Adult How To

Crafted a Toy

Account of a guy having his initial anal sex experience with a stranger

Spankmasters
May 3, 2024
13 min read
submissivefemale dominationpeggingsubmissionfemdomMade a Plaything
Made a Plaything
Made a Plaything

Crafted a Toy

I would like to thank Erza07 for making this occurrence possible with their remarks!

I'm currently unattached in my mid-30s, leading a fairly successful life in terms of career, education, and experiences. However, being single is quite an inconvenience as the company I keep rarely satisfies me due to the same old routines that leave me unsatisfied. It's as if I've made a wrong turn somewhere along my life's journey without realizing it.

Recently, I've been frequenting hotel bars, seeking the promise of a classic conquest while also appreciating their stylish settings and lack of crowds. Additionally, sitting alone in these establishments is no longer a lonely experience, thanks to the few guests and minimal interaction with staff.

Every Thursday evening, a woman would occupy the end of the long counter and have a few Martinis, much like the James Bond movies. She could easily be described as a classic beauty - with dark straight hair, a narrow face, fair skin, and minimal makeup. She always wore a professional business outfit with a white blouse, a structured skirt, and no pushup, showcasing her elegance. Her attire never highlighted her hips.

This woman would simply sit there and drink, without any cell phone, book, or small talk with the staff or other guests. I couldn't help noticing her presence and admiring her from afar for weeks. It felt as though she knew she was being observed, but there was little invitation for any engagement.

One Thursday, however, she turned her gaze in my direction while the bartender called me over to settle my bill. This incident left me feeling exposed, like I was being stripped of my armor. Her gaze pierced through me, uncovering the real me. I had no interaction with the bartender and simply stood there staring back, unsure of how to handle the situation. The bartender took my focus away and I managed to regain my composure by acknowledging my presence and making my way out without another look at her.

From this moment on, we exchanged looks. Each time, they became more intense, and my performance Sunday nights became less pathetic as I attempted to skirt my nervousness. As I became more comfortable with her, she seemed uninterested in me. I couldn't help wonder what I'd done wrong or if there was something I could've done differently, but she continued to captivate me. Unfortunately, being ignored by her only intensified my desire towards her.

With every Thursday :=M free of her presence, I found myself tortured. It was if I was running in circles, constantly questioning my worthiness and my actions regarding her. Every encounter at hotel bars left me with a desire for her attention that could not be quenched. The more she ignored me, the more I desired her touch. Eventually, I resigned myself to the idea that she'd never be in my life, even though I pushed the idea of her acknowledgment.

These intense feelings compelled me to masturbate myself to sleep, only satisfied by the desire for her attention. My orgasms were more intense without pornography or sexual fantasies, as the essential ingredient was her acknowledgment. My dormant sexual desires were completely revived by her mere existence, followed by a plethora of masturbation sessions. I sought the contact she'd neglected to give me.

In retrospect, I couldn't clearly assess the situation, nor did I contemplate my own sexual yearning that her indifference aroused within me. Or possibly, she'd given me those looks consciously for a specific purpose. At least this is what I prefer to believe, as we've never shared a real conversation and I may not have been able to engage in one even had we met earlier. I long for her acknowledgment.

The game went on until one particular night, when things took a turn. Sitting in the hotel bar and disregarded once more, I was walking home with an erection that would not let up, yet it didn't bother me. It was then that I came across her, smoking outside the bar and she captivated me once more, without any disruptions. I stood there motionless, like a deer caught in headlights. As time went on, her ordinarily neutral expression turned somewhat more hostile. The longer this scenario continued, the more I managed to break free from these chains and I became more conscious of how bizarre the situation was.

I had no idea how to react and it was getting increasingly difficult to maintain eye contact. My voice became uncontrollable and I was starting to sweat profusely. I couldn't endure it anymore and I awkwardly turned my head to the side, refusing to look away from her but also trying to protect myself. I saw a hint of emotion in her facial expressions. The corner of her mouth subtly lifted. She turned around and walked away, only to turn back a few steps later, knowing that I was still standing there observing her. What followed was the most peculiar walk of my life.

