Becoming a Hole - Beginnings

I'm a rule-follower, and I always have been. I guess you could say it's second-nature to me, and I think it's served me pretty well. I was recognized throughout my schooling for my perfect attendance; I was always rated the top athlete in the state for anything I tried; and I've worked my way up via reputational capital to atypical prestige in my professional endeavors as an adult. So again, I think it's fair to say that my rule-following nature has served me pretty well in most ways.

And I fucking hate it.

It may sound weird, but doing what I'm "supposed" to do always feels so fucking stifling, and that's mostly because doing what I'm "supposed" to means suppressing what I'm not. Almost like, every time I do something to conform to what's expected of me, I'm adding another shackle on the endless chainlink containing my darker desires. And trust me -- locking up and suppressing has been my constant state for as long as I can remember. Same old story, of course (sing along if you know the verses): I grew up in the cult of southern Baptism as a gay man, though no one would have guessed it by my athletic stature and constant parade of girlfriends; my parents actively punished discussions (or even questions) about sex and romance; pornography (of any kind) was vilified; and social expectations mandated peak masculinity and a heterosexual ideal in presentation. So there was a clear way to exist correctly. Fuck girls, deepen your voice, masturbate infrequently (and NEVER to porn), play sports, look away from other guys in the locker room, leave at least one urinal between you and the next guy, wear boxers, etc. etc. etc.

And all I wanted -- all I can remember ever wanting on the most primal of levels -- was the exact opposite of all of that.

Men. Cocks. Musk. Balls. Armpits. Blowjobs. Cum (and lots of it). Piss. Anal. The taste of a hole. Jockstraps. Lingerie. Poppers. Constant raunchy, filth porn. Mutual masturbation, circle jerks, gooning, three-ways, gangbangs, cuckholding, cheating, bukkake, BDSM, spitting, leather, cum control, restraint, and so fucking much more. In short, I wanted everything I wasn't supposed to have.

Not wanted. Needed. Painfully, achingly, unequivocally, and desperately needed.

I have always done what I was supposed to. I followed the rules, and to some extent, I still do. But when I was 19, I finally decided to claim my right to perversion and filth. And for those of you will with me, this is the story of that journey.

Going to college was liberating for me. I remember really hoping to be able to get out of Mississippi, where the safety of anonymity eluded me in my small town, and land in a really urban, really huge city where I could finally exist as an unknown. And luckily, that happened -- I got a scholarship to a comparatively large school in NYC, a city known for its population density and, fortunately for me, its sex positivity.

By the time I'd reached the age of 19, I guess I was pretty experienced sexually -- at least with women. I can't count the number of drunken, sloppy blowjobs I got after football games and such, and honestly, with my stature, I could get (and in fact got) any girl I wanted. I came on tits, ate girls out, enjoyed "God's loophole," and had more than my fair share of pregnancy scares (girls always wanted my dick raw, which was fine by me), and I guess I'd describe all of that as simply... "fun." Satisfying. But something was always missing, and I guess I always knew that. Despite all the jizz I'd sprayed, I was still the walking embodiment of blue balls and pent-up sexual tension. My genuine sexuality -- the perversion that lie dormant inside me -- was set to erupt, and it begged to, but I couldn't acknowledge it. Not yet. Not there.

Physically, I think any porn aficionado worth his salt would have described me as a verifiable, blue-collar jock at the time -- 6'2'; perpetual 5' o-clock shadow; white skin; muscular frame from a decade's worth of football, basketball, and wrestling; blonde hair; hazel eyes; thick guns, treetrunk legs, and a muscular ass that never quite reached the level of "bubble." So, in short, masculine. In terms of equipment, I've always felt lucky with the 7.5" I've been given -- I love my veins, the way my mushroom head bulges when I'm really turned on, and the fact that I precum (I guess not all guys do?), but it's certainly nothing compared to the horse cocks with ostrich-egg balls I've seen in my years since.

I really lucked out my freshman year in that I was selected to be in a single-occupancy dorm. How was that lucky, you may ask? Privacy. Privacy to explore my interests -- all of them - privacy to not have to pretend my dick was a compass that only pointed towards pussy, to find out what I was really about. I remember distinctly the instant I stepped into my dorm, turned around, and clicked the lock. My cock, almost instinctively, perked up and twitched. It was almost as if it sensed the unrestricted freedom it was about to enjoy and wanted me to not waste a single second of it. In retrospect, it's almost comical that my first college task was cleaning up my freshly sprayed load off the wall (even before I even unpacked my first suitcase), but in an important way, that small moment of prioritizing my pleasure and sexuality -- my perverse, primal urges for satisfaction -- was actually the perfect prelude to what the next year would be for me.

