Beginnings and Endings                          by: Ray Kitten

 

Peter shifted the heavy garbage bag to the center of his back as it had once again managed to slip down towards his armpit. Once the traffic signal changed he trudged again onward, still deep in thought as he plodded right in front of a car that was trying to navigate a sharp left turn. The driver forced his brakes and narrowly avoided running Peter down, as he quick dashed to the sidewalk the driver leaned out the window to holler words which Peter was too polite to repeat.

The physical and mental weight of the bag was oppressive on his back as Peter reached a new block, marching onward yet he had not gone a dozen steps when his train of thought drifted. He stared down at his shoes as he walked, he hated them, they were black, ugly bricks of imitation leather, thick and clunky. He gave a sigh as he realized that he had better get used to them however, and perhaps in time, learn to like them.

Here he was, less than two weeks into his engagement, expecting that his new fiancee would be the foremost thing on his mind. But as he carried the trash bag block after endless block, he found it difficult to get his mind off other things, such as the contents of this bag and it’s final destination. In his mind’s eye he could see many of the items within and recall the significance of each one.

First of all there was the dress. But this was not just any dress, this was the very first dress that Peter had ever worn. It had belonged to his older sister Pam, and in his mind it was one of the most beautiful things he had ever seen. At 17, Pam was 3 years older than him. He had always been a runt; and at a time when most boys where beginning their growth spurts, he was still a couple inches shorter than her. Peter had gone into the bags of clothing being given away to Goodwill to retrieve a favorite T-shirt which his mother had thrown in because it was torn, but the moment his hand landed on the dress he was mesmerized, and completely forgot about the shirt. It was beautiful, black velvet with a knee length flared skirt, and a big floppy bow at the back with a V neckline and those huge puffed up sleeves. It was so wonderfully soft and feminine. It had once upon a time been Pam’s favorite party dress, but had decided to get rid of it because she felt it was too childish what with the huge bow and balloon sleeves. He had taken it back up to his room, at first intending just to look at it while imagining some of the girls he knew wearing the dress. However, after a while Peter started thinking about what it would be like actually to see someone in the dress, Yet he couldn’t think of any girl he knew that would try it on, and wouldn’t think he was some sort of freak if she found out he had kept one of his sister’s dresses in his room. Somewhere along the line the idea came to him to try the dress on himself. At least then he would know how it hung on a body, and how the sleeves puffed out when they actually had arms in them. However the idea seemed so odd and even a little gay, so he brushed it off, but as time passed it continued to come back as the only opportunity to see someone actually wearing the treasured dress. Finally, after almost a month of debating, he came to the only decision he could. He put on the dress himself. He had trouble with the zipper, so he ended up threading a string through the zipper tab and pulling it up with that. He turned and looked at himself in a mirror. Somehow it didn’t hang right, it was still a gorgeous dress but he simply didn’t do it justice. As he stood there studying the boy in a dress that returned his analytical eye, it occurred to him, girls had breasts. A quick trip to Pam’s room for a bra, and a half dozen water balloons later so did he, who would have thought it was so hard to make two water balloons the same size. With his new girlish figure he looked again in the mirror with just a touch of awe. If he squinted just right it could be a fairly boyish girl wearing this dress. As he turned to examine himself the skirt brushed his legs teasingly, he hadn’t been prepared for how good that would feel. Right then and there he knew that he would be wearing dresses again, and often.

The next item that came to mind, as Peter somberly made his way deeper into the heart of the city, was a deep blue full length nightie which he had also taken without permission, not that he would ever have dared ask anyway. It had full length sleeves and a scoop neckline which was covered over in flower patterned lace, as was the whole bodice. The skirt of the nightie was slightly flared and sank to his knees. It had been his favorite nightie, even over ones that he had acquired both before and after it. He took that item from Pam’s stock of clothing which she had left behind when she went off to university, to study psychology of all things. She was now practicing in the big city. Too bad they were forbidden to accept family members as patients. Perhaps she could have helped him make sense of his desires to wear women’s clothing. No matter now, Peter sighed to himself, still lost in thought still.

