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Gay Daddy Literotica

My Roommate: A Daddy's Transformation of Me

NOTICE:

Yet another commissioned piece!

Additionally, I have a futa commission currently in progress, and a subsequent one scheduled. I am gradually completing these projects and anticipate resuming my regular writing once they are done. After all, it is the holiday season, so financial necessity is certainly a factor.

This narrative explores themes of gay reluctance, unfolding between an older "Daddy" figure and a younger college student. Be advised, content includes coercion, resistance, and particularly intense sexual acts. In a sense, I am revisiting some of my earlier literary themes with this contribution.

It bears repeating that I neither endorse nor advocate for any form of non-consensual acts or reluctance in real-world scenarios. This is a work of erotic fiction and should under no circumstances influence personal conduct within the general public. "No" unequivocally signifies "no"; please, always respect the boundaries of others.

Anticipate further content in the near future.

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During my collegiate years, my existence underwent an unexpected shift.

My appellation is Liam. Having recently reached the age of twenty-one, I find myself in a somewhat precarious position at this juncture of my life. My height is approximately six feet. I possess a slender, well-defined physique; an appealing young man overall, with pleasant lips, vibrant green eyes, and refined facial contours. My hair, which reaches the mid-point of my neck, is slightly elongated, parted centrally, and exhibits a gentle wave.

Regarding my parents, I prefer not to elaborate extensively, but they are currently absent from my immediate circumstances. While both are alive, their deplorable character renders any prospect of cohabiting with them unfeasible. Given that senior year was drawing near, remaining employed at the campus food establishment for the remainder of my life was simply not an option.

Regrettably, I possessed virtually no clear direction; I had intended to pursue a degree in English, primarily because I lacked any foresight regarding my life's potential trajectory. A plan formulated with my friends to secure a shared dwelling utterly dissolved. Furthermore, with my parents on the verge of withdrawing financial support, it became imperative to secure alternative living arrangements before the dormitories initiated my eviction as the summer recess commenced.

My companions were also planning to be away, rendering the sweltering summer months particularly trying. I fully anticipated experiencing profound boredom. My sole activities were projected to consist of work, self-gratification, solitary perambulations, dining, and video gaming.

The assistant manager at my place of employment, a man named Jerry, was slightly shorter than me and appeared to be in his forties or perhaps fifties. He was certainly older than I. He presented as quite a hirsute individual; "doughy" would be a fitting descriptor, not obese, but possessing the typical physique of an older gentleman. A noticeable beer belly protruded beneath his uniform, his body was notably hairy, and his hairline was receding, among other characteristics.

One evening, Jerry and I found ourselves working alone during our shift; although he wasn't my preferred colleague, he considered me a friend and allowed me considerable latitude. The downside, however, was that Jerry was an exceedingly... opinionated... and boisterous person. Constant refrains of 'Your generation this...' and 'Your generation that...' perpetually assaulted my ears. His pronouncements were blunt and delivered without consideration, and often, should one attempt to challenge him, he would retort with a 'don't CANCEL me!' or an 'I know I'm not woke or whatever...'

Consequently, I endeavored to steer clear of political discussions whenever possible; this, however, did not deter him from engaging me in conversation constantly. He was undeniably more affable towards me than I was towards him. Occasionally, he would deliver a playful slap on my backside during work hours, typically when no one else was observing.

On that very same night, as Jerry exhaustively recounted tales of past generations' work ethic, the conversation inexplicably veered towards me confiding in him about my personal predicaments.

"Indeed... I'm genuinely uncertain about my next steps, man; I'll need to sort out a housing solution quite soon..." I muttered in resignation.

"Oh, truly? Tell me... I actually possess a vacant chamber within my two-bedroom dwelling. It proved sufficiently economical post-divorce, but with the current ascent in rental costs, I genuinely require a housemate."

"Oh... I'm not sure, Jerry, that's-"

"I comprehend, you're disinclined to share quarters with a man twice your age, eh? Fret not, my friend; though advanced in years, my touch remains undiminished. You need not concern yourself with escorting women home or similar matters; I shall remain entirely out of your way."

"Well, I appreciate that, but I don't wish to inconvenience you, and furthermore, my earnings here aren't exactly substantial. I'm uncertain if I can afford much in the way of rent these days."

"Ah, yes. Remuneration is quite challenging for undergraduates..."

He paused, appearing to be in deep contemplation.

I resumed the task of tallying the register, as our closing procedures were underway.

