Loosing my anal virginity (a love story)

standing with a strap-on covering her tits

We had gone back to the apartment after a lovely dinner out. We had done the whole nine yards, pre-dinner cocktails, hor d’oeuvres in front of dinner, dinner, dessert, coffee, and liqueurs, followed by a lovely night out at the theater. So, there I was sitting on Michelle’s couch, a little tipsy, but feeling happy and still a little surprised at being here. It had been three months since we first met. I noticed her right away, that pretty smile framed by her shoulder-length black hair, the pleasing oval of her face, with its high cheeks and those bright, penetrating eyes, the kind that you would swear went straight through you like a laser light, and to the depths of your soul.

I had never considered some of the things we had tried up to know. It started innocently enough, a few light playful swipes on my bare rump, a seemingly random brush of fingertips against my anal cavity. But from there, things progressed. I remember the first night she kneeled over me, my hands tied tightly in silk scarves and bound to either side of the headboard. She had seemingly towered over me, teasing my manhood with a combination of light strokes, followed by light strikes of her gloved hand and palm, combined with gentle and not so gentle squeezes to my groin, to the point that I was sure my eyes had rolled as far back as they could in reaction to the combination of pain and pleasure in reaction to her knowing, considered touch. From there came the crop, and more forceful use of her hands.

At first, I didn’t know how to react, or even for that matter if I had wanted to. But I slowly found myself unable to resist her charm, her womanhood, and, her power. She overpowered you in countless ways, physically, mentally, spiritually. As our bodies entwined and we shared the pleasure of so many countless moments, I found myself wanting more and more to surrender to her, to let her have her way with me, as our bodies, hearts, and minds met and melded. Oh those wonderful nights of pain and pleasure, the lovely smell, touch and feel of her sex against my lips, my tongue searching her longingly, passionately, lapping like a cat lapping up milk, the sound of her breathing combined with the movement of her body in reaction, driving me to distraction, lust and desire. I had reached the point where I had become consumed with wanting to please her, for the lovely, wonderful taste of her on my lips to never fade away.

So long anal virginity

And so we came to tonight. Michelle had already introduced me to anal play. I remember the night she stood in front of me, slowly drawing on the long, beautiful, shinning over polished latex over her hands and up and over her elbows. They almost seemed to disappear into her armpits, the illusion of sex and power they created overwhelmingly alluring and seductive. Next came the outreach of her hand as she drew me close to her on the bed, followed by the exploration of my body, and the first penetration of my anal cavity by knowing skilled fingers. I tensed at first but as she spoke to me in that soothing way, I lost myself in her gentle, overpowering gaze; I had surrendered. I remember her approving chuckle when I eventually came all over my stomach, while three skilled fingers probed me in the most intimate and personal part of my body, it was heaven on earth.

She called to me, and I got up. As I neared the bedroom I heard the soft music, and the nearing glow of light coming from the room. What was that smell, lilac, no… raspberry, … I wasn’t sure. My anticipation of her touch and the surrender to the lust and anticipation of the night was playing tricks with my mind. I stepped into the room. She stood there, bathed in the gentle candlelight. She held out her hand and I took it on my own, held it to my lips and watched it drop away as our lips met. Our mouths opened and our tongues found each other. She had a way of kissing you that made you convinced she could kiss you deep inside yourself; I had never experienced anything like that before we had met.

She pulled back so I could look. How do I look she laughed wickedly. She knew full well my answer. She was dressed in 4-inch heels, stockings running up her long, beautiful legs until they got lost under her robe. She had freshened her makeup and reapplied her lipstick with a skill I hadn’t seen before we had met. It was done with an obvious eye to creating a look of sophistication and allure. On her hands, oh bless her soul!, she wore the most beautiful black leather mousquetaires; they had little pearl buttons that disappeared up the sleeves of her robe. Combined with the pearls around her neck, and the loveliest pearl earrings, she presented a figure that could overpower any man.

You look more lovely then I can describe I said. I thought to myself, boy that must sound stupid, but I meant every word. I had never seen a woman so capable of presenting herself in such a frankly sexy way, where you more noticed the power, confidence, and womanhood she exhibited, then you did the fact that you were standing in front of the sexiest vixen you had ever known in your life. Here, darling, she said loosening my tie, we aren’t going to have any fun with you dressed like that. The tie seemed almost to undo itself, followed by my shirt, which fell from shoulders and onto the floor to be followed by the gentle, sensuous touch of her leather-encased hands and arms against my skin. Soon, I lost my pants and watched her deftly slip my shorts off of my body, holding me gently by my arm as I stepped out of first one leg, and then the other. I lost my balance and as I fell against her, her hand came up against my groin; I felt that touch of pain and pleasure. I knew she would have her way with me and that there was nothing I could to stop it; did I really want to…hardly.