He glanced around him taking stock of where he was, seeing that he had only nine more blocks till he reached his destination. Sighing once more, he fixed his gaze yet again upon his ugly, mannish shoes, they reminded him of another item within the bag, and it’s accompanying outfit. There was such a contrast between them.

In high school, he had allowed himself to enter into a bet which resulted in his having to attend the Halloween dance dressed as a girl. It had been rather easy to manipulate one of the macho jerks from the basketball team, into a wager as to who would make a better looking girl; the judging would take place at the dance and an independent panel was selected by both of them. The looser would get stuck with the bills for both outfits, so both Peter and his unknowing mark Derek Schnider, went all out on price for their outfits. Peter purchased a nurse’s costume from a novelty store, it was the super short type that a real nurse would never even dream of wearing, but it was cute none-the-less. After that he bought a pair of white thigh gripping patterned stockings, with a matching bra and panty set. That had been the first time he had ever bought clothing without pretending to be gift shopping for his mother, sister, or girlfriend. Then, Peter had gone to the shoe section and spent hours trying on every pair of white heels he could find. He eventually located the shoes of his dreams, they were white, and would match the costume. They had a 3 inch stiletto heel, but the most beautiful feature of these shoes were the cut out sides which where also windowed in patterned lace. Over $100 worth of clothing for free, he had giggling fits about that for a long time afterwards.

There were so many other memories in the bag, one of the most painful memories was symbolized by a sleek black cocktail dress. It was smooth satin, with a low cut back and a collar style neck that left the shoulders and arms bare. It flowed down to his ankles, with a slit up one side showing a lot of leg, all the way up to his knee. When he wore that dress it seemed to flow like liquid onyx as he moved, and clung to his body, outlining the very feminine shape that he had been fortunate to posses, in particular highlighting his bottom. The dress had been a gift from the one and only girl he had dated in the past. After almost a year together he felt that things between them were serious enough for him to tell her about his dressing. She had been a little unsure of it at first but agreed to test the waters slowly. One night she asked Peter to come over to her home, which is when she gave him the dress. That night they both got all dressed up in their formals, and she had helped him with his make-up something, which despite years of occasional practice, he still couldn’t quite manage to do well as easily as real girls. Once they were ready they sat down to an absolutely wonderful candlelight dinner, delivered by a fancy restaurant.

Afterwards they shared a bottle of wine in the dimly lighted living room, dancing close together for hours. That had been one of the most wonderful evenings in Peter’s life. Unfortunately he later learned that the evening had been a last ditch effort on his girlfriends part to come to terms with his tendencies, and she later told him it had unfortunately failed, explaining "I just feel too much like a lesbian."

