An unhappy loner at Christmas is visited by an Angel and gets to change key moments in his life.

by Frank

 

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Admin Note: Originally published on BigCloset TopShelf on Thursday 01-06-2007 at 6:53 pm, this retro classic Christmas Special was pulled out of the closet, and re-presented for our newer readers. ~Sephrena
 

 

Bill looked at himself in the mirror and sighed. 30 years old and alone again on Christmas Eve. Not just alone, he was dressed up in women’s clothing. He was wearing plain cotton panties, such as one’s mother would wear, tan pantyhose that looked strange on his unshaved legs, and a 48C bra with empty cups. Bill was 5’10” tall, 290 lbs, with a flabby chest and a very unfeminine shape. He was also wearing a sundress he had bought online from Sears. It was a simple dress in orange and peach. He’d shaved as close as he could and had applied pancake makeup, blush, lipstick, and mascara. Stepping back to see the entire package in the full length mirror he cringed inwardly, and groaned audibly. ‘I look like the worst drag queen prostitute who ever lived,’ he thought bitterly. Bill had always felt like a girl inside, but he’d never told anyone about it. Instead, as he grew up, he lashed out and was surly to others. He didn’t go overboard hyper-male like some transgendered girls do, but he’d never presented himself as anything other than a brooding brute, either.

Disgusted with himself, he took off the dress, bra, and pantyhose, then hung them up in the back of his closet. He went to the bathroom, took care of business for the night, and went to bed. Laying there with the panties on, he masturbated while fantasizing about being a woman and having sex with another woman. Not for the first time at Christmas, he was alone, messy, and dressed. Bill cried himself to sleep, thinking about what a loser he had become, and had always been.

 

 

Later he was awakened by an intensely bright white light. Amazingly, he didn’t need to adjust to the brightness and was able to clearly see a lovely lady with long wavy blonde hair, smiling warmly. She was dressed all in white, a white jeweled crown, a white dress, white stockings, and even had a white wand with a star upon it. Bill thought ‘Okay, I’m dreaming, but this is the coolest dream I’ve ever had!’

The lady in white introduced herself as his guardian angel. “You can just call me Angel for short, Billie,” she giggled. “Billie, do you know why I’m here?”

He answered, “Well, I must be dreaming, so I’d have to say you are going to make my dreams come true and make me a girl!”

Angel smiled at him and shook her head. “That, I’m afraid, is beyond my abilities, Billie. Think of me as your spiritual advisor, almost your ghosts of Christmas past, present, and future.” “Let’s start with your past and work our way forward, shall we?”

“Ummm … okay, Angel,” a confused Bill replied. He didn’t understand what kind of dream this was, since she couldn’t grant his wish. Still, she was beautiful and he hadn’t been alone with a girl this pretty in many years, and he was terribly lonely inside.

“Okay Billie, go wash your face, and change into something comfortable, as we are going on a journey back in time.”

When Bill came back into the room Angel said, “You missed a bit behind the ears. Here let me get it for you,” she waved her wand at him. “There, much better. Ready to go? Good! Now hold onto my hand tightly, as I don’t want to lose you in the currents of time,” There was a twinkle in her eyes. There really wasn’t any way she could lose Bill, as he was her assignment for the day. She’d just told him that because she is a bit of a joker, and he really needed to feel physical contact with someone else to be able to trust them.

Bill held on for dear life and began to think that maybe this was not a dream. He also found it disturbing that she’d giggled when she talked about losing him in time. However, he seemed to be in this for the long haul, or until he woke up. He was about to ask her if this was a dream or real, when his hand slipped through Angel’s and he hit the ground.

“Billie, I told you to hold on tightly. Are you okay?”

Bill stood up and assessed himself. Except for some scrapes on his arm, he was okay. Then he realized he could actually FEEL the scrapes. This had to be a dream, didn’t it?

“Yeah, I think I’m okay. Sorry, my hands get sweaty whenever I try and hold hands. Angel, this IS a dream isn’t it?”

“Silly boy, don’t worry your … well not pretty … cute ...no… don’t worry your little head over things like that, you’re here to learn” she finally got out with laughter in her voice.

“Why do you keep calling me Billy? I’ve gone by Bill since I was 13!”

“You are Billie on the inside, and here, you’re only 10 years old. Look in the mirror.”

‘What mirror?’ Billy looked around and saw he was in the same bedroom he’d started in, only now it was decorated they way a 10 year old boy would have liked it. Baseball and football player pictures, ball and glove on the floor, comic books … it was HIS room from 20 years ago. Looking in the mirror, he saw he was 10 years old again. . He was a lot smaller than he remembered. God, he couldn’t remember ever being that skinny. His light brown hair almost reached his shoulders. His eyes were a brighter green, and not dull and sunken as they were in the present. All he had on were a white t-shirt and white brief underwear. Even the traces of makeup were gone, he noticed.

Angel giggled again and then started to talk to him. “Billie, you are ten years old, and it is December 21st.^t Does this particular day mean anything to you?”

Billy thought about it for a moment , but nothing came to mind, so he just shook his head and shrugged.

“Billie, why don’t you walk around the house for a bit and see if anything comes to mind, okay?”

