Dana-boy Ch. 01

"Hey... You'll do as we tell you, do you hear me?" He barked at me again... "Vee and I will be spending some time alone down there, or we'll want to, now that we're trying to have a baby, and were only thinking of you Dana... You worry too much man"

Sounding pissed again, this time for being ungrateful as I shied away some and continued, then, wanting appease him by taking him back into my mouth...

"Yeah that's good, all the way" Brother Reg sighed then as I opened up and took most of his still kind of soft but rapidly filling member in as far as I could, knowing he likes it when I throat him, going down until I can feel his pubes tickling my nose and holding on as long as I could before the gagging set in...

"My friend, Lord Sterling, he's in his early 50's I'd say,,, Oh and he's completely 100% gay, but not that there's anything wrong with that...I mean, Dana? You did tell us that you want to have sex with men didn't you?" Brother Reg asked while telling me how things were going to be down in the Islands and to be honest, I had sort of expected something like this...

Plus how I could deny what he was asking when he had himself tonsil deep in my throat?

I mean, with Veronica and Brother Reg wanting some alone-time while we're away. It wasn't something that had been discussed or talked about, but I did wonder because well... Even I could see that it made sense... Sort of...

What I hadn't thought of was telling them all that I wanted to have sex with men, or a-man... Because as far as I could remember, I hadn't... Or at least not with all of them...

"B-But I never said that... I... I only said that to Mom" I answered looking to her as she sat there with Veronica and looking at me, she looked like she was guilty of something... Yeah, guilty of ratting me out is what...

"Mom?" I asked looking to her but knowing already that she had betrayed me...

"Well, I'm sorry Dana-girl, we were talking while you were gone, and I was telling them about your night with me, and how you said that you do want to spend some time down there with a man, and I for one think it's a wonderful that you'll have someone while these two are off having their own kind of fun"

Shocked now and knowing that I was being set up behind my back where it looked like it had been prearranged and decided that I would be shacking up with this rich old guy with a weird pretentious sounding name, while Veronica and Brother Reg went off on their own to make a baby.

Hearing them, or my Mom that is, I felt myself starting to well up, ready to cry as I sat back on my heels, naked and feeling betrayed with Brother Reg's semi-hard cock in my hand, I felt alone and ganged up... Bursting into tears, I rose up and rushed out of the room crying, afraid, and not wanting any of this...

My emotions were being heightened by the hormones of course, and it was getting the better of me. So instead of finishing what I was doing, cleaning and fluffing Brother Reg, I bolted, heading for the stairs I ran for the safety of our bedroom...

"Oh Dana! Don't be like that, come back baby, we all love you! That's why were doing this" Veronica called up after me as I ran, naked with my caged little dick flopping and jumping around in front of me as I hurried up the stairs. I was too upset to turn back or to even listen I needed to be alone... I needed to think and cry, feel sorry myself and how I'd let all of this get away from me... I felt desperate without any control, and it felt like running away, staying or going, it was the only thing I had any power over, the only thing I was able to choose...

***

An hour later...

"Tap tap tap" I heard, a soft knocking on our bedroom door with it opening then and it was Veronica, coming up to check on me as I stayed where I was, face down on my side of the bed where I'd been crying into my pillow, wondering about everything... Me, the hormones, having sex with men, and also, giving Veronica away like I had...

When I thought about it all at once it was too much to bear, but with Veronica coming in and sitting beside me, speaking softly, in a few minutes she was helping me, showing me that not all was bad, and that I was looking at this the wrong way...

"Hi baby... Are you okay? We decided to leave you alone for a while, I guess things were getting a little too intense for you were they?" She asked, coming in and sitting down beside me with her hand resting on my back as I lay with my head turned, looking to her and seeing she was dressed now, or in a robe anyway and wearing regular panties, probably trying to keep Brother Reg's baby-making sperm deep inside of her...

"N-no... No I'm not okay Vee... I'm really scared... I feel like you're trying to get rid of me and that I've lost you to him for good... Are, are you going to want a divorce?" I asked thinking this was the next logical solutions, believing now that she and Brother Reg would want to carry on together without me...

