Dana-boy Ch. 01

Story Info
'Brother Reg'.
13.3k words
4.43
11.6k
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Part 1 of the 5 part series

Updated 06/11/2023
Created 12/30/2021
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Intro...

Hello to everyone who cares to read these intros! I know a good deal of people skip this part and even I can be accused of such, skimming stories to get to the good parts... However, such is life but I have things to say, stuff to tell you about the story, and in this one? OMG did I ever go off the rails so buckle in! This is going to be a bumpy ride!

All kidding aside, this is the 3rd instalment and the continuation of the original story entitled "For Veronica's Sake" The body of this section is themed as GAY MALE, but as well there is a different vibe going on here... And also! Because not all of the sex is gay-sex. I've posted this in the FETISH category knowing it will garner more attention than if placed elsewhere...

Enjoy! -- and if not? Ah well, as the saying goes...

"If the shoe don't fit? -- It probably ain't your shoe!"

Lastly, my utmost thanks to TerryJKM for your help in proofreading and for being my biggest fan, I thank you sincerely... I truly dislike seeing typos and your help has been immeasurable plus your endless encouragement is what keeps me going... Cheers mate, Erin go bragh...

*****

Dana-boy

Chapter One...

'Brother Reg'

It had been nearly two weeks since my visit to Dr. Harper's office with my Mom, where after undergoing some very invasive, and quite painful procedures, ending with two rather large needles containing a cocktail of drugs, sedatives and female hormones being injected into each of my testicles, I was finally allowed to put on my dress before we were handed a prescription and sent on our way.

Following this, or so I was told, after having passed out shortly there after and had to be helped into my Mom's car. I was made to spend the night with her, recuperating as we talked discussing the future, and also, not leaving out her dressing me up again and fucking me with her big strap-on, amongst other thing before the night was over.

Taking me and my anal virginity, or as she liked to believe, taking me while making me confess, my Mom had me admitting that did I want to have full-on gay sex with a man, or 'men' as she also made me correct myself, saying it as a plural, meaning I wanted more than just one man, or men fucking me.

Also, and on top of this Mom had me restate the other thing I had agreed to, which was Brother Reg taking Veronica, and not just as his girlfriend or whatever... But rather taking her and fucking her with a different reason in mind. He was going to fuck Veronica with the intention of knocking her up and getting her pregnant.

And now? Here we were, two days before our departure where we would be leaving the currently and aptly name "Great-White-North" or Canada to those who do not live here... It was mid December and winter was certainly upon us, so with our extended stay in the Caribbean coming up, it was a welcoming thought... Knowing that in few days we would be going from the fridge to the frying pan, or so to speak...

After being sent out for a few last minute things, including a take-out dinner, I came home to find my Mom there and already 'helping Veronica pack' as she had said she would... But the kind of help she was providing when I came in? It had nothing to do with packing our suitcases...

***

"Ohhh God yes! That looks amazing! I can't thank the two of you enough for letting me do this." I heard my Mom say as I came in..."I don't know when I'll get the chance again with you guys all going away, I just hope this is the one - I hope it was me who helped... Oh look at that! Oh God Veronica, that must feel sooo fucking good... Does Brother Reg's big fat cock feel good sliding into that tight little pussy of yours?"

Entering through our side, laundry room door that leads directly into our living room-dining room combo I was stopped dead hearing my Mom and what she was saying... Frozen still in my calf high, black winter boots I stood there with my mouth open and my eyes going wide, surprised more than shocked with what I'd just walked in on...

"W-w-what's going on here?" I asked stammering and standing there looking like a deer in headlights, my eyes fixed across the room to see my Mom sitting behind my wife on our couch...

Or, I should say... My very naked Mother, along with my very naked wife, sitting, spooning together without a stitch of clothing on either of them, as Brother Reg... Oh yes, he was there too, and just as naked he was standing in a crouch, bent at the knee and facing both Veronica and my Mom, who as well as being naked, she was holding Veronica's left leg up at her knee, helping to keep her open and available while with her other hand, she was reaching over to hold and guiding our Brother Reg's long hard cock into the wet looking, parted folds of my wife's eager and waiting pussy...

"Shhh! Don't interrupt, this is important" Mom said to me, and sounding annoyed I must say...