Billy shrugged again and nodded. He gave his room the once over and nothing jumped out at him, so he decided to wander around the house and just enjoy himself for as long as this, whatever it was, lasted. Man it felt weird to be a kid again. He felt short and wiry as opposed to big and fat. He also felt younger mentally, even though he seemed to have all his memories.

He went out into the upstairs hall. The house was 2 stories, 4 bedrooms, 3 bathrooms, living room, game room, dining room, kitchen...etc. just like he remembered. Billy was confused.

Here he was a 30 year old cross-dressing girl wannabe loser, suddenly 20 years younger, in the same house where his parents, sister, and he had all lived. Bill’s parents had died in a car crash when he was 25, during an ice storm. His sister now lived 3000 miles away in Portland, Oregon. Bill had inherited the house and hadn’t ever moved. He was content in the house and city. He missed his parents, and seldom spoke to his sister. He was alone in the world, and very lonely.

Suddenly Billy became excited, and realized that if he was 10, then his parents were still alive and his sister still lived here! Though his sister was 14 months older, for many years they had looked so much alike they could be twins. Billy had always admired and envied his sister. He loved her and he loved her femininity. He’d always envied her because she was a girl and he was not. At this age, she had just started to develop. It then struck him what day it must be. This must be the first day he’d tried on her clothes.

Angel stood nearby watching and smiling. What Billie didn’t know, was that she could read his thoughts and could steer him in whatever way she felt he needed to go.

Just as Billie turned to ask her, she stopped him and said “It’s okay Billie; no one will be home for a few hours, so you can do whatever you want.” She giggled again.

Billy’s first impulse was to go into his sister’s room and check out her training bras and clothes. He remembered how when he was ten, he’d looked just like her when he dressed up in her clothes and how wonderful it felt. As he got older, girl’s clothes neither fit nor looked right. As his body grew and broadened both ways, he’d looked and felt worse and worse when he dressed. He couldn’t help himself though. He wanted to be a girl and be free to be himself. Suppressing that initial impulse, he went downstairs to look at the Christmas tree and presents instead.

He went into the game room where they set the tree up each year. There it was, just like he remembered. He saw all the presents, and even remembered the new aluminum baseball bat he had gotten that year. The family had also gotten a new computer, which had excited Billy so much he couldn’t wait to play with it. Bill remembered it hadn’t been all it was cracked up to be. He looked around some more and refreshed his memory with his parent’s furniture. When he went into the kitchen it was full of fresh food and snacks. In Bill’s present, there was some beer, milk, old eggs, and a loaf of bread. Bill ate a lot of fast food and pizza. Billy had had regular meals with the family.

Angel felt the time was right to start directing the activities a bit so they didn’t get bogged down. She still had other people to try and help before Christmas was over.

“Billie, it’s time we started to talk about what’s going to happen. Tell me what happened originally.”

“Well, everyone went to the mall for some weekend shopping, looking for Christmas bargains. I didn’t want to go. I hated shopping, and I always have. I may want to be a girl, but I don’t want to shop, so I stayed home and watched some television for a little while. I don’t know what programs, since I didn’t pay much attention to them. I just kept thinking about my sister and how she was starting to change. We had always been close growing up. She would play ball with me and I’d play house and dress up with her. But then as soon as puberty hit her, she became ‘mature’ and I was her icky little brother. I never told her, but that hurt me to the core since she’d been my best friend, as well as my sister.

“I went into her room that day to look at her pretty new things. While I was in there I had the urge to try them on. I put on a pair of panties, which I knew were older and probably not worn anymore now that she was becoming a ‘woman.’ They felt so nice, soft, silky, and somehow freeing. Then I tried on one of her training bras. Even though I didn’t have anything to fill it out, I had my first daydream of my own breasts growing. It was wonderful. That was about the time I noticed a growing bulge in the panties. I had grown hard when I put them on, but when I imagined having my own breasts I grew really hard. It hurt so much I got scared. I ran into my own room and took it out and, umm …. I don’t know, the whole thing was really overwhelming, I’m not sure if I was most excited by the clothes, the idea of growing my own breasts, or what.”

When Billy suddenly realized he was telling some of his most precious thoughts and feelings to a complete stranger, and a lady at that, he turned a DEEP shade of red.

Angel giggled again, making Billy turn an even deeper shade of red.

“Billie, you don’t have to be embarrassed. You were only ten years old, and feeling things that you really couldn’t comprehend. I don’t know if what you were feeling was truly sexual, or more likely emotional overload, but you didn’t do anything wrong, other than borrow you sister’s clothes without permission. I understand about what you did, and I even understand why you did it. After you did your business, what happened next?”

“I felt so ashamed that I took off her clothes as fast as I could. I had never taken my sister’s stuff without asking before. Now they were soaked with sweat and wrinkled. I cleaned myself up, then dressed in my own clothes. I took her damp panties and bra to the laundry room, and washed them. As I was getting them out of the dryer I heard the front door opening so I ran to my bedroom and hid the panties and bra under my mattress.”

“Did you ever tell anyone what you did?”

“Of course not! Then they would know my shameful secret!” Billy started crying.

“There, there, little one, don’t cry. It hasn’t even happened yet. Remember we are here to look at what happened, and why. Maybe we can make it better. I know you can’t help your feelings, but you really shouldn’t feel ashamed of them. Be ashamed of actions you take, like borrowing your sister’s clothes without permission. How you feel is beyond your or anyone else’s control”

She hugged Billie.

