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Dana-boy Ch. 04

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Amateur

(Author’s note: This chapter does contain GAY SEX)

Sex on the beach

It had only been about twenty minutes since Lord Sterling had pushed the butt-plug up my ass, the one he had so thoughtfully lubed up with a home made concoction consisting of cayenne pepper paste and olive oil, and as of yet? The incredible heat and discomfort he told me would pass? Yeah, so far it hadn’t…

“Why are you squiggling around in your seat Dana? What’s the matter? Do you have sand fleas in your pants?” Veronica asked with a curious smile as we were all gathered for dinner out on the rear patio of Lord Sterling’s big white mansion style house. We were faced towards the beach with the Sun having crested the Western horizon, giving the whole place a warm, orange glow…

But me, of course, I couldn’t enjoy the scenery with my attention most certainly directed elsewhere…

“Ah, yeah s-something like that” I replied being sheepish and not wanting to tell either her or Brother Reg what had me shifting continually in my seat while searching for that ever elusive comfort zone…

“I love the clothes Lord Sterling has chosen for you” Veronica added, commenting about how I was dressed for the first time after both she and Brother Reg had spotted me as they approached. Walking hand in hand across the sand together, Veronica looked so gorgeous in just her tiny white bikini top and a sheer, see-through sarong wrap revealing that underneath, she had nothing else on her… From the waist down she was naked…

“Yeah Dana-boy, you look like you have a real bug up your ass, and ah, that outfit? I gotta say man, it suite you to a tee!” Brother Reg agreed putting in his two cents while smiling at me, or mocking me I wasn’t sure which. But at least he wasn’t falling over laughing…

“Yes, I though he would look good in this outfit, and Dana-boy? Tell everyone why you’re wriggling around like a fish on a hook… Go ahead, we have nothing to hide here… Tell them what you have in your cute little bottom” Lord Sterling interjected as the four of us sat with a myriad of servants appearing form where I wasn’t sure, bring us plate after plate of fresh Island cuisine.

“I… I… Uh… Lord… Lord Sterling he, he gave me a butt-plug…to…to wear for him…. It’s like the one Mom has but um… Lord Sterling, he used a different k-kind of lube… One made with… made with umm, c-cayenne p-pepper” I stuttered out half under my breath looking away and down to my plate. I was embarrassed and didn’t want any of the staff to overhear me as I explained with them hovering around.

Even if I’d never seen any of the servers before, or knew who they were, I still didn’t want to be shouting from the roof tops that I have a fiery-hot butt-plug inside me…

“Ouch!” Brother Reg commented with a grimace, asking me why… “What did you do to deserve that? Did you piss him off already Dana-boy?” He questioned with a chuckle, wanting to know if I had angered Lord Sterling already, but as embarrassed as I was, that wasn’t it. That wasn’t why he had challenged me with this task as he was calling it…

“No, Dana-boy hasn’t crossed me, not yet… I am however testing him you see, and not to inflate his ego any but the darling boy is doing quite well” Lord Sterling added in this habit of answering for me, telling Brother Reg that I wasn’t being punished, but rather I was being tested and even though I was doing well, according to him I shouldn’t let it go to my head…

“Tested how? Are you sure you’re okay baby?” Veronica asked further as she turned to me, trying comforting me at least, wanting to know if I was okay with this torturous thing inside of me…

“Ye-yeah, it’s it’s not as bad as it was at the beginning, but Lord Sterling he, he wanted me to s-suffer for him, and…and I understand that… The test is of my loyalty to him, and it’s…it’s okay, I’ll be fine” I answered, still stuttering some, telling Veronica I was okay, but really I wasn’t…

True enough though, I could feel the heat beginning to ease, not as much as I might have hoped for by this time mind you by now however? I was about ready for relief… Any kind at all…

“Yes… He’s fine and like he said… The darling boy is doing this for me, and I am very, very proud of him… But still the night is young and I have a feeling by the end of the evening, all of us will be feeling the same… We’ll all be very proud of Dana-boy for not only telling us, but showing us just who he really is… Isn’t that right my dear boy?” Lord Sterling went on telling Veronica and Brother Reg they would be proud of me by the end of the evening.

