The Ungay Gordon

"You must understand," Gordon said casually, "That I'm not gay. Still, I want you to masturbate for me." It was a funny thing to say, and caught me entirely off guard. At 43, Gordon was a couple of years older than my mother. He'd told me he was married, and had earlier chatted amicably to my girlfriend.

Yet here he was, asking me to masturbate!

In all truth, I wasn't entirely surprised. Though we'd gone to the pub as friends, the chemistry was anything but equal. Walking there, he'd touched my ass several times, always with some lame excuse. Then over a couple of jars, his conversation had returned time and again to what it must feel like to be fucked.

Most particularly, how would I feel about it?

We were both staying in a cheap hostel, along with Mary, my supposed girlfriend, of whom more later. Gordon was a builder, recently returned from Australia and looking for work. I was a shop assistant with a murky past.

A few months earlier, I'd been forced to leave my home town under a dark cloud. It was 1985, not the best of times to be trans, and my life had gone pear-shaped after some boys from my college caught me in the local mall, dressed as a girl.

They'd roughed me up a bit, but I'd been spared the beating I'd dreaded on the orders of their leader. But there'd been a price to pay for this unexpected act of leniency -- I was to make myself discreetly available to him, whenever and wherever he chose.

Naturally, I agreed, the alternative to his cock in my mouth being his fist. To begin with, we met in a derelict house on the outskirts of town, a place I often used as a changing facility.

I would always get there first and dress, so he'd only see me as a girl. A laconic hunk, he'd make me kneel down and suck him off, and if he bothered to say anything at all while I had my mouth full, it was always the same mantra, which he repeated like a broken record.

"I'm not gay," he'd say, "I'm only using you for practice."

He had an older sister, and sometimes brought me her cast-offs to wear. One time, he gave me her old school uniform. He wanted me to wear it because he was going out with a girl from the same school and wanted to pretend she was sucking him off.

This floated his boat so nicely that from then on I always wore that uniform, and he began to treat me a whole lot better. I was given some really nice stuff, not just clothes but scent and make-up as well. It was all most likely shoplifted, but it's the thought that counts, right?

Alas, this cosier relationship brought its troubles. He became a lot more demanding, and started to insist I should meet him in the college toilets during lunch breaks. This was more than a bit risky, as it meant I'd have to carry a change of clothes around in my bag all day.

"But what if I get searched?" I asked him anxiously.

"You'll think of something," he shrugged, and that was the end of the matter.

The toilets at our college were in a grim, grey block at the far end of the grounds, some distance from the main building. It was a well-known trouble spot, frequented by the kind of students that nerds and sissies such as myself would normally go out of their way to avoid. Inside, the air was a fug of tobacco, bleach and urine. The toilet bowls were cracked and decrepit, and the cisterns all seemed to leak copiously onto the cold, concrete floor.

The cubicle in which we were to meet was right at the back, as far from the entrance as you could get. It was dark, gloomy and very poorly ventilated. The first time I went there, a gang was hanging around smoking. They looked at me wide-eyed, astonished I had the nerve to go anywhere near them, and itching to make me sorry I'd bothered. But when they saw which cubicle I was going into, they left me well alone. They knew what was happening and didn't want the aggro.

Once inside the cubicle, I'd nervously change into my girl's uniform, with bra and panties underneath. I'd wait in lonely silence, hardly daring to breathe whilst muffled footsteps and conversations echoed everywhere.

By the time my guy turned up, I'd be sat awkwardly on the toilet seat, a shivering bag of nerves. With shaking fingers I'd unfasten the catch to let him in, and he'd silently drop his trousers whilst I knelt down on the cold, urine spattered floor, ready to take his cock.

He'd place a firm hand on either side of my head and guide my lips up and down the length of his stiff, pulsating pole. His grip felt surprisingly gentle, yet I could also feel an underlying power that made me tremble to think what might happen should we ever fall out.

