the feel of it was getting me juiced up all over again.

"You know, baby, I was trying to imagine our next role-play scenario. Perhaps Harry Potter showing Hermione some tricks he can do with his magic wand? But now I think I have a better idea. What do you think?" He tilted his head slightly toward the door.

I looked into my husband's handsome face and thought 'why not?'