How Gerry Caught Me Crossdressing!

When we're young, we can be extremely naïve! This applies to almost everyone, and it's my only excuse as to how Gerry caught me crossdressing so easily. I had paid for a room in the hostel where he worked as a caretaker, and expected privacy. It simply never occurred to me that he, or anyone else for that matter, would feel at liberty to intrude upon me on the slightest whim...

But he did! A retired marine in his early forties, Gerry's predatory nature forced him to take an interest in every guy under 25 who checked in -- and naturally, as part of his job, he had a skeleton key to all the rooms.

I was lying on my bed, dressed in a satin blouse and black tights while reading the Evening Standard, when he let himself in. "What the fuck do you want?!" I demanded, sitting up with a dreadful start. I was edgy and confused, but Gerry stayed unnervingly cool.

"You'll find out what I want soon enough, sweetheart!" he chuckled knowingly, securing my door by bolting the latch...

As far as Gerry was concerned, my fate had been sealed a couple of days earlier, when I'd first arrived. I'd travelled to London on a late evening train, anxious I was cutting it fine to be fit and alert for my new job the next morning.

In my hopes and prayers, I was leaving my home city once and forever. There, I was considered a sissy and a faggot -- a boy who couldn't help but act like a girl. Every effort had been made to toughen me up so I'd fit in, but nothing had worked. In fact, one particularly brutal assault had rendered me incapable of active sexual engagement...

And in my youthful naivety, I believed that the streets of London, if not exactly paved with gold, were sometimes trodden by folk willing to embrace a young, northern tranny with welcoming arms. In this, despite my tribulations, I still believe I was half right!

No sooner had I finished my breakfast and jumped on a bus for my first day at work, than Gerry must have let himself into my room. And how he must have smiled (between gulps on his service flask, filled with cheap whisky) when finding my lipstick and mascara, half-buried underneath more mundane toiletries.

His excitement can only have increased when he discovered my tights, stockings, knickers and bras, carelessly concealed beneath a few innocuous T-shirts in the chest of drawers, along with my nighties and lingerie.

And then to the wardrobe, where my dresses, skirts and blouses hung indiscreetly. Lastly, he'd have surely been thrilled to glance below those vestments, where my black court shoes, white knee-high boots and red stiletto sandals awaited his prying eyes.

"The problem," Gerry explained menacingly, "is that I'm obliged to report perverts to the proprietor." He sat down on the bed right next to me, and began fingering my crotch as I searched hopelessly for an appropriate response. "Part of my job," he continued, "is to prevent a scandal. And we don't want a scandal now -- do we?"

He was eyeballing me harshly -- staring at me with an unnerving intensity, whilst at the very same time he was lightly stroking my tights, right above my cock. I felt helplessly mesmerised. "No," I replied tremulously. "We don't want a scandal!"

Lying there dumbstruck, I began responding to his unspoken commands like an automaton. Somehow, he'd managed to gain hypnotic powers over me, and I soon found myself doing whatever he demanded. So at his prompting, I thoughtlessly rolled my tights onto my thighs and tugged my panties down.

Then I turned obediently onto my belly, stretching my legs as far apart as I could whilst elevating my bum with my knees, until I was just where he wanted me, and he told me to hold my poise.

"I see you've been posted?" Gerry observed, feeling how the red end of my penis is stone cold, while my sac can all but boil tea! "A waste, really! Still," he remarked nonchalantly, "they do that to sissies everywhere!"

I flushed with anger! Some years earlier, vicious thugs had repeatedly flung me, groin first, into a metal banister -- leaving me able to ejaculate, yet incapable of getting an erection or experiencing a proper orgasm. And who was this violator to make a joke of it? And yet somehow I refrained from an outburst, remaining instead locked under his mesmeric spell...

Gerry unbuckled his belt, letting his jeans drop around his ankles. Spotting my moisturiser on top of the dresser, he squirted a generous measure onto his hands, then slopped it carelessly around his throbbing cock. "Just remember," he chided, approaching me from behind as I squirmed silently in terror, "we need to keep this nice and quiet - so as to avoid a scandal!"

Suddenly, I felt claustrophobically overwhelmed, as Gerry grabbed my mouth, hermetically sealing my lips together with such force that trying to scream was beyond impossible, whilst simultaneously he pressed his cock inside me with such power I believed myself mortally wounded.

