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Naïve Natalie

Natalie and I had been seeing each other for a weeks at this stage, as we sat cuddled side by side on my couch, with her leaning into me a bit, showing off the contours of her curvy, slightly chubby body. We were sexually active, but the strictly by the book missionary style type of couple. Natalie seemed happy enough with the situation in the bedroom, but I yearned for change, for corruption. Corruption of Natalie. I craved deviance. Perversion. I wanted to defile Natalie. I wanted to violate her. Natalie obviously had no clue as to my true intentions. She only saw the polite, courteous, high achieving college guy I was. Kind and generous. Witty. Funny. Caring towards others. And most importantly towards her. This was all true. And yet it did not tell the whole story.

As we sat together on the couch watching TV, smiling, cuddling, and chatting inane nonsense, all I could think of was how badly I wanted to fuck Natalie in her ass. To spread her ass cheeks wide open, as wide as they would go, and stare into her secret, shameful hole. Her most private space. Her anus. Her asshole. Her rectum. Natalie’s rectum. Her shithole. I still hadn’t seen her asshole properly due to the vanilla nature of our sexual relationship, but I was struggling to wait any longer. I wanted to see her anus so badly. To even just look at it. Observe it. Smell it. And finally of course to inspect it, with all the bodily tools available to me. Yes, the thought of Natalie’s ass spread open like that, her asshole on view, and of what she would be thinking and saying at the same time, was such a thrilling prospect to me that I simply couldn’t wait any longer.

Natalie was such a nice girl. She had those kind of Disney eyes, which screamed goodness and innocence. But which also spelt gullibility and naivety. I would use these attributes to my advantage in convincing Natalie to indulge my sordid tastes, my most dishonourable intentions towards her body. She was about average height for a girl, curvier than most, slightly chubby even, but with the most beautiful round ass. Not too big and not too small. Just enough ass to make my mind explode every time she bent over to get something out of the fridge, or wore her favourite yoga pants. I spanked her a few times around the house whenever she would turn to walk away from me. But never much more than that. And never really in the bedroom.

Natalie had never explicitly said, or even suggested, that her ass was out of bounds. It just seemed that way I guess, what with her being such a good girl type. Her ass was more of a kind of unchartered territory I suppose. Unexplored. That was all going to change that night. I had decided I couldn’t wait any longer. I wanted to taste Natalie’s asshole now. I wanted to lick it. I wanted to press my tongue firmly against her private hole. I wanted to push my tongue in and out of her asshole with force. I wanted to tongue fuck her asshole. And I wanted her to like it. I wanted her to both like it and feel bad for liking it at the same time. I wanted Natalie to become one of those naughty girls. Girls who let guys do anything they like to them. My dick was getting hard just thinking about it. I began to put my plan into motion. Operation Natalie’s asshole.

It was getting late now, and near enough time for bed. Usually we’d both just head up to the bedroom, undress, and get down to business beneath the bed covers. A little fingering, maybe some oral, followed by sex. But not tonight. I had much different plans for tonight. Tonight Natalie was going to become victim to the desires of a sexual deviant. Natalie was lying across my torso still, her attractive ass staring invitingly at me. I moved my right arm from its position on Natalie’s midriff, slowly down towards her ass. I kept it there for a moment. And then began to gently massage her ass cheek. I patted her ass lightly. And then squeezed her ass cheek. Natalie shifted slightly, but didn’t say anything, or signal for me to stop. I continued to both massage and manhandle Natalie’s ass. I told her how much I love her ass. She said nothing but seemed slightly unsure. At this point, I manoeuvred my hand to the top of her yoga pants and slid my hand inside, pushing between the elastic of her panties, feeling the soft flesh of her skin. I kept my hand there for a moment. A moment of bliss. But I wanted more. I wanted her asshole.

I positioned my hand on her ass crack, and slowly pushed my finger inwards towards her asshole. She stopped me at this point, perhaps unsure of my purpose, or simply uncomfortable with the process. I suggested we go up to the bedroom and she agreed. I opened the door of the bedroom and allowed Natalie to enter ahead of me as usual. I watched her ass walk away from me like so many other times before, but this time I followed and stood behind her, putting my hands around Natalie’s waste, and pressing my body into hers.

“What are you doing?” Natalie asked, almost in bewilderment.

“Sssshhhh” I replied, “Just trust me.”

“Ok”, she said, rather reluctantly.

“Don’t speak” I told her, “It’s just me, don’t worry. Just go with it”

“Fine”, Natalie relented, seemingly more relaxed now.

I knew now I had her under my spell. She was mine. And so was her sexy ass.

Still standing behind Natalie, I fell to my knees, so that my head was in line with Natalie’s ass, and slowly pulled down her pants, leaving just her panties remaining. I pressed my nose against them, right into the middle of her ass. Natalie said nothing. Next I placed one hand onto Natalie’s back and gently applied some force, almost beckoning her to bend over. Which she duly did. I was so close now. Natalie’s asshole was so close. Sweet, innocent Natalie, whose beautiful ass I was now staring directly at, with only her panties lying between me and her pretty little rosebud. I pulled her panties down to around her ankles, keeping her in position. Bent over. I stared in wonder at the line of her ass crack. Natalie’s ass crack. I couldn’t wait any longer. I placed my hands firmly on each of Natalie’s ass cheeks, making sure to get a nice firm hold. And I spread them.

To be continued…

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We had - separate - showers, got dressed and went downstairs to the kitchen. Dad was there drinking tea (he was never a coffee person) and reading the Sunday paper. He looked up and seeing Fran, his eyes widened. "Well, good morning you two," he smiled. "I didn't know Fran was spending the night!" "To be honest, neither did I," I replied. "But you won't hear me complaining!" Fran, blushingly, blurted "I hope you don't mind Dr. Monroe..." "Under the circumstances I think you...

How I became a Transexual

I was driving a different way home after work and noticed a kind of sleazy looking sex shop. Not really wanting to go home yet, I decided to stop, it had been awhile since I'd had sex and was horny. I went in and was browsing around the movies section when I noticed there were doors in the back. I went in and opened one up and saw that there was a screen on the back wall and small seat. I went up to the front counter and asked the older gentleman behind the counter how it worked. I paid him and...

She Males

Valentines day gift

It all started a few months ago when we went to the doctor’s office and my wife met Dr Miller. One look at Dr Miller and you knew she preferred women. She had very short and neatly trimmed blonde hair. She stood about 5’5” and 110 pounds. She carried herself like a man but had just enough feminism to know she was a woman. The cute Dr made my wife stop and notice, as I soon found out why. My wife asked me when we left if I thought Dr Miller was cute? I told her yes and she replied, “ I thought...

Lesbian

The Last Song

I had been begging my boyfriend, Austin, to take me to see The Last Song. Austin was actually very sweet and would take me to any chick-flick I wanted, but he had already read the book and heard bad things about the movie, so it took some urging. A blow job and hickie took care of that. We were soon already about halfway through the movie. Personally, I was loving it and was strangely aroused, but Austin rolled his eyes every now and then, calling Miley Cyrus a slut, something I couldn’t...

Different Kind of Prisoner

Copyright© 2004 Twenty miles out from the city I pulled up alongside a car which had two elderly women sitting with the doors open, the hood up and steam coming from the engine. I was two days out of Peterhead prison having to serve my full sentence without remission. The car was a friend's son's which I was delivering for him. I pulled up alongside them and got out. "Can I help?" I asked the two women. "Our car just made a loud bang then stopped," the younger one answered. Younger...

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