A Missy Affair

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Closest crossdresser discovered and used.
2.4k words
4.33
153.1k
49

Part 1 of the 3 part series

Updated 06/10/2023
Created 12/10/2012
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I knew I was being careful. I thought I was being clever. But I never thought I could be caught in such incriminating circumstances by of all people my sister-in-laws husbands parents. I was playing the good brother-in-law by doing a bunch of minor home reno's for my wife's sister and her husband. To my delight they trusted me implicitly and left me alone in their house to work away. Which I did.

But I couldn't control what has been a life long secret urge - to snoop in women's things. And if at all possible to try on what I found. This turned out to be a dream come true moment. Left alone in a house for hours with an entire wardrobe available to me.

Each day I would avail myself of my sister-in-laws things. At first it would be only slipping into a pair of her pretty panties but it wasn't long before I progressed to slips, garters and nylons, camisoles, everything in her lingerie draws. There were even a few of skirts and tops that fit me, as well as a pair of slip on pumps. I was in cross dressing heaven.

I delighted myself by posing in front of the various mirrors about her bedroom enjoying my play time immensely. Every now and then a flicker of guilt would pick at me but I learned that if I bent myself over the back of a chair, pulled up the skirt and slip I was wearing to expose the tops on my nylons and my pantied bottom I could reach behind myself with a belt and deliver some very realistic and sometimes quite painful lashes while I watched in the mirrors. Or even a good swat or two with my open hand, delighted by the hot red hand prints on my creamy white butt. I loved the warm stinging after glow, especially the way the cool nylon slip and skirt swished over my tender bottom as I walked around the room afterwards.

I was fully into my playtime one day and having a delightful time punishing my exposed pantied bottom when I distinctly heard the clearing of a throat. I froze. The throat was cleared again leaving me with no doubt as to what I had just heard. Risking a furtive glance I noticed my brother-in-law's father reflection in the mirror. He was standing stock still in the open doorway glowering harshly at my pantied backside draped over the back of a chair. Taking a deep breath his voice boomed and my heart sank as he called out, "Mother you'd better come have a look at this."

My mind went blank as the full horror of my situation flooded over me. Frozen in place I couldn't have moved if I had thought to. While I listened to the heavy foot steps of his wife climbing the stairs I watched Mr Smith saunter assuredly into the room. He took his time. He made a point of looking closely at everything including my reddened bottom.

I trembled visibly at the shriek of his wife as she entered the bedroom. I watched her wide eyed with terror as she gaped at the scene before her. My terror turned to confusion when she suddenly burst into gales of laughter. Mr Smith joined her, chortling to his wife, "Oh god mother have you ever seen anything the likes of this in your life!?"

Her entire body shook with laughter as she staggered into the room to wrap an arm around him for support, shaking her head with dismay. I let my head hang as shame consumed me with the certainty that my life was ruined. I wasn't surprised to feel warm tears filling my eyes as I listened to them laugh. "Oh look mother," Mr Smith gasped mightly amused, "the poor little thing is crying!"

"Well father," his wife tittered, "best give the little sissy gurl something to cry about!" I watched stunned in the mirror as Mr Smith made a grand display of removing his belt and doubling it up as he advanced across the room to me.

I willed my body to get up and get out of there but it failed to take heed. I watched transfixed as Mr Smith drew back his belt and lashed my exposed pantied bottom with it. A squeal of pain filled the room as the white hot shock of the leather bit into my soft creamy butt. Before I fully comprehended that it had been me that had squealed Mr Smith had lashed me again and my body was bucking as I squealed with pain.

"That's it father," Mrs Smith shrieked over me, "give the little bitch something she's never going to forget!"

And Mr Smith did. By time he tired my bottom was criss crossed with burning welts and I had subsided into a blubbering begging mess. Beaming like the cheshire cat Mrs Smith sauntered over to me to study the aftermath of her husbands efforts. "Oooh very nice father," she cooed giggling as I flinched when she gently raked her nails over my poor burning bottom.

Unexpectedly she delivered a stinging swat to one crimson cheek then the other, throwing her head back and laughing as I whimpered pathetically. "How's that feel dearie," she snickered evilly in my ear, then giggled when my response was lost in a torrent of tears.

