Dana-boy Ch. 02

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The trouble in finding Paradise.
13.6k words
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Part 2 of the 5 part series

Updated 06/11/2023
Created 12/30/2021
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(Author's note... This chapter may contain elements of a bisexual nature)

The trouble in getting to Paradise...

After fucking my Mom hard, taking her from behind and making her scream like an animal, Brother Reg came inside of her, shooting and dumping his second load in as just as many hours, which was much less substantial, and it took him a lot longer in getting there, much to my Mother's delight of course...

"Oh that was sooo good... I haven't been fuck like that, ever... Th-thank you Brother Reg... Mmmm... You can have me anytime you want" Mom groaned out of breath at the end as Brother Reg slipped his spent cock from her well fucked pussy, and turning to me with a look, he needed no words in telling me what I was to do...

Moving from my perch where I'd been resting on my collapsed knees, leisurely licking Veronica's pussy for her, more so tending to her rather than getting her off, I centred myself in front of Brother Reg and his somewhat deflated, long, thick hanging member...

"Uhhh" I moaned softly as none of us spoke, just Brother Reg, sighing along with me, even he was exhausted now having gone two rounds in one evening...

"Oh yeah Dana-bitch, do your girly thing... Clean your Mom's pussy stink off of me" He said to me in a quiet voice with no sound of derision, but his words they were enough, telling me what I was doing, and just who's pussy I was cleaning him of, getting rid of my Mom's stink as he put it, but I don't think he was being mean... No, he was just being Brother Reg...

He was our leader now, or more so than ever it seemed, what with Veronica and him actively trying to make her pregnant, and with my Mom joining our fold, it appeared we were forming our own little commune or cult.... Creating a new religion where all three of us would worship under our patron and guiding light... Our Brother Reg...

Of course, I'm over dramatizing the whole religious thing, although at the time, I was on my knees paying homage to him, taking his sacrament if you will... The offer of licking and cleaning his pillar of our devotion... Brother Reg's semi-hard, long hanging, 8-inch cock that had just finished fucking my Mom and thus completing our little 4-way circle...

So, in a way, you could say there was an aspect of faith, or a religious bent in the way we were doing things... Or, it sure did feel that way...

***

A few days later...

"Bweeep! Boop! Boop! Bweeep!"

That was the sound I heard at around 11am, and no it wasn't a late alarm clock waking me up, but it was something that was indeed quite alarming just the same...

I wasn't sleeping and dreaming but rather we were at the airport and I was about to face a very real and wide-awake nightmare of a whole different kind...

***

"Step over here please... You'll have to go through secondary screening, pick up your bags and follow me"

Listening to the Customs agent I could hardly believe the woman as my face turned white with terror, I looked back to Veronica, who appearing just as surprised as me she shrugged her shoulder as if to say she didn't know either...

The three of us were in line at the security check-point preparing to board our flight, and with me being the first to place my carry-on bag up onto the conveyor and step through the metal detectors, it seemed something on me was setting everything off...

"W-what? I... I don't have anything metal on me... I don't even have any pockets to carry anything" I cried, surprised and trying to reason with the large female Customs agent as I stood there looking back through the arch-way to Veronica and Brother Reg behind her, who as I noticed he wasn't looking very happy, being held up because of me...

"Bweeep! Bwoop! Bwoop!"

"Oh yeah? Well what's that then? Do you have any prosthetic limbs or metal implants?" The big woman in uniform asked as she waved her hand held wand over my front area where in a stomach turning flash it dawned on me why I was setting off the metal detectors...

"Oh... Oh God no... I... I forgot" was all I could offer or say as I felt all of the blood draining from my face, going pale and feeling light headed, I thought for sure I was about to pass out...

"You forgot what Sir? Oh wait... I think I know" The woman replied, looking at me suspiciously at first but then waving her wand again and getting the same beeping result she looked to me smiling as she leaned in asking, saying to me...

"By the looks of you honey, I'm going to guess that you're not wearing a prosthetic and it's your chastity devise that keeps setting off my equipment... Would that be correct?... Sir?" She asked, pausing and with her voice down low, trying to save me some embarrassment I presume...

