By Wee willy winkie.
“Put them on!” she ordered, waving a pair of particularly feminine panties in my direction. I glanced at her face nervously, secretly desiring the whiff of kinkiness she offered but afraid she might use it against me.
“W-what do you mean?” I asked, still uncertain what it was she wanted, this strange, strong and oh-so-still sexually desirable woman who had enraptured me for so many years. This was a bit of a departure from her normal behavior, our sex life was good, wild at times, but this wasn’t our usual scene.
“Don’t pretend you haven’t thought about it,” she winked “I’ve seen the way you look at me when I’m putting my underwear on, it’s not just admiration of me, though I’m well aware I still get you hard. But, you know, thinking about you in panties actually gets me wet. I’ve always wanted a little dolly to play with, and it looks like you’re it.”
I was happy to get away from drawing any more awkward comments about my own interest in women’s underthings. I just nodded dumbly.
“And you needn’t think nobody else knows either, Jane saw you looking through that website on your phone the other day, you should have seen the face she made over your shoulder. I told her, when you went off to the loo, that I think you’re just trying to compensate for having such a tiny penis.”
“W-what?” I stammered again, blushing furiously, stunned that my wife was not only trying to get me to dress like a woman but was also telling me she was unhappy with my manhood. What was going on? Dissembling, I managed to mumble “My penis? There’s nothing wrong with my cock. No-one’s ever had any complaints before.”
The scorn in my wife’s voice was suddenly thick and brutal. “They just didn’t want to hurt your feelings pee-wee, and don’t let’s pretend that what you have between your legs is a cock. Only real men have one of those. I called your shrunken little worm a ‘penis’ because that’s what a little boy has. It must have been really hard for you in school when all the other boys were growing up, and you were just left with that pathetic thing!”
Hard was about right. Inexplicably my wife’s scorn and humiliation of me was having a genuine effect on my manhood, blood pumped into my shaft, and it began to stiffen.
“Hahaha look at it! Pathetic little thing! It seems like you like to be reminded of your shortcomings,” Joy rejoined, “God, why I ever let you put that up me is beyond me. I was just stunned for ages, I think, the first time we fucked, and I was actually sober. I just couldn’t believe they came in such a small size. Seriously, compared to my previous boyfriend,s I struggled even to feel you.”
“Then why did you even marry me then? ” I sulked at her.
“You know full well I’ve never met anyone as good at licking pussy like you, which makes sense now I think on it because you are so shit in the dick department. Besides, I know you’ll almost always do as you’re told, and you are still attractive, just so long as I don’t have to look at your mini-milk.”
“Oh erm, hey, I’m sorry, I’m not built like some porn star or something… ”
“Yeah, me too, tiny-tinkle, now stop fucking me about and put these panties on, if you’re going to have a tool that’s that small, it’s about time we faced up to the fact that you’re more woman than man, we can deal with that, but I’m afraid you’ll just have to trust me and do what I say for a while, in the end, we’ll both be happier.”
Feeling utterly dumbfounded, I took the proffered pants and looked at them. They were pink, of course, with a centimeter of lace trim at both legs and waist, bigger than my wife’s usual ones, I thought.
“Don’t worry they’ll fit just fine,” she said as I held them against myself in bemusement, “your little package will be lovely and snug, and they’ll be a reminder for you to stay in your place… that’s below my pussy, in case you forgot! ” she winked at me again, and gave me a little tap on the arse as she walked past me, any further objections I might have had were already irrelevant to her.
Still naked, I stepped first, then the other leg into the pants, slowly drawing them up over my thighs. I was very conscious of the soft friction they produced as I slid them up, brushing against me like a lover’s caress. Nervously I glanced over my shoulder at my wife.
“Good boy. Now turn around and let me have a look at you…yes, excellent, you could do with a little tidying up, but it’s pretty difficult to tell that you’ve even got a thing in there.”
I glanced down, cheeks burning, and sure enough, my wife’s comments seemed true. The tight fabric of the lingerie pushed my cock into my body, flattening it almost as if I just had the mons typical of women. And it felt good too, secure somehow and comforting like something was giving my crotch a big hug!
“And now this.” Joy was handing me what was clearly a matching bra.
“Look, I haven’t exactly got much to put in that have I?”
