You know the usual rules, you should not be here unless your 18. Go away otherwise, because if you don’t, well someone might find out about your little problem and confront you. Maybe you’ll get what you have always wished for. You know what you want, to be girl, or dress like one or maybe get that cute pink satin dress with white tights and Mary Jane’s.

Unfortunately this story is a product of my imagination and not true in any way shape or form. I have taken parts of my own life to throw in a bit here and there. I hope you enjoy this story as much as I did writing it. This story was graciously edited by Elen. Coming very soon, My Life in a Dress, part II. Comments are always welcome. Email me at [email protected]. Flames will be ignored and purposely deleted on receipt.

Prolog:

I have a problem and I need to tell someone. So here you are dear reader, I need to use you to pour my heart out and I’ll use your shoulder to cry on metaphorically. I guess I should start with who I am. Well my name is Mathew. I’m 14 years old and a skinny 5’3”, dirty blond hair, and hazel eyes. I am your average boy, and I like all boy stuff, I’m doing great in school, have plenty of friends, and I am not bullied at school. I also have a girlfriend Karen; she’s a gorgeous brunette with emerald eyes, and is 5’2”. I share my time with her with my best friend Josh who is also 14. He is 5’5” with brown hair and green eyes. All three of us hang out together all of the time. I don’t mind having a third wheel and neither does Karen. So what’s the problem you ask? I have good grades, a girlfriend and I’ve known her since we were nine and best friends since we were in diapers. Well I guess that’s why I am here, to tell you all about it. My problem is that I’ve started to have feelings for Josh. Don’t ask me why, but they’ve become stronger over the last year and even stronger after what has happened. I can’t believe that this could have happened to me. Not Matt. I can’t be gay, bi or whatever. I mean I have always been in love with Karen. We’ve done things together I would never do with Josh. Josh and I have been best friends since we could crawl but you should know best friend and girlfriend relationships, well they’re different. For me, it’s much different than you could possibly imagine. Well, I guess since you got this story off of Big Closet, you probably know what the gist of the story is going to be about. Don’t you girls? I guess I shouldn’t make you, dear reader, wait any longer. Yes of course I am a cross dresser. You should know that by now at least. And I thought all you authors and fans were smarter than that. Boy, what was I thinking? You don’t care do you? Why should you? You don’t even know me. I’m just some guy out in nowhere land typing a story for your enjoyment.

Wait; please don’t go I was just trying to be funny. I’m sorry, forgive me. Ok, thank you for continuing. I have a few acknowledgments to make first. They’re for a few of my favorite authors out there. Why you ask again? Because this is my story and I can, that’s why. If your story is listed here, I thank you so very much. Your stories helped me to find who I am and what I want.

Show Me The Money: By Arecee - Please don’t stop writing this story.

The first week of my life/the second week: By Amanda Louise - You left me hanging at the second week.

Standing Up to Life by: Tiffany Shar — You too girl, please finish.

I love you guys.

AND NOW:

Matt’s Dilemma

By:

Sara D.

Ok, so I left you hanging at my problem. I love two people, and they are both my friends, one’s a boy and the other is a girl. I know I have feelings for both of them. I get that butterfly feeling in the pit of my stomach every time I am with them. I know it’s not just one or the other. How you ask? Well, I get that feeling whether I’m with Karen alone or Josh alone. Hence, my problem. Do I tell them how I feel? Karen knows how I feel. God, I must tell her ten times a day that I truly do love her. But after what happened today, I am pretty sure Josh knows how I feel. Crap, I just about jumped him while we were in his room earlier. I’m not 100% sure because I ran home, threw myself on my bed, and started to cry. I haven’t cried for years. What the hell is wrong with me? I need to talk to someone. Maybe my Mom. But that’s not likely to happen. I don’t think I’m ready for that discussion with her yet. I mean she’d understand about my feelings, I’m sure. But, how the hell do I talk to her about my feelings? It would be too awkward.

