Dana-boy Ch. 05

Lingering a moment longer in the skinny, old Islanders his arms as Mom looked dreamily over her shoulder she winked at him and giving us the impression that she had tipped him with something else alright... Something other than the local currency...

"Si-Si...! Ee's okay, I enjoy you mucho-mucho Ms. Page, gracias senorita... You tip very, very good si-si - yes?" Philippe replied in his broken and heavily accented English, and shocked a little but if I didn't know any better I'd say they had stopped out in the middle of nowhere on the calm Caribbean waters, and where like us... All three of us, Brother Reg, Veronica and myself, we had a skinny dip just to get us into the mood of being here in the Tropics.

Putting it together from the flush, satisfied look on my Mom's face, and from how the old fella was smiling with his one gold tooth gleaming away in the bright sunshine, I'd say that Philippe instead of staying on board and clothed as he had with us... I'd say this time he stripped of and joined my Mom in her own first taste of the Caribbean...

But as it appeared, Mom was also beaming and looking so happy because she'd just had her first taste of Island-cock!

"Hello, greetings my dear Ms. Page... I'm Lord Sterling, your host... However as with everyone else, you may address me 'Lord'... And I must say, it is a pleasure to finally meet you" Lord Sterling said to my Mom then as he held out a hand to help her out of the boat with me and being the chivalrous English man that he is, gay or not, he kissed my Mom's hand, making her titter and giggle, feeling all special and very welcome indeed...

"Oh my yes! Hello! It's a pleasure to finally meet you Lord Sterling, and believe me you need no introduction, I've been talking to Veronica and she's been telling me all about you, so please umm, my Lord.... The pleasure is all mine"

Replying and smiling from under her big floppy sun hat and her even bigger sunglasses, and looking kind of like Veronica when were first arrived, Mom greeted Lord Sterling with radiance, fawning over him and forever smiling in her tight fitting, thigh-high sundress that dare I say she had nothing on her underneath.

Or not after her boat ride with Philippe, the old but still rather fit looking water taxi driver who as well, he was all smiles and looking like he's was having the best day ever!

"And Dana-girl..! My-My! Look at you! I love your little outfit my baby-boy! White silk short-shorts and that crop top! Wow! You look like you're ready for the Pride Parade back home and not the beach!" She quipped, going a little over the top when commenting on my clothes. Just as I had feared...

Yet pleased none the less, I was glad to hear her sounding so up-beat and enthusiastic, saying I looked more 'gay-parade' in my little outfit and not so much the 'beach-bunny' she had driven to the airport wearing eyeliner, panties, my tailored shorts and perfumed up to my budding little titties...

"Yes Dana-boy has been going through some changes since landing in my clutches, so you'll have me to blame if his dress isn't what you were expecting my dear, but please, do come... We've plenty of time to talk and tell you everything your little boy has been up to, and as a special treat, as a gift to you, later, he and I have agreed to include you in a little ceremony where I would like you to be there with us, as a witness let's say"

"Wow! I am honoured! A witness hmm? That almost sounds like the two of you are getting married? Ha-Ha! I hope Veronica knows!" Mom joked but I for one didn't find her to be all that funny, inferring that Lord Sterling and I were to be married? Gosh! I hoped not!

"I've been speaking with her and she was quite sad to have missed my arrival but she and Brother Reg will be back next week and I have no time limit, so yes please! Lead on Lord Sterling, I'm thrilled to be here and oh my, I'm embarrassed to admit this but already I feel like you're in charge here.... Even if I am Dana-girl's Mother!"

"That's Dana-boy if you please" Lord Sterling corrected, catching Mom of guard I think as she stopped with us about to get into the car and looking to him as Lord Sterling smiled...

"I do apologize my dear but now that Dana-boy has made his commitment to me, and during his stay, with me... He will be referred to as Dana-boy and not 'girl'... I would prefer it if you referred to him this way... If you don't mind"

"Oh! Umm Okay! I don't have a problem with that! And now that you mention it, I have to say... Dana? Or 'Dana-boy'... I need to tell you I'm okay with you coming out as well... Veronica has filled me in on everything and as I told her my only regret was not being there when Lord Sterling took you the first time" Mom responded, sounding supportive as she joined us in the back seat of the car, casually telling me she knows that I've come out as being gay and that she's fine with my decision.