“Just do it huh? Get it on and then you can get off to work. ”
“Oh that’s the deal is it?” I said as I began to fumble at the clasp of the bra, “you want me to wear this stuff under my clothes all day.”
“Well done darling, you seem to be catching up at last, oh and while I remember, no rubbing yourself off in the toilets at work,”
“I never… ”
“Maybe not, but wearing girly things may get you more excited. ”
I pulled on the rest of my clothes, a shirt, tie, and suit jacket, which would at least cover up any tell-tale straplines, and stumbled off to work.
I soon got caught up in the day and forgot all about my illicit underwear, just the odd pull at my shoulder when I reached for something at my desk giving me a little reminder. It was soon enough, it was time to head home again, and climbing into my car, I started to daydream about what had happened that morning and what Joy might have in mind for us in the future. Being first home, as usual, I made a start on dinner, had a quick run, a shower, and then finished off preparing the evening meal.
“Hi, honey,” Joy called as she came in through the door.
“Hi, your dinner’s just ready” I called back, adding the finishing touches to the evening’s creation.
“Good, I’m starving! Oh, and I…Oh!”
I looked round to see a disapproving look on my wife’s face and glanced down at myself to see what I might have dropped on my clothes as I made the food.
“Who gave you permission to wear those?” Joy demanded.
I realized that after my shower I’d just pulled on my usual shorts and t-shirt and that after the morning’s ‘dressing lesson’ she was maybe a little disappointed. But, disappointed clearly wasn’t the word.
“What the did I tell you earlier?” she demanded “You’re supposed to be dressed as I said, not in those men’s clothes, now get the fuck upstairs you little prick and get dressed!” she was shouting at me now, a rare display of temper that threw me with its vehemence.
“Shit, sorry I forgot.” I apologized, not even sure why I was doing so, “I’ll go and do it now.” I hustled up the stairs and pulled on the slinky items I’d abandoned earlier. I’d actually forgotten how sexy they felt, and as I came downstairs in them, Joy seemed much calmer, smiled, and reached into her bag to hand me something.
“Here, I got you this to wear too for when you’re cooking for me, much more feminine than that old apron you usually put on.”
I looked down into my hands and tried to figure out what she was talking about. Then, shaking out the fabric I realized that she’d got me a flowery, frilly apron that looked like something out of the 1950s…what the fuck?
“What do you want me to do with this?” I asked, still confused about what the hell I was doing. I stood in my own kitchen wearing a lady’s bra and pants with a comedy pinny in my hands.
“Put it on, of course, sillies. You don’t want to spill anything down your nice new underwear or burn yourself or anything.”
Bemused, I pulled the garment over my head and tied it tight around my waist.
“See? Perfect,” Joy smiled at me, smoothing down the front of my apron and standing on tip-toes to plant a peck on my lips, observed, “That’s much, much more you.”
Chapter 2 A New Normal
The next few weeks became increasingly bizarre as all sorts of items started appearing in my clothes drawers. Most obvious was the underwear, more and more slinky, lacy, and, on a girl at least, sexy items started to displace my normal boxer shorts and t-shirts. Soon enough, Joy had left just one set of men’s underwear in my wardrobe, also leaving (written) instructions that it was only to be worn in case of doctors’ appointments and the like.
It was all a bit of a head-fuck. On the one hand, I was constantly titillated by my wife’s intense focus on my groin and what it was wrapped in, on the other I was the pretty rabbit in the headlights. What I should have been doing was putting my foot down and telling my wife that I wasn’t willing to be her sexual plaything at the expense of my own self-image but the truth was I’d never been able to tell my wife anything. She was the boss and
Otherwise, life continued much as before, though our sex life seemed subtly changed too. Whereas before Joy and I had what might be termed a ‘normal’ relationship, she now seemed more aroused when she was around me, particularly when she caught sight of me in my underwear. Foreplay had also become a thing of the past. Instead, at all sorts of incongruous times, she would simply grab me by the head, push down her underwear (when she chose to wear any at all), and pull my head into her sweet pussy, demanding that I lick her to orgasm.
