Debra Helen's Stories of Fiction (or are they?)
CAUGHT IN THE ACT
Stillness settled over the house as the sound of the shutting door dissipated through the hallway. He looked out of the window as his mother and older sister walked down the driveway and turned right towards the town center and the shops. He’d thought about this opportunity many times over the previous few months but had never had the nerve to carry through with his plan. In his early teenage years and still very much a novice with such issues, he wasn’t sure what the ramifications of his actions might be, but he knew instinctively that he couldn’t put off the moment any longer. If he was to understand himself and come to terms with his dreams and desires, he needed to take the next step.
He walked quickly upstairs to his sisters’ bedroom and selected clothing from several places. First, he chose black stockings and a matching garter belt, along with panties and a creamy pink bra, slightly padded. Next, he selected a full-length slip and a black blouse, followed by a red suede skirt and a pair of high-heeled shoes. He wasn’t sure that he’d fit into the shoes, but he guessed his feet were still fairly close to his older sister’s shoe size. He went to the bathroom and stripped naked. He stepped into the panties and then rolled the black stockings up his legs, fastening the tops to the garter belt that he secured around his waist. Then he slipped his arms through the straps of the bra and secured the clasp at the back. He rolled up several lengths of tissue paper and stuffed each bra cup until he had what could be considered a reasonable bust line. He realized that he was having trouble keeping himself secure in the panties, and when he dropped the slip over his head and down to caress his body, all control was lost.
He burst out of the panties, fully erect, and erupted into an orgasm so strong that he fell to his knees and doubled over, trying desperately to contain the liquid that sprayed out of him and to prevent any staining of his sister’s clothing. Shaking with the force of the experience, he got back to his feet and wiped away the liquid, making sure that no sign of the semen could be seen on the panties, stockings, or slip. Despite the sexual release, he knew that he had to continue, because he wanted to dress as a girl, to feel what it would be like as a girl, and to try and understand why it felt so good to dress up in female clothing.
After collecting himself, he continued dressing, putting on the blouse and then pulling the suede skirt up over his legs to his waist and securing the zipper. The heels were a tight squeeze but they fit more or less. He arranged his hair in the feminine style – it was quite long, as the style of the period, and curly, so he didn’t have to do much work to make it look passably feminine. Next, he went to his mother’s room, sat down at her makeup table, and commenced to transform his face – rouge, powder, lipstick, eye shadow, eye pencil, and more powder. He found some jewelry and set about accenting the outfit with a pendant, some rings, and wrist bangles. Finally satisfied that he’d done all he could to transform himself into a female visually, he walked back to his sisters’ bedroom, wobbly during the first few steps but more confident with each stride, and positioned himself in front of the mirror. A pretty young girl looked back at him, and he burst into tears. “Oh my god,” he cried, “I really look like a girl and I feel so pretty and feminine.” He sat down on the edge of his younger sister’s bed, gazing into the mirror at his female image, and cried tears of joy. He became so engrossed in his transformation and how he felt that he didn’t hear the front door open and close, or the footsteps on the staircase. He just stared into the mirror and continued sobbing with happiness.
The question coming from the door behind him startled him, then stunned him, as he jumped up and turned to see his mother staring at him with a puzzled look on her face. “Why are you crying so loudly and what are you doing dressed up in your sister’s clothes?” His knees buckled and he sank to the bed unable to think of a response. He looked at his mother and shrugged his shoulders. “I….I…..I wanted to see what it felt like to dress up as a girl. I wanted to be pretty.” Tears flooded down his face again as he saw his mother’s disapproving look. “Are you homosexual?” she asked sternly as he smoothed his hands over the skirt and tried to regain some of his lost composure. “No, I’m not. I just wanted to dress up in pretty clothes like a girl. It just feels good.”
His mother looked him up and down for a few minutes, sighed, and shook her head slowly. “Well, the first thing you’d better do is to get your own clothes because you can’t wear your sister’s, or mine for that matter. And you’d better shave your legs if you’re going to wear stockings, and you really need to put makeup on a little more carefully and with less of a trowel effect. Less is more, especially with rouge and lipstick.” She walked over to him and stood him up straight. “Turn around, let’s look at you. What are you going to call yourself? You can’t have a boy’s name if you’re pretending to be a girl!” He wiped tears away from his cheeks and looked at his feminine image in the mirror. “My name is Debra,” she said softly as she straightened her skirt and smoothed her blouse. Her mother came closer again and embraced her with a hug. “Well, Debra,” replied her mother with a sigh, “we have some talking to do and some issues to address if we’re going to get through this.”
Debra started to cry again and looked at her mother with some anguish. “I didn’t mean any harm, Mum. I just wanted to be a girl and to dress up in pretty clothes and to see what it felt like to wear high heels and put on makeup, and, and…..” Her mother stroked her hair and kissed her forehead. “That’s OK, Debra. You have about two hours to enjoy being a girl before I return from town with your sisters. I suggest that you not be here when we return, and make sure you tidy up after yourself.” She kissed Debra on the forehead again and walked out of the room and down the stairs, picking up an envelope from the hallway table before leaving the house. Debra’s knees gave way again and the tears flowed as the tension of the encounter flowed quickly away from her. She dabbed her eyes dry and looked in the mirror, spinning slowly around on one heel. “Hello, Debra,” she said to herself. “Let’s enjoy being a girl, even if it’s only for a couple of hours.”
The next story of Debra Helen's fiction will be posted soon.
Last updated on 4/18/08
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