I could call Karen and explain things to her. We already share a pretty big secret already anyway. Just to bring you up to date I’ll tell you. IT’S ALL KARENS FAULT! Well sort of. I never really complained at any point while this occurred. I guess it all started when Karen moved in next door. Josh and I were both nine. We were playing outside with our bikes when an angel came out of the back of a moving van we had watched drive up an hour ago. We were loitering around the truck for about 15 minutes to see who was moving in. I immediately fell for this girl. I should have put my bike down on the sidewalk next to the grass separating our yard from hers, and do the gentlemanly thing. Introduce myself and offer to help her with a box. Of course, I didn’t do that. I was nine. Both Josh and I were too nervous to talk to her and rode off on our bikes to the park. Sorry, I’m a boy, that’s what we do. I was never feminine at this point in my life. I just knew I liked girl’s clothes. It really didn’t start to happen until the day after they had moved in and came over to meet us. At our front door were her mother Janet and her father Lance. Standing behind them was that angel again. She had on a gorgeous pink dress that came to her knees with pink and white tennis shoes on. I couldn’t help but stare at her. I was wishing I could wear what she had on. I was ignoring her parents. They were adults, so I could care less what they were talking about. I guess I was staring too long because that little angel that was standing there gave me a funny look and stuck her tongue out at me. Oh, it’s on now girly. What else could I do? You’d think I do the adult thing and turn the other cheek. Nope not even close. I did what all nine year old boys would do. I stuck my tongue out right back at her, with a little more emphasis for good measure. I then felt a sharp pain in the back of my head where my mom had just smacked me.

“Mathew Drayson. That’s not the right way to introduce yourself. You apologize right now mister, then go to your room and think about what you did.”

“I’m sorry.” I didn’t even know her name yet and she had already gotten me in trouble. My Mom smacked me on the butt as I walked up the stairs to my room.

“Ouch!” I yelled in surprise, trying to win sympathy from anyone in the room. I didn’t get it, but it really didn’t hurt either.

I sulked in my room for hours it seemed. I did what my Mom asked and thought what I had done. Yeah right. What I thought about was how I could get back at that little minx.

Mom came up to my room a little later and asked if I had thought about what I had done. “Mathew, did you think about what you did? You know it’s not nice to treat people that way. Especially the ones you just met.”

“Yes Mom. I’m sorry but that girl started it.” I said, shifting blame to her. It was her fault anyway, wasn’t it?

“Don’t put fault on that girl. Her name is Karen, by the way. You need to accept responsibility for your actions young man.” Mom said sternly as she sat on my bed next to me.

I thought about it for a second and felt sorry for making my Mom mad. “I’m sorry Mom, but she did stick her tongue out at me first.” I said again as I tried to get out of trouble.

“I don’t care what Karen did, you need to learn how to be a gentleman, and not do things like that to girls.” I thought she was mad before, but now she had turned red and was fuming. Now I’m in trouble. How do I get out of this one? I already said sorry twice, now what do I do.

“I expect you to act better Matt. No television for you tonight. Now get ready for bed.” She said finally and closed the door hard as she left me to myself. I was now feeling pretty lousy. I didn’t mean to piss her off and now I don’t get to watch TV. Oh well, I guess I’ll read a book. You guessed it. This is where I learned to love reading and my grades started to go up. I grabbed a book off of the shelf. It was called “Sphere”. Yes, I know they made a movie about it. But the book was great. My love for science fiction and fantasy books just grew from this first book. I must have read for hours because when I finally set it down it was almost midnight, and I had school in the morning.

I woke the next day tired. But I think I had a new outlook that morning. I don’t know. Maybe it was my Mom yelling at me or maybe it was the book. Who knows, I’ll blame it on Mom for now I guess. As I walked out to the corner, I met up with Josh. We hurried off to school as we were running late. We had gotten probably 15 feet from our houses when we could hear the unwelcome screech of a female voice.