That’s not quite all that changed in the bedroom department. My own satisfaction seemed to become more incidental to the entire process. Whereas before she would graciously allow me to climb on top of her and penetrate her until I climaxed (sometimes lying so unresponsive I suspected she’d fallen asleep), my wife now shied away from this, agreeing only to look on occasionally whilst I fumbled myself clumsily to my own orgasm. She continued to refer to me during the couple of times she did this, or whenever she saw me naked, as ‘pee-wee’, ‘micro-penis’ and even, after a tough run in the cold as I stripped off for a shower, as ‘dickless wonder ‘. Much, it seemed, to her amusement.
As time went on, the combination of wearing soft, silky fabrics and of increasingly being limited in sexual release left me in a permanent state of semi-arousal. The moratorium on work-time wanking, which I would never have engaged in any way for fear of being caught, had now been extended to me being banned from masturbation at any time, the one occasion that she’d caught me tugging away as I lay beside her late at night, believing her asleep, she had, wordlessly and repeatedly slapped me in the balls so hard my ardor quickly cooled.
Eventually, I determined to confront her about it. I was happy to cater to her little sexual kinks to a certain extent. I could tell by the moisture levels of her pussy whenever she forced me down on her that something about this scene really got her hot, but her current intent seemed to be to emasculate me totally!
“Emasculate?” she asked in a puzzled tone after I’d made her a special dinner, complete with wine and a special chocolate desert, and finally got round to bringing up the subject. “How could I do that? You’re not really a man.”
“Really darling, I appreciate your little joke,” I replied, smiling in what I hoped was a reassuring way, “but as much as I might have my failings, I’m not really a woman. I’m a man, and whilst my cock might not be quite up to your standards in such things, all this wearing women’s clothes and behaving like your domestic slave isn’t really right for our marriage, it’s going to cause arguments and…”
“Are you saying you’re unhappy?”
“Well, no, well not really unhappy, apart from the sex maybe but…”
“But what? You do enjoy your new clothes, don’t you?
“Look, darling, it’s like this. Like it or not, I don’t consider your penis enough of a sexual instrument to make you a man. I actually prefer oral sex with you to having you grunting away on me like a rutting hog, and I’ve always been somewhat ambivalent about the gender of the person I have sex with. I earn more money than you. Diminutive sexual organs aside in what way am I not more like the man and you like the woman in this relationship?”
“Well…er…because…” I found myself a bit flummoxed by all this. I’d always prided myself on promoting equality within our relationship, or at least equal enough that Joy didn’t feel like the household drudge, but all of a sudden she’d switched the tables so fast, or so it seemed, that I didn’t quite know how I could persuade her that I was no longer willing to pretend to be a woman for her.
“Well then!” She interrupted before I’d really had time to think out what to say next, “…and don’t worry about the sex thing, I’ve been waiting for us to have this conversation, and I’ve got just the thing to make everything OK.”
‘Great!’ I thought, I’d somehow got through to her after all, though soon enough it became clear that her idea of a resolution and my own were some distance apart. So we spent the rest of the evening cuddling together on the sofa before she took me by the hand (encouragingly early I thought at the time) and led me upstairs.
“OK sexy, let’s get those things off you,” she tugged playfully at that day’s panties, a fairly simple black mesh pair with matching bra she’d laid out for me that morning, “into the shower with you, and hey, since you’re there, how about you give your face a really close shave? So I can really get close to you when you lick me out later?”
More than pleased, I hurried to comply, shaving with the sharp new blades she handed me, careful to lather up well and taking my time getting rid of all of my facial stubble. Soon, I was luxuriating in soap suds as I washed my hair and body, Joy watching me all the time, waiting with what looked very much like eagerness for me to finish off and join her.
“Now darling, one more thing,” she smiled, pulling away from the towel as I reached for it and giving me her best impish wink.
“Ha! OK, what?” I asked, knowing that the night was young. We were both off work the next day and hoping for a little in-shower action together.
Reaching down to her feet, she produced a tube of some ungent or other. She was always getting me to wear some face cream or eye serum or something. Reading the label, I could see that this time it was actually Nair’s hair remover…well, it was a new one, but what the hell? “Yeah OK, where do you want me to put it?”
“All over, please sweetie, legs, chest, groin, arse everything. I want to see you smooth tonight.”