Of course I followed her, but somehow I didn't have the courage to catch up to her. A never-ending stream of thoughts filled my head every second, but I couldn't manifest any of them. It seems that unconsciously I chose not to catch up, due to a lack of courage to control this situation or take responsibility for what was about to unfold, just like I always have in my life. The walk ultimately ended in the bedroom of a contemporary and tastefully furnished apartment.

What surprises me the most in hindsight is her expertise. If she had advanced on me aggressively, I would have undoubtedly suffered a panic attack. Instead, she approached from the back and nibbled on my neck, giving me goosebumps. The sense of vulnerability from showing my back to a stranger increased exponentially when she slid my pants down and pressed her hips against my butt. Typically, at such a time, I would eagerly wait for her to touch me and ignore all other parts of my body, yet surprisingly, I was already on the brink of orgasm without realizing it. This likely lasted for some time and the panic subsided as my excitement took over, while my cock remained neglected, which only heightened my desire. I've never felt such intense excitement before.

She skillfully maintained control by continually playing, nibbling, stroking, and pinching me in every sensitive area. I just responded, with no intention of taking the lead. She created the feeling of vulnerability by focusing on my ass. She began with gentle massaging of my buttocks and progressed to more and more direct stimulation. The stroking of her fingers sent tingles down my spine. Normally, I have no erogenous zones on my rear end, but offering a stranger back-stage access to my embarrassing spot only served to arouse me even more. I grew increasingly restless. My agonizing erection needed relief and the urge to push back could no longer be restrained.

This was the moment she likely anticipated, as she grasped my cock and pulled it back forcefully towards my body by its foreskin. I swear I would have endured one of the most powerful orgasms of my life had she not forcibly pushed her middle finger deep into my ass at the same time. What transpired was a battle of sensations between my cock that was dying to explode and my ass that was struggling to remain a virgin. I couldn't breathe and my mind was destroyed.

The panic that surfaced slowly was calmed with a soothing "shh" whispered into my ear and the slow, excruciating, painful but calculated rubbing of my cock held me at bay. My breath became inconsistent at first, then settled, and my mind began to clear up. However, not enough to realize the absurdity of the situation or to become an active participant in the game. I remained passive, my mind catching up with the intense pleasure mixed with the wrongness of it all. And so, her finger gradually fucked me while she slowly jerked me off, too slowly.

This went on for a while and gradually the horniness subsided and my mind was able to free itself. Within me, the desire to extricate myself from this absurd situation arose and I began to loosen myself, which she reluctantly permitted. I turned towards her. She stood there looking at me as if she was in the bar. The fact that I had a finger inside of my ass and my erection was no longer painful aided me in resisting her mesmerizing gaze, leaving me to wonder how this situation would progress.

In hindsight, the notion of taking charge or even leaving never occurred to me. Instead, I sought to avoid conflict and discover commonalities allowing us both to enjoy the encounter. Alas, this decision was foiled as she headed my way, grasping my arm and steering me toward the bed. I eventually found myself pinned underneath her, legs splayed like a vamp, my attempt to resist futile.

The poetic wrestling match that ensued was undoubtedly the epitome of pathetic brevity. I attempted to delicately dislodge her from me, only to be met with a tight grip on my cock and a passionate kiss. She wasn't fierce in her amorousness, but passionate. I gradually faltered in my counterattack, till I eventually forfeited and permitted her to maneuver my arms overhead, trapping them in place with one hand. Her thumb caressed my lips, while her lips whispered enchantingly into my ear, lulling me with a hint of reassurance, as again she infiltrated my ass with her finger. I gulped sharply, but she steered my head towards hers and kissed me tenderly and genuinely. This was an enchanting blend of zeal, inquisitiveness, and ardor, which helped ease my discomfort over the invasion in my backdoor.

She released me and her other hand glided from my cock to my buttocks, simply massaging my anus, presumably as a means of habituating me to my role in the discourse. Her hand relocated to cradle my cheeks and her thumb skimmed my lips, then she whispered in my ear coyly, shushing me while simultaneously probing me once more. I gulped sharply, she turned my head toward her and we kissed again, this time not a passionate embrace, but an earnest, almost affectionate kiss. I've shared numerous kisses with an abundance of tongue, a dearth of tongue, coerced kisses, candid kisses, and awkward kisses, but this session generated emotions I couldn't fathom, fulfilled me enough to tolerate the invader in my anal cavity. This ride carried on before she withdrew.