Oh my, she said, my cock had swollen to its full size. You are so ready, she said, but I don’t think you are ready enough. She pointed to a chair next to the bed. We are going to have fun tonight she said as she led me to it; I am going to show you just how much control a truly powerful woman can have she whispered as she leaned forward and lightly kissed my cheek and neck. I looked down on the chair, but before I could say much of anything she had me over it, and lightly put her hands on my shoulders, pushing ever so lightly downward; I tensed for a moment as I realized what was happening. I felt its plastic tip part my anal cavity, and I felt its width as I slowly slid down onto it. I looked up at her, watching the twinkle in her eye. We had played with sex toys, but I never had her suggest I try sitting on the plug that now so fully filled me. I felt my ass against the bottom of the chair. She continued to look at me; oh my she said, you took that so well, I am very impressed darling. Oh, she said, pulling back, something looks wrong. I think a look of wonder, or maybe it really was worry, came across my face. Here she said, leaning down and placing her gloved hands on either of my thighs, just aside my balls; she pushed down, and I felt the plastic object in my ass slide up ever so slightly, more tightly filling me. Look at me she said; I looked at her face to see the lust and feeling of control she obviously felt at my situation as it rolled across her face. She chuckled, and mixed the light message of her lovely gloved hands with the occasional downward push, chuckling softly as I winced in time with her downward push.

There I was prostate, really unable to move. I was harder now then I could remember. She mixed-light kisses, with light bites on my lips, cheeks, and neck, while she stroked my swollen member. I began to perspire slightly, which seemed to increase the frenzy of her bites and strokes. I began to breathe deeply; then just as suddenly, she drew back, placing her hands on her lips. Oh no, you don’t she said, with a big smile on her face. Come, darling, let me help you; she reached under my armpits and I could tell she wanted me to stand up; not that this was hard to ascertain. Soon, I was erect, in more ways in one. She walked around to my side, and from a couple of feet away surveyed her handy work. Then she came closer, placing one arm around my waist, the other, its hand resting on the plug, so firmly placed in me. She kissed me, and then pulled away slightly. This was followed by the push of the plastic cone against my straining anal cavity. I would wince, and she would chuckle. She raised her hand to my face, and said, open your eyes and look into mine; don’t close them she intoned strongly. We kissed, eye upon the eye, the occasionally feel of that plug being pressed in place, followed by her soft moan, as I winced in reaction, our lips and tongue intertwined, mouths pressed so firmly and fully together. Finally, she pulled away breathlessly; oh I am so ready she said, taking my hand and guiding me to the end of the bed.

“On your knees please,” she said as she helped me to the floor.

She sat on the bed, and then resting on her arms, drew my lips to her beautiful, wonderful, muff. I felt her hand push strongly against the back of my neck, driving my face up harder against her clit and vulva. My tongue darted out into her lovely, tasty, musky, beautiful women hood, as I listened to her breathing. It quickly deepened and grew more rapid; I felt her shudder, and her fingers in my hair pulling my head back forcefully with a gloved hand, as she sat more upright, her body shuddering in a cascading shower of moisture, muskiness, sex, and orgasm. Again she insisted, driving me again into her wonderful moistness. She came again shortly and sat up fully. Her hands reached down to my face and rising, I saw her mouth a word of thank-you, as she shuddered for what seemed an endless moment. Eventually, she stood up and drew me to my her. We kissed and I again felt her wonderful leather hands as they gently stroked my cock, interspersed moments of gentle caress followed by the most skillful and deliberate painful squeeze.

“On the bed,” she said, “on all fours, please”

What was next; I knew. She reached over to the night table and drew out a latex glove which she snapped on over her right-hand leather-gloved one, followed by a second glove over the first. I tried to relax as I felt the plastic object slowly withdraw, to be replaced by first one gloved finger and then a second. I had winced both as the plastic plug had been withdrawn and as her first latex-covered finger slid slowly into me. With her second finger, her exploration grew more aggressive; I knew she had rotated her hand, and curled upward, by the reaction I felt telling me that my prostate was enjoying her undivided attention. After a few moments of gently caress and prodding, her hand withdrew slightly to allow a third finger into me. I had felt mixed emotions when she had first asked me about allowing her to try this. But, I had grown glad I had agreed; as she stroked, prodded and as her fingers slid in, out and side to side, I had come used to feeling a sensation similar to her lovely technique on my swollen member. It was like being blown form inside, her fingers replacing lovely, soft lips, mouth and tongue. She slowly stroked my back as she paid attention to me. I was sweating profusely now, and looking up and back over my shoulder, I could see the lust and desire in her face, into which she would lose herself. After a few more moments she slowly withdrew her fingers, the latex gloves, finding the trash can next to the bed. I was breathing heavily, and struggling to regain myself as she walked to the closet, and withdrew a box.