Listening to her and a little surprised but relieved none the less, not having to go through the whole thing again with her... My next worry however was that with the three of us in the back of the small compact car, it was a little cramped to say the least.

That is until Lord Sterling, embarrassingly but rather wilfully he took it upon himself to take me by the waist and sit me up on his lap in order to make room for us all...

"So just to put that worry out of your head" Mom continued as she smiled and gave me a knowing wink that had me blushing further, feeling like a little kid being sat on a relatives lap in the back of the car...

"And as well, about your clothes? I don't care what you wear but I am glad you're staying on the hormones, they'll do you a world of good being a submissive little fag, if you're not going to become a girl that is... Either way, I just happy that you're happy"

Looking to her with my mouth coming open, I couldn't believe how derisive she was sounding, outright calling me a 'fag' which as a word, I wasn't too fond of, I found it mean and not necessary. But with it out there now, I knew where she stood and remembering some of the things she had me doing and saying, her calling me 'a submissive little fag'... It shouldn't have been that much of a shock... But still... It was...

"Th-thanks Mom" was about all I could think to say back as I blushed continually, feeling stupid in Lord Sterling's lap with his arm around me acting like my seat belt as we bumped along the broken half paved road leading back to the estate, Lord Sterling's sprawling beach-front property.

I did feel better, about Mom's attitude towards me becoming more her gay-son than her transvestite-daughter, my worries didn't seem so bad anymore and as we rolled up the big, stone white house as Mom's attention was distracted further... Seeing how gorgeous the place was and staying here with us, she was about to served a big old slice of Paradise...

"Wow! Lord Sterling! This places is stunning! I love how everything is white and perfect and it's so spacious! This is waaaaay more than I expected... Isn't this place incredible Dana? You're so lucky, meeting a rich man and you get to live in the Tropics! Oh Christ on a cracker could I ever get used to this!"

"Ha-Ha" Lord Sterling sounded off, laughing at my Mom's exclamation and seeing her looking so in awe. Pleased, he took it upon himself then to lead her in as we exited the car, his arm going around her shoulder this time instead of mine as I was left to follow, and to be honest but not to sound selfish, however I did feel a pang or jealousy hit me.

Knowing otherwise and that I was just being stupid, because this was my Mom after all, I put it behind me as the two walked away with me indeed being left behind... Yes... Left behind to carry her bags!

***

"Oh you don't say! You did it right there? You took my baby outside in that gazebo? Aww... I'm sorry I wasn't here, but I'm sure it was an intimate moment between the two of you, and would have wanted your privacy" I heard Mom say as I came into the big, open living.

After deciding it would be best if she stayed in the house with us, what with Brother Reg and Veronica away, I put her bags in her room for her, so I didn't hear the whole conversation, but of what I did... I couldn't help but to start blushing and feel embarrassed... And I think I knew why...

"Ah Dana-boy, there you are... Come, join us... I was just pointing out to your Mother the gazebo where I first had you, but I'm sure I don't need to tell you now do I..? I mean after all... You were there" Lord Sterling said to me as I entered and coming in as I had, with the topic at hand I wished I'd lingered a little longer and not heard anything rather than to be where I was now, agreeing and smiling and not knowing what to say as my older gay lover was showing my Mom all about the first place he had me... The first place he fucked me is more like it...

"Yes it was rather intimate but we weren't alone... No, no both Veronica and Brother Reg were with us" Lord Sterling related, continuing he went on to tell my Mom the story...

"It was a family affair and they were both of great assistance with the lovely Veronica there to hold Dana-boy's hand, she was so loving and accepting of your little man... And Brother Reg? Well, he and I gave our young charge here a real taste of it now, didn't we Dana-boy?" He added wanting me to take over telling my Mom the finer details of this certain, and yes quite intimate tale...

"Tell your Mother all about it... Tell her how you were spit-roasted as they say" He said to me as I sort of cowered, feeling shy and not really wanting to add in anything else...

