The Masks We Wear

Published on Aug 21, 2022

Gay

The Masks We Wear 1

R The Masks We Wear R

by tim the story guy

This story is © 2007 by tim, and is protected by copyright law. Please do not copy to distribute, or post to other sites without the author's permission. This is a fictional story. Any similarities to actual people or events are purely coincidental. This story contains sexual situations involving teen males. If this subject offends you, or you should not be reading this type of story, you assume all responsibility for continuing. Please send all comments to: timthestoryguy@yahoo.com. Also, please visit my web site at: www.timthestoryguy.com. My stories are always updated there first, and it contains works from other authors and interactive features, as well as my Presidential campaign. The title fonts are a combination of Impact, which is a standard Windows font, and DramaAndCo, which can be downloaded at www.dafont.com. The text font for this story is Sanford, which can also be downloaded at www.dafont.com. Thanks, and enjoy the story.

Stories on Nifty by tim the story guy:
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Doctor Bechtel - in the adult/youth section (Last update 01/12/07)
Never Too Old, Never Too Young – in the adult/youth section (Last update 08/19/07)
Physical Attraction - in the adult/youth section (Last update 01/19/07)
Training Day - in the adult/youth section (Completed 09/17/04)
What A Gas! 1, 2, & 3 - in the adult/youth section (Last update 08/11/07)
Interplanetary Incident – in the sci-fi/fantasy section (Last update 08/20/07)
Orgasmia 1 & 2 - in the sci-fi/fantasy section (Last update 07/25/07)
Sweet Sixteen - in the sci-fi/fantasy section (Book 1 finished 01/14/07. Story will continue with Sweet Sixteen 2: Seventeen and Beyond.)
Time To Go (special preview) - in the sci-fi/fantasy section (Preview completed 08/28/06. I have added Chapter 3 to the preview because I feel that it's a much better chapter to finish the preview with. The entire book is still available, and info can be found on my web site.)
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Fate - in the high school section (Last update 02/06/07)
No One Else 1, 2, & 3 - in the high school section (Last update 08/08/07)
Starting Over 1, 2, & 3 - in the high school section (Last update 07/31/07)

The Masks We Wear

by tim

Chapter 1

Bobby Billings was an average fifteen year old boy, who would be turning sixteen tomorrow. He was excited, because he knew his parents had been planning his sixteenth birthday party for about a month now. He was also excited that his girlfriend Alexandra, who would turn sixteen a week later, would be a big part of his sixteenth birthday. The reason for that was that even though Bobby and Alexandra had been dating for over a year now, they were both still virgins. There was nothing wrong with being a virgin, but Bobby loved Alexandra very much. He wanted to show her that love too, but had never gotten anywhere with her. Of course they had kissed, which they had actually done quite a bit. Bobby loved the feel of his lips against Alexandra's, and the feel of his tongue inside her soft mouth. Whenever he tried to feel her breasts though, Alexandra would push him away. Once he almost got his hand up her thigh, and to her panties, but Alexandra became visibly upset by that.

This time Bobby had a plan though. He was going to play on it being his sixteenth birthday, and explain his undying love for her. He would tell Alexandra that there could never be anyone in the world that he could love as much as he loved her, and he wanted them to share their most intimate love for each other on his sixteenth birthday. After all, he had let Alexandra feel his maturing cock through his pants on several occasions. Once he even let her remove it from his pants and stroke it. Then Alexandra wanted to take it into her mouth and make love to it, but Bobby had insisted that they could only do that if she would allow him to make love to her too. At that point Alexandra became upset, and gently tucked Bobby's cock back into his pants for him.

This was becoming important to Bobby because he and Alexandra had been friends since they first met in Kindergarten. As their friendship grew over the years, so did Bobby's love for Alexandra. Alexandra was a very pretty girl as far as Bobby felt. Her skin was as smooth as silk, and as fair as anyone he had ever seen. She had the softest and most beautiful features Bobby had ever seen. And she also had a very petite and girlish figure. Bobby knew why his love for Alexandra had grown so strong over the years. She was without any doubt the most perfect girl in the world.