Shrugging, I got on with it, smoothing the smelly white chemical all over myself, carefully making sure I was totally covered. Whilst never exactly a hirsute individual, I’d always been rather proud of my little bit of chest hair, but whatever, I figured it would grow back.
“Excellent!” she said as I finished, covered now like some sort of Aboriginal bushman in sticky white goo. “We just need to wait ten minutes or so, and you’ll be all ready for me!”
Nodding agreeably I stood there for a while, freezing my nuts off but not wanting to jeopardize her new-found good mood since she was being so reasonable for a change.
“Now rinse yourself off,” she said eventually, reading the label closely,” but it says here you need to soap up first then stand for a few minutes under freezing water so that your pores shrink and you feel smooth all over.”
Shivering, I got down to it, first with warm water and soap but then spending what felt like a good ten minutes under an ice-cold stream, thinking that if nothing else this would do my calves, always aching from running, a bit of good.
“Fabulous!” she exclaimed when I was all done at last. “And look!” she ordered me, sitting down opposite me and hiking up her skirt. She wasn’t wearing any pants, and she pulled her pussy lips wide with her finger to give me a good look at her always large clit. “Your little penis looks just like my clit now! All that fuss from you when all along you just needed to cool it down a little! Now your little clitty looks just right.”
Horrified, I looked down at my cock. Sure enough, it had shrunk back into my body. Even my balls looked tiny as they hugged close to my body. Just the very head of my knob protruded from the smooth flesh surrounding it. Oh no, she’d just done this so she could humiliate me some more!
Furious, I stepped from the shower and grabbed at a towel, scrubbing myself dry and fuming at my wife’s continual attempts to make me feel small.
“Oh, I’m sorry darling, I didn’t mean to upset you,” she said sweetly, apparently genuine concern on her face “here, you’d better put this on. It’ll help after that, Imac, stop you from getting spots or anything.”
“What is it?” I growled, no longer willing to play her games.
“Just a little moisturizer, honest, it’ll help stop your skin getting dry after all those chemicals. And it smells nice too.”
Not caring in the least to smell like an old lady but certain I didn’t want to end up covered in a rash, I took the cream and began to smooth it across my newly hairless skin. Grudgingly, I mentally agreed to myself that it did seem to stop the slight burning in my flesh that the hair remover had instigated, and the smoothness of my skin, though weird, reminded me of Joy’s when she had me run a hand up her legs.
Finally, I had finished my enforced beauty routine, and thinking that maybe I’d been guilty of taking myself a little too seriously, I followed her into our bedroom.
“Sit down and relax honey, I’ve got something extra special for you,” she said, patting the bed and passing me the glass of wine that had magically appeared in her hand.
Worried about what her ‘something extra special’ might entail, I nevertheless flopped myself down on the bed, the wine I’d had earlier probably contributing to my feelings that it was pointless to protest.
“Now, sweetheart, I know that you’ve been struggling with the changes around here lately, but believe me, I know what’s best for us both,” she stroked my back gently, soothing my frustration at being treated so harshly, “Now you’re ready I’m going to give you that special treat you deserve, close your eyes… ”
I did as she bid me, hoping that perhaps for the first time in months, she might mount me herself or even take my cock into her mouth.
I opened my eyes again to see her showing me yet more women’s clothing, this time some sort of satin and lace arrangement in peach, with bows, ribbons and other frills.
“Now you just pop this on, and I’ll be right back, and don’t forget the cute little panties.”
When she returned, I was just pulling the last item on, “Beautiful! ” she purred, passing me a matching garter belt, stockings, and what looked disturbingly like a pair of chicken fillets, “now I’ll just help you with these!”
Next, she got her make-up bag and, chatting amiably about the color of my eyes, how certain sorts of clothing complimented my figure and how she liked to see me look my best, she proceeded to paint my face, adding a thick layer of the reddest of lipsticks to match her own and even applying varnish to my nails.
“Just a couple more things, and we’re all done,” she said, wandering from the room again and then watching me struggle into a black full-length frock and topping the whole ensemble off with a long brown wig.
