Barbara's Binoculars

"Pad your bra out!" Barbara ordered, passing me my socks. I did as she commanded and was then given a pair of black, thigh-high faux leather boots to wear. They looked great, and I was keen to try them on, but was dismayed to discover they too were size five!

"They'll kill me!" I wailed, but Barbara was unsympathetic.

"My Frank will kill you if you're not careful!" she replied, to titters from Kim and Tracy. "You're getting far too stroppy for my liking, and if I were you, I'd be more careful from now on!"

Quivering at the thought of what Frank would do to me if he saw me dressed like this, I became contrite and squeezed into the boots with firmly buttoned lips!

Once again we went to the mall, with me feeling much more confident this time, in my stylish polka dot mini dress and attractive hat and boots. If only my feet hadn't hurt so badly, I might even have begun to enjoy myself!

Like the previous day, we sat for a while with the other students in the plaza; only this time, the attention I was getting was far less unwelcome...

Especially from John!

Wearing shades indoors under bright neon lights and carrying his motorbike helmet, he oozed leather and testosterone, and my thighs trembled whenever he appeared to pay me special attention. Of course, what he'd have done if he'd known who I really was is anybody's guess...

But he clearly had no idea!

"Have a cigarette!" he said, offering me a Marlboro, and I took one even though I didn't smoke!

"You're not from round here are you?" he asked.

"N-no! No I'm not!"

I was so hopelessly tongue-tied, I could say no more! John smiled into my eyes in a way that was beginning to get serious, and when he put his arm on the seat just behind my shoulder, a hot flush made my cheeks turn bright crimson!

But if John was starting to have ideas about me, Barbara had others...

"Come on Sissy," she interrupted rudely, "It's time to go! We've work to do!"

The thought of meeting those burly and abusive security guards again wiped the smile straight off my face, and I must have looked woeful and forlorn as John watched me disappear up the escalator with an increasingly furrowed brow.

"This time, we're gonna do the off-licence," Barbara explained in a conspiratorial whisper. "Take this large bag, cos you're gonna do the robbing! We'll keep the boys busy while you nick us some vodka!"

Quaking with trepidation, I entered the off-licence, ignoring the lurid smiles of two young male shop assistants who lounged idly behind the counter. I was beginning to worry they might be a little too interested in me, but Barbara, Kim and Tracy soon came in behind me and stole their attention, leaving me free to steal their stock!

A selection of vodkas sat on a shelf at the perfect height for me to purloin them into Barbara's bag, so while the girls swapped inane banter with those two increasingly distracted young guys, I was able to deftly slip three bottles of booze into the soon bulging shoulder bag.

Although I was pleased how smoothly my first venture into shoplifting had gone, I was still nervous I wouldn't get away with it. And as I began to leave the store, my anxiety increased exponentially. Every painful step caused a distinct clank from the bag that was impossible to ignore, even for a pair of randy shop assistants being distracted by three hot girls!

Passing the counter, I could hear Barbara and the others starting to say their goodbyes. I'd almost reached the door when suddenly, instead of chatter there was stony silence, which was soon shattered by the words I'd hoped and prayed never to hear...

"Where do you think you're going, miss?"

I tried to run, but there were two of them and I had tortured toes and a bag that weighed more than a millstone! Before I knew what was going on, I was being escorted back inside the off-licence, while my three accomplices just strolled casually away, leaving me to face the consequences of their actions alone; though on her way out, Barbara treated me to a particularly murderous glance!

I had failed her! But what would be the price?

I would find out soon enough; for now though, I had more immediate worries. My bag was searched, the vodka recovered and placed upon the counter.

"We've been a naughty girl, haven't we?" sighed the guy holding my arm firmly, while his colleague shook his head. "Well, what's it to be?"

"W-what do you mean?" I asked naively.

"You must be new here!" he laughed. "This shop has a policy of payment in kind! Otherwise, it's the police..."

"N-no!" I cried, "Not the police!"

With a broad smile, the guy holding me led me behind the counter into a storeroom. It was cram-packed with boxes of booze and cigarettes, but there was just enough room inside for two people, at a squeeze. He told me to kneel down and wasted no time unbuckling his belt and placing his burgeoning manhood right before my frightened face.

"You know what to do," he sneered, "so get on with it!"

He was hopelessly wrong; I had no idea what to do! I was still a virgin, and my vague interest in men's anatomies was rooted not in experience, but in my desire to be a woman. Noticing a drop of pre-cum glistening on the end of his ramrod stiff cock I tentatively licked it, recoiling immediately at the rich, salty taste.

"Get a move on!" he grumbled. "We're only allowed ten minute breaks!"