“Wait up guys, let me walk with you.” My little angel with horns on her head said.

We both ignored her and walked a little faster to try and stay ahead of her. To no avail I might add. She actually skipped up to us in order to catch up. I mean such a girl thing to do, huh? Then the little thing practically sang as she looked right at me and spoke. “I’m sorry for getting you in trouble yesterday. It’s entirely my fault.”

What, an apology? This was unexpected. Who was I to argue with the angel that was looking at me with that cute smile and long luxurious hair in a pony tail? She had on another cute dress. It was purple with flowers on the bodice. She was wearing white tights and the same shoes as the day before. God, how I wish I could borrow those clothes, for just ten minutes. That’s all I would need.

She continued in her musical voice. “So we can get together at my house after school ok?”

Boy I was just head over heels for this girl already. I’m in big trouble. Oh, did I mention I missed everything else she just said? I must be under some sort of spell. Now I’ll have to ask her what she said.

“I’m sorry, what did you say before?” I asked politely.

“I said I would make it up to you with some cookies and milk at my house, as a peace offering. My Mom and I baked them last night. My Mom said something about the smell of fresh cookies making a new house smell like home.”

“Um, ok after school then.” Ending what I was hoping was the last of this conversation and I would have it quiet for the last two blocks it took to get to school. Boy was I wrong. I don’t think she even stopped talking to breathe. I thought this would end as we reached school and we would go our separate ways. I was in the 4th grade and I hoped she was still in 3rd grade. Nope, not a chance. She sat next to me on the right side while Josh took his usual seat to the left. We were the second row back in case you were wondering. I sighed at the thought of sitting next to her for the next month. School was ending soon for the summer holidays. I couldn’t wait. So much goofing off to do and little time to do it. My daydreaming of summer ended with our teacher taking roll and introducing the new girl.

“Everyone this is Karen Somers. She’s new here. I expect you all to treat her with respect and help her get around for the next few days.” Mrs. Thompson looked right at me with that statement.

Why me? I thought. I mean she’s a nice teacher and friendly. But why should I take time out of my busy day and help out that little devil? “Because she’s cute you dork.” A voice in my head told me. Now my own head was messing with me about this girl. I guess I shouldn’t argue with myself. So I swallowed my pride and agreed.

“I’ll do it Mrs. Thompson.” I answered and gave Karen an evil smile. She must have missed it because she was giggling and told me we were now friends.

“Oh goody Matt. You and I are now friends.” Karen stated as a matter of fact.

Oh goody huh? Now I have a girl telling me what to do already.

“I guess.” I answered her.

The class went on after that. I won’t bore you with what happened at school the rest of day. It was just a normal day. I did show Karen around all the hot spots and such, that’s all. Josh and I left school for home with Karen close behind. Again she skipped to catch up. I saw her come up and for some reason butterflies decided to do somersaults in my stomach as she talked to me.

“Hi Matt. We’re still on for cookies and milk, right?” She said with a tone of voice that said I would be there.

“I have to ask my Mom first.” I told her, I prayed my Mom wouldn’t let me go over. Come on I was still nine and really only wanted to play with Josh.

“Ok, I’ll have them ready for you when you come over.” Karen said. She was sure I would come over.

I tried to walk the rest of the way home in silence but as you might have guessed, Josh and I learned everything from her last school; friends, pets and, everything leading up to the move to next to me. For some reason, I was listening to every word she was saying. There was that spell she had me under again. I was daydreaming as I imagined I was the one in that purple dress skipping along the sidewalk home. We finally separated when Karen skipped up to her front door and told me she would see me in a few minutes.

“Don’t be long Matt, I’ll be waiting.” She said as her walked into the open door then closed behind her.

Josh was now laughing hard as the door closed.

“What’s so funny?” I asked my best friend.

“You and your new girlfriend, that’s what.” He said holding back his laughter.