"Your wife and her Bull have agreed to let me be here to watch and help as he tries to impregnate her" She went on, talking over Veronica's shoulder and looking as put out as she sounded, explaining to me what was happening...

"This is the first time her cycle has been right, and it's also the last time I'll be around to participate... So either get out of your clothes and come join us in this celebration of you wife and her Bull creating a new life... Or you can stay dressed as you are in your little skirt, either way Dana, you need to be quiet"

Jumping back after hearing all of that, beginning with my Mom, sounding so dismissive and forceful, and even referring to Brother Reg as being Veronica's Bull which in itself was shocking enough, but to hear her ordering me to be quiet, and as well, telling me to either undress and join them, or basically, I can fuck off... I was a little hurt, thinking I wasn't wanted, or worse... They didn't need me.

Even then, as shocked and stunned as I was coming into this situation, Veronica wasn't happy with me either, or so she also sounded, giving it to me while humiliating me some, mentioning the chastity cage my Mom had sent me home wearing, and was still locked up in at that very moment.

As Mom had predicted, Veronica loved seeing me like this, locked up in my pink plastic cage. But it wasn't just cute and fitting with the rest of me these days, but rather with Brother Reg stepping in as he had? The cage felt like it meant much more.

It was as symbolic as it was useful, setting a crystal clear boundary of where I stood and what I was never capable of in the first place... Which was pleasing Veronica with my smaller than average, meagre 5-inch, reedy thin little dick...

"Yes Dana, please... This is important" Veronica said... "We need you to take this seriously, now do as your Mom says, get naked and join us, show Brother Reg your new cage, I don't think he's seen you wearing it yet"

Nervous now and hesitant, being told to show Brother Reg my little dick looking even smaller, if not non-existent at all, locked up in a chastity device where in a way it was even more humiliating than coming into the house dressed in a short woollen skirt and pantyhose with my parka on over top of the big fuzzy, cable-knit sweater Veronica had also bestowed upon me from her collection of old clothes.

Oh and not to forget my face as well... Made up with liner, and mascara around my eyes and with rouge on my cheeks. I wasn't much for wearing shadows and went with more of the cat-eye look with my eyebrows shaped and my lips left shimmering in my favourite soft pink gloss.

Since the clinic trip with Mom, I had been growing more brave, and somewhat comfortable going out as I was, dressed head to toe in women's clothes... I was 'challenging myself' as Veronica had put it, and boy sometimes, it was just that... It was a huge challenge going out completely en-femme.

But never the less, here I was, dressed in girl's clothing and watching my Mom help my wife get fucked by my best friend, all in the aid of trying to get her pregnant...

Ain't life just grand sometimes?

***

"Okay! Okay! Gosh! I'm sorry, I didn't know this was happening!" I said back sounding frustrated and apologizing but wondering why they were getting so worked up...

"The last thing you told me was to go out and get dinner for all of us, I wasn't expecting to come home to this" I added, speaking to Veronica as I hurried along then, into the kitchen and plopping the shopping bags onto the counter top without much care as I turned then, taking off my coat with my stomach feeling full of butterflies.

I don't know why I always felt like this, scared and like they were all going to laugh at me even though I knew that wasn't going to happen, and that everyone, including Brother Reg, they were all for my dressing and acting like a girl...

It was just me and my damn wall again...

"Ohh yess... Ohhh... I'll never get tired of that feeling... Brother Reg, your cock, it always feels so big" I heard Veronica say as I came back in doffing my sweater and undershirt, a soft blue camisole top but keeping the thin string of small pearls I had taken to wearing most of the time, the long strand doubled around my neck, another gift from Veronica, it was something I found this time while she let me have a rummage around in her vanity drawer full of her fun, fake jewellery.

Going for my skirt next, I was soon down to my pantyhose and pink thong panties underneath, that were indeed mine this time, not borrowed but rather bought with me in mind. And as for the pantyhose? I liked wearing them... They felt so silky and smooth going on but they were also warm like long underwear in winter, and something else Veronica was right about was that pantyhose and leggings did make my ass look incredible, holding and forming me in that just-right sort of way as I walked and moved.

