Gay First Time Literotica

At the age of thirty, and completely heterosexual, it became apparent that I derived significantly more pleasure from male anatomy than female.

To provide some context, I was not a novice in sexual matters, nor had I experienced any past trauma, nor was I aware of any innate homosexual inclination prior to this event. My romantic history was predominantly with women, and our physical intimacy was a regular and pleasurable occurrence. While not adverse to or fearful of homosexuality, I had maintained a distinct "gay-adjacent" stance.

During my childhood, a family excursion to San Francisco's Castro district ignited a fascination with homosexual culture and a curiosity about the basis of male attraction towards one another. Witnessing men embrace and kiss held me captivated. In my college years, as an art student, I was deeply engrossed in the study of human anatomy, both male and female, the practice of figure drawing, and an admiration for classical Greek, Roman, and Renaissance sculptures, particularly those that honored the male form. I appreciated the depiction of well-defined male musculature, devoid of the exaggerated, almost caricatured proportions seen in contemporary bodybuilders.

Following my academic pursuits, I even engaged in anatomy modeling, possessing a well-developed physique. While proud of my physical build, I felt a degree of modesty regarding full nudity, opting for a posing strap—essentially a G-string—during college art classes, but posing completely nude for smaller, private drawing sessions.

On numerous occasions, I had been approached by gay gentlemen, an experience I found flattering rather than offensive, though I never reciprocated their advances. I had, on a few occasions, explored my own anus, but solely within the hypothetical context of heterosexual encounters, considering how a woman might pleasure me from behind. On one instance, in my girlfriend's absence, I utilized her vibrator on my posterior. The resulting sensation was overwhelmingly blissful, leading me to feel a pang of envy towards gay men for their perceived greater connection to such profound sensual gratification. My inability to fully insert the vibrator led me to conclude, "I could never be gay; my anus is simply too constricted."

This background information is crucial for understanding the magnitude of the transformation I underwent, or rather, that was revealed, within a single day. Regardless of any internal resistance I presented, it was ultimately overwhelmed by an intense surge of desire for passionate, profound, and lustful penetration and domination by a man.

At the time of these events, my profession was as a personal trainer at a local gymnasium. I catered to a diverse clientele, including gay, straight, male, and female individuals, and had cultivated a reputation as a highly competent professional, supported by my own physique. As previously mentioned, I had undertaken some modeling work that necessitated a muscular frame and an attractive countenance. My portfolio also included some runway and magazine features. While I possessed a pleasing appearance and an athletic build, I recognized these attributes alone were insufficient for a sustained livelihood. A former college girlfriend had encouraged me to submit nude photographs to a women's magazine, and upon receiving a request to travel to Los Angeles, I ultimately declined, experiencing a bout of apprehension.

Scott, one of my gym clients, was also a close confidant outside of the professional setting. My perception of him was never sexual; however, he frequently invited me to various social gatherings catering to the gay community, often accompanied by his partner. I consistently felt at ease at these events, whether they were themed parties or more formal cocktail gatherings, largely due to my enjoyment of showcasing my physique and the positive attention I received. My sense of masculinity remained unthreatened, and I often quipped, "I'm secure enough in my own sexuality to wear a pink shirt."

One afternoon, Scott extended an invitation to an adults-only pool party hosted at the residence of a wealthy gay couple for whom he was house-sitting. He mentioned that while the attendance would be diverse, the majority would be gay men. He also expressed a desire to introduce me to his circle. I readily accepted, as his aspiration to be associated with a desirable heterosexual man mirrored my own inclination to be admired and sought after. There was also a faint hope of encountering an attractive woman.

The day preceding the event, I completed my workout, feeling confident that my sculpted arms and thighs, well-defined abdominal muscles, prominent chest, and shapely buttocks would undoubtedly attract attention. While not boastful or arrogant, I was aware of the genetic advantages I possessed, having received numerous compliments, though I acknowledged that not all credit was solely mine. Subsequently, I visited a tanning salon to enhance my skin tone.