Resting a cool proprietary hand on my up turned bottom Mrs Smith commented archly, "Why father, would you look at what all your efforts have resulted in!" I thought she meant my poor tortured bottom but in the mirror I watched as she trailed her free hand over the bulging tent of the front of Mr Smith's trousers. The man had a massive erection and she was stroking it through his pants.

As I watched mesmerised as she deftly popped open button after button of Mr Smith's trousers until his raging hard on sprung into view. Mrs Smith watched me in the mirror watching her hand slowly gently stroke Mr Smith's impressive manhood. Soon there was a glistening of moisture at the purple tip, "Hmmmm father," she purred in a sultry voice, "whatever shall we do with this?"

Mr Smith just breathed deeply in response while looking intently at my well reddened upturned bottom. "Boy wants to act like a woman mother," he murmured throatily, "reckon we should treat him like one."

I couldn't believe what I was hearing but before I could even consider putting an end to it Mrs Smith sunk her nails into my ass painfully and while I was distracted Mr Smith looped his belt around my neck and tied the end to a leg of the chair. There I was draped over a chair, tied to it, my bright red bottom pantied and exposed, totally vulnerable, completely at the mercy of Mr and Mrs Smith.

Mrs Smith gave my bottom a last nasty dig of her nails before hooking them beneath the waist of my panties and pulling them unceremoniously to my knees. With her other hand she pulled Mr Smith into position between my legs and started to rub the gooey covered tip of his cock up between my cheeks. When I started to squeak and squawk in distress she dug her nails into me until I settled down then proceeded to direct her husbands cock back towards my ass.

As Mrs Smiths nails savaged me her husband forced his slick dick against my pert anus. I heard my self howl as he forced his way in and she dug deeper laughing evilly at my distress, "Oh yeah father," she shrieked excitedly, "fuck the little sissy bitch, fuck the little slut hard!" And Mr Smith did. Soon he was slamming his entire length into me as I moaned in unison. Mrs Smiths nails sunk viciously into my bottom were but a vague sensation as Mr Smith fucked me and I moaned like a bitch in heat.

"Oh fuck yes," Mr Smith howled driving his cock to the hilt inside my ass and pumped me full of his seed. Mrs Smith's eyes glittered with evil intent as she watched her husband twitch and spasm with orgasmic pleasure before collapsing on top of me. Mr Smith rested his entire weight on me and Mrs Smith cooed gentle nothings in his ear while stroking him back from his swoon.

"God damn that was something," he crowed giving Mrs Smith a long wet kiss before pulling himself out and off of me. My ass felt like an open cavern and I was utterly spent hanging there over the back of the chair.

"Yes father," Mrs Smith chuckled, "I'm sure it was. But now it's my turn." With that she gave me a shove and I fell from the chair to the floor. As I floundered there on the floor the belt biting into my neck she flipped me effortlessly onto my back before standing over me to stare down uncompromising totally in control. While I gasped for breath and gaped back Mrs Smith slowly purposefully raised the hem of her dress exposing first her fat creamy bare legs, then the wet crotch of her full support panty.

Holding me captivated with her commanding dominant gaze Mrs Smith slipped off her panties and I stared up in amazement at her hairless bald cunt. Mrs Smith's pussy was swollen and glistening wetly. Without a word she lowered herself to her knees onto my chest pinning me to the floor. As I trembled with a mixture of fear, passion and anticipation as Mrs Smith shifted her glistening pussy closer and closer until I could feel the heat of her sex and smell her excitement. She held herself just over my face until she was certain that I knew what was going to happen before lowering her body until her dripping wet fat pussy engulfed my face smothering me.

At first I reflexively lapped at Mrs Smiths oozing twat with my tongue but it soon became apparent that she wasn't interested in my cunt licking skills and began humping my face, using my face to massage her swollen clit onto. The folds Mrs Smiths fat moist pussy smothered me in wetness and my every gasp for breath was the overwhelming scent of her sex.

Struggling weakly beneath her I was barely aware that she had a vicious grip on my hair as she used my face to satisfy her need. By the time her thighs clamped about my head in a death squeeze of orgasmic release I was barely conscious, when she flooded my mouth and my nose with her cum I swooned. Mrs Smith continued to hump my motionless face eking out every last tingle of her orgasm.

