Troy
by Its a skirt, not a kilt
Copyright© 2009 by Its a skirt, not a kilt
Erotica Sex Story: A boy tries on his sisters wedding dress, only to be discovered by the groom to be...
Caution: This Erotica Sex Story contains strong sexual content, including Ma/mt CrossDressing Anal Sex .
Troy's mouth was dry, his heart beating wildly in his chest. He had never felt this level of anticipation since he was little and lying in bed on Christmas Eve. Palm damp with sweat, he slowly opened his sisters door.
The room was pretty much the way it always was, neat, tidy, everything in its allotted place. He ignored the dressing table with its attached mirror and drawers half full with plain cotton underwear. It had contained sexier garments, but when his sister had moved out into her boyfriends (soon to be husband) flat, she had taken all the sexier items, leaving the plain ones behind.
His goal lay hung up in her wardrobe. It's very nature meaning that, for the moment, it had to stay at her parents' house.
Troy could not believe his hands actually trembled as he slid the mirrored door of the built in wardrobe back. The door sliding back in a near silent whisper.
Like her drawers, the wardrobe was mostly empty, a few plain dresses and some clothes that no longer fitted. One item stood out, encased in clear protective wrapping. A bright white silk and lace wedding dress.
Just looking at it made him hard. He had seen it before; in fact it was impossible to avoid anything wedding related in the house at the moment. Next to the dress was another hangar with a protective cover. This was his suit. His mother did not trust him not to get it dirty before the wedding, so it hung in his sister's wardrobe for safety. But his suit held no interest, reminding him of several uncomfortable days trying on various suits in various shops.
By his reckoning, this would be the only time he would get a chance to try it on before the wedding in a few days. His sister and parents were out finalising last minute details about the church and the reception and he had a few hours at least to spare.
He lifted the hangar off the rail, surprised at the weight of the dress, and laid it across his sister's bed. He stood for a moment, looking down upon it. He had never seen something so beautiful.
Grabbing the bottom of his hoody, he quickly pulled it, and the T-shirt underneath, over his head. Letting the bundle of mundane boy clothes fall to the floor, he undid his jeans and hastily pulled them off.
Troy had been planning this for a few days and had come prepared. He stood in front of the dress clad in a white lacy bra padded out with some old tights; white lace panty shorts hugged his hips. Under the lace shorts, the straps of a suspender belt lay pressed into his skin, the clips terminating in the lace of a pair of white lace top stockings.
His young form and long hair looked feminine from the rear, until he turned around, his prominent erection pushing out the front of his lace panties. Troy couldn't help running a hand over his erection as he continued to stare down at the dress, savouring the moment.
Opening the zip on the dress protector he removed another bag. This one contained the veil and garter. With a smile of joy, he placed a white nylon clad foot on the bed, lifting it again to slip the garter over his foot. Leaning slightly on his raised leg, he slowly slid the garter up his smooth leg, pretending he was doing it for an audience, like a strip tease in reverse.
Placing his foot back on the bedroom floor, he paused to admire his reflection and how good the garter looked on his leg. He blew his image a kiss.
As he removed the dress from its protection, he marvelled again at how heavy it was. The silk slipped through his fingers, the skirt soft with layer after layer of underskirt. The bodice was lightly boned, draped in lace and covered in little pearls. There was more lace on the shoulders, with a ribbon tied in a bow under three white silk roses adorning each shoulder.
Troy slipped the dress from the hangar and unzipped the back.
He was now fully erect, his cock demanding attention, but he knew that this would probably be his only chance and fought down the desire to release his erection and stroke himself to explosive discharge.
Lowering the skirt to the floor, he stepped into the ring of white silk and lace. Gradually, bit by bit, Troy pulled the dress up his legs. The feeling of the material against his stocking clad legs was almost enough to make him orgasm there and then. He watched his reflection as he slipped his arms through the shoulders and shrugged the dress into position. He settled the shoulders into place and couldn't resist running his palms over his fake breasts, over his stomach and down the front of the skirt. For a moment his hardness was visible under the skirts many layers.
He had to admit that his reflection looked stunning.