Alexandra loved to play the game too. She was constantly admiring Bobby out loud to her other friends, telling everyone how masculine and attractive her friend Bobby was. She would eat Bobby's flirting up, especially if her other friends were around. When Bobby asked her to be his girlfriend, Alexandra agreed immediately. She wasn't just teasing Bobby, she really did love him. She wanted to be with Bobby forever more than anything else. Their relationship would have to stay the way it was right now though. Alexandra knew that things could never go beyond the kissing they shared, and that soon the hugging would have to be cut out. Whenever Alexandra started going through this, it was hard for her not to curse her parents for causing her the pain she felt. She also knew that things would be coming to a head soon, as she prepared herself for Bobby's sixteenth birthday party the next day.

“Bobby, get up!” yelled out Bobby's mother Beth, from the bottom of the stairs. “Do you still need me to run you over to Alexandra's house, to pick her up for the party?”

“Yeah mom, I'll be right down!” replied Bobby, as he blinked the sleep from his eyes.

Bobby got out of the bed, and threw on a pair of boxers. Then he went over to the full length mirror to look at himself. Bobby had a morning erection, which was due to him not having relieved his bladder yet. He looked down to where his cock was poking out of the fly of his boxers, and said, “Take it easy my friend. I'll take care of you in a minute!” Bobby called his circumcised cock his friend because he liked it a lot. At six and a half inches erect and still growing, it gave Bobby something to be proud of. He knew he wouldn't be the most well-hung guy in the world, but eight inches didn't seem out of the question a few years down the road, and that thought made Bobby happy. Then Bobby looked at himself in the mirror.

“Happy birthday.” said Bobby to his reflection.

Although he sometimes had a hard time accepting it, he could see why others thought he was handsome. He had light brown hair that he kept at just the right length, and eyes that were almost tan. He also had a narrow but not skinny face, a perfect button nose, full but not thick lips, clear skin, and a dazzling white smile. He was even starting to get a hint of fuzz over his lip and on his chin.

“Damn, I already shaved once this month!” laughed Bobby, as he rubbed his chin. “Oh well, maybe Alexandra will find it incredibly sexy!”

Bobby then went into his bathroom, relieved his bladder, and brushed the morning taste out of his mouth. By that time his cock had softened, and retreated back into his boxers. After a quick shower, Bobby went back to his room and got dressed for the day. Then he headed down the stairs for breakfast.

On the way to Alexandra's house, Beth said, “I like it that you and Alexandra seem pretty serious son. She seems like a sweet girl, even though her parents are a little stand-offish.”

“You've noticed that too huh mom?” replied Bobby. “Oh well, I'm in love with Alexandra, not her parents.”

“I can tell!” snickered Beth. “I know you're growing into a man quickly now son, but remember not to take things too quickly with Alexandra, okay?”

“Does every teenage boy get that talk from his mom?” laughed Bobby. “How old were you and dad when you... you know?”

“Nevermind that young man!” replied Beth, as she tried not to laugh. “We were both ready, and that's what matters.”

“I thought so!” snickered Bobby.

When Alexandra came to the door, she was wearing one of the most beautiful dresses Bobby had ever seen. Bobby yelled back to the car, “Mom! Call the people at Miss America and tell them we have the winner here!”

That made Alexandra blush slightly, which Bobby thought made her look even more beautiful. The fight with her parents over something to strap around her chest to fill her out was worth it though, as it really seemed to please her boyfriend now. As Bobby led Alexandra back to his mother's car, Alexandra's parents watched discreetly out the window. They dreaded this day, and knew Bobby would hurt Alexandra by the end of it.

Bobby's sixteenth birthday was shaping up to be the best day of his life. Not only did he have a beautiful girlfriend there, who all of the boys seemed jealous over, but he also had plenty of good friends there. Bobby's parents had saved for years for this day, and presented their son with his own car. Then Alexandra gave Bobby her present. Bobby opened the small box to find a silver chain with a silver heart attached to it.