“There you go, gorgeous. Have a look at yourself in the mirror. ”
I got slowly to my feet, all this time during my ‘makeover’ having quaffed liberally from the bottle of wine. What I saw in the mirror wasn’t exactly my idea of a beautiful woman, more like mutton dressed as lamb, or maybe ram dressed as who-knew-what, but Joy certainly seemed pleased with her creation. If I was honest with myself, though, I did kind of like it. I could feel the satin of my panties rubbing against the end of my little cock as I moved. The dress swished around my legs agreeably and the heavy makeup made me feel just plain slutty. But, at the same time, I just felt such a wimp for letting her do this to me.
“Now, stand over there by the door and let me look at you” she ordered, indicating that I should give her a little twirl. Feeling a little uncomfortable I followed her instruction, blushing bright red at being made to behave like a performing doll.
“Not bad girly-boy” she breathed, “now you look just like my kind of girlfriend. How about lifting your skirt for me a little? ”
I did it, of course, I didn’t feel there was much more she could put me through, though I was so ashamed I could no longer look her in the face. What was worse, the weirdness of the situation added to the fact that Joy was idly fondling herself as she watched me was getting my emotions somehow all confused in my head. Although, despite the horror I was sure I should be feeling at what had been done to me, I was undoubtedly also feeling somewhat aroused, my cock straining at the fabric of my skimpy, pretty pants.
“Ha! I thought so! You filthy little tart,” Joy laughed at me, “your little clitty is all hard, isn’t it? Well, answer me, slut, isn’t it?”
Miserably, I nodded my head and mumbled something unintelligible.
“Pull those pants down to your knees!”
Knowing exactly what she meant and grasping the sides of my peach panties, I pulled them slowly down, straightening slowly with my skirt pulled high once more.
Sniggering, she pointed at my stiff cock, “That is just pathetic! And to think that’s as big as you’re ever going to get. Pull back your little clit’s hood, and let me see the end!”
Taking the end in my finger and thumb I peeled back my foreskin, a sticky, slimy noise coming from my grip.
“Hmmm, nice and wet for me, aren’t you slut?” she giggled again, causing a thrill of sensation to pulse through me, “Pull them back up and come and sit over here.”
I did as I was told, knowing that whatever happened now Joy had decided that it was time to move on to the evening’s main entertainment.
As I sat beside her, she smiled reassuringly, running a hand across my stockings whilst the other arm pulled me into an embrace.
“You know, you don’t have to pretend that you don’t like this anymore” she spoke quietly, seriously, into my eyes, “I can see just how much happier you’ve been these past few weeks and I just want you to know that I love you this way.”
Leaning into my body she planted a soft kiss on my lips, as our matching lipstick mingled her tongue probed my mouth, intimately tasting and caressing. I moaned softly with pleasure and arousal as she pushed me gently to the bed, rubbing firmly at the bulge beneath my dress. She pulled up her own skirt and straddled my face.
“Stick your tongue out,” she instructed, reaching down to spread her lips and display her stiff clit once more. She pressed her pussy down, and the slight tingle of her wetness on my freshly shaved chin and the slippery sensation of her wet pussy made her own arousal plain.
She began to rub herself on the tip of my tongue, “mmmmmm that’s a good girl” she encouraged, eyes fixed on the sight of my shiny red lips as I began to suckle eagerly on her hard, pulsating nerve-endings “suck me off!”
Soon, she was humping determinedly, on my face, grinding herself on my smoothness as her pussy spread on the point of my chin, squelching each time she drove herself onto its blunt width.
“Yes! Suck it tart, suck it until I come on your face!”
I was grunting now, aware too that I could feel the tight pull of my girl’s pants, rubbing around the head of my throbbing cock. Joy’s face flushed as she began to tense into the beginnings of her orgasm.
Reaching back and under the hem of my dress, she grasped at my groin and squeezed hard as she ground her sex into me, mashing my balls and cock together in her hand. A moaning sound came from her, mixing in my head with the agony and urgent, throbbing ecstasy from my imprisoned manhood.
“Oh god, yes, you filthy little slut, I’m coming right on your face!” she shouted, grabbing my bewigged head with her hand and humping herself to panting completion.
Exhausted, she toppled from her seat as the blood slowly returned from her inflamed genitals to the rest of her body. “Honestly, honey, that was the best one ever!” she announced, “you were so good, in fact, that I’m going to let you cum too.”
“What you mean we can actually…?”