Looking to me as he spoke, and asking me if I agreed, all I could do was smile and nod as I felt my stomach roll over, both waiting and fearing what was to come… I couldn’t really say no, because as I had also been told… Saying ‘no’ for me… It wasn’t really an option any more…

“Ah here we are, the main course… I hope everyone likes Grouper? It’s been caught fresh today, bahis siteleri kind of like our young Dana-boy here” Lord Sterling declared as our main courses arrived with everyone except me having a titter over his little joke.

Which was him implying that along with our fish dinner, I too was on the menu… Like our Grouper, I was his fresh fish, caught just today…

Looking down, once again I paid attention to my plate as this time I went for my glass of wine…

“Isn’t this lovely? Is everyone’s glass full?… Good, because I’d like to make a toast” Lord Sterling said then as he stood at the head of the table with his glass held high, and from the onset, I knew his toast was going to include me and whatever we were doing here on his private estate.

Joining him the three of us followed his lead, looking to him with our full attention as we all stood…

“Now my dear friends, both old and new… We’re here today in this Paradise and I raise my glass to you”

He began, rhyming his words into what sounded like a poem…

“We are here to enjoy this life, including all that we may do and see, yet however if should come the day we should ever disagree?”

He added then paused…

“Well then…. Fuck you…and here’s to me!”…

Ending his odd, funny poem we all stopped and waited in a momentary silence as Brother Reg joined in and calling out “Here! Here!” as we all broke out into laughter hearing the rest of Lord Sterling’s rhyming toast, and I had to say, it certainly wasn’t what I was expecting…

He was being funny, charming and not how I was thinking. I figured his speech would probably be something serious and stoic that would include me being with him and wanting to try out my ‘gay-water-wings’ as I dipped myself into his ocean, his lifestyle…

Indeed though, I was wrong… Thinking he was going to say something deep and meaningful, yet with his English charm and razor sharp wit shining through, it was one of the first times I didn’t feel so afraid of him…

Eating and drinking in such beautiful and posh surroundings, Lord Sterling took it upon himself to ask us all some questions about our past, or more so it was just Veronica and I, asking about our younger years to begin with. Things like how we met, and of curse going deeper… He wanted to know how we allowed Brother Reg to come in and change everything…and I do mean ‘everything’…

“And then after he admitted to wearing my panties, I thought it would be good for him to start wearing them more often… But as well as dressing up, I guess it was our dildo, the one we called little-Reg… That’s when we really turned the corner” Veronica went on explaining to Lord Sterling how things with us had come to be, including my earliest cross dressing adventures, and embarrassing me to no end I sat listening to her openly mention our dildo named ‘little-Reg’ as I cringed inside…

“Dana grew to love it when I’d use it on him, and with all of the practice with us fantasizing about the real Reg… Or Brother-Reg as we call our wonderful leader these days” She added, speaking to Lord Sterling but turning to look towards Brother Reg beside her, she smiled while taking and holding his hand.

Continuing she didn’t hold anything back, much to my embarrassment…

“It was only a matter of time before we had Dana trying out the ‘real’ thing, if you know what I mean? Dana sucked his first cock out in our hot tub and… Oh my God was it ever an amazing thing to see” She went on, still holding Brother Reg’s hand but turning with a smile and a crinkle of her nose as she looked to me…

“Yes, Dana-boy has already proven himself to me, haven’t you dear boy?” Lord Sterling added, asking me as more of a statement as he went on telling the two how I’d sucked him off once already…

“I’ve sampled his wonderful cock sucking abilities, and Dana? Tell your wife and her lover how I’ve already claimed you as my own… What did I have you do? Go ahead, tell your wife how you’ve sucked my big old cock for me and how I’ve christened our new relationship”

“Uhhhh”… Was all I could mutter as Lord Sterling went on this time, adding to my already embarrassed state, telling Veronica and Brother Reg how after sucking him to completion he had cum all over me, giving me a facial that was much more symbolic than him just dumping his load on my face to humiliate me…

“He…Umm, he came, he uhh ejaculated on…on my…my f-face” I managed to say as I reached for my glass, downing my wine with the rest of me feeling almost as hot as my ass with that cayenne pepper coated plug doing it’s intended…

“Oh wow! I wish I was there to see that! You know I always liked seeing two guys doing it in the bi-sex videos we’ve watched” Veronica added which Lord Sterling used as a cue, the key to open the door into his next thought, or the direction he wanted us all going in…