Listening to Veronica moan, her strained sex-filled cries echoing out through our large living space, I turned then, taking a few steps towards them all, mostly naked now and a little afraid to go any further as I remained covered, or my locked-up little dick was, but I was still embarrassed not wanting Brother Reg to see me, even if I had no real reason...

Everything was so out in the open by this point, and knew it shouldn't have mattered, but it did... Stuff like this, showing Brother Reg my chastity cage... It would always make me worry...

"Oh yeah, and I miss your pussy baby... I'll never get tired of stretching you open, but hey? Dana, come here... Aren't you forgetting something?" Brother Reg replied to Veronica's cries telling her how much his cock loves fucking her, which was probably about the same as the rest of him...

Or all of him... Every inch of Brother Reg and his big cock... They both loved fucking Veronica...

But then... With his head coming around, turning to look my way, he called me over and puzzled, I didn't know what I was forgetting...

"Come here girly-man... I know we kinda started without you this time, but remember... You always go first" He said to me as I came in closer, feeling edgy and nervous, dressed in my pantyhose and pearls, and hearing him... I remembered with his help what he wanted... What I was suppose to be doing...

"You know what you need to do... Come here, get down here and do your thing... Suck that cock sissy... That's what you do now isn't it? Gay-boys in dresses, they suck cock?" He said to me sounding quite confident and condescending, telling me that even though the three of them were already at it, with him balls deep into Veronica, I still had to go first... He wanted me down there, fluffing or even just sucking him.

But this again was different, hearing him and with my Mom there... This wasn't just me getting him wet, although the wet part, they were well past, but more so now, this was like my cage, it was a symbol, it was another sign.

My sucking Brother Reg's cock now and in front of my Mom? It was coming with greater meaning...

It was our Brother Reg taking the ultimate lead, having me get down and take him into my mouth as a way of showing my acceptance, and as well, letting him and everyone else see me do it... Sucking his cock... it was my way of giving him my permission, telling him he was free to fuck my wife and that I was their willing sissy. Their permissible gay-boy in a dress as Brother Reg had put it to me this time...

"Ohh yes... I'm dying to see this... I so want to watch you suck a real cock, go on Dana-girl, don't be afraid, don't worry on my behalf... Mommy wants to see her gay-boy suck a big one... Obey your Master, do as he says sweetie" Mom said then, piping up in response.

Becoming dirtier all the time Mom let lose with another of her slur-filled declarations, saying again how she's been dying to see me do this for real... How she had been waiting to see me suck a man's cock... Or as she was saying, wanting me to suck my Master's cock...

Knowing I had no choice, and as well, becoming used to this, or getting there... Slowly... I came around in just my pantyhose and panties underneath. I was relieved in a way, because if there were any small graces, so far, it was that I hadn't been told to strip off the rest of my clothes allowing me to retain some of my modesty for the time being...

Keeping my caged little dick covered for just that much longer as I distracted everyone by falling to my knees beside the couch as near to Brother Reg as I could get and where sat up, with my eyes closed and mouth wide open, I went into surrender-mode. Ready and waiting I offered Brother Reg my open mouth and hoping he would put it in for me.

I wanted him to save me a little this way... Let him fuck my open mouth a few times in front of my gawking and very interested Mother, rather than having me doing my usual as we would start off... Having me nuzzling and kissing his cock with my lips, holding him close to my face as I looked to either him or Veronica and licked my way up his shaft, taking him in my hand and making a production of it.

Making love to his manhood by always showing my respect and my adoration, it was my way of letting him know he had a real cock, a man's cock and where I didn't...

Yet as lucky as I was in not having to show him my cage right away, I was not so lucky in how I wanted to do this, how I was presenting myself... It wasn't our usual and it wasn't what Brother Reg wanted...

"No, no... You know that's not how we do things Dana-girl... That's not how real cocksuckers take care of business now is it? Come on, you know better" He said looking down at me, catching me and not letting me get away with what I was doing...

"Suck that cock, like you know how... Start here... Kiss my balls and make love to them, show your Mom you know how this works sissy"

Put down again but following his instructions, I could tell he was annoyed with me, or maybe it was for my Mom's benefit, I wasn't sure, and nor was I about to ask as I did what he said. Hearing him call me sissy with such derision in his voice was enough to get me moving.