Standing with her back to me I could tell she had emptied its contents, dropping the empty box on the floor. She turned around to face me, a truly devilish grin, half desire, half lustful smile on her face. I watched her step into the leather loop and watched the artificial appendage position itself over her lovely womanhood. We had talked about this next step but never had seemingly decided to go forward. She reached for a leather strap and drawing it around her hip drew it through a buckle, the strapon now finding its place firmly in her front. I hadn’t said anything, partially fearful, nervous and awed at the power of her person as she adjusted the device. My she said, I do look good she said as she began to draw forward toward me. I know we haven’t talked about this darling she said, but I know you want this. I looked at the appendage only inches from my face. She bent down and kissed me in that light, saucy and cheeky way of hers. Standing up she said, let’s have some fun then.

I watched her reach under the device and it began to emit a soft hum; combination vibrator and cock darling she said. Why should you have all the fun? I could see it was already having its effect on her. I had never seen Michelle so lust-filled, and so powerful. It was both beautiful, and intimidating, frightful and desireable.

She walked behind me, and after applying something said ready? I never got a chance to reply as the device slid into my well-prepared ass. She stopped partway in. Are you ok? I was a little surprised to hear that. I don’t know where my mind was and this threw me off. I gulped, struggling to accommodate the object already in me. I think so I said. She replied with no words, but action instead of as the artificial device slid further into me. I could feel it in me; I felt as though I would explode from its size and fullness. She pushed again and I felt her body against my ass. He leathers gloved hands came down to my ass and back, I felt the gentle touch and rubbing for a moment. She was breathing heavily and I again felt her shudder. Oh she said, I am so going to fuck that ass!

I felt her drawback and then felt the accompanying forward thrust as the device struck home. Within moments Michelle had developed a rhythm which I felt powerless to resist as I rocked in time with her thrust and the driving of the device within me. I was surprised at how good I felt and marveled at how the combination of pain and the pleasure I felt as my prostate was brushed by her device rolled over me in waves. Michelle shuddered again, and moaned softly, without letting up. We fell silent, the sound of our sex, the vibrating tool, mixing with the sweat of our bodies, the silence of the room and our heavy labored, lust-filled breathing filling the void. I ached both for her to stop and for her drive me even deeper. I pushed as hard against the tool as I was able, I swore, imploring her to fuck me harder, and deeper. She responded. Faster we went, harder, deeper; Michelle screamed, shuddered and fell against my back as I stood up slightly. I felt her tongue, lips and hands-on me; lust was replaced by tenderness. I felt tears welling in my eyes, I couldn’t explain how I felt; I felt loved, relieved, taken, and, owned intimately. I felt safe, but exposed, tenderness, while also knowing she had accepted my willing surrender to her, and with it my control to her, my very soul. She withdrew slowly.

Oh, you were wonderful she said as she came around to the side of the bed; then I felt her hand reach for my sex. It wasn’t a loving touch, it was deliberate, powerful, controlling. 6 strokes, 10, 12, it couldn’t have been much more. I exploded, my juices covering the sheets below me, her hand pumping me quickly, mercilessly, deliberately, powerfully. Eventually, she stopped, and her hand withdrew. I was lost, exhausted, soaked in sweat and struggling to regain control. I felt the plastic plug again enter into my anal cavity. I was so surprised; I looked at her. Well she said, you didn’t think I had finished yet, had you? I looked at her as she came around to me, and reclined with her back against the backboard of the bed, her arms reaching out to me so that soon my head was resting on her lovely shoulder. I looked at her. Her leather-gloved, the hand came to my cheek; she looked into my eyes oh so deeply, I sensed she was looking for something. Darling she said, her lovely soft gloved hand tenderly stroking my cheek and hair, you are mine, for now, and evermore. Looking in her eyes, I knew she was right.

Last Updated on 1 year by pseudonymous