Tim's Dream
by Sarah Smith
In the bright morning sunshine Tim walked briskly along the street. His long chestnut brown hair shone in the sunlight and bounced with every step. People looked up and took in the sight of the gorgeous figure walking down that street. Tim caught his reflection in a shop window; it was easy to see why he was getting so many admiring looks. Under a white cotton blouse, slightly transparent in the sun, breasts jutted out, tightly held in a white lacy bra. His brown pleated skirt swished sexily around his thighs, it finished way above the knee and showed off his drop dead gorgeous legs to perfection. The long, slim and beautifully shaped legs were encased in sheer tan hold-up stockings and the 3 inch high heels gave his slim ankle and calf muscles a sexy shape. He continued around the corner to the park all the time smiling to himself with the knowledge that only he knew what was under the skirt, tucked inside white silk knickers. Sitting on a park bench he reached into his handbag and took out a small compact and checked his make up. It must have been the 10th time that morning but the truth was he just wanted to look at his pretty made up face. As usual it was perfect and he fluttered his long eyelashes at the pretty girl in the reflection. Tim could not resist touching up his lipstick even thought it did not need doing. Finally putting the compact away he sat back and smooth out his skirt around his thighs. He crossed his legs and enjoyed the gentle wisp of his stockinged legs rubbing together. The skirt rode up showing the top of a stocking, Tim gently stroked his thigh from knee to the top of the stocking and his glossy lips trembled slightly at the sexy feeling of touching the nylon clad leg. Then, he felt an almighty rush, his head was spinning and then –too late- he realised he was coming.
Tim woke in his bed, the tell tale wetness in his boxers informed him it was another of those dreams he kept having. Fuck! It had felt so real this time.
He stuffed the soggy underwear in the dirty linen basket, making a mental note to put them in the washing machine before his mother got there first. He was glad that today was today because his sister was coming home from university. She was three years older than Tim and seemed have got all the good looks out of the pair of siblings. Before she went away they had constantly bickered and quarrelled like most brothers and sisters, but afterwards he had started to miss her being around and before the first term was over he was actually glad to see her back. During her stays at home during the vacations they had become a lot closer.
Tim made his way down the stairs to breakfast. Although he had showered and changed he still looked unkempt. His longish brown hair always seemed to be untidy and his clothes hung on his slim physique.
"Morning!" he called to his mother.
"Morning?" she chided back to him "I think you'll find young man that morning has been and gone".
"Yeah, yeah, I'll just get some breakfast" he yawned back.
"Breakfast!" his mother decided there was no use pursuing this line of conversation and changed the subject "Can you come shopping with me please? I know you hate it but I want to get something special in for Kate's first night back so I'll need your big strong muscles. After that we'll meet Kate at the station, OK?"
It was all OK apart from the big strong muscles crack.
As they drove to the supermarket Tim noticed that the bright sunny day was just like in his dream that day. It was still vivid in his mind, it felt like he really was wearing all those lovely things. Occasionally his eyes would lock onto a woman on the street. In a flash he would take in everything she was wearing, from her hairstyle and make-up to her shoes. In the supermarket he was given the job of pushing the trolley while his mother fussed over the list and collected the things.
"I forgot shampoo. Be a sweetheart and go back and get the usual stuff"
Tim shuffled off, glad to get away for a bit, and headed off into the vast supermarket. Within a minute he had found the shampoo and selected a family sized bottle. He looked at the vast range for all different types of hair, around were adverts with models showing off their beautiful shiny hair. He kept wondering along the aisles hardly noticing where he was going until he found himself looking a shop mannequin, more to the point, he was transfixed by the gorgeous white lacy lingerie it was modelling. The underwear looked fantastic and he wanted it badly, the tiny bra, the skimpy knickers, the suspenders and the fine denier stockings stretched over his legs. He felt himself started to feel warm tore his eyes away and tried to go and find his mother. It seemed that everywhere there was lots of wonderful feminine underwear in every direction. He saw the packets of tights and stockings being displayed. Maybe he could slip one into his pocket? Who would know? What if he was caught? The thought of the humiliation brought him back to his senses and he quickly left, but not before noticing a few pairs of eyes on him. A few women must have seen him browsing and they gave little smirks as he sped off, blushing a deep red.
