An Engagement Ch. 01

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How to become a Man while Dressing as a Woman.
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St. Evies―An Engagement

Introduction: Ruminations

Pedro de la Garza had a problem.

He was a young man, posing as a girl, which could not last forever. Every day brought new challenges and some had almost tripped him. He was also living on charity, which offended his sense of dignity. Even if he could, Pedro did not want to continue posing. Now that he had a steady job, with improving prospects, it was not necessary. Other living arrangements could be found. If it were not for Angela, Pedro would have thanked all the girls and left.

Angela was the problem. Pedro wanted to stay near her, which meant continuing the masquerade. For better or worse, Angela had given Pedro her attention and he had offered her his heart. She seemed inclined to accept, but things are rarely that simple. Since they both knew the charade for what it was, Pedro could not court Angela as Patricia. It was complicated, though not urgent. Not yet.

The issue was always in his thoughts.

Chapter 1: Of Ice Cream and Windy Days

Thinking constantly about Angela did not mean nothing else mattered. While his education was lacking, there was nothing wrong with Pedro's mind. An education can be mended. The bank had a chronic need for bilingual clerks at all levels. In the space of weeks, Patricia was promoted three times. With the promotions came responsibility for higher level accounts―and more material to study. In this, Deirdre was a huge help, but Finance was not in her area of interest. Soon she was out of her depth. As most of the girls would, she turned to Edith Dryden.

By this time, Pedro had regular contact with all the girls on the fifth floor, save Edith. They met the first night, but rarely since. Patricia quickly moved into the elite cliques, while Edith remained among the outsiders. Each knew the other was around, but their paths rarely crossed. Neither had cause to seek the other out, until Pedro's job provided a reason.

In many ways, Edith was the anti-type of Gretchen, who had tired of the novelty of a man on the floor almost before the first night was over. Edith let her gaze linger and took in details. Gretchen was a passable student, when prodded. Edith was Dean's list at Columbia. Gretchen was impulsive, flamboyant, and irrepressible. Edith was quiet, methodical and precise. Gretchen made occasional sexual use of Pedro. Edith had had no plans to add Pedro to her short list of lovers. They had one thing in common. To them, Patricia did not exist; they saw only a man in women's clothing.

For his part, Pedro noticed the quiet girl in the back of the room. Her penchant for observation over participation intrigued him, but was a passive thing. As his following grew, Pedro neither dismissed her nor gave her much thought. When he considered Edith at all, it was usually to wonder why she behaved as she did. In passing, Pedro noticed something no one else in the Hotel had ever seen―Edith could be a major beauty.

It was not obvious. Pedro was slow to piece things together, but no one else saw it at all. It came to him as he practiced theory of makeup. He would select a girl and mentally critique her presentation. Edith received the only failing grade. The more he considered how she presented herself, the more confused he became.

Edith had near waist length hair, which she pinned tightly and covered it with an oversized hat. Her eyes hid behind horn rimmed glasses, which also concealed her cheekbones and often slid down her nose. Her clothes were seldom stylish and usually miss-mated. Her only makeup, when she remembered, was lipstick in an outdated shade that clashed with her eyes and skin tone. It was as if Edith's goal was to be unattractive. If so, she succeeded.


It took effort, because the raw materials were outstanding. Pedro, as his eye for makeup and presentation improved, could not help but notice her high cheekbones, hazel eyes and rich auburn hair. Few others saw the hair at all. Pedro had seen it on the rare occasions she had it down for brushing. Edith's eyes were always on view, but the heavy glasses were distracting. Her thin figure was disguised or hidden, never accentuated. She had a barely noticeable chin dimple, which added interest to a highly symmetrical face. Edith hated it.

In short, Edith considered herself too tall, much too thin, with mousy hair and an embarrassing dimple. If she were forced to pick a good point, it would have been her teeth. The reasons for Edith's odd belief were complex. It is sufficient to say, she thought herself plain and no one ever corrected the misimpression.

Since she did not think of herself as one of the good looking girls in the hotel, Edith's chosen niche was as one of the house brains. Another generation would call her a nerd. She was the house authority on several subjects, not even including her English Literature major. Everyone knew her as someone to go to with a homework problem or to prepare for a test. It was this line which eventually brought Edith and Pedro together.

