Thomas
Copyright© 2008 by Its a skirt, not a kilt
Chapter 1
Romantic Sex Story: Chapter 1 - After being teased into briefly wearing a dress, a young boy starts to look at his sister in a different light.
Caution: This Romantic Sex Story contains strong sexual content, including mt/ft Teenagers Romantic CrossDressing School Incest Brother Sister Masturbation Petting Slow
Thomas moved his gaze from the television screen to his sister, curled up in the armchair opposite. Her smooth legs were folded beneath the skirt of her dress, demurely covering her rather enticing thighs.
He moved his gaze back to the TV screen. A couple of mad Scotsmen were prancing around in skirts.
"I wonder what it's like?"
His sister looked over in confusion. "What?"
Thomas had not realised that he had spoken his thoughts aloud.
"What ARE you waffling on about?" She asked again.
He coloured as he pointed to the screen and the Jocks who were still cavorting about. "Just wondering why they were wearing skirts, that's all."
She moved her gaze to the screen then back to Thomas. "They're not skirts stupid, they're kilts."
"Same thing aren't they?"
She made to reply, but sighed instead.
Thomas tried to quantify his earlier statement. "I mean, why do they wear them." He paused as he tried to collect his thoughts. "I mean, why do women wear them?"
She was confused now. A state plainly displayed across her face.
Taking a firm grasp of his verbal shovel, Thomas dug himself deeper still. "I mean, you refused to wear a skirt to school and demanded the right to wear trousers, yet you wear a skirt to go into town. Look, you're sat there in a dress. Why?"
She stared at him, perplexed, not sure hat question he was actually trying to ask.
Frustration at his inability to say what he wanted, helped his hole go a little deeper. "I mean, what's the attraction of wearing a skirt?" He sat back in his chair, semi happy that half the question was out.
Lea was flummoxed. If someone had earlier asked what questions she was least expecting to answer that night, it would have been up there with 'Where do babies come from?' and anything to do with marine biology.
So unexpectedly bizarre was the question, that she actually found herself thinking about the answer. She struggled to find the words to describe the need. "Ahh, you know, well," She shrugged "Sometimes skirts are right, and some times they're not." It sounded lame even to her own ears.
Thomas stared at her blankly and incomprehensibly. "No."
She thought a bit harder. "Sometimes they just get in the road and sometimes the freedom they offer, and the feeling of air around your legs, is, well, umm," She felt herself start to blush "You know, nice." She finished weakly.
He still had the comprehension of a concrete wall.
Lea waved her arms around "You know..." She paused, thought some more, then just gave up, her hands dropping back into her lap. An uncomfortable silence descended.
The Scotsmen on the telly had buggered off in the interim, a good move on their part. Thomas felt a right plonker and stared fixatedly at the screen, seeing nothing.
Lea sighed and unlimbered her slender limbs, stood and left the room. Thomas watched her reflection on the TV screen. He wished life had a rewind and an erase button. He reached over for the remote and changed the channel lest those god-damn Jocks came back on in their god-damn skirts.
The choice on the other four channels wasn't much better. He wished his parents would get a Sky package, or at least cable. He heard his sister re-enter the room, then his world went dark, or at least, pastel with a hint of flower and the scent of something feminine. Reaching up, Thomas removed the unanticipated head covering.
It was a dress. Similar to the one Lea was wearing. He looked at her, as she laughed at him.
"What do I want with this?"
"So you can wear it, silly"
"Why in the seven hells of Basildon, would I want to do that?"
"You wanted to know what it feels like, so on you go. Wear it. It's a damn site easier than trying to explain it."
Thomas suddenly developed feet colder than the artic. "I don't think so."
"Go on, you big woos! It's only cloth. What are you scared of? That you might like it?" She teased unmercifully.
That was exactly what he was afraid of.
"It was just an errant thought, accidentally voiced, that's all."
Lea, who was bored and in no hurry to start her homework, suddenly found herself with a new and interesting game. "David Beckham wore a skirt."
"That was a sarong."
"Ahh, but you said a kilt was a skirt, so by that definition, a sarong is a skirt."
Thomas knew he had backed himself into a corner with this one.
"So, go on." She chided.
"Go on what?"