“She is not my girlfriend Josh, that’s not funny.” I pleaded in my defense. “I never said that she was.”

“Well I think you will be very shortly. I saw how you were looking at her. You’re in love my friend.” Josh said as he punched me on my shoulder and ran off to his house with laughter.

Oh joy. Now my best friend is plotting against me with this girl. I then realized I was now skipping up the walk to my front door. What the hell was that about? I stopped myself and looked around to make sure no one saw me. As I entered my house my Mom greeted me with even more scheming against me.

“Matt, Karen’s mom called and told me that you wanted to go over and spend time with Karen. I think it’s a great idea for you to meet someone new. You go ahead and go over. Remember to behave and don’t forget to thank Mrs. Somers. ”

“Yes mom.” I put my school bag down and turned around down the walk of death to Karen’s house.

I knocked on the red front door and awaited my fate. My butterflies were doing a circus act now. I could not get the vision of that girl out of my head. And I did not want my feelings to be known about how I felt about her and her clothes. The door then flew open and my little angel was there to greet me.

“Matt! You’re here, come in.” She said with excitement and led me to the kitchen. As I walked in her mom greeted me.

“Nice to see you again, Matt. How was school?” Karen’s mom asked. And even before I could answer, once again that girl was in charge and answered for me.

“It was great mom. He showed me all around school and introduced me to his friends and everything. I like him.” She said embellishing a bit. “That’s why I invited him over for cookies; as a thank you.”

“That’s nice Karen. Thank you Matt for being nice to Karen.” Her Mom said as she placed a plate of chocolate chip cookies and two glasses of milk on the table. The cookies were fantastic. Karen and I ate the whole plate. She kept smiling at me between bites. I couldn’t help myself and I smiled back. I wasn’t forcing them. Once we had finished the cookies Karen got up grabbed my right hand and dragged me out of the kitchen.

“Let’s go. I want to show you my room.” She said dragging me down the hall to her room. I had no choice but to follow with a dumbstruck look on my face. When in Rome I guess. Her room was filled with boxes and her clothes were strewn about haphazardly. I was taking a look around to get a feeling for the room when my focus stopped and fell on what was hanging on the closet door. It’s was a gorgeous, white satin flower girl dress with lace. It looked to be about knee length, and I was stunned with its beauty and elegance. How I wanted to walk over to that dress and just touch it. I came out of my daydream by some nudging from Karen.

“Matt, are you OK? You seem to be daydreaming.” Then she looked in the direction of my gaze. “That’s a flower girl dress I wore to my aunts wedding last month. It’s beautiful, isn’t it?”

“Yes, I wish I could wear it.” Oh shit, did I just say that out loud? Now I’m in for it. The look on her face was not one of surprise or disgust as I thought it would be. It was one of understanding.

“You want to try it on?” She asked, but didn’t wait for me to answer.

She took the gorgeous dress off its wooden hanger and brought it over to me and put it up to me. My heart was beating so fast I thought it would burst from my chest. I reached out my shaking hand to touch the material of the dress. Something else unexpected started to happen. I got hard.

“What the hell?” As the satin of the dress touched the fingers of my hand, my skin tingled. “What was I doing? Was I under her spell again?”

“Here.” She said as she handed me the dress. “Take your shoes, pants and shirt off first.”

I didn’t even think. I just did as I was told and soon my clothes were on the floor. I had my arms above my head and the dress fell into place on my body as I lowered my arms.

Oh wow, I was excited now. The dress felt luxurious and I could not believe I was standing there wearing a dress for the first time. A dream of mine I had had forever and I felt as if I was going to faint with all the feelings going through my mind.

“You look pretty in that dress Matt.” She said as she stepped back to get a better look. “How does it feel?”

“Wonderful, thank you for letting me try it on.” I said.

I was now looking into her eyes and I was getting even more feelings coming to my mind. I think I fell in love with her right then and there. “You’re pretty and cute too.”