Pedro was studying a book the bank had provided. He was doing well with basic English terms, but banking has a technical language of its own. When the terms became more than Deirdre could handle, she suggested a call on Edith. They met. Half an hour later they went their ways, but Pedro's interest was piqued.

Sensing that this was not safe ground, Pedro sought Edith while Deirdre was out clubbing. Edith was shocked. Though she did not consider Pedro to be one of the girls, his status in the hotel was undeniable. Edith never received much attention, especially not from the most popular boy she knew. It jarred her to realize Pedro sought her for her own sake.

It was awkward. Pedro did not want to offend Edith by asking bluntly why she made herself so unattractive. She was at a loss for conversation topics, since there was nothing to study. Pedro resolved the tension by offering a go out for some ice cream. At St. Evies, this was a common excursion, since the parlor was on the same block. Girls often went there to meet dates, especially those they did not want exposed to Miss Walker.

Soon they sat licking almond fudge double dip cones. Edith asked about Pedro's job. Pedro painstakingly told her. With ease born of hundreds of hours tutoring, Edith drew out a fairly complete picture. Pedro positively glowed at conveying so complex a topic, in English. Her professional pride sated, Edith found herself relaxing and enjoying the occasion. Both would remember the night as a landmark.

The first night out established a precedent, which quickly evolved into a pattern. Whenever Patricia was not invited out, or when Pedro was not coming as himself to pick up Deirdre, they would walk and talk. These conversations helped Pedro's language skills as much as time in at the library would have. This was important, since the library was Patricia's usual excuse to check out of the hotel.

On one of the walks, the wind blew off Edith's hat and several of her hairpins. She was flustered and fussing when Pedro caught her hands, "No. Is good. Everybody will see yourpella linda,your pretty hair." It was the first occasion in years that anyone had called any part of Edith pretty. She turned red. Pedro would have none of it. "Tu eres muy bonita." (You are very pretty). If Edith had been surprised and embarrassed before, this shocked her speechless. Seeing her clear disbelief, Pedro tsked, "Come. I show."

He pulled her into a shop entrance. A nearby streetlight gave a good reflection. Pulling out his makeup kit and a comb, Pedro unpinned Edith's hair and combed it out. He lined her eyelashes, blushed her cheeks, glossed her lips. He could do nothing with the clothes, but he bunched the excess in the back, to show her figure. When he was satisfied, Pedro stood her up straight and turned her to see the reflection in the window.

In some ways it was deja vu. As Pedro had once seen his feminine side in a full length mirror, so Edith saw a new person in store window reflection. She did not recognize the woman in her own clothes. The skinny, mousy haired girl was revealed as a long legged, auburn haired beauty. Edith flung her arms around Pedro and kissed him. After a moment, he kissed her back. The moment lingered.

"Golly." Edith was not given to strong language, but the intent was there. After a moment, she went on, "If we're going to do this, you should change."

Pedro was taken aback. Since most of the girls thought of him as female, much of his lovemaking had a lesbian flavor. What had just happened was unmistakably heterosexual. Still, Pedro was prepared. His outings with Deirdre taught him to stash changes of clothing. He lost a change, from time to time, but not often. Most of those that found his stash decided the clothes were too small to bother. In less than ten minutes Patricia was gone. Pedro took Edith's arm and led her on a stroll.

It was a perfect night for such things. It was warm, but breezy enough to want an arm around the waist. The moon was full and there was nothing to distract them. It was with shock when Edith finally realized they were out after curfew.

They rushed back to the hotel. As they approached the entrance, Edith realized another problem―Pedro could not go in and Patricia was still out. Rushing up to Miss Walker's desk, Edith improvised. "Miss Walker. Look who I just met. I mean we had met, but I never really had the chance to get to know him. Anyway, he came by to see Patricia and we got to talking. Patty's holding our chair at the parlor, so I could check in. Isn't he something?"

Miss Walker had trouble deciding which was more amazing―the sight of mousy little Edith looking attractive or the fact that she was gushing. In Miss Walker's expert opinion, Edith was the most self-controlled girl in the hotel. She told Edith to be back in 30 minutes. When they had gone, Miss Walker reflected on how much less boring it was with Patricia around. She was the best thing to happen to the house in years.