“Wh ...wha ... how do you mean? What can we make better? I can’t change the past, and this is just a dream isn’t it?” Bill couldn’t believe he was crying even though he did feel 10 years old.

“This is not a dream. Think of it more as an opportunity to make some small changes that might have long reaching affects on your life,” she said as she smiled at him.

“What can I do? I still want to go and try on her things while I’m smooth and have long hair and soft features. I looked so good before puberty hit me,” Billy stated as he wiped away his tears.

“Billie … BILLIE! Look at me when I’m talking to you! That’s better. Now then, let’s review what happened the first time you were here. You hid her underwear under your mattress and were ashamed of yourself, correct?”

Billie nodded. “You were afraid if you were caught that everyone would call you a sissy and your life would be over, and Jenna would be upset that you used her things?”

Billie nodded again. “First of all, you aren’t a sissy, are you?”

“Yes Angel, Ma’am, I am. I want to wear girly clothes and do girly things.” Without realizing it, Billy has started talking like a ten year old. “I wish I was just, you know, … like my sister in every way. She’s so pretty, and gets to do things with her hair and stuff. You know? Mom sometime stays with her and they brush each other’s hair for a long time and talk about girl things. I try listening the best I can through the wall, but I so want to be in there and do that too, ya know?”

“Billie, why did you feel ashamed when you wore your sister’s clothes?”

“I don’t know. I guess cause I’m a boy and shouldn’t wear girl clothes.”

Angel gave Billy a look as if she was waiting for more. “Ummm .. I guess cause I took the clothes without permission. Jenna and I always ask before borrowing stuff, and I dunno, I guess I’m ashamed because I’m a boy who wants to be a girl, and it isn’t right to feel this way.

Angel smiled at Billie and said, “Billie, has it occurred to you that your family loves you and maybe they would help you with this? Who do you trust the most, your sister, mom, or your dad? I’d guess it’s your sister. Why don’t you try talking to Jenna, instead of stealing her clothes and feeling ashamed?”

“But she’ll think I’m a sissy, and she might tell everyone about me!” Billy started crying again.

Angels sighed, then smiled, “Billie, has she ever intentionally hurt you? Even when she calls you her icky brother, does she do anything to hurt you? Do you want to repeat the acts of the first time, and live with shame“ or do you want to take a chance and see what happens? Oh, and for your information, a ‘sissy’ is a feminine BOY, who likes to be treated like a limp-wristed hyper-girl. What do YOU feel like?”

“I feel like a girl. I want to be a girl! I don’t feel as ashamed, now that you explained to me what a sissy is and is not. I still don’t want to be humiliated, but maybe Jenna will listen to me and understand. Are you sure about this Angel?”

“Well, look how things worked out the first time around. Could it really be any worse? I can’t tell you how she’ll react, as I can’t read her mind, but I know how close you were growing up, and that means she really loves you, even if she doesn’t always show it.”

She gave him another hug. “Okay, your family is on the way home now. They won’t see me or know I’m here. Only you will see me. You will be able to hear me, and I can hear your thoughts, so if you want to ask me anything just think it, okay?”

“Okay. You know, you’re really pretty, Angel” Billy said softly while blushing.

“Where did THAT come from? Thank you.” Angel replied with a giggle.

“Well, if this IS a dream, I just wanted to get it out while I had my courage up. When I talk to Jenna, it’s going to be the hardest thing I’ve ever done in my whole life!”

“That is true, Billie, but know you are safe here and you are loved.”

“Okay, thanks Angel, can I hug you for luck?”

“Of course you can! I love huggles!”

Billie hugged Angel , feeling warm and nice inside for the first time in he didn’t know how long.

“Now all we have to do is wait for Jenna to come home, and hopefully get her to let me talk to her.”

 

 

Billy and Angel watched television and made small talk while waiting for his family to come home. Angel made him watch Bewitched when he wanted to watch cartoons. Soon enough, the family arrived home. Jenna was very excited about all the new clothes she had bought and the gifts she had gotten for her girlfriends. After everything was put away his dad came into the TV room and sat on Angel. Billy was horrified until Angel rose and floated to another chair, giggling the whole time.

Billy’s dad noticed his son’s scared expression, and asked him what was wrong?

“Nothing, Dad, I just swallowed wrong and was trying not to cough.” Billy hated lying to his dad, but he couldn’t tell his dad he’d sat on Angel either.

Billy waited about fifteen minutes before he excused himself to go upstairs. There, he headed straight for Jenna’s room. The door was closed as it always seemed to be this year. Billy couldn’t help but think how silly she was. ‘She’s twelve years old, what does she have to hide?’ Nervously, he knocked softly on the door. There was no answer, so he knocked harder and actually heard his knock this time.

“Yeah? Who’s there?”

“Um, it’s me Billy,” he said in a strangled voice.

“What do you want?”

“I’d like to talk to you, if that’s okay?”

“What about? I want to call Debbie and tell her about my new stuff!”

“Well, that’s sort of what I wanted to talk to you about. Um, can I come in please?”

“I suppose, come in, and close the door behind you,” she grumbled.