But calling me 'Sir' at the end, she sounded kind of sarcastic like she wasn't sure and I didn't blame her, what with how I was dressed and with eye make-up on me no less...

But with what she said to me next? She wasn't helping me any either...

Embarrassed beyond belief and nodding a soft, wordless "Yes" and near enough to tears, the woman smiled at me as she hooked her arm in mine, leading me away and saying... "Okay, don't worry sweetie, you're not my first. But I still need to see it because you've admitted to carrying a concealed item, so... I'm obligated to check... Now come with me, the exam room is just through here"

"B-but... You... You don't understand... It's j-just a little pad lock... I'm not hiding anything" I said to her pleading and trying to reason with her but even I knew it wasn't going to work as she led me away, opening a white frosted glass door as I heard Veronica from behind me calling out...

"It's okay Dana, we'll catch up to you in the departures lounge, do whatever she says" I heard her say but with no time to turn and look, I was soon alone in a small exam room with this Customs agent woman where I thought this was not okay... In fact, this was far, far from okay...

"Alright sweetie... Let's get those cute little shorts down, I'm surprised you're wearing something so skimpy, don't you know it's winter outside?" She asked as I stood in the room with her, terrified and quite surprised with how she was talking to me...

"Ver-Veronica... She said I should wear shorts because it's hot where we're going, and we only went from the car into the terminal, so..." I answered while nervously popping the top button on the tiny pair of cream coloured, tailored shorts with a turned cuff showing off my shaved legs as Veronica also wanted.

Resting higher up om my thighs, and with no pockets, the tight, smooth fronted poly-cotton blended pair of shorts hugged my every curve. Yet with the cut of the material being for a female, the gusset, or the crotch was doing a good enough job keeping everything out of sight and without much of a visible 'bump' where even my cage was hard to see...

Hell, from the way I looked? You would be hard pressed to know that I was even a guy from the waist down...

Wearing light eye make-up, again at Veronica's insistence, even when I balked but she talked me into doing my lashes as well as dusting my cheek bones with rouge "To give you some colour" as she had said to me earlier that morning, all smiling and happy that we were on our way.

Wanting to forget how I looked and not to mention matching my face to my passport photo, I kept my head down in the terminal but with a good look it was easy to see that I was trans-gender, or whatever you want to call me...

But now? Forgetting I had that damned brass and steel pad lock keeping my caged little dick locked up nice and tight? Suddenly my appearance didn't matter all that much any more...

"Umm-Humm" said the Customs lady with 'Gladys' stamped into her name tag as she hummed out her reply. Sounding board and like she had heard this same story a hundred times before... Or maybe not a that many, but she sure seemed used to this...

"Like I said baby, you ain't my first sissy... The little blond bomb shell behind you in line? She's probably your wife, and the dream-boat with the dreadlocks is her Bull... And that makes you her little sissy-cuck husband... Am I right so far sweetie?"

Standing and looking shocked with the top of my pants open, I was stunned with how easily this woman had me pegged, or all of us for that matter... I was left speechless with my mouth slung open as she smiled, knowing she was right...

"H-how? How did you know? Is it that obvious? Or are you just really good at your job?" I asked with a stutter as she kept smiling, standing there in front of me with her hands on her hips but as happy as she appeared, she also looked like she was growing a bit impatient...

"Uhh! What..? What are you do-doing?" I cried as she stepped to me, surprising me and taking matters into her own hands as I suddenly found myself with my little shorts and panties pulled down at the same time, the two left sitting in a bunch at the tops of my thighs...

"There! I knew I was right... You are all locked up aren't you? Move your hands baby, let me see" She said to me after stripping me and then taking a step back...

"And yes... I am good at my job... But I tell you... I knew the second I saw you sweet girl... I could tell... I am an expert, but just between you and me baby?...and don't tell anyone but I would l-looove to take you home and watch my husband fuck you" She said to me, leaving me looking to her stunned and with my mouth falling open yet again...

"Mmm... Oh, yeah... I know this part ain't appropriate, but luckily we're not allowed to film in here, so come on baby-boy, give Mamma a little sugar before I let you go on your cucky honey-moon" She added, smiling now with her arms open...