The next item which came to his mind was a cute little outfit he bought shortly after he turned 21. It was a light blue miniskirt with a matching tank top, which he had later taken rhinestones and set them in the shirt to spell out the words "Sissy Boy". He had worn this outfit the first time he ever went out to the city’s only gay bar, "Bifrost". In the entrance way to the bar was a bridge painted in a rainbow pattern, and just beyond that was a small pamphlet on the wall explaining the name. Turns out the name of the bar was the name of the rainbow bridge into the land of the gods in Norse Mythology. He had debated for a long time the virtues of going there against the risk of someone seeing him. The main comforting thought was that anyone he saw there was likely to know what it was like to have someone judge them for what they were. He was sure that even if anyone he did meet someone who he knew they wouldn’t hassle him about what he was. Besides, he was dressing like a girl on a more and more regular basis ever since he had moved out of his parents house into his own apartment, and he had to wonder whether his feminine desires went deeper. He still had faced the problem of how to get to the bar though, he had no car of his own, and either walking or the bus, would have been far too public. The same problem would have arisen from taking a taxi. He had eventually convinced his parents to loan him the car, telling them he had to run some errands. He had sat in the parking lot for half an hour, too nervous to go in, but once he was inside, the flashing lights and pounding music of the dance floor soon combined with his first taste of alcohol to make his head feel like a helium balloon. But even in his relaxed state of mind Peter couldn’t bring himself to go out onto the dance floor. He just sat in the darkest corner he could find, drank and watched all the people around him chatting and dancing and enjoying themselves. After a few glasses of beer he found himself making a rather hurried trip to the bathroom to relieve his bladder. He failed to notice the lack of urinals as he walked in and took the only unoccupied stall out of three. Hiking his skirt up he did his business while the two other doors opened. When he was done and stepped out he was shocked to find two women checking their make-up at the mirrors, at this point it dawned on him that this was in fact the ladies room, and despite his clothing, he was sure that he shouldn’t be in there. Seeing no less embarrassing alternatives, he walked up to the mirror, opened his purse and started checking his make-up right along side them. When he looked in the mirror he blushed at what he saw. It wasn’t a man looking back at him, but it wasn’t a woman. It was a quite attractive, perhaps slightly over made-up, sissy boy, obviously male but feminine enough to not look out of place in the clothing he was wearing. The two women were very tolerant it turned out, one of them even offering "Chantelle", as he was now calling himself when dolled up, a spritz of her perfume. When they left the bathroom Peter tried to retreat to his corner again but the girls would have none of that. They insisted she come and sit with them at their table, less than 10 feet from the dance floor. At first Peter was self conscious about his very open location but within several minutes, the three of them were chatting away like age old girlfriends, the rest of the bar forgotten, all the while the girls referring to him by his female name. As Chantelle sat there in a dazed cloud of liquor, excitement, and the feminine scents of make-up and perfume, a strapping young gentleman approached and asked him to dance. After a whirlwind introduction on the dance floor, they were soon heading back to his two story townhouse for a bottle of wine on the balcony of the master bedroom, and then back inside. The culmination of that night was a complete and total disaster, and left Peter with the firm realization that Chantelle was a lesbian.

Fortunately, some good did come of that evening, for one thing Peter knew for certain that the desire to dress, and even to some degree act like a woman, did not necessarily reflect the desire to be with a man sexually. And the girls he met at the bar, Margery and Toni, ended up becoming two of his closest friends. He later found out they were a couple. The three of them had even contemplated a threesome with Chantelle at one point but they decided that might make their relationship a bit awkward and so they simply remained close friends.

Another treasure of the bag was a fun, flirty party dress, but this one was a bit more mature than the first. It was black with a soft raised rose pattern on it. It was short only coming to his thighs, and had a sexy, low cut, off the shoulder look that required a strapless bra, which fortunately, Peter had purchased after Chantelle had acquired a number of wide shouldered or off the shoulder dresses. This dress was special; it had been a birthday present from Margery, and Toni. They had also had given him a beautiful sapphire necklace to wear with the dress. The necklace was still at his house; real women loved jewelry like that, and his new fiancee would be no different.

Shortly after that birthday Peter had made an appointment for a make-over at an actual salon, although he planned on neither perm or colour, he had scheduled hairstyling, make-up, manicure, and then a photo session. He had gone as far as taking the bus out to the salon, with a garment bag full of his favorite outfits, however, when the bus arrived, he found he couldn’t bring himself to get off at the appropriate stop. Going to a gay bar was one thing, going into a salon filled with real women, normal people who judged, and hated was an entirely different matter. So instead, he merely stayed put and took the bus home. As he approached home he started to feel his confidence returning, and his desire to see himself as beautiful as he could be grew stronger. And so when the bus reached his home stop he stayed put riding back to the stop near the salon.

In the half hour drive between points his mind worked and his confidence wavered again. First off, what if the people at the Salon laughed at him? What if they laughed and told him to get out? Or worse yet, what if they couldn’t do it? What if they gave him the works and he still didn’t look like a woman? What if he came out looking like a joke? He couldn’t stand the idea of that happening. Or, what if everything turned out okay, he looked good, still like himself but a female version himself, and what if someone later found the pictures? What if someone at the Salon recognized him? What if they told others that he had been there and why? Then he would have guys coming after him to try and injure him or worse. Oh there were just too many ways this could go wrong and not nearly enough good. By the time they reached the Salon again, the idea of getting off the bus had Peter a nervous wreck.

