I was happy in my riverside apartment. It wasn’t spacious but, on a nice day, the views were to die for. It was quiet, especially considering the high street was just around the corner. So while there was plenty of bustle just a stone’s throw away, home was a haven of tranquility.
Truly, an idyll..
And then disaster struck! My boyfriend and I both worked at the same club and, without any warning, it closed down. We both lost our jobs but, whilst the boss offered him a job in another town, I was left in the lurch.
And he took the job..
Truth is, we hadn’t been getting on too well, and he grasped the opportunity of what is sometimes called a clean break. So I lost my job on Saturday night and my partner on Monday morning. And when he walked out of the door, he left behind more than just heartache – my rent doubled.
Of a sudden, I was in big trouble..
I looked everywhere for a job, but there was nothing doing. It was hard for everyone, and it’s always harder when you’re trans; you’re at the bottom of the pile. I was willing to do anything, but it did me no good.
The bills soon piled up..
And then the bank bounced my rent payment. I knew what would happen next; Ronald would come round. He wasn’t my landlord, but the landlord’s agent. When we signed the lease he’d told me, “Don’t ever miss a payment, cos if you do I’ll have to come round, and if I do you REALLY WON’T LIKE IT!”
The rent bounced on a Thursday afternoon, and Ronald showed up on Friday morning..
The knock at the door was so menacingly loud, I knew exactly who it was, even though he’d never called before. The only surprise was the early hour. It was barely nine, and I’d planned to be out already.
That morning, there were interviews for cleaning jobs in a nearby town, and I’d planned to go along. As such I was smartly turned out in a tartan skirt suit, with opaque black tights and matching stiletto courts. My hair was tied in a bun and my makeup was suitably toned down.
I really needed that job!
But there was no escaping Ronald. My apartment only had one door and he was hammering on it relentlessly, his knocks getting ever more furious.
Quaking in my heels, I stood at the kitchen table gasping for breath as I tried to summon the courage needed to face him.
“I know you’re in there!” he shouted, sounding really angry. “Whatever you do, don’t force me to break down the door!”
“D-don’t do that!” I stammered, “I’m c-coming!”
Somehow, I gathered the strength to open the door, and soon found myself face to face with a short, stocky, aggressive little man of about 50. He was all but bald, with just a few clusters of grey hair scattered wildly across his oily pate.
“Miss Quigley, I presume?” he asked, stepping into my apartment like he owned it, which I guess he kind of did.
“Y-yes!”
“I have to ask,” he continued, his beady eyes boring into me like drills, “Do you have the rent?”
“N-no!”
“That’s too bad!” he sighed, “Very bad indeed! So do you intend to pack your belongings here and now and vacate the premises forthwith?” he continued.
“N-no!” I wailed, “B-because I’ve nowhere else to go!”
“And is that MY problem?” he asked. “No, it is not!” he replied, answering his own question before turning his gaze on me again, “YOU are my problem, as you wish to continue living here without paying the rent! Isn’t it so, Miss Quigley?”
“I’m l-looking for a job,” I pleaded. “In fact, I was going for an interview just now..”
He stroked his chin thoughtfully..
“I see!” he mused. “And do you have a realistic prospect of getting this job?”
“Y-yes!” I lied. I’d have said anything just then that helped him go away.
“Very well,” he decided after a little more musing, “I’ll tell you what I’ll do – I’ll pretend you were out and come back on Monday. And as long as you get the job, we’ll be okay, won’t we?”
“Oh, y-yes!” I exclaimed. “Th-thank you!”
“Of course,” he continued, “This is a very big favour I’m doing you – I could lose my job over it. So how about doing something in return, huh?”
Saying which, he winked whilst nodding towards his midriff. I understood him all too well, and dropped to my knees before his crotch. Smiling, he lowered his trousers and took down his boxers, revealing a short, thick cock with a bulbous cherry glistening with precum.
It made me wonder just how long he’d spent anticipating this favour!
I ran my tongue slowly up the stiff stem of his throbbing manhood then carefully licked the salty precum, teasing his cherry in the hope he’d fire his load early.
But he did nothing of the kind..
Placing both hands in my hair, he forced my face deep into his crotch till the whole of his quivering meat-rod was within my mouth, whilst my trembling lips were tickled by straggly pubic hairs.
Satisfied he had me just where he wanted me, he held me fast, moving my head just a little back and forth until, groaning with pleasure, he fired off a staccato stream of warm, salty cream into the back of my throat
At last he withdrew, leaving me crumpled on the carpet, gasping for breath.
“I hope you get the job,” he told me, cheerfully zipping his fly, “but if you don’t, then you’d best clear out over the weekend! Cos if you’re here on Monday and you still can’t pay, you’ll get a spanking!”
I hadn’t a clue what he meant, and he left without bothering to clarify. Needless to say, I didn’t get the job. Thanks to Ronald I was late for the interview and my hair was in a dreadful mess.
