Synopsis:

A teenage boy, secretly dressing in female clothing, is caught by his parents. And this is only the first surprise of the day.

Story:

A Day of Surprises
by
Valentina Michelle Smith

It was Saturday morning. Marty Lang was in his room putting together a term paper for his high school history course. The subject of "Medical Care and Practice in Colonial America" was a bit dry, but he found ample material in the library and on the Internet to flesh out a 10-page paper. He was grateful for the tools he had at his disposal. The word processor made such items as footnotes, a bibliography, and a table of contents a snap.

"Marty," he heard his mother say. He turned to see her head peeking through his open door. "Dad and I are getting ready to leave for the shore," she said, referring to the family property in Ocean City. "It's a shame you have that paper due on Monday. Are you sure you don't want to come with us and take the laptop?"

Marty smiled. "It' really OK, Mom," he said. "If I came to the shore I'd be too distracted with the beach and the boardwalk to finish. I really should stay and get it done."

"I just worry about you being by yourself," she said. "Will you promise me at least that you'll eat a proper dinner and not just send out for a pizza?"

"Oh, don't worry, Kate," said a voice from the hallway. It was Marty's father. "The boy can handle himself for one weekend. He's sixteen now. And I don't think one little pizza will kill him."

"Dave," she said, "I'm his mother. You know I'm going to worry about him as long as he lives."

"I know, Kate. I worry about him too. But we have to let him out of our sight once in a while. I think we can trust him."

"Mom," said Marty, "don't worry. I'm going to be here at home the whole time getting this paper done. What kind of trouble could I get into?"

"Well, I guess it's okay," she relented. "But with Joanne away at college and you here all weekend, your father and I will be all alone…" She paused for a moment, as a hint of a smile crossed her face.

"That's right, babe," said Dave, "just you and me and the seagulls. I think we can find something to keep us busy."

"Well, when you put it that way," she said, turning to embrace him, "how could I refuse?" They kissed each other.

Marty cleared his throat. "Hey, you two, wait until you get to the shore, okay?" They laughed.

"All right, Marty. I guess we'll all be fine for the weekend. So how about giving your Mom a kiss goodbye?"

"Okay, Mom." He gave his mother a kiss on the cheek, and then gave one to his dad. The Lang family had no shame with expressing familial affection.

"Let me help you with your suitcase, Mom," Marty offered. He picked up the bag and walked out to the family car parked in the driveway. Kate and Dave exchanged another round of hugs with Marty before leaving. Then they drove off as Marty waved goodbye. He watched them drive down the block and turn.

Marty returned to the house, locking the door behind him. He would indeed complete the term paper this weekend, but he had another activity in mind as well, one that would require having the house to himself.

As he climbed the steps, Marty became more excited. His destination was not his own bedroom, but his parents'. As he entered, he went directly to his mother's dresser. He opened the top drawer and removed a bra and a pair of panties. In another drawer he found a camisole and half-slip. He took these items and laid them out on the bed. Next he went into his mother's closet and removed a powder-blue dress, which he also laid on the bed. He then removed a box from the top shelf. This box contained a wig.

Marty now turned to his mother's vanity. He slid open the top. To his relief, Mom had not taken all of her makeup with her. He removed a tube of lipstick and replaced the top.

It was now time for Marty to transform.

First, he removed all of his clothes. He watched himself in the mirror as he pulled on the silky panties with the lace trim, enjoying the feel of the soft material against his skin. Next, he hooked up the bra. He put it on backwards at first, hooking the strap in front of his chest, and then rotating it so the cups were now up front. He then slipped his arms through the straps.

Clad only in bra and panties, Marty now went to the linen closet in the hall. He pulled out some wash cloths and stuffed them into the bra cups. The result was rather lumpy, so he ran his hands over the cups to smooth them a bit.

He stepped back into his parents' bedroom to complete the transformation. He pulled the half-slip over his head and pulled it down until the elastic was at his waistline. All the while he watched in the mirror. Little things like the lace trim at the hem were exciting him. He pulled the camisole over his head, smoothing it as it clung to his bodice and bustline. He stopped once again to admire the more feminine image he presented in the mirror.

Delighting in the feel of the female undergarments, especially his boobs, he turned to remove the plastic dry-cleaner's bag from the dress. He removed the dress from its hanger and admired it. It was beautiful, with an empire waist and small pearls sewn into the bodice and around the hem. He unzipped it and drew it over his head, allowing the soft material to settle over the even softer cloth of the half-slip and camisole. He struggled a bit to pull the zipper completely up, but he managed. Once again, he paused to admire the results in the full-length mirror. His feminine side was emerging from its cocoon.

