Holiday

Obsession du Jour: 24

by Holiday on 07/23/2025

in erotica

Lately, I have acted like an incorrigible slut and abandoned myself to debauched behavior with a half-dozen strange men.

The other day, at mid-morning, I headed for the train station and was in the Shinjuku neighborhood of Tokyo within 80 minutes. Like moth-to-flame, I walked south along Shinjuku-Doro, turned left at a now familiar Western-styled restaurant, and proceeded immediately to 24 Kaikan. This time, I remained in the gay sauna all afternoon.

For an early weekend afternoon, there were plenty of clients, and so I cruised the two main floors to appraise the usual perversity and capitalize on any opportunity. Yet for at least the first hour, nothing happened in my favor. On the fourth floor, in the unlit connecting rooms of bunk beds and ground-level mattresses, there were the usual sounds of a man slurping cock, a man pounding ass – and the accompanying moans of both approval and outright ecstasy. Some sounds are universal and transcend language barriers straight away.

I returned to the Mist Room, my favored locale on the third floor, a place where men pop in-and-out constantly, as if disappointed that someone else has staked out the territory. The unasked questions are always who is going to top, and who is going to bottom?

This time, when I entered the room, a younger Japanese male was present in a skimpy towel around his waist, already in reclining posture opposite the seating area. I knew what he wanted. When I sat across from him and he didn’t move away, I knew what was going to happen next. He touched me with his left leg to beckon me toward him. To underscore his intent, he removed his towel and exposed his hard cock. He was very well endowed – perhaps seven inches, and it was shameless how quickly I succumbed. I went down on him with pleasure. When a scene starts other men enter the room, like a scent drifted under the doorway luring the curious and the depraved. One man stayed and jerked off.

Although I worked my lips lavishly over my candidate’s cock, he really wanted me to kiss and lick his balls while he jerked off. So, I did, as he motioned for me to alternately switch and focus on his cock – as he virtually jerked off. After initially spurting hot cum into my mouth, he pulled his cock away and fully climaxed on his abdomen. He seemed happy. The third party, standing next to us with his throbbing cock, had hopes that I would suck him off next. He was tempting, in a second choice sort of way, but I needed a break. Besides, I didn’t want to be the object of an oral gang-bang.

I retired briefly to a shower, then relaxed in the heated sauna and watched readily as fit, younger Japanese men – many in their 20s and 30s, sat on the stools with their backs to me and bathed themselves. I had to admit this was sensual, and more appealing than I ever imagined.

Later, I adjourned to the communal bedroom on the fourth floor and watched a rough-and-ready American biker-type fuck a younger, slender Japanese twink on a floor-level mattress. The bald American was on his back, with the long-haired Japanese straddling him, impaled on his cock. The bad boy biker used his large hands to maneuver the pretty twink up-and-down on his hard shaft.

Continued …

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A Life of Gilded Aimlessness

by Holiday on 07/18/2025

in claytonholiday

Because I am a passionate belletrist who often prefers the company of books to people, I routinely look at the titles as if evaluating the rare treasures of a scriptorium. The attraction for this asceticism began at an early age, though certainly by 16, when I was introduced to the writings of the Marquis de Sade, Rimbaud and Huysmans, three eminent degenerates.

Based on this initiation, I gladly embraced drink, dissipation and decadence. For years, I permitted myself to be in thrall to unsuitable persons as long as my proclivities were easily gratified. A life of gilded aimlessness defined me perfectly.

A recent role model was the charismatic Yoshi Kawamura, one-time luminary of Tokyo’s sadomasochistic scene. The incomparable roué inspired a private party I hosted for Mrs. Evans, my married British lover. What marked the occasion? It was time to celebrate two months of delicious hedonism, though any excuse was valid.

I’ve always enjoyed an irresistible cocktail of voyeurism and infidelity. Yet it’s not enough to simply misbehave; a certain intense edginess naturally enhances life. For instance, I ordered Mrs. Evans to appear at my apartment near Yebisu Garden Place by 9 p.m., wearing only a Bedford leather mid-thigh car coat and a pair of black satin d’Orsay four-inch stiletto sandals with double crossing ankle-straps.

My lover demonstrated good grace, didn’t ask sassy questions, and only exposed her impeccable ass once or twice to pedestrians as she maneuvered brazenly in-and-out of her taxi. A classic MILF, Mrs. Evans looked sensational for age 40.

After ascending by elevator to my sixth floor apartment, the connoisseur of cock obediently handed me her leather car coat. I kissed Mrs. Evans passionately, and nodded toward an overstuff chair by two windows offering splendid views of the splashy Tokyo nightscape. She acquiesced with her cool, carefree style and sat down, wearing only her fashionable shoes.

With a never diminishing arousal, I readily watched two masculine Japanese rent-boys alternate between filling her pretty mouth with firm cock and stimulating her excited clitoris, while numerous condoms lay ready for use in a Versace ashtray nearby. Mrs. Evans was impossibly sexy.

Continued …

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24 Kaikan

by Holiday on 07/14/2025

in claytonholiday

Typhoon Man-yi hit Okinawa Friday, and may cross Tokyo Bay early Sunday. Many people here stocked up on basic supplies for the impending storm. I reacted to this news by cruising a gay sauna late yesterday afternoon in Shinjuku.

Known as 24 Kaikan, the sauna is in a low-key neighborhood, not far from Takashimaya Times Square, on the east side of the Shinjuku Station in Tokyo, the nation’s busiest commuter station.

My sense of direction in any Tokyo neighborhood is not keen, so I was easily lost. Yet I was sensible and asked a policeman for directions to the gay sauna; not something I’d ever consider in the U.S. Regardless of language barriers, Japanese officials like policemen and train conductors are culturally bound to be of service.