Billy walked into the room that represented so much that had gone wrong with his life. He was more scared than he could ever remember being.

Jenna looked up at the little brother whom she felt was too young and too male to understand what her life was about, now that she was maturing into womanhood. What she saw really worried her. Her brother was looking at the floor, sweating profusely and shaking like he was freezing. At that moment, she forgot to be ‘mature’ and remembered how to be his big sister. She ran over to him and asked him, “What’s wrong? Why are you shaking and sweating like that? Why aren’t you looking at me?”

When Billy looked up, he saw Angel floating next to his sister. He felt Angel’s warmth fill him and he was able to muster up the courage to tell his sister his innermost feelings. Just when he opened his mouth, he was squeezed in the biggest hug anyone had ever given him.

As she hugged Billy, Jenna whispered in his ear, “Billy, I’m your big sister. I’m sorry I haven’t been nice to you like I should lately, but things are happening to me, and I get caught up in it with my friends and Mom. No matter how I act, you’re one of the most important people in my life, and always will be. Now come sit on the bed with me and tell me what’s wrong.”

Jenna held his hand as they walked to the bed. She continued to hold it waiting for him to speak.

Billy looked at Angel and saw she was crying and smiling at the same time. He looked at his sister and saw she had some tears as well, but wasn’t smiling. He thought to Angel, ‘How do I start without revealing I’m from the future and stuff?’

In his mind her heard her, ‘Forget the future. And forget the past. You are here in this moment right now, with your sister ready to listen and help you. Just speak from your heart and soul.’

“Okay, Jenna, this is really hard. Ohh, God, now I’m crying. I’m sorry.”

Jenna hugged her brother again. She was beginning to understand that whatever he wanted to tell her must be really big if he was in this much pain. “Shhh. Shhh. It’s okay, Billy. Take your time. I’m not going anywhere.”

“Okay … thanks, Sis. I’m okay now, I think. I’m just so scared of what you are going to think of me.”

“Billy, I LOVE YOU, so just tell me, and then we can fix it whatever it is.”

“Okay, here goes.” He took another deep breath. “I feel like a girl. I want to wear clothes like you wear. I want to brush your hair and have you brush mine like you do with Mom! I want periods and babies someday!! Since you’ve been getting all these nice clothes and stuff, all I’ve wanted to do was sneak in here and try them on, use makeup and make myself pretty like you are. I wish someone could wave a wand and just make me a REAL girl.” Billy looked right at Angel as he said that last part, and saw her giggle “I want to hang out with you and your friends and be one of the girls. I don’t want to be your icky brother Billy; I want to be your little sister Billie.”

Jenna was stunned. Her 10 year old brother had just told her he wanted to be her sister. This was too big for a twelve year old to handle.

When she didn’t respond right away, Billy broke down. “I knew it! You hate me Jenna! Everyone’s going to hate me!” Billie started crying again.

After a minute or so, Jenna hugged him again. “Billie, I love you no matter what! If you want to be a sissy, I guess you …”

Billy interrupted her “I don’t want to be a sissy. A sissy is …” he looked at Angel and she told him again, “a ‘sissy’ is a feminine BOY who wants to be treated like a limp-wristed hyper-girl I want to be a REAL girl, not a boy playing the part.”

“I never knew there was a difference. How do you know so much?”

“A little, err, birdie told me.”

“Hmmm, I don’t know if I like the sound of that. However I love you, and want to help you. Let me think about this for a while and get back to you. Okay?”

“Sure, I don’t have much say in the matter, I guess.” Billy hugged his sister to show he understood she needed time. “Thanks for listening.”

As Jenna hugged Billie again, without realizing it, she had already begun thinking of Billie in the female sense and as her little sister.

 

 

After Jenna left the room, Angel told Billie, “Okay little girl, time’s a wasting ... we need to move on down the road a bit to when you are fourteen.”

“Angel, what about Jenna? I have to wait and see what she does, and what happens now that the cat is out of the bag! I can’t just leave!”

“Actually, you can leave, and matter of fact, we ARE leaving. Take my hand!”

Billie refused, and stuck his hands in his pockets. Angel just sighed and grabbed his arm instead. Once again he landed on the ground with a thump, as Angel floated gracefully to the ground. He asked, “Why can’t I float to the ground with you?”

She giggled, “Next time I say give me your hand, give me your hand!”

Billie looked around and realized he was at his old middle school, Colfax. “What are we going to do here Angel?”

“’We’ aren’t doing anything. ‘You’ are going to do something you always wanted to do, but never could summon the intelligence to do when you had the chance.”

“Angel. If this is Colfax, and I’m 14, there are a million things I wanted to do!”

“This one is one of your biggest regrets in life. It’s not something you wanted to do at the time, but something you realized you should have done. What happened here, or didn’t happen here that you’ve always regretted?”

“Can you help me out a little bit more?”

“Well, it’s almost time for home room, so you’d better get going. You don’t want detention!”

“Home Room, you’re joking! I don’t even remember my way around this place.”

“Don’t worry I’ll guide you. Now, inside, second floor, Mrs. Debartolo’s class.”