“Thank you Matt. Have you done this before?” She asked indicating the dress I was wearing.

“No, but I have been dreaming of this for a long time, thank you.” I answered then went to her and gave her a hug. Even I was surprised as I did this. She was surprised too, but receptive. Then we broke the hug. I began to worry she would tell someone my secret.

“Please don’t tell anyone.” I pleaded.

“I would never do that. Not without your permission. By the way you’re my boyfriend now.” She said sweetly.

“Um, ok. Can I do this again sometime?” I asked hesitantly.

“Of course you can, I like you dressed like this. Maybe next time I will help you dress properly.”

“Thank you, Karen.” I gave her another hug.

“You’re welcome, now get changed before my Mom catches us.”

I took the dress off and put my own clothes back on. Once I finished she again ordered me around. I must confess I was putty in her delicate hands.

“Now help me clean up and put my things away.”

“Ok.”

I won’t bore you with every experience that we had over the last five years involving my dressing. Just that we did it a lot and makeup made its début when we were twelve.

Now back to my original problem, I guess I’ll call Karen. I grabbed my cell and pressed the button to speed dial her number. It rang only once and she answered.

“Hey, Matt. What’s up my love?” She said with her usual musical voice.

“Hello my angel. Can you come over and talk?” I asked a little hesitant.

“Sure, what’s the matter honey?” She asked with concern.

“I need to talk to you about something. Can you bring something special for me? It’s been a bad day.”

“Of course baby, I’ll be right over.” She knew that when I had a bad day I would always ask for something special from her wardrobe. She knew what I liked and always brought sexy clothes and undergarments. She arrived at my house ten minutes later with her pink backpack that she always brought my special gifts in. Karen then dropped the bag and hugged me tightly.

“What’s the matter baby?” She said as she squeezed me tighter.

“God, I love you Karen.” I told her as I hesitated to tell her my feelings. “Can we go up to my room first?” She knew it meant I wanted to wear what she had brought.

“Of course, I brought you something sexy today.” Karen said with a grin. She took my hand in hers as we walked up the stairs to my room. She placed her back pack on my bed and took out what I could only describe as sexy as hell. Red satin panties, matching bra, black mini skirt and red blouse with black pantyhose and red pumps. I quickly undressed and slid the panties up my hairless legs. I’ve kept them that way since puberty started, and I pushed my hairless self between my legs and pulled the panties up tight. God I loved the feeling of satin panties. Next came the bra which I learned to fasten without problems years ago, followed by the pantyhose. I rolled them up and pulled each leg up one by one until they were situated correctly on my waist. Next was the skirt that fell to about 3 inches above my knees. And finally the red blouse and pumps were put on. The blouse was made of silk, which of course made shudder. Karen always knew how to comfort me, and this outfit did it. I looked at myself in the mirror on the back of my closet door and drooled at the teen girl staring back at me.

“Come on let’s do your make up today. It will make you feel better.”

I had never put make up on at my house because my Mom got off work around six and I liked to have it on longer. We always did at Karen’s because her Mom got home around nine, and her Dad at ten. I must have been out of my mind because I agreed.

“Ok, let’s do it. Keep an eye on the time so I can clean up before six.” She then led me into the bathroom across the hall and did her magic. She put on pink lipstick, light blue eye shadow and mascara on me. Once she was done, she announced I was beautiful. She then played with my long hair putting it in a page boy style, and I was done.

“You look beautiful Mattie. Now let’s sit and talk about what’s bothering you.”

Before I sat on the end of my bed I took another look at the cute teenage girl in the mirror then sat next to Karen. I looked at her worried face. She had the look that I felt. I mean I felt good with the clothes on and the makeup job was great, but now I had a sick feeling in the pit of my stomach. I guess those butterflies found their way home. I was lost in thought and mindlessly rubbing my stocking covered legs trying to find the words that I wanted to get out.

