The Wedding Ch. 04

However, desperate and filled with that hope of 'just-maybe' - it surly left me wanting to co-operate and readily agreeing with my former English teacher...

"Ye-yes Ms. Walsh... I -- I would like to cum... It's -- it's been a long time..." I stuttered back to her and I wasn't entirely playing either, I did want to cum, even if I knew it was a long shot... I had to try...

"Yes, darling, I thought so... But we'll see... Maybe we'll get it it later -- if we have time..." She said back to me, letting me hang on to the hope I was so anxiously clinging to... Yet as she turned away, looking back to Patti, dismissing me -- I could tell otherwise... I knew deeper down what 'we'll see' more than likely meant...

Carrying on, Ms. Walsh ignored my pleading, concerning herself with these 'other-things' she had mentioned...

"Now as I was saying, there are some things we can -and probably should discuss... Things like how much anal training you've been giving him? I can see that he isn't currently plugged... Is this something you choose not to practice? Because if this is so, I highly recommend you reconsider and keep his cute little bottom plugged whenever possible..."

"Well... I know he loves anal sex and being pegged..." Patti answered as she looked up to me "Don't you Gabby..?" But all I could do was stand there and nod, saying yes with my head -sheepish, afraid and embarrassed.

"You watched the video Rachel; you've seen what my pretty Gabby-girl is capable of... He was such a bad little sissy, taking such a huge cock in his ass and loving it up for the camera..." Patti replied smiling up at me again as she stayed sat beside Ms. Walsh with me standing there naked and burning as as they talked.

"But you really think using butt plugs is important..? I never thought of them until now..." She went on as Ms. Walsh not only explained but also, she literally showed us -- or me -the 'benefits' of being made to have a butt-plug stuffed up my ass all day long...

The chastity I was sort of getting used to -- and yes, I do love anal sex but a butt-plug? Whenever possible? I wasn't so sure, and neither was I certain of any of these benefits Ms. Walsh was going on about...

"Oh absolutely Patti, in fact while I'm here, I insist that Gabrielle is fitted with the right size plug..." She continued, insisting to Patti that this is something we should and 'were' going to be doing... Looking to me, she let go of my balls, directing and telling me... "In my car Gabrielle; on the back seat you'll find a black carry-all... Be a dear and bring it to me..."

Being ordered like this I stayed quiet with my head down. I knew I was going to have to step out onto the driveway at least, naked and I also knew that somewhere inside this black carry-all was a big butt plug -- with my name on it...

And yes, I also knew there was no one out there to see me, what with the house set so far back in the estate, but still, there are gardeners and grounds people, so I knew if I was going to do this, I was wanted to be quick... Walking away I could hear Ms. Walsh continuing on, talking to Patti...

"Being plugged will give Gabrielle the heightened sense that SHE is not a man, and that HER only gateway to sexual pleasure is going to come from having HER little boy-pussy stretched and played with..." I heard her saying in a quirky way where she began referring to me as 'her' and saying it with emphasis, making sure I could hear what she was saying as I made my way out into the hallway.

***

Cracking the door open and taking peek outside, I chose to make a game out this, pretending I was trying to get out and back undetected, which is what I was doing -but I in my head, I wasn't naked...No... In my head -- I was a stealthy spy...

Taking a deep breath and seeing Ms. Walsh's car sitting behind Patti's sedan, I surveyed the area and then as quick as lightening, I darted out clinging to the side of Patti's sizable saloon, crouched down and trying to make myself as small as possible, creeping along with my back to the car and moving fast in my bare feet...

Thankfully the car was unlocked and opening back door of Ms. Walsh's older model compact, I found the black canvas bag she wanted -and then in a quick dash to freedom, I raced back to the house, standing up and bolting the short way across the lawn before diving in to the hidden safety of our front entrance...

"Whew..!" I said aloud... "Yesh -- that was a closh' one Monypenny..." I added then, answering myself while doing lousy Sean Connery impersonation, pretending I was 007...

It worked though, playing my little spy game... I hadn't been seen or detected and I had the bag -and nor did I freak out, panicking and sprinting across the lawn completely naked...