Miss Walker worried, because Patricia never dated. Hard work was good, but how could she find a good man?


Chapter 2: Double Date


Outside, Pedro and Edith got well away from the hotel before they both dissolved in laughter. Then they went to the ice cream parlor and bought cones to use as props when they returned. It occurred to Pedro that his life would soon be more complicated. He was correct. Though he would not have put it in those terms, Pedro's life was not entirely his own. It did not take long for conflicts to develop.

Many of the girls used Patricia as a chaperone. A boy would call for one of them and Patricia would accompany them out the door. At that point Patricia would leave them, to go to the library to study, to the theater to watch a movie, or whatever. Patricia was such a good customer that several of the area theaters owners had offered her a job as ticket taker. This routine would change.

Instead of going to the library, Patricia would change into Pedro clothes and meet someone. Originally it was Deirdre. Increasingly it became Edith. Either way, they would go to the library to study. With their tutelage, Pedro's mastery of both English and banking was becoming quite secure. Often as not, he would return his escort to the hotel, go back out, then return as Patricia, with another girl. Timing occasionally became intense.

Worse, jealousy began to rear its ugly head. Deirdre felt proprietary about Pedro's masculine guise. Their sessions in her playroom had become increasingly hard to schedule. Pedro was acutely aware that Deirdre felt neglected. It all came to a head one Saturday afternoon when Deirdre, going, met Pedro and Edith coming. In short order there were words flying and Pedro trying to calm both down. Finally, he put his foot down.

"Silencio!You will find someplace to decide that is not a public street."

This was followed by a squabble over a proper place. Eventually, they went to the apartment. For half an hour he let them scream themselves hoarse. In passing Pedro noticed that Deirdre looked even more attractive this way, but Edith did not have the coloration for it. Eventually the girls wound down, flushed and panting. Pedro asserted his role.

"What is all this shouting and names calling. You are both girls mine. Deirdre, you must know that Edith is my special friend. I will spend time with her, for I enjoy it and she has taught me much. But,chica mia,you are also mine. You follow me and I care for you. That is the way of things. To me you give your obedience. To you I give my promise to never leave you, or forget you, or put you aside, for as long as you and I both live. Untilmuerto, intiendes?The Dark Lady, she no come this year. Now, my girls, come to me and be friends."

Pedro did not yet know his strength. The fact that he had risen to a high status in a hotel full of pampered rich girls did not impress him. The fact that he had impressed a strong girl sufficiently to make her his devoted follower was lost on him. Without intending to, he stamped both girls with roles they would carry for the rest of their lives.

Deirdre would be Pedro's vassal and he her Lord. Her honor, her duty, her body, her life would be his forever. He would marry and she brought many suitors for his approval. Never would they be more or less to each other. For her part, Edith understood that while they were friends and might be lovers, there would never be a marital proposal. That was alright. She did not believe in marriage. The lover part began almost immediately.

As Pedro said "Come to me and be friends." he held his arms out. The girls moved into them. The embrace was long and full bodied. Pedro muttered "Bien. Muy bien." not realizing that he had two excited females in his grasp. They glanced at each other, forgot the fight and conspired against him, all without a word.

Deirdre led the three of them into the bedroom. Pedro did not understand their intent til they had him on his back and themselves on top. Deirdre, never at a lack for restraints, produced rope sections from a drawer. Before he could do more than protest, Pedro's hands were tied to the bedposts. That done, Deirdre turned to Edith.

"Well Edie, what should we do with him now that we have him? Personally I think he has too many clothes on." In short order Pedro was wearing only an unbuttoned shirt. His substantial length pointed to the ceiling. Deirdre was about to speak, when she noticed Edith staring at Pedro's erection.

Edith was not a virgin. She had one sexual experience, because Gretchen had insisted and provided a lover. It had been quick and embarrassing. The lover darted almost before he had his pants up. It was one of many things that confirmed in Edith's mind that she was unattractive to men. Typically, she ignored her own feelings toward men. For the first time Edith had the chance to observe male anatomy and her feelings rushed to the fore. Deirdre, both knowing and guessing the situation, took charge.