“Before I start, I just want you to know that I love you very much and that nothing could come between us. Ever since we met I’ve been in love with you Karen. The clothes, the support over these last five years has been unbelievable.” I paused to reflect and gather my thoughts for a moment.

“I love you more than anything, Mattie.” She said as her arm went around my shoulder and used my girl name. “I will always love you, even if you want to dress like this full time.”

She must have thought this is what I wanted to discuss. Our time together with me dressing has become almost a daily thing. I’ve even started wearing panties to school on occasion, when I didn’t have gym.

“So tell me. What are you thinking about?”

“It’s about Josh.” I stopped there not knowing how to get the rest out.

“What about him, has he done something?” Karen asked concerned.

“No, it’s me. It’s how I feel about him.” I started and then lost the words. Then Karen leaned over and planted a kiss on my lipstick covered lips. It was wonderful. Her kisses could cure any bad feelings I had.

“It’s ok Mattie, whatever it is we’ll work it out.” Karen comforted me and squeezed my shoulder. I then leaned into her shoulder and began to cry again. “It can’t be that bad. Can it?”

Somewhere I found the strength to stop crying and I wiped my tears with a tissue that Karen had grabbed from the night stand next to my bed. “Uh oh, no mascara, she had used the good stuff, oh well I deal with that later.” Now I started to laugh uncontrollably, and she did the same when she realized that I was holding a tear soaked tissue with no mascara on it. I felt better now than I had all day.

“Maybe these feelings for Josh will go away in time.” As long as I have Karen for support maybe this will pass. Not likely, I know how I feel and I want to act on them. It’s probably lust. I mean he is cute and sexy. Did I just think that? I’m in big trouble.

“Karen I’m having sexual feelings towards Josh, and I think he knows.” I finally spit it out after all of that.

“Oh is that all? I thought you were going to tell me you wanted to dress as a girl full time. Either way I would have been OK with it. In fact I think it’s OK if you have feelings for him. It’s kind of my fault anyway. I have taught you how to be more feminine over the years and you took to it very easily. I mean look at you. You’re a beautiful girl.”

“I am aren’t I? So you’re OK with me having feelings for Josh?” I asked still a little hesitant.

“Sure. And if you want to experiment with him, I’m OK with that too.”

“Really, you would be OK if I wanted to do stuff with him?” I asked excited and horny. I’m 14, so sue me.

“Absolutely, I have one condition though.” Karen stated with a smile. “I get to watch, and you have to be dressed as you are.”

“Um, OK. You’re sure?” I asked, getting more excited as I imagined the possibilities.

“Oh yes. I’ve wanted to see you do that for a long time. I just didn’t suggest it until I was sure you would go for it.”

“Ok, um… What about Josh? I don’t think he would be game.” I was now feeling those butterflies again. Would Josh want to get with me sexually? Not a chance, for sure.

“I wouldn’t be too sure about that.” She said as a matter of fact. “We’ve known you might be interested in him for a while, but wanted to wait for you to confirm our suspicions first. Now that you have, all you have to do is tell him.”

“You’re kidding right?”

“Nope. But it’s up to you to explain your clothes.”

“How am I going to explain all of this?

“Oh, we’ll think of something.” At that very moment our conversation ended with the realization that the front door to the house had just closed down stairs.

“Oh shit. It’s my Mom. Now what do I do?” I indicated how I was dressed.

“I guess now is a good a time as any to let her know about Mattie.” She said snickering.

“I guess you’re right, but I don’t want to give her a heart attack. Will you go talk to her in the hall first and ease her into it?” I said in almost a panic now as those butterflies were joined by a herd of elephants.

We then heard my Mom yell up the stairs for me.

“Matt! I’m home. Are you in your room? I need to talk to you about something.”

“Yeah, Mom. Just a minute. Karen is here.” I yelled back at my Mom, then looked at Karen now in a full panic.

