tagTranssexuals & CrossdressersFirst Time, From A Window

First Time, From A Window


You know, I remember the first time I saw you. You lived in my street - you'd only moved in a few months before. I sort of knew you were around, but I don't ever really recall seeing you or meeting you.

For a quiet cul-de-sac, we had more than our fair share of single women living around, and we'd formed into a firm group of friends. The first time I saw you, they'd had a barbecue in Karen's secluded garden. The only house overlooking it was mine – I was watching enviously from my bed, feeling ill and sorry for myself as they enjoyed themselves.

Of course, as the new man on the street, you were very much the object of all our attentions. Tales of your good looks had spilled eagerly from Jacqui's lips, and she had very high standards indeed. So when they heard your car pull up, Karen was out of her seat and down the driveway before anybody could tell her to put something on over her bikini.

I assumed she introduced herself as she said a few words to you and you nodded. Even from my window I could see your wide eyes drinking in her gorgeous figure. You shook hands, and I could see her inviting you to the gathering.

You nodded, smiled, and followed her round into the garden, where the girls surrounded you. They were all a couple of years older than you, and slightly taller. You looked overawed as they fussed and cooed around you, their hands brushing you. Karen said something I couldn't hear, and they all laughed. Somehow the intense flirting assumed a new aspect. I'd never considered them cruel, but today they looked a little mean.

My vantage point was close enough so that by opening my window slightly I could hear every word they said.

Karen moved in for a kiss as the purple-haired Goth women from number 8 held your arms, forcing you to remain in place. Your struggles were somewhat feeble, I thought, but that weakness transfixed me. I enjoyed watching you being held captive by the pale women, taking a dark pleasure in becoming aroused by your ineffectual struggles.

Karen wasted no more time, leaning in to a long, smooching kiss dripping with breathless passion and hot tongue. Her lip lock was obscene, and her hands roamed your helpless body - under your white T-shirt and across your chest.

The other women were reddening and their eyes hooded as they watched the display Karen and you were putting on. Some of them began rubbing their crotches, almost unconsciously.

As Karen's hand started to brush across your groin I heard you moan. The noise lit a fire inside me and I discovered my fingers had been rubbing my nipples until they sprang up, fully erect. I felt so naughty watching you, but I couldn't tear my gaze away.

Karen's soft fingers found a purpose, and she undid your belt, popped the button and tugged the zip of your black jeans. They slid down your legs and around your ankles. Beneath them, your long sleek hairless legs looked pale in the sunshine.

You were making grunting noises as if protesting, but the words - if you had any - were lost in the sweet hollow of Karen's mouth as the continued her onslaught.

She hooked her thumb into the waistband of your shorts and tugged them, ignoring your indignant squeals. Your cock popped out, bright red and stiff from your humiliation at the hands of my friends.

By now I'd abandoned my nipples in favour of insinuating fingertips onto my clitoris. I panted as I saw your bobbing member betray your excitement and heap shame on you.

Pammi and Siu were giggling now - and as Karen snogged you even harder, the three other women began taking off your other clothes. In short order, you were naked, pinned against the ground by Pammi and Siu. Sitting on your arms, they moved back and forth gently. I guessed they were grinding their hot little clits against you. They wore matching short puff skirts in a transparent black material. I could see Pammi's stocking-tops and black knickers clearly as her skirt rode up her thighs.

Jacqui, meanwhile, was stripping. Her outerwear almost fell from her – and underneath she looked stunning. A white satin bra, knickers and suspender belt, all trimmed with white lace and frothing with ribbons. I couldn't believe she'd dressed that way for a barbecue, and I suddenly wondered how well I knew my friends. Were Pammi and Siu lovers? They were certainly leaning over to kiss each other, still grinding their groins against your splayed arms as their slick crimson lips skid against each other.

As I watched, Jacqui removed her underwear and stockings, handing them to Karen. Alicia, Karen's older sister, stepped forward and Karen motioned her to sit on your chest. And as you struggled beneath three girls, she began putting them on you.

I heard you protest and ask her to stop, but in a stern tone she told you if you were going to play with the girls, you had to become a girl yourself.

As you were about to argue, Alicia moved forward onto your face. She began rubbing her crotch over you, and flicked out her pleated blue skirt to hide your face.

Karen got the stockings on your feebly struggling legs and carefully pulled Jacqui's still-warm knickers over one ankle, then the other. She drew them up your form, slowing as she came to your erection. When she slid the silk over your arousal, she gently rubbed it with her palm. I heard you moan – a sound echoed by redheaded Alicia riding your face.