"Put the dress on silly, or would you rather I called it a sarong?"
He knew his sister too well and that this could go on all night and the next day. Sighing dramatically, he held up the dress. Like the one his sister wore, it buttoned up the front. Unlike the one wore by his sister, this one had all the buttons undone from the neckline to the waist. He slipped the hem over his head, raised his arms to feed them through the short sleeves, allowing the hem to fall down.
Lea burst out laughing.
"What's so funny?" His voice was indignant.
"You don't wear it over trousers and a T-shirt. Take them off and wear it properly."
"Fuck off!"
She laughed even harder. "You're biting!"
"I'M NOT!" He retorted, biting.
"You are."
"I'm n..." He gave up.
"Take off your T-shirt and trousers."
"Why?"
"Am I wearing shirt and trousers?"
"No."
"Well, there you go. Take them off."
He was starting to get annoyed now. This was getting out of hand, no longer funny.
Lea started to flap her elbows and make chicken noises.
"Oh for Pete's sake!" He stormed from the room, Leas laughter following in his wake.
In his room he slipped out of the dress and removed his T-shirt. He hesitated.
"What are you doing up there? Putting on makeup?"
He removed his trousers. It didn't feel right. He pulled a pair of shorts from a drawer and put them on. Slipping the dress over his head he did up the bottoms over his chest. He tried a few tentative steps around his room. It felt so weird having material flap around his kneecaps.
"You still alive up there?"
Thomas made his way back down the stairs, the hem of the dress floating about, the material catching between his legs with silky caresses.
On enetering the living room, he stopped in front of Lea, who studied him intently.
"Thomas?"
"WHAT?!" He snapped back irritably.
"I'd lose the football socks."
He looked down at the long socks in the colours of his favourite team. He wiggled his toes for a moment before bending over to pull the socks off.
Lea pinched her nose shut between thumb and forefinger while making gagging and retching noises before descending into hysterics.
"Very funny." He turned back to his chair and slumped down into its embrace.
Eventually Lea calmed down. She sat there and stared at Thomas, who found the scrutiny off putting.
"Thomas?"
"Yyeeessss"
"Are you wearing shorts?"
"Nope!" He retorted with utmost conviction.
"You telling the truth?"
"Yip"
"I think you are telling porkies. Prove it, lift your skirt."
He felt all his blood drain to his feet. "Okay, but only if you lift YOUR skirt first. To prove that you're not wearing shorts." He sat back in smug relief as Lea's blood seemed to flood to her head. She looked away, face beetroot red.
Thomas crossed his mental fingers and hoped she would let the matter drop.
She did.
However, his own mind refused to let the matter drop. He wondered what he would have done, had she stood and lifted the hem of her dress to her waist. The mental image of Lea stood in front of him, pants on display, was starting a rather embarrassing biological reaction within his own pants. He quickly realised that the impending hardness would be all too visible under the dress. The more he tried to think of something else, the worse the problem was becoming. He had to do something fast.
Suddenly standing, he made haste towards his bedroom. Safely inside, he stripped off the dress and changed back. The only trouble was that his erection was full blown and uncomfortable. He opened his door and chanced a quick peek too see that the coast was clear. It was, so he hurried to the toilet and locked the door behind him.
Pulling down trouser and underwear, his erection bounced free to the horizontal. Taking hold of his rigid member, he pulled back the foreskin and spat onto the bare head. The image of his sister was still strong in his mind. He imagined her slowly slipping out of her dress. He had never thought of her in this way before, yet the imagery was highly intoxicating. His hand pumped quickly up and down his shaft, as the mental Lea slowly allowed her dress to fall to the carpeted floor. Her hands roamed her body, her breasts, slid between her thighs then lasciviously beckoned him closer.
He knew from preliminary sensations that his impending orgasm was going to be a belter. It did not disappoint. As Lea enticed him closer to her almost naked form, muscles contracted and he almost cried aloud as his knees threatened to buckle and thick creamy jets of cum exploded forth, spraying over the tiles backing onto the sink and the mirror above.
Thomas could not believe how intense his orgasm had been. Not as intense as his first ever, but pretty damn close. Even more surprising to him, was that in his minds eye, his sister had only stripped as far as her underwear. A whole new avenue of masturbatory dreams had been opened up to him.