***

"Oh good you're back... Come Gabrielle, bring me my bag; you may come back in... You're very good to wait... I always liked that about you darling, you were always so thoughtful and polite..." Ms. Walsh said to me as I stood there at the threshold, inviting me in to what was essentially my own living room -- but at least my instincts had been correct... My waiting before entering was a good thing to do...

Handing her the bag, I stood at her side, not sure about what I should do with myself. It was one of those moments where I felt the most naked and vulnerable.

However then...

"Here it is... It's brand new, but I wanted to keep it clean for you..." Ms. Walsh said after rummaging in her bag, setting it down and coming back up with a clear plastic baggie containing what I assumed was a butt plug... My butt plug...

Taking it out I noticed straight away that this was like no plug I had ever seen before... My eyes went saucer wide when she sat upright, smiling and holding this very big looking, shiny, steely, metal coloured thing.

Looking like a tear-drop as she held it by the base, the stem leading up to the wide, bulb-shaped cone that I thought there was no way -- no way on Earth this thing was going to fit inside of me... At least not without a lot pain, and no matter how much lube she planned on using...

"Not to worry... I have this lovely 2 ½'' plug here for you... Patti, I'd like you to assist, so you can learn, actually, I'll even let you put it in, how does that sound..?" Ms. Walsh asked Patti while holding up the big, ominous looking thing...

"Oh I'd love that..! What do you need me to do..?" Patti replied sitting up all smiles, ready and very eager to learn...

"Push that ottoman over here... Gabrielle, be a good sissy for us and lay over the top of the footrest, kneel on the floor first and then drape yourself across, here I'll help you..." Ms. Walsh explained as I did what she was asking of me, knowing that I had no other way out...yet oddly, part of me was willing and wanting something to happen. It had been too long; I needed attention -- any attention...

"Very good Gabrielle, now spread you legs for me and let's take care of this shall we..? She instructed as I heard the snap of a rubber glove before letting out another grunt "Uhhh!" with Ms. Walsh grabbing my cage from between my legs, pulling everything back, making it easier for me to lay myself out, getting ready to have this very big looking butt-plug inserted into my tight little asshole.

"Ahhh! Oh that's... Oh it's cold..." I cried out then as I felt Ms. Walsh pushing a slippery lubed finger into me, twisting and turning before retreating only to come back yet this time I'm sure she had two, possibly three of her latex coated fingers going in on her second push, once more forcing the air from my lungs in a grunting "Uhhhh..."

"Mmmm... Oh this is good, very good, he's quite pliable...We'll have no trouble getting this size plug into him..."

"Patti, if you would like to take my place..." Ms. Walsh went on as I felt them switch with her now kneeling beside me, her warm hands on my ass and then hearing Patti, snapping herself into a pair of the same latex gloves, with Ms. Walsh's prying and holding me open, spreading me wide as I lay splayed out across the ottoman footstool.

"There's a good sissy... You can take this plug in one easy push, I'm sure of it... You really are a slut back here huh..?" Ms. Walsh asked as I felt Patti lining up the tapered, blunt end of the plug against my puckering, clenching little hole.

She may have been sure, but still... It was big...

"Uhhhh Ohhh it's too biiiiggg..." I cried with my head nearly touching the floor, unable to see, only able to feel Patti doing as Ms. Walsh had instructed, sinking the 2 ½ inch butt-plug into me with one long, slow, relentless push.

"Keep going Patti, that's it.... And you can take it Gabrielle, it's nothing you haven't had in you already... Don't forget I was there watching your movie... And I've watched the two others since then, so I don't know why you're crying..." Ms. Walsh said to me, humiliating me even more, reminding of her being there and seeing my up on the big screen with Big Bruce all the way up my ass... And now, hearing how in her own time she had watched all three of the movies I'd made with Darren and Dean tag-team fucking me out on the boat.

Humiliating me with her words as Patti was reaching the widest part of the cold, slippery lubed up butt-plug, hitting that crest, the top of the roller coaster where everything stops but for the briefest of seconds - before....

"Unnnnnnggggggg... Ohhh -- Ohhh... Ohhh God..."

Before the plunge...

"There we go..!" Ms. Walsh declared, as my ass finally accepted and then swallowed the big plug whole...

Laying there, panting and breathing hard with my eyes rolling back in my head and feeling my little ring collapsing closing back in around the plugs narrow stem, the entire thing now seated deep within my rectum, the pressure incredible and relentless... Like a cock being buried deep, I needed time to adjust...

