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No, I didn't have any real qualms with Patti and my Mom having a little fun of their own... How could I..?
We were quiet for a minute; I glanced down looking at my ring...
"This ring is really nice; I love the chrome and the inset diamond. I'm just glad you didn't get me some big thing that a real girl would wear..." I began holding my hand up, letting the light reflect off the chrome surface and setting the diamond to sparkle.
"This one is stunning, so glittery and bright..." I went on...
"But don't you have one too Patti? What was the other ring in the box? I know there were two when you showed them to me..." I said to her, asking while lowering my hand and turning to her.
"Y-yes... Yes there is a second ring sweetie, but don't you worry your head about it, that one is for part of the ceremony... You'll see soon enough my love.." She answered, hesitating at first, giving me the impression that she may have been making up what she was saying. Problem was though, her explanation sort of made sense, I guessed -so I didn't push the issue.
My main concern was that I was the only one with a ring. I suppose it was just more of this strange 'reverse-engagement' we were involved in. Like everything else, this was just as different...
I just felt bad for Patti... Here she was 'the bride to be' - and it was me who was wearing the engagement ring...
That's when I began to worry... And the reason being..? I was also too afraid to ask, yet I knew the question couldn't go unanswered... I had to know what I'd be wearing... I had to know what they had undoubtedly already planned for me to be dressed in on our wedding day... I hoped to God it wasn't what I was thinking...
I started to say something but Patti must have read my mind...Stopping me she said "No Dale, you can relax, I'll be the one wearing the white dress..." She said to me rather dead-pan waggling her finger at me, and much relieved I sighed out loud...
"We talked about this didn't we Jen..? Or I should say we joked about it because we knew you would ask this question Dale... You were wondering if we were going to be putting you in the wedding dress weren't you sweetie..?" Patti went on, ribbing me and poking a bit of fun, because to both of them, I guess I seemed rather predictable, and sure enough, I had just proven them both right.
"Well yeah... I figured since the two of you had so much fun dressing me up the last time..." I said back offering some defence, weak I know but I had nothing else...
"Ohhh -- don't look so worried..." Patti said leaning in to me while scrunching up my face and lips in her fingers, puckering me up for her to kiss, as she went on then, telling me of their clothing ideas...
"Like I said, you don't have to worry, I'll be the one in the dress and you'll be in a tux... However though, I can't say you'll be wearing your old boxer-briefs under your trousers..." She added, making mention of the idea that under my tuxedo I'll probably be dressed in some sort of silky lingerie, and I was quite alright with this -as I let the two of them know...
"I don't care what kind of underwear you're planning on dressing me in under my tuxedo... Hell -- I'll gladly wear stockings and garters, just as long as I'm not the one wearing the dress... That's all I ask!"
We all shared a bit of a laugh over this; my being so emphatic, it was rather comical and even I could see the funny side of it in this upside-down arrangement where I felt like I was going to be more the bride than I was the groom.
Mom stayed with us for dinner, where after Patti suggested that I might want to freshen up with a shower, saying that I still kind-of smelled like the lake... I was a little shocked with her saying this, because God knows I showered enough while I was up there, but still, maybe they could smell something that I couldn't...
Yeah, smell something like the big fat lie she was telling me just to get me showered and ready for what they had planned next...
However, I was still a bit `tender`` I guess you could say. Not from all of the hard, pounding gay sex, and not to forget, Darren also spanking me... But rather, I was tender in the sense of feeling guilty and unsure about what I had allowed myself to do and also how I enjoyed myself -- so very -- very much...
"Come back in just your dressing robe sweetie, your Mom and I have a few more things we'd like to discuss and go over with you... Important stuff, so don't dawdle, off you go baby, have your shower and come right back..."
That's all she would tell me, they had more 'important stuff' to go over with me. I wasn't entirely sure what my being naked under my dressing robe would have to do with planning our wedding, but whatever it was that they were thinking, I was more than willing to 'play' with Patti and my Mom...Especially so after spending the last three days being the gay-fuck-toy for both Darren and Dean... I was more than ready for whatever 'my girls' had in store for me.
