There is a weird and somewhat surreal thought exercise I like to engage in while sitting here in front of my company issued perfectly adequate yet utterly uninteresting laptop, over-hearing our office manager complaining again about people not refilling what I consider the world’s most inoffensively generic pot of mediocre coffee. I wonder ‘Am I the only kinky bastard in this room right now?’.
The high strung office manager with her ‘I want to talk to your manager’ haircut, has she ever been on the business end of a flogger? Jim in accounting, does he have some kind of smoking hot wife at home whom he just utterly dominates when he gets home, swapping his blue short sleeve button up shirt for a supple leather vest and single tail whip? My boss Kathy, with her exhausted eyes and comfortable but cheap shoes, does she have some titillating memories of the heady days of carefree left coast college explorative sex adventures?
I can never focus on mornings like this. Every time I shift ever so slightly in my chair and I feel the delicious soreness in my ass I’m taken right back to the bedroom where less than 12 hours ago I was embroiled in the hottest, steamiest, kink fueled romp you could imagine. It’s a good thing I already have my caffeinated swill because if I had to get up I’d look like a prepubescent boy being asked to solve a math problem in front of the class with an uncontrolled erection pitching a khaki tent.
Surely I can’t be the only man in this office wearing a pair of silk purple panties under his sensible office wear. My wife left these on the bed with a note that read ‘To remind you of last night’ punctuated with a little heart before she left for work. Not that I need much of a reminder, it’s all I can think about.
Yesterday morning started off like most mornings. I snuck in a run before starting to get ready for work and Kelly had an early errand she had to take care of so we said our goodbyes and parted with a slightly more passionate than normal kiss as I made my way to take a nice hot shower. Exiting the shower and heading back to the bedroom to get dressed I see my clothes for the day layed on the bed with a pair of satin black lace panties with a yellow Post-it note that read ‘tonight you’re mine’ in her unmistakably tidy handwriting.
A warm wave of excitement washed over me, what did she have planned? Would I have to wait a full 10 hours before she gave me any clues as to what our night had in store?
I opted not to say anything about it over text so not to ruin the surprise but I couldn’t have been more distracted throughout my day of compiling spreadsheets and general corporate busy work. I could win an Academy Award for my performance in office conversations where I look perfectly engaged but in my mind I’m 22.4 miles away indulging gorgeous wife’s every whim.
Just before lunch as I take my sandwich out of the bag she sends me a seemingly innocent text of “I heard that Steely Dan song on the radio that you like so much and I thought of you <3”. My heart leapt into my throat and the morning’s tingle came over me again. We learned a long time ago after a near exposure in a presentation about quarterly earnings where I had my screen shared that when we’re planning an evening’s kinky adventure it’s best to work in code. Casually mentioning Steely Dan’s song ‘Peg’ is a good way of telling me that my ass is hers tonight to do what she pleases with. A second text comes just before I head home telling me that she picked up some ‘lovely RED wine to have with dinner’ giving me some vague insight into the attire for the evening.
When you’ve been in perpetual state of unbelievable lust for an entire work day extra traffic on the way home is like some kind of cruel punishment but I hear the anticipation makes it better even if it is frustrating as hell.
I park my car in the garage and make my way towards the door where another Post-It note is waiting for me that says ‘Go upstairs and freshen up, I’m in the living room’.
I make my way to the guest bathroom to take a shower and find a glass of red wine on the counter by the sink, a classy bit of liquid courage to help calm down the excited nerves she knows I’ve probably had all day long. Getting undressed I spend an extra few moments taking off the panties that have kept my attention focused on her plan all day and I take a quick but thorough shower whereas to not keep my lovely bride waiting any longer.
Stepping from the bathroom into the guest bedroom I see displayed on the bed for me a pair of vibrant red 5” patent leather pumps with the ankle strap, a pair of white silk seamed stockings and matching garter belt, a rather tiny white thong and a red dress just a shade darker than the shoes. “That is what she meant by ‘RED’ wine!” I think to myself as I start to get dressed in this wonderful outfit.
There is generally nothing feminine about me. There is zero chance I could pass for female in the open world but my loving wife knows that I have an absolute kink for crossdressing and the tactile feel of high quality stockings sends my senses over the moon. I’m neither gay nor bi (heteroflexible at best) and I’m happily cis-gendered in my masculine male form as born, I just really like the look and feel of my little kink. We kind of eased into dress play a few years ago and it has become an occasional thing we like to engage in with a frequency enough to satisfy my desires but not too common to take the taboo excitement out of it. What started out as her indulging one of my deepest secrets has turned into a great roleplay adventure that we both thoroughly love to engage in.
After a day of walking in your average men’s business casual leather shoes navigating a set of stairs in 5” heels is an exercise in absolute concentration. When we first started playing like this I had all of the grace of a newborn gazelle but time and practice have gifted me a fairly lovely narrow heel-toe gait where each metered step lands shortly in front of the other.
The sound of my own heels rapping on the hardwoods echo thoughts of one of my favorite taboos as I make my way towards my wife sitting on the couch.