I came around to her progressively sharper meaner slaps to my cum wet face. As I whimpered uncomprehendingly Mrs Smith slapped me again shaking my head violently by the hair, all the while laughing cruelly and calling out, "Come on little girl. We are't finished with our pretty little sissy bitch yet sweetie!" As I squeaked and squealed Mrs Smith hauled me to my knees then dragged before a now naked Mr Smith. Mr Smith was grinning with a cruel knowing gaze as his wife held me by the hair before him.

"Clean up your mess bitch," he snarled down at me thrusting his hips forward causing his cum slick cock to brush over my nose and cheeks. When I cringed away Mr Smith reached out to grasp my hair away from his wife pulling up harshly before slapping me with his free hand. Mr Smith slapped me until I was a weeping pathetic mess. When he finally stopped he quietly held my face before his semi-erect cock and without further encouragement I dutifully began licking and kissing Mr Smith clean of the remnants of his assault on my ass.

As I licked and sucked dutifully on Mr Smiths cum slick cock it responded and engorged standing out rigidly from beneath his fat gut. Holding me at bay by my hair with my tongue and mouth still trying to work him, Mr Smith growled, "Look at the greedy little slut mother. Little bitch can't get enough!"

"Hmmm," hummed Mrs Smith, "get the that cum slut over here and lets teach the stupid twat where a sissy place really is." With that Mr Smith dragged me mercilessly by the hair to the beds edge. Leering deviantly down at me he held me pinned there as Mrs Smith crawled onto the bed over me and slapped her fat still moist cunt down over my terror stricken face.

"Oh god," I moaned as she once more smothered me until I was left gasping for breath in the folds of her pussy. While Mrs Smith pinned my head to the bed Mr Smith straddled my body and began forcing his rigid cock in between Mrs Smiths thighs and into my face. Gasping wantonly Mrs Smith guided her husbands massive erection into the folds of her pussy and I felt him slide deep inside her as she groaned pressing herself down upon me. While Mrs Smith groaned and grunted Mr Smith fucked her from behind as they rocked back and forth over my face.

With a long shuddering convulsion Mrs Smith came. Juices flooded from her pussy drowning me. While she convulsed with orgasmic delight Mr Smith roared slamming his body into hers and came violently. As their orgasms twitched and trembled through their bodies the Smiths smothered me with their combined weight and a heady mixture of their juices. At some point Mr Smith must have pulled out but Mrs Smith continued to use my face for her pleasure. I struggled weakly until passing out once more.

When I eventually recovered I was laid out on the floor. Mr and Mrs Smith stood over me smiling, self satisfied, glowing with post orgasmic pleasure. When they realised I had regained consciousness Mrs Smith squatted down beside me and while gently stroking my hair told me casually, "Father and I are so going to enjoy having you come visit us sweetie."

As she continued nonchalantly I sniffed back a tear of shame, "You are now our little sissy play thing. You will attend to us when we call for you. You will find ways to show us how desperately you want to please us. When the call comes for you Missy, you had best not displease us." With that they left me to my shame and despair and the knowledge that my life had changed. Forever.

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AnonymousAnonymousover 2 years ago

Im Paul but also Paula im a sissy and love being a sexy slut and i really am a slut who has done most things as far as sex goes except scat i wont do that. I have been with couples who use me for their pleasure and enjoy it as much as being with guys i meet in carparks who just want to fuck a sissy to see what its like. I have no hang ups about age indeed some of the older men that have taken my sissy ass have been very good and i find that married men are some of the hornier and best sex probably because their wives dont suck them and swallow or give them the anal sex anymore. Iv had a lot of compliments about my cocksucking skills from men like i wish my gf/wife would suck me like that and have been told fucking my ass is heaven to them. Having sex with a couple is hot and i enjoy having my ass being fucked by a man while women watch and some women love it a lot. Iv had a lot of strange requests and fulfilled a lot of fantasies for men and women some i would not repeat here but have enjoyed everything iv done and going home with a mans semen inside me always brings a smile to my face

albert1eralbert1erover 3 years ago
Great

I really enjoyed it. Well done.

louiseacdlouiseacdover 3 years ago
hot

i always dreamed of that happening to me

prybarprybaralmost 8 years ago
love it

love the story, good work.

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