Caretaker Joe

It was my first time living on my own. I was 18, and enrolled at a college to study art and photography, in a town far from home, in fact close to London.

I took a room in a hostel, popular with students. It was halfway down an ill-lit corridor, and no one seemed to bother me, which suited me just fine; I liked the solitude. I was confused about my gender identity, and wished to do some self-discovery.

Before leaving home, my parents had given me some dough to buy clothes, which I'd done, though my purchases were hardly what they'd had in mind!

I'd bought skirts and tops, panties and tights, a couple of bras and a cheap blonde wig. At the same time, my sister's make-up bag had mysteriously gone astray! The only thing I hadn't sorted to my satisfaction was shoes, so I was making do with a pair of pretty brown boots, which though girlie, were sold as unisex.

Where I'd gone wrong was to assume nobody ever went in my room. Truth was, the caretaker had a master key, and routinely checked all the rooms. He was a nosey parker called Joe; a dark-haired, weather-beaten ex-policeman in his forties, who thought it his business to search every room thoroughly.

Within hours of first unpacking then going out, he must have known my secret, though at first he didn't let on. But he started greeting me when we passed in the corridors, which made me think he was a friendly guy.

Halfway through my second week, there was an unexpected knock at the door. It was ten at night. I had on a pretty, dog-tooth miniskirt, a turtleneck purple top, black tights, my wig and plenty of make-up. The last thing I wanted to do was answer the door!

"Who is it?" I whispered, no louder than was necessary.

"It's Joe the caretaker; let me in!"

"Now's not a good time, Joe!" I said.

He didn't reply, instead I heard a key in the lock, and before I could think to snick the latch, the door swung open and I found myself face to face with him!

Though feeling vulnerable, I was also outraged. "How dare you!" I protested, "Get out of my room at once!"

But Joe just smiled...

"Calm down, dear!" he replied, "I'm not going to hurt you; to the contrary, we're going to have a fun time! That is, unless you really want me to leave, in which case I'll go down to the office, where your details are on file, and contact your parents! How does that sound?"

It sounded awful! My father was a strict disciplinarian who hated 'queers' and had long harboured dark suspicions about me. Had Joe carried out his threat, my life wouldn't have been worth living! My pulse shot up and I no doubt reddened, giving Joe his answer.

"Of course," he continued, "I don't want to do that, I'd rather we were friends! Wouldn't you like that?"

"I g-guess so," I stuttered. I was a virgin in every sense, never having so much as kissed a boy, or for that matter a girl.

"That's good!" he said. "Now go and lie down on the bed."

Uneasily, I did as he asked, and he wasted no time in putting a hand under my skirt and massaging my boy-bits. Although I found him scary and repulsive, he managed to trap my tiny rod between his thumb and forefinger, rubbing it through the nylon of my tights in much the same way I used to jerk off back then. Within seconds I exploded, soaking my panties and his fingers in hot cream.

"There!" he said, "That wasn't so bad, was it? Now for my turn!"

He stood up and dropped his trousers, revealing a stiff ramrod that dwarfed my pathetic endowment, being at least seven inches long and two inches thick. On the tip of his cherry, a generous drop of pre-cum glistened beneath the unshaded overhead lightbulb.

"You need to kneel down here," he said, pointing at the floor by his feet. I did as he said, acutely conscious of a damp squelch in my panties and the smell of my own cum. Up close, his cock looked forbiddingly large and I hesitated from taking it in my mouth...

At least, I tried to! Before I had a chance even to catch my breath, I felt Joe's powerful hands on the back of my head. He pushed me onto him, forcing his manhood far down my throat till I began to gag and choke.

"Don't worry, sissy!" he whispered, in tones that were surprisingly sympathetic. "I promise you won't suffocate, and it gets easier every time!"

As I quickly learnt to breathe through my nose and ignore my gag reflex, Joe forced his way ever deeper, till I could feel drops of his hot pre-cum trickling down the back of my throat and expected him to offload any second.

But he didn't...

Instead, he pulled out. "Okay," he said, "Now let's take a look at that cute little behind of yours! Get back on the bed, hitch up that skirt and pull down those soaking wet panties!"

I did as he asked, though I was trembling so much the bed rattled! Squatting on all fours with Joe out of sight behind me, soon I felt a dab of cold lubricant being rubbed around my rim, then of a sudden, Joe's manhood was inside me, pounding up and down like a piston on steroids.

That's when I discovered I'm a noisy lover! I groan a lot whilst taking cock; grunt and whine, because it feels so good, so natural. Even though Joe had taken advantage of me, I really enjoyed his fucking me, cos it was the first time I'd ever felt like a woman, which is what I'd always yearned to be.

An old hand at the exploitation business (I stayed in that hostel for two years, during which he took advantage of at least a dozen students, girls AND boys!) Joe took his time before filling me with his hot cum; but long before he was done, I knew I'd welcome him back to my room, any time he cared to come calling.

And did he take advantage of my generosity? You bet!