Aware of the pronounced preference among gay men for tanned complexions, I wished to avoid any perceived offense due to my pallor. Furthermore, I meticulously shaved my genital area, as the swimwear I intended to wear was my posing strap - essentially a small pouch designed to accentuate my anatomy - and I did not want any pubic hair detracting from the overall aesthetic. Upon completing the grooming, I observed my reflection and experienced an immediate erection. "Astonishing! If I were gay, I'd certainly find myself attractive," I mused. This sentiment, admittedly, stemmed from a degree of narcissism. It also served as an indicator that, on some subconscious level, men did indeed ignite a sexual response within me. A heterosexual individual would likely not experience arousal upon viewing their own shaven genitalia and smooth anal region.

Upon arrival at the party, attired in shorts and a polo shirt, Scott immediately intercepted me inside the house. He advised me that an announcement might be made later, making the remainder of the gathering clothing-optional. He sought to be considerate of any potential discomfort I might experience in the presence of numerous naked gay men. I assured him that I would be perfectly amenable to the situation.

He instructed me to change into my swimwear and join the others by the pool. I proceeded to a bedroom, where I disrobed down to my G-string. A quick glance in the mirror confirmed the optimal positioning of the garment to encompass my anatomy, and my penis began to swell slightly, tautly stretching the narrow band of fabric that covered my anus. I noted, "This is going to cause chafing if my erection intensifies." Consequently, I cautioned myself, "Be sure to avoid getting aroused."

Stepping out onto the pool deck, I found myself overlooking an infinity pool that offered a panoramic vista of a lush valley dotted with opulent residences. A swift assessment revealed that my swimwear was the most revealing of all present. While most gentlemen were clad in Speedos, boy-shorts, or similar attire, none displayed their buttocks quite as openly as I did. "Well, dressed to make an impression, I see," Scott remarked.

"Indeed, I had assumed that gay men appreciated a more ostentatious display of their attributes, anticipating a greater number of guests attired similarly to myself. Nevertheless, such is life," I responded.

Scott proceeded to escort me around the pool area, facilitating introductions to various attendees. Individuals were either reclining on lounge chairs, spread out on towels across the lawn, or perched on the pool's edge. I recognized only a few individuals from my workplace, the gymnasium. Curiously, only one woman was present, the wife of another male guest, and she was not the attractive companion I had somewhat optimistically anticipated encountering. Again, "such is life."

The assembled men presented a spectrum of physical appeal, ranging from average to exceptionally striking. My evaluation was strictly from the perspective of a fitness professional and an admirer of anatomical aesthetics. Out of approximately thirty individuals present, five men possessed the striking appearance and physique of models, embodying the visually oriented segment of gay culture exceptionally well.

Scott guided me through the pool area with a performative flourish, pausing periodically to offer additional commentary, which necessitated my turning a full circle, allowing for comprehensive inspection of my nearly unclothed form. The reactions from the guests were largely predictable; gay men would scrutinize me from head to toe, often with an approving smile, then eagerly whisper to their companions. The heterosexual individuals offered polite nods, attempting to avert their gaze from my conspicuously displayed crotch. One of the exceptionally attractive gentlemen, Ted by name, removed his sunglasses as Scott announced his presence.

Ted was reclining on a beach chaise atop a pristine white towel. His physique was, in my estimation, a perfect embodiment of classical Greek statuary—remarkably muscular arms, chest muscles sculpted into defined slabs, an abdominal region showcasing an eight-pack, and powerfully developed thighs complemented by elegantly contoured calves. However, in contrast to the diminutive penis often observed on steroid-enhanced bodybuilders, his square-cut boy shorts revealed the distinct outline of a generously proportioned penis and substantial testicles. I was compelled to acknowledge him, albeit silently; he represented the pinnacle of masculine beauty, irrespective of sexual orientation.

A sense of slight intimidation washed over me as Scott departed following our introduction. I stood before Ted, casting a shadow over his aesthetically pleasing, tanned physique, his finely chiseled facial features, and his soft, wavy dark hair. His lineage appeared to be Italian or of another Mediterranean origin. I could discern no apparent imperfections. "Hello, Darren," he remarked, abruptly bringing me back from my reverie. I realized I had been captivated by his presence while my mind processed these observations. His gaze slowly shifted from mine, tracing a path down my body to my penis, proudly displayed within my minimalist jockstrap. He paused there momentarily before deliberately retracing his gaze upward, eventually locking eyes with me.