"You know what? How about you simply reside with me gratis while you regain your financial stability?"

"Whoa. Are you absolutely certain? What about your own rent?"

"I can still manage it, and besides, just look at you; you're incredibly slender, you'll probably occupy hardly any space in the kitchen."

"Well. Alright, I suppose that sounds agreeable. Thank you immensely; is there any way I might assist you around the domicile or with anything else? Should you require me to attend to dishes or cleaning, I would be more than pleased to relieve you of those tasks."

"That proposition sounds quite favorable to me; observing you performing all the 'women's duties' around the premises strikes me as a spectacle I would rather enjoy. Perhaps we should even attire you in a maid's uniform while we're at it!" He chuckled to himself with relish.

"Haha..." I emitted an awkward laugh, "Yes, that would indeed be humorous..."

"I wager that would truly suit you well. I'm aware of your generation's fondness for wearing dresses; I frequently observe it on TikTok. While I typically refrain from judgment, what precisely is the impetus behind that trend?"

"I have no idea. I personally never engaged in that practice; I believe it was merely something Harry Styles initiated that gained widespread popularity."

"Honestly, I can barely distinguish you young men from young women anymore; I'm quite perplexed as to what transpired that led you all to shed your chest hair!" He laughed once more, delivered a firm slap to my posterior, then departed towards the rear area.

Good heavens, I anticipated a considerable amount of that once I moved in, didn't I? I suppose I had little alternative...

----

Over the ensuing months, Jerry interpreted my consent to cohabit with him as confirmation of a bond as intimate as his own feelings toward me. The professional advantages derived from this arrangement were considerable, yet it concurrently brought about an increase in unsolicited posterior slaps and a greater volume of uncomfortable conversations.

His discourse invariably gravitated towards subjects related to my physique. Initially, the remarks were mild, pertaining to my leanness, but they progressively grew more peculiar. He would comment on my hips being slender and 'feminine,' or how my posterior was unduly firm for a male, even suggesting that with a wig, I could likely be mistaken for a woman. Each instance was met with a somewhat nervous laugh on my part. Jerry presented as unequivocally heterosexual, so his comments did not unduly vex me, considering the routinely offensive nature of his utterances.

----

The day for relocation finally arrived; Jerry assisted me with the meager possessions I owned. Given my collegiate status, packing lightly was effortless, and he had already prepared a bed within my designated room, leaving virtually no strenuous lifting required.

That same evening, we shared a few beers and engaged in some light conversation. It was surprisingly pleasant to gain a deeper insight into him. The sole annoyance was his tendency to place his hands on me at arbitrary moments, often squeezing my thigh or shoulder. Even as he grew slightly intoxicated, he began to gently rub my back at brief intervals.

Despite these observations, he had imparted some details regarding his life: his birthplace, his upbringing, and the dissolution of his marriage. These revelations were interspersed with rather antiquated political perspectives, yet nothing beyond what one might expect from a typical baby boomer.

We retired to our separate sleeping quarters that night and proceeded with our lives.

Overall, Jerry proved to be a satisfactory housemate; he generally afforded me privacy and space.

My primary annoyances stemmed from his utter disregard for cleanliness concerning dishes, thus increasing my workload, and his frequent habit of ambulating either pantless or shirtless, exposing his hirsute abdomen to my view.

For approximately one month, the situation remained quite tolerable, largely consistent with Jerry's behavior prior to our cohabitation. That equilibrium persisted until one particular night...

I was engaged in washing the dishes when he re-entered the space, once again shirtless. He had consumed several beers that evening and was in the process of acquiring another.

"Greetings, my friend," he uttered, brushing past me to access the refrigerator in the kitchenette.

"Hello."

He accessed the refrigerator, retrieved an ale, uncapped it, and took a substantial gulp. Rather than departing, he merely lingered, observing me for a fleeting moment.

Within my peripheral vision, I could discern him consuming his beer, his gaze intensely fixed upon my side.

I glanced over, raising an eyebrow in inquiry, to find him scrutinizing me from head to toe.

"Is everything satisfactory, Jerry?"

"Indeed. You simply appear quite natural while performing that, do you not?"

"No. What do you mean by that?"

"I am aware that I frequently mention it, son, but by thunder, you appear splendid while washing dishes."

"Oh... thank you, Jerry?"

"Don't give it another thought."

He persisted in his scrutiny as I reverted to my dishwashing task.

"...You're not homosexual, are you?"

"Uh. No? Not to my knowledge, at least."