Hurriedly, I brought my nose, lips and face up to him, Brother Reg was holding himself, keeping the skin of his hanging ball sack relativity tight with one hand and with the other, I felt his open hand coming to a rest at the back of my head where he ushered me in to the point where my senses, smell, taste and even my hearing became all about him.

His manly, musky smell, his warm hairless ball sack, everything was Brother Reg... It was all sack and balls for me at that moment...

"Mmmmff!" I moaned as my face was planted into his full nut-sack, like being pushed into a pillow Brother Reg's huge, hairless balls, kept that way of his own accord and probably for times like this, when tea-bagging his girlfriend's submissive 'gay-boy' husband... He held me there, obviously enjoying himself as I left out a second, softer sounding "Ummph!"

"Ohhh yesss that is sooo fucking sexy" I heard my Mom groan out, reminding me she was there as I continued with my face smothered in Brother Reg's balls, I did his biding, kissing and even licking his warm, sex-wet skin, tasting his salty-sweat as Mom called out, obviously loving her front row seat...

"I know Ma'am... Don't you just love it? Make him suck you now Brother Reg, let Dana-girl's Mommy see him throat your great big cock, but don't take to long! I need that thing back in me if you're gonna knock me up!" Veronica chimed in then, commenting and agreeing with my Mom, or Ma'am as she likes to call her, agreeing and saying that seeing me suck cock... It's an awesome sight...

But with her impatience also showing through, Veronica wanted us to hurry things along so that Brother Reg can stuff his big thing back into her and fuck her properly, trying to make her pregnant, or 'knock her up' as she was so eloquently in saying...

"Yeah, go on Dana-girl... Get to work, that's enough ball licking for now... Suck that cock, get me wet again, this is a big one... Who knows? We might just make you an Aunt... That sounds about right don't you think?" Brother Reg added, mocking me further.

Bragging and saying he's going to father our child but I would be the Aunt rather than a parent. I was an outsider, or a satellite-relative only there to help raise and take care of their baby... It was stabbing in a way, but I knew my place by now and I was growing used to Brother Reg being this way with me... Condescending and taking pokes at me whenever he can.

Moving some, I backed away allowing him to hold and point his big, half stiff cock down towards me and where looking up to him, I moaned once more, running my tongue down the length of him from tip to base and back up again before swallowing him whole.

Gagging and sputtering I was doing my best to give my Mom a show, I was letting her see me, her sweet little gay-boy being a real cocksucker, throating and choking on Brother Reg's thick mast of a cock...

"Ohhh God Dana baby! Yes! Oh fuck yessss suck that cock! That is so hot to see!" Mom bayed once again breaking my concentration with my eyes flicking over to where she was still seat, naked, perched behind Veronica and watching, sounding excited and most certainly turned on.

The two naked woman, Veronica with Mom spooning her from behind, with her left hand cupping and lifting my wife's one tit, rolling her thick nipple in her fingers and while even more surprisingly as I looked again, I moaned with my mouth full of Brother Reg's big dick looking and seeing Mom with her right hand and at least three of her fingers buried into Veronica's gaping, sloppy wet looking pussy as she lay there sprawled out with her legs spread wide and looking to be enjoying this just as much as my Mom was...

"Unnnggg" I called out with my chin and face covered in my own spittle, my eyes feeling watery and wet, choking down Brother Reg's big cock with my mascara no doubt in a mess already, and I hadn't even been home for twenty minutes...

"Uhhhh... Yeah, okay that's enough... Man, you are good at sucking cock Dana-girl, and like I said... I have someone I want to introduce you to down in the islands... But for now... Ladies? Did one of you say something about making a baby?" Brother Reg said first to me, as he moved and pulled away, taking his slimy wet, spit covered cock with him stroking the big thing as he turned, speaking to my Mom and Veronica.

Turning back, even I was a little shocked to see the pair of them involved in what looked like real lesbian play, if you were to ask me. Because by this time my Mom, not only was she mauling my wife's spread out pussy, but now she had Veronica's lower jaw in her hand as the two women French kissed looking fevered and impassioned with each other. Caught up with their eyes closed and making out like they were in a porno shoot.