To minimise the possibility I left everything, quite literally, in his hands. He did with me just whatever he pleased, thrusting his meat in and out past my lips and teasing the back of my throat till, of a sudden, my mouth would fill with cum, which I quietly swallowed. The whole business never lasted more than a few minutes, and then he'd be on his way, leaving me to change back into my regular clothes and return to my lessons with a salty residue in the back of my throat.

This became a daily routine, except on Thursdays when he had football practice. Then at weekends we met in the derelict house, where I was expected to pay much closer attention to my appearance. I'd put on make-up, and wear nylons and heels. My life began to revolve around him. I came to think of him not as a bully but a boyfriend, and to enjoy giving him pleasure.

And then, at just past one on an otherwise uneventful Tuesday lunchtime, my cosy little existence came to a sudden end. We were caught! A pair of overly eager janitors staked out our cubicle, then crashed the door open to find me on my knees, sucking his cock.

They strong-armed us to the principal's office, a walk of shame that took us across the college grounds then right along the central corridor, passing multiple clusters of astonished students as we went. Dressed as I was and with cum dripping from my lips, I quickly became the centre of unwanted attention.

Not for long, though. The principal needed no more than a quick glance to expel me. To my bully, he was somewhat more lenient. He received a week's suspension and a month of litter-picking duties. But he was a popular lad, needed by the football team. And besides, as the principal said, at least he'd been acting like a man.

Naturally, the college did its best to hush the matter up, but too many students had seen too much, and word spread through the town like wildfire. My life became unbearable and so I fled to the big city, where nobody knew anything about me, and tried to turn over a new leaf by pretending to be somebody altogether different.

Except Gordon had read me like an open book!

Actually, he wasn't the only one. I'd gone to bed with Mary, a sweet girl I really liked, hoping that if I could manage to perform as a man just once then maybe it would get easier after that, and I'd be able to change. But I'd stayed stubbornly flaccid despite her best efforts, and she wasn't exactly impressed.

Indeed, she'd been brought to tears, and it had been her suggestion that I should go out with Gordon the following night.

"It'll give us both some time to think," she'd said.

And now here I was, in Gordon's room ostensibly for a sobering coffee, but being asked instead to masturbate!

Partly because of what had happened with Mary, but mostly because a little beer soon loosens my tongue, I decided to be brutally honest..

"I'm a tranny," I told him, "I've never been fucked, but I have been with a man. I'll do as you ask, but I'll need to wear women's clothes."

"Alright," he said. His eyes widened considerably, and I could see he was really interested.

"And you have to treat me like a girl," I added.

"Goes without saying!" he replied excitedly.

We agreed he'd give me time to change, then meet me in my room five minutes later. I hurried off and, quaking with nerves, pulled an old grey shoulder bag out from the bottom of my suitcase.

Before the scandal at college, I'd had quite an extensive wardrobe, but in the aftermath, my mum had chucked most of it out. "It's for your own good," she said, "You've really got to try and change this time!"

She was fed up because it wasn't the first time I'd been in trouble of that kind. She'd been catching me trying on her stuff for years, whilst the nice girl next door used to dress me up in her clothes, at least until my mum spoke to her mum and they knocked it on the head.

Of course, I'd been much younger then, and Mum had hoped it was just a phase I'd eventually outgrow. But even before the college scandal, my auntie had sworn blind she'd seen a girl who looked my very double waltzing down the high street in one of her old dresses, whilst a nosy neighbour insisted she'd seen me go into the derelict house on the corner and come out as a girl. And there was more besides, so much more it did her head in.

So she gave most of my wardrobe to a charity shop! Still, there'd been stuff she hadn't found and which I'd clung onto, just in case the transformation she was praying for didn't come to pass. Among these remnants were a pink, satin bra with matching panties and a pair of black tights, all of which I was now putting on, and none too quickly, for I was soon interrupted by a loud, impatient knocking at the door.

I almost jumped out of my skin. The knocks seemed to echo everywhere, and brought back memories of that awful moment when those dirty-minded janitors crashed into the toilet cubicle and turned my life upside-down.