Yet, with the zip still sat at his lower back, the bodice's boning was loose and unsupportive. He swished back over to the wardrobe, excited at how his legs were caressed by the skirts whispering fabric. The inbuilt train of the dress rustled behind as he walked.
He had spent many a happy year dressing up in his sisters clothes. Revelling in the feel of her party and going out dresses, excited by the short hems and how they forced him to sit demurely down, legs crossed. Occasionally he would part his legs, knowing that the shortness of the skirts would reveal his panty covered crotch to view. He imagined that he was at a pub or a club, that there were others watching him. He loved how, if he was wearing stockings, that when he bent over, hems would rise to reveal the stocking tops.
He enjoyed watching his sister leave the house on a night out, watching as how some of her dresses clung to the contours of her shapely body, how that the material of some of her dresses were so sheer that they revealed an absence of underwear.
The knowledge that she had worn those dresses, seen what they looked like on a female body, knew that male hands had explored the dresses boundaries and the female flesh underneath, had always resulted in intense orgasms. He had even made a point that if she had worn underwear on a night out, that he found them and slipped them on over his own flesh before they were washed, pretending to be her, imagining those roaming hands against his own virgin skin.
Troy stretched up on his toes and reached towards the back of the topmost shelf. After a moment, his questing fingers found what he was looking for. He lacked the grace and dexterity of his sister and the zips on many dresses defied his meagre contortionist skills. To overcome that hurdle, he kept a small length of wire in his sister's wardrobe. Placing the hook in the wires end through the zip, he reached backwards over his shoulders and slowly pulled the wire and zip upwards.
As the zip slowly closed, he felt the bodice slowly close around his chest like a clam. He sucked in his chest to facilitate the zips closure.
Toy studied his image in the mirror. With the zip now closed the bodice defined the narrowness of his waist, the skirt emphasising his hips, the light boning of the bodice supporting his bust.
The bodice also acted like a corset restricting his breathing, forcing him to take quick shallow breaths, the enforced hyperventilation making him light headed. He made his way back to the bed, surprised at how the boning of the bodice forced a change in his posture. He had never felt so feminine before, ever. He made to bend over for the veil, but the boning rods dug into his flesh and he found himself bending his knees instead, fabric teasingly sliding over his nylon clad knees in a seductive silken brush.
Picking up the tiara with its veil, he placed it onto his head as he straightened and turned back to the wardrobes full length mirror. With a few minor adjustments he had it in place and dropped the veil across his face. With his male face partly hidden, he looked like the virgin bride of his dreams.
He thought of his sister similarly attired. He didn't know what his sister would wear under the dress; the details had been discussed in quiet tones just out of hearing and to repeated giggles from both his sister and his mum. He thought of her impending husbands roving hands caressing her body under the dress that he was wearing. Imagined those hands against her breasts, imagined that it was his body under the new husbands touch, imagined those hands travelling down, slipping under the heavy material of the skirt, coming to rest against his legs, touching and stroking as they travelled up towards his thighs.
Troy felt his knees weaken, his breath almost nonexistent, his pulse thumping throughout his body. He had to have release now; he was so close to coming in his sister's panties. He opened his eyes that had dropped shut as he imagined the groom doing what he wished with the brides —Troy's- body, into a face that stared back.
Except that it wasn't his face that Troy saw. It was that of the groom to be, and he was standing in the doorway...
Troy whirled around. Sure enough, the groom to be-Jack- was stood in the doorway. His heart stopped beating and leapt into his mouth and all colour drained from his face so he was almost as white as the dress and veil. His mind burned as he tried to come up with an excuse, a reason to be stood in his sister's bedroom wearing her wedding dress. None were forthcoming. As a last ditch effort, he considered the possibility of pretending to actually be his sister.
'You know, it's deemed extremely bad luck for the groom to see the bride in her wedding dress before the wedding service. Though I'm not sure how that works with the brides younger brother ... Hmmm, what do you think ... Troy?'
Troys mouth opened and closed repeatedly behind the veil but no sound issued forth.
'She is REALY going to be pissed, you know?'
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