Half an hour later I came back down, showered and naked under my short dressing robe, as instructed and back into Patti's living room to find the two of them as I had left them, sitting in the same seats, both fully clothed, which after picturing all sorts of sexy things as I showered, I had imagined that I'd come back to maybe find them as naked as me -and possibly even starting without me...
But no, that's not what awaited me... Not at all... At least not this time...
"Oh there you are! Good, we can get started..." Mom said as she came up to me, taking my hand and leading me into the room and over to where they were sitting with Patti, up now and spreading out a soft looking blanket across her long, solid coffee table.
Right away, I had a queer feeling running through me --and it wasn't the good kind either... I was leery of what they were planning, they seemed too nice, this was contrived, plotted and schemed... That's what I felt anyways...
"Uhhh... Okay..? What's going on now? Why the blanket?" I asked pensively as I was stopped and positioned at the long end of the coffee table, now covered in a soft surface with my Mom behind me, slipping her fingers into the neck line of my robe and easing it off my shoulders, taking it away and leaving me naked.
"It's for you sweetie, your Mom is going to teach us how to do something that she used to do with your Dad -and once she told me about it, I thought that you and I could do the same and carry on the tradition, like a legacy to your Dad I guess you could say..." Patti explained as both she and Mom helped me down onto the table, down onto my all fours with my palms and knees resting comfortably on the thick blanket.
Naked and in the position they wanted me in, with my hairless little dickie, hanging and dangling below me looking aroused and semi-hard, I was nervous and apprehensive, I didn't know what it was they were going to have me do, or 'do to me' as it turned out, but whatever it was, it too was also about to become a tradition...
However... My naked arousal didn't go un-noticed -where for once I wished my small size would save me... I couldn't be so lucky...
"Ohhh! I see someone is excited!" Patti sounded off at seeing my little stiffy jutting out from under me, my hairless little balls pulled up tight to my body betrayed me, my being turned on like this, it couldn't be denied.
"I always forget how small and pretty your little thingy is Dale, it's so cute and pink... It looks like a cock but it isn't though is it? I mean, not like a 'real' cock... No offence baby... I've just missed you and sometimes I forget how precious your little guy is..." She went on, embarrassing me to no end, while I knew she wasn't trying to hurt me, she just had no filter and said what she was thinking...
Centred on the table, I hadn't forgotten about Mom behind me, just with Patti going on about my little dickie, remembering how small I am -after I'd been away. I had however been distracted from what Mom was doing -until I heard her speak while at the same time, I was sent gasping, calling out "Ahh! That's cold!"... Surprised with shock when feeling her parting my ass cheeks and applying something cold and wet... Lube -- of course...
"No... Sadly, he's not very well endowed... He's inherited that trait from his Father I'm afraid Patti..." Mom began as she ignored my cries, running her slick finger tips in and around my twitching little butt-hole...
"But in the end..." She went on... "You'll both see that as your marriage and your love deepens over time, Dale's being under-endowed will benefit the both of you -- as it did with his Father and me..." She finished saying, explaining and talking about my small penis size while at the same time she was still lubing my back entrance for what, I still wasn't sure.
However, what I did know was that after the initial shock of Mom drizzling the cold lube onto my unsuspecting rear end -I liked how her fingers felt smoothing out and applying the cool, slippery lube to my recovered little 'boy-pussy' after being fucked so hard and vigorously over my gay-weekend away...
"And like Dale, I also kept his father hairless as well..." Mom continued, talking to Patti like I wasn't even there -- yet with her fingers lubing up my ass? I'd say I was there alright...
"I swear they are so much alike -- and they'll be even more so alike with that 'something else' I've already told you about Patti..." Mom added, comparing my Dad and me, our attributes, or the lack of -as the cased may be, and also she was being rather secretive again, talking to Patti and mentioning this 'something else'...
But of course I was far too distracted at the moment, what with Mom snapping a condom over her two fingers, then working my ass wider, as I squinted and winced, She was readying me for what I believed was more than likely this 'something else' or part of it at least...
"Okay I think we're ready here, Patti pass me the wand please..." Mom asked as she slid her two latex condom covered fingers back out of my ass, making me grunt with the sudden evacuation, but at the same time leaving me with the feeling of emptiness, and not only this but leaving me to wonder -- what was this 'wand' she was asking Patti to hand her?