Ripping off a long length from the toilet roll, he started to mop up the long trails of cum sliding down the mirror, pooled in the soap holder and clattered all round the inside of the sink. The sodden mass of used toilet roll made a loud 'plop' as he dropped it into the porcelain throne. He flushed and watched the sodden mess swirl away.
Unlocking the door, he headed back to his room. His sisters dress lay discarded on the floor, only, now it had a different meaning in his life. He picked it up and made his way to her room. He opened the door and threw the dress onto her bed. Shutting the door again, he headed back downstairs.
Lea still lay slumped in the same position, her face had returned back to its slightly pale state in his absence.
"Awww, you took it off."
He dropped back into his seat. "Your dress is back on your bed."
She nodded "You looked quite cute you know. I..." She trailed off, suddenly unable to meet his gaze.
To a certain extent, that suited him happily, and no other words were said or looks cast in the others direction until their parents arrived home from work.
That night he could not get the image of his sister dancing provocatively out of his mind. She slowly, teasingly stripped; to stand in front in only bra and pants. Slowly removing her bra, cupping breasts that had mysteriously enlarged in a fashion only dreams allowed.
He sighed, rolled over and switched on his bedside light. He pulled out the roll of toilet paper from its hiding place and lowered his boxers. This would be the third time this night he had resorted to manual release. He seriously began to wonder if it was possible to wank yourself to death. The image of his tombstone flickered briefly into existence within his mind.
'Here lies Thomas Dray. Wanked himself to death, over dreams of his sister'
It was soon shoved aside by the image of his sister. Even in his dreams, she was demanding.
He erupted into a strategically placed wad of toilet roll as his sister rubbed a breast with one hand while the other was doing something hidden behind the material of her pants.
The relationship between the pair of them was remarkably restrained after the dress incident. Neither of them was willing to bring it back up. That did not stop Thomas's imagination, which seemed to get even more extreme with every passing day.
Just the previous night, he had dreamed of getting her pregnant, and then sleeping with both her and the child, with conveniently turned out to be female. Far from being abhorrent, the wrongness of the scenario fuelled his desire even more.
Whenever he saw a scantily clad girl on television or in magazine adverts, his mind would superimpose his sister's face upon that of the actress/model. It was proving to be quite a distraction. He also started to pay more attention to what Lea wore and how she wore it.
Even the teen magazines that she bought, turned out to be remarkably explicit and it was easier to imagine his sister in the pictures as the models were of similar age and stature, not yet graced with the womanly traits of pronounced breasts and wide hips.
It was his enjoyment of looking at the pictures that was to inadvertently become the catalyst to a more intimate relationship.
Bored, sitting watching complete drivel on the telly, he spied one of his sister's magazines that she had been in the process of reading. Temptation proved too much, he pulled it over and picked it up. He looked briefly at the contents page, his eye snagged by the title 'Are you wearing the correct sized bra?'. Intrigued, he looked for the page number and leafed his way there.
The article started off with some statistics, then went on to describe how a bra should fit properly. He scanned the article briefly; his attention was more on the female model that they were using to highlight various points. Due to her obvious young age, the shots were framed so that several intimate parts of her body were 'just' hidden or obscured from view by a bent or conveniently placed limb, even though the young model was wearing an extremely conservative matching bra and pants set.
Still, the photographer's efforts at modesty were no defence against a teenage male's imagination. He was surprised, but not complaining, at the obvious young age of the model. She looked nowhere near sixteen and appeared to be of similar age to his fourteen year old sister. So similar in fact, that all he saw was Leas face. Which he had to admit, was a good thing as his sister was better looking.
"A good read is it?"
Thomas quelled the urge to jump into the air in surprise, making an effort to look innocent instead, then realised it was pointless. He decided to brazen it out. "Did you know that eighty percent of women are wearing the wrong sized bra?"
Lea looked at him confused. "Are you on drugs?"
"That's next week's issue."
"Don't tell me, you can help me measure up properly?"
That thought had not occurred to Thomas and the more he considered it, the more it appealed to him. "Since you mention it, I'm more than willing to give you a hand. Or two" His gaze settled on her small, almost non-existent breasts and stayed there.
"Who said I was wearing one?"
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