The Cindy Triology

by X. S. Sillke

  

(1 - A Date with Larry)

(Part 3)

  

It was exactly a week later that I found myself in one of the guest bedrooms at Larry's putting the finishing touches to 'FrillyFiona', which was the pet name Larry had assigned to the fantasy image that I was attempting to bring to life for him. We had spent the afternoon with me dressed as slutty Cindy, drinking whisky and me flashing my tautly suspendered silk stocking tops and bulging silk panties at him until he could stand no more teasing and had begged me to go and transform myself into FrillyFiona. This had been his fantasy figure for so long that I was desperate to make it a success for him. I minced across to the mirror to see what the finished article looked like. I don't know where he had got this sissy-kit from, but it certainly wasn't the local lingerie shop. I looked with trepidation, but slowly warmed to the image that greeted me, but the wig was terrible. A mass of short pink curls with a huge bright pink bow tied in the midst of the tight curls. Everything else was also pink, not the delicate soft pink I had expected, but glaringly bright pink. The pink silk bra housed my silicone breast forms quite nicely, but I wasn't keen on the "Little Missy" embroidered on the cups. The sensation of the tight pink waist-cincher was pleasant, and the four broad suspender straps hanging from each side were great, I loved the sensation on my multiple suspendered stocking tops, the stockings being pink silk with lace tops and a thick black seam running up the back. I wore a frilly pink lace garter on each leg, positioned halfway between my knees and the stocking tops. A broad pink ribbon was also tied in a large bow just above my right knee. I loved the ankle boots, wetlook pink lace-ups which gripped my legs firmly and with an elongated chisel toe and six inch stilletto heels. Short sharp strides which made my tits wobble was the order of the day. The panties were of pink silk but with a seethrough mesh panel at the front, which left my highly excited member on full view. A pair of pink cire shoulder length gloves which were topped with pink fur for each arm and a matching broad pink cire choker with the word 'Sissy Boy' picked out in small diamontes. My make-up was, of course, totally overdone with pink eye shadow, pink cheek blusher and delightful sparkly pink lipstick, all layered on much too thickly. The false eye lashes even had a pink sparkle effect and were ridiculously long, they brushed against my nose when I fluttered them, I had never worn any so OTT before. I loved them !

I gazed at my reflection thinking that it was probably the desired effect, obviously a man dressed in pink lady's undies, and also obvious he was panty-bulgingingly excited to be dressed that way ! I took a deep breath. Time for FrillyFiona's debut. I tottered towards the door. Think sissy, think sissy, think sissy. I minced into Larry's bedroom and stopped to strike a sissy pose for him. He was laying naked on the bed, sporting an amazing hard-on. He was also wearing a black rubber hood with just eye and mouth holes.

"Oh wow. So this is FrillyFiona. Delightful. What a sexy sissy. Let me watch you strutting up and down sissy."

I duly obliged, taking small mincing steps in my six inch heels, my titties jiggling inside my pink 'Little Missy' bra, my gloved hands pointing out from my sides in true sissy fashion, and loving the multiple pull on my stocking tops from the eight suspenders. As I tottered to and fro I noticed a video camara in the corner of the bedroom, the red light winking telling me that this was being recorded for future enjoyment. Larry was standing by the bed now.

"I see you have noticed the camera, I want you to treat that as your audience, imagine it is a dozen men sitting there watching you, all getting their cocks out as they watch you perform. Now come here for the last part of your ensemble."

I minced across to the bed and Larry slipped a white padded PVC mitten onto each gloved hand and tightened the straps around each wrist, effectively making both my hands absolutely useless. I couldn't pick up or grip anything in the padded mittens. Larry sat me down on the edge of the bed and pushed his cock against my bright pink sparkly lips. I parted my multicoated lips to allow the excited cock to slide into my mouth and started to suck on it like a lollipop, my mittened hands hanging uselessly at my sides.

"That's it FrillyFiona, this is what sissysluts want isn't it, a big hard cock in their mouths, all dressed up in your silky undies, making you have a little stiffy in your panties dressing up in stockings and suspenders eh, being a little femme sissy flouncing about getting men excited.........sticking their cocks in your pretty painted face..........."

Larry suddenly pulled his cock from my sucking mouth and roughly stroking it before exploding all over my heavily made-up face, spurt after spurt, covering me, my shiny lips still wide apart and catching some of it. I had never known him come so quickly, he must be really turned on by this sissy scenario.

"Now go and show the gentlemen your pretty spunky face sissy."

I got up from the bed, struggling a bit to balance on my heels, before mincing over to the camera, my titties wobbling, and dropping down to give it a close up of my made-up face with its milky covering, globules still dripping from my long lashes and dribbling down my nose, licking my pink coated lips, gathering a few stray drops. I posed close-up for the gentlemen for a few minutes before Larry called me back to the bed. I minced my way over to where he was sitting. He reached up and slid my panties down my stockinged legs.

"Now do some more strutting for the horny gentlemen sissy bitch."

I paraded up and down the room with my mincy little strides, mittened hands sticking out from my sides, titties jiggling and my excited cock swaying from side to side with each sissy step. He watched me perform for some time before calling me back to the bed where he was holding my pink silk panties crumpled up in one hand.

