Dana-boy Ch. 02

"Vee! Wh-what are you doing?" I asked in urgency once I'd picked my jaw up from the bottom of the boat with her sitting back down and looking at me, smiling calmly while donning her sunglasses and floppy straw hat...

"It's okay Dana-girl... We're going to a different kind of place... It's clothing optional on our Island... Not all of them are like this one, so that's why we go by boat... The Government is okay with the nudity, but they won't send flights in, plus the Island is too small... It was all Lord Sterling's doing... So come on, get with it, join your wife and let's get naked little man!"

Explaining as he turned back and, saying something to the guy driving who nodding again, he slowed the motor down and then turned it off, bringing us to a coast and leaving us in utter silence, surround by nothing but the calm, clear Caribbean waters...

Too shocked to say anything, all I could do was watch with my mouth hung open as Brother Reg, saying we should all get naked, he then led the charge, standing in the unsteady boat, he striped everything off, his t-shirt and jeans, and then shocking me even further while laughing he all but threw himself over the side, hitting the water with a loud splash as the boat and the rest of us were sent rocking even harder, going back and forth, I grabbed one of the tie-down ropes and hanging on I thought for sure he was going to take us all with him...

"Oh gosh Vee! Is he okay?...and oh no! Not you too?" I said to Veronica, my voice in a near panic as I looked to her not believing Brother Reg had just stripped completely naked before flinging himself into the water... But then, looking to Veronica I was just as surprised to see her doing the same...

Standing she shucked the rest of her clothes, taking off her sunglasses and smiling at me as she jumped over board with Brother Reg, not caring that the guy divining was getting much more than an eye full, seeing her big white tits jiggling as she went overboard diving naked into the clear blue ocean water...

"Vamoose! You swim too eh? Get naked sissy! It's okay go... Swim!" The boat driver said to me in some broken English while waving, saying I should join the other two as I stayed seated near the front with Brother Reg and Veronica both surfacing in the crystal clear waters, smiling and waving, urging me to join them as I think the guy driving the boat was also telling me to do...

"I'm... I'm not getting naked and going in there! Wh-what if there's a shark or something and be-besides, I still have my... I mean I'm still caged remember? I... I don't want this guy to see me naked!"

"Oh don't be such a big baby... Get your clothes off and get in here now or I'll make you walk into Lord Sterling's place with nothing on... Come on, were just having an early dip to cool off and celebrate that we're here...and don't mind Philippe... He doesn't care... He's only paid to drive, so let's go baby nuts, strip off and get in here" Brother Reg said, or warned, threatening that if I didn't get naked he would make me meet Lord Sterling with no clothes at all.

Fearful of being made to do something like this right away, humiliate myself while meeting this man, God knows I was already terrified just thinking of Lord Sterling, the older guy they were trying to set me up with, so reluctantly, with unsteady feet and my back turned away from Philippe the boat driver I stripped off before holding my breath, and my nose, I squinted my eyes while letting myself fall over the edge and into the water I went in without making much of a splash...

"There! You see? Isn't this nice Dana? I love swimming naked... The hot tub back home is great but this!... Oh my God this is so much better" Veronica chirped as I surfaced and waded my way cautiously over to where she and Brother Reg were relaxing and floating with her clinging on to him about ten feet out from the boat...

"Ye-yeah... The water sure is warm, even way out here... But how do you know there aren't any sharks around?" I asked feeling nervous in such deep and open waters, but yes, I was loving the warmth as well as the sunshine, it did feel great surrounding my naked body...

There is a strange comfort swimming naked that I think all of us feel... It's a womb thing, going back to how were started out, floating around inside of our Mothers... It's all we knew for the first nine months of out lives, so when we swim naked, I guess it just feels good, or natural...

"Nah... It's too hot for sharks, they like cooler water... Just relax man... We're here, so enjoy!" Brother Reg replied, reassuring me and telling us that sharks don't like warm water and that I should just enjoy myself. But feeling nervous as I was? I wasn't so inclined to believe him.