“Read the back.” said Alexandra.

“Alex and Bobby.” read Bobby aloud. “Alex?”

“Yeah, Alexandra never would have fit.” blushed Alexandra.

“It's beautiful, and I love it!” said Bobby, as he put the necklace on. “I love it as much as I love you Alexandra.” Then Bobby leaned into her ear and whispered, “And I'd love for us to go to my room when the party dies down.”

Once the party began to die down, Alexandra did follow Bobby to his room. Then Bobby and Alexandra sat down on the side of his bed, and Bobby said, “You look very beautiful today Alexandra. You know I love you very much, and today only makes me love you even more. No one can make me feel the way you do when we're together, and I'll love you for the rest of our lives. Just looking into your eyes makes me want to share everything with you, including all of the love we share for each other. I have a lot of love I want to share with you Alexandra, and nothing will ever change that.”

Alexandra was now prepared to give in to Bobby. They had known each other their whole lives, and Bobby deserved to know even more on this day. He had to know everything before their relationship went any further.

“I hope you're right Bobby, because I love you just as much.” replied Alexandra.

Bobby laid Alexandra back with himself on the bed, and met her lips passionately with his. Bobby put as much love as he could into kissing Alexandra, because there was so much more that he wanted to share with her. Then Bobby was thrilled when Alexandra let him hold her closer. Bobby pressed his chest into Alexandra's breasts tightly. It didn't feel exactly like he imagined it would, but he loved the contact anyway. The tight embrace and passionate kiss then encouraged Bobby to go further. Bobby reached down and placed a hand on Alexandra's smooth thigh, and began to massage it. This time as Bobby made his way under her dress, he felt no resistance from Alexandra. Bobby inched closer and closer, as his breathing became more shallow. Bobby slipped the tips of his fingers underneath Alexandra's panties, and Alexandra submitted to him willingly. Then Bobby slipped his hand in and felt... Alexandra's stiffening dick!

“What the hell!” shouted Bobby, as he snatched his hand from underneath Alexandra's dress quickly. Then he looked at Alexandra with a combination of shock and fear in his eyes, as he backed away slightly. “What the fuck is going on here?!” asked Bobby in a confused tone. “You have a dick!”

“Please Bobby!” pleaded Alexandra.

“Please what?!” asked Bobby, with a bit of anger and betrayal in his voice. “We've been friends since Kindergarten, and you've been a boy all this time? Why would you do that to me Alexandra?! I mean Alex. I mean,... who are you anyway?”

“The name on my birth certificate is Alexander.” replied Alexandra in shame. “Please don't hate me until you give me a chance. Then if you never want to speak to me again, I'll understand.”

“Okay... Alex, I guess.” replied Bobby. “Explain to me why you've lied to me all these years, and even let me fall in love with you, knowing you were a boy!”

“Okay, here goes.” said Alex. “Before I was born, my parents were convinced they were going to have a girl. When my mother first started delivering me, they said I even looked like a girl from the waist up, and they were very happy. Then they were shocked to see that below the waist, I had a penis. They even said they ran tests on me, and said I should have been a girl. At that point it was decided that I was too feminine to be a boy, so I would live my life as a girl. When I was old enough to talk and understand things, it was drilled into my head that I was a girl. My aunt told me most of this, because she was around the most and said my parents were really screwing up my head. My aunt also told me that my parents had threatened me on several occasions to either act like a girl, or they would have my dick removed surgically, then have the doctor turn me into a girl. When I entered Kindergarten, the name Alexandra was so close that my parents snuck it in, and the school let it slip past them. From that day on, I was warned never to say the name Alexander again. When we became friends, I was so afraid of my parents that I let you believe I was a girl. Then later on, I was afraid the truth would ruin our friendship. As we grew up, and my parents conditioned me to live as a girl, I actually started believing it. I fell in love with you because I really believed I was a girl. I hate my parents for what they've done to me!” Then Alex began to cry heavily, wreaking with heavy sobs.