Fighting back tears, I pursed my lips and ran them up and down his throbbing cock, trembling at how much flesh there was! His member seemed massive compared to my puny thing, and I couldn't figure out how it was all going to fit inside my mouth...

Though I would soon find out!

"That's better! Now blow a bit!"

His request surprised me, as I was already panting furiously! But I tried to comply, and moved my cheeks in such a way that his cherry got a lot more ventilation. The effort caused me to gasp and gurgle, but far from putting him off, this seemed to satisfy him all the more!

"Yeah, that's nice!"

So saying, he placed his hands on the back of my cloche hat and forced me further onto him. I gagged and tried my best to pull away, but his iron grip held me firmly in place...

And besides, there was nowhere I could go!

Moments after he'd grabbed me and forced his cock into the back of my throat, I felt his cherry burst, and I got my first proper taste of hot, creamy cum as his generous load spurted furiously past my tonsils.

He withdrew just in time to watch me retch as I spat the cum I hadn't swallowed onto the floor of that dark and dingy storeroom.

"I hope that will teach you it's wrong to steal!" he joked, and both of them laughed at me as I left the shop with little dignity and even less vodka!

Back at the old manor house, Barbara had no sympathy for my terrible ordeal.

"What's your problem?" she sneered. "A sissy like you should have enjoyed it! But where's our booze, that's what I want to know?"

I fretted for a few moments that she was going to get nasty with me, but eventually she calmed down and let me go home. And before I left, she told me something uncharacteristically nice.

"After you got caught, we were talking to that John again," she said. "He says he really likes you and he'd like to take you out! You'd like that, wouldn't you?"

I blushed. The truth was, I had a massive crush on John, but I knew it was hopeless. He was popular with all the girls, and when he found out about me...

"I told him who you really are," she continued, "and he says it doesn't matter; he'd still like to go out with you!"

These words were ringing in my ears all the way home! I hardly even noticed my swollen toes, such was my happiness at the idea that John might accept me for who I am! The following day I was elated from the moment I woke up. I couldn't wait for college to end, and the instant my final class was over I almost danced to the old manor house!

Barbara and the girls seemed strangely cheerful. As usual they chatted idly while smoking and drinking cider as I undressed, stripping down to my skimpy red bra and panties. I waited patiently to be given some clothes to wear, but today I was in for a little surprise...

"You can take them off as well," Barbara announced nonchalantly. "We'll try something different!"

I did as commanded, and was given a leather thong to put on. I have already explained how I was never well-endowed, but this tight, tiny garment squeezed me in a way that was most uncomfortable. It was also hopelessly impractical as my bits hung out, but when I tried to protest, Barbara scowled so coldly I decided to say nothing more.

I was given no bra, just a satin camisole to wear beneath a lacy black blouse. A leather miniskirt finished the outfit, along with the black tights and thigh-high leather boots I'd worn the day before. And Kim did my make-up quite differently, using a much more natural lipstick, no eye-liner and only a smattering of mascara.

"What do you think?" Barbara asked.

"I'm worried people will guess who I am!" I fretted. But then she reminded me John already knew who I was! With my heart fluttering, I decided to put all my doubts aside and trust to providence...

A dumb mistake!

Instead of heading down to the mall, we walked round the corner to the arcade, a colonnade of shops built to service the estate, all boarded up and sprayed with graffiti. Only the public toilets remained open, and they had an ugly reputation for casual encounters of the kind that got folk into trouble! Students sometimes hung out there, but we had to be careful; the police often checked out those toilets!

Even in the dark, I could clearly see John standing under the arcade; he was the tall, handsome guy wearing shades! Walking towards him, I was so excited I thought my legs would turn to jelly, but when I got closer, I saw he didn't look quite so pleased to see me.

"Hello Sissy," he said, sounding uncomfortably reserved. "You look... different!"

I blanched, painfully aware he was ogling my conspicuously flat chest! At that very moment Kim snickered, and I realized she'd used far less make-up so I'd be recognized! Still, despite some obvious reservations John handed me his spare helmet and invited me to get on the back of his motorbike...

We rode through the night for about ten minutes, and I was in heaven! I clung to John while the motorbike weaved around with the wind tickling my nylon-clad knees. When he finally pulled over, we were on the outskirts of town, at a little park by the river that was popular with young lovers.

He took me down a dark path towards a bench. We could see each other only by moonlight, but even so I could feel his tension; he was like a live wire waiting to be earthed!

"What's the matter?" I asked timidly.

"I know who you are," he simmered. "I recognized you back at the arcade and I really ought to kill you!"

"I'm so sorry!" I blurted tearfully, "They told me you knew!"

