Midsummer Legacy - Roleplay

Looking down at her, all wet and lubed up for me, I shivered in anticipation. "What do you mean months? I've been wanting to fuck your ass for years..." I knelt behind her and pushed my cock down. It was a bit painful; I was hard as a fucking telephone pole. When the tip of my cock touched her anus and nestled between the soft flesh of her buttocks, I forgot about the roleplay, my wife or her husband. With my free hand I caressed one of her buttocks, using my fingers and thumb to squeeze it hard. Her soft flesh gave way and I felt her anus opening up. Reaching around I did the same to her other buttock, keeping a firm pressure on my cock at the same time. Now, taking my time and trying to become conscious of all the intoxicating feelings I was experiencing, I reached for her hip and pushed.

My first time had been with our friend Rinette during Midwinter, and it had also been her first time. As delightful as that moment had been, seeing my cock disappearing smoothly inside Eleanor's ass was mind boggling. I could see her skin stretching around me, spasming softly a few times before cinching itself around the base of my glans. Eleanor didn't cry out. All I heard was a long moan. Staring down at the glorious sight, I pushed in deeper.

Eleanor's ass was soft and pliable, letting me in easily. As I pushed in gently she moaned faster and faster until I was all the way inside. And I mean all the way. I don't think I was able to do that in Rinette, and the feeling was just amazing. "Pull back a bit and add some lube, will you?" I reached up and grabbed the bottle. Looking back down at the sight of my cock sliding out of her ass, I knew I was grinning like a deranged person. I let a long line of lube fall on my cock, and pushed back inside.

I don't know how long I stood there, transfixed, not moving an inch, just staring at her beautiful ass, and her stretched anus around the very base of my cock. Slowly, imperceptibly at first, Eleanor began to clench her muscles around me. Part of me wanted to ravage her, to take her ass like a beast. And another part of me wanted to savour this feeling as long as I could.

I could feel her muscles contracting, squeezing my hardness. Figuring out that I was not about to fuck her immediately, Eleanor resumed her hip dancing once again. Notwithstanding the fact that she was kneeling on the floor, her face against the wet tiles with a very hard cock all the way inside her ass, she nevertheless managed to twist and turn around me like a belly dancer. Looking down at this spectacle, I had trouble breathing normally.

I felt as if I could die this way and be happy. Yet when she pulled away and back, no more than an inch, the flood of sensations took me by surprise. My instincts took over for a brief moment, just long enough to make me realize that both my hands were on her hips, ready to push and pull. When my hands squeezed her flesh, Eleanor moaned and whispered, "Let yourself go, lover... My ass is all yours."

The next few minutes were a blur of raw pleasure, unrestrained passion and sheer craziness as I abandoned myself to the will of my body. Up to this point Rinette's had been the first ass I'd taken, slowly in our afternoon together, then faster during the orgy. It had been amazing, most of all because Rinette had been an anal virgin, and that she had the most wonderful ass I'd ever seen. Yet this moment with Eleanor was both very similar and quite different at the same time. The fact that Eleanor's creamy white buttocks were lovely was beside the point. She wasn't giving me her virginity either. Instead I was overwhelmed by a woman who not only was used to this, but absolutely loved it. She was allowing me to share into her fetish, a fetish she had obviously been cultivating and exploring for years...

I knew I was fucking her harder and harder, expecting her to ask me to slow down any second. She didn't. I knew I had a big cock, and that I was riding her hard. She was only groaning and crying out in what was obvious and utter pleasure. When I reached my perfect rhythm and intensity, I completely lost sense of all time and space. I was simply lost in the unadulterated pleasures, both physically and emotionally.

I was awakened from that trance by her moans, which suddenly stopped. For a brief moment I opened my eyes in panic; had I gone too far, too deep, too hard? Nope. Eleanor's mouth was wide opened in a silent scream, and her body began to tremble all over. Lengthening my strokes and enjoying every damn last inch of her ass I knew I was also very close to my climax. When she whispered and long, drawled out "Gods..." I felt my pleasure going over the edge.

My orgasm took me by storm, shaking me like a leaf in the wind. I didn't want to stop but soon had too, my cock screaming in lingering pleasure and pain. I had been fucking her as hard as I could. When Eleanor heard me take a deep breath, she shushed me, "Shhh... you wouldn't want our spouses to hear you..." She was breathing hard herself, slowly rising from her prone position to her hands and knees. I looked at her, stunned by her comment, and began laughing.

A few moments later I pulled myself slowly out of her ass, stunned that she had taken me fully inside her. When she sat on her hip, looking at me with a remarkable grin, I leaned forward and kissed her. "So, that is what would have happened if I come to peep on you in the shower?" I asked.

"Why not?"

"Er, because we were married to other people?"

"Aren't we married to other people now?" she asked, still grinning like a cat. When I simply shook my head, smiling, she added, "Now that I know that you enjoy roleplaying that much, I have another idea in mind."

As I watched her get up and wash herself again under the hot water, completely at ease with my shameless gawking of her naked body, I realized again that shy and reserved Eleanor was anything but. Learning about her fetish for anal sex had been a first shock, and this morning's fun was nothing more than extra confirmation. Under that modest, introverted facade, Eleanor was a sexually confident woman that knew what she wanted completely, and was in full control of her sexuality. She was now, obviously, also quite in control of my own sexuality.

We spent the rest of the day in the spirit of our roleplay, stealing hidden caresses and kisses when the others were nearby, acting as if they'd be shocked by them. This morning, more than anything else, confirmed that the choice Nella and I had made was the right one. I loved Eleanor and she loved me back, just as I knew that Tim and Nella shared something precious as well. How long our foursome would last, I had no idea, but I dearly hoped that it would never end.

***

P.S. I've had a few other ideas about the characters form the Midsummer and Midwinter series. I've you've read this far and want more, let me know in the comments or in email feedbacks!