Michele Nylons' Stories Ch. 06

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I almost envy her. I am fucking her with long, slow thrusts while she is sucking on an engorged penis. I know that she is in heaven but I'm not being left out of the party either as the man with his finger in my ass begins to drive his pudgy digit in and out my rectum in time with my thrusts as I earnestly fuck the gorgeous crossdresser lying under me.

I am now free to look around and I can see that the crowd at the door is a little bigger. Another man squeezes through the door and begins to stroke my legs, which I greatly appreciate. I am did not select the name Michele Nylons as a whim. I love the feel of hands caressing my nyloned legs and genitals.

My cock is buried deep inside my transvestite lover's anus and I have a man fingering my tight asshole and another stroking my legs. I am in heaven. As is Emily, who is sucking on a hard fat cock while I plow my engorged cock in and out of her tight rectum.

This goes on for a little while but suddenly the man with his cock in Emily's mouth groans and I know he is coming; filling Emily's mouth with a creamy load as she slathers at his manhood. This incites the man playing with my legs while he is wanking himself to extremis and I feel the warm spatter of semen on my calves. The man fingering my asshole surrenders and whips his finger out my ass and scrambles up onto the bed and puts his cock in the crease of my buttocks and I feel his cock judder and the warm succulence of his spend squirting between my buttocks.

I can feel Emily's cock begin to quiver inside her panties and I fuck her hard and fast and soon her panties are flooded with her issue. I feel another spatter of hot cum drench my calves and ankles as another man who was stroking my legs ejaculates. The tiny room reeks of musky semen and perfume.

The Viagra is working well, keeping me hard and my cock is alive with sensuality and pleasure but I'm not through my refractory period and unable to cum. I press it deep inside Emily and feign an orgasm. I'm a little tired and covered in semen and need a rest.

The man who was dry-humped my panty-clad buttocks climbs off the bed and drifts away. The anonymous men who ejaculated over my stocking-sheathed legs have departed, as has the man who blew his load in Emily's mouth. I lie on top of Emily feeling her semen soak through her panties. She is panting with exertion and when she catches her breath I kiss her passionately, tasting semen on her breath as I slowly extricate my still engorged penis from her tight ass.

I climb off Emily and take stock. My legs are covered in semen, the valley between my buttocks is drenched and as a consequence of Emily's orgasm both the front and back of my panties are saturated with sperm.

It's time to clean up and change and Emily has to go to work. We accompany each other to the ablutions and Emily goes into the shower to wash her body, remove her makeup and transform back into the man she presents to the world in her ordinary vanilla life while I take over my favourite toilet and kick off my high heels and step out of my cum-soaked knickers and roll down my cummy nylons.

The semen-drenched stockings and panties go into a Ziploc bag to be laundered when I get home. I clean my body, my buttocks and intimate parts with warm soapy water and dry myself. I open a pack of 15-denier 'Clio Italian Soft Shine Lace Top' stay-up stockings and put them one, smoothing the nylons along my long legs. I step into a pair of black satin full-cut panties and inspect the tulle skirt attached to my chemise and dab at the little patches of damp semen with paper towel.

After fixing my makeup, brushing my hair and spraying myself liberally with deodorant and perfume I'm ready to face the world again but not yet ready to play. I drop the Ziploc baggie in my locker and head back to my room. I close the door and lie on the bed and check my phone for messages and email.

The Glory Holes

I reply to a couple of emails and texts and read a few reviews of my latest story posted on Literotica. It's made the 'hot' list so I am happy. I finish my Coke Zero and take a few sneaky puffs on my vape. I gave up smoking cigarettes a few years ago but still like a 'puff' now and then.

Suddenly I realise that there is a hard cock poking through the glory hole and being a good girl I get up off the bed, get down on my knees and begin to fellate the sturdy appendage. I hear muffled sighs and groans on the other side of the thin plywood laminate. The cock is quivering in my mouth and suddenly it explodes, filling my mouth with salty, musky semen which I gleefully swallow.

"Thanks," comes a muffled reply through the glory hole.

The depleted organ is withdrawn and I get up off my knees and head to the toilet intending to rinse my mouth and apply another coat of lipstick.