Swimming, laughing, and feeling better, I joined in as we played a quick game of tag with Brother Reg starting things off as he dove under the water and came up under Veronica, making her scream and laugh as he lifted her up from underneath and all but tossing her into the boat, but instead, she landed back in the water with a loud splash...

"Okay! I think we should get going, come on little girl, let me help you get back in" Brother Reg said to me as we neared the boats edge and again doing the same as he had with Veronica he went under me some and came up, lifting me but this time I did land in the boat, or he'd heaved my up high enough that I was able to grab on and fling myself back in the rest of the way

Which as I went in naked with my little dick all locked up in my cage, I can't say I was very graceful and I probably looked more like a fresh, pink skinned Canadian salmon flopping around as I clamoured in face first...

"Ha-ha! Caged sissy!" Philippe laughed as I tumbled over the edge with him getting a good look at me and my chastity cage, but then looking and realizing, I was a little mad at Brother Reg because not only was there a set of climbing stairs at the back of the boat, but now after swimming around to that side, he was there with Veronica, helping her up to effortlessly step back in and not like me, the naked fool being tossed over the side...

"Hey! You guys that's not fair! Aww... Never mind" I said then, first putting up a fuss but then thinking, why bother? I know Brother Reg was only messing with me and it was something I should be getting used to by now...

"What? I thought you might like to get back in the quick way, seeing how you're so afraid of sharks... But like you said, never mind, and hey Philippe! Fire up that motor my brother, take us to our new home!" Brother Reg replied smiling as he and Veronica made their way into their seats, both staying naked this time.

Grabbing my safety rope and hanging on, I found my seat as well, not wanting to fall overboard and be left behind... Lost at sea on my first day...

Okay, sure I was over reacting but all of this was so new to me, and now as Philippe did start the boat motor once again and we were on our way, I was filled with a different fear where it wasn't a sea-shark I was worried about catching me and eating me, but rather I was afraid of the land-shark we were on our way to see and stay with...

Holding my safety rope and looking forward with my body turned in my seat it wasn't long before I could see a thin ribbon of land appear on the horizon and as I turned to look back and tell everyone, I was surprised to see that both Brother Reg and Veronica, they had dressed again where I had stayed naked, feeling a little more comfortable seeing how we were all in the nude, but now, that wasn't so much the case...

"Hey! When did you guys get dressed? I want my clothes too!" I said to them as I moved then, making for my small carry-on bag containing everything I owned, including all of my clothing...

"Not so fast Dana-girl... Say please first and tell me you're not going to be freaking out like you did last time when things were getting a little too much for you... I want you behaved around Lord Sterling... Okay?" Brother Reg said then as he beat me to my bag, moving faster and with it closer to him, he grabbed it before I could.

With him holding my every worldly possession and being as naked as I was, but for my little pink cage, of course I was willing to do anything he said, and until he mentioned it? I hadn't even thought of how I had stormed out the other night after things had indeed become a little overwhelming for me... Seeing how he had spanked me in front of both my wife, and my Mom...

"N-no... I'll be good... I kind of know what to expect already, but please, can I have my clothes? It's going to be hard enough meeting Lord Sterling when I'm dressed and I can't image what he'd think of me if I show up naked... So yes, I'll do what ever you want... I do that already, don't I..?" I said back to him pleading while at the same time trying to reason with him, and smiling back at me, he laughed tossing me my bag, which I caught with an "Ummph" sound as it nearly knocked me out of the speeding outboard.

Feeling nervous as the strip of land on the horizon soon became a big island, I felt myself shaking a little but thinking I might show both Brother Reg and Veronica how good, or willing I could be, I unzipped my bag and rummaged around, looking for the bottom half of my tie-died fuchsia coloured bikini and a plain white sleeveless muscle shirt, figuring I might as well show up looking how I thought Lord Sterling might be seeing me already...

As the soft, effeminate gay-boy I'm sure Brother Reg had described me as being...

"Aww, that's nice... I like that you're taking the initiative Dana" Veronica commented, seeing me dress...

"I love how those bottoms fit you, and I know Lord Sterling will be giving you a look or two if you show up in your bikini" Veronica remarked saying I'll be well received donning my bottoms and the loose fitting muscle shirt, but with not much time to reply, Brother Reg was soon cutting in as the boat came nearer, reaching a set of docks...