“No darling, I told you, you’re not putting that little thing inside me. Stand up over there again and get it out if you want. I want to watch to see that you’re doing it properly.”
Desperate for some relief from the throbbing urgency of my cock I complied, getting to my feet and pulling my girl pants down swiftly, my need obvious from the twitching of my stiff shaft.
“Take that little clit of yours in your fingertips and rub it,” she instructed. “You know, I always like to watch you make yourself cum, I always wonder if you think about what it would be like if you were a proper man. So rub your little tiny penis, and we’ll see if you can get any cum out of it.”
The conditioning of the past few weeks, as she constantly told me how small my cock really was, was taking its toll. Far from being turned off by her belittlement and humiliation of me, my sexuality was getting caught up with the disgust she quite obviously felt towards my disappointing endowment. As she continued to point out why my cock would never be sufficient to satisfy her, I began to feel my orgasm build in my balls.
“Come here!” she ordered, gesturing that she wanted me to stand directly before her as I tugged, desperately at myself, “I want you to wank whatever pathetic jizz you can manage into this.”
She cupped her hand beneath my swollen cock-head, “Get on with it, you sad little dickless whore”
Being ordered to cum for her took me over the edge immediately. Rubbing at myself urgently, I groaned in fulfillment and shot my hot load into her palm, pushing my cock back and forth through my fingers with thrusting hips. As the gorgeous feelings in my cock subsided, I looked down to see a white pool of sperm cupped in her hand.
“Not much of it is there?” she sneered, staring down at the product of my fevered self-abuse. “Now you’re going to lick this shit off my hand. You sissy dress-wearing bitch.”
Noticing my reluctance to taste my own cum, she dragged me to my knees and forced my mouth into her hand. “Eat it dicklet. All girls have to sooner or later.”
I licked tentatively at the cooling pool of sticky slime. It tasted strange, slippery, and musty on my tongue.
“Lick it up, or that’s the last time you get to play with your little boy clit” she informed me, tipping up her hand, so the gelid mess slid into my mouth.
“Now,” she said perkily, “get your panties back up and go and make me a cup of tea. All this watching you play with your tiny little thing has made me very, very thirsty.”
I wandered downstairs and put the kettle on to boil in a post-orgasmic haze, filling the teapot and spooning sugar whilst I tried to make sense of what my wife seemed to want from me. Then, shaking my head, I took the tea upstairs and prepared for what I was sure would be more humiliation and domination. As I approached the bedroom door, I could hear what were unmistakably the sounds of sex coming from inside. Had someone else been here all along?
I peered through the crack in the door. Joy lay on her back with her legs spread wide, briskly pushing a large dildo in and out of her wet pussy, it was obvious that she was enjoying herself tremendously.
She paused. “I know you’re there sweetie, come in here I want you to see.” I stepped through the door and placed the tea on the side. “Stand there like a good girl and watch how a woman takes a real cock.”
Undoubtedly, the rubber tool she was accommodating inside her was considerably larger than my own package. I could see her flesh stretched wide around the thick shaft, which even seemed to bow a little each time she pushed it into herself, showing the force she needed to apply. She was grunting, quietly, each time the fat head of the dildo slipped into her eager hole. The whole time she was looking into my eyes to make it quite clear to me what she meant.
“It seems like so long since I had a real man’s cock inside me, filling up my nice tight pussy” she sighed, her pace quickening as her hole, stretched wide, began to respond to the thrusting of the thick phallus “you could never fill me with your tiny little excuse for a dick, you need to understand that only a proper cock can really satisfy me.”
Grunting, she banged the dildo into herself frenziedly, clutching at her beautiful tits as finally, her orgasm hit “you pathetic little no-dick!” she panted, thrusting herself onto the surrogate cock as she took herself over the edge, bucking her hips in ecstasy and then, finally, exhaling with satisfaction and relaxing back onto the bed.
Satisfied, she allowed me into the bed myself, happy to use me for emotional comfort just as easily as she had used my tongue and her dildo for pleasure. Exhausted myself and still feeling the effects of the wine I soon drifted off to sleep
To be continued…
*This story has been edited to fix spelling, punctuation, & basic grammar, but the narrative and plot have remained the same. Just remember, even with the limited editing we do, it doesn’t mean any possible major flaws in this story were fixed.