He offered a smile of apparent approval. I reciprocated the gesture, also with an approving expression. "A battle of glances," I thought. This intense scrutiny and overt sexual interest, originating from someone as aesthetically perfect as Ted, was undeniably a positive development for me. I found myself drawn to his desire for me, and indeed, I wished to prolong this intriguing interaction. "Would you care for a drink?" I inquired. I had no knowledge of the beverage selection or location, yet an inexplicable urge to serve him compelled me.

"That would be splendid, perhaps some white wine," he responded. As I casually sauntered towards the house in search of the requested wine, I deliberately stooped to retrieve a small pebble from the deck, tossing it aside to prevent anyone from stepping on it barefoot. My stooping motion, originating from the waist, was strategically designed to offer Ted an unobstructed, deep glimpse of my virginal anus, barely concealed by a strip of Spandex. Glancing back over my shoulder, I observed that Ted had indeed repositioned his sunglasses atop his head and was propping himself up on one elbow, clearly observing my posterior as I moved away. A smile flickered across my face as I registered his gaze, and he returned it with a sheepish expression. "I do enjoy provoking such reactions," I reflected inwardly.

I returned bearing his white wine, along with a glass for myself. His eyes remained fixed on the level of my penis, and he took his time acknowledging my retrieval of the beverages. I relished the flirtatious exchange, despite having no intention of escalating the situation. He then extended his legs to either side of the lounge and subtly adjusted his package beneath the form-fitting nylon fabric. His penis had become somewhat engorged, and the outline of its head was clearly discernible—a magnificently defined, almost piercingly prominent glans. It was now my turn to feel a sense of admiration. "Touché," I acknowledged to myself. My G-string began to exert a tighter pressure within my gluteal cleft, and I realized my penis was experiencing a slight enlargement. "What precisely about this scenario was causing me to flush and my heart to race? I am not gay; my orientation is definitively heterosexual. And yet, I find myself developing an infatuation with this man, and I wouldn't object to kissing his captivating lips or tracing my fingers across his magnificent chest, down his sculpted abdominal muscles, to that prominent outline of a substantial penis," I pondered.

Our conversation continued with further pleasantries, and it seemed as though every exchange carried a sexual undertone. Despite my efforts, I found myself unable to disengage from the flirtatious dynamic. Concurrently, two other processes were unfolding: I was attempting to decipher the origin of my feelings, which suggested a desire for physical intimacy with him, and to understand why my body was reacting in this manner when my rational mind affirmed my heterosexuality; and I was visually tracking the rivulets of sweat as they meandered down Ted's smooth, powerful pectoral muscles, across the ridged terrain of his abdominal muscles, and disappeared into the upper edge of his swimsuit, resting just above his pubic bone. These conflicting internal forces left me bewildered. One perspective felt entirely rational: I understood my sexual orientation; the other felt intensely pleasurable: I desired to be the object of a gay man's sexual affection.

Unbeknownst to me, the couples and other heterosexual individuals, with the exception of myself, had gradually departed the gathering. It's possible that Scott had also briefed them regarding the impending transition to nudity, but they perhaps did not share my degree of comfort with such a development. Scott then made the announcement, "Alright everyone, clothing is now optional!" eliciting a resounding cheer from the approximately fifteen to twenty remaining gentlemen.

Ted met my gaze once more and rose to his feet. Without breaking eye contact, challenging me to hold his stare, he inserted his thumbs into the waistband of his shorts and pulled them down to his thighs. His attractively swollen, semi-erect penis, which had been resting horizontally while he was seated, now shifted from its position against his abdomen and dropped forward, resembling a freshly felled tree. It settled at a forty-five-degree angle from his body, appearing heavy and engorged with blood.