I had once expressed an interest in some more advanced roleplaying where I would serve as the wife one evening and she the husband, punctuating our evening with some intense role reversal love making and I see that tonight she wanted to fulfill that fantasy for me completely.
She stands up and starts walking towards me, wearing a slightly too large dress shirt, jeans, sneakers, and her hair tucked under one of my baseball caps. I can see the unmistakable bulge of a massive latex cock going down the left side of her jeans. I lean down to kiss her and she pulls away with a ‘not yet’ finger to my lips (I’m already 3” taller than she is and now with the towering heels I’m borderline looming) saying “I knew you’d forget your lipstick” handing me a tube that matches my shoes.
Lips now as red a new Ferrari she begins to walk around me in a slow circle, drinking in every inch of me. Despite having dressed up for her several times I still have a hard time completely letting go of all of the years of social programming that kept my secret hidden away and my nerves start to come back fully. As quickly as they come on they are assuaged with a soft and breathy ‘God you have beautiful legs!’, running her hand softly up the seam in my stockings, dragging a languid finger under the garter strap, ending with a warm playful slap across my right ass cheek. The dress she picked for me lands at exactly the top of the stockings so I give her a little playful twirl to show her my outfit.
“Alexa, play evening playlist”
Softly a sexy salsa number begins to play throughout the house and we grasp hands and begin to dance. Every motion feels so deliberate in my unfamiliar heels and the longer we dance in no particular style the more we immerse ourselves in our respective alter-egos. My soul is filled to the brim with appreciation and love for this moment for my gorgeous wife is not only indulging me in one of my deepest fantasies but is making me feel so incredibly sexy as she looks at me with the same hungry eyes that I have for her.
With the changing of the songs we pull close and begin an impassioned kiss, neither of us wanting to rush this moment but the power of our desire is quickly eroding any control we possess.
We make our way to the bedroom where in the middle of the room is one of our dining room chairs. She walks confidently to the chair, sits down with a more masculine ‘ankle over knee’ versus ‘knee over knee’ style that she usually uses and with a cheshire cat grin tells me “I want you to dance for me”.
I had hardly consciously noticed the genre change in the music but fortunately my hips had already synced with the beat of Chris Isaak’s ‘Baby Did a Bad Bad Thing’. She sat casually attentive in her chair as I sauntered around her, dragging a finger across her face and lips, spinning slowly to behind her chair, leaning in to kiss her on the nape of her neck, spinning again to complete my rotation directly in front of her. Trying to remember every sexy stripper dance I had ever seen I spread my legs just outside of hers and ran my hands down and back up the back of my stockings ending with my fingers going into the waistband of my panties.
“Don’t take them off yet” she said softly “I want them on”.
I dipped my ass down and ground her lap, feeling the latex treat awaiting for me as she grabs my hips to help my grinding rhythm. I continue to dance for her for most of the song ending with me straddling her lap and furiously kissing each other. Our hands recklessly exploring each other as our lips couldn’t be pulled apart by a team of wild horses.
She is running her hands up and down my satiny thighs as we make out and I’m cradling her face in my hands. Her fingers trace under the garter straps again, pop out and start to worm me out of my dress.
There is a mutual understanding as we look into each other’s eyes that we simply can’t wait any longer and it is time to escalate to the next level. I sink to my knees on the floor, still leaning in kissing on her wanting lips as I unbutton her shirt revealing her stunning tits in a black cage bra. I kiss all over her chest, put my hands on the small of her back and pull her to the edge of the chair where she leans back for me, exposing her stomach.
Looking up at her as I kiss my way down her stomach I begin to unbutton her jeans. Her breath quickens as I unzip and pull her jeans off, the big surprise of the night springing to attention from her panty harness. Staring me in the face is an 8” flesh colored girthy monster that I’ve never seen before.
It was either instinct powered by my outfit and character or the way her gaze told me more than words could I grasp her giant member in my hand and start giving it deep slow head, Our eyes never broke lock as I took as much of her manhood as I could fit in my mouth. She starts moaning and writhing in her seat, grinding her cock in my mouth.
“Holy fuck this is hot!” she moans when she grabs my hair and starts face fucking me with her newly purchased dick.
After a few minutes of this intense role reversal and what I think is a complete exhaustion of my sissification at my wife’s hands (or dick as it were) she gets up and pulls me to the bed. She had already set the lube and toys out in preparation for the night so when she pushed me down flat she already had lube in her hand to begin warming me up. In all of the passion of the evening I had almost forgotten that my ass was hers but she was now about to take me how she wanted me.
We started with a fair sized butt plug absolutely dripping with lube. She pulls my panties to the side and gave my cock some loving strokes and light brushes as I relaxed to take the heft of the plug. Finally after a few minutes the plug slips in and I feel the fullness of this advanced sized anal play device. Knowing the pounding I’m going to take in a few minutes I’m good letting the plug stretch me for a few so we keep making out, hands and fingers finding every corner of each other’s bodies.