This time on a Friday afternoon a lot of 'tradies', skilled tradesmen, have knocked off early and are heading to the pub, some them via The Laneway for a quick blowjob. Many so-called straight tradies take advantage of the discreetly located, dark cruise lounge. They come through the door averting their eyes and head straight for the glory holes where they can imagine it's Katy Perry or some other desirable female celebrity sucking their cock instead of the skinny old man with the goatee or big-bellied biker who is actually on the other side of the wall.

No harm, no foul, everyone is entitled to a Friday afternoon blowjob after work. The tradies can sneak out unseen and head down the pub and tell 'poofter' and 'tranny' jokes with their mates whilst they still have my lipstick on their cocks inside their work shorts.

I stop at the glory holes and fulfil my duties, sucking a few dicks until I get bored with it.

The early afternoon rush is over and the place has thinned out. The troll is being fellated by a young man while he sits back watching gay porn in the lounge and has a smug grin on his face. At least he will go home satisfied.

Anonymous Bearded Guy

Finally arriving at the toilet I rinse my mouth and lean into the mirror to apply lipstick. I always leave the toilet door open because the passageway past the two toilets connecting the main lounge area to the back rooms is always busy and as they say 'it pays to advertise'.

I'm concentrating on getting my lip-line right when I hear a guy at the door.

"Jeeze, I didn't know girls like you came here!" the young man growls.

I focus on my lipstick. I get comments like this quite frequently.

Suddenly the man is behind me. He's thirties, breaded with a beer-belly but not unattractive and there are no pleasantries. He pushes himself up against me whilst nuzzling my neck.

"You smell good," he grunts as he rubs his cock on my panty-clad buttocks.

He's impatient and pulls my panties down my thighs.

"Just let me finish my makeup and we can go to a playroom," I propose, deliberately ignoring his advances and trying not to smudge my lipstick.

It's a waste of time. He manipulates the handle on the liquid soap dispenser mounted on the tiles under the mirror, takes a gloop of liquid soap and pushes his hard cock between my buttocks along with the gloop of soap and pushes.

I grunt as his stiff cock invades my anus. It isn't that big but it's thick and hard. Breaded guy grips my hips and begins to almost rape me. There was no discussion about consent, tacit or otherwise but I am technically dressed as woman in sexy lingerie in a gay cruise lounge so it's not like I can complain.

And I never would with this guy. He nuzzles my neck and strokes my thighs when he's not holding onto my waist as he buggers me with determination. His cock feels quite nice and is the perfect size to press on my prostate and I'm becoming semi-erect. Like the good girl I am I bend my back and push my ass out to meet his thrusts and his fingers dig into the flesh on my generous hips as he viciously shags me.

He's coming and I can feel it. He's grunting, his legs are shaking, his cock is juddering and suddenly he pulls me back hard against his body and holds me close, forcing my head sideways so he can kiss me while he ejaculates his load deep inside my rectum. He holds me imprisoned, pressed against the sink while his cock unloads a torrent of hot viscous spunk inside my anus.

And just like that; he is done. Leaving me with a tingling in my rectum, an assfull of spunk and semi-hard.

He whips his cock out of my ass, turns away and is gone out the door. Zipping his fly he calls out: "thanks luv" and I never see him again.

I take a handful of toilet tissue, clean up the mess between my buttocks and flush it down the toilet. I pull up my panties, finish my lipstick and leave the toilet and head into the main play area.

Leon - Take Two

Back at my room Leon is waiting.

"You've been a busy girl," he chuckles and pulls me into his embrace.

We kiss and fondle each other for a while, enjoying the sensuality of it. Leon's hard cock is out and is he is rubbing it on my thigh while he holds me tight and kisses me. I sense his need but I don't want to have to change my stockings again so I take him in hand and lightly caress his swollen member until I know he is ready.

I drop to my knees and take him in my mouth, sucking on his hard cock and licking his scrotum how I know he likes me to do. He gently moves my head, alternating my lips from his scrotum to his cock in no rush to climax but unable to contain his lust.

I am surprised when a freshet of hot semen splashes across my face. Leon has cum while I was licking his scrotum. I quickly put my mouth on his cock and catch the remainder of his spend in my mouth, sucking his engorged appendage and milking every last drop from it. Leon's knees are shaking and he is moaning; holding my head in his hands while he evacuates his milky seed in my willing mouth.

