u/CleanUpCollar

A few years back I was working on an on-site project. An exgirlfriend of mine who knew about my crossdressing was part of the team and occasionally in the site offices.

We got carried away (as usual) and before I knew it most days I ended up wearing some element of her clothing. It could be as simple as wearing one of her belts but the thrill of wearing it during the working day was so much fun.

Later on she wasn't on site as much but she'd still post items for me to wear to the site. Being handed the envelopes by the site administrator must have had me blushing but I could never wait to open them.

This particular day she had sent a pair of PVC hold up stockings that she said were too big for her and she wanted me to try them. My office had windows so not suitable for proof photos but on the other side of a little lobby I had a spare office with the shutters closed.

I took my package and a pair of royal blue lace panties (she kept the bra, she got a kick out of wearing it while I had the bottom part of the set on) from my desk drawer and locked myself in the spare office.

Once I slid the stockings on I was in love....the crinkle the material made with every movement, subtle but unmistakable when you knew. And I loved how the black shiny material clung to my legs.

So when she asked for a photo I got carried away....

I climbed up on the empty desk, laid down on my back and send her a shot of them spread in the air....

And she started directing me. Giving me poses to do, critiquing them, adjusting me, guiding me to the kind of shots she'd send a guy to drive him wild.

It was so much fun, it felt so naughty. Right there in the middle of the working day face down on a desk with my stocking clad legs in the air. The lace panties the only thing separating me from the wooden desk. I couldn't resist a little squirm while I kept sending her shots.

And then I heard them. Footsteps in the lobby. A knock on my office door. Someone just on the other side of the door from where I was half naked and laying on a desk.

It was too much. I blew. Right there. Onto the desk. One of those loads that comes when you've been teasing for so long. It was everywhere.

Post nut clarity hit quick. I told my ex. She sent back a 😈 emoji and the words "I love it, enjoy the clean up".

I'm meeting my long term female friend later. We've been friends since high school. We dated for a little bit but kept occasionally playing for some time after. It's this playing that's my earliest memories of prejacing.

We used to hang out, just the two of us even if one or both of us were dating others. Mainly innocently but occasionally we'd end up in scenarios that would drive me wild without any release. Simple things like being her being pressed up against me all night in a busy bar, holding hands on our way to get a cab after leaving our friends, massages, even just cuddling up while watching a movie.

All of these little teases would occasionally boil over and our go to thing would be when we'd be on the couch and I'd be giving her a hug she'd slowly end up straddling my lap. Fully clothed for both of us, we wouldn't kiss we'd just maintain that hug while she started to grind...

As I write I can picture her straddling me, my hands making their way to her hips while her grinding got more intense. I'd never touch her tits or anything just a simple guide if her hips as she'd rise up on her knees a little to concentrate her grind on my bulge.

Sometimes I could last a little longer depending on what we were both wearing and how thick our clothes were but when she rocked up one day in a miniskirt and it was her panties grinding on my shorts I blew in seconds..

She'd keep grinding, faster and faster to get her orgasm and I'd pretend I was still going rather than admit I'd blown every drop right at the start. I'm sure she knew the truth but she clearly didn't care.

Inspired by a Grindr chat just now...

I live in the countryside, surrounded by farms and the barley is being harvested just across the road right now. Tough, masculine farmers hard at work while I'm laying on the couch just out of their sightline from the cab of the tractors or the combine harvester...

I went with a pink bra and panty set this evening and with a nod to the sunny weather I'm wearing my favourite floral sundress with nude tights and wedges. A little adjustment of my fake boobs and I'm feeling sexy and horny.

So horny that I download Grindr (again) and set my location to approximate before going back to browsing sissy porn on Reddit.

Just as I hear the combine harvester passing in the next field I get a grindr notification. No face/body pic which I would normally ignore but I quickly realise it's a picture of a harvested field, taken from the cab of a tractor 😳 and it says he's 1km away....

Now I'd like to tell you I leaped at the chance but it honestly spooked me so much I deleted it again. I'm so tempted to redownload but right now I'm just imagining what the outcome could be...

My imagination is torn between the entire harvest team getting their pleasure at the end of a long day or this one farmer getting the draining he deserves after a hot and tough day in the fields..

And I think this one Grindr farmer winning out. Just the thought of him going farm to farm for work and seeking out all the countryside sissies. Like a sailor with a girl in each port he could have his harem of cross dressers each awaiting his next working call to their locality.

But I digress. I can almost feel the barley stubble under my wedges as I walk into the field. His tractor and trailer are there, parked amongst the bales. In the middle of the field, far from the road but the large blue machine unmissable.

His grin as he climbs down from the cab puts me at ease. He's rugged, the kind of farmer girls dream of and here I am standing in front of him with my sundress swaying in the wind. My hastily applied makeup and wig make me feel self conscious until he moves a stray strand away from my eye.

