A New Experience (Sample)

A New Experience

Chapter 1 - Caught

It all started on a cold winter afternoon, and David was stuck inside. He had originally planned to spend the day with his friends at the local skate park, but unfortunately the rain had cancelled the only thing he had to make this day eventful. Now, home alone, he had nothing to do except to find another activity to liven up his day and to end his boredom. His parents were away for the week and his sister was out with her friends. However as David had found out several years before, there was always one activity a boy could do wherever he was, and at the age of sixteen, he was well practised in this particular activity. He had a huge crush on a particular girl at school, and with the fact he was home alone, he made his way up to his room to satisfy his urges. But on his way to his room, he noticed out of the corner of his eye, a red flash. Turning properly, he realised what he had seen were the bright red panties sticking out of the top drawer in his sister’s bedroom. She was a couple of years older than him, and he knew she had a reputation of being a ‘wild one’. There was something about these panties that drew him in. suddenly a thought flashed into his head, he could take the panties and fantasise that they belonged to the girl from school. He took them into his room and shut the door, but just as he pulled down his trousers, he suddenly had the urge to try them on. As quick as a flash, a new fantasy crept into his head; what if the girl and her friends made him put them on? David dismissed this idea, until he realised that this was turning him on. More and more ideas began flowing into his head, making the fantasies become more and more intense. Before long he was fantasising about being completely dressed up as a girl, for the enjoyment of his crush and her friends. David looked at the clock and realised he still had a good couple of hours before his sister was due back. He raced into her room and threw open her wardrobe, in which he found a pink mini skirt, a pink top and a pair of black high heeled sandals. He then went to the same chest of drawers as he found the panties, and pulled out a pair of black tights and a red bra to match. Taking his new outfit to his room, he quickly began putting it all on. Before long he was dressed up, and admiring himself in the mirror. The more he bent over and struck the sexy poses, the more turned on he became. Soon he was incredibly close to the edge, and started to make his way to the bed to finally orgasm. However during his time in front of the mirror, David had lost track of time. Just as he sat down on the bed, he heard the front door open and footsteps coming up the stairs! Terror seeped into him as he knew he was trapped, especially as he remembered he hadn’t shut the doors of his sister’s wardrobe or drawers. Despite the terror, David was shocked to find that the feeling of being caught was another turn on of his. His climax was edging closer, effectively keeping him glued to his bed. He heard her footsteps stop outside her door, and then quickly turn towards his room before hearing a knock on his door. David didn’t dare move, not that he could anyway, but this tactic didn’t work, as the handle began to turn.

It was no use, just as his sister walked over the threshold, that was when the orgasm that was so long in the making arrived. The intensity of the fantasy which led David to this situation caused him to let out a soft but loud moan of satisfaction. He opened his eyes and found his sister standing over him, a look of both amusement and disgust on her face.

“Well, well, well, what do we have here? Looks like some little drag queen has been having fun ruining my clothes! As well as my underwear by the looks of it!”

David could feel tears building from the pure feeling of humiliation. Suddenly this fantasy which had turned him on so much had become a very harsh reality, and one that he was not enjoying in the slightest. He was barely able to string a sentence together.

“Julie, I’m sorry, please don’t tell anyone!”

“Oh just you wait! I’m gonna tell mum exactly what I found today and trust me I’m gonna make it a lot worse on you!”

David was not sure what she meant by that, but the fire in her eyes and the ice in her words seemed to make his blood run cold. Feeling sick in the pit of his stomach, David could only crawl into a ball on the bed as Julie left the room, closing the door on David’s tears of shame.