Honestly, I thought them so loud I really expected all the doors in the corridor to open, and people to come out and gape at me, just like the students had done that terrible day.

"You didn't give me five minutes," I grumbled, hastily beckoning Gordon to enter, "I wasn't quite ready."

"You look just fine," he replied. "Now how's about doing what I asked?"

"Okay," I said and lay down. The room was tiny, with just enough space for a narrow single bed, a dressing-table and wardrobe. Gordon perched beside me on the bed, smiling intensely as his hand strayed casually onto my nylon-clad crotch.

Unlike the bully whose attentions had led to my downfall, there was nothing overtly frightening about Gordon. He was ruggedly handsome, with dark hair and swarthy, suntanned skin. I was strangely calm in his presence. Despite his near constant smile, his deep, brown eyes betrayed a forceful personality and an eagerness to dominate, even to belittle me. I couldn't meet his stare for long without trembling, so quickly turned away.

Silently, his fingers began to explore my crotch. Keeping on the outside of the gusset, he plucked my cock carefully from between my thighs and stretched it out along my belly, then stroked it, slowly at first but upping the tempo with each and every stroke until the tension of his fingers tingling against taut nylon caused my legs to spasm and froth to fill the gusset from my fast spewing cherry.

It was all so overwhelming that I burst into tears.

"Why are you crying?" Gordon chuckled.

"Because," I sobbed, "I'm not sure what I am!"

"Oh, I think you know!" he replied, "But just in case, I'll tell you. You're a transsexual, which makes you prime bait for alpha males like me. And do you know why?"

"No," I mumbled.

"Because we seek dominance over both sexes, and with you we get a two-for-one deal. You've been fucked before, of course?"

"I haven't!" I protested.

"I find it hard to believe," said Gordon, shaking his head sceptically, "That some young buck hasn't made you his bitch before now?"

"He has," I confessed, "But he never fucked me, at least not in the way you mean. He certainly fucked up my life!" Then I forgot myself, and told Gordon the whole story of what had happened at college. I spoke as if to an old, trusted friend, rather than someone I'd only known for a couple of days.

"And the worst of it is," I concluded, "That whilst I was expelled and had to leave home, he got off with a slap on the wrist! He's still there, and something of a hero. In fact, I think if anything then this whole business has made him even more popular."

"Of course it has," Gordon chuckled. "You see, he's a real man and all he's guilty of is using you the way nature intended him to. And who's going to blame him for that?"

I said nothing in reply, but merely blushed. He allowed himself a wry smile, then continued..

"You're quite right to say it's unfair," he conceded, "Because in letting him use you as his bitch, you too were only obeying nature. But the world is a hypocritical place; it's terribly unfair, but the dice are heavily loaded against pathetic creatures like you."

He paused to light a cigarette, watching me carefully the whole time..

"But of course" he continued at length, "You've noticed this already. I mean, look at you -- everything about you is sublimely effeminate. And frankly," he chuckled wryly, "Your efforts to pretend you're straight are comical! If only you could hear half of what's said about you behind your back, then you wouldn't waste your time. And that brings me neatly to a couple of points I want you to take on board."

"What are they?" I asked meekly.

At first he didn't answer, just gave me another of his wry, sideways glances. He stood up and very casually began to undress, placing his clothes neatly atop the dressing-table.

As he took off his boxers, his stiff, fat cock popped out like a jack-in-the-box. It was pointing towards me like a loaded gun with a smidgin of oil glistening on the barrel.

"I'm going to fuck you in a moment," he said, "Do you have any lubricant?"

"No," I replied.

"How about hand cream?"

"There's some in that drawer," I said, pointing.

Smiling, Gordon found my hand cream and spread half the tub generously onto the stem of his bulging manhood.

"Turn over onto your tummy," he said, "And pull those tights down onto your thighs. Then spread your legs apart." Without a word, I did everything just as he'd asked, and received an approving grunt. He clambered on top of me, placing a firm hand on each of my arms so that I was pinioned, face down.