It was great to have Kate back home for the holidays. The house was full again and Tim enjoyed having his big sister back. One Saturday afternoon Tim was in his room looking at the women's underwear catalogue as usual when Kate came back from a shopping expedition in town. He went to join her in her room.
"Hi! Get anything nice?" he asked
"Yeah, a fantastic new dress, really sexy, some shoes and accessories"
She held up a gorgeous black dress against herself.
"it looks great, is it for anything special?" Tim said.
"Not really, just my little black number. I reckon the hem could come up about an inch to show off my legs. You can help if you like."
"OK" agreed Tim "but I'm not that great with a sewing needle."
"Oh, you won't need to sew anything, I'll do the sewing" she walked over to her younger brother and held the dress against him "I want you to wear it while I take up the hem."
He gulped. This was something he wanted more than anything else. He realised his cheeks here burning a deep crimson. He wanted to pretend to resist but how could he deny it?
"I promise I won't tell a soul" Kate added "you'll be doing me a big favour and it will be our secret."
A few minutes later he was in just his underwear stepping into the tight dress. Kate zipped up the back and pulled at the material until it fit Tim's slim body perfectly. He loved the feeling of the fine black see through nylon top clinging to his flat chest and arms. The waist clung tightly and then followed the contours of his body down to the tops of his thighs and then spread out. Stopping well above the knee, it showed plenty of leg. Next he put on some high heeled shoes so that Kate could see how it would rest when she wore it. Tim stood perfectly still as his sister went around pinning up the hem. After a while she stepped back to check her work.
"You know, you look pretty good in my dress. You've got a great pair of legs too, a lot of girls would be jealous."
"Thanks" Tim beamed back at her "it feels nice, I really like it." He had not meant to offer the last bit of information.
"Really!" said Kate "Have you tried my clothes before?"
"No, honestly I haven't, I promise" There was a slight panic in his voice.
"It's ok. I don't mind. Tell you what, as a reward for helping me why don't we dress you up as a girl for the day? It will be fun."
This must be a dream.
"Ok, I'd love to, thanks." It was really going to happen.
Tim emerged from the bathroom fresh and clean, his hair wrapped in a towel, legs and armpits smooth, everything ready to go. When he entered his sister's room he saw she had laid out some clothes for him. She smiled and sat him down by the dressing table and set to work on his damp hair. She dried it and gave it some style by adding a few hair clips to sweep his long hair behind his ear.
"You've got lovely smooth skin so you won't need that much foundation" said Kate as she smoothed the creamy foundation around his face. Then she added some blusher, eye-shadow and mascara on his long eyelashes. Finally came the lip gloss, a deep red that would go with the outfit.
Tim looked in the mirror and saw a very attractive girl looking back at him. She did not really resemble the boy from a few moments before.
"I think we'll call you Tina." Kate announced. That was ok with Tina.
Kate turned her back while Tina got into her new pair of knickers and then helped with the bra. They stuffed the bra with a couple of pairs of tights to create breasts.
"Now you are really starting to shape up" Kate said as she handed a pair of new tights to Tina. Tina felt herself blush. They were like the tights she saw in the shop. Black, fine and very sheer. Tina rolled up the legs of the tights as she had seen done before and dipped her toe into the sheer nylon and gently pulled up the first leg to the knees and then the other. She loved the feeling of the fine denier mesh clinging to every curve of her legs. Then she pulled them up to her waist and reached down to her foot and gently drew her hands along each leg, caressing the gorgeous feel of the nylon on her legs from her slim ankles to her shapely calves and up to her slim thighs. Kate watched in amazement at the sight of her younger brother stroking his long legs. He looked so feminine, so comfortable, natural; it was becoming difficult to think of him as a he.
Tina was happy to see that it was Kate's new dress she was getting to wear. Kate zipped her up and then Tina put on the new shoes. They were black of course, 3 ˝ inch heel and a sexy little ankle strap. Gently she tottered about the bedroom admiring herself in the large mirror. The shoes made her legs look even longer and sexier.
"I feel I'm being outdone here by my own little brother, or maybe I should say sister?" said Kate "I think I'll get dressed up too and then we'll have a girls night in."
Tina sat in the armchair and watched her sister get ready. As she crossed her long legs she enjoyed the feeling and wispy sound of the fine nylon encasing her legs. Even when she closed her eyes she still felt the glorious feeling of being encased in femininity from made up face to nylon encased feet. It was just like her dreams, only it was better because this time it was real.
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