"You do that so well," a deep, vibrant voice resonates from the doorway.

I finish draining Leon and he helps to me to my feet and hands me some handtowel so that I can dab at the glutinous spunk that he ejaculated across my cheek and nose. A scintilla of it is hanging from my lower eyelash and I carefully wipe it away.

"Sorry Michele, I just couldn't hold back," he apologises and kisses me tenderly.

"Only to be expected," I grin at him cheekily and turn to face the door.

Tom

Tom is in his fifties, tanned, fit and handsome and bollock-naked with his large appendage jutting out from a matte of pubic hair. He likes to fuck young twinks and he's popular amongst that demographic but he doesn't mind fucking an old tranny like me occasionally provided she's good looking and knows what she's doing.

We have been texting back and forth for a few days. He's divorced, or so he says but who cares, and is holidaying at a swank hotel in Port Douglas. He texted me that he was driving down this afternoon but I get so many no-shows that I took it with a grain of salt. But I'm glad that he is true to his word because this big-cocked handsome hunk is just the type of man that does it for me.

Leon is a pragmatist and knows that I will be here again Sunday and the following Friday so he politely leaves the room while I fix my lipstick and makeup as best I can without a mirror.

"Not sure if you look better now or with cum all over your face," Tom chuckles.

"Don't be cheeky," I give him my most salacious smile and he enters my cubicle leaving the door open.

I know this is going to be fun and can hardly wait.

We begin by him taking me in his arms and kissing languorously. Tom is in no rush and he strokes my face and tells me I'm gorgeous which I know I'm not anymore but I accept the compliment graciously and flick my tongue into his mouth. He meets my tongue with his and we kiss a little more passionately and I can feel that hard appendage pressing into my belly.

I snake a hand down there and softly explore his exquisite rod with my fingertips. The shaft is long, sleek and velvety to touch and I trace a finger along one of the many pulsing veins and find his swollen glans which is smooth and spongy and leaking pre-ejaculate.

Tom's hands are cupping my buttocks, gently squeezing them and rubbing my satin panties against my tender flesh. Then he explores my thighs and the feel of his manly hands on my stocking-sheathed legs is amazing. I am rock hard inside my panties. Tom finds me that way and strokes my cock through my knickers and I tremble and feel him smile around the passionate kiss.

We masturbate each other for a while, our lips locked together, our bodies pressed close, enjoying the anticipation of what is to come. He eases me back towards the bed and obliging I lie down and he stands at the edge of the bed with his magnificent cock inches from my eyes.

I guide his manhood to my mouth and I open wide and take it, softly sucking the velvety hard flesh, running my lips up and down the shaft while my tongue tickles his glans and fraenulum. He reaches for my groin and pries my erect penis from my panties and stokes it softly, bringing it to full tumescence.

"I've imagined doing this on the drive all the way down from Port Douglas, you're just like your pictures on Grindr," he compliments me but I'm too busy enjoying the sensation of his cock in my mouth and his soft manipulation of my penis to care.

Leon and a couple of looky-loos are standing at the door watching and wanking. My nightlight is on so they can everything.

Tom lowers his face to my groin and takes my cock into his mouth and we suckle each other for a while, tasting each other's juices which are flowing freely.

Suddenly Tom stops sucking me and pulls his cock from my mouth and spins me around so that he can put my ankles up on his shoulders which forces my buttocks up off the mattress, leaving me exposed and vulnerable. My favourite position.

He manipulates the lubricant dispenser on the wall and greases up his shaft.

"Ready?" he smiles down at me with his handsome face and I nod appreciatively.

He eases aside the gusset of my panties and nestles his glans in my pink puckered bud and pushes. He takes his time and I hold onto his forearms, gazing up into his face, my legs up high on his shoulders as that magnificent specimen of male flesh slowly opens me and enters me.

A wave of intense pleasure washes over me and I sigh and look up and see the look of contentment on Tom's face as his cock slides all the way into my anus. I'm filled. Stuffed to capacity and enjoying every second of it. He smiles down at me and begins to fuck me.

The feeling is indescribable as that long thick cock slides all the way inside me and is then withdrawn until just his glans are ringed by my sphincter and then he drives it back into me all the way until his pubis is pressed against my buttocks. He keeps this up until he is overwhelmed with desire and he quickens the pace.