“Oh believe me Veronica dear it was a sight to be seen, that much I’ll tell you… Young Dana-boy here is quite canlı bahis siteleri the cocksmith and I’m grateful you and Brother Reg have him so well trained, because with some doing, he was able to take all of me… I was quite proud of him… However, you don’t have to worry about missing anything because you see dear, and as a treat to you a both, I’ve informed Dana-boy that I will fuck him for the first time… In front of you”

Hearing him and cringing again, I sank in my seat some thinking the worst but Veronica was feeling much different…

“Wow Dana! Did you hear that? Or, I guess maybe you know, but are you okay with this baby? Is that how you want it? With us watching?” Veronica asked looking all smiles and quite willing to watch as Lord Sterling takes me and fucks me for the first time.

Showing some concern for me, she did ask if I was okay with this… My being fucked by a man for the first time with my wife and Brother Reg there watching…

But as well, and what Veronica didn’t now at the time was something else I had agreed to… That other thing I said I would do while my Lord and new ‘Master’ was making me his… What I was going to say and declare as he buried his steely hard, 9-inch cock into me balls deep.

I was going to come out to Veronica and to Brother Reg… As proscribed by Lord Sterling, I was going to tell them both that I was gay…

“Ye-yeah… We… Um, we spoke but gosh… This all so embarrassing, you know? Talking about this so umm, so openly…It’s…it’s kind of hard to uhh, take” I answered struggling and hoping they would understand…

“Yes Dana-boy I can see how you’re still struggling, but don’t worry my pretty boy, I’ll go easy on you at first, just so that I’m not as you say… Hard to take” Lord Sterling commented and smiling as he rose from his seat, but catching me a little off guard I watched surprised as he pulled the tie-cord of his loose fitting white cotton trousers and letting them drop where he stood exposing himself to us all…

“Ooh-la-la! Well would you look at that Dana! I’d say your dessert is served! But you’d better be careful because even I’d love to slice off a big piece of ‘that’ cake!” Veronica chirped, looking surprised as I did, seeing Lord Sterling drop-trow like that, right there at the dinner table…

“Perhaps another time dear Veronica, but for now indeed… Dana-boy, my cock will be your dessert… Now come let us relax over liquors and coffee while we watch our young charge here pleasure and resurrect this old fossil” Lord Sterling declared as he stood half naked but looking casual, holding out his hand for me with a confident smile as two of the servants paying no heed whatsoever and like this was something normal, they came in set down a large silver serving tray with a bottle of some Island liquor and a coffee urn before collecting all of our dinner plates and then disappearing once again.

Listening and watching him get naked like that in front of his staff that I assumed were all locals, it didn’t seem to phase anyone… Except of course for me, who when listening to him, it sounded like I was being offered a much different kind of ‘dessert’ or an after dinner treat…

But as well, having him tell me and everyone else it was time, we all rose as he instructed and followed him over, across the lawn and into a small pagoda. Or it was a gazebo that was open at one end, yet upon entering we were soon to discover that most of the interior was a big cushion or mattress type bed.

It was custom made to fit the back half of this octagon shaped, roofed structure, like a day bed you can use to get out of the Sun, among other things as we, or I was about to discover…

I was feeling reluctant, knowing now that my hour had come and soon I would be making a declaration of my own… Admitting something to both Veronica and Brother Reg, and I guess to myself really, and oddly, my only wish was that Mom could have been there as well…

***

“Oh this is cozy! I’ve been eyeing this little party hut all day but now that were in here, it’s really kind of cool, like our own little version of that strip club you took me to… Remember Brother Reg? It was our first date?” Veronica commented as we entered…

“Yeah it’s kind of like that, only instead of a stage full of strippers we’re gonna get to see a live sex show!” Brother Reg replied while smiling and coming in to sit on one of the built-in couches along the side with the big bed taking up the back half of the hut…

“Oooh! I can’t wait but what about you? Are you okay seeing this? Watching Dana get plowed with a big cock and having gay sex right in front of us?” Veronica replied as I went to sit with them but Lord Sterling taking me by the arm instead, he began leading me up onto the bed…

“Yeah I’m cool… I mean it’s not like I sit around watching gay porn… But hey, we’ve getting into some kinkier shit these days, and I don’t mind Dana blowing me… So, no, this doesn’t bother me at all… I canlı bahis actually wanna see this!” Brother Reg answered but being distracted myself, I was suddenly faced with Lord Sterling’s big, semi-hard cock, laying there as he sat back, resting on his elbows and smiling while pointing to his half-hard member…