"You? You wh-what?" was all I could manage as this big black woman, this female Customs agent who had me stripped from the waist down, exposing and showing her my caged little dick... She pulled me to her and all but enveloped me in her arms, leaving me surprised as well as gasping in a cloud of her strong scented perfume...

"Uhh! Ummph!" I moaned feeling like she was going to break my spine, she was so strong and I didn't know what to think, much less what I was suppose to do as my face landed in the pillowy soft, warm skin of her big breasts. The open buttons of her uniform shirt allowing my cheeks to touch her dark, creamy skin, and I swear... If I wasn't so shocked and dismayed with what was happening? I would have other wise enjoyed what she was doing!

Her perfume, although heady and overbearing, it was also intoxicating, the added pheromones triggering something in my brain, as was the warmth and feel of her lovely dark, chocolatey coloured skin... Not to mention my face being pressed into her wonderful big black titties!

But then, gasping and with my eyes flying wide open I looked up to her smiling when shocked even further with what she did next...

"M-Ma'am! You're... You're touching my bum!" I sighed aloud while trying to be quiet yet I was so shocked with what this woman was doing, I could hardly believe it... Feeling her grabbing my bare ass and mauling my little white cheeks as she kept me there and held me close, I didn't know what else to say, or do!

"Umm-Humm! And what a cute little sissy ass at that... But okay sweetie, I've had my fun... You can hide you're little white boy dick again, but if I can say? I think you look beautiful, and whatever that hot-wife of yours is doing? She's doing it right... Now go on sissy before I lose control of myself again and start spankin' that cute little tushy"

Letting me go, Gladys, she was all smiles and lovey-dovey after that, leaning back on the wall mounted table with her arms folded under her huge bra encased tits, smiling and watching me as I clamoured, hurriedly pulling up my shorts...

"Okay bye! I'd give you my number but it's not allowed...You go have a good vacation honey, and if I were you? I'd be down there sucking and fucking as much Island dick as I could while I was there.... Say? How long you going for baby-boy?" She asked as I was making my way out, ready to rejoin Veronica and Brother Reg, but stopping me I turned and told her with a sly smile that we didn't have to came back, not if we didn't want to...

That made her smile and whistle while also leaving me thinking that no matter how humiliating and embarrassing this had been, in the end she had made me feel good about myself and feeling like I was wanted...and I didn't mind her molesting me all that much either because she smelled really good and I loved her soft dark skin...

Or I should say that I didn't mind so much... Now that I was free to go!

***

At the departure lounge...

"Oh good! So they didn't arrest you for having a concealed weapon?" Veronica joked as I made my way over to where she and Brother Reg were seated outside of our gate...

"Ha-ha... Very funny, and no I wasn't arrested, but I had to show that big black woman my chastity cage, even though she told me she knew already... It was so embarrassing at first, she said she could see that I was your sissy cuckold, and that Brother Reg was your boyfriend or like Mom also said, he's your Bull" I answered sitting down in an empty seat with Brother Reg looking like he was about to burst out laughing...

"Call me what you like Dana-girl... We all know what you are, even the Customs people! Tell me? Did she make you give her any sugar?" Brother Reg asked, commenting and getting it right, like he knew something I didn't and gasping, my eyes shot open in surprise...

"Ye-yeah! She did!... How did you know that? She made me hug her and pressed my face between her tits, but then she grabbed my bare ass and... Oh God this is the embarrassing part, she said she wanted to take me home and watch...She wanted to watch her husband f-fuck me" I replied using a low a voice, merely mouthing the words 'fuck-me' with so many people around...

"Pffftt! Ha-ha! That's gas man" Brother Reg guffawed, laughing as he explained then, telling us both how he knows these things...

"I know because all big chicks like her are they same, and especially so down in the Islands... They love fucking with little white dudes, and little white girls for that matter... So, you'd better watch yourself too Vee... It's not just Dana-girl we need to keep an eye on!" He said joking and laughing at my story but also issuing Veronica the same warning... Telling her she needs to beware of big black Island woman who apparently, they love playing with little white women and not just their femmy, cuckold husbands!

"Oh I don't think I'll need to worry too much... Not with you as my protector Brother Reg... However, if you wanted me to go with a big beautiful black lady down there? I'll do it! No problem! I loved making out and even going down on Page, or 'Slut-Mommy' as you like to call her" Veronica replied, giggling herself and telling Brother Reg how she would have no problem sleeping with another woman, especially after experiencing her first taste of sapphic-love with my Mom, and being quite descriptive while she was at it...