He sat down at his mother's vanity, pausing to smooth the skirt under his legs. He held his knees close as he sat. He removed the cap from the lipstick tube and applied the color to his lips. He paused a few times to press his lips together, spreading the color. Satisfied with the results, and enjoying the taste of his now red lips, he opened the wig box and removed the wig.

The wig was auburn, and it was big. Curls seemed to tumble over Marty's head as he pulled it on. He fussed with it to try to get its shape right. Then he stood and returned to the full-length mirror.

He saw a girl staring back from the mirror, and the girl was he. Or, more correctly, she. Now was that unique moment of transformation, when pronouns shifted gender. In Marty's mind, she was now a girl.

She vamped in front of the mirror, wiggling her tush in an exaggerated manner. She giggled as she walked back and forth. She would have liked a few more things to make her look complete, such as stockings and high heels, but these things were not available. Mom's shoes were just too small for her feet.

Marty now went to her own bedroom and removed a battered cardboard box from her closet. This held an ashtray, butane lighter, and a half-empty pack of Virginia Slims. Buying the cigarettes had been a particularly daunting task. Not only did she have to find a store that wasn't enforcing the age limits on tobacco, she also had to buy a pack of ladies' cigarettes while in boy mode. Fortunately, the store clerk didn't bat an eye and just took the money in exchange for the smokes.

She removed one of the cigarettes from the pack and held it between two fingers. She posed in front of the mirror, holding the cigarette at what she thought was a sophisticated angle, placed the cigarette in her lips and lit it. She watched herself as she drew the smoke into her mouth. She inhaled, coughing a little as the harsh fumes irritated her throat and lungs. Ignoring the cough, she took another drag, exhaled, and grinned. There were now lipstick marks on the filter.

She gathered up her cigarettes, the ashtray, and her lighter and descended the steps. She placed these items on one of the end tables and proceeded to walk back and forth in the living room, affecting a very exaggerated wiggle and holding the cigarette, pausing for an occasional puff. Oh, how sexy she felt, vamping around with the house to herself! It was so wonderful!

Marty's reverie was interrupted by the sound of a key in the front door lock. She stared, frozen in fear, as the door opened and her mother entered!

* * * * *

Kate felt so stupid! She and Dave had nearly gotten to the turnpike entrance when she realized she had forgotten her insulin. She wouldn't really need it until later in the day, and probably could have gotten it at a pharmacy in Ocean City, but her insulin kit also had her blood glucose monitor in it, and she really needed to test herself when they arrived. Dave did not complain about turning around to return home. He fully understood his wife's need to control her diabetes.

The first thing Kate noticed as she opened the door was the odor of cigarette smoke. It assaulted her nostrils! Was Marty smoking? How could he do this after all she and Dave had…

Then she saw Marty, wearing her blue party dress, holding a cigarette!

At first Kate was too stunned to speak! "M-M-Marty?" she managed to stammer.

Marty was now desperately wishing he could somehow vanish. He had been caught! His mouth opened, then closed, then opened, all without producing a sound. His eyes scanned the room furiously, searching for a possible escape route.

Kate managed to get out a few more syllables. "Just what is going on, here?" she said.

"Mom," Marty said, "I can explain! Honest, it's not what you think!"

"Dave!" called Kate, beckoning to her husband, "there's something you need to see in here!"

Dave came into the front door. The sight of his son in a dress and wig startled him, but the cigarette really ticked him off. "Marty," he said, with some anger in his voice, "put that damned thing out right now!"

Marty stared at the cigarette in his hand. He had almost forgotten it! The ash was now nearly an inch long. "Yes, sir," he mumbled, stubbing out the cigarette.

"Now get upstairs and get changed, mister. We'll talk about this when I've cooled down enough to be rational."

Marty slowly walked up the stairs to his room. Damn! he said to himself, how could this happen? Why the hell did they have to come back? I was supposed to have the place to myself! He started removing the wig, the dress, and the undergarments. He used some tissues to take off the lipstick.

He had finished dressing in his own male clothes when his father knocked on the bedroom door. Marty said, "Come in, Dad," doing a really poor job of hiding his fear.

Dave entered. "Sit down, son," he said, "we have a lot to talk about."

Marty sat on his bed while Dave sat in the chair at Marty's computer desk. "Dad," said Marty, "I can explain…"

"Let me finish what I have to say first, then you can explain to your heart's content. But for now, I want you to listen."

Marty nodded in silent acceptance. He was expecting a really long lecture and a harsh punishment.