“Are you ready for me?” she whispers, dragging a nibble across my earlobe.
“Please! I NEED you inside me right now” I plea. Not intending to but I notice my voice has a faint feminine quality to it as I beg for her to fuck me.
As she stands there lubing up her cock, still with my lipstick marking the depth my throat could handle, she smiles at me and says “I have been wanting to do this since I ordered this 2 weeks ago!”.
Taking a new toy can be scary especially when it is the size of a fully grown dragon’s tail but her attention to my preparation and my wanton desire made it go in far easier than either of us expected. She took it respectfully slow for me, grinning from ear to ear at the sight of my eyes rolling back in my head in ecstacy. The mid pubis harness gave her a natural stroke from which to enjoy her fucking. After a few minutes of progressively increasing intensity she was absolutely pounding my ass, my legs draped over her shoulders. My high pitched moans surprised me but it was like I had no control of any of my senses anymore. I was in kinky heaven lying under this amazing creature while I wear stunning lingerie, having my asshole reamed.
Her pounding gained intensity still when she, in the same sensory overload as I was feeling, started asking “Do you like that? Me fucking that tight pink ass of yours? Are you my sexy little slut? Tell me you love my big cock! I want my sexy little slut to tell me how much she loves my cock”.
I could only respond in short bursts of agreement and adoration and she fucked me with furious abandon. I could feel the beginning of the prostate orgasm coming. I had never had one before but there was no mistaking the freight train starting deep in my ass and radiating throughout my body as I convulsed in an arch of joy. She slowed her stroke until the first few waves had subsided then slowly pulled her new toy out of me.
“Ho-ly-fuck” I managed to half whisper, half moan to her. “Allow me to return the favor!”
I needed a few minutes for my body to reattach itself to my soul so I pulled her harness panties off and threw them across the room, laid her on her back and started kissing up her legs spending extra time biting the insides of her smooth almost porcelain white thighs. I wanted to savor every moment of this and show her my devout appreciation for everything she had done for me so far that evening. I licked her pussy from top to bottom, left to right, tracing every millimeter of her sex with my tongue, stopping occasionally to give her clit and hood some talented head. She reached her hand down and got a firm handful of hair, pulling my face into her pussy, commanding my oral performance with every nuance that she wanted. As I feasted upon her sopping wetness I could feel her body starting to tense as her first orgasm began to build. I wrapped my arms around her thighs and held on for my life as she screamed loud enough for people in the next county to hear. Bucking and squirming she came for a good 20 seconds before pushing me away by my forehead trying to collect her breath.
I wanted to just crawl on top of her and pound her with the same fervor she had so lovingly given me but she had alternate ideas and since this was completely her show I gladly rolled onto my back for her to straddle my insanely rock hard cock. She pulled my panties off to the side again and crawled on top. We both let out a deep moan as I sunk deeper into my love than I think I have ever been. Rocking back and forth she arched herself backwards so she could rub on my smoothly encased legs. The combination of my tingling asshole, the feel of her hands rubbing my legs, her juicy pussy filled completely with me – it didn’t take long for me to pronounce I was getting close to cumming myself. She slowed her pace to prolong the enjoyment and so she could ask me “would you eat me again after you cum inside me?”. Holy shit she was hitting on so many of my fantasies at once tonight I almost let go right then but I managed to eek out “only if I can kiss you after”. She gave me a sly smile and worked me in the way that only a couple that has been having sex together for decades knows how to do.
My entire body tried to fold itself in half as I let go an orgasm that dug my heels into the bed, my hands grip her hips to keep her from flying away and a cry of unrestrained pleasure.
She slowly gave me a few more rotations of her hips to milk the last few blessed drops out, then lifted herself up to let my spent throbbing member fall out of her. Giving a few kegel squeezes she coated my balls and shaft with most of my mammoth load, reaching down behind her to rub my scrotum and cum soaked panties together. With determined purpose she crawled over me and planted her incredibly warm pussy on my still gasping mouth. I have always loved the way her pussy tastes after I’ve fucked her hard and mixed with the remainder of my own cum it was even sweeter and more decadently depraved. She sat on my face, grinding like a woman on a mission, our juices flowing all of my face and chin. I could feel the big O trembles starting in her legs again and she screamed out “I’m about to cum again!!!” and had her second massive orgasm of the night. I kept licking and sucking for as long as she could stand it before she was too tender to go on.
Falling to the bed beside me we pulled each other close and started kissing lovingly, our collective orgasms fresh on our lips until we both just collapsed in post coital bliss, panting an appreciative set of breaths as we held each other’s hands, crawling together to snuggle for a good 10 minutes to just bask in the gloriousness of the evening.
So yeah, I don’t think I really needed to wear these panties to work today to remember last night.
Source: reddit.com/r/sexystories/comments/b0kzek/so_about_last_night_mfcrossdressingpegging
Wow! Just, wow.
Hot story. I wish I was in your shoes. So jealous.
Hot story. Love the tenderness yet passion of your wife. Awesome!