And just like that I'm in his arms making out with him. His musk makes me feel weak as his big strong hands roam over my body and squeeze my breasts. He takes me by the hand and leads me to a spot between a few bales where he's laid out a picnic blanket and he pulls me down with him.

His hands are all over me, my sundress hiked up as he grabs my ass in the tights and even with his lips on mine I hear a growl of excitement when he finds my skimpy little lace thong.

My hand struggles with his thick leather belt. Then I'm unbuttoning his blue denim jeans. My pink painted nails untuck his check shirt and then I help him pull down his work stained jeans to his knees.

He puts a big meaty hand on my head, gripping my redhead wig and puts a light pressure downwards.

I don't need to be told twice.

And that's how I found myself on my knees in the field across the road. Leaving red lipstick rings on the cock of a hardworking farmer while the hem of my sundress blew in the wind... and to think those rings will still be there when he's having a few pints with the lads in the pub later, drained from a hard day's graft and drained by the crossdresser across the road...

Hooked up with a girl from work and had an on/off relationship over the years. Kinky as they get. We'd end up working together on a project and invariably end up fooling around. This time she had a new boyfriend though so no real sexual activity just kinky games riling me up.

Went for a drive one lunchtime with her and she handed me a pair of black lace panties. Told me to wrap it around my cock while I drove. The feeling of the lace stuffed into my boxers was bad enough but when she laid her head in my lap on the bumpy road I lasted only seconds...

There's no way she couldn't have noticed me throbbing with her head laid on it and there's no way she would have missed the spreading stain as I walked back into the office but she didn't say a word.

Ping.... ping....ping... His phone keeps beeping while I'm perched on his lap making out with him and his hands are straying underneath my plaid schoolgirl skirt..

He stops. Reaches to the bedside locker and picks it up. "Ugh it's her again" he says as I glimpse a photo of the two of them as the background of his phone. A cute 20 something couple, smiling for the selfie he's taken on what was clearly a couples sun holiday. His toned torso and tussled blonde hair alongside her petite frame and bikini clad little B cup tits.

The perfect college couple. She's met his family, she's cute, bubbly and they love her. They've been dating for a few years, long enough for him to know he loves her but also long enough for him to know she's never going to scratch the surface of his carnal desires..

Which is where I come in. Nearly twice his age, I was surprised when he messaged me on Grindr. I was even more surprised when I learned he had a cute little girlfriend. But that was about a year ago and somehow I've found myself being a very willing participant in this testosterone fuelled college guys fantasies on a very regular basis.

Right now he's ticking "Schoolgirl" off his fantasy bucket list. His vanilla girlfriend refused earlier that day, calling it degrading when he showed her the outfit laid out on his bed. They had a little lovers tiff and she stormed off. She's now obviously apologetic but it's too late, his older crossdressing little secret was only too eager to drive over, park around the corner and slip into his shared rental.

The phone keeps pinging as he tosses it on the bed and gets back to running his strong hand up my legs, over the lace tops of my white hold up stockings and under my skirt. His other hand explores the crisp white crop shirt, cupping my bimbo size fake tits. My bright red lipstick is smeared from making out with him while the entire time I can feel that exceptionally large college dick growing under me.

I stop to flick a strand of my blonde wig from my face and he takes the opportunity to have me stand. I blush as I do, a nearly 40 year old crossdresser, on display for a much younger man. Standing in his bedroom, balanced on my patent black court pumps as he unzips his fly and shrugs off his jeans.

"Turn for me" he huskily commands. I slowly turn, knowing the bottom of my ass cheeks are showing below the schoolgirl miniskirt.

"Stop". Now I know what he's after. He's been buying custom temporary tattoos on Shein for months. They last about a week each and this horny young college boy has been getting off on knowing that I have his name tattooed across my ass everywhere I go. He gets off on knowing that I can't sleep with anyone else without having to explain it. Putting on normal clothes to have a date with a girl is fine but the second sex comes into the equation there's a couple of days of a "cooling off period" as he calls it before I don't have his name on my ass.

"To the window". I do my best to strut across making sure he gets a good view. The pumps are high, the platform raising my ass up as I bend over and rest my arms on the window sill. He dims the lights and opens the curtains.

We've done this before, here, hotels, cars. He loves the thrill of being risky in public. He loves the thought of being caught with his cock buried in an older crossdresser. He knows I'd be mortified so he's emphasized that he'd keep fucking me no matter what.

He's behind me, flipping up my miniskirt over my hips. He pulls my skimpy black mesh thong to one side and slowly, firmly pushes his cock into me. He leans down, cupping both my G cup tits as they hand, taking the weight of them in his big hands, tweaking the prominent nipples. And he starts to pump...

I brace, spreading my legs apart, teetering on the shiny black pumps, the contours of my long legs wrapped in high denier white stockings. My tits begin to sway as he builds up rhythm, I knew being my black lace underwired bra was the correct choice as he begins to really get into fucking me.