"Edie, lets get those clothes off you. How in the world are you going to fuck a man wearing all that?" The word "fuck" brought color to Edith's cheeks. Her mother would have been shocked to find that she even knew the word. Slowly, carefully, resolutely she began to remove her clothing as Pedro watched. It was her first role as a stripper. Famously, it would not be the last.

The effect on Pedro was electric. He had been ambivalent about being tied up, but seeing Edith voluntarily remove her clothing put things in a new light. His relationship with Deirdre not-with-standing, Pedro never considered that a woman, particularly an attractive woman, would have such thoughts about his male form. Edith's slow disrobing teased him to a fever. There was no mistaking the set of Edith's jaw. She meant to have her man, even if she had to rape him.

All too soon she was naked, aroused, and unsure of what to do. Deirdre came to the rescue. Handing Edith a peacock feather, "Here Dear. Find out what's sensitive." So began the game. A touch here. A caress there. Never twice in one place. Deirdre shed her clothes and joined in, licking, biting and blowing all over Pedro's torso. Just as he was about to explode, Deirdre pulled Edith aside.

In a whisper, she said, "Listen Dear, I can't afford to take chances this time of month. If you want him, he's all yours. Are you safe?" Edith took a moment to think things through. Her period had ended three days before, so she nodded.

Deirdre nodded, "All right Edie, I'll take the top. You take the bottom. Just take a little and work it in and out. Try to make it last." Again, this took a moment, but the physical realities of the situation were obvious enough. Again, Edith nodded. The conspiracy established, Deirdre whispered, "All right then." as they turned to their victim.

Pedro wondered what the conference was all about. His flag was down to half mast when it broke up. Before he had a chance to object, Deirdre had her her pussy in his face. Familiar with this situation, Pedro began to eat Deirdre, expecting a pair of lips on his cock. He got them, but not the lips he expected.

The sensation of a cunt sliding down and gripping his cock was not totally new, but close enough. This well lubricated pussy was new to the work and tight. Up. Down. Rock forward. Rock back. In. Out. Up. Down. Faster, then slower. Edith was a quick study. With a little experimentation, she understood the motion and worked herself to a climax. Pedro beat her to it by an eyelash. They were bouncing and shaking when Deirdre came. Thereafter, the whole pile collapsed into a heap in the middle of the bed.

As they dressed, Pedro said, "Perhaps next time with music." Deirdre laughed and Edith soon followed. This was to prove the longest lasting relationship save one. The first Saturday of every month the three of them would get together for games. After Pedro married, they became four. The one rule was that Pedro had to follow orders. This was a relief, since he would soon be giving orders almost continuously.

Edith and Deirdre, with almost literally nothing else in common, became fiends for life. It was a lasting benefit to both. What one learned, by high road or low, she would teach the other. Both came to have an ear on the other side of the fence. They would be bridesmaids for each other. Once again, Patricia's status received a boost. The foundations on which Pedro would build his life were being laid.

Chapter 3: Four's Company

All good things must come to an end. While in many ways Pedro enjoyed the hotel, after a few months he knew it could never last. Spring had become summer. Summer had become fall. A new wave of girls arrived, many to attend one of the colleges in the area. In a tribute to his skill in his role, none of the rumors concerning his maleness were taken seriously. He blended seamlessly with the daily life of the hotel. From all appearances things could go unchanged forever.

In other ways, he was meeting frustration. He had long since been promoted to a full time position. While this was gratifying, it also cut into his time. With two lives to maintain, time was quite precious. Also he was beginning to chafe at being the house charity case. Having his own apartment, closer to his work, would make things much easier. He could also be seen going in as either Patricia or Pedro. He began looking seriously for a place.

In this he had unexpected help. Angela, his angel from his very first day, was quite receptive to the idea of his moving out. She called on her array of resources to help him find a suitable apartment. Being who she was, an answer came down within weeks. It was, appropriately enough, a Sunday when she took him to see it. She insisted that he bring a change along.

Fully furnished, rent controlled, in a respectable neighborhood, it was the kind of place some New Yorkers dream about their whole lives. Angela's cousin, normally into high steel office buildings, arranged a private viewing for her. Pedro quietly agreed, with reservations, because Angela asked it. As with much else, he was becoming wearied with charity. For Angela, he made an exception.

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