Billie found his home room okay and even remembered where he sat. It was also the school library. They sat at long rectangular tables as opposed to individual desks like a regular classroom. After roll was called, they had about ten minutes free time. Billie looked at Angel and shrugged. She nodded, indicating the girl at the other end of the table.

Sherry Lazer was new to the area and lived on the same street.. She had tried to be friends with Billie, (or Billy then) who had a crush on Liza Jordan. Liza was also in that class. They weren’t close friends, but friends. She also happened to be Sherry’s best friend. Liza had a very nice figure, and was the girl that all the guys wanted to go with. Sherry was skinny and still flat as a board. so Billie paid her no attention and concentrated on Lisa.

Billie looked at Angel and shrugged his arms since he couldn’t ask out loud. He heard Angel’s voice in his head. “Billie, you can think to me and I can answer you.”

“Okay, what exactly do you want me to do?”

“What do you regret about Sherry, that you’ve regretted all your life?”

Billie suddenly understood. In the future, Sherry became an extremely beautiful girl, and was definitely popular and well liked by all. She and Billy had never become friends because he’d brushed her off when she was new and needed friends. Obviously this hadn’t helped his standing with Liza, either.

Billie turns to Sherry, and his brain freezes. He thinks to Angel, “What do I say to her, how do I start?”

Angel replies, “Be yourself, take an interest in her. Ask her if you can walk her home, or do something after school. Let her know you want to be her friend, and really listen to her when she is speaking.”

Billie looked at Sherry and feeling Angel’s warmth again asks “Sherry, are you doing anything after school today? Can I walk you home?” Billie ignored the other kids at his table when they laughed at him. Sherry looked at him and thought he was sincere. “Sure.” Then she asked if he’d like to sit with her and her friends at lunch. Billie accepted happily.

When the bell rang and everyone stood up to go, Angel grabbed Billie by the shoulder, “Come along, it’s time to move on, we have one more stop before home.”

“But Angel, I want to go to lunch and see what happens after school …”

“Sorry, but time marches on, kiddo.”

 

 

Once again Billie felt himself being swept through the currents of time. Bracing himself for the thump of hitting the ground, he was surprised to find he was floating gently down with Angel.

“Thanks Angel, That was a much nicer landing. Where are we now? When are we, for that matter?”

“We’re back in your bedroom. It’s November, the year before you graduate from High School. You went away for a year of college after you graduated, but that didn’t go so well. Do you know why?”

“Basically, I didn’t want to go to college. I wasn’t ready, and I just didn’t go to my classes. I stayed for three terms because I didn’t want to face living with my parents and being a failure. Even after I flunked out, they made me go to a local college for a year, where I lied and told them I got good grades, but usually just went to the mall or something. I worked then too, delivered pizza before getting a job at the grocery store. One thing I learned about myself was that I enjoyed working and doing a good job."

“Now all you really need to do is convince your parents not to waste the money on you going to college as you aren’t ready.”

“I did eventually go to Computer school and they helped pay for that.”

“Yes, but after wasting thousands of dollars at colleges.”

“I see what you mean. I did have a lot of fun away at college, but it didn’t really help me as an adult or with my future. I think this might be a hard one to sell my parents on. They have the ‘go directly to college after high school’ mentality.”

“You never know what you can accomplish without trying.”

“I need to think about this one a bit. I mean, I really wished I’d gone directly to computer tech from high school, but that was after everything else happened. On the other hand, I guess that stuff hasn’t happened, and I can prevent it from happening by talking to them now.” He paused, “I’m giving myself a headache all of a sudden.”

Angel giggled, “That’s part of the fun of time travel, you can confuse yourself very easily.”

“So Angel, what day is this and what time? Where is everyone?”

“It’s the week before Thanksgiving, 5:37 in the afternoon. Mom is making dinner, and Dad isn’t home from work yet. Why don’t you go talk to your mom while you have her alone?”

“I’d like some time to prepare what to say, Angel, this isn’t the easiest conversation I can imagine having with my parents.”

“Really think so? You don’t know it yet, but you’ve already had many conversations much harder than this with them. I’ll allow that they haven’t happened yet, so maybe you should think about it a little bit. I still think you are better off starting with your mother. For what it’s worth Billie, you already know how things turn out, so you can use that to your advantage. Good luck! I can’t help you with this one, sometimes there’s no easy way to convince parents of anything.”

Angel hugged Billie and left him to think. For the first time since arriving in this time, Billie looked around and saw the toys of his later teens. He had his stereo, records, tapes, and CDs. He put on Pink Floyd’s The Wall and a pair of headphones. He felt he did his best thinking with heavy loud music playing, and The Wall was very heavy on multiple levels.

Billie started to think about what had been happening since he first met Angel. First he’d told his sister his innermost secret, and she seemed to have accepted it and him. Then he’d been back in middle school and talked to Sherry and tried to make friends with her after he had ignored her the first time around.

He suddenly realized he was thinking in terms of, ”first time around,” like he was buying into this dream like it was reality.

“This HAS to be a dream!” he exclaimed out loud to no one in particular as he was alone in the bedroom. “I’m going to prove this one way or the other!”

Billie went to his desk and pulled out his compass from math class. “If I’m dreaming, I won’t feel anything. If this is real, hopefully Angel has healing powers,” he mused.

Angel was watching the scene unfolding below her and asked her superior what to do.