And right then, as the sound of his thighs slapping against my ass gets louder, the outdoor security lights trigger. There she is, his cute little girlfriend coming up the driveway. Her fit little body still in her gym gear, tight shorts painted onto her, sports top holding her little breasts firmly. I'm jealous, she's so cute but then again her boyfriend is fucking me..

I know he sees her because he picks up his pace. He leans over me again while pumping faster and faster. It's because he wants to look down on her, the top of her head visible as she knocks on the front door. His hands wrap around my throat as he does, my little black choker squeezed tight. This is what he secretly lives for, pounding a crossdresser old enough to be his father while his "day girlfriend" waits outside.

Harder and harder he goes. I'm surprised she can't hear us. The sound of him slapping against my ass seems loud enough to be heard across the street. She knocks again, calling out his name this time and it's like a switch, I can feel him stiffen. He pulls me from the window, pushes me to my knees and rips the few buttons holding the shirt over my tits while I gaze up at him.

A couple of furious strokes and I find myself being splattered with rope after rope of his warm spunk. My face, my tits, the outfit, even my wig has taken a few strings of his creamy young cum.

He collapses on the bed as I recover on the floor. Good thing I know he's got incredible stamina, I'll barely get to stand up before he's ready to take this schoolgirl for a ride. Outside the security light goes off with a blink. She's gone.

"Walk to the edge" read the message, "hands on the railing". I placed both hands on the cold railing and looked out across the hotel gardens at the opposite block of bedrooms. It was too dark to make out any of the room occupants but I knew he was there somewhere watching me..

He being the tall, dark, ruggedly handsome man I had been besotted with since a chance encounter in a hotel sauna. It had been difficult to maintain the small talk as he sat across from me with a crisp white towel around his waist and his tanned chest dripping in the steam. I'd seen him with his wife at breakfast, they seemed happy but he was clearly the one who kept himself in shape. It was no surprise when I saw him working up a sweat in the hotel gym but nothing prepared me for how fast my heart would beat when he opened the sauna door.

The idle chit chat drifted and I started to get butterflies when I realised he was flirting.. with me! My eyes drifted to his crotch and I could have sworn I saw a bulge forming... and then the door opened and two girls walked in. I nearly fled such was my hurry to leave.

I must have been mistaken, an ice cold shower would bring me back to my senses surely. But as soon as I stepped out I found a note on my clothes with a number and a name "Dan, Sauna".

Laying on my hotel bed later that evening and wearing only a pink babydoll i had finally plucked up the courage to message him. I played it safe, saying who I was and asking if it was one of the girls he had meant to leave the note for. He responded within minutes confirming that he did indeed leave the note for me and that he was very disappointed that our chat had been cut short just as it was getting interesting.

"Interesting?" I responded, "what were we about to discuss?"

"What you were wearing on your balcony last night, you didn't think you were that discreet did you?"

I flushed, looking out the full height glass doors to my balcony. The balcony I had thought was too far and too dimly lit to let anyone see the skimpy lace trimmed babydoll I had worn on it last night. I had wanted to feel the cold night air on my skin, the thrill of the icy wind lifting the silky material. No one would see me, no one would know.

That was evidently untrue....

"I have no idea what you're talking about..." I couldn't just admit it, could I? The fear of being exposed didn't stop me from rolling over onto my front and slowly grinding on the bed as I stared out the window and eagerly awaited his response.

"I'm on my balcony again tonight, my wife is gone to sleep and I want another show while I enjoy my glass of wine" the typing icon flashed up again "are you going to be a good girl?"

That flipped the switch, in almost a daze I flicked off the interior lights and padded out to the balcony. My phone beeped asking me where my stockings and heels had gone and I quickly turned back to get them.

I brought them to the end of the bed and made a show of pulling the white hold up stockings up my legs hoping that he could see in. I buckled the gold strappy heels around my ankles and clicked out onto the balcony.

"Walk to the edge, hands on the railing". I stood there looking out now feeling entirely exposed. Not the discreet position I thought I was in last night, the glass balustrade hiding nothing as the wind whipped up the bottom of my satin babydoll exposing the lace detail at the top of my stockings and goosebumps formed on my bare ass.

It felt like an age before my phone beeped from the coffee table. I stepped back to read "on the coffee table, on all fours. I was imagining fucking you on it while you pretended to be so demure in the sauna. I might not be able to resist coming over and doing just that..."

And just like that my heart started racing again. I knelt on the coffee table, heels dangling from the edge, the wind now whipping the babydoll up and over my back putting my bare ass on display for anyone who chose to look. Each time I smoothed it back down a fresh gust lifted the satin up until I decided to leave my smooth ass displayed for him.

I closed my eyes and imagined that handsome stranger from the sauna sitting on his balcony stroking his cock to me while he held his glass of wine with the other. I was just imagining him exploding all over his stomach while his wife slept inside when I heard a knock on my door...

My phone beeped with a message , "open it".