"Marty," Dave began, "I can't begin to tell you how disappointed I am in you. You know how your Mother and I feel about smoking. You know we hate the smell of those foul things! What ever possessed you to start smoking, son? Your mother doesn't smoke! Neither do I! And neither do any of your friends! Why? Just tell me why?"

"Well, sir," Marty said, feeling his cheeks begin to redden, "it's kind of hard to explain. I only smoke when I…well…when I wear a dress. It looks sexy. It feels sophisticated." He fell silent in embarrassment.

"I see," Dave said. "Marty, have you ever seen your mother smoke?"

"No, sir."

"Well believe me, son, your mom is probably the sexiest woman on earth. And she's the most sophisticated lady I have ever met. She doesn't smoke. Marty, there is nothing feminine or sexy about smoking. It's just disgusting!"

Marty's head was hanging in that shame. "I'm sorry, sir," was all he could say.

"Have you been smoking very long?" Dave asked.

"N-n-no, sir. Just for a few months. Actually, this is the only pack I ever tried."

"The only one?" Dave asked skeptically. "You mean you never tried smoking before this? Be honest, son."

"Well," said Marty, a little more embarrassed, "I did try once with some of the guys when I was eleven. But that was the last time. At least until…"

"I see," Dave said. "Marty, I really want to trust you, but your behavior today gives me cause to doubt your sincerity. I know I can't stop you from smoking when you get older, but I don't permit anybody to smoke in the house. Don't ever smoke in this house again. And until you turn eighteen, I don't want you smoking at all. Is that clear?"

"Yes, sir," said Marty.

"Don't think you're getting away scott free, mister. You are grounded for the next two weeks, and you'll spend those two weeks doing extra clean-up chores around the house. For starters, I'm going to have you shampoo the rug to get some of the cigarette stench out of it."

"Yes, sir," Marty repeated, accepting his punishment. He wondered fearfully about what would come next. He didn't have long to wait.

"There's another matter we need to discuss, Marty. Your Mom is very upset that you took things out of her dresser and her closet without permission. She feels as though you had no respect for her privacy."

This surprised Marty. He listened in stunned silence as his father continued.

"Marty, we try to respect your space. We trust you to do the right thing. We hope that the values we taught you and the example we set for you would be sufficient. We don't go searching your drawers or your closet, out of respect for your privacy and to show we trust you. Don't you think your mother deserves the same respect?"

"I guess I never thought about it that way, Dad," said Marty. He was a little puzzled. When was his father going to talk about the dress?

"Well please think about it. Our closets and dressers are private. We expect you to respect our privacy in the same way we respect yours. Is that too much to ask?"

"No, sir, it isn't."

"Very well. I'm not going to punish you for this, but I want you to think about it."

"Yes, sir." Marty was starting to worry. How was his father going to handle catching his son in drag?

"Now, do we have anything else to talk about, son?" asked Dave. His manner was not at all angry, just concerned.

"Dad, I can explain. It's not what you think!"

"Oh, really? Are you going to tell me that you aren't really gay, that you just like wearing dresses, that you get a kick out of seeing yourself as a girl? Am I getting warm?"

Marty's jaw dropped.

"I'll take your silence for a yes. I'll bet you like to giggle when you dress up. Or even cry. It's a lot easier to let these un-manly emotions out when you think of yourself as a girl, isn't it?"

Marty was so stunned, he could only shake his head in agreement. He managed to stammer out, "How- how- how did you know? I mean…"

Dave smiled knowingly, but a smile tinged with pain. "I know more about what you're feeling than you might imagine. Let me show you something, son." With that, Dave opened the photo album he had been holding and turned to a particular page. "Take a look at this, Marty."

Marty turned the book so he could see the picture of several women at a party. They were all nicely dressed, but there was something about them that just didn't seem right. It was that woman on the left. She seemed strangely familiar in a way Marty just couldn't place. What could it be? Then he realized it was her hair. It was auburn and done up in a style that looked exactly like Mom's wig.

He looked up at his father, then back at the photo. The woman's features were strikingly similar to Dad's. Wait a minute, could it be…?

"Dad! That's you! You're wearing Mom's wig!"

"It's not your mother's wig. It's mine."

Marty was once again stunned. "I'm a crossdresser, son," said Dave.

Marty started leafing through the photo album. It was filled with pictures of Dave in various feminine attire. Sometimes he was by himself, sometimes he was with other women, but in every picture he was dressed as a woman. "Marty," said Dave, "I'd like you to meet Wendy, my alter ego."

"Son, I'm going to ask you some questions. I know these feelings you are having are confusing. I just want you to know that no matter what happens, I love you, and I'm here for you. I'm not at all angry, and I just want to help."

