Nights In White Satin

The back door quietly opened—just by a crack at first, then gradually swinging wide. Greg was well practised in his furtive nocturnal adventures. While there was a thrill to be had in the risk of discovery, the last thing he ever wanted was actually to be caught. He'd often imagined what it would be like to be found out, and just the thought of it was enough to leave him sick to the pit of his stomach. There had been a time where it had given him a sufficient buzz to confine his activities to the privacy of his own bedroom, but once the idea of going outside had occurred there had been no resisting the temptation.

He slowly walked down the path along the side of the house, stepping carefully to avoid his footwear treacherously giving him away. It had taken him ages to be able to walk in his mother's high heels, but that tell-tale click-clack was the last thing he needed on nights like these. The bushes that separated the path from the street provided excellent camouflage, so he paused to admire his reflection in a downstairs window.

He stood, arms akimbo, his mouth dry and the breath rasping in his throat, feeling simultaneously elated and appalled. Slowly he ran his hands over his skirt, relishing the firm feel of his body securely constrained in his mother's roll-on girdle and sighing with pleasure. How could something so wrong feel so good? He turned round to look over his shoulder at his ghostly reflection, nodding approvingly at the ruler-straight seams of his stockings. There was a time where they'd have been all over the place, but practice makes perfect. He slowly raised the hem of his skirt and petticoat to show his stocking tops, securely attached to his girdle garters. Doing a full pirouette, he was delighted to see all six garters dead straight—even the tricky rear ones.

He let the skirt fall again, and raised his eyes to admire the bust he had contrived for himself under his blouse. His longline bra overlapped the waist of the girdle all the way round, avoiding any unsightly bulge of flesh spoiling the smoothness of his figure. The balled-up socks stuffed into the bra cups gave him a substantial bosom—his mother was well-endowed, and his boy boobs would have struggled to fill a B-cup.

Having passed muster, his attention turned back to the road. The alarm clock had read 2:37am as he'd tiptoed out of his bedroom, so unsurprisingly the street was completely deserted. Yet his heart hammered in his chest as he made his way to the front gate, moving from the safety of the shadows into the full glare of the street light. He stepped off the pavement and started crossing the road, and on reaching the other side, he paused, almost unable to comprehend the achievement. He'd slowly extended his range each time, and this was as far as he'd ever gone. He stood there for a moment, resplendent in his white blouse and navy pencil skirt, and looked longingly down the street to the corner shop at the far end. He hadn't intended to go that far tonight, but now he couldn't help himself. First one step then another, and he was on his way.

Part of him was in a panic - it would just take someone to come to a window, or a car to turn into the street, and it would be over. But the thrill-seeker in him refused to turn back. He felt the chill of the cool night breeze against his bare arms and the exposed tops of his thighs as he continued, and soon he was closer to the shop than he was to his house. Arriving at the shop, he admired his reflection in the large window. Under the bright street lighting, the window was as good as a mirror. He slowly lifted his skirt to expose his girdle and stockings, grinning uncontrollably, absolutely intoxicated and totally lost in the moment.

And, as he smoothed down his skirt and lifted his eyes, the grin froze on his face and terror washed over him as he saw himself displayed with crystal clarity on the security monitor, his performance now safely recorded for posterity.

Note ▼

As anyone who's read my autobiographical stuff knows, when I was a teenage boy I was coerced into wearing women's shapewear. As you can imagine, this was an extremely difficult period in my life. I decided to try to write a scene from the point of view of a boy who actually wanted to cross-dress and who got a kick out of risking being caught. Getting into that diametrically opposite mindset was definitely a challenge—this is the result.