That first night was memorable because it was my first night of genuinely and completely unrestricted internet access. I no longer had to worry about my parents monitoring my internet history for anything spicy or potentially barging in while I was pumping out a load, which was unfortunately really new to me. The secrecy itself got me excited. I remember returning to my dorm after my first dining hall dinner, recognizing the potential for what the night could be, and immediately starting to strip. The moment my rising meat bounced out of my boxer briefs, I felt a surge of power that, until that moment, had been completely foreign to me. There I was, cock out, hole accessible (I remember distinctly being aware of my hole for the first time in this moment), completely vulnerable; and yet, no one could take that from me. This moment, this nakedness, this hard-on, this scent -- it was all mine, and I could do with that moment whatever I wanted for the very first time. That simultaneous vulnerability and empowerment turned me on. I felt the throbbing of my cock all the way through my taint and couldn't wait for this -- this freedom -- to be my new norm.

Wasting no time, I sat my desk in front of my laptop, turned on incognito mode, spread my legs to bring my focus singularly to my pleasure center, and took in the moment of possibility that the google page held in front of me. Numerous possibilities crossed my mind -- standard porn, chat rooms, video chat websites etc. etc. However, my pleasure demanded more of me. My cock was voracious -- it was hungry -- and it was insistent that it get more than it could obtain through a screen. It wanted male skin, it wanted musk, it wanted taste. It wanted more. I remembered reading something about different websites through which people could find sexual partners, and at the time, Craigslist was a common, non-committal option for anonymous encounters. The idea sent a spark of what felt like electricity through my body, almost as if arousal took the form of a very real visceral energy, and I took this as a sign; so I obeyed and immediately went to the Craigslist "men for men" section of casual encounters and started looking at the buffet of sexual appetizers waiting to sate me.

In retrospect, I suspect that the next couple of years would have been very different had I gone to literally any other website that night.

A brief perusal of the postings on that first page revealed some generic (though enticing) titles: "hot top looking for quick blowjob;" "looking for loads;" "str8 looking for jo bud;" etc. But the third posting was different. The title was simply: "are you brave?" The mystery drew me in. I clicked on the title, and the description advertised the following:

"looking for brave cum slave. u come in blindfolded and undress, and we (~10 guys) have our way with you for 2 hours 2nite. U don't speak. U don't cum. u just take loads wherever we want. Send stats and pics if interested. U get no pics from us."

I wasn't stupid, remember. I knew how this ad sounded from the outside. The rational part of my brain reacted with innumerable attempts at very reasonable data-based warnings: danger, STI's, regret, shame, etc. But there was another part of me -- the lewd part, the hungry part, the part that had been deprived of meaningful release since my sexual awakening -- that agonized with desire. Additionally, and importantly, the idea of this big, muscular, dominator of women completely submitting to the needs of others -- and in particular other men -- sent shivers to my cock. How degrading it would be. Shiver. How dangerous. Ache. How humiliating to be relinquishing my control not only over my safety but also my pleasure, my body, and literally (potentially) my livelihood. Throb. My body betrayed my desire: my piss slit was oozing precum, my taint was pulsing, and my muscles loosened almost as if in submission to the idea of complete degradation and servitude.

I immediately replied, and I made sure to attach pictures of me spreading my cheeks to reveal my willing but untouched hole.

"19yo sub jock in. new 2 this but horny and willing to please. Drench me. Pics attached. Location?"

Simply due to chance and the possibility that the poster had already gotten the need filled, I honestly expected that I wasn't going to get a reply. However, two minutes later (before I had even finished fully browsing other listings on the first page), I got a message back instructing the following:

"perfect. Address below. No underwear, blindfold urself before you ring the doorbell. We'll open the door, u come in and strip and get on ur knees. U disobey, u'll hurt. B here in an hour."

I smirked. My cock throbbed. Precum leaked down my shaft. I replied. I dressed. And I left.

I couldn't have known what was in store for me when I got there. Or what it'd unleash in me going forward.

I would never be the same. And neither would my hole, as you'll soon see.

TO BE CONTINUED...