***

We were here.. We had arrived...

"Look alive folks, land ho! We are officially here!" Brother Reg declared as he jumped out and up onto the long dock to help tie us off with Veronica and I staying seated until the boat was roped off and all tied up...

"Well.. What do you think baby? We're here in paradise, is it everything you've hoped for? It is so far for me!" Veronica asked while also commenting, telling me she was happy with how things were going but her key words in there were 'so-far' meaning I wasn't sure yet because we had only come 'so-far'...and the rest? Well... That we still to been seen, wasn't it?

"Ye-yeah, I'm okay... So-far... But lets see in an hour or so, after we've met him... Lord Sterling I mean" I replied as Veronica she smiled from behind her big sunglasses and wide brimmed straw hat, looking like an excited shiver had just run through her, thinking of us, or me - meeting our host...

"Oooh! This is so exciting, I can't wait to meet him, so I can only imagine what you must be feeling like, about to meet your first man-crush, that is!" She giggled and indeed, looking and acting as excited, but also sounding happy for me, which did concern me some...

"Gosh Vee, do you have to say it like that? I'm really nervous... Are you sure you're okay with this decision I've sort of made? Or, the one my Mom coaxed out of me while umm, doing me with that strap-on of hers?" I said back sounding nervous and still wondering if I was going to lose her all together because of this... Knowing and believing that my Mom and Veronica were right, and that I had openly admitted my want of spending time with a man...

"Yes of course I'm fine with it baby... You know how I feel...and no, we will not be getting a divorce over this... If that's what you're still worried about" She replied, giving me some reassurance, which I did need just then...

"I mean, if you do decide that men are your thing from now on? I'll understand, but even if you do, and you still want to stay married? I'll want that too" Veronica iterated, telling me that if I did want to pursue a full-time relationship with a man, I was free to do so without it affecting our married status.

But listening and hearing what she was saying, it did hurt a little thinking she had considered this outcome already, seeing us splitting us as possibility... Even if that wasn't what she wanted...

"I... I don't want to split up either Vee... I don't know what I'd do without you" I added wanting to let her know that I wasn't thinking in the terms she was suggesting, thinking I might want to be with a man on a permanent basis, instead of her...

"Okay... Well let's not think too far ahead just yet, okay?" She ended off as Brother Reg came back, interrupting our discussion and telling us our next move...

"Clive, or Lord Sterling, he has a car waiting for us... Thanks for the ride Philippe... Dana? Why don't you tip our friend? You have some cash with you right?" Brother Reg said then as he came back, telling us there was a car waiting for us but catching me off guard, he asked me to tip the water taxi driver and leaving me looking, I didn't have any cash on me at all... Veronica had said I wouldn't need any...

"No! I don't have any money... I'm sorry Philippe, I don't know what to say" I answered feeling bad as I looked to the aging, dark skinned man as he smiled at me but with Veronica piping up, she came to my rescue producing a few notes of what I assumed was the local currency...

"Here you go Philippe, and thank you for letting us go for a swim" She said to him as I stepped off then, putting my feet on the dock but feeling even more nervous than ever, I knew that it was only a matter of time now until I was introduced to Lord Sterling... However I didn't want to say anything that might sound like I was complaining, knowing Brother Reg had already spanked me once, I wasn't about to go through that again, and especially here on this Island and in this strange place...

***

It was only a short drive...

"Hello and welcome! I've been expecting you, it's my pleasure to meet you, I'm Lord Sterling and you must be Veronica... Why, you're even more gorgeous than Brother Reg described... But I say darling, with that beautiful white skin of yours, you'll want to cover up with a high SPF... God knows we don't want a stunning creature like you burning up in all of this wonderful Caribbean Sunshine"

With Veronica exiting the car and greeting Lord Sterling first as I was left back sat in my seat not knowing what to think with my heart was beating a million miles per hour by this point as I looked out into the court yard of what I could only assume was his private villa... It looked so big with vast open lawns, and a stone white house to rival all others, it looked like a hotel.

