Dana-boy Ch. 03

It sounded so humiliating and wrong, but God almighty... It was exciting and along with him fucking me? I also wanted this to happen... Being kept in chastity for as long as I had been, and now that we were here, and this was really happening... I was starting to embrace my own wants, and those of Lord Sterling's, no matter how dirty and deviant they may be...

Even if that meant being pissed on as I knelt for him, naked in the sand...

Shivering again but trying as I could to cast the dirty image from my head I entered the bedroom and walking it's length... Past several large armoires and dressers I made my way over to his big king-sized bed, which was big indeed but as for being ornate and over the top as I had envisioned his bedroom to be? His bed was rather plain in comparison to ours back home, which was a huge four-poster deal taking up most of our bedroom completely with it's carved pillars and cloth canopy.

However undaunted I still loved the place, and I could hardly believe the up-grade I'd been given in my accommodation if you could call it that...

Coming from the small hut I was to be staying in, but I knew now this was his plan all along. Maybe Lord Sterling was just feeling me out as we met, but then I guess, liking what he was seeing, he made his offer, or more so, he told me I would be moving in with him.

And now as I found myself standing naked, hairless and clean again after sucking his cock for the first time in ritualistic sort of way, with him cumming all over me and my face and making me instead of taking and swallowing his seed. I could still hardly believe it, but here I was, in of all places Lord Sterling's bedroom, all by myself...

I felt an odd, calm edginess coming to me then, taking another second to drink in and realize where I was, not letting the moment get away. I savoured and cherished being here, in the Bahamas for the winter or even longer... Because I knew that this truly was a gift...

Enjoying that calm only momentarily I shivering in the next second as I glanced down looking to his bed all made up with nice linens, but there as well, sitting neatly folded on top I found the clothes he wanted me to wear...

"Oh gosh!" I said aloud first picking up the white silk hot pants he had waiting for me. They were tiny and looked so small, shimmering in white satin, I knew they would do little to hide me, my cage or anything else for that matter.

Stepping into the impossible small shorts, I worked them up with my legs pressed together and my caged little dick tucked under, trying to keep it and my compressed balls out of the way as I wriggled and gasping, I preyed the fabric would give a little.

Moving and twisting some, trying to adjust everything, I had my first glance into a mirror and seeing my ass, I could hardly believe it was mine, what with the impossibly tight fabric giving me a huge wedgie. The short were lifting and pulling my butt cheeks apart so far, I swore I could see my puckered little back ring twitching through the white silk.

Sighing and thinking that this was another intended idea of Lord Sterling's, wanting me dressed in the tight white shorts... He wanted my ass presented to him, and seeing myself I was thinking, that was exactly what he was going to get...

My ass, offered and presented, looking ready to be fucked hard with his big, thick 9-inches of stone hard cock...

Looking back then, I let my eyes drifted down to the bed where I saw the rest of my outfit, or what there was of it...

Seeing and biting my lip, I picked up the next and biggest item, a pair of white matching knee socks that once on me and pulled up, I felt myself tingling all over as they sat at calf height, just under my knees and were very sheer like nylons almost... But with open toes, they allowed my red painted nails to poke out the bottom making everything appear and feel just that much more feminine, and yes, down right sexy...

Mostly dressed now if you could call it that, I looked again and found the last three items of my clothing on the bed and puzzled for second, I had to figure out what to do with them...

Okay, well the first two were easy... They were just a pair of white wrist cuffs. like the male strippers wear, each with a little pearl cuff-link to help hold them in place... But the last item, once I had it turned around and facing the right way, I was able to see that it was nothing more than the top of a shirt, or so it appeared with only the collar and shoulders, and just two buttons up the front, it was short indeed and didn't even cover my nipples once I had it on me.

Wearing everything I did feel sexy as hell, if not completely gay, but as well... I was also feeling apprehensive thinking of how Veronica and Brother Reg were going to see me and knowing I was more than likely going to be fucked, taken by a real man for the first time right in front of them both... I knew that once Brother Reg laid on eyes on me in this get up? It was pretty much guaranteed he was going to be laughing his ass off...

Yet never the less and with a million different butterflies in my stomach, each one representing one of my million different fears, and with Brother Reg being but one of them... I found my little make-up kit, and with some pride left, and yes, a lot of fear as well... I put on the mascara Lord Sterling had asked me to...

Taking my time, I made sure I wore plenty just so that later, he and everyone else could see my tear stained face as he also eluded to liking... Seeing his boys 'efforts' all over their faces...