“Mother Erin, she’s about to do herself harm. Do I intervene, or allow her to hurt herself? My job isn’t to cause her pain.”

“My dear daughter, it’s her own free will to do as she wishes. Your job is merely to guide her. Unless she is about to endanger her life, you are not to intervene. Huggles, Little Angel”

“Huggles, Mother Erin!”

Billie extended the arm of the compass and positioned his left hand over the point. He took a deep breath and hit the point hard with the flat of his hand!

“SHHHHHHHHHHIIIIIIIIIIIIIIIIIIIIIIIIIIIITTTTTTTTTTTTTTTTTTTTTTTTT!!!!!!!”

He threw off the headphones, looked at his hand and couldn’t tell how deep into his palm the compass had gone, but he knew it hurt like hell.

“Angel! Help me!”

A few seconds pass, then a few seconds more. “Angel!? Where are you?”

Just then, there was a knock on his door and his mother’s voice. “Billy are you okay in there?”

“No mom, I hurt myself!”

His mom came into his room and looked at his hand, examining the wound. “How did this happen? What were you doing?”

“I just wasn’t paying attention and it had been put away point up and I hit it just now.”

“Ok, come into the bathroom and I’ll get out the first aid kit.”

Billy followed his mother into the bathroom and sat on the toilet while she got out some antibiotic cream, band aids, and peroxide.

“Ok, I’m going to pull this out now. Be my brave little guy,” she said smiling at him.

“OWWwwwweeee!! Thanks Mom!”

She cleaned the wound with the peroxide, then dried it lovingly as only a mother can do. After applying the cream and a band aid, she kissed him on the forehead. “All better now?

“Yes, Mommy, I mean Mom ... well, actually I’d like to talk to you about something that is really bothering me.”

“Sure Hon, can we do it downstairs while I work on dinner? I’ll let you out of helping me since you are injured.”

Just as they were going down the stairs, he saw Angel was with them. He scowled at her and thought angrily at her. “Where were you,” he thought angrily at her.

“I was always nearby watching. You chose to poke yourself, I didn’t tell you to do that. It’s no different than you choosing your words now with your mother, or your sister before.”

“Billy, what in the world are you scowling at? I thought you wanted to talk to me.”

“What? Oh, right, sorry Mom. Here’s the deal. I don’t think college is the answer for me when I graduate. I don’t think I’d do well there and I wouldn’t want you to waste thousands of dollars on me for nothing.”

“WHAT? Of course you will go to college! You did well enough on your SAT tests and should be able to get into Pitt or Penn State. You may not get into the main campus of Penn State, but you can start at one of the other locations for the first two years. If you go to Pitt, you can still live here and take the bus back and forth. No, you’re going to college. What a silly notion!”

“Mom you’re not listening to me. Are you willing to take handfuls of money and throw it down the garbage disposal? That’s what you’d be doing. How about instead of College I go to a computer school? Maybe Computer Tech? I love working with computers, and I already know as much or more than my teachers at school. You can put the rest of the money into a savings account for when I do go to college or get married or something. Please?” He started crying, something he hadn’t done since he was thirteen and had broken both his arms playing football.

His Mom noticed this and looked at him as if for the first time and saw how serious this way. “Well, I’ll talk to your father, and then the three of us will talk together. If you are not going to do well, then it would be stupid to waste the money. I don’t know what your father will say though.”

Billy hugged his mother, which shocked her, as he hadn’t initiated a hug for as long as she could remember. She hugged him back tightly. “Mom, I love you, but I can’t breathe,” he laughed.

Mom laughed too, and they had their first real moment since he was a little boy.

Billy went back to his bedroom, where a very happy tearful Angel hugged him as soon as he entered the room.

“Okay, Billie, are you ready to go back home to the present?”

“So everything will be different when we get there?”

“Not exactly … it’s a process. We’ll get there and then we wait for time to catch up to you.”

“I don’t understand.”

“You will, take my hand. Ok, here we go!”

 

 

Billie floated gently to the ground with Angel holding his hand. He looked around his bedroom and it looked the same as it always has.

“What gives Angel? What was the point of all that? I poured my heart out to my sister, talked to a girl I’d blown off originally, and told my mom I didn’t want to go to college. Looks like the same old me in the same old place. Heck, even my panties are wet and gross again!!”

Angel patted his head, “Wait for it. Time has to catch up with us now.”

“What the heck does that …what’s that sound?”

Billie felt and heard what seemed like a tidal wave hit him and knock him to the ground. His skin felt like electric ants were crawling all over his body.

Suddenly Billie felt a surge of memories flooding into his brain. After the talk with his sister, nothing had happened for the rest of that day. The following day she had come to his room to talk to him some more. “Billie, I really want to understand what we were talking about yesterday. How do you really know you want to be a girl? Do you know anything about being a girl?”

“No Sis, I just know I don’t feel right as a boy. I envy everything about you. You get to wear pretty clothes, play with dolls, and try things with your hair, girl talk. You have a special bond with mom, and are so much closer to her in a way I can’t be.”

“Ok, how about this? For the time being, it will be just our secret, and anyone else you want to know about it. Don’t look so scared! I’ll keep it a secret. When we’re alone we can dress you up, and I can teach you girl things like makeup, doing your hair and that kind of stuff. How does that sound?”