Speaking of Mom, that was a sad good-bye to say the least... She had dropped us off at the Airport with a lot of hugs, kisses and tears all around as we parted ways and with all three of us feeling bad for leaving her behind...

Staying home was her choice... But now though, with things the way they were. How they had progressed, with her joining us in our three-way polyamorous relationship, and essentially making us this strange and bizarre kind of incestuous-four-some... I knew that she was regretting her decision in feeling she needed to hang on to her old life back home for whatever reason.

Yet, as bitter sweet as our farewell was, it did however come with the continued promise of her flying down just before Christmas where she planned on staying until sometime into the New Year, which I was already looking forward to... I mean as far as she liked pushing me these days, even being mean and mocking me sometimes, she was still my Mom and I did want her close to us...

***

Some four hours later...

"Oh Wow! It's soooo hot here! Can you feel that Dana-girl? Aren't you glad I put you in shorts this morning?" Veronica chimed as we stepped off the airplane and out into the hot and very humid feeling air, and what with this being a smaller airport, there were no jet-ways taking us indoors, just the little roll up stairs, leading us down and onto the even hotter tarmac...

"Oh gosh! You're right! We can say good-bye to Canadian winters! Whoosh! It is hot!" I answered, feeling good and loving the heat... I was never...and I mean never a fan of cold weather...

Even being a kid growing up in Canada, I was more likely to be found in my room with a colouring book or plopped down in front of the TV in a warm, comfy pair of wool socks, much more so than you would find me outside, freezing half to death in a pair of skates on some frozen pond and playing hockey for hours on end... Canadian or not... That just wasn't me... I'm a more of 'Whiner' than I am a 'Wayner'... But I'm sure only a Canadian will get that...

Anyway... I digress...

Having arrived and now out of the airplane with the hot Caribbean Sun spilling down on top of us, we were hit with a wave of heat I hadn't felt in some time... Don't get me wrong, it was wonderful and I loved it, but boy! Was it ever hot, yet it felt good...and so did the two rum cocktails I'd had on the flight... They were making me love it all even more!

"Don't worry Dana-girl, you won't feel hot for long, we still have another hour of travel ahead of us before we reach our island, but this time it's in a boat" Brother Reg added, telling us we still had some ways to go before we're on 'our' Island as he put it...

This was another surprise to me, or well, not that I had really thought about which Island we would end up on, because it's not like I was familiar with the place, but still... I wasn't expecting us to be taking a boat after our long four-hour flight...

"Oh gosh! A boat? Okay... I didn't know we were going to be so far out there!" I said back as we gathered our bags and headed out towards a waiting taxi, one that would take us on a short drive down to a stunning looking little marina filled with sailboats, restaurants, peers and people everywhere out enjoying life in the bright Caribbean sunshine.

Reaching the end of a dock we all climbed into what turned out to be another kind of taxi that was actually a long, wooden, open top boat with a canopy section near the back and being driven by a smiling Islander who didn't say much, he just grinned and nodded a lot after Brother Reg said something to him into his ear while palming him some money...

"Okay were all set! This takes about an hour like I said, so let's sit back and enjoy...and see? Didn't I tell you it's much cooler down here by the water?" Brother Reg said as we all settled in with the skinny boat operator untying us and then starting the outboard before steering out into the open water...

"Yes it is much nicer down here, but I want to get in the mood, you sure he said it was okay?" Veronica asked Brother Reg as the two of them sat side by side under the canopy area in front of the guy driving with me then left out in the Sun, sitting alone near the boat's bow and faced back towards them.

But saying something to Brother Reg, I wasn't sure what Veronica had meant... What mood?...and was what okay?

"Yeah it's fine... Go right ahead, and tell Dana-girl too" Brother Reg replied as I looked to the pair of them, not sure what was going on until, Veronica, shocking me some, she sat forward in her seat, wobbling a little in the moving boat but none the less she lifted her top up and completely off where she handed it to Brother Reg before reaching back to unclip and take off her bra leaving her topless but also leaving me rather speechless...