Feeling I was ready, or as much as I would ever be, and with a stomach full of the same butterflies, I nervously set out to find my Lord, my Master... Lord Sterling... My soon to be gay, dominant lover...

***

"Ah there you are, and pretty as a picture I see... Do come in Dana-boy, let's have look at you" Lord Sterling said to me then as I found him back in his living room where he sat at a big desk in the corner wearing a pair of glasses.

Dressed in his all white loose fitting clothes once again and attending to some paperwork or another. I felt my heart rate spike seeing him... He looked so different it seemed. Appearing distinguished and worldly, and like I was meeting a different man, all just from wearing a pair of wire rimmed glasses and sitting behind a big ornate looking desk...

"Hel-Hello my Lord... I hope I look good enough for you" I said to him sounding as timid as I felt right then, I was embarrassed dressed as I was, even if they were clothes he had chosen, still I felt so, I don't know? I felt very 'out of the closet' as I stood presented to him dressed in this very gay looking white silk outfit.

I'd been out in public dressed worse, or in things that were entirely feminine, more so than what I had on me, but still, I was seeing this another one of those threshold moments where once I cross over, my truth was out there and with no going back...

"You look wonderful my boy, and very gay indeed, just the way I want you... Please come stand near me, I want to see you up close and I have something else for you, something I'd like to you wear under your clothing" He said to me as a I stood there, nervous and twiddling my thumbs.

Saying I looked good, or 'gay' and dressed as I was, that was how I felt... Completely and utterly gay as I approached his big desk wearing the tiny white outfit and coming around, I wondered but not seeing what it was that he had until I stopped at his side...

"Do you know what this is Dana-boy? I'm sure you do, what with all of your earlier exploits" He asked holding up a medium sized butt-plug, it was hard to tell as he held it up between his two fingers like a ring where I also noticed for the first time that he was wearing a pair of black surgical gloves, and making me shiver in fear, I wondered but I didn't really have to because this time, I knew what was going to happen.

"Yes... My Mom has one that she put up my bum before she, before she, umm fucked me with her strap on" I said to him feeling brave just saying it like that... Coming out and telling Lord Sterling that Mom has fucked me up the ass with a strap-on, just in case he didn't already know...

"Indeed Dana-boy... I'm looking for ward to meeting your Mother, she does sound deliciously kinky, fucking her own son... Perhaps the three of us will have a special little training session of our own... She can fuck you with her big toy at one end, and I'll have you service me with that gorgeous mouth of yours at the other" He said to me, smiling and loving his idea of including my Mom in our sex games when she comes down at Christmas...

"Such a delicious thought... But of course this will be after she's had her fun watching me take you and fuck you hard, purely for her enjoyment" He added, saying again how he was going fuck me in front of her, just so my Mom could enjoy the sight and spectacle of seeing me impaled on his big monster of a cock...

Also, being as graphic as I had been, and saying he was going to fuck me hard, I suppose I was only getting what I asked for... Being open with him and telling him Mom fucks her darling son up his boy-pussy while dressed as her naughty little sissy girl... It didn't seem like we had anything else to hide...

"As for now, and as a part of your training with me" He continued, telling me why he wanted me plugged... "We will be using this rather small plug that will not so much train you, or prepare you for my cock... But more so we will be using it to show your willingness to please me, and to recognize your need to submit... Accepting the need of suffering, all in the name of your Lord"

Hearing him and with my body going into a soft tremble, all I could think was to ask..."Are? Are you going to fuck me later? After I've had that in me?" I said to him but hearing myself I felt the quivering grow further, recognizing what was happening and that the plug in his hand, it would soon be up my ass...

But wanting it still, plug or no plug, deeper down I knew I couldn't wait to feel that big cock of his tearing and pounding into me... Even if we did have an audience...

Lord Sterling's thick slab of real manhood was going to make little-Reg feel like Veronica's tiny pocket vibe, the one she would use on her clit when she would ride me from on top, using the small vibrator to push herself over the edge when my meagre, little penis couldn't get her there...

"Yes, boy as I've said, I'm going to fuck you later, after dinner... We'll make a ceremony of it... I know your wife would love to see you taken by me, don't you agree? We can even have her participate" He answered, letting me know again what was going to happen as I trembled, wanting it but still feeling very, very afraid...

"B-but can't we do that in private? You know like a real... Um, like a real gay couple?" I asked, saying out loud that we were a gay couple but boy, did my heart sink saying such a thing...

Admitting it for the first time, saying I was gay, even if it was to try and save my dignity when thinking of being fucked in front of an audience, for me though? It was still a huge deal...

