Field of Dreams Ch. 01: A Sissy Fulfilment

Day 1: A most welcome goodbye

On a Sunday evening, Cecil Melton could hear an engine revving and see the taxi slowly rolling down the street. When it turned the corner, he exhaled, turned the lock in the door and smiled.

Melissa would be gone for two years now. He loved her, but was thrilled at the opportunity to be alone and explore himself, who he was and what he enjoyed the most. For two years Melissa would be studying the indigenous people of a village deep in the African jungle. The village was off the grid, but once a month, the first Sunday, she had half an hour on a satellite phone. She had only brought a small suitcase, and intended to buy new clothes when arriving in Nairobi.

That meant her whole wardrobe was available to Cecil, and he was keen to exploit that fact.

Cecil was 5 feet, 6 inches tall, quite small for a man. After years of road bicycling, he had a thin upper body and arms, but large thighs, calves and butt. His feet was small, and he often could save money by buying kids shoes instead of the adult sizes. He was actually five inches shorter than Melissa. When she was wearing heels, he looked like her son, not her husband and lover. Cecil compensated for the lack of height with the right size of the equipment between his legs.

All his life he had lived in the shadow of other women. With four elder sisters and a mother all taller and stronger than him, and with a dad who ran away when he was only four years old, sick and tired of the women, he was used to women. And especially used to women's clothing.

His four sisters eventually moved out, and it was just his mother and Cecil left in the house for a couple of years. The big house was becoming more empty, and Cecil was often alone at night. His mother either worked as a bartender or cleaner, or out trying to meet a new man. She didn't succeed very often, and seldom took someone home with her.

But Cecil succeeded. He had always felt a yearning and longing for wearing women's clothes. And when his mother wasn't home. he grabbed the chance every time.

With the memories of his mother's shoes, stockings, panties and dresses in his mind, he climbed the stairs and opened the door to their bedroom.

The room was dimly lit, and only a single ray of sunlight splintered the sun blinds. He had always secretly admired the pink color on the walls, which Melissa had fought through, and he stubbornly argued against, just to prove that he was a real man.

She had won, and now he loved being there. Just like a girl's bedroom. They had a fluffy carpet on the floor, which he knew would make it smooth moving around. He opened up the sliding doors in the wardrobe and took in the view. About one fifth of the wardrobe was his clothing. The rest was Melissa's. He could understand why she didn't bring any clothing to Africa, it was too much and too hard to choose.

To the left there were many levels of shoes. Most of them with high heels. Some of them boots, either regular, to the knee or overknees. Others were pumps, either with sharp stilettos or more of a big heel. They came in all colors as well. Then came the dresses and skirts. To the right side were the drawers, all neatly organized. Panties, bras, garters and stockings had a drawer each. The same for blouses and other tops. Trousers had their own section, while the biggest was reserved for the knitwear. Melissa was quite cold, and freezed easily. She had therefore had a huge stack of wool sweaters and cardigans. All in different patterns and with different neck types.

While pondering and thinking what to wear first, he heard the doorbell ringing. At last the package had arrived. This first thing was something Cecil had thought of for a long time, but never pulled the plug, to be honest.

He rushed down the stairs and greeted the delivery guy at the door. He accepted the brown package and rushed upstairs again. He wrapped open the package and could see it: A pink chastity cage, with the end shaped like a clit for him to enjoy himself, and a shiny butt plug in pinky steel. The end was a pink diamond. Perfect. It also came with a thin bracelet that connected the two of them. Cecil felt a rush of blood through his head and a shiver through his body. He slipped on a pink pair of panties and tucked in.

His journey had finally started.