"Before I start," he said, "I want to say something about Mary. She's a nice kid who deserves a real man, so you should leave her alone! There are plenty of lads here who can give her what she needs, but you're not one of them and never can be. You've just been using her to pretend you're something you're not, which is dishonest. So give it up, okay?"

"Okay," I replied meekly.

"Good girl!" he said, slipping his firm cock between my quivering butt-cheeks without further ado.

I gasped. That first thrust that took my anal virginity struck a raw nerve, and I quailed at the thought of what might follow. But as he began to plunge in and out of me, I quickly relaxed. It not only felt pleasant, but wholly natural.

Indeed, the more he pumped away at my tight little ass, the more I began to groan with pleasure. At the same time, his breathing got heavier, and began to tease the back of my neck. Then he too began to groan. At first it was just a low murmur, but it soon grew louder.

And then, out of nowhere, he suddenly grasped my hair, pulled my head off the pillow and let out a loud moan of intense pleasure. As he did so, I felt the first spurt of warm cum surge into my tender bumhole. A deluge soon followed, with plenty left to bubble past the broken vacuum of my burning rim.

Gordon pulled out and stood beside the bed, looking down upon me in a rather perplexing manner that suggested he thought I owed him something.

"What's wrong?" I asked.

"Nothing," he replied, "Except you haven't finished."

"Haven't I?"

"No!"

He pointed to his cock, which was dripping with cum, and I began to understand. Slipping off the bed, I got down on my knees and, taking his shrivelling manhood in my hands, sucked our salty, commingled juices off it.

"That's better," he said, and began to dress.

"Before you go," I mumbled, "You said you'd tell me a couple of things, but you only told me about Mary."

"Yes," he replied gravely, "Poor little Mary, harbouring the delusion you're her boyfriend! I expect you to put her right tomorrow."

"I will!" I promised.

"See that you do! The other thing's simple enough, yet very serious. As you come to terms with yourself as a transsexual, you're bound to think of having the snip. Don't do it!"

"Why ever not?" I gasped. He was perfectly right. All my life I'd wanted to be a girl. As a small child, I'd believed Jesus had made a terrible mistake and had prayed nightly that I might only wake to find that He had put it right. And losing my anal virginity had only stirred such feelings with a vengeance.

"Because," he explained, "You'll lose your greatest asset! You see, at the moment, you're considered hot by real men because you're a bit of both. But without this," he said solemnly, reaching down to give my tiny cock a condescending pat, "You're neither one thing nor the other -- and no alpha male's going to waste his time on that! So by all means take the hormones and get your boobs fixed, but hang onto your valuables all the same!"

Saying which, Gordon took his leave. Too tired to shower, I simply turned off the light and dived under the bedclothes, still wearing my pretty pink bra, panties and tights sticky with my own dry cum.

It was hardly surprising that I dreamt of Gordon. My ass was full of his cum and the aftertaste of our commingled juices lingered on my tongue. Yet the dream was sweet, even if he wouldn't have approved of the sex change it included.

In the morning, I took a long, steamy shower and went to work as usual, struggling through the day with my regular act, though it pained me to realize how ridiculously unconvincing it was. I now saw the snide smiles and sideways glances of my manager and co-workers, and understood that Gordon had been right -- that I'd fooled no one.

At suppertime, I sat as always beside Mary. We'd planned to go to the cinema that night, but I knew I had first to do some explaining. Yet there was really no need, it was obvious from her demeanour that we were through.

"About tonight.." I began lamely.

"I'm going with someone else," she blurted. As she spoke she glanced balefully across the table at Gordon, and I realized she knew something.

"Don't worry," he chipped in mischievously, "I'm sure I can find something for you to do instead."

Hearing this, everyone at our table sniggered, except for Mary who just looked embarrassed. It was clear they all knew more or less everything, and probably from Gordon! Because just like the college bully, he as an alpha male had no need of shame.

"I'm sure you will," I mumbled sheepishly.

And I was right.