He was deliberately provoking me with his physique and, subsequently, with his penis. I acknowledged a secret, fervent desire to engage with him intimately, yet my mind attempted to impose a logical barrier, reminding me of the impossibility, given my declared heterosexuality. The fabric situated between my buttocks began to constrict more tightly around my anus as my penis commenced its engorgement. "Aren't you going to join us?" Ted inquired, gesturing towards the assembled men, who were now all devoid of swimwear or any other attire.

I rose to my feet, acutely aware that he was directly questioning my asserted heterosexuality. This was a necessary affirmation, primarily for my own self-validation. I simultaneously removed my trunks, letting them fall to my ankles, and then straightened to my full height. My fully engorged penis sprang forth as it was released from the confines of the posing strap. I hadn't anticipated its significant enlargement, and it was now gradually extending away from my body as it continued to harden. This presented a dilemma. Experiencing an erection in the presence of these men would imply my homosexuality, or at least a strong inclination towards it. I felt compelled to conceal my erection and consequently turned sideways to face Ted. This maneuver, however, only exacerbated the situation, as he could now clearly observe my substantial penis growing larger and more rigid in profile. I searched for a means to obscure my hardening erection.

My attention was drawn to three gentlemen, also possessing the model-like attributes I admired, splashing in the shallower section of the pool. "I need to cool off," I announced to Ted, and promptly submerged myself in the water. My blood-engorged penis felt as immense and conspicuous as a rescue buoy just beneath the water's surface.

The three men immersed in the water were all exceptionally handsome and well-built—undeniably attractive gay individuals. One of them extended an invitation to participate in a game of chicken fight within the pool, intending to create an even number of participants. If I were to stand fully upright at that moment, my burgeoning erection would become evident to everyone, thereby revealing my true feelings to all the men present. I was reluctant for these three model-esque individuals to perceive me as gay, yet I agreed to join the game, as it provided a plausible justification for remaining in the water and engaging in playful splashing.

I volunteered to be the base for my teammate, Dylan, and swam underwater between his legs. His thighs and buttocks were the epitome of athletic musculature, perfectly sculpted. His pubic area, like that of all the gay men at the party, was meticulously shaven, and his skin possessed a smoothness akin to polished marble. His tan line indicated that he, too, favored G-strings. At the very least, I had correctly anticipated the need to shave my penis, testicles, and anus.

His penis was notably vascular, with a glans that was generously sized, akin to a doorknob. It was not grotesque, but rather proportionate to his slender, soda-can-sized shaft. His fully formed testicles bobbed like buoys in the water's current directly above me as I navigated between his legs, lifting my shoulders to meet his buttocks, with his rectum positioned near the nape of my neck. I then encircled his lower legs and lifted him out of the water.

As the water cascaded from our bodies, I turned my head sideways, and there it was—his divine penis, resting against my jawline. This was the closest proximity I had ever experienced to another man's penis, but contrary to my anticipated reaction, I felt no inclination to withdraw. The shaft of his penis felt substantial and yielding against my neck and chin.

I quickly turned back, and in the process, my lips brushed against the ample head of his penis. I felt as though barriers were being crossed at an unmanageable speed. This close proximity to Dylan's aesthetically pleasing male anatomy, and the accidental contact with his glans, did nothing to quell the burgeoning hardness of my own penis. Quite the contrary, in fact.

Blood surged throughout my body, and despite being in the pool, I felt a sensation of intense heat. This sensation was particularly concentrated in my penis, and I could feel its head breaking the surface of the water. To deflect attention from my erection, I immediately engaged in vigorous wrestling with the opposing team.

As we engaged in laughter and playful grappling, I deliberately overexerted myself, attempting to redirect blood flow to my arms and legs and away from my penis. We tumbled sideways, and Dylan shifted, landing around my neck and sliding off my shoulders, his ankles now resting upon my trapezius muscles. He was floating on his back, facing me. More significantly, his previously relaxed soda-can-sized penis was transforming into a dense cluster of spaghetti-like form, complete with all the accompanying ridges and structural elements.

"We make a good team," he remarked, observing my penis head swaying above the water's surface like a periscope. I informed Dylan and the other two gentlemen, Phillip and Ray, that I needed to exit the water to use the restroom. Clutching a beach towel to my crotch to conceal my fully erect penis, I made my way to the house.