“We were friends Alex.” said Bobby, not knowing what to think. “You could have come to me at any time, and I would have understood.”

“No one can understand me Bobby!” cried Alex. “My parents turned me into a freak, and now everyone will hate me! I wouldn't even know how to be a boy! I hate them so much Bobby!”

“I promise I'll try to understand Alex, and I really don't hate you.” said Bobby, as he carefully moved closer and put an arm over Alex's shoulder.

“Bobby, I'm a boy, and I just admitted that I love you!” cried Alex. “I know you thought I was a girl, and I know you're not ready for a boy to be in love with you! I know you'll hate me!”

“Alex, you even said yourself that you had been convinced you were a girl.” said Bobby, now trying to comfort Alex. “You felt like you were a girl, falling in love with a boy. It wasn't your fault. How can anyone's parents do that to them?”

“I really wish I knew Bobby!” replied Alex, as he began crying into Bobby's shoulder and chest.

Bobby let Alex cry for a while. Then Bobby didn't know why, but he put both arms around Alex. Pretty soon though, Alex's crying began to let up. Alex finally stopped crying, straightened upright, and looked into Bobby's face.

“Are you sure that you don't hate me Bobby?” asked Alex.

“I'm sure.” replied Bobby.

“Does that mean we're still friends?” asked Alex.

“Of course we are.” replied Bobby. “You look like you really need a friend now.”

“Can we pick up where we left off?” asked Alex.

“Don't push it Alex!” replied Bobby, as he smiled.

“It's no wonder I fell in love with you Bobby.” said Alex. “I even wore this dress just for you.”

“It is a pretty dress Alex, thanks.” said Bobby. “I'm still confused about how to handle the fact that we're dating. I'm not gay, but I've already dated you, and I liked it.”

“I really am sorry Bobby.” said Alex.

“Okay, you said that you wouldn't know how to be a boy, right?” asked Bobby.

“Yeah, so?” asked Alex.

“Then just stay a girl until we figure this out.” said Bobby. “I mean, if you started being a boy, and we were still friends, it might look kind of weird. Besides, when I kissed you with you like you are now, it felt kinda nice.”

“Would you kiss me again then Bobby?” asked Alex.

“I can try.” replied Bobby.

Bobby put his lips back against Alex's, and they felt exactly the same as they had before. Bobby then began kissing Alex the same way he had before. Bobby forgot all about Alex being a boy, and kissed him like he was still kissing his girlfriend. That kiss meant more to Alex than anything anyone had ever done for him.

Once the kiss was over, Alex gasped, “I still love you Bobby!”

“I don't know about love Alex, but you just felt the same way you did before.” replied Bobby. “This is really very confusing. I promise though that we'll deal with your parents for what they've done to you. You should have been allowed to be who you were.”

“Would you have still fallen in love with me Bobby?” asked Alex.

“I'm not sure about anything anymore Alex!” replied Bobby. “We're still friends though, and I'll stick by you Alex.”

“Thank you Bobby.” said Alex. “I've always imagined this day turning out so bad, and you've helped it hurt a lot less.”

“Isn't that what friends do?” asked Bobby as he smiled. “And by the way, I don't know if I'll ever be ready for anything else, but I really would like to kiss you again sometime.”

“Anytime Bobby!” replied Alex as he smiled.

“Now, what do we do about us?” asked Bobby.

“How about just keeping everything like it was before we came up here?” asked Alex.

“I guess we could try that, although I hope no one asks too many questions yet.” replied Bobby. “I know my mom will though. She can be pretty nosey when she wants to be.”

“And my parents are sure I'll be destroyed by what happened today.” said Alex.

“That one is easy!” said Bobby. “Just tell them that you had the best time ever today!”

“With you still as my friend, that's not too far from the truth.” replied Alex.

“Good, that'll bug them even more!” laughed Bobby. “They deserve it after what they've put you through! I still wish you had told me though. We were best friends, and I really did fall in love with you.”

“I'm sorry Bobby, and you deserve better than me.” replied Alex.