"Are you certain? You possess the physique of one. I'd wager men would adore you, given your appearance."

"Uhm, yes, perhaps, but I am heterosexual, so I haven't particularly exerted myself to investigate that aspect."

"Yes. I am as well."

Abruptly, he set his beer aside and approached from behind me.

My hands ceased their movement as I perceived his hands beginning to stroke my sides, rubbing my waist in an upward and downward motion.

"Damn," he murmured, "If I were less discerning... ensure you avoid wearing a wig; who knows what I might be compelled to do..."

I sensed his denim trousers pressing against my buttocks, grinding against my rear with an awkward friction.

In a state of stupefaction, I became motionless, utterly bewildered by the unfolding situation.

"Your hips are truly exquisite, son..."

His fingers now firmly gripped my waist, immobilizing me as he slowly swayed against my trousers.

This peculiar interaction persisted for a full half-minute before I finally vocalized my discomfort, my face flushed with embarrassment.

"Alright, Jerry, this is becoming strange now," I stated unequivocally.

He halted, withdrawing slightly from me.

"Ah, you know I'm merely jesting, friend! I became somewhat carried away on this occasion, my apologies..." He stated, departing the room, "Have a pleasant evening!"

"Y-yes... you as well..." I hesitated briefly... then resumed my cleaning.

-----

Matters did not escalate significantly in terms of bizarreness thereafter, though the threshold for what constituted "weird" had by then fallen quite low. Playful slaps on the backside gradually transformed into definite grabs, causing me to flinch, which he found amusing. Shoulder massages, though brief in duration, occurred with increased frequency. Remarks concerning my perceived charm and feminine qualities became more prevalent than before.

Then, the entire dynamic unequivocally shifted one particular night. That night, he became audacious.

Upon my return home from a work shift, I observed him on the sofa, his shirt removed. He was engrossed in watching conventional television, yet a distinctly familiar aroma permeated the air.

I detected the scent of cannabis, which was both pungent and intoxicating. Subsequently, my gaze fell upon the joint clasped between his fingers.

He noticed my awareness of both him and the marijuana.

"Hello, friend! Welcome home; I trust you don't object. I merely sought a bit of relaxation."

"Oh, no problem at all, Jerry, you're perfectly fine."

"By Jove, you appear utterly fatigued. Was it a particularly lengthy shift?"

I had thought I appeared decent...

"Honestly, it was the same as usual, but I suppose I am feeling a touch weary."

"Under normal circumstances, I don't favor college-aged males smoking illicit substances, as it often leads to foolish conduct, but I believe you've earned a respite, pal. Remove that uniform and share this with me; unwind for a while, and we can watch a film or something."

I paused, feeling a distinct pull of temptation.

"You know what... yes, certainly, Jerry, why not."

"That's my boy! Join me whenever you are prepared."

"Will do."

I retreated to my chamber, experiencing a brief moment of relief as I changed into a pair of loose-fitting shorts and an unadorned white shirt.

I emerged and settled beside him.

He extended the joint to me, and I inhaled deeply. A warmth suffused my lungs as I exhaled.

"By George, you're no stranger to that, are you?"

"I mean, everyone engages in smoking during college, don't they?"

"I certainly did, to be sure. I abstained for a period, but subsequent to my divorce, I resumed the habit," he stated, reclaiming the joint.

"Goodness, this is potent, Jerry," I remarked, already perceiving a relaxation in my shoulders.

"Indeed, I know. It's quality material. I acquire it from a fellow on your campus who cultivates it with his associates."

"Truly? I had presumed you would prefer minimal interaction with my generation."

"Make no mistake, your cohort possesses little understanding of true masculinity, yet... by golly, you certainly comprehend how to revel."

I chuckled faintly at that remark, accepting the joint back and taking another draw before permitting him to finish the remainder.

The film projected on the screen immediately became more engaging as we both sat in comfortable silence for a time.

Abruptly, a risqué intimate scene materialized; the protagonist and the alluring love interest finally engaged in sexual congress after an extended period of palpable tension.

Jerry let out a whoop as she divested herself of her brassiere, then plunged atop the main character as they both became entangled in a carnal embrace.

"That young man is truly fortunate!"

"Yes. She possesses a pleasing countenance," I commented with an air of nonchalance.

"Have you ever engaged intimately with a woman of such striking attractiveness?"

"Not as of yet; I am endeavoring to, but I am somewhat preoccupied. You know, with employment and all."