“Really? You’d do that for me? I love you sooo much Jenna, you just don’t know!” They gave each other a great big bear hug to seal the deal.

Then Billie kissed Jenna on the cheek. He’d never kissed her before. “Billie, why did you kiss me?”

“I don’t know why, it just felt like the right thing to do just then.”

“Wow, maybe you should have been a girl!”

They both giggled at that remark, but how right Jenna seemed to be. Over the next six months, Billie learned how to dress in his sister’s clothes. She showed him what she knew about makeup. They did each other’s hair dozens of times, and became really best friends and sisters.

Then Jenna began thinking it was time to tell Mom about what was going on.

“JENNA! NO! We can’t tell Mom. She’ll be mad, and tell Dad. Dad will spank us and yell at us. I don’t even know what Mom will do!”

“Relax little sister, I’ll talk to Mom first, and then we’ll let her see you dressed up. We just need to show her how right this is for you. You are twelve now, and are going to start growing up soon in a manly way, and who knows how big you could become.”

“Ok, Jenna I trust you with my life. When do you want to tell her?”

“Let’s do it tomorrow, after lunch.”

“Okay, I guess. I’m scared, though.”

“I know, and I wish I could make you not scared, but I don’t know how.”

The next day after lunch, Jenna sent Billie to get dressed. After about half an hour had passed, he heard her yell for him to come downstairs. As he entered the kitchen he heard his mom talking, “Jenna, this has to be the silliest … oh my goodness ... Billy? Why you look just like Jenna.”

“Thank you, Mommy. I hope you aren’t mad at me,” Billie was shaking.

“No, I’m not mad at you Son, err … Honey, I don’t know what to think of this.”

“Mommy, can I be a girl? What will Daddy say? What will he do?”

“I’m not sure, Billie. I will have to talk to him and see what he thinks. I need time to think about this too. I can’t believe how pretty you are. Oh, look, he blushes just like a girl, too.”

Billie was in heaven; Mom wasn’t mad and seemed to really like him as a girl.

“Jenna, take you broth … err … sister upstairs and get him looking like my son again, please.”

“But Mommy, I thought you like how I look,” said a crestfallen Billie.

“You look very pretty dear, but you’re a boy still, and should look like one.”

“Yes Mom. Mommy, can I have a hug before I go up, so I know you aren’t mad and you still love me?”

“Of course I still love you baby, but this is quite a shock; come here.”

They hugged tightly and Billie felt contentment.

Later that night Billie’s mom and dad had a long talk. Eventually his dad called him down to talk, man to man, as it were, “Okay Billy, in your own words tell me why you think you want to be a girl.”

“Dad, I don’t ‘think’ I want to be a girl. I ‘know’ I do. I’ve always felt this way. I’ve always been jealous of Jenna and the things she gets to do because she’s a girl.”

“Your mother already told me some of what you think you want. I think you need to have your head examined!”

“Dad, I think that’s a great idea. When can I make an appointment?” That threw his dad for a loop. He hadn’t expected his son to WANT to go see a shrink.

“Well, your mother and I will have to investigate this, and I’ll get back to you when we find the right kind of doctor to deal with this … err … whatever this is. Okay champ?”

“Okay Dad, thanks! I love you, Dad!”

“I love you too, Billy.”

Billie could tell his dad wasn’t happy about this, but he didn’t seem mad either, so that was a start. He could see a professional now, and maybe start hormones and …

For the next several years, Billie saw a psychologist who specialized in transgendered people. He believed Billie to be a classic transsexual. Due to Billie’s age, however, he didn’t want to have him start hormones that would change his body irreversibly until he was old enough to make the decision for himself. This particular doctor didn’t believe in hormone therapy for kids under the age of 17, as he felt they weren’t mature enough to understand the ramifications, and he didn’t think the body’s natural growth should be short circuited.

Through the years and with family counseling his dad came around. He continued to live as a male in school and in any local activities. But at home and when they went out of the city, he could be Billie Jean or just Billie. He didn’t have very many friends though, so he stuck close to his sister and her friends when they allowed. Her friends weren’t warm to him, but they weren’t mean, either. His sister tried to be as inclusive as she could be, but still, he was just a younger brother as far as her friends were concerned.

Back in the present, Billie stood up and looked around again. Now his bedroom was nicer, cleaner, more feminine. He looked at himself in the mirror and saw no signs of five o’clock shadow. He remembered having years of electrolysis. He was still about 5’10” tall, big boned, and overweight. But his body shape was different now. His fat distribution was in the female patterns. He had a big bottom and thighs now. His legs were shaved; he was wearing a properly fitting bra. The cups held real breasts due to the hormones he’d taken. He had on a different more comfortable pair of panties that were dry. He was also wearing a light red nightgown, bunny slippers, and rings on painted fingers. His hair was past his shoulders and a dirty blonde shade. His green eyes weren’t dull and lifeless, but seemed alive with a twinkle. He checked under his panties, finding that yes, he was still a male. ‘I guess I can’t have everything,’ he chuckled to himself.