“GO! Please help me through this.”

“Don’t worry sweetie. I’ll help you.” Karen assured me as she walked into the hall and closed the door until there was just a crack in it. I guess so I could hear them, which I did.

“Hello Mrs. Drayson.” I heard Karen say.

“I keep telling you, call me Linda. How are you Karen?” Mom asked my girlfriend.

“Sorry Linda, I keep forgetting. I’m doing great, thank you.”

“What’s Matt up to?”

“Well…we sort of need to tell you something?” I heard the nervousness in her voice. I was breathing hard with anticipation and mindlessly rubbing my legs again.

“Oh! My goodness. No.” I heard an audible inhale as my Mom was expecting something bad.

“You’re not pregnant are you?” She asked with fear in her voice.

“Absolutely not. It’s about Matt.” She squashed the first fear and brought a new one.

“He’s OK isn’t he? Is he hurt?” My mother asked with anguish.

“No, of course not. He’s fine. He just wants to show you a new outfit that he’s wearing.” I could hear the kindness in her voice. “But before you go in don’t freak out when you see him.” I then stood up and smoothed out the skirt and blouse and awaited my fate. The door to my room opened and my Mom walked in. She gasped as she saw me standing in the middle of my room in that black mini skirt, blouse, red pumps and makeup.

“Oh my” She paused as she looked me up and down. “Wow you are a very pretty girl. What’s your name, honey?”

“Mattie” I squeaked out. I then saw Karen just behind my mom for moral support.

“Well it’s about time I finally get to meet you.” Mom told me with a smile.

“What!” Both Karen and I said at the same time as we looked at each other in shock.

“Oh I’ve known for ages. I found some things of yours Karen. Then I saw Mattie wearing a bra a while back. I knew that you would come to me in time and I didn’t want to press the issue.”

I couldn’t help myself and gave my Mom a great big hug. Karen joined in for a group hug.

“You don’t care that I like to dress like a girl, Mom?” I asked just to be sure.

“Of course I don’t care. You are my son, and I love you no matter what. How you decide to dress is your business. You make a very pretty girl. I am happy that Karen has chosen to not abandon you and that you can share this with her.” Mom then turned to Karen. “How long have you known about this Karen?”

“Well um...” Now Karen was trying to get the words out. “For five years since we first met at my house for milk and cookies the day after we met.” She said quietly.

“That long? How did this start?” Mom asked both of us as she sat on the bed. Karen and I sat with her, me on the left and Karen on the right.

Both Karen and I related the story about how this all began. My Mom gave both of us a hug with either arm. “I am so happy you finally told me about this and the whole truth, It makes me proud and delighted you two are able to share this and still be a couple.” Mom said with a smile and patted my on my knee.

“I love her more than anything, Mom. I think Karen and I are sole mates.” I said smiling at Karen.

“I love you too, Mattie. Nothing could separate us.” Karen said with honesty.

“Well it seems you two have figured out your love for each other.” Mom then paused; probably trying to form what I knew was on her mind. “Um have you two um… you know… slept together?”

“Mom!” I shouted. “Sorry, I know you are worried about us. But no, we have not ‘Slept’ together.” I told her the half truth. I wasn’t ready to tell her about our time together with us and our oral pleasuring of each other.

“Is that true Karen?” She was giving Karen a questioning look that screamed ‘Don’t lie to me’.

“Sort of, we have done a few things together.” Karen was obviously more open to discussing our tirades than I was.

“Like what?” Mom asked.

Karen looked embarrassed but admitted to our giving each other oral pleasure. “Well Mattie and I have given each other oral pleasure. But that as far as it’s gone. I will admit I would like to do more with Mattie.” Her face became flush and red as she completed that statement.

“Oh, um... Well I guess I will have to get Mattie some condoms pretty soon then. Won’t I?” Mom asked looking right at me.