So he stayed put.

He rode the bus home and this time finally got off, leaving his appointment unfulfilled.

The rest of the bag was filled with less significant clothing, a multitude of skirts, blouses dresses, feminine style pants and shorts. Bras, slips, his garter belt. The panty briefs, bikini’s, and thongs were already elsewhere, in another bag. Oh wonderful smooth, silky panties, with their sexy lace, and those erotic little bows. And the thongs, with that naughty little piece of material slid up between your cheeks, teasing you by rubbing your anus all day, something which despite his lack of interest in men, Peter still found very arousing. He would certainly miss those.

"Well," Peter said to himself. It looked as though he had finished his contemplating and mental checklist just in time. In the distance he could see looming, two blocks away, the destination of this bag; the bag containing every scrap of clothing Chantelle owned. The bright blue of the sign sporting a huge lowercase g looking very much like 2/3 of a smiley face, the Goodwill. That which comes from the sea shall one day return to it.

He reminded himself this was for the best, it was in the interests of his long term happiness with Sheila. They had met at the restaurant where they were both servers and after working together for several months had arranged to go see a movie with three of the other servers. But circumstances intervened and all three canceled on them at the last minute leaving Peter and Sheila alone to watch one of the most romantic movies of the year. Somewhere during the movie Peter reached over and placed his hand ontop of hers, and by the time either of them realized it, she had taken his hand in her own. So they sat there through the movie, holding hands, neither of them really knowing the other but both caught up in the drama of the love affair on the screen. That night they both laughed nervously about the incident while sitting in her car outside his apartment, but they could still feel the magic of that moment, teasingly about them, tempting them to give in to the urge and kiss. But they both resisted, and after a promise to see if they still wanted to see more of each other the next day, Sheila drove off leaving Peter on cloud nine as he walked up the stairs to his apartment. That night he had slept in his favorite blue nightie, and his head swam with the memory of Sheila and the feeling of holding her hand in his own. He hadn’t had anything like it since his previous girlfriend had broken it off with him. It took him many long hours before he was finally able to quiet his mind enough that sleep was able to claim his weary body. And while his body rested the next day found his mind equally groggy and fluff coated as when he had gone to bed. Everything still had a rosy glow as he practically danced around his home getting ready for work. When he got to work Sheila told him that she was still thinking of the night before.

"It was one of the most romantic nights of my entire life, and I don’t really know why, but I feel comfortable with you. Something about it just feels right," she told him.

They agreed to continue dating and within a year and a half Peter had asked Sheila to marry him. His first plan was to keep Chantelle a secret from Sheila, but as time went on that idea lost it’s appeal as his conscience nibbled away at him, and he heard story after story on the Internet of men, just like him, who had tried to do the same and when their wives found out, don’t fool yourself they always do, it almost always ended in divorce. Then Peter’s plan was to tell her about his feminine Alter-ego, however he was continually haunted by flashbacks of his previous relationship, could he risk loosing another sweet, caring, flesh and blood girl, just to hold onto a false one? It seemed he had to choose, Sheila or Chantelle. It wasn’t an easy decision but in the end he realized it wasn’t possible to go to sleep and hold Chantelle in his arms, he couldn’t kiss her good morning or feel her hands massaging his shoulders when he was upset. She wasn’t fully there for him, he could see her, and feel her inside him, but that was all, and in the end he wasn’t sure that was enough to warrant jeopardizing a stable, affectionate relationship. And so, as he walked those last few blocks, Peter bid a silent goodbye to Chantelle and prepared to make room for a new woman in his life, and a nice normal life it would be.

 

 

 

*********************************************
© 2001 by Ray Kitten. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.