"So it's pussy-free for you huh?" Mom quipped as I went quiet... "Not even my old girl? That's a pity because your tongue-work is remarkable" She said rather mockingly, pointing out how I'm 'pussy-free' and how sad it is that my tongue work will be going to waste, even my going down on her 'old-girl'...

But to be honest, I shouldn't have been so shocked because as I remembered, Mom could be rather harsh when speaking to me these days. Ever since this whole thing with Brother Reg started she had really been pushing the envelope with her teasing... Which in essence I suppose, it was her voicing her opinion and revealing that deeper down, perhaps she was disappointed with me... I mean, why else would she be so off-putting?, and well... Just plain mean?

"Ahhh, yeah it, it was special alright" Was all I could manage as Mom ignored me then, turning back she was more interested in Lord Sterling as they happily continued, talking about my deflowering, or losing my other-virginity...

"Did he tell you that I was the one who had him first?" Mom asked and making me cringe she was being so blunt...

"Or well, at the time I mean, Dana-boy was actually 'Dana-girl' and I popped your pretty little cherry with my strap-on... Didn't I sweetie? Did you tell Lord Sterling all about how I fucked you with my lovely big and very real looking dildo?" She asked, and again I was left speechless, I mean how often do you have a conversation like this with your Mom? The open and frank discussion about how she popped your anal cherry...

Yes this was some fucked up - messed up shit, but even looking back from here, that was my life so far... Fucked-up...

"Indeed, Veronica has been quite forthcoming, letting me in on all of my Dana-boys exploits, which did include her saying that you had been his first" Lord Sterling replied, answering for me but with a slight pause at the end that I picked up on where it sounded to me like he was discounting my Mom's idea that she had taken my anal virginity, because to him? Using a strap-on wasn't the same... And to be honest? I kind of agreed with him...

However there was no way I could say anything because for one I was too terrified just then, being talked about in the third person between them - and secondly... Let's just say that I wasn't too keen on the current topic of discussion... Me being ass-fucked for the first time, with what and by whom...

"I know I don't have real penis or one like yours, which I'm sure is umm, quite substantial... I mean just by looking at you Lord Sterling, I would have to believe that you're umm... You're blessed with your endowment, I'll say to be polite?" Mom added coming back into the conversation, commenting and alluding to Lord Sterling being well hung and smiling back at her, my older companion... He let her know that indeed... She wasn't wrong...

"Yes, yes my dear Ms. Page, I am rather lucky that way... With my endowment as you so eloquently say, and as our Dana-boy here can attest to... However if would it please you, my young lover and I, we have decided that for your benefit, this evening right out here on the beach, he and I will enact a ritual of sorts. Let's call it an initiation, where you will not only see all of me, but as well, you will witness first hand as I further tame him, fuck him and take your boy away, making him mine as you watch on... How does that sound?" He asked with my Mom's eye going wide and accompany by her even bigger smile, loving how dramatic he was making things sound...

"Ooooh! Ummm Oh yes... That sounds wonderful, I can't wait to see my little boy taking a real man's cock! And thank you my Lord, this is such a gift! I mean that for everything as well... Letting us stay here and helping Dana-boy to realize himself... Oh God, I hope you don't mind my saying but my pussy is absolutely swimming right now and I love calling you 'my Lord' I feel like I'm in your control along with my gay little son... Oh gosh, listen to me... I'm still all worked up from my trip, and umm Philippe, he - he was of great help but... Oh I shouldn't say but he, he gave me a good seeing to when we stopped... He's a devil that one is... Umm tell me is he still here? I think I'm a little tired and might need a, umm nap before this evenings festivities kick off... If you don't mine? My lord?"

Seeing Mom was flustered, quite horny and turned on by all of this talk, hearing about what she can expect during her stay, and of this 'initiation' even I wasn't too sure about... But then to hear her capitulating to Lord Sterling, calling him 'my Lord' and saying how much she liked it, with him being in control? I was seeing yet another side to my Mom that I didn't really know existed... This streak of submission coming out of her when in the presence of a man like Lord Sterling.

And even Philippe the water taxi driver, who as she was so forthright in telling us, he had fucked her during their impromptu mid-Ocean skinny-dipping stopover... It seemed my Mom, she too wasn't holding back...