Marty was still shaken. His emotions were on a roller coaster. "I don't know what to say, Dad. I just…" at this point Marty became aware of tears welling up in his eyes. He had always been afraid to cry in front of anybody, especially his father. Now he found it impossible to hold back.

Dave reached out and hugged his son. He felt Marty's tears as they soaked into his shirt. Marty was unable to speak. His tears flowed forth as he felt his father's strong, loving arms encircle him. It brought back memories of when he was a toddler and Dad would lift him up to the ceiling. He felt loved.

The emotional outpouring lasted for only a few moments. Marty soon composed himself. He knew he could tell his father about his secret, without any fear of punishment or of ridicule.

"Whatever you tell me, Marty, I'm not going to be angry. I just need to know a few things. For starters, how long have you been dressing up?"

Marty paused for a second, then said, "I guess it's been about a year now. But I wanted to try for a long time."

"How long?"

"I guess as long as I can remember. I always sort of wanted to try on some of Joanne's things, especially her party dresses. But I was afraid to. I thought…" he hesitated.

Dave finished for him. "You thought people would laugh at you, call you a sissy. You were afraid of being the outsider, of being rejected. Is that part of it?"

"Yes, sir. I was afraid."

Dave sighed. "How well I know that feeling. I thought I was the only guy in the world who wanted to wear a dress. Sometimes I wanted to be a girl so badly, I would even pray that somehow God would transform me. But then I was so afraid that I was some sort of faggot that I tried to bury that part of myself."

"Dad," said Marty, "that's exactly how I feel! How could this be?"

Dave smiled. "You aren't really so unusual. We've all felt the same thing, you know. We know that we're different, but we try to hide it. Even from ourselves."

"So tell me," asked Dave, "how did you feel the first time you wore a bra?"

Marty's cheeks began to redden.

"Don't be embarrassed, Marty. Remember, I've done this too."

"Well," said Marty, feeling his reserve fade, "it felt exciting. I don't think I ever felt anything as neat in my life. I felt so, so, so girlish!"

"Do you masturbate when you dress up?"

Marty felt a little panic. "Well. I guess so, but…"

"It's all right, Marty. That's a natural thing for a teenage boy to do. I masturbated regularly when I was your age, and often while I was crossdressed."

Marty was taken aback by this frank admission from his father. "Dad, do you still…"

Dave laughed. "No, not for a long, long time. Truth to tell, son, your mother and I enjoy a very satisfying sexual relationship. It's been a very long time since I used dressing up for sexual gratification." Dave smiled a very knowing smile.

"I need to know something, Marty. It's important for you to be honest. Do you ever feel like you should really have been a girl? I mean, to the point of wanting to change your sex?"

Marty considered his reply. "In all honesty, sure, I thought about it. But if I'm just as honest, I don't know if I want to be a girl permanently. I mean. It might be neat to be a real girl for a day or two, just to know what it's like. But I guess I like girls too much to want to be one."

"Are you still a virgin?"

"Uh, yes, sir. I haven't used the rubber yet." Marty was referring to the condom Dave had given him when they had "The Talk".

"I see. Do you like the idea of having sex with a woman?"

"Well, sure, Dad!" Marty said emphatically.

"How about the idea of sex with a man? You can be honest with me."

"Gee, Dad, I mean, sometimes I think about it, but only if I was, you know, a real girl. I'm not a Homo or anything like that."

"I see. So the idea of getting your penis cut off to become a woman doesn't exactly appeal to you?"

"Oh God, no!" Marty protested. "No way!"

"Don't get so excited! I'm not going to castrate you, Marty, I'm just trying to figure out how exactly you fit in the transgendered universe."

This was the first time Marty had ever heard that word. "Transgendered? What's that?"

"It's what you are, son. And it's what I am. Our gender identity doesn't quite match society's expectations. It's a label that includes a lot of people, from crossdresser to transsexuals and everybody in between.

"Marty, there's something I want you to realize. There is nothing wrong with you. You are neither crazy nor perverted." Dave tone became somber. "I remember hiding my true nature from everyone, even from myself, for years. The constant denial led to a lot of bottled-up anger. I was afraid!"

Dave turned to his son and clasped his hands on Marty's shoulders. "Marty, I don't want you to ever feel that there is anything wrong with being transgendered. Don't believe for one second that you are any less of a man just because part of you is a woman. You are my son, you are beautiful, and I love you." It was now Dave's turn to cry.