"Now if you want to relieve that little sissy weeny of yours you will have to frot your panties sissy boy."

He held the crumpled panties out and I pushed my cock into the silky mass, and started to thrust in and out of the silken hand. My gloved hands in their mittens useless at my sides as I balanced on my mega heels and literally fucked my own panties.

"Feel nice does it sissy slut, eh, your little weeny slipping in and out of your frilly knickers, your little sissy weeny surrounded by silky panties, don't forget that the gentlemen won't be able to see when you dribble your sissy goo into your frilly panties so you will have to tell them when you do it. Nice sissy panties wrapped around your little weeny, your little sissy pole surrounded by silky panties, go on, frot your panties sissy..........."

I got into the rythym and started to let out little squeeky whimpers as I thrust at the crumpled panties, rubbing my silky stockinged thighs together for extra effect, and continuing to let out little whimpers, I was getting close, nearly there, I turned to the camera.

"Oooh........oooh.........goo.........goo goo.....I'm going to squirt goo goo........squirt sissy goo into panties.......squirt panties......ooooh.....ooooh........yes..sissy goo squirting.....ahhhhhh......."

Larry reached up with my sodden panties and wiped them over my heavily painted face, adding my own deposit to his own still sticky mess, and then scrunching them back up into a ball he pushed them into my mouth.

"Go and show the gentleman what a messy little sissy you are."

I tottered unsteadily across to the camera, bending down in front of it to offer a close up of my twice spunked on face and my bulging mouth with the shiny pink lipstick forming a circular frame around the frilly pink panties filling my mouth. Larry summoned me back to the bed. He had rolled a rubber down his rejuvenated member, wow, this sissy thing was turning him on. He picked me up and dumped me down on the bed where I landed on all fours. With absolutely no ceromony whatsoever he climbed behind me and slid his length up into my bum.

"This is what all sissy boys love best isn't it, feeling a cock up their bums, you suck your juice out of those silky panties sissy, while I give you a good sissyshag, all dressed up in your pretty pink silkies to make me horny you sissy slut, strutting about with your little titties bouncing and your weeny waving about all stiff and excited, just to turn me on you tart, ........................"

Again it hardly took any time before I felt him twitch and shudder inside me as he filled the rubber, before collapsing on top of me. We lay like that for some time before he gently turned me over and pulled the silk panties from my mouth, his lips meeting my heavily glossed lips in a passionate kiss.

"Mmmm, I think FrillyFiona is one hell of a sexy sissy bitch."

"Mmmm, I quite enjoyed being her as well, prefer Cindy fulltime, but I think FrillyFiona could emerge once a week or so providing you can think of more sissy situations to embaress her."

Laying cuddled together we drifted off to sleep. I awoke in the morning laying on my side and feeling Larry's hard member prodding at my rear entrance. God, this sissy thing was making him rampant. I lifted a seamed silk stockinged leg into the air to aid his entry, realising that my own member was also standing to attention. Damn, couldn't do a thing about it as I was still strapped into my PVC mittens. Larry slid into me up to the hilt and started to thrust at my pert bum. The coating of spunk over my made-up face had dried and felt tight on my skin, reminding me of my sissy status. The door suddenly opened and Minnie clik-clacked across the room with the coffee tray, placing it on the bedside table. Larry didn't break his rythym, still thrusting into me.

"Ooh Mees Cindy, you can't do the winking with those seelly gloves on. Here, I do it for you."

I must remember to tell Minnie the difference between winking and wanking. She scooped up my discarded sodden panties from the bed and draped the damp silk over my throbbing cock and gently started to tweak it with her finger and thumb through the flimsy material. I let out a series of little sissy whimpers as Larry rogered me from behind and Minnie panty wanked me from the front. Ohh it felt good. Larry beat me to it, twitching deep in my bum as he exploded in me, Minnie doubled her efforts on my silk encased cock to bring me whimpering to erupting yet another load of spunk into the silk panties.

"There we go, nice squirty squirty. Now you not let the coffee get cold."

With that piece of advice Minnie clicked away on her heels with a flourish of petticoats and out of the room. Larry slipped out of me and sat upright, pulling off the rubber mask and rubbing his face.

"I think FrillyFiona needs a nice little girly frock, something tight at the top to show off her jiggly titties, and flouncy and frilly at the bottom, just short enough to allow her sissy weeny to hang under the hemline."

"Kinky sod. It wouldn't surprise me to see a row of gentlemen sitting in the corner next time instead of just a camera."

We laughed. We did that a lot over the following years. After I finished High School I moved in with Larry and became Cindy more or less full time, with her flashing suspenders and tarty make-up. At times FrillyFiona appeared to spice things up, and there were the times that I had to act like the lady of the manor for social functions and charity galas, tightly corseted to hide unladylike bumps and with very sensible make-up. Larry had his 'boys nights' once a week when they would watch a match or play pool, Clifford used to come over for these, which was good because he used to bring Sam with him, and we used to have girly nights. Minnie often used to join us as we had our girly fun, her forte was being trussed up before being 'forced' to do it. Kinky mare. She did discover the difference between winking and wanking though. We laughed.

As a very good friend of mine would say - Way to go sweetpea !

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