“I guess that would be a good preventative measure should Karen and I decide to go that far.” I finally found my voice and I sounded almost adult about the issue.

“That’s very adult of you Matt. As a boy, you need to know the responsibilities of preventing unwanted pregnancies with your girlfriend. Now this does not give you two kids permission to have sex and be for warned I will be calling your Mom about this Karen.”

“That’s OK, Linda. My Mom already knows about our activities. I tell her most everything. She’s still in the dark about his dressing in my clothes though.” Karen told my Mom.

“Oh I doubt that, I’ve had a few conversations with her as to where the panties I found came from and she knows of your secret as well. We both think it’s cute and don’t care either way Mattie. We love you both and accept you as you are.”

“Thanks Mom.” I said with tears in my eyes and hugged her tightly. And at that very moment we all realized we had company. I turned around to the door to my room and saw Josh standing there with his mouth open and a very confused look on his face.

“Um…Uh Hi. I rang the bell and when no one answered, I came to see if Matt was in the shower or something. But this is… well an unexpected find.” Josh said as he walked up to me and looked me over.

“Wow, Matt you make a pretty girl, I never thought you would look this good…sexy even.” He said at last as his eyes were jetting around taking all that I was in.

“Thanks Josh. Karen and I were just explaining this to my Mom when you walked in.” Josh was still looking at me. Man, those eyes of his were burning my sole. I could lose myself in them for days.

“Wait. What did you mean you never thought I would be this pretty?” I asked puzzled at what he had just said. Did everyone know about my cross dressing?

“Well I’ve sort of known for a while Matt, or is it something else?” He asked.

“It’s Mattie. Not much of a stretch, but that’s me as long as I dress as a girl and it’s kind of been going on for years Josh. It was high time I told someone other than Karen. Funny thing though, Karen and my Mom had the same suspicions as you probably did.”

“Just so you know Matt, I’ve known for about a month. I saw you at school one day and I could see that you were wearing panties. I saw the red when you bent over to tie your shoes.”

“Why were you looking at my ass Josh?” I said hopping for the best outcome. As I looked at his face turned bright red and finally smiled.

“Because I think it’s a nice ass.” Josh admitted and came to me and put his hand on my shoulder. My Mom’s expression changed to that of utter surprise.

“Am I missing something?” My Mom asked. All three of us kids kind of shrugged and I thought it was my responsibility to let that cat out of the bag.

“Well Mom…that’s another thing I wanted to tell you today. We just hadn’t gotten that far yet when Josh came in. What I am telling you is that I’m in love with Karen and I’m in love with Josh. I had already told Karen of my feelings for her and for Josh. She said she was OK with it and if I decided I wanted to act on them it was OK.” I left the part of her wanting to watch out. I didn’t want to freak out Mom too much in one day.

“Does that mean you are bisexual, Mattie?” Mom asked with an expression that was hard to read.

“Yeah, it does Mom. I hope you are not disappointed or hate me.” I was a little scared what her reaction would be to hearing her son was not only a cross dresser but also bisexual.

“I could never hate you Mattie. You are my child and I love you unconditionally. I’m just a little overwhelmed. Standing in front of me is a beautiful teen-aged girl that is my son and he has now admitted she has feelings for her girlfriend and his best friend. I refer to you as both because I’m not sure which you prefer. I will need a little time to adjust to my new daughter.” Mom had a small smile on her and then came closer to me. “Come here sweetie and give your Mother a hug.”

I did just that and held my Mom tightly and cried lightly into her shoulder, I then felt two more sets of arms wrap around me as Josh and Karen joined in the hug.

“We all love you Mattie, no matter what happens from this point forward.” Karen reassured her approval.

“Yeah, Mattie. Well, I guess you know, I love you, too.” Josh said quietly, probably not sure how to feel.

“You do?” I said as I broke free of the embrace and wiped the tears from my eyes.

“I just said that Matt. I do love you, very much. You are my best friend