"You are excessively diligent! When was the last occasion you experienced sexual intimacy, pray tell?"

"It has certainly been a while."

"All you seem to do these days is work, son. Allocate a modest period for your personal gratification from time to time!"

"I attempt to, when circumstances permit. I do not observe you engaging in any amorous pursuits, however," I jested.

"Ha! You are correct in that assessment. I haven't been with anyone since my wife. Even then, the sexual encounters at that juncture were quite dreadful."

"Yes. I suppose such things transpire."

"Well, what is your justification, eh, handsome fellow? You cannot possibly dedicate your entire twenties to labor; you must become more receptive and explore novel experiences, must you not? That is, after all, the essence of youth."

"I mean, I will, eventually. I merely wish to stabilize my life first."

"You know, Liam, you are truly one of the commendable ones. In comparison to other individuals within your peer group, you exhibit diligence and self-care. I genuinely admire that about you. However, it is just us here. Be forthright with me..."

"Alright? And I thank you for that, by the way."

"No trouble at all... when was the last time you indulged in self-pleasure? You consistently appear stressed, and I surmise you are not affording yourself adequate time to truly unwind these days."

"I simply wish to avoid becoming addicted to pornography; I still engage in it occasionally."

"Such as when?"

"Uh..."

"It is just us, son. It is not as if I intend to disclose to everyone the last time you masturbated. It is scarcely a source of embarrassment."

"I mean, a couple of weeks ago, I suppose..."

"A mere fortnight?! Oh, good heavens, young man, it's no wonder you perpetually appear so downcast."

"It is truly acceptable; I can manage without it."

"Well. You are assuredly more resilient than I. Ever since I've been living alone, I engage in it at least three times each day."

"When do you find the leisure for that?"

"I engage in it frequently in the workplace lavatory."

"Ah. So that elucidates your consistently prolonged breaks."

"You've discerned correctly; it genuinely provides me with considerable relief, however. You, conversely, ought to be masturbating more frequently! That accumulated stress will be your undoing."

"I mean... alright, Jerry. I will attend to it this evening before I retire to bed."

"Confound it, why not now?"

What words had just escaped his lips?

"What?... The motion picture is still playing."

"Indeed, and you just remarked on that woman's attractiveness. Proceed. Expose it right here."

I emitted an awkward chuckle, then paused, the realization dawning that he was in no way jesting.

"Here?" I lifted an eyebrow in question, "I mean, do you intend to vacate the room?"

"Well. Perhaps I, too, wish to alleviate some of my own tension. I am already experiencing an erection merely contemplating her; I wager you are as well."

"Uhm... yes, I'm not so sure about that, Jerry. I will attend to it later." (This was an attempt to passively steer the conversation to a close.)

I was too profoundly intoxicated to truly discern the underlying motivations behind his proposition. Or perhaps I simply preferred not to contemplate them.

I heard him emit a sigh, then rise to his feet.

Before I fully comprehended his actions, I heard the sound of his zipper descending and his penis flopping forth!

"WHOA!" I recoiled, turning away, "Jerry! Conceal your phallus!"

"Observe it. Come now."

"Jerry, seriously, what in heaven's name are you doing?"

"Just cast your gaze upon it for a moment. I shall retract it after you have looked."

I scoffed and afforded it a swift glance. That brief glimpse escalated into an expression of profound astonishment.

He was indeed remarkably well-endowed.

His penis, though flaccid, measured approximately six inches. It was also, in a certain sense, unappealing, reeking intensely of masculinity. The sleek, leathery shaft protruded from a dense cluster of pubic hair, dangling like the appendage of a small elephant.

I found myself unable to avert my gaze, openly gawking at it for a considerable duration while he stood there in silence.

"You see? It's merely a phallus, young man. It's not as though I am homosexual or anything of the sort. I am aware that you are not either. So, let us simply achieve gratification together," he articulated with an unsettling gentleness.

"Uh... uh, Jerry, I don't..."

"Here."

He retrieved the remote control from the table, his penis still exposed, as he stood merely a few feet distant.

Instantaneously, the television blared with explicit pornography. A female voice shrieked in sexual ecstasy as she was vigorously penetrated by a man whose face remained obscured.

Everything was transpiring with bewildering rapidity.

"The film was growing tedious anyway; now you have something compelling to observe."

"Jerry, I... I don't believe..."

"Simply expose your cock. Do not concern yourself, my friend; do not render the situation awkward. I merely intend to assist you quite swiftly."

