Down A Peg

I have always had a non-traditional exploratory approach to sex and sexuality. I've been in hetero relationships mostly but in the dry times fooled with men as well. The urge to feel receptive developed slowly but naturally. While I remained a masculine guy in day to day life, deep down I craved being receptive and feminine. I wanted to feel what a woman feels when a guy takes her. I got a few opportunities to have sensual quick romps with top guys from craigslist. That feeling of powerlessness and submission to another guy's lust was as erotic as the feeling of a warm cock sliding slithering through my sphincters, massaging my prostrate as if I was about to pee.

But in the last one year my fantasies have evolved to a new level. I have come to fantasizing about being pegged by a woman. Pegging is what I read on Literotica everyday, pegging is what I dream about. I naturally wanted to go further down the road of relinquishing my masculine power and embracing the receptive role, that Yin energy. Everyday browsing through a free personals website, I hoped that I would see an ad from a woman who wants to peg a guy, lovingly and sensually. And all I would see would be ads from a dominatrix who wanted money in return.

Then one fine day, I saw an ad that excited me. She wanted to peg a guy for that power exchange I was craving. I consider myself lucky that I am standing today at her door, not knowing how many other willing boys were refused that opportunity. I texted her nervously that I was standing downstairs. I had worn black thongs under my jeans. It was a risky move because I didn't know how far she was into that dynamic. She was standing at the door bare-feet, wearing a short shirt-dress. As I climbed the flight of stairs to her second floor apartment, I handed her the bouquet of flowers that I was carrying. Another risky move, given the non-traditional roles we were about to explore. To my relief, she smiled and gave me a gentle hug in return. While I was taking off my jacket and shoes, she asked if I would like some hot cocoa. I nodded yes as I followed her to the kitchenette. I was surprised to notice that she acted fairly normal while we both stood . Perhaps I wasn't the first boy she pegged.

"Have you done it before?" she asked, looking straight into my eyes.

"You are the first", I replied. I could see the twinkle in the eyes. She turned around and raised her hand high to pick up the cocoa from the overhead cabinet. As she did that, her short dress lifted up from one side revealing her smooth milky butt. She wasn't wearing any panties. I was lost in the moment, ogling her naked rump not realizing that she had turned her head to say something to me. I was embarrassed of being caught in the act even though we had exchanged some explicit fantasies for past few days. As she brought the cup to me, she has a smirk on her face.

As I took the cup with both hands, her free hand grabbed my crotch in one smooth motion while she whispered in my ear -"It's your ass that's gonna be inspected today". My cock started to grow in her hands, as my breathing got heavy, my head lowered in natural submission. I didn't know that acting so receptive came naturally to me. As she unbuckled my belt and pushed the jeans down my legs, it was her turn to be shocked. She burst in laughter and said "I love it how kinky you are". In the moment that followed, my shame carried a sense of relief that she enjoyed my submissive adventurism. Her soft hands were sensually stroking the satin front of my black thongs as my turgid cock was peeking out from the top. Amid all this activity, she had chosen to keep her body at a distance while slowly raising her lips to meet mine. I closed my eyes as her soft lips devoured mine. My mind was confused between kissing a woman while also being fondled as a man who was about to surrender.

Perhaps this was what I was craving for more than a year. It was so sensual being the object of an assertive woman's desire. I was weak in the knees as she turned me around to feel by naked ass cheeks. I had shaved my butt and the areas around the hole last night in anticipation for tonight's romp. She stroked my butt cheeks, pinching them, prying them apart to feel my smooth hole. All this time her breasts were pressed against my back but the only thing I could feel was her hands exploring my ass and her warm breath on my ears. My mind was engaged fully in another dimension of my personality.