“Please don't say that Alexandra... I mean Alex.” said Bobby. “Man, this is going to take some getting use to, especially with you wearing dresses.”

“It's the only thing I've ever known.” replied Alex. “I love being a pretty girl, and dresses make me pretty.”

“For what it's worth, you are a very beautiful girl Alex.” replied Bobby. “You really had me going for you. Exactly how much boy and how much girl are you anyway?”

“I have a dick and balls, and that's about as much boy as I am.” replied Alex, a little uncomfortably. “I don't have the hormones to grow hair anywhere on my body, except the top of my head.”

“You've never had any body hair at all, even under your arms or around your dick?” asked Bobby.

“From the head down, I'm as hairless as the day I was born.” replied Alex. “The doctors kind of expected me to grow breasts, but thank God that hasn't happened yet.”

“Yeah, I guess that would screw things up more than they are already.” said Bobby. “Don't worry Alex, we'll find a way to straighten all of this out somehow. I couldn't turn my back on you considering how you've been treated your whole life.”

“Thanks Bobby, you've been nicer to me than anyone else in my life.” said Alex. “It's no wonder I fell in love with you. It's just too bad you can't still love me the same way.”

“I'm not gay Alex.” replied Bobby. “We can be best friends, and heck, we can even kiss really nice sometimes, but I can't do the things you'd want to do to me. I don't even know if I could let you do those things to me now, knowing you're a boy. I fell in love with the prettiest girl I know, but now I know you're a boy. I still have special feelings as friends toward you though.”

“I understand Bobby, and I really am glad you're still my friend.” replied Alex. “Most of the dreams I've had about this moment involve you hating me for the rest of your life.”

“Does this look like I hate you?” asked Bobby.

Then Bobby leaned over and gave Alex a warm and sweet kiss on his lips. It was brief, but it was enough for Alex. “I may not love you the same way I loved Alexandra, but I still love you as a friend Alex.” said Bobby. “Now, I think we better get back downstairs before everyone starts worrying. And remember to let your parents know that you had a great time. I'll stick with you as friends, and we'll figure out what to do.”

“Your friends all told me to tell you they had a great time Bobby.” said Beth, as Bobby and Alex came back downstairs. “So, did you and Alexandra have a good time?”

“It was interesting mom.” replied Bobby.

“interesting?” laughed Beth. “I don't think I've ever heard it described that way before!”

“Mom?! What do you think we did?” asked Bobby. “I decided you were right, and we shouldn't rush into anything!”

By this time Beth was turning six different shades of red, and Alex was having a hard time not snickering.

“I'm sorry Bobby, I just thought...” started Beth.

“Don't worry mom, it's okay.” said Bobby. “I probably would have thought the same thing. I guess I better break in the new wheels, and take Alex... andra back home.” Bobby sighed inside, over catching his near slip.

On the ride back to Alex's house, Alex slowly slipped his hand onto Bobby's thigh as they talked. He couldn't believe it when Bobby didn't remove it right away. Bobby finally pulled over around the corner from Alex's house.

“You know I'm not gay Alex.” said Bobby. “Why are you rubbing my thigh like that?”

“Because I've always liked doing it Bobby.“ said Alex, as he continued to massage Bobby's thigh warmly. “If you want me to stop, just take my hand off your thigh, and I won't do it again.”

“I can't, it feels too much like Alexandra's hand.” replied Bobby shamefully.

“That's because it is Bobby.” said Alex. “The only thing that's changed is that you know the truth now. And if we're still going to be friends as far as everyone else is concerned, they're going to think that it's strange if we start acting differently.”

“Oh crap, you're right Alex!” replied Bobby.

“Are small shows of affection like this so bad that we should get caught over stopping them?” asked Alex.

“I guess I'm going to have to get use to thinking differently, huh?” said Bobby.

“I do still love you Bobby, but I'm not going to try to turn you gay.” said Alex. “No one can turn anyone gay. I don't even consider myself gay. I think of myself as a normal girl, in love with the greatest boy in the world.”