"I guessed as much!" he cursed. "Those bloody bitches! It's not your fault, but I've got my reputation to think about, so I'm afraid I'm gonna have to beat you up!"

Tearfully, I told him I understood and would passively submit, pleading only that he should do nothing that would permanently mark my face. My willing acquiescence seemed to mollify him, and I felt his attitude begin to change.

"I don't want to hurt you," he said eventually, "I'd rather try something else instead! None of my girlfriends has ever let me have anal sex, and as you look so feminine..."

I readily agreed and saw his teeth glint in the moonlight as he honoured me with the fullest smile I'd ever seen on his ruggedly handsome face!

We got back on the motorbike and John rode off the beaten track to an isolated spot on the riverbank. Once there, he propped the motorbike on its stand so it was firm and steady, then asked me to bend over the seat.

Feeling his hands lifting the hem of my short leather miniskirt made me incredibly horny, and my own feeble cock began to stir. He noticed this while pulling my tights and thong out of his way, and gave me a nice little pat that sent spasms of excitement shuddering through my body. When he let go, my boy-bit had grown to its modest maximum and was dripping pre-cum copiously onto the warm motorbike engine, which fizzled!

"This is going to hurt," John explained apologetically, "I didn't bring any lube, so I'm just using a bit of grease I've scraped off the front forks!"

"Okay!" I replied. "Maybe I can help?"

Our chemistry was so great that John understood immediately what I meant! Putting his hand back under the front of my short leather miniskirt, he grabbed hold of my tiny cock and gave it a few tugs. Just the touch of his fingers while his hot breath rubbed the nape of my neck was enough to send me into paroxysms of ecstasy, and almost immediately my tiny cherry began spurting cream across the leather seat as the greatest orgasm I've ever experienced turned my whole body from the hips down into a tremulous tub of jelly!

Without saying a word, John scooped my cum off the seat and mixed it with the grease already melting in his warm, manly hands. A coarse finger gently rubbed some of this improvised embrocation around the rim of my tight virginal pussy, then at last I felt his burgeoning ramrod begin to force its way inside me.

I gasped, overwhelmed by a wonderful mixture of pain and pleasure! John was well hung and well practised in every form of sex except this, and he really knew how to keep a girl happy! Every second he pounded me caused an ecstatic groan, as the woman deep within me expressed her satisfaction!

But all good things must end, and all too soon I felt a warm spurt deep within as John offloaded his hot cum into my quivering pussy. Pulling up his trousers, he looked pleased with himself, and I was truly glad to have been the one who opened his eyes to yet another of life's endless opportunities!

But now, it was time to go...

I asked John to drop me off at the old manor house where, to my surprise and horror, I found Frank waiting for me alongside his sister!

"Well fuck me, just look at this!" he sneered, squaring up to me with spit flying from his snarling teeth. His fists were clenched and I instinctively cowered, terrified of what he might do now he had me utterly at his mercy!

"I told you if you weren't good to me I'd tell Frank!" Barbara proclaimed sanctimoniously. "And what did you do? Wash my bra and panties without permission and then lose those lovely bottles of vodka! You've been nothing but trouble and I'm just glad you're now gonna get what you deserve!"

While Kim and Tracy watched and giggled, Barbara laid out her skimpy red bra and panties on the filthy floorboards. Next, Frank unzipped his fly and, laughing voraciously, pissed all over the lingerie till they were steaming and sodden.

"Get your clothes off!" Barbara commanded, and I had a horrible feeling I knew what was coming next...

But luckily, I was wrong!

Before I'd had a chance to touch a single button on my blouse, a creaking stair caught everyone's attention and we turned to see John entering the room!

"Stay as you are!" he shouted at me, before thumping Frank so hard he fell to the ground and curled into a foetal position, which he obstinately refused to relinquish. "Sissy's my friend, and anyone who's got a problem with her needs to come and see me!" he proclaimed, letting those lowlifes know I was under his protection.

With her brother curled up on the floor like a big, ugly baby, Barbara became remarkably contrite, at least until John left. Then she tried getting nasty with me again...

"I'm still gonna tell everyone about you!" she bitched. "Starting with your mother!"

"You needn't bother," I replied, "I'll tell her myself!" And so saying I walked out of the old manor house for the very last time, still dressed in the silk blouse and leather miniskirt I'd lost my virginity in!

That night I told mother everything, but there wasn't much she hadn't already guessed! Then the next morning I went to college as Sissy, stopping on my way to buy a nice pair of shoes that fitted properly! Of course I was expelled and life got really hard after that, but things are better now. The world has moved on, and nowadays people can be themselves...

Which is all that really counts!