The residence was exceptionally luxurious, and I located the master bathroom. The house was owned by a gay couple, both physicians, who clearly possessed impeccable taste. The master bed was a vast expanse of silky smooth black satin sheets, a matching comforter, and numerous pillows. I couldn't help but ponder the multitude of male anuses that had been penetrated and penises that had been orally pleasured upon that very bed. I envisioned a threesome of attractive men ejaculating into each other's orifices and mouths on that bed, their semen cascading like warm caramel sauce onto an ice cream cone, adorning those satin sheets.

I found myself envying gay men for their man-to-man romantic relationships, which they experienced without the perceived complications of heterosexual dynamics, as well as their apparent absence of sexual inhibitions. A profound questioning of my own sexual identity began to surface. "Were there subtle indications all along? Did my inherent curiosity and fascination with gay culture actually stem from a yearning to be a part of it?" I pondered.

Based on conventional perceptions, I considered myself a prime candidate for a stereotypical gay man, at least according to the profile Scott had previously outlined. I had majored in art during my university years. I worked within the fitness industry. I held a deep appreciation for male anatomy. Furthermore, I dedicated considerable effort to refining my own physique, aiming to present myself as the ultimate object of attraction for gay men. After all, most women were not particularly interested in the musculature of their heterosexual boyfriends and husbands. This moment presented a significant opportunity to genuinely assess my sexual identity.

I was reasonably confident that my physiological response to the pervasive male stimuli was an anomaly, and moreover, I was prepared to stake my reputation on this assumption. It would prove to be considerably embarrassing if, after being introduced at the outset of the party by Scott as his heterosexual friend—a detail he emphasized to each guest, seemingly out of concern that I might feel objectified—I were to suddenly become the guest most aroused by men, desirous of engaging in anal intercourse with one of them, or even more disconcertingly, to desire them to penetrate me.

I resolved to allow my physical responses to dictate my desires, believing that my conscious mind could be misled. I intended to re-enter the social scene, now that my erection had subsided and my body had relaxed, to ascertain if my hypothesis held true: that I could maintain a state of non-arousal throughout the remainder of my interactions at the gathering. I examined my reflection once more, taking in my alluring physique.

With the party now proceeding without swimwear, I stood entirely exposed for all to observe, my penis, testicles, and anus meticulously shaven, radiating virility and masculinity. I turned to examine my appearance from behind. It was, if I may say so myself, a rather handsome posterior. I bent over to inspect my anus. It appeared as a rosebud of skin folds leading into a veritable tunnel of pleasure. As I had previously admitted, I would readily engage in sexual activity with myself, were it physically possible.

The contemplation of my anal region prompted a realization: something was conspicuously absent from this personal challenge. I located a substantial container of sexual lubricant in the bathroom, scooped a generous quantity into my palm, and meticulously massaged it into my sphincter. Initially, my anal opening felt constricted, but upon inserting a finger, it began to dilate. I was already familiar with this physiological response from my prior explorations of my own posterior. Now, my awaiting anal canal was dilating and thoroughly lubricated. While not strictly necessary for my current intentions, it seemed only fair to present both sides of the argument concerning any potential latent homosexuality.

I made my way back toward the pool area, resolute in my intention to maintain a state of penile calmness and lack of excitement. Upon re-entering the outdoor space, I immediately encountered Ted once more. He offered a smile upon seeing me and inquired, "Where did you vanish to? I was concerned you might have departed." I instantly felt an urge to serve him again, so I retrieved a bottle of wine and two glasses and approached him.

"May I pour you a glass of wine?" I inquired. "Why do I sound like his attendant rather than his equal?" I questioned myself internally. I presented him with a glass of wine while my gaze remained fixed upon his physique, that captivating smile, and his penis. My testicles began to feel a distinct tightening, and my penis started to grow heavy. Uh-oh, the familiar sensation was returning. There would be no way to conceal an erection this time, nor any plausible explanation other than genuine sexual attraction to an attractive man!