“I guess I have to do some thinking about that.” said Bobby. “That's what trapped you into believing you're a girl isn't it? The fear of being caught.”

“That's a part of it.” replied Alex.

“I'm understanding more all the time.” said Bobby. “Do you want another kiss before I take you home to face the parents?”

“I'd have to be stupid to ever turn down a kiss from you Bobby!” smiled Alex.

Bobby put his arms around Alex, and pressed their lips together. Bobby knew that it felt no different than when he thought Alex was Alexandra, so Bobby began kissing Alex passionately. Then his tongue instinctively pushed into Alex's soft and warm mouth. Then Bobby's and Alex's tongues caressed each other for the next few minutes.

When Bobby finally broke the kiss, he said, “It feels exactly the same Alexandra. You ARE more Alexandra than Alex, aren't you?”

“It's all I know Bobby.” replied Alex.

“Well, we'll talk about it more when I pick you up for the movies tomorrow.” said Bobby. “I guess we wouldn't want to change that suddenly either, would we?”

“You DO treat me much better than anyone has before Bobby.” replied Alex. “I can't wait for our date tomorrow!”

As soon as Alex walked in the door, his mother said, “Oh, I'm so sorry honey. We knew this day would come, but there was no way we could stop it either. We'll help you get over the hurt you must be feeling.”

“I have no idea what you're talking about mom.” replied Alex. “I had a great time at Bobby's party, and he's the greatest friend in the world. He'll be stopping by as usual tomorrow, for our usual movie date. Now I'm going to have a hard time showing Bobby a better time at my sixteenth birthday party. It was still the best day of my life though.”

Alex's parents didn't know what to say to that, and it almost made Alex burst out in laughter. Later that night In Alex's dad Ernie's room though, his parents were in no mood to laugh. Alex's mom Beverly had stopped by her husband's room to talk.

“I would have been sure Alexandra would have told Bobby about herself today.” said Beverly. “After all, it was Bobby's sixteenth birthday, and they've been dating for a while now.”

“Maybe she didn't dear.” replied Ernie. “You know how closed mouthed kids can be, especially Alexandra. Most times we have a hard time dragging two words out of him... I mean her.”

“Oh my God Ernie!” exclaimed Beverly. “What if she did, and that Bobby boy likes the idea of her having boy parts?!”

“That would be a disaster, wouldn't it?” replied Ernie. “We may have to keep a close eye on those two when Alexandra has her birthday party next week. And those boy parts you talk about have names. They're a penis and testicles.”

“Don't you have that kind of talk with me Ernie!” scolded Beverly. “You know I'm not in the mood for that kind of filth!”

“Yes dear, I know.” replied Ernie.

The next day was Alex and Bobby's weekly movie date, except that it used to be Alexandra and Bobby. Alex had a hard time convincing Bobby to hold his hand in public, but Bobby finally started getting used to it. The one thing Bobby didn't need too much encouragement for was kissing Alex during the movie. It still felt just like kissing Alexandra, and Bobby liked how that felt. They did talk more about how Alex's parents treated him, and about what they were like. Bobby thought it was creepy when he found out that Alex's parents never slept in the same bed anymore.

Over the next week, Alex's parents never let on to their concerns. Alex and Bobby tried to carry on as though nothing were different now, but Alex had to talk to him about it a few times. Bobby was still very confused about the whole thing, and about exactly how he should feel about pretending Alex was still a girl. Alex was keeping his word though, and not pushing Bobby into anything sexual. The only things they did were things that showed affection, which their friends had grown to expect from them.

Finally, the day of Alex's sixteenth birthday party came.

There we have Chapter 1 everybody. Doesn't Alex's parents make a cold chill run down your back? lol. This story won my most recent poll by a wide margin, so I hope you enjoyed it. Please send all comments about the first chapter to: timthestoryguy@yahoo.com and let me know how you like it. Also, don't forget to visit me at: www.timthestoryguy.com. Thanks for reading, and I hope to see everyone in Chapter 2.

Next: Chapter 2


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