I wished to roll onto my back, but she again foiled me with a singular gesture, remaining resolute in my spot. She simply donned her underwear and disappeared from sight. I pondered my predicament, reflecting upon the chaos in our encounter, yet the yearning for thrill and vitality was too overwhelming to consider an escape. My heart thumped in my chest, my veins pumped with adrenaline as my mind raced with what could potentially follow. I pivoted, bracing for the aftermath.

The door creaked open, and, to my surprise, I beheld an exquisite and gracious woman strutting towards me. She held a massive dildo in her hands. My senses scrutinized the magnitude, and "gigantic" seemed an inadequate adjective, it perfectly portrayed how massive she seemed. Bold and super confident posture that radiated the aura of a victor. Yet she kept her distance, knowing fully well that I would still strive to coexist with her. Hence, she remained steadfast, and her expression communicated warmth, assurance, and superiority. Perhaps, it was pure glee; I opted not to concur the truth.

This deadlock became unendurable, as a swarm of ideas fermented my thoughts to the brink of collapse. And my latent supplication urged me to open my mouth. However, my voice failed me, leaving a mirthful grin on her face. She strode silently across the bed, slinking toward me on all fours, an entirely desired predator positioned above me - if not for that monolith of a strap-on looming between her legs. The domineering aspect of me cried out at how she approached me, perceiving victory above me. The arousing, liberating part of me vied with my rational self, collapsing under her command. Thus, I prepared as the realization of the next development dawned upon me. [What happened next remains an unrivaled venture in my memory.]

Gradually, she moved across me, beginning at my legs, but this time I shut them at the last second and just lay beneath her, staring wide-eyed and gripping my thighs tightly. Unfazed, she continued to climb up to me and I sensed the dildo brushing past me, coming to rest under my balls between my legs. My erection was once more overlooked, and she amusedly threw another way to control me by teasing my sensitive nipples with her tongue. Despite my obvious discomfort, I felt uneasy about pushing her away. All I could emitted was a weary, slightly agonized breathe.

Apparently, she had abandoned any thought of fucking me in the missionary position and was now nestled alongside me, wearing her strap-on above my cock and stomach. The ensuing kisses were tender, her hand tenderly stroking my cock and body, rebuffing any contact with my sensitive glans, as I enjoyed the slow-building arousal from the side. She expertly increased my desire, which had vanished due to the shock, until it reached an unbearable state again, refusing to grant me any reprieve.

Everyone has three responses in their brain for stressful scenarios, established eons ago. Flee, fight, or pretend to be dead. The concept of regaining control over this situation no longer crossed my mind, so fighting was out of the question. She gradually increased the pressure, my aching erection yearning for relief, the discomfort of my nipples intensifying, the angry strap-on beginning to hump me more powerfully. As always, everything progressed at a slow tempo, and it overcame my instincts to flee. As a result, my primitive brain was left with merely the option of playing dead. She recognized it, my subconscious slowly acknowledged it, and for her, it was just a matter of waiting until I accepted the truth of our interaction up until that moment.

The thought of rolling onto my side, of being able to press my painful, erect cock blissfully into the cold, soft mattress, the thought of escaping from her tender kisses, the inability to withstand the overstimulation of my nipples prompted the thought of offering my back to her. It seemed like a small price to pay for salvation.

Of course, she quickly caught up with me and so I ended up as a little spoon. The reward for my compliance came in the form of a subtle, calming stroking of my penis. Her strap-on, in its new resting place between my legs, slowly dry humped. The mild stroking of my cock, the feeling of being subjected to the looming threat between my legs prompted a previously unknown horniness in me, a type of horniness where you want to be deeply touched, but not in the ordinary manner. It arose from the depths of my soul. It was a desire to be intimately explored, and thus, without ever explicitly expressing it, I started to go along with the woman behind me to fuck me. I desired to follow this unfamiliar feeling to its core.