Letting me do this, letting me rest and breath while trying to accommodate and get used to this feeling, This incredible sensation of being filled... I felt the two of them move away, but not for long...

"Sit up for us sissy, let's get you up and walking, give it some time and soon enough you'll become used to having your ass plugged for longer and longer periods..." Ms. Walsh directed, degrading me, calling me 'sissy' as she and Patti helped me up from my splayed-out position over the ottoman...

It took a second or two but without too much trouble and strife coming my way, they had me up on me feet, wincing some and hoping this big steely butt plug wasn't going to somehow pop out of me...

Yet with its size and how my ass has this way of correcting itself after being stretched and toyed with, I could feel my outer sphincter clenching and encircling the tapered middle leading out to its round base, the bottom of which was housed and mounted with a purple coloured faux gem stone -Patti's favourite of course.

However as I was set upright I knew this thing was deep and there was no way, no way in the world this thing was coming out... At least not without a lot of help...

Standing naked with this big, heavy butt plug up my ass, Ms. Walsh had me walk the length of our living room, even past the long floor to ceiling widow frames with the curtains drawn open, but again --and thankfully there was no one to see me out there in the empty estate grounds. No one except maybe the birds and the chipmunks...

"Oh Gabby! That plug gives you such a wonderful swish in your hips and I just love the jewel in the end, I can see it glimmering when you walk away from me... Bend over baby, show me more..." Patti said to me, commenting in a happy, sexy voice, asking me to show her my plug as I walked the room, all the while it was easy to tell from her voice alone that she was horny and turned on by all of this and as I noticed Ms. Walsh looking to Patti as well, I wondered if she too could sense Patti's arousal -and what if anything she might do about it?

Following her request, I went one better by turning with my back to her and placing one leg up on the ottoman, I gave her a great view of the plugs glittery-purple end, while at the same time looking back at her over my shoulder, trying to look sexy, playing this up for her, wanting to keep Patti happy and turned on.

And then maybe more than I had anticipated...It was working...

"Mmmm... Oooh yeah baby, God that looks amazing in your tight little 'boy-pussy'..." She said in a rushed, urgent tone, pressing her legs together under her skirt, first looking from my ass to me than then to Ms. Walsh, it was easy now to see the lust and want in her eyes, her body language telling me there was no mistake -- all of this was turning her on...

And of course, this too didn't go un-noticed by Ms. Walsh either... But in a much, much different way...

"Swack-Crrrrack..."

"Ahhhhhhhh!" I screamed with very sudden and very sharp sting of had leather strap striking the inside of my right thigh like a thunderbolt...

"I never said we were finished Gabrielle, now stop showing off and get your sissy ass back over the cushion... NOW..!" She burst out saying as I recoiled in pain, taking my foot down and scampering away a few paces racked with both pain and sudden fear...

Looking to Patti with a certain panic in my eyes, she was just as surprised as me, except I doubted the inside of her right thigh had been just been smacked hard with a leather strap and left burning with fire and feeling like I'd been branded with a glowing hot fire-poker...

"Patti... This is a part of living in a FLR lifestyle... Discipline..." Ms. Walsh said to her, then turning back to me as I trembled, standing away from her, paralyzed and afraid to move.

"Gabrielle..." She called out then, scaring me further...

"Do as I say sissy and get back down as you were... Your wife needs to learn how to take care of you better; because it's very easy to see she's been letting you get away with far too much..." She added sounding very stern, ordering me to lay myself back down as I was moments ago, offering myself while having this big, heavy plug stuffed up my ass.

But now... But now I feared something even worse was coming my way...

"Oh please Ms. Walsh I've... I've been good... I -- I haven't cum in ages and my plug... I love my plug..." I cried, begging a pleading, crying my innocence as I stood, hesitating to do as I was being told.

Holding the long leather strap up above her head and saying nothing, the fire in her eyes said it all... Crying, I slinked back, shaking and afraid, that strap hurt like fucking hell and I didn't want any more...

"Take this Patti, you're going to give him ten good ones, five on each cheek, this leather is well worn and it won't break the skin... He'll welt up for a day or two but this is crucial... As I said, I think you've been far too soft on your little sissy, especially since he's so willing..." Ms. Walsh commanded handing Patti her evil leather strap yo use on me.