"Fuck me Tom! Fuck your tranny whore!" I encourage him, my cock presses against his flat belly as he lowers my legs and opens them wide so he lie on top of me and kiss me while he is fucking me.

I hold him close and kiss him fervently as he humps me; his cock is driving me wild with lust, igniting the sensors ringing my sphincter and his shaft and glans kindling the pleasure centres in my anus and prostate. My cock is rubbing on his hard belly and my body is afire with delight and gratification.

He fucks me harder and faster and I raise my buttocks off the bed to meet his thrusts, I cling to him, holding him tight while my mouth is locked to his. I feel him groan and his cock expands and contracts as he plants his seed deep inside me. My cock explodes and I spatter his belly with my issue as an orgasmic high sends me into sensory overload.

I am unaware that one of the looky-loos has climbed on the bed but as I break the kiss to take a breath the man pushes his cock towards my face and I can see the yearning on his face so I obligingly open my lips and take the offered appendage into my mouth where it explodes as soon as I suck it. The appendage is whipped out of my mouth almost as quickly as it was inserted and the man climbs off the bed but Tom is delighted and he lowers his face to mine so he kiss me and taste the fresh semen.

We kiss and caress as our orgasms slowly subside. Tom and I are in no rush and he lies on top of me, kissing me and making small talk while his cock slowly deflates inside me until it falls from my anus with almost audible plop. He has left my sphincter stretched and gaping and I feel his seed and likely that of the bearded pudgy guy leaking from ass and running between my buttocks.

All good things must come to an end and Tom disengages and he climbs off me and helps me to my feet and kisses me some more.

"Are you here Sunday?" he asks and he grins when I non in the affirmative.

Tom heads to the shower and the looky-loos have moved on, leaving me alone. I check the time and it is time to leave. The community care attendant who looks after my mother is due to leave at 5pm. She has sent me a text on my 'vanilla' phone asking me to pick up milk on the way home. The minutiae of my vanilla life invade Michele's life and once again I must revert to being a boring respectable, responsible citizen of the world.

I close and lock the door and undress. I take off my wig, brush it and put it away. I use makeup wipes to wipe away my makeup and then I head to the shower with my towel around my waist. There are still people in the lounge cruising or publicly having sex but they hold no interest for me now.

Freshly showered I stop at my locker, grab my backpack, go back to my room, lock the door and change back into my 'man clothes'. I stop at the service window briefly to say goodbye to Vogue and leave The Laneway. I pick up my car, drive to the market and get milk then I drive home thinking about my experiences today and how I will use them to embellish my stories which I write late at night while my mother is sleeping.

I miss the days when I lived alone and entertained my gentleman friends and other trannies in my well-appointed apartment but The Laneway serves its purpose.

I will be back again on Sunday.

The End

Author's Note: I hope you liked this glimpse into how I live my life. The story above is true with no embellishments added. My real life experiences inform the sex scenes in my Transgender and Crossdresser stories, which constitute the bulk of my work. As always, I appreciate it when readers rate my stories and leave comments. I always respond to private feedback and requests for pictures are nearly always granted. I have pictures of myself at The Laneway should you be interested in seeing them.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
PinkPanties4mePinkPanties4me4 months ago

I live my crossdressing life vicariously through your life stories! I especially loved your encounter with Emily!

MeghanBMeghanB4 months ago

Disregard previous PRIVATE post and trash it, It was meant to go to author and not viewed publicly.

Thanks Meghan

Socalsissy1Socalsissy14 months ago

Another AMAZING story

NikkiTSNikkiTS4 months ago

This was great Michele, thanks for sharing!

AnonymousAnonymous4 months ago

Assume to read your true life adventures again

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Wife's Lingerie Man enjoys being a woman wearing his wife's lingerie.in Transgender & Crossdressers
Masculinity Lost How a straight guy was forced to become a sissy.in Transgender & Crossdressers
The Spirit of Halloween Dressing up for Halloween gets to be spiritually rewarding.in Transgender & Crossdressers
Caught in Nylons by Hotel Manager Caught indulging in my secret private fetish.in Transgender & Crossdressers
Trying on Nadja's Lingerie Pt. 01 From admiring a woman in lingerie to trying it on myself.in Transgender & Crossdressers
More Stories