"What are you going to do with that..?" I asked looking up to see Patti handing Mom this 'wand' thing that looked sort of like an antenna that you can slide in and out, make it longer or shorter, but on its end, at its tip instead of just a blunt stopper, this thing, this wand, it had a dull, silvery looking oval-shaped ball attached to it...
"This my darling son is a great little tool is used for prostate milking, and trust me once you get used to it, you're going to love it..." Mom began as I watched her placing a large dollop of clear lube on its end before I turned and put my head down to the blanket covered coffee table, knowing where this was going but still not fully understanding its purpose, or why she was doing this to me.
"Ahhh!" I called out with my back going into an arch and my head coming up as Mom slid this very cold feeling little almond shaped ball of steel into my ass on its long telescopic pole.
"Why is it so cold..?" I bayed, lowering my head back to my folded arms, slowly getting used to the cold metal ball -- and believe me, it wasn't the size of the strange little thing, it was tiny in comparison to first Darren and then, Oh my God! Dean and his huge cock stretching me and pushing me to new limits, no it wasn't the size at all...
It was more just the oddity of the situation, the strangeness of not knowing -- that's what had me gasping and feeling uneasy as Mom passed this thing into me, breaching my outer and inner rings, pushing it in a good way and then with my body going into a jolting shiver making me sigh and gasp, she had hit something --and apparently, it was my prostate gland...
"Uhhh... Ohh..." I called out this time in more of a yearning, mewling sound with Mom hitting this hidden magic button she'd somehow managed to find, seated deep within my ass and suddenly sending a shock-wave of surprised pleasure rumbling through me.
"Ah-ha! There it is..." Mom declared -- triumphantly...
"That's your prostate gland Dale sweetie, and for males, this is where the real magic happens..." She explained, rotating the wand, searching and finding the best spot, the one that had me gasping and my eyelashes sent all aflutter.
"It's not so much in your balls baby, that's what most people think... Your little balls only produce your weak-beta-sperm; it's your prostate however, that's where the real pleasure resides in girly-boys like you..." She continued, explaining as she slid the device over the bulb-shaped gland that was reachable through the inner walls of my rectum, a good two to three inches inside of me where I could feel her massaging back and forth, slowly, and joyously driving me insane...
"This your version of a girl's clitoris Dale honey... Only for poor boys like you, it's kept hidden away deep inside, which isn't fair at all, I know -but that's where this wonderful little milker is going to come in handy for you and Patti..." Mom went on as I held my head down and had my eyes closed, gritting my teeth and afraid to admit just how incredibly amazing this little ball felt hitting me in that perfect spot.
But then Patti noticed something else...
"Oh wow look at that Jen! She began sounding happily surprised, I stayed where I was, my eyes closed getting used to and even starting to enjoy this new but very strange sensation...
"His little pee-pee has gone all soft and tiny; it looks like it's trying to hide..!" She commented looking under me seeing that my little dickie had lost its stiffness with Mom massaging my prostate.
"Yes Patti, that happens to a lot of beta-males like Dale, when something, or 'someone' is inside him, he'll lose his little erection and go like that... They call it going 'Sissy-soft'... Isn't that just a darling name for it..?" Mom explained to Patti as once more I was left out, talked about and acted upon like I wasn't even there...and of course, Patti agreed, they both loved the name for me losing my erection while having my ass played with -- but in the end, I couldn't argue with them, because that's exactly what was happening...
I wasn't new to this -- not entirely, going into this shrunken state, 'sissy-soft' as Mom called it...And also as I just said, I've had much bigger and much longer 'real' cock's fucking me and I had felt my prostate being hit and stoked repeatedly by most things that had been put into my ass...
From Mom's loaner-dildo to Dean and his monster cock and also not to forget, my biggest challenge -- the almighty 'Bruce' -- Mom's also 'borrowed' gigantic black rubber dong that I had fucked on camera and made a cool 5-grand in the process, thank you very much for that Mr. Lynch -- and Bruce!
However, this little thing in my ass, it was different...
And also... It was about to get very much more different...