But honestly, I didn't know what to think... What with how they were talking and Brother Reg himself saying they were trying for a baby, not just wanting to get her pregnant for 'us' meaning Veronica and I...but instead the way he sounded, it was like 'they' were a real couple and I was getting in the way, hence their wanting to hook me up with this older man who was my Mom's age and had lived in the Islands his entire life, but really he's British...

'Lord Sterling' as Brother Reg called him... Explaining who this guy was, and that he's already spoken to him about me, which was something else I was having a hard time getting my head around...

I mean it was one thing admitting to my Mom that yes, I did want to have full-on-gay sex with someone, sometime... But never had I expressed an interest in having a boyfriend or even being set up, on like a date even... But not this... Not knowing ahead of time that we were going to be staying with this man, Lord Sterling in his own private villa... It was all so confusing and quite frankly, it was also rather scary...

"What? No... Don't be ridiculous, I don't want a divorce and neither do you" Veronica began putting down my silly notion... "We're staying married no matter how things turn out, but that's the problem baby... You're thinking too far ahead and getting yourself worked up over things that will probably never happen" She added,, reasoning with me and sounding surprised that I would think such a thing, believing she was going to leave me for Brother Reg...

"Now come, why don't we get you cleaned up and you can come back down stairs? I promise you, no one is going to be making any more fun, and besides, this is suppose to be a happy time... We're leaving in two days, and we won't be seeing your Mom for another month... So come on, lets get you fixed up and into something pretty, come and join the celebration Dana-girl... You're missing out and we all want you come down and be with us"

Feeling better, but still rather reluctant, I let Veronica lead me into the bathroom where I jumped into a quick shower, washing away the mess my make-up had become, what with all of the crying and starting off fresh, when I came back, she was still there waiting for me with some clothes for me to wear... More of her old clothes of course...

"There you are now, my pretty husband... See? I love this about you baby and it's also why I'll never leave you... It's so amazing to have a guy like you, someone who I can not only talk to about, you know? Stuff that girl's talk about, like guys and relationships, and sex"...

..."But also, I get to play dress up with you anytime I want! It's like I have my own living breathing Barbie doll..!" Veronica said to me as I came back in with her there waiting in our bedroom, ready to help me dress and telling me again how much she prefers me like this... Being her own living, breathing dress-up doll as well as her submissive cuckold, and rather gay husband.

But the bulk of what she was saying? It sure didn't make me feel all that much better... Or not at first...

"S-so... That's how you look at me now? As just your girly-toy?" I asked feeling a bit solemn with how I believed she was seeing me. Like I was indeed just a toy, something to be taken out of the closet and played with when the mood struck...

"Aww... No baby... You're misunderstanding me again" She replied but then hesitated as she thought about what she was going to say... "I think... No, what I mean is... Now that Brother Reg is here, with us, you know? As the man in our relationship? Which I will admit, it is strange and oh God, I'm afraid to tell my sister."

..."She'll lose it for sure and disown the lot of us, but I don't care about her" Veronica went on but getting herself side tracked and mentioning her sister Sandra, I too was left a little wide eyed and feeling even more afraid...

"But what I mean Dana, is that I want this to work for us...and even if you do discover that you umm... That you do prefer men, let's say? Even then, I still want to be married to you... I want us to raise a family together, and sure, before you ask or roll you eyes saying something sarcastic, because I know we're not what anyone would call 'traditional' but again...I don't care what people think... I only know what I feel...and I know that I love you... That's what I feel... Isn't that enough for you Dana?" She ended there after going on with her speech, and as always... She was right...

I did love Veronica unconditionally, which is what she was saying, that in essence, and no matter if we are different, we will always love each other... Even if I do end up coming out completely, wanting to be with a man... It wasn't hard to imagine really, or not with a truck load of female hormones raging through me, a lot of my impossibles were become the opposite....They were becoming very possible, and very fast...

I guess it was because I hadn't really thought of it or considered that side of things... Becoming more female, or even just feminine... I hadn't counted on this including my seeking and wanting a relationship with a man... I thought I was fine with just being who I currently was... A closeted, chastised, panty-wearing sissy...