Both the tightness of my butt crack and the tears that burst across my face must have told him instantly he'd just robbed me of my virginity -- but he didn't care an iota...

He was sublimely mechanical in his approach, being utterly determined not only to maximize the pain and humiliation he knew he was inflicting, but to make sure I would never forget those feelings -- and I never have!

His long, slow, forceful rhythm naturally caused my legs to alternately stiffen and flail, in spite of my discomfort, so that, after a few minutes, a fly on the wall might have come to believe I was enjoying myself. This was very much a part of his plan, and he responded to my purely reflexive spasms by whispering sweet nothings in my ear, hoping to increase my degradation even further.

Throughout this baptism of fire, all I could smell was stale tobacco off his hand and rum off his breath, while all I could feel was my bum glowing, as though Gerry's relentlessly throbbing penis was a stray ember that had somehow managed to get in the wrong place, starting an inferno ...

Which metaphorically of course, it had! Because by the time I felt his warm cum exploding into the deeper recesses of my burning anus, a significant change had subtly overtaken me. Possibly to make my ordeal less unbearable, at some point I'd begun to swing my hips ever so slightly, keeping in rhythm with the pulsing thrusts of Gerry's rock-solid manhood.

Slowly but surely, I'd increased these gyrations, until without even realizing what I was doing, I'd begun to join in - to collaborate with my own brutal violation! So when Gerry finally withdrew his deflating penis from within me and began wiping himself clean on my bedclothes, a conspiratorial smile was forming upon his haggard face...

He'd turned me -- and he knew it!

I was surprised how soundly I slept that night. Unusually, there was no sign of Gerry in the breakfast room next morning but, when I returned from work, I was delighted to find an exquisite pencil skirt laid out neatly across my bed.

That night, when Gerry paid me a visit, he found me waiting for him in suspender stockings and a pink negligee! I gave myself to him quite willingly; squatting beneath him so I could meet his magnetic stare as he ploughed between my butt cheeks with his well-honed cock. And for all the pain he inflicted, I was able to muster the will to return his smile. What a turnaround I'd achieved - my rapist was now my lover!

For the next couple of months, I lived for Gerry's nocturnal visits. Those, and all his presents! It was a rare exception when I did not return from work to find a gift of some sort; a skirt, blouse or dress - or else some make up, or even a pair of expensive tights. There was nearly always some new present waiting for me on my bed, and I frequently found myself praying that my bus home from work could magically sprout wings...

The hostel that had quickly become such a happy home to me was located in quite a derelict part of London; an area which, back in those days when miles of the city were fenced off with grey corrugated iron, they used to call a development area - it's since been knocked down to make way for a supermarket car park!

The guests were an eclectic bunch - mostly students, back-packers and youngsters from the provinces, seeking asylum from Mrs Thatcher's burgeoning northern dole queues. It belonged to a doddery old eccentric who feigned a belief he was doing God's work -- yet never failed to collect the rent on time! There were frequent disputes over whose was what in the laundry room...

Returning from work one evening, my mind focused happily on the surprise I fully expected to find lying on my bed, I was shocked to be intercepted in the reception hall by the proprietor. Sombrely, he asked me to follow him through to his office, where he sat himself down behind an old Victorian oak desk.

"I won't waste any time," he proclaimed grimly. "There's been a series of thefts -- and you're implicated!"

I must have threatened to faint because, to his great surprise, my landlord quickly found himself helping me into an easy chair. "I promise you," I gasped, furiously sipping at a glass of water he poured for me, "I've never stolen anything in my life!"

"That's easily said," he replied sombrely. "But the fact remains that all the missing items have been found in your room! They were stolen from several lady guests - and Gerry has been ordered off the premises!"

"I see!" I blurted. Tears welled up in my eyes, clouding my vision, as I realized my comfy idyll was crumbling around me. So Gerry had used his skeleton key to thieve all my little daily presents from rooms occupied by women - and now I was implicated as his accomplice! "What do you plan to do with me?" I stammered timidly.

A man in his early seventies whose suits had been purchased during the war, the proprietor carried a sad and lonely air around quite brilliantly. "I would rather not involve the police," he told me matter-of-factly, "but there's a need for recompense - do you understand? I will pay to replace all those clothes Gerry stole and gave to you -- but I must have something in return!"