"You are quite far along in your learning, but only in some areas... However with his discipline..? I can see surely that you're lacking..." Ms. Walsh explained as I slowly, at a turtles place, I lowered myself back over the ottoman, weepy with reluctance and know I'd be bawling my eyes out by the end of this...

Kneeling and looking up to Patti, hoping for her to sympathize with me and for a moment, I thought she might not be able to do this, disciple me like this with Ms. Walsh's leather strap...

"But... But I thought Darren would take care of this stuff... I -- I don't want to hurt him..." She said to Ms. Walsh trying to reason as I looked back and forth between the two, kneeling up still and not quite in my full position yet still I was shivering, scared to death and naked...

"Patti... You'll do this or it will be YOU going over that ottoman... Remember, this is about teaching you more than it's about Gabrielle the sissy..." Ms. Walsh said to her threatening Patti in a way that had her taking up the strap as she looked at me saying...

"You heard her Gabby... Over you go... I'll go easy on you... This time..." She said to me as I tried to hold myself together, slowly and again, draping myself over the footstool sniffling with my nose running, sobbing, my eyes wet with tears...

"But --but Patti..? Please..?" I begged again, looking up to my future wife, hoping against hope...

"No Gabrielle..." Ms. Walsh interjected... "Begging won't do you any good, and besides, we are well past that now... This IS going to happen... Now Patti... Before you begin, tell me... Can you think of a time when Gabrielle has annoyed or up-set you? Is there something maybe from your past that you've been harbouring? Anything at all? Even if it's been for a long time? Because if there is dear, now would be a good time to summon that image, remember and show us -- show Gabrielle how upset he made you..."

Admonishing me for pleading with Patti, then asking her to conjure up a time when I might have made her mad, giving her something to spur her on, using this tactic as tool to get Patti's arm swinging, meting out the disciple that Ms. Walsh believes I've been lacking...Right away my mind thought of how I blanked Patti all those years ago, not going to the last wedding, the 5^th in the long line that summer, the one 'after' I thought I had caught her going down on Brad, her ex-boyfriend.

And unfortunately for me, Patti too had thought of this very same thing, this same time and the incident where I'd left her to attend that last of the weddings alone and thus beginning our 15-yrs of estrangement, living apart and to lead very different lives.

'Well, yeah... This is easy because there has only been one time that Dale... I mean Gabby -- shit! I keep doing that..!" Patti started but then caught herself calling me Dale and getting mad enough to lose her train of thought... But not long enough for me...

"Remember 'Gabby'..? Back when you stood me up for the last wedding and I had to face all of my high school friends ALONE..?" Patti asked, sounding annoyed but really I think she was just making it sound worse than it was because we had talked about this on our date and she wasn't mad then... But I guess it was like she was saying, this was it, she didn't have anything else on me that had pissed her off enough to do something like this... To punish me...

"Swack..!"

Rang out a quick, short snapping sound as Patti gave me one across both my up turned ass cheeks, the pain wasn't so bad because she did hit me all that hard... But still, the shock value had me crying out...

"Owwwww..! Patti... No -- p-please..!" I bayed, while leaning over the ottoman with my arms straight, supporting myself along with my chest, trying to keep my head up and cocked to one side in an effort to look back at Patti, hoping she would reconsider... But no -- Ms. Walsh wouldn't let her...

"That was just a tickle... Give it to him Patti, you HAVE to do this or you'll never gain the respect he needs to show you -- and the best way to get there is through his fear and understand, learning and knowing that you are very willing and capable in meting out his punishments... This key Patti -- so don't hold back or feel sorry for him... Hit him hard and let him know...." Ms. Walsh barked to Patti sounding rather mad herself as she stepped in front of me, my eyes cast to her long skirt hem and those black leather boots...

I didn't know her intentions but I was certain I wasn't going to like whatever she was going to do...

Setting down in front if me and taking my hands in hers, she pulled my arms taut while looking in my scared, watering eyes while directing her words not to me but instead to Patti... "He'll see a weakness and go for it every time... If you don't lay into him and show him who's the boss, this whole thing will fall apart -- trust me, I know how cunning and sly a non-respective submissive can be... I've been studying this type of behaviour for over 20-yrs..."