Disclaimer. This story is set in the UK where the age of sexual consent is 16. If is not acceptable in other countries then please do not read as I will take no responsibility for others actions.
Prologue
Terry for all exterior appearances was a normal 16 year old. Though he kept his body to a minimum but as he was on the cycle team this allowed him to shave is body hair off without question. This also allowed him to maintain a slim build. And with the time being the mid 90's he had grown his hair in to a ponytail that reached below his shoulders.
Yes for all appearances Terry looked like a dedicated athlete. But what people did not know this was all a cover for his secret. Since the age of 13 Terry had been borrowing his mother and sisters clothes. It started with just underwear but over the years his desire to dress and progressed to full transformation in to Teri. At wearing his sister's latest fashions he could easily pass as a really 16-year-old girl.
His sister Samantha or Sam was 2 years older than Terry and was heading off to university. This allowed her to have a big clear out of her stuff. She put all her unwanted clothes in to black bin sacks so their mother could drop them off at the charity shop.
At 16 his parents felt Terry was old enough to stay on his own for the couple of days they would be away helping Sam settle in to her new halls of residence some 300 miles away.
15 minutes after they left Terry had felt he had waited long enough for them not to come back because they forgot something. Terry brought all the black sacks in from the garage in to the living room and opened each one in turn to look through this bounty.
He controlled himself not to take the lot but he helped himself to several bras and panties, and very naughty lacy corset with suspender straps she must have worn for her ex boyfriend Derek whilst they fucked. He noted that he would need to head to town and get some stockings to co with it.
Then he found it and his heart pound with desire. It was Sam's school uniform. Terry had not seen this in nearly two years since his sister went into the 6th form where uniform was no longer required.
He had tried it on back then but it was too small for him, but now he it should fit perfectly.
The problem was if had been in the loft for 2 years and was not smelling to great so Terry decided to take all the clothes from the attic and wash them whilst he heads to town for some feminine supplies.
He slipped on a nice black lacy thong and covered it with his boxers and jeans, grabbed his keys and wallet and was out the door. He hoped the washer /dryer would have his treasure ready for his return.
In town he made his way from store to store buying what he needed. He had made a shopping list so it looked as if he had been sent on an errand to purchase the items. Since he need food as well it was not too difficult to use the shopping list as a cover to buy stockings, make up and hair spray.
The bus home could not move fast enough for Terry as his trebling hand put the key in the lock of the house. He checked the washing and it had finished. He set up the ironing board and pressed the school blouse, tie, blazer and grey box pleat skirt.
He ran to the shower and washed himself in the fragrant soap he purchased and gave his smooth body another going over with the razor.
He was ready for the transformation to begin. With the towel wrapped around his torso and a smaller one as a turban over his hair he sat down at his sisters not vacant vanity unit and layer out his purchases from town.
Since make up was no long difficult to him he expertly applied eye shadow and mascara to his eyes, foundation and blush to his cheeks. And a nice light pink lipstick to his lips, and he was done. God he thought he could pass for his sister in a darker room. He took the towel off his head and blow dried it and used his hot iron he purchased for himself when he started to grow his hair out. With his hair curly and fluffed up with two sexy bangs framing him face it was time to get dressed.
He decided to be naughty and put on the lacy corset and clipped his new seemed stockings to the clips. Next was the matching thong as he tucked his cock back to leave a smooth front. He slipped Sam's school blouse over his arms and loved the feel of the clean smooth cotton over his lacy bodice.
He buttoned up the blouse to the collar, long since expert in the reversed buttons on female garments. He slipped the grey skirt on and before it was just above his knee the last time he wore it now barely covered his ass and showed off his stocking tops. Next was her tie, though identical to his own he wanted to wear hers and lifted the buttoned collar and threaded the tie around his neck making sure it was evened out and tied it in a perfect Windsor knot. He was pleased that the V of the tie rested on the waistband of his skirt. He smoothed the collar back down and slipped the blazer on pulling his hair out of the neck and over his shoulders as he had seen main girls in his school do when they put their blazers back on during the summer when they were allowed to take them off in class.
Terry had gone. Terri now stood in front of the roof to floor mirror doors of his parent's bedroom wardrobe. She made herself a little dinner and watched the soaps on television. Since she only had her dirty crockery she decided to wash it up by hand rather than use the dishwasher. She loved slipping the blazer off and unbuttoning her cuffs to roll her sleeves up. When the dinner stuff had been put away and her uniform was fully back on she went to the fridge and helped herself to a glass of red wine from the wine box her parents kept in there.
At 9.30 curled up on the sofa she nursed her wine watching TV and her mind drifted to the boys in her year she fancied. Strange that as Terry only girls entered his mind when he fantasised about sex but as Terri for the first time it was boys that now dominated her thoughts. She knew all about sex from school and the few porno films she managed to see at his friend's house over the years. So her thoughts turned to giving them blowjobs and as there was a guy in his year that was obviously gay and bulled about taking it up the ass. Her mind turned to one guy in particular Kevin Harris.
She helped herself to a small tumbler of scotch with a little ice. This was the hardest drink she had ever tried and soon she was very tipsy. She followed it up with a small measure of gin. Her plan was to take a little from each to avoid detection.
Now buzzing on the booze the television was soon forgotten as her mind turned back to Kevin. He also was in his school uniform and pushing her to her knees as she reached out and unbuckled his belt and opened his grey school trousers and eased them down his legs. She rubbed his cock through his boxers and slowly pulled them down freeing the cock she had seen so many times in the showers.
She took the last swig from her drink and her hand was under her skirt rubbing her own cock.
In her fantasy she had kissed and engulfed Kevin's cock into her throat. With left hand she licked her finger and instinctively pushed it in to her boy pussy. She never did this before but she loved it so much it was soon joined by 2 more fingers as she finger fucked her self. Her other hand was busy fisting her cock. In her mind Kevin had pulled her off his cock and bent her over the desk and flipped her short skirt up and lifted the thong from her ass crack and rubbed his pre-cum covered dick over her waiting boy pussy. After a minute of teasing her hole he pushed all the way in slapping his balls on her ass.
Her finger pumped hard and fast as she wished it was Kevin's cock that was fucking her like the slut she had released from within her. In her fantasy Kevin slapped her ass as he pounded her for all he was worth. Kevin gave out an all mighty scream and dumped him load in her pussy. Terri's fisted Cock erupted under her skirt with an incredible orgasm.
It took Terri a few moments to come down from the best orgasm of her life. She pulled her fingers from her pussy and the other covered in her spunk. Still buzzing she liked her fingers clean.
She like the taste and reached under her skirt to retrieve as much cum as she could. She ate the lot. Looking up it was 10.30 and from the drink and fantasy she was spent.
She washed her hands and noted to clean her ass out better next time and there was shit on her fingers. She slipped the skirt off and with her thong put them on to wash and went up stairs to her room. She felt a little reluctant to break the knot of the tie but she needed to sleep. She hung the rest of the uniform up in her wardrobe and headed to bathroom. She hopped into the shower and cleaned her face and washed the hairstyle out of her hair and when she stepped from the shower Terry was back.
Since he was all only he decided e could remain as Terri and brushed his hair out put on a white bra and stuffed it and pulled on the white baby doll nightie he had found.
He crawled into bed and feel asleep to the image of Kevin. She gave a little schoolgirl giggle and fell into a deep sleep.
By Brenda Chaplin
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Brendachaplin2000@yahoo.co.uk