But aside from all of this, our trappings and surroundings, I felt myself tremble looking and seeing Lord Sterling in the flesh for the first time as I sat watching from inside the car, watching and listening as he introduced himself to my wife.

Helping her out and taking her hand he gushed over her in a different sounding sort of accent but it was still quite easy to tell he was British by his charm and manners alone, never mind his smooth sounding voice...

Given just enough time to look him up and down once and then twice as I remained back half hidden inside the car, I was glad to see that he was a good looking man at least, in shape and not the over weight, pervy slob that I had envisioned him being after letting my imagination run away with me...

Picturing this as some horrendous ordeal I had worried plenty, sweating out this very moment a thousand times in my head... My first meeting with Lord Sterling...

"Ah and who do we have hiding in here?" He said then, suddenly turn his attention back to me, reaching in with his out-stretched hand and asking with a smile who I was and why I was hiding, but to be honest, I think he knew. Offering me his hand large, heavily tanned hand I trembled knowing this was it...

After all of the worry and build up, here we were... I could hardly move, let alone think...

"You must be Dana" He said smiling and leaning in wanting to help me out as he had with Veronica but with me feeling incredibly shy and stunned into quiet submission, I reached out placing my smaller hand in his, accepting his offer, letting this distinguished, tanned looking and rather handsome older man help me out of the car...

"It is an absolute pleasure to meet you at last my dear sweet boy... And I do believe Brother Reg was being quite conservative in his description of you" Lord Sterling said to me in what I took as a compliment, but still, I could feel my heart threatening to rip itself from my chest I was shaking so bad, finally meeting him face to face.

Or face to chest was more like it, he was that much taller than me as I looked up to him with his kind looking eyes holding and keeping my attention. I felt so small in his presence, dwarfed by the experience and having literally just met, I felt like I was already under his influence and his control...

"Hel... Hello S-Sir, it's... It's a pleasure to meet you t-too" I stammered back as we all stood there, with Veronica and Brother Reg watching our exchange, smiling and thinking what? I wasn't sure... But I felt embarrassed and like I was meeting a pre-arranged blind-date...

Only in my case, this blind-date was with a man...But I had to admit, Lord Sterling, if anything... He was that... He was all man...

"You are a very, very cute boy... But for now, please, all of you, come in... I'll have your bags brought to your rooms and in the mean time I have cocktails waiting out back by the pool" He added, making me feel even more nervous what with how he was looking at me, and what he was saying, calling me a very-cute-boy with his voice a mix of a British accent combined with a flavouring of the local tongue, it made him sound all that more lyrical, poetic and interesting.

Up until now, Brother Reg hadn't really described Lord Sterling very much in the physical sense, other than to say he was older, in his 50's somewhere and that he's originally from England... But from the look of him, you would think he was a local, what with how he carried himself and moved within his loose fitting clothes, and his dark tanned skin looked incredible.

Like supple, worn leather crafted and tanned from living here in this tropical paradise for so many decades...

Standing an easy 6-feet tall, with broad shoulders and a somewhat hairy chest that matched the sun-bleached a greyish blond hair he had up top on his head. I muttered a hushed "Oh Wow!" in my head but definitely not out loud...

"You have a very beautiful place here Lord Sterling, the grounds are amazing, and I can't wait to get onto that beach!" Veronica commented as we all moved in and sat ourselves around a large outdoor table under a big umbrella that looked out towards the water at the back of his property or his estate you could call it from the size of the place...

"Why thank you my darling... It is nice to live in such divine surrounding. and yes, the beach is quite fantastic, but you'll have no worry about being near the water, because if you look over to your right, the two cabins you see there have been set aside for the three of you... Now you'll not only be living with the sand between your toes, but just about everywhere else as I'm sure you can imagine! Unless any of you would like to come and stay with me in the house, you're more than welcome" Lord Sterling replied, answering Veronica's query.

Yet when he added the part about finding sand 'everywhere else' and 'staying with me' he made sure he had my gaze while smiling and giving me a knowing wink, the kind where I didn't think he wanted the others to see as I felt myself burn, blushing like crazy. I felt like he was hitting on me already...