I was so profoundly intoxicated and disoriented, and he appeared to be equally so; I had never witnessed this aspect of his character surface. He was remarkably gentle, yet entirely direct. I was on the verge of exposing my penis; he offered no discernible alternative.

Stuttering, bewildered, and feeling as though my own physique was operating autonomously, I began to lower my shorts slightly.

"There we go. You see? Not so formidable."

My penis was already responding, becoming engorged. My average-sized member appeared diminutive in comparison to his. It was also smooth and devoid of hair.

"Damn, young man, even your cock possesses feminine qualities," he chuckled, "Do not be concerned, friend; it is not a contest. We are both merely relieving some accumulated tension."

He settled down directly beside me. His arm extended over my shoulders, drawing me into close proximity as his hirsute torso rubbed against my side. The coarse hairs and his warm body instantly put me on edge. My penis immediately receded as he continued to rub against me.

"Proceed, friend. Begin to masturbate. You require this, come on, boy," he prodded me. His tone was both patronizing and instructional.

I found myself unable to do anything but sit there, stammering silently. Was I truly on the verge of performing this act? My overstimulated mind plunged me into a state of utter paralysis as this unfamiliar man, twice my age, instructed me to masturbate in his presence.

"Hey, don't be apprehensive. Allow me to assist you, buddy."

Suddenly, his unoccupied hand extended forward and enveloped my soft penis!

"Uh! Whoa!" I gasped.

"Relax, young man. Simply imagine it is that woman visible on the screen."

His free hand then moved to adjust my line of sight towards the explosive pornography unfolding on the screen.

As I witnessed the woman bellowing in pleasure while being utterly overwhelmed, my penis began to reawaken. Particularly due to this hand job; by holy hell, he was skilled. His hands possessed a perfect smoothness, and he was stimulating me with remarkable precision. His grip was not constricting around my penis, but rather loose and gentle, feather-light in its touch as his wrist maintained a steady, rhythmic motion.

Pre-ejaculate had already begun to seep from my tip as he deftly wiped it away with his palm and utilized it as a lubricant.

"Ouhh..." I moaned, utterly incapable of denying the pleasure he was imparting to me.

"Yes," he exhaled, "Just continue, friend; do not even give it a thought... no one will ever know..."

I attempted to clench my jaw, striving to reclaim some semblance of composure, but the pornography blared in my ears, and his touch felt so incredibly, profoundly good!

The manner in which his hand glided across the skin of my shaft, stimulating me with such remarkable efficacy. He had, without doubt, performed this act before. And unequivocally not upon himself, either...

This hairy man was delivering the finest handjob of my entire existence; what in the name of Hades was transpiring?! I was unable to reach climax because Jerry was pleasuring me! Jerry from my workplace?! The very same Jerry?!

"Ouh. Damn," I unconsciously groaned, still observing the pornography but sensing Jerry's respiration growing more labored.

Jerry's own penis was becoming erect, stimulated by my reaction to his extraordinarily skillful technique.

I could literally perceive its ascent in my peripheral vision.

As I cast my gaze downwards, I found myself compelled to fully turn and observe it in its complete robustness. The uncircumcised foreskin receded to reveal an inflamed red glans, with veins visibly throbbing across its shaft. It was nearly as thick as my forearm, seeping pre-ejaculate from its apex. Hot and musky, its pungent aroma reached me even from that distance, the distinct tang entering my nostrils.

My eyes widened as I beheld it, flicking hypnotically between his legs.

"Heh. I surmised you harbored a slight inclination towards homosexuality. You and your generation cannot help but admire a genuine man, can you?"

I abruptly snapped out of my trance, directing my gaze squarely at his ravenous face, mere inches from mine.

"W-w-what? No, I was, it's just-"

"It's quite alright, young man. I shall not divulge this to anyone. It will remain our confidential understanding," he exhaled. "I am aware that I possess a substantial one. I wager it's difficult not to look. Here, since your curiosity is piqued."

His right hand disengaged from my shoulder, and he shifted his position to face me. I found myself unable to stop looking at his penis, which was now pointed directly at me. The explicit video continued to blare in the background.

With his free hand, while his other continued its rapid up-and-down motion on my secreting dick, he began to slowly masturbate himself as well. As a thick, saline globule of warm pre-ejaculate erupted from the top, he harshly drew his hand upwards and rotated his thick thumb around his tip, collecting the fluid on the very end of his digit. His thumb became coated in a hot, viscous layer of his own precum.