"Yes it appears today is your day Ms. Page, and Philippe is still here... This island is his home... Would you like me to send for him? He can help you to rest as you acclimate yourself... Become used to your surrounding and all that Paradise has to offer" Lord Sterling offered, smiling with a wide sweeping gesture of his hand, pointing to our luscious surrounds and how they can have this effect on people, wanting to get naked and fuck...

"Mmm! Yes please I'd like that very much and I'm not embarrassed to say that I'm also very much looking forward to seeing you tonight as well my Lord... I'm just dying to see you take my boy and fuck him hard, and whatever else you want to do to him... I'm sure that big cock of yours is simply gorgeous! Oh God this is too much for my old heart to take!!... Which way to my room please, and yes my Lord, do send Philippe along as soon as you can!"

Listening to her I almost had to laugh she was so aroused by all of this, and quite frankly? I couldn't blame her...

Going form being her usual derisive self and sounding rather uncaring about me but then with the mention of cock, or 'Island-cock' I suppose I should say, the change in her where in a breath she went from her usual bar-room-brass to subdued-and-submissive...

"Dana-boy, show your Mother to her room and I'll have Philippe sent in to see you... We'll dine at Sunset and then the 'festivities' as you say, they will most certainly kick off" Lord Sterling replied with a smile as I slipped my arm into my Mom's and ushered her further into the house, showing her where the bathrooms were and then on to her room where I left her... Mesmerized with it's size to go along with the stunning beach front view she would wake to each and every morning...

"Oh my Dana, this is all do amazing isn't it? I love being here the air feels so warm and inviting and seeing you with your man, Lord Sterling... Things could have worked out any better, and to think as well, Veronica and Brother Reg will be back soon and if we're lucky, she'll be pregnant! Oh God I don't think I've ever felt as excited!"

"Ye-yeah Mom it is quite the place but take it easy okay?" I said back to her, wanting her to keep her exuberance in check if she could...

"We're here for a while and well, you don't have to do everything all at once" I added as more of a caution, but as well, I did think she was going a little over-board, trying to do everything, or 'everyone' all at once, like Philippe and wanting to do him twice already when she hadn't been on the ground for more than two hours!

"Yes, I know you're right but can you blame me? I mean look at this place and look at you! All dolled up and looking like the only gay in the village, dressed in that little silk suits he has you wearing... He's something else though isn't he? Your Lord Sterling, or I guess I should call him 'Our Lord' now shouldn't I..?"

"Yes, he is umm, captivating I'll say that but I've learned already is to just slow down... Plus it's too hot here to get all worked up and excited, unless you want to go naked like we do most of the time... I know Lord Sterling won't mind and neither will the staff... They just ignore us but I have seen a few of the ladies looking at me and snickering as they smile... You know? With my cage and all?""

"Ohh! That sounds like fun, going au-naturel all day long! But for this performance Lord Sterling has told me about? Where He's going to fuck you on the beach so I can watch? I was planning on wearing my new bathing suit but I think I might just go native as you say and really throw myself into this Island living! Mmm, I love it here so much already!"

Shaking my head all I could was smile and thing "Is she going to like this the whole time?"

***

Several hours later...

After attending to any and all needs pertaining to my Lord and Master, all needs of a non-sexual nature that is, i.e. collecting his clean clothing from the laundries and putting everything away, and then to his private en-suite where it was decided I would be his groomsmen, being sure all of his favourite toiletries were there and at hand for him to use, things like cologne, hair products, his combs and brushes and one particular that he pointed out...

A large silver-backed, Ivory handled brush he described as being a family heirloom, bestowed upon him in his Grandmother's will...

One that she used not only on her long tresses as he described, but also and with a menacing smile, he told me this brush, with it's big, wide and flat backside, it was also used by his old stern, Granny to correct the household Maid, and going on trying to scare me no doubt, he told me of her cries heard through-out the house as the woman would tan her Maid's bottom for stepping out line or breaking anything, even so much as a dish as he was telling me...

"Poor Mary learned many a life lesson through the back of this old antique, lessons I'm sure she hasn't forgotten, and if I were you my little lover boy" He said with an air of caution, waving the big hairbrush in front of me... "I would be wary, because as old as this brush may look? I am more than sure it's capabilities have not been altered... Not in the slightest"