That weekend, I got so desperate I even spent money I didn’t have going up to London to register with a couple of escort agencies. In the end, that turned out to be a good move, cos I finished up working as an escort for years, but it didn’t help me with Ronald.
But come Monday morning, I thought I had a cunning plan..
I arose bright and early, and put on a frilly red blouse with a black pencil skirt. Underneath, I wore a black thong, faux leather peekaboo bra and a faux leather suspender belt with six straps.
My stockings were black with red seams, and I wore my highest heels, a pair of red, four-inch peep toe sandals.
I painted all my nails crimson, and applied a matching lip gloss, lashings of mascara and plenty of eyeliner. As for my hair, on Sunday evening I dyed it platinum blonde.
I intended to give Ronald every good reason to cut me some slack!
Just before nine, there was a familiar, menacing knock..
I sauntered down the hallway and opened the door with my sweetest smile.
“Wow, you look very nice!” Ronald whistled. “It’s almost a shame, what I have to do next!”
“W-what do you have to do?” I stammered, scared by the evil glint in his eyes.
“Have you got the money, Miss Quigley?”
“N-no!”
“Then I’m afraid it’s a spanking!”
Closing the door carefully, he removed from his raincoat pocket a riding crop.
“Shall we do it in the bedroom?” he asked, casually hanging his coat behind the door.
“N-no!” I cried again, “You d-don’t understand – I’m willing to do anything!”
He sighed and shook his head..
“And so you shall, Miss Quigley! But I am a man of my word, and I promised you a spanking if you were still here today and couldn’t pay the rent. And a spanking is just what you’re going to get!”
I began to cry, though it cut no ice with Ronald. He pushed me into the bedroom weeping, and bent me over an easy chair before pulling off my pencil skirt, exposing my bum, which was naked but for the suspender straps and a sliver of thong over my boy-pussy.
“Very nice!” he enthused, swishing his riding crop through the air. My legs were trembling in anticipation, and I wished I hadn’t worn my highest stilettos, which I was struggling to keep on the ground.
Out of the blue, a loud swish was followed by the crack of leather upon tender flesh, and I jumped convulsively, screaming in sudden pain as the sharp twang burned my fleshy orbs.
“Oh, please!” I cried, “No more!”
“Don’t be silly, Miss Quigley!” Ronald replied, sounding mildly amused. “I’ve only just started!”
Another blow struck, then another and another. My bum felt as if it were on fire, and I cried so much a stream of mascara ran down my cheeks. In vain, I struggled to break free.
But it was no use; Ronald held me fast. His firm grip on the back of my neck left me no leeway, and I was utterly at his mercy.
“You’re only making it worse,” he told me nonchalantly. “Accept your punishment, and it will soon be over!”
There being no other choice, I reluctantly took his advice. He struck five more blows, each with a terrible sting that brought fresh tears to my eyes. But I stifled my screams and tried to sob as quietly as I could, much to Ronald’s satisfaction.
“Good girl!” he exclaimed, tossing the riding crop aside. “That’ll do for punishment, now you just need to pay some rent in kind!”
He led me over to the bed where I lay down on my belly, my bum being far too sore to even think of sitting on.
And there I stayed, sobbing silently but offering no resistance as he did what he pleased with me. First, he spread my legs wide apart, then tugged my thong down onto my thighs. He undressed himself below the waist, then clambered onto the bed on top of me.
I felt his stale breath upon the back of my neck, while at the same time exploratory fingers began easing their way beneath my bra cups.
Without warning, he lifted my upper half off the bed and began furiously fondling my breasts, at the same time kissing my neck.
And then, I felt him enter me..
His well-oiled cock slid effortlessly between my butt cheeks into my boy-pussy, and began to pump in and out relentlessly. It was thick and hard as rock, and whatever was lacking in length was more than compensated by girth, so that I soon felt my rim stretching to breaking point as the thick, steely ramrod thrust in and out, hard and fast, like a machine.
My legs wanted to flail but could not, for he’d pinioned them against his stocky chest, there to act as fulcrums as he pounded my boy-pussy so hard it began to throb even more than my poor, thrashed buttocks.
I thought for a while it was never going to end, but then at last felt the first warm spurt of cum splosh into my inner depths.
Further spurts followed in rapid succession, and Ronald groaned loudly with pleasure. At long last, his grip on my breasts slackened and he climbed off me, at the same time withdrawing his semi-flaccid cock.
Through agony and exhaustion, I didn’t stir from the bed, but buried my shame in a pillow while Ronald happily dressed himself.
“That was rather nice,” he told me airily, “I’ve never done a tranny before.”
“Perhaps most of us are better than me at paying the rent?!” I suggested icily.
“That just bought you a week’s grace,” he explained nonchalantly, pulling up his trousers. “But if you can’t pay next week, make sure you’re gone before I get here, or the next spanking will be something else!”
I burst into tears, but told him I understood, and his tone softened. “If you really can’t find anything else,” he suggested, “you should try hooking it – you’re a natural!”
I smiled sardonically. “Way ahead of you!” I thought.