Wearily nodding my compliance, I helped him pull his trousers down before taking off my own. As usual, I was wearing tights and panties under my work clothes, and the proprietor grunted ironically at this stark visual confirmation of the source of this latest fracas!

I knelt down before this lurid old man, pushing my face towards the seat of his tired and stale Victorian upholstery, and began tonguing his pimply balls. In remarkably little time, his cock showed encouraging signs of life, and I was soon able to pop it into my mouth and begin blowing and sucking until I felt his cum showering hastily against the back of my throat.

"That was most agreeable, my dear!" he said, looking genuinely satisfied that he'd got the better half of a bargain. Taking advantage of his momentary pleasure, I pleaded to be allowed to stay, but he was steadfastly set against me. "I'm afraid not!" he lamented. "You see, all the ladies know what's happened -- so if you don't leave right now, then they'll insist I call the police!"

Leave right now? I recoiled in abject horror and disgust! I'd just given that dirty old bastard a superb blowjob, and he wouldn't even let me stay one more night? Instead, he was kicking me onto the streets! Numb with fury, I stormed out of his office and up the staircase towards my room -- oblivious to the gawks and shouts of those guests I was passing. In my vexation, I'd forgotten to put my trousers back on, and was prancing around in tights and panties!

Upon my bed, I found one final gift from Gerry -- a hastily scrawled note with a telephone number on it. Still oblivious to my state of dress, I marched over to the payphone on the landing, and rang him straight away. He was in a pub two blocks away, drunk and desolate. He was also quite emotional. "I'm counting on you, Caz!" he repeated endlessly. "If you won't do this for me, then I'm completely fucked!"

I ran his proposition through my head several times, aware that I had no more spare change to feed into the phone if the pips went, and so a snap decision was called for. "I'll do it!" I decided just in time. "Pick me up at half past six..."

The evening meal was served between six o'clock and seven, and as the dining room was immediately below the reception hall, the area became extremely crowded. If I'd wished to sneak out of the hostel anonymously, I couldn't have picked a worse time -- but what the hell! My fellow guests already detested me as a sissy and a faggot and now (wrongly!) as a clothes thief - so why shouldn't I go out with a bang?

After showering, I moisturised every last inch of my body, and then put on my favourite silk panties and matching bra. Black, seamed hold-up stockings contrasted neatly with a little white dress I'd bought after seeing some mod girls wearing something similar along the King's Road. My white, knee-high boots completed an outfit that leant itself to my penchant for pale lipstick with lashings of mascara...

All my booty -- those clothes that Gerry had stolen without my knowledge, and which constituted more than half my entire wardrobe -- I shamelessly decided to keep! Why? Because I had paid for them in kind, by sucking on the proprietor's unwashed cock and swallowing his cum!

But that meant there wasn't room for everything in my suitcase! So I made a simple decision; I opted to leave all my male clothes behind! It meant I was leaving my job, so if Gerry's plan didn't work out, then I was utterly ruined. But why shouldn't Gerry's plan work out? Sometimes, we all need to have a little confidence in those we choose to love...

As I've already mentioned, the reception hall always buzzed with activity after six. It was the busiest time of the day, and you would frequently struggle to hear yourself think there. But as I descended the staircase from the rooms for the very last time, my suitcase in one hand and my treasured Dior handbag in the other, I recall that you could have heard a pin drop...

A sea of open jaws seemed to part before me, with only the proprietor giving me any acknowledgement, in the form of a knowing wink, as I walked through the crowd towards the front door, shrouded in a dignity I prayed wouldn't prove deceptively temporary. Outside, to my great relief, I spotted Gerry's car with the headlights on and the engine running.

As a stray raindrop dashed lightly against my powdered cheek, I nervously realized that a brand new chapter in my life was rapidly getting underway. The consequences of decisions that had been taken in great haste began to ring terrible warning bells and I shuddered violently, wishing I could simply turn back.

But a brief glance over my shoulder towards that crowded reception hall reminded me that no such option existed! I was entirely at Gerry's mercy now, and must accept the consequences. And so with much trepidation, I placed a delicate white heel over the threshold, taking my first step towards an entirely different way of life...