Settling on my knees up beside him, I leaned over taking him in hand and feeling myself shake I tried to put the other two out of my mind as I lowered myself, ready to take him into my mouth, ready to suck my Master’s cock for the second time that day…

“Mmm… Unngg, uhh” I mewed dragging my wet tongue along his length, laying it out flat and licking him like an ice cream, I made him wet with a few up and down passes and stroked him with my hand… Everything was starting to feel strange and surreal again where this wasn’t me, I was living and acting as someone else… Being gay and sucking cock…

“Oh yes, that’s it… You’re making this old man feel young again Dana-boy, your mouth and enthusiasm for sucking my cock have me stiff and soon you’ll have me ready” Lord Sterling declared as his big pole stiffened with my efforts, and yes I was showing an enthusiasm…

I had a want and hunger for cock coming to life inside of me now that we were getting down to it, and oddly enough as I thought of it? This was the first time I wasn’t held back or forced to climb my invisible wall… The one built from my fears, the shame and reservations about who I am and what I’m doing… Serving my new Master and his great big 9-inch cock.

Feeling this, and as ironic as it was… It made me shiver knowing that I wasn’t so afraid, I had a growing deepening desire to be with him… Even with an audience, yet the frightening part was discovering that Lord Sterling, his big cock and his dominance, they had taken down my wall once and for all…

I wasn’t so afraid anymore… I wasn’t so terrified of coming out and telling them both… Telling my wife and her lover that I was gay…

“Oh Wow Dana! Look at you go! Oooh this is exciting isn’t it?” I heard Veronica say as I turned myself more, moving in between Lord Sterling’s parted thighs while remaining on my knees, stroking and sucking his cock as he sat up himself and reaching over me, he began taking my clothes off, starting with my little satin half shirt…

“Yes Dana is quite good, he’s making me nice and hard, but come, lets get you naked and ready” Lord Sterling replied first to Veronica but then turning his full attention to me he soon had me naked, stripped of everything except for my pink little chastity cage and the plug in my ass.

With my back to Veronica and Brother Reg, and with my bare ass tilted upwards while I moved and shifted some, enough to rid myself of the tight and confining little outfit, Veronica noticed my butt plug, which at the time and being stripped naked, I was also looking forward to having the still rather hot feeling thing removed.

Even if it was soon to be replaced with something else… Something much bigger and very, very real…

“Oh I love your butt-plug baby! Are you still burning up back there? You must feel numb by now!” She commented brightly as both she and Brother Reg shared a laugh at my expense…

“Umm…Ummph” Was all I was able to mutter back however as Lord Sterling, my new Master had me with a hand to the back of my neck and where with a smiling insistence I was forced down on him, filling me mouth and upper throat with his huge un-cut cock-head and his equally big, thick shaft…

“Don’t talk with your mouth full Dana, it’s not polite!” Brother Reg interjected joking again and even I saw the humour in what he was saying but, hearing him next? He set off a series of events that would lead to me being taken, fucked, if not stolen away in what was to be my defining moment I suppose you could say…

“Hey Vee, go see if the little girly man needs you to take his plug out, I’m sure Lord Sterling won’t mind if you help usher your ‘ahem’ husband into his next life… His gay life that is” He added as I gagged a little harder, trying to swallow my Master’s cock, or as much of his overly impressive 9-inches as I could manage…

“Yes… Come Veronica, I do want you close by when I take him and put my cock into his body… Climb up here with us… You may take out his plug, and as well, I have more lube… It’s just there in the basket beside you” Lord Sterling said to her as I came up taking his spit-wet hardness out of my mouth and seeing her smiling as she made her way over, the retrieved tube of bum-lube in her hand and leaving me thinking… “Oh God! This is it!”

My stomach turned as I trembled, not so much in fear but with the build up and all of the anticipation… And now here we were…Ready to cross that final line… My own personal, private gay-line…

“Mmm okay! Oh I love playing with butt-plugs, here let me help you Dana… Are you all numb from the pepper? I bet that was hard to get used to huh?” Veronica asked sounding rather gleeful as she had me gasping, reaching up and taking hold of the butt-plug residing up my backside, and where pushing in instead of pulling, she had me calling out in pain and not with the relief I was looking for…

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