When Bill looked in the mirror, he thought, ‘Not too bad, I guess. I still look too manly, but it’s much less obvious than it used to be.’ As far as his memory went, he was still alone though. His sister Jenna lived in Philadelphia and he visited her often. She and her family came home to Pittsburgh many times each year. They were always talking together on the phone more days than no., Billie and Jenna were truly like any other sisters, except they didn’t fight quite as often.

He turned to Angel and said, “Not too shabby. Not a ten, but not too shabby, I can live like this.”

Angel giggled and said, “Wait, there are more changes coming, that was just the first wave.”

 

 

“More changes? What else is going to …” Billie stopped talking as the second time wave washed over him. Again he was flooded with memories, but he didn’t feel anything physical.

He now had new memories of his middle school years and onward. He remembered after making friends with Sherry, that they became extremely close friends. Sherry was Liza’s best friend, and through the mutual friendship, he became close friends with Liza, too. Unfortunately Billie was still a geek and never one of the popular kids. But he did have friends who were girls now. He also now had guy friends from the computer club and others because he was friends with Sherry and Liza.

Eventually, Billie felt safe enough with the girls to tell them his secret. Sherry was very accepting and encouraging of Billie, and she became best friend to Billie as well as Billy. Liza became somewhat hostile and rejected Billie. yet as long as he kept it to himself, she was still nice to him. Neither Billie or Sherry could understand what her problem was, but they respected her wishes on the matter. Billie was hurt, but wanted her to stay in his life.

After college, both girls stayed in the city. ‘Sherry lives about a mile away and Liza lives … ‘Billie turned around and looked at the bed. It was a king-size bed now, and someone, was fast asleep under the covers. Billie was filled with happiness as he remembered that Liza is his wife. It turned out that she was lesbian, but was ashamed of it. She’d lashed out at him in a kind of transference thing. Yet she had actually come out to Billie her senior year of college. She and Billie became closer, and since he’d been taking the hormones and was going to be fully female one day, it was a perfect match.

Looking around the room, the furniture was much nicer, due to their having two incomes, and Liza’s excellent taste. Billie was a girl with a lot of Y chromosome still in her. So she was more than happy to let Liza decorate the house. The rest of the house had also been upgraded in looks and standard of living. There was even food in the kitchen now.

Billie looked at Angel, “I’m not alone anymore. Angel, aside from having the SRS, I don’t know how I could be any happier. I still remember the way it used to be, and how lonely I always was. It seems those memories are fading and blurring now.”

“They are fading because they no longer happened. Get ready, here comes the next wave.”

Billie again felt the flood of memories and the electric ants all over his body.

After high school, Billie started her real life test and became the woman inside permanently.

After much arguing with his parents, Billie had gone to Computer Tech, a trade school, to learn programming after high school. Her parents put the money they would have used for college into a special bank account. If she did well at school, and got a good job, the money would be hers. There was more than enough money for laser hair removal, and her sex change surgery. Billie graduated at the top of her class. She had a special affinity for computers, and she’d had great incentive to do well. She got a job at a local company that built rolling mills for the steel industry. She developed a mill simulation program that earned her a large bonus and raise. Within three years, she was head programmer, and the company paid for her to take classes towards a Computer Science degree.

Billie’s parents retired early and moved down to Florida. They felt they had done a good job raising their children and deserved to treat themselves for a change. The day of the car accident, they were on a beach, arguing about going over to the nude beach next door. They were alive and well today.

Back in the here and now, Billie checked inside her panties again. Sure enough ‘he’ was gone and she was a girl inside and out. With her success and her parent’s college money, she’d had the surgeries to become a woman. She’d even had feminizing facial surgery and some liposuction. But the battle of the bulge was a losing one as her big frame craved food.

Crying tears of joy, Billie told Angel, “I can’t believe how happy I am. You’re truly a gift from heaven. I have a great family, friends, a career. Just yesterday I was a nothing, now I have everything. Thank you Angel, thank you for everything!”

Angel was crying herself as she came over and hugged the happy girl. She felt it was a slightly awkward hugging as this was a large girl. ‘She is happy and that’s the important thing. She is a nice person now where he had originally grown into an unhappy surly person who shut everyone out, due to his inner turmoil. Still, there is one more thing I can do for Billie.’

Angel said her farewells to Billie and told her in a few minutes she’d forget any of this had even happened.

“Merry Christmas, Billie.”

“Merry Christmas Angel. Thank you.”

“You’re welcome. Now go snuggle with your wife”

Angel disappeared and Billie did go snuggle with her wife. They never divorced after her surgery, so they live happily as wife and wife.

 

 

Angel, felt there was one thing left undone. She traveled thirty years back in time to when Billie had just been born. She looked at the sleeping baby and waved her wand saying “Change little one, gene by gene so that when you grow up you will remain small boned and thin. You will grow to be 5’4” tall. You will always be within ten pounds of your ideal weight. When you start your transition you will be able to pass that much easier.” She tapped the baby on the forehead and they both giggled.

Angel was happy, she’d done all she could short of changing him into a girl. That was beyond her abilities. She giggled to herself, it was time to go help her next client.

“An Angel’s work is never done.”

The End

Notes:

Special Thanks goes out to the following:
Scotty Bishop for some fantastic editing
Holly Logan also for some fantastic editing and mentoring a new writer!
Angel O'Hare for advice, guidance, inspiration, and friendship

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