• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • The Constance Gardener

The Constance Gardener

This is a tale of a chance encounter along the long tow-path that trails below the garden gates found between Runnymede and Windsor. I guess, if you wanted, you could wander all the way from London to Reading on that path? Not my idea of fun though, as I'd waste an otherwise perfectly good pair of heels, but I reckon it's doable.

My friend Connie lived about halfway between the towns mentioned, in a tumbledown cottage she shared with her sister Emma and Jenna, who was Emma's best friend from university. This was back in those not-so-distant days when a group of young graduates could afford a house-share in such an area; nowadays, of course, it's very much millionaire's row!

Mind you, the cottage was no show-home; it needed far more than a mere lick of paint, if you know what I mean! Timbers were rotting and masonry crumbled, and then there was the garden - a gargantuan green acre of mostly grass, with a steep, high hedge running right around the boundary.

Now, Connie wasn't 'out' in those days, not even to her sister. She was Robert to the whole wide world, except on those days she got to have the house to herself which, because she worked different shifts to her two sharers, happened maybe once or twice a week.

On such days, the little cottage became a true tranny's Eden!

She kept a small but stylish second wardrobe in her room, but with the place to herself she was able to borrow generously from the girls without their knowledge. So once they were safely off to work, she'd slip into some nice lingerie before taking a leisurely look through the latest acquisitions hanging in the ladies' wardrobes.

On the day I'm talking about, she put on her own matching black bra and panties, along with seamed hold-up stockings, then raided Emma's room for a lovely, floral patterned red dress she'd been recently admiring. Next, she flitted into Jenna's boudoir, to take advantage of the generous clutter of make-up crowding her dresser.

Such a slut, that girl; no matter how much of her stuff Connie borrowed, she never noticed!

Once she'd finished helping herself to a nice, moisturising lippy that matched her nail varnish, it was time for Connie to return to her own room, where her fine blond wig and red platform heels finished off the stunning effect she was after. Staring at herself in a full-length mirror, she felt greatly cheered. The sun was in the sky, and it seemed a leisurely day of lounging around was stretching ahead!

And stretch was the right word! For after breakfasting in the conservatory, she chose to lay out a sun lounger on the lawn, mix a carafe of iced lemonade, and settle down with a racy novel. How great were those high hedges? None of the neighbours could see anything of this side of the garden, which was blocked off from the front of the house by a firmly padlocked gate.

Relaxed, alone and feeling amazingly complete, she soon allowed the sun's gentle rays to lull her into a nice, deep slumber from which, as she suddenly came round, she blamed a bumblebee for buzzing too near her face.

It took a few moments for Connie to realize there was in fact no bee. The buzzing that woke her up was coming from a lawnmower that was criss-crossing her lawn, making nice neat stripes, and passing barely feet beneath her heels!

Somehow, she'd managed to forget about Kevin!

If she'd been wearing lower heels, she might have kicked herself; for how stupid can one be? It had slipped her mind entirely that Kevin the gardener was due, and that he always parked in a nearby lane and accessed the garden via the tow-path gate, for which he had a key!

A surly northern type, he rarely spoke except on Saturdays at month's end, when he called with his bill. That's when either Robert, Emma or Jenna would settle his bill and tell him of any extras that wanted doing.

For sure, he was well acquainted with everyone who lived in the cottage!

I've said it was a large lawn? Well, it was! It had to take a couple of minutes to push the mower either way, so Connie figured she'd pretend she was still snoozing while Kevin came crossways towards her then, when he turned around, she'd sit up. And as he moved away from her, she'd slowly totter along the path, keeping out of his periphery, till he was close to reaching the other end, when she'd dive into the conservatory before he noticed what was what.

So with her heart ticking wildly, she began implementing this plan. As Kevin mowed with his back to her, she tottered timorously across the crazy paving, coming tantalizingly close to the conservatory before, with a sudden drowning noise, the mower came to a dead halt and, quick as a flash, Kevin turned around, revealing ruddy red cheeks below eyeballs melting with malice.

"Going somewhere, Robert?" he asked pointedly.

"I'm... err... inside!" Connie stammered, wishing the earth would simply swallow her.

"No you're not!" the unusually garrulous gardener insisted, pointing towards the sun lounger. "You get back to your beauty sleep till I'm done mowing, when we'll have a nice, cosy chat!"

Connie wasn't sure what to do, but figured she'd best obey him at least till she worked out a plan, so she did as he'd told her. The mower started again, and Kevin carried on his work while she feigned sleep but, believe you me, what followed was the longest twenty minutes of her life. So by the time he got round to wheeling his mower down towards the gate, like he always did when he was finished, and sauntering over towards her sun lounger, she was all but quaking in her heels, convinced as she was that he might be planning to murder her!