Once again, she took away any reprieve from me. She wouldn't allow me to fully reach this new sensation, changing the pace of her dry fuck, intentionally avoiding me and the moans I was suddenly unaware of, until I sighed in irritation. Another aspect of this encounter that is impossible to shake is that she made me her toy and then even made me beg for it.

The irritation faded as all the air abruptly left my lungs, as she abruptly forced her strap-on deep into me. All thoughts were obliterated, and once more I heard soothing shushing behind me. Simultaneously, her arms surrounded me tightly, in a protective manner. She securely pressed my now upright head into the pillow with her cheek as she continued to whisper "shhhhh" into my ear. I was instinctively working to regain my composure and breathe properly, and my fight-or-flight instincts refrained from surfacing. A sensation arose in my brain that defied description.

Perhaps the best way to express it is to be completely immersed in the most thrilling suspenseful, action, porno, and horror film simultaneously, or perhaps like experiencing a skydiving jump. This feeling gradually receded, but just enough to enable additional thoughts to seep into my awareness. This sensation arose from my ass, which had subconsciously communicated its disapproval of this unwelcome object from the onset, and which now began to move back and forth. From that point forward, I was oblivious to the person behind me. I could only sense the thrilling experience in my mind, the loathsome foreign dildo in my ass.

My thoughts were trying to make sense of two different emotions. Then, abruptly, a new feeling insinuated itself into my brain - a craving for intimacy, a yearning to be caressed. With some effort, I yielded to it and sighed with every action she executed. The woman seamlessly coaxed me further into this feeling by rewarding soft groans with forceful thrusts. I remained immobile as she took me like a sex-crazed canine, plunging deeper and deeper into the sensation of total submission. I don't recall how long this state endured; I also can't fathom how long a woman must sodomize a man with a dildo before she is sated.

After a spell, the dildo ceased to feel excruciating but, rather, average, and the turmoil of exhilaration and the urge to be touched coalesced with that familiar passion and my erect penis pulsated with each of her digs. I realized I needed to terminate this episode and recognized I wouldn't derive satisfaction from her. I decided to take control instead. She, however, didn't make it simple for me, by pushing me harder and harder with every thrust, making it difficult for me to guide my emotions from pure excitement to typical desire. And so, these sensations in my brain, the thrill, the feeling of being at her mercy, the feeling of being touched so intensely, and my lust increased until I went out of my mind once more.

Before I was even fully conscious of my climax, I was altered and only became lucid in the last throes of what was the greatest orgasm of my life. When my body stopped quivering, I recognized that she had ceased sodomizing me, but there was still a strap-on inside me. Abruptly, clarity pressed on me like a powerful wave, and I was capable of thinking rationally for the first time in weeks. The sole coherent thought that crossed my mind was, "what on Earth am I doing here!" Instantly after, my fight response arose, and I wanted to separate myself from her and that device within me. The fact that she only hesitantly allowed this and I had to wrangle my way free likely served as the climax of our encounter for her. I still struggle to comprehend this now.

Thus I lay there in the most profound embarrassment of my life. Knowing her gaze was upon me, I instinctively reached for a duvet and attempted to hide myself. Paralyzed with embarrassment, I simply continued to lie there. She obviously deemed she deserved a smoke, which I discerned from the sound of a lighter. I have nothing but shamefulness to divulge here. I didn't want to be seen by her. I believe this dragged out for a while.

Exactly what she was contemplating, was she content, amused, or both, these thoughts were ruthlessly abbreviated when she exited the bedroom with my blanket in tow, without casting a glance back. Now left by myself in the room, my escape reflex encountered no opposition. I dressed hurriedly and approached the exit. I froze on the threshold, about to face her in the apartment. Fear of encountering her prompted me to sneak along the hallway and find that she had left the apartment door open, as if signaling my departure. Glancing back, I wonder if that was induced by her kindness or a last blow to my masculinity.

A few minutes later, I found myself on the sidewalk next to her house, wandering aimlessly for hours. Calling for a taxi didn't even cross my mind as my intellect was engaged in trying to understand what had transpired, as if it could have averted my circumstances.

It's been a few weeks since that day with sleepless nights. I'm lagging far behind at work and every Thursday I stand across the street from that bar. I ponder what transpired that day.

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