“First traffic light, go right,” the young policeman said, in that quaint, broken-English which can never quite pronounce the letter l. “Next traffic light, go right. Very famous place.”

On my way, I passed the modest Shinjuku Park, where gaijin prostitutes – typically Korean and Filipinos, tried to score with weak-willed salarymen on their way to the after hour bars; and low-life drug dealers offered an overpriced escape for males not interested in Asian pussy. Two policemen stood nearby as symbols of propriety, yet they did nothing to spoil these scenes.

A block away, I found 24 Kaikan, with the entrance on the second floor of a seven story red brick building. Like anywhere in the Far East, one must remove shoes upon entrance to a private setting, even a male whorehouse. In contrast to this classy etiquette, there were vivid posters on the walls of the lobby, depicting attractive young cum-guzzlers, sucking the thick, swollen cocks of slightly older, butch Japanese men.

Continued …

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Slouching towards Babylon

by Holiday on 07/10/2025

in sex

I wonder how many of us would go down to the crossroads and elect for a life of breathtaking experience and misery rather than mediocrity and comfort.

According to the closeted E.M. Forster, “most of life is so dull that there is nothing to be said about it, and those who talk about it as interesting are obliged to exaggerate, in hopes of justifying their own existence.”

Yet, if you’re an obsessive like me, there is a certain glorious insanity to the roller-coaster of emotions required to make each day worthwhile.

For instance, when I married, I didn’t realize my wife was congenitally unfaithful; it turned out she was omnivorous in her desire to experience the full range of cock. This made life far from ordinary and settled as I traversed the extremes of splendor and strangeness.

Why didn’t I leave my wife? Chief among reasons, I loved her – hopelessly. And, of course, this lewd delinquency actually fueled my desire for her. I was nothing less than an addict who always carved one more fix. My wife knew this and turned up the volume repeatedly.

Aside from being openly cucked, what tormented me more exquisitely was that her boytoys were drawn from among the jeunesse dorée. My 38-year-old wife happily abandoned herself to these transient lovers with enticing blow jobs and precise vaginal expertise.

One specific 24-year-old Eurotrash she fucked in a sleazy seaside motel really sent me off the rails. Although I usually affected an air of world-weary decadence and conveyed a self-conscious passion for Joris-Karl Huysmans, I could also be petulant about my wife’s promiscuity. The fact that her newest lover was half my age distressed me a little.

“Enough with the kvetching, already,” she scolded. “Just because he has a wonderfully thick cock doesn’t mean I’m going to leave you. Stop being such a size queen. Don’t forget, I love you.”

Inflamed because my wife behaved wantonly for a much younger man, I obsessed about how easily he filled her mouth with hot cum.

“Go ahead and kiss me,” she invited. “You know the young man forced me to my knees and made me suck his beautiful cock.”
“Yes, I know.”
“You also know that I pleased him in every way.”
“Why do you give yourself to other men?”

My wife put her arms around my neck and kissed me tenderly. The fresh fragrance of her lover’s spent cock overwhelmed her breath.

“You know why I fuck other men,” she said nonchalantly.
“No, tell me, again.”

Continued …

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Slut without Apology

by Holiday on 07/07/2025

in sex

I admire people who peel the world with their fingers, like a glowing orange dripping juice. Imagine my delight when Mrs. Evans performed a seductive dance for me to Lou Reed’s ode to sado-masochism.

“Won’t you please treat me like a slut?” my married lover asked, after discarding all clothing.

I mentally fondled the question for a second.

“Yes,” I said, and quickly abandoned my dark blue suit jacket and removed my leather belt.

The inimitable, 40-something British expatriate always made me aroused, regardless of her state of dress. The full-figured brunette had great legs and exuded sex appeal and unpredictability. To me, she was a beauty but I was initially smitten when I talked to her. She possessed an inventive and disordered brilliance that never turned on itself.

I met Mrs. Evans a few months ago at a Tokyo gallery opening on the chic Omotesando Dori, a road in Harajuku often compared to the Champs-Élysées. It was early that evening when I watched her husband plant a platonic kiss on her cheek. “I love you,” he said with the enthusiasm of a departures announcer at Heathrow airport.

As a fugitive from boredom, I knew Mrs. Evans was weary of respectability and welcomed some classy debauchery. Who wants to go through life in marital dishonesty with a scholarly subspecialty in Anais Nin?

My paramour’s wealthy husband was notoriously and fantastically unpleasant. With a heedless wit dipped in vitriol, the porcine man just plain sucked the air out of any party. Considered by many to be a filthy shitweasel, he was often reduced to adolescent self-pity and rapt, neurotic jabber.

At the end of day, after a heroic consumption of whiskey, this fatuous character wheezed on the leather sofa of their ritzy third-floor Hiroo apartment in Shibuya-ku, while zebras leaped across the TV screen.

In Mrs. Evan’s company, my raison d’etre was to excavate the decadent soul that lurked beneath a decorous facade. Her husband made love to her, but I fucked her.

Our private time together was rationed carefully; we wanted to countermand the ennui beyond our closed society. To help set the tone, we listened to jazz from the golden age of brothel music. Her husband had an extensive collection.

“You like it dirty,” I said, as I squeezed her taut nipples.

“Stop teasing,” she said, “and fuck me.”

“You know what must be done first.”

“Yes.”

So my married lover dropped to her knees obediently and performed fellatio before a large exposed window. The chaotic cityscape of Tokyo was compelling; besides, I wanted other degenerates to enjoy our spectacle.

Whether writing, falling in love, or pursuing furtive sex, I like doing it with intensity because I’m always looking for the next hit.

Continued …

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