She led me to the couch in the middle of the living room, took off my shirt and said, "Bend over on the couch, with knees spread apart, on the cushion". I was here to comply, that's what I wished for, that's what I wanted. But in that moment, I felt the conflicted humiliation of being naked, wearing only girly thongs, in a petite woman's apartment being told to take a receptive position. As I took that position, she pushed the small of my back to adjust my ass to her pelvis. I had lot to learn about being the Yin, today being just the beginning of the journey. She felt my balls sensually with the back of her hand, sending tingling sensations all along my spine, and then very quickly pushed aside my thong revealing my nakedness for inspection. My head lowered, eyes closed, I was imagining how she was devouring me with her eyes, how I was at her disposal for some foreseeable time. She squeezed my balls from behind, while her other hand stoked my rock hard cock. I could feel warmth of her breath near my hairless hole. Oh gosh, how kinky she was!

She pulled out her hands abruptly from between my legs and announced, "Are you ready to be banged?" I could muster a slight courage to meekly reply, "Yes".

"Stay just like this, or you'll be spanked hard." I heard her walk to another room. It must have been only a couple of minutes but the anticipation, the shame and the humiliation made me feel as if she had already spent 15 minutes away. I was looking her way as our eyes met when she walked back into the living room. Her dress was gone, and the only item on her body was a realistic looking cock, supported by a purple harness, dangling side to side as she walked towards me. I was mesmerized and ashamed at the same time. She was smirking as I could only muster a meek smile obeying her command to be in the exact position she left me in.

As she came behind me, I felt her fingers applying a glob of lube around my hole, slowly pressing her finger past my bud. I whimper escaped my lips as she asked me rhetorically, " You like it?". I moaned as she slid her finger in an out past my sphincter, inserting two and eventually three fingers as my hole loosened. This was the power dynamic I had been craving for. Being a submissive plaything for a sexy woman!

There was a pause as she retracted her hands, possibly lubricating her strap-on and wiping her fingers clean. My heart was racing in anticipation and excitement of what was about to come.

And as it arrived, I felt a soft, thick, wet element poking my sphincter with a constant ever increasing pressure. I felt obligated to let my sphincter loose as the cock head won that battle past my sphincter to claim a place in my anal cavity. Her fingers had prepared me well and the lube certainly helped, but I could feel the stinging pain. She held her position not moving forward or backward, her hands having grabbed my hips which told me that she was good at what she was doing. As I got accustomed to the girth of her cock, she pushed further. I was being impaled inch by inch, by a beautiful woman I had just met an hour ago. How crazy was that?

I felt full inside, my hands grabbing the couch firmly as she continued to push past my second sphincter which I had no control over. As I was relishing the moment, she withdrew slowly. That smooth silicone cock sliding out was even more pleasurable that on it its way it. She know how to tease me with her slow pace. But I didn't know her well. What came next made be shriek in pain and pleasure. She rammed her cock in full motion as if it was a mechanical piston. But she had no regard for my pain. She was hungry for the power and I was in her possession to be treated the way she wanted. She kept pistoning in and out of me aggressively for a long time, spanking my ass, reminding me to take it like a bitch! I was loving it. This was what I was here for.

I was tired and sore and eventually she let up a little only to tell me to lie on by back. I did as told, lifting my legs up towards my chest. I had fantasized this very moment, being taken like a very feminine woman in the most receptive position there is, the missionary. Our eyes met. She was like a voracious vixen pouncing on her prey, rage in her eyes, sweating profusely. She reentered me, pushing the back of my thighs for support as she progressively leaned over me. Her naked boobs pressed on my chest, her cock had completely filled me up, her lips coming close to mine. I closed my eyes in shame and pleasure, opening my lips a little for her. She kissed me like a lover, soft and tender as she fucked me slow and firm. There were so many sides to her. I had just met her but that moment felt right. I had given myself to a someone who was taking me with gentle care, as if I was gonna be hers for a while. In this moment of mutual joy and pleasure, my balls exploded and I came hard. She kept kissing me tenderly as the spurts of my semen found place between our tummies.

We kept lying there in post-coital embrace as I felt her breath on my earlobes. I kept wondering if she came but had no courage to ask. She got up in one swift motion asking I had fun. She knew I did and without even waiting for my answer she added,

"I want you to stay the night".

I could only nod my head, while feeling that inner delight. We cleaned up and spooned on the same couch watching TV, she being the big spoon.

I don't remember when I dozed off to a good night sleep.