Where Darren and Dean had all touched me here, hitting my prostate while fucking the day-lights out of me... I was about to find out that they were only grazing the surface, merely playing with me compared to what I was about to experience...
This thing, this 'Milker' -- it was concentrated, it was hitting my prostate gland -and that only... But then the l metal ball, suddenly it started bouncing and pounding the little button in my ass that I'd known of -- but was only truly feeling it just now... With my breath taken, my eyes shot open as did my mouth...
I had no idea it was also electronic-- not until Mom turned it on and -- Oh my fucking God...
"Unnnnngggg... Ohhh!" I bellowed with my head snapping back when my Mom, feeling I was ready she pressed a button at the bottom of the wand, where hidden in the hand grip was a small motor that as it transferred up the telescopic length, once the vibrations hit the steel ball lodged deep in my ass, I thought my head was going to explode with it hovering over my prostate gland the - 'male-clitoris' as Mom had said...I'd never felt anything so intense in my life, it was agony and ecstasy hitting me hard -- both at the same time....
This thing was incredible... So far, nothing had come close to making me feel what I did then, I was simply blown away that something so small could feel so powerful, take me and grab me, just as if I was being electrocuted... I simply couldn't move! I was absolutely paralyzed by this tiny little ball in my ass...
"Unnnggg" I grunted again as I felt something happening, like something was moving, I felt like I was going to pee but at the same time, I knew that I wasn't. My body was confusing me as it responded to the constant harmonic vibrations ringing out through me -and my ass, its efforts centred on my prostate, vibrating and hitting the small bulb like a drum at a furious pace and with it, I could feel myself beginning to drip...
"Oh shit! I forgot his tray..!" Mom called out then... "Quick Patti, it's there on the side table, the little silver one, quickly now, grab it and put it under him..." Mom said to her in a bit of a panic after forgetting this thing - 'his tray' -- or more like 'my tray'...
"Okay! I have it..." Patti said then as I looked down and back between my legs to see her placing the small, silver dish under my slowly leaking, soft and shrivelled up little dickie, with it looking so un-manly and pathetic, a thin, dangling thread of my milked cum hanging and dancing like the sinew of an abandoned spiders web left broken and swaying in a breeze...
"Well that was good timing! We nearly had a mess to clean up later because look Patti, he's really starting to flow now..." Mom commented as I too could see that what at first was just a thin stream of cum, it was now growing in thickness and colour, changing from a clear-pre-cum state to a cloudier pearl white, signalling that this was indeed my cum, and with this thing in my ass, it was doing as Mom had said it would...
It was milking me... Milking me but not like a cow, or even a baby nursing, drawing life from its Mother... No indeed... I was being milked differently; I was being milked from the inside -- out...
Patti looked on in fascination as I struggled and groaned feeling like I was peeing when in reality, I was being robbed of my cum, it was being taken from me... Mom was making me cum -- without cumming...
"Uhhhh... Ohhh... Oh this feels so... Uh -- so strange..." I moaned out as we stayed like this, the milker, doing its intended, draining me of my cum and feeling like nothing I'd even experienced...
The vibrations of this little thing in my ass were sending out shock waves that were so strong, I swear even my teeth were rattling as it kept pounding that little gland, making it give up my inadequate, beta-male seed in this slow process, my little dickie looked like a tap that had been left half open with a thin, continuous stream of my cum flowing out and gathering on the silver tray below me.
"It shouldn't be too much longer Dale sweetie, you're doing wonderful, just stay as you are, relax and let it happen, that's the best way to get through it this first time, and every time for that matter..." Mom said to me, telling me to relax while letting me know this wouldn't be my first -- and or my last milking.
"But soon enough, once you've gone a week or two without any release -- that's when you'll really start enjoying your milkings sweetie..." Mom added over the constant humming of the electric motor while I did what I could to stay still and listen to what she was saying -- but mostly I was concerned with how long she was saying I'd have to go without any other form of release.
Together the three of us stayed as we were while this continued, the first of my milking sessions, lasting until my prostate had given up just about all that I had, and where at the end, I was left with just another thin ribbon of nothing leading down from the skin covered tip of my shrunken penis, down and connected to the puddle of my milked out cum collected on the small silver plate below me.