***

"There! See? You look all nice and pretty for me again, you look so cute in a dress by the way, and the stockings? Oh my God do you ever have the legs for them!" Veronica said then, buttering me up as she zipped me into yet one more of her older dresses.

It was another, pretty dress she had found in the back of her closet that was short enough with an open, long v-neck in front with puffy quarter-length sleeves all trimmed in white lace. The dress itself being medium-blue in colour with little white daisies scattered all along the lower half... It was pretty and very feminine, making me blush but I loved how it felt on me, moving and caressing my nylon clad thighs underneath.

Zipping me in and adding my new favourite, my long string of faux pearls, double strung around my neck and with my make-up fixed I looked somewhat presentable again with Veronica telling me to use more powder, wanting to give me that 'fresh-faced' look as opposed to the heavier amounts of eyeliner I had been using.

With just a smattering of mascara on my lashes to darken them up, but forgoing much of anything else, save for my coral-pink coloured lip gloss that Veronica happily applied for me, smiling and telling me how much I looked liked like a real girl again, and giving me that same quaking, sinking feeling... But as well... It was always followed by a certain other type of twinge... The one forming in my mind and also in my little dickie as it strained, trying in vein to grow while living trapped in his little pink plastic cage...

This certain twinge of arousal... It also had me wondering now just who Lord Sterling was... And also? What was he going to be like?

Yes, I had to admit, being terrified and feeling like I had no say in anything, including who I date... The thought and the idea of a man, a rich man who lives in paradise, a completely out and gay man who wants to meet me? I'd be lying if I didn't say that I was scared to death, but also, at the same time? I felt an uneasy excitement growing within me, one I knew I wouldn't be able to ignore as I thought more about him and hours drew us closer...

"Okay are you ready to come back down? We promise we won't tease you as bad" Veronica asked but also she had me thinking... "As bad? What does that mean?" I asked... "You're all still going to tease me? Just not as much?" I added feeling slightly guarded again but with a playful frown coming from Veronica, I knew that wasn't what she had meant...

"Oh come now, you know there will always be a teasing element to this, that's what makes it exciting remember? Now let's go, we've kept dinner for you, and I'm sure you're hungry because after the work out Brother Reg has given me today? I'm starving! Plus I'm excited as all hell... Just think! In two days we'll be there! Basking ourselves in the warm sunshine, laying out on perfectly white beaches... Ooooh! I can't wait!"

Continuing as she had me at the elbow, leading me out of our bedroom and over to the stairs while distracting me, telling me how we'll be out of the cold Canadian winter and into the hot Sun of the Caribbean in just two short days, and I had to say... With the way Veronica was painting the picture? I couldn't wait to get the either...

***

"Oh there's my pretty girl! My don't you look all fresh and cleaned up! I love that dress on you and the cute little sash belt, and do you ever look good in stockings!" Mom gushed saying pretty much the same as Veronica had as I came down behind her feeling shy and blushing as Mom played it up a little too much, but I knew she was just trying to make me feel good...

"Doesn't she Veronica? Such great legs for a girly-boy" she went on, but sort of talking again like she was before I stormed off, I was a little surprised... However I stayed this time, taking what she was saying in stride, or I was trying to at least... Even if Mom did just refer to me as a girly-boy...

"I'm not so sure this Lord Sterling will be interested though, I thought you said he was a gay man Brother Reg?" Mom went on then questioning why a gay man wouldn't want a guy who was doing everything he could be a girl?...and I had to say... With her asking? I wondered myself... Why would this older English gay-man want a femmy, girly-sissy like me?

"Oh don't worry, Dana-girl is just the type of guy Lord Sterling likes, trust me, he's gonna love you" Brother Reg answered both making me feel better and as well, not so much either, thinking again that I'm not going to have much of a choice in being with this man... The one with the royal, entitled sounding name... Lord Sterling...

Which if you ask me, his name, it was a bit pretensions, calling himself a Lord... I mean who did he think he was? Darth Vader's half brother no one ever talks about is probably who, or that's what his named sounded like to me... But of course, I knew enough to keep my snide, sarcastic comments to myself while still feeling the outcome of over stepping my mark with Brother Reg earlier in the evening.