"We can and we will... You and I will make love and we will fuck many, many times over... But in the beginning, I think things need to be hard for you Dana-boy" Lord Sterling explained...

"You need to learn and challenge yourself...and yes, you should also suffer... Simply saying you are gay is one thing, but in our case...and in the lifestyle we chose... You will be fucked by me for the first time in front of your loved ones... It's the only way... Now be good and lower those darling little shorts, I knew that outfit would look spectacular on you, my gay little sailor boy"

Replaying and telling me I needed to 'suffer for him' as he told me to lower my shorts and get myself ready to receive his butt-plug...

"Turn and bend, and don't worry... I have a very special kind of lube for you as well... This will go in easy, but like I said Dana-boy, this is also going to be a challenge"...

Moving from trembling to out-right shaking, and despite hearing him, I obeyed as I turned, slipping my thumbs into the tight waistband of the impossibly tight shorts he had me wearing and wiggling them down with my butt shimmying along I'm sure I was giving him a sight to be pleased with as I bared myself, giving him access to my exposed rear-end...

"Now Dana-boy, hold yourself open... You know what to do... That's it, grab those cheeks boy, here we go... I hope you like the lube I'm using, it's a home made with a mixture of cayenne pepper paste and tea-spoon of olive oil...my...my... The internet is a wealth of knowledge isn't it?" He asked, and rhetorically I'm sure as my eyes shot wide open, realizing what he was saying, I tried to stand up-right and move away but with a quick hand held to the flat of my back, I suddenly found I stuck there... I couldn't move.

"Uhhh! No! Please!" I begged as Lord Sterling, standing suddenly and with a powerful hand, he was able to keep me bent over with a strong arm coming around my mid-riff below my ribs, he squeezed holding me in place and giving me no chance to get away...

"Now, now! Stay where you are, boy... You'll take this plug and you'll suffer for me, do you understand?" He said to me in an authoritarian voice and scaring the hell out of me as he had me bent with a grimacing on my face, feeling one of his latex glove covered fingers pushing and sliding into me.

With the cayenne pepper paste as his is lube, the burning sensation didn't hit me right away it just felt cold at first... But I knew it was coming as I was left gasping inward, unable to utter as sound, feeling his big long finger pushing in and penetrating my frightened little butt hole...

"Ahh! Oh please my Lord... I won't be able to stand it! Ohhhh! Oh Sir... Oh... Nooo!" I cried out and where ignoring me completely, Lord Sterling had the plug at my back door and was pushing it home, working the small-ish thing into my under-prepared ass, and of course this made things even harder as he pushed the widest point past my breach with my ring closing then like a trap door...

The plug and it's stem being held and kept in place by my body's own natural reaction to clench up and tighten... I was doomed of my own doing...

But then...

The cayenne...

OMF'ing-G the cayenne pepper paste, I could feel it's heat gaining strength with each passing second, growing hotter, and hotter, I knew this wasn't going be good...

"Ohhh! Oh I can feel it... It's too hot! Please... I'll do anything I'll let you fuck me in the public square, anything, anywhere you want... Oh God I don't think I can handle this my Lord" I cried, begging and pleading bargaining my life away if I could... Anything to get him to reconsider the heat was becoming so intense... I knew there was no way I could wear this thing all night...Not like this anyway, not covered in that evil cayenne pepper paste!

"Just give it some time, young man... The sensation will fade and soon you'll feel a warm glow all over" Lord Stirling informed me as he went on, telling me more, some of which I believed and some, I hoped wouldn't happen...

"It's good for you and will help you sweat out any toxins floating around inside, especially with that cocktail of female hormones you're taking... Now come, be a big boy for me... Up you get, pull up your shorts... Because if you keep fussing with them pulled down, I'm going to spank that cute little ass of yours and make you feel even hotter! Is that what you want?" He asked, or threatened and not wanting to be spanked I bowed my head shaking out a definite 'No'...

"I didn't think so" He replied to my begging and of course, hearing him, I backed down not wanting to feel hotter than I already was, which by this time I thought my ass was on fire as I righted myself feeling hot all over and sweating already.

Plus he sounded so much more forceful and almost angry even. So, fearful of anything else he might do to me, I didn't say a word after that...

All I could do was wince and bounce from one foot to the other, hoping and praying he was right and that this horrible, hot, itchy burning in my ass and whole lower region would soon fade to a less intense warming feeling...

However as it raged on with me beginning to sweat and shake rather profusely, for the time being, and for however long this inferno up my ass should last... I was rather inclined to believe otherwise...

Continued...