Karen called you a little slut, and the name triggered my first orgasm. Here was a boy slut, an easy lay. All he needed was stockings and knickers and girls could do what they wanted to him. I soaked my fingers as I clenched my teeth to stay quiet.

My mind was feverish as my fingers danced across my burning clit. A submissive boy, a smooth girlish boy, feminised and used by... well, by me! It hit me like lightning, and set off another orgasm. I was envious of the females controlling your writhing form.

I wanted to be the one sat on your face. I felt so naughty as I imagined what your nose would feel like as I dragged my hot clit across it. I wondered how your hot breath would feel against my opening as I teased you through satiny knickers. And if I was to look back...

I shuddered into my third peak in just minutes. If I were to look back, I'd see your slender stocking-clad limbs pounding the ground impotently. Your straining cock inside its maddening silky finery. And all the while your desperate groans would leak from the mouth clamped to my sopping wet hole.

I opened my eyes in time to see Alicia orgasm much as I had just done. She suddenly clamped the sides of your head with her knees as she shook her way through the climax, face contorted with the pleasure of it.

Karen busied herself at your crotch, licking the solid bulge that threatened to burst through the smooth satin. Her eyes closed as her tongue danced along your length, her hot breath playing over your skin.

You writhed beneath her, your thighs pressed together and thrusting up towards her tongue. You were desperate for her touch, for her mouth, and for her control. With erotic leisure, she painted your rod with saliva as you all but sobbed with pleasure.

Inevitably, my mind turned to what it would feel like to be Karen. To have your trembling form in my power. I could force those gasping breaths from you – just as she did. It would be my lips you were trying to bruise with your satin-slick member. My tongue lazily sweeping across your most sensitive zones, and also mine would be your throaty cries of pleasure.

Pammi and Siu were now masturbating openly as you allowed Karen to ravish your pole orally. They rubbed their wet slits along your arms, shuddering as their clits slid against you.

Alicia was coming again, and she hiked up her skirt to reveal not only was she not wearing knickers, but she'd soaked your face with her wetness. She twitched and gasped, face screwed into a mask of rapture, as another orgasm hit her. My questing fingers were all over my clit and I pumped two fingers deep inside me, looking for my spot.

At that point, Jacqui joined the party. She'd vanished for a minute or two – and now I saw why. She strode confidently towards you, a strapon cock bouncing obscenely between her legs as she approached.

Karen moved around to your side, her lips locked to the tip of your cock. Jacqui dropped to her knees and held your legs high as she shuffled in. Holding your knickers to one side, she placed the tip of the toy against your entrance.

As she pushed, a series of three short squeals told me the story. One, you weren't expecting to feel a greased cock wielded by a woman sliding deep inside you. Two, having a long, slim vibrating pole pushed into your arse by a beautiful blonde wasn't as painful as you'd have guessed. And three – oh, I gasped into another orgasm as I realised what your third girlish cry meant – that you liked it.

Jacqui showed very little mercy. As soon as she was inside you, I could tell she was determined to give you a royal fucking. Slowly withdrawing until just the head was inside you, she suddenly thrust forward again. Her hips slammed into you, snatching your breath. I sobbed in frustration as my fingers pinched my clitoris. Jacqui ground herself against your buttocks in slow circles, and I wondered how that would feel.

I imagined myself filling your tight little hole, teasing your prostate with my cock and having you surrender to me. I wanted your scorching hot feminised arse to feel my hips against it, to show you how much cock I'd fed you. You'd be my willing fucktoy, groaning with pleasure as I fulfilled my kinkiest fantasies with your body.

With no warning, you let out a high pitched squeal that must have sent delicious vibrations through Alicia's pelvis. Under Karen's eager ministrations, your dick bobbed and dipped.

Jacqui slammed into you, over and over, as she grunted through a climax. Karen's hand was rubbing against her slit, even while she struggled to keep sucking your hardness through the satin material. As Jacqui forced her way into you one last time, she seemed to set off a wave of pleasure that had your cock spurting.

Karen's eyes widened for a second as the blasts of sperm filled your knickers. Pulling the waistband, she managed to move the skimpy undies aside to kiss your throbbing member. Taking a tiny lick of your juice from the tip of your cock, she started to laugh as she declared you a sissified bitch.

That, I think, is when I understood how much you loved the humiliation of it all. I could see why being dressed in lingerie and forced to cum might excite you. But my scandalising realisation was that dressing you in lingerie and forcing you to cum would excite me. And that knowledge – along with my busy fingers – pushed me through a door into a world of joy, bliss and ecstasy that I'd never imagined could exist.

I remember the first time I saw you because it was the first time I wanted to feminise you.

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