Sissy Stories: Sissy and the Couple’s Chastity Journey

February 1, 2024

This story is intended for arousal, and I hope it triggers a satisfying response. If you find any of the following offensive, it’s advised not to read further: “Bi sex, Gay sex, eating cum, worshipping cock, anal sex, humiliation, gang bangs, masturbation, faggots, docking, femdom, sissys, bottoms.” For those remaining, sit back, relax, and lower your pants. I trust you’ll enjoy the adventure; I certainly did writing it. Feel free to comment; I get turned on too.

I identify as a size queen, an anal male princess with a bruised throat and a well-used asshole. I revel in slobbering over a hard cock, especially those of alpha males with large, throbbing members and balls full of juice that I eagerly drain.

I embrace my identity as a submissive individual, a sissy faggot perpetually craving cum. Degrade me, spank my ass, make me gag and choke. Slap my face with your manhood, smear your pre-cum across my lips.

Allow me to worship your cock and ensure your balls are emptied of all your essence, either through my slutty mouth and tongue or my insatiably talented asshole, ready to coax every drop of cum from you.

Exploring the Obedience to Chastity Tour

Let me share how I found myself in this situation, moving in with a married couple, “Kim and Dave,” when I was 18, and they were both in their late 30s.

It all began one morning in the kitchen. Kim strolled in, clad in a G-string and a sexy teddy. My arousal was instant, given my age of 18 and limited experiences. Horny and eager, I’d do anything to be intimate with her—and I did.

Kim wasted no time. Approaching me, she took hold of my now-leaking arousal. With her big blue eyes, she asked if I’d like a blowjob. My enthusiastic “Yes, please, please” led to me standing up, lowering my shorts, all while she maintained her firm grip on my shaft.

Calling out to Dave, who entered wearing only a red jockstrap, Kim swiftly had my arousal in his mouth. Initially protesting, thinking Kim was meant to provide the service, I succumbed to the expert pleasure Dave was delivering. Kim explained the deal—I would receive oral pleasure, but first, I had to reciprocate with Dave and swallow his essence.

At her words, I released one of the most substantial loads of my life down his throat, but Dave kept going. Weak-kneed, he maintained a firm lock on my throbbing arousal. A second torrent of satisfaction followed, and Dave let my well-satisfied arousal slip from his mouth, diligently cleaning it along with my balls and asshole.

Afterward, Dave thanked me politely for the encounter and proposed if I’d like to reciprocate. With him still hard and a trace of my essence on his upper lip, I invited both of them to my room.

Unveiling Desires

As I ascended the stairs, a hand gripped my ass, and a finger teased my asshole. Turning, I met Kim’s wicked grin. I pondered the fact that I had just moved into these people’s home, and now, two days later, I found myself in bed with both of them.

Prepared to engage in my first blowjob and having already participated in my initial gay encounter by letting Dave pleasure me, we entered the bedroom—all of us unclothed. My gaze fell on Dave’s cock, and to my surprise, it was adorned with a cock cage, and a substantial butt-plug was firmly in place.

Dave expressed gratitude for the delightful loads I had provided him. In exchange for letting him perform oral acts on me a few times a week, they offered me free accommodation. Kim sweetened the deal, promising a fantasy of my desire every time I engaged with Dave intimately.

This is why I find myself in this promiscuous situation now. Kim unlocked Dave’s cock, which, I later learned, had been confined for a month. As it swelled, I took it in my hand—larger than mine, and the first thing that struck me was the beauty of its head, vibrant purple and plump.

My first taste of cock became irresistible. As my lips slid up and down his shaft, my eyes rolled back in ecstasy. Twisting my tongue around the cock head, I realized right then that I loved giving head.

An Intimate Exploration Unfolds

If his cum tastes anything like mine, I’m going to be in love. The moment I began sucking on the head of his cock, it started leaking pre-cum, akin to a baby nursing a bottle.

I delved into the act, teasing Dave by bringing him to the edge and stopping, repeating the process over and over. Each time, I savored a bit of spunk, expertly milking it like a fervent cum enthusiast. I’ve extracted pleasure from mine many times.

As I immersed myself, I felt a hand on my balls, and suddenly, a finger found its way into my ass. Gagging on Dave’s cock heightened his arousal, intensifying his thrusts into my throat. This was my first encounter with anything in my ass.

Except for one instance when, in youthful curiosity, I greased up my mother’s hairbrush and inserted it about two inches into my asshole. The more Kim wiggled her two fingers in my ass, the more pleasurable it became.

Moaning with pleasure, Dave became more excited and delivered a 30-day load of cum into my mouth. I swallowed the first three substantial squirts, but the fourth and fifth shot sprayed across my face and lips.

My own cock began jumping, and to my surprise, cum started flowing out like a stream. Cum was everywhere; everyone had experienced ecstasy, except Kim.

Beyond Chastity Limits

As she divulged her desire to witness her husband penetrating my youthful rear, she maintained two fingers inside me. Adding a third, I emitted a loud moan, unaware that she had applied some anal-ease on that digit. I noticed a welcomed loosening, finding myself actively responding to her touch. My thoughts spun – meeting these people for the first time, and here I was, caught in an act that felt simultaneously violating and strangely enjoyable.

Head spinning, I observed Dave approaching with his 8.5″ cock. Kim withdrew her fingers, making way for Dave’s entry. Slowly, he inched into my eager cavity, the sound of our colliding balls resonating. Cum began seeping out, and Dave intensified his thrusts. In the corner, Kim engaged in self-pleasure with a sizable dildo, urging Dave to go harder. After about three minutes, he filled my ass with his essence.

Kim unleashed a primal groan, succumbing to uncontrollable orgasms. Witnessing her convulsing legs, she appeared possessed by ecstasy. When we all regained our senses, smiles adorned everyone’s face.

Become a Submissive Sissy

Kim asked if I wanted to continue living here. I eagerly nodded, and she tore up the lease, handing me a new one to sign. Before I did, she shared something crucial about her and Dave.

Firstly, she emphasized that she is the boss, a fact never to be forgotten. Secondly, she revealed her penchant for watching two men engage in gay and perverse activities. Thirdly, her husband was on the hunt for a submissive sissy wife—one willing to partake in any gay act with him, whether it be lazing around all day in a 69 position or engaging in explicit acts for small groups of the LGBTQ+ community.

Fourthly, she made it clear that when at home, my body belonged to both Dave and her. Finally, the fifth rule stated that sluts do not spit out cum, asserting that one’s sexuality is rooted in their asshole.

She then laid the lease on the table, accompanied by a cock cage, and looked up at me with a wink. I signed the lease, and she proceeded to lock my cock up. That marked the beginning of our journey as roommates, a bond that has endured for over a decade.

I take pride in being a submissive sissy slut, aiming to be the best sissy, cock-loving, sub, bottom, and cum-loving anal whore I can be.

Sensual Adventures in Chastity

All three of us share a deep connection. Dave and I engage in passionate acts, exploring pleasure through mutual satisfaction. Our collection of toys provides ample choices for our intimate escapades. One of my favorite indulgences involves the sex swing, where Dave brings his gay bar friends home for a night of unforgettable group encounters.

As Kim observes, she pleasures herself with a dildo in her pussy and a butt plug in her ass. After each man ejaculates, they hand their used condoms to Kim. Tying the ends to prevent leaks, that night she collected a total of 9 loads for me. Once everyone departs, Kim and I engage in the intimate act of snowballing, savoring every drop until it’s all swallowed.

Kim shares my fetish for the taste of cum, adding an extra layer of excitement to our encounters. Spending time with Kim is always anticipated, even though our intimate connection has mainly involved around two dozen instances of passion in the span of 10 years. She takes pleasure in witnessing men perform explicit acts on each other, while Dave engages with her about three times a week. On those nights, I take charge, responsible for arousing Dave’s cock and wetting Kim’s eager pussy.

Intimate Bondage and Pleasure

The allure of Kim’s essence on Dave’s cock is undeniable, with his balls perpetually coated in what I fondly refer to as “sex cream.” Their combined cum creates a frothy, milky white pudding, a testament to our shared passions. Dave, not inclined towards oral pleasures, grants me the privilege of indulging in Kim’s pussy every other day, while simultaneously worshipping her enticing asshole.

My primary responsibility revolves around caring for Dave. According to him, my asshole, mouth, and cock are his domain, and he diligently works to maintain our shared desires. Living this lifestyle fills me with gratitude. Kim ensures both of us remain in cock cages, recognizing that prolonged restraint intensifies our longing to climax, fostering heightened attentiveness. This elucidates the unique dynamics of our existence.

Stay tuned for the second part of this story, delving into the myriad kinky acts we’ve explored together.

“If you enjoy this narrative, cast your vote and share your lascivious comments. I relish reading them while indulging in personal pleasures.”

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