Marty watched the tears form in his father's eyes. Dad had always been so strong for him. Now to see his father cry, to know that this strong man was also sensitive and vulnerable, made Marty love him all the more. He hugged his father, returning all the years of love Dave had given him. At that moment, father and son bonded more deeply than ever.

The tears soon stopped. Neither man was embarrassed. The only thing they felt was love.

"Dad," Marty asked, "did Mom know about it? I mean, like, before you got married?"

"No, she didn't. I was still hiding Wendy from the world and myself when we got married. I tried to suppress my feminine self for years. I would tell myself that as long as I was not actively dressing, I wasn't a transvestite. I almost fooled myself into believing it, too. But it was hell.

"After a few years of this, I started trying things on again. It would always be 'just one last time'. But it never really was the last time."

Marty asked, "Does Mom know?"

"Yes, she does. She actually realized it before I did. At least, she knew something was bothering me. But when I finally told her, she was shocked. It took months for us to talk about it, and years to work it out."

"So what does Mom think of it now?"

Dave sighed again. "She's not exactly crazy about it, but she's not afraid. Sometimes I dress for her. She's come to think of Wendy as a kind of girlfriend."

"What about the pictures, Dad? Where are they from?"

"Those pictures were taken at my support group. There's a bunch of us who get together to try on new clothes and socialize a bit. Mostly, it's nice to know that we aren't alone, and we can let our feminine side out without fear."

"So those were other guys in those pictures?"

"Mostly. Some of my friends bring their wives to the meetings. Your mom has been to some of our parties and seems to like them."

"Wow, that's really great, Dad." Marty paused, wondering whether to ask this next question. "Dad, do you think that maybe I might be able to go with you some time?"

"I don't see why not. But most of the girls there are about my age. You'll be the youngest girl there."

It was at this moment that Marty realized he was going to be accepted as a girl. The thought frightened him. It also excited him. "Do you mean it, Dad?"

"Yes, I do. I want you to accept this part of yourself, to adjust to it. I don't want you to be ashamed, or to live in fear. I don't want you to go through the hell I had to endure."

There was a knock at the door. Dave opened it to let Kate in. "So how did it go, you two?" she asked.

"Everything's all right, honey," Dave said. "It seems that Marty and I share a gender gift."

Kate looked at her son lovingly, but with some pain. She hugged her son in that special way mothers always embrace their children. "I'm not mad at you for this gender thing, Marty. But please, don't ever smoke again. I don't want my boy to get addicted to those things. Promise me you'll never do that again?"

"I promise, Mom. I'm really sorry. I just…" tears began to flow again, as Kate kissed her son's forehead.

"Mom, Dad," Marty said, "I'm sorry I ruined your weekend. I never wanted to hurt you."

"The weekend isn't over yet," Kate said. "I think we can still make it to Ocean City. I'll just have to get my meal and take my insulin before we leave. So how does some dinner sound?"

Marty had totally forgotten about food. Now his stomach asserted itself. "It sounds great, Mom!"

"Good. Let me throw some food together and we can eat. At least I know you won't be eating pizza for supper!" Kate opened the door, then turned. "Marty, I have an idea. Why don't you dress for dinner?"

"Dress?" Marty asked, "what do you mean?"

"Wait here," Kate said. She returned with a skirt and a blouse. "These were Joanne's. We were going to give them to Goodwill, but now I think we'll keep them. Do you want them, Marty?"

Marty couldn't believe it! "Yes, I would! You mean you…"

Kate smiled. "Go ahead, put them on. You can get dressed while I fix dinner." She left the clothes with Marty and went downstairs.

Marty stared at the clothes in disbelief. Dave smiled and said, "Well, what are you waiting for?"

"I don't know! I never expected this!"

"Come on, son, let me help you with your transformation."

* * * * *

It wasn't a lavish dinner, just something pulled together from the freezer, but it was still good. Chicken breasts with baked potatoes and green beans made a good family meal. Kate had just put it on the table when Dave entered the kitchen.

"Just in time," Kate said. "Is Marty ready?"

"I think so," said Dave. "Kate, may I present to you Marty's alter ego, Melissa."

Melissa entered, wearing the teal skirt and blouse Kate had given her. Dave had provided breastforms for her bra, pantyhose, and a pair of mid-heeled pumps. For now her legs were relatively hairless, but Dave promised to show her how to shave them when it became necessary. Some powder, blush, eye makeup, and lipstick completed the effect. Melissa felt absolutely feminine.

Kate smiled approvingly. "Very nice. Melissa, is it? Well come here and give you mother a hug., Melissa. And welcome to the family."

They hugged, and then the family sat down to dinner.

 © 1999 Valentina Michelle Smith

Notes:

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