Having our meal then, which was just some take out food, we all sat around in the living room with Brother Reg telling us more about where we'll be staying and what we'll be doing as far as work and what not, seeing how this is suppose to be a working holiday of sorts...

"We don't have to actually do anything until sometime in the New Year, and that's only if our cash flow is running low, which I don't see being a problem... But if it comes down to it, we can all work one of the resorts... I'll being doing some stand up already, but like I said, for the most part we can just kick back and chill... Oh and you're going to love the island we're staying on, it has a great nude beach policy, and wait until you see the house Lord Sterling lives in... His private beach goes around the whole Island!"

Listening to Brother Reg, it sounded like we were going to be staying in this Lord Sterling's house rather than like in a hotel or in a resort with separate little cabins like I was picturing, but as of yet, Brother Reg hadn't mentioned anything more about Veronica and himself going away as he was telling me before, saying they would want some alone-time where I would be left behind...

Having wine and beers during and after dinner, I wasn't feeling so bad anymore but Mom, obviously feeling no pain and having missed out on... Ahem... Sampling Brother Reg's big cock earlier, after my upset had me running away in tears.

But by now however, and with a sneaky, sly smile coming to her lips she stood then, grinning like crazy as she opened and dropped the long dressing robe she'd been wearing, revealing once again her aged, naked and yet still held-together 50-year-old body... Her small titties with her hard, dark and thick looking nipples coming out into the open air along with the rest of her...

"Mmmm... That food sure hit the spot, but now... Now I know just what I want for desert" She said then, arching her back further, revealing and showing Brother Reg her naked body, with her hips tilted forward and her chest thrust out, offering herself to him as he sat back with Veronica on the couch, both smiling and surprised as I was, but none the less, ready and willing to let my Mom do as she pleased.

Stepping in front of Brother Reg, she knelt down smiling brightly as she ran her hands up his strong, muscular thighs parting his own robe, baring him and his big, thick cock, exposed and sitting semi-limp between his parted legs...

"Oh yes Ma'am! You have to try Brother's Reg's special desert!" Veronica added, smiling and joining in... "Here, let me help you... We can share and get him ready!" She continued following my Mom's lead, sliding down off of the couch and kneeling beside her, the two of them about to do what was essentially my job, fluffing and getting Brother Reg's big cock ready to fuck my Mom this time... Instead of my wife...

"Ohhh yeah girl's that's nice... Uhhh... Hey Dana-girl, looks like you get as free pass this time, but don't worry, Lord Sterling will take good care of you in that department... Oh yeah... Page baby.... Or Mommy-slut... Fuck you are a naughty one huh? You love cock just as much as Dana... I can see where he gets it now!" Brother Reg said then, mentioning and talking about me, comparing my Mom's love of cock to my own as both she Veronica began to lick and suck him in earnest.

Together they were down there, getting him wet with their combined spit, and Mom, becoming so enthralled and turned on she went lower, licking, tasting and sucking at his big, hanging balls as his relaxed back, closing his eyes in delight, placing a hand to each of their heads, stroking their hair as they sucked his cock together... Looking like a King... Our Brother Reg was sitting on his throne with his two whores on their knees... Sucking his cock and taking care of his needs...

"Ohhh fuck! I love having two chicks give me head, it feels so fucking amazing... But hey Dana-girl, don't sweat it too much, you'll see, Sterling's a really nice guy, charming as all hell, and he's rich too, so if I'm not careful, he might steal all three of you ladies from me!" He joked looking to me as the two woman, my wife and my Mom, they were feverishly licking. sucking and slurping at his thick cock...

"But... Uhhhh... If you don't make me cum sucking me? I'm about ready to tap that hot, mature little Slut-Mamma pussy... How about it Page? Ready to become another one of my bitches? You wanna ride this big fucking thing?" Brother Reg added, turning his attention from me to my Mom, clutching roughly at her hair and prying her head back to look at him, listening and hearing him ask if she was ready, if she wanted her tiny, mature Mom-pussy fucked...