"Open your eyes!" Kevin commanded. "I know you're not asleep, cos you're shaking so much!"

Connie did as he said, and was hardly reassured by the look of pure scorn written on his rustic, ruddy face.

"Do the young ladies know you like to do this?" he asked.

"Err... n-no!"

"Mmm..."

Kevin saw this as a serious problem. He'd been in similar situations before, and knew what hypocrites people were. While caught like a rabbit in a headlamp, they'll say anything, but then they make up excuses and sack you. Yes that's right, for being a reliable gardener and turning up on time, you can get sacked just for seeing something you weren't meant to see! How's that for mean?

"Well, they'll know soon enough if you don't do exactly what I tell you, understand?"

"Y-yes!" Connie confirmed meekly.

"Good! Now come with me..."

Connie tottered nervously over the lawn towards a half-restored Victorian water feature; a small pond containing a statue of a mermaid who could no longer gurgle water, surrounded by a pergola brimming with honeysuckle that gladly concealed a recently creosoted garden bench.

"I've often thought of sneaking in here of a night with a bird!" Kevin confessed unexpectedly, "But I suppose this is the next best thing? Come on then, bend over!"

"I-I'm not..."

"None of that shit now; not unless you want to explain yourself to those fine ladies!"

Reluctantly Connie, who though she liked to dress was yet to make up her mind whether she preferred men or girls, and was a virgin in every sense, bent forward over the bench, her nostrils immediately gagging on the powerful smell of recently applied coal tar.

She staggered slightly as Kevin kicked her feet a little further apart, before lifting the hem of her sister's pretty red dress and pulling down her silky black knickers.

"Mmm, very nice!" Kevin crooned approvingly, stroking the back of her nylon-clad thighs while he applied a generous dollop of chainsaw grease to his burgeoning manhood. With firm hands pressing uncomfortably into her hips, he pulled Connie this way and that until his cherry was just where he wanted it, then entered her without the slightest finesse, squeezing his full seven inches as far as they'd go before beginning to pump away slowly like a steam piston.

And boy, could he pump! He clearly possessed a mechanical attitude to sex, and took pride in his staying power. Of course, poor virgin Connie was flaying hopelessly, while wasting salty tears that dripped onto the well-worn crazy paving to no known effect. Her mascara ran so badly, her face soon began to look like a Jackson Pollock painting, while her sobs carried forlornly across the tow-path, towards the perpetually uncaring Thames.

Pummelling away without meaningful resistance, Kevin let a hand stray toward Connie's tackle. He found it flaccid, which at first he found strange - for surely a fruitcake like this silly creature would enjoy such a manly seeing-to, he thought? And sure enough, a little massaging proved him right for, despite the ongoing tears and groans, he felt Connie grow then cum in his hand before he deigned to empty his own, much more substantial load into the deep end of her tight back passage.

"Enjoy that, Sissy?" It seemed an ironic question, given the mess Connie's face had become with all those tears mixed with so much make-up, but still Kevin enjoyed asking it. Because he wasn't finished yet!

"Okay Sissy; time for you to get on your knees and clean me up!"

"I-I can't!"

"Well, that's a shame! Guess I'll have to stay right here with you just like this till the ladies get back..."

Sobbing and sore, Connie got down on her knees. She realized the little red dress was ruined, not least because her own cum was dripping down the inside of the skirt, and that she'd have some heavy explaining to do come what may. But dare she disobey this brash, working-class bully?

Of course not!

Trying her best to ignore the smell of his bitter sweat and the stains on his jeans from soil and grass and God knows what kinds of compost, she allowed Kevin to place his slightly flaccid meat-rod in her mouth, and while he held her head firmly where he wanted it, she gagged away while licking clean and slowly swallowing a bitter mixture of his salty cream, her own waste and rather a lot of chainsaw grease.

It seemed like forever, though probably it was only around ten minutes before he declared himself satisfied. Afterwards, he wrote her an invoice for the whole of the season and insisted on being paid right there and then, in return for which he vowed never to return; a vow Connie prayed hard he'd keep!

As soon as Kevin left, Connie had the longest bath she'd ever had in her life and then, dressed as Robert, drove to Windsor and bought a replacement dress for Emma. But it wasn't quite the same and it started a discussion which eventually forced Connie into making a full and frank confession to both her house-mates.

Naturally, they were outraged and wanted her to call the police but, back in those not quite so enlightened days, she wasn't comfortable with the idea, and so Kevin got a free notch on his belt if you like, though it wasn't all bad for Connie.

In fact, she slept well that night. For not only was it nice to be 'out' but she'd finally found out for sure who she liked sleeping with...

Men, most definitely!

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • The Constance Gardener

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 220 milliseconds