Club Sissy gets Broken in

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After a steamy initiation, a submissive sissy gets broken in.
2.2k words
4.72
8k
16

Part 1 of the 1 part series

Updated 04/30/2024
Created 04/27/2024
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After my sauna initiation, things got very busy for me at the club.

A quick recap: I'm a quiet, competent financial consultant with a modest but reliable clientele for whom I often travel doing risk assessments for their variously lucrative investment strategies. I'm good at what I do, and get rewarded well, but several of my clients have also recognized that my slender, pale, smooth, somewhat effeminate body might be useful for other things. There too I am increasingly well-compensated. In my home city, where I've settled in with a major firm where I do most of my work, I recently took on a free trial of an exclusive fitness and social club on the top floors of the building I work in.

After a Grindr hookup got me a free all-inclusive membership there, it was a couple of weeks before I learned how I'd be paying for that membership. My first job was getting throat- and ass-fucked in the sauna by a visiting member while two gym managers guarded the door. After that, my Grindr guy, who told me to call him 'Austin', and who was one of those managers, came back in, grinning. He then worked me over some more, chuckling as I whimpered while he bounced my slender frame off his condom-sheathed and well-lubed cock.

As I lay naked on the floor, glistening with sweat and recovering my breath, he then explained to me that I'd be "working" like this at least twice a week, for him and his friends, and for visiting members who had booked my services through a network they maintained with fellow sissyfuckers around the world.

All of the gym and club staff involved seemed to be part of a regular STI testing regimen, according to Austin's account, as most of them also worked in the adult industry, either as performers or escorts. Austin also explained that, depending on the activities I'd be asked to perform, clients would also be required to test, but as often they'd insist on wearing condoms. I was free to accept or reject any particular activity, but Austin strongly hinted that my job was to please the staff and clients. I too would be part of the regular STI testing regimen, and I'd have free meals at the club, so I could spend as much time here as needed.

Given the price of even a visiting membership at this club? This was a damn good deal for a secretly slutty sissy who probably would have taken all this cock anyway, without all the perks.

I wasn't told anyone's real names, and my Grindr guy - Austin - told me names didn't matter, and for their visiting executive clients, names were actively discouraged. Not that someone enterprising couldn't figure out who was who, and not that the wealthy perverts in this rarified world of stupid rich executives would care if they knew their colleagues liked dominating femme sissies in their spare time, but shareholders might, so discretion and privacy was important to the gig: this was essentially an exclusive kink/fetish sex club within a club, with reciprocal member privileges around the world, and they seemed to run like a well-oiled machine.

Now that I'd been brought on as "talent", I began to notice young women around the club who seemed not to be the target clientele, and several other men who, like me, were usually in the pool or hot-tub or sauna when they weren't doing cardio. These men tended to be slim, a bit shorter on average than the other men, and were always shaved smooth.

They were also, like me, quiet, pale, and a bit effeminate.

Clearly I wasn't the only gym slut, or even the only sissy gym slut.

As Austin was finishing up in my ass after my first sauna fucking, he told me there'd be an important meeting for me and some of the management, early next week. I should check my email.

And sure enough, the next day, I received an email from the club management, which directed me to another site, where an account was set up already, linked to my email. I was on a well-designed staff management platform, and I found a new message there, along with an integrated calendar, telling me when and where to be at certain places in the club.

This coming Monday evening, apparently, I had a high-priority meeting in the combat sports room at 8pm, which would last ... the meeting was listed as open-ended.

I clicked on the instructions tab of the meeting entry, and found a detailed note about how I was to be prepared. For this meeting, I was to come naked under a club robe, shaved or preferably waxed smooth, fully douched, well-lubed, and with a butt plug in place, that probably should be worn all day.

I admit that I felt a lot of butterflies and was very distracted during my workday on Monday. I keep pretty smooth all the time, but I'd let my body hair grow a bit for a few days, so that I could get a wax job on my ass and legs over the weekend. I'd found a sizeable but manageable butt plug in my locker the day after my sauna fucking, and so I'd spent this Monday morning lubing and struggling to slip it into my tight little asshole. I spent most of my day walking or at my standing desk, as sitting would have been very awkward!

As evening arrived, I left the office and went straight up to the club. In my locker I found a disposable enema kit, and a tube of lubricant. I undressed, put on the robe that was also there, and tried to discreetly waddle to one of the private bathrooms with my enema kit, suddenly becoming very aware of the plug that had been stretching my ass all day.

In the private bathroom I leaned awkwardly over the toilet and used the enema kit, ensuring several cycles. I washed the plug well, covered it generously in lubricant, then eased it back in past my now rather more receptive sphincter. I disposed of the kit and now-empty tube, put my robe back on and, heart now pounding, wandered down to the lower level of the club to find the combat room.

The door was locked. A sign posted on the front announced a private function for the evening. It was just before 8pm. I stood awkwardly for a few moments, then gently knocked.

A huge gym attendant who I didn't recognize opened the door, smiling.

"Come on in, sissy"

I entered, and heard the door close and latch behind me.

The room was, at present, lit with a low orange-hued light from recessed fixtures high along the walls, just below the wood-paneled ceiling. The floor was padded, as were three of the four walls, while the fourth wall was a long window looking out over the darkening city.

All around me were naked men, some of whom I'd seen around the club. All were very muscular, and each was considerably taller than me. The average complexion was also darker than my pale skin, but it was a diverse mix of very fit, very ... erect! Club employees. There were probably eight men altogether, but I was so nervous I didn't really count. I felt hands behind me gently pull my robe off my shoulders, leaving me standing in the center of the room, chest pounding, a smooth pale sissy surrounded by very masculine men.

"Kneel down, please"

It was Austin. He stepped in front of me, also naked, his cock fully erect.

I did as I was told.

"Spread your knees, slut. Further - there, that's good"

I could almost smell the testosterone in the room, as these men sauntered closer, surrounding me. I felt someone behind me, then felt something warm and wet over my shoulders. I realized I was being slathered with some sort of aromatic oil. Two strong hands rubbed the oil down by back, then reached in front and massaged it into my chest and along my thighs. I gasped as I felt his hands slip back around to my buttocks, and a finger gently rubbed the oil around the base of the plug, still firmly in my ass.

"Happy to tell you your test results came in last week. Clean bill of health. When we're fucking you, we won't be using condoms, but as always you're free to ask. As you know, we're all tested regularly."

"Good" he replied as I meekly nodded my assent.

"We wanted to bring you in for introductions, now that you're cleared and ... well, one of the team."

I felt a hand gently but firmly push me forwards, arching my back as my chest and cheek met the cool, soft matted flooring. With a slurp, I felt cool air rush in my briefly gaping ass as the plug was pulled out and tossed aside, landing with a dull thump somewhere behind me. The men around me shuffled closer, and from my sideways view I could see dark muscular bodies glistening in the soft light, hands stroking well-oiled erections.

"And by 'introductions' I mean, breaking you in as our latest sissy club slut."

Austin chuckled as he said this, and I felt him kneel in front of me, grabbing my hair and pulling me up on my elbows as he pushed his cock past my lips.

The men descended on me as a ravenous pack, and I remember thinking that whatever oil they used on their cocks and my bodies, tasted like strawberries.

The next two hours must have been a sight. In fact, I know it was, because eventually I watched the footage, the whole sordid affair being recorded from three different angles.

I had access to the footage via a link in the online platform I'd been assigned to. I watched it a week later on my tablet, furtively, locked in a small corner conference room reserved for client meetings, trying to control my racing heart as colleagues walked past the glass walls, going on their day. My ass and my small little cock quivered remembering the night.

In the video, you can see, switching conveniently from above, to the side, and from an oblique angle behind, eight dark muscular bodies ravishing a glistening pale body that looks tiny compared to some of their massive bulk. Cock and after cock slips in as these men mount their prey, sometimes pulling up on my hips to better penetrate deep into their conquest.

Meanwhile, at the other end, men patiently fucked my mouth, waiting for their turn in my ass, or inserting their soft but still substantial cocks for cleaning after already depositing their seed deep in my bowels. At a couple of points in the footage you can see occasions where a limp, spent dick grows harder in my mouth, a hand under my chin directing my increasingly panicked gaze upward as a soft cock in my mouth grows into my throat and begins deeply fucking there, before tapping in and returning to my increasingly limber ass. In those two moments you can hear me whimpering and moaning before another cock finds its place in my mouth, and once again the only sound on the video is rhythmic slurping and sloshing as my pale slender frame is bounced between two cocks.

The footage ends after a particularly savage fucking, where the largest and darkest of the gym managers, the head trainer and weightlifting coach, pushes me down to the mat, his enormous bulk crushing the air out of me as he grinds his cock into me. The video shot from above is mesmerizing here, with the slow steady undulating of beautiful, chiseled black buttocks driving his erection impossibly deep, his python-like bicep glistening as he slips in around my throat and pulls my head back. As the vantage switches to the front view, you can see my eyes bulging and hear a high-pitched squeal with each thrust, until finally with a low growl, the giant man lets me fall back to the mat, utterly spent.

Before the footage fades to black, there is about a minute of film from the camera above, in which I lie there, face down, legs spread wide, body heaving with ragged breathing and an occasional post-orgasmic twitch as semen steadily leaks down my balls and onto the matt below my loins. Apparently I had spurted an orgasm, hands free, during that final grind-fucking. Apparently that was a big deal that put me high on the list of fuckable sissies, not just for Austin and his fellow managers, but also for several wealthy foreign clients who had watched the footage live.

"Hey, you okay?" the voice was clear, but muffled through the glass partitions.

The tapping on the glass door shattered my reverie. I looked up, stunned, to see a work friend standing outside the conference room, looking concerned.

"You've been reading those contracts for, like, two hours, without a break. Come get a coffee."

I smiled, nodded, and waved. "Go ahead, I'll join you in sec" I replied, desperately trying to regain my composure. I felt a warmth around my belly and groin, and below the table discreetly reached into my pants under the guise of adjusting myself before getting up.

I'd orgasmed, again hands free, just by watching the footage of that hulk pounding me into complete submission. I shuddered, wondering just how much I'd be willing to do for men like these.

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ChloecrossedChloecrossedless than a minute ago

Loved this, super hot, a real fantasy of mine. X

oldersissysnowbunnyoldersissysnowbunnyabout 16 hours agoAuthor

Doug, funny you say that ... not the next story, but the one after that, yes!

DougJonesDougJones1 day ago

A great follow on story. I'm hoping that one of the rich overseas visitors will request he visit abroad. I'm thinking a Turkish bath in Istanbul as one setting....

oldersissysnowbunnyoldersissysnowbunny2 days agoAuthor

There are a few directions I see the series taking, but in all of them, out slutty protagonist manages to get out relatively unscathed! 😊

AnonymousAnonymous4 days ago

What he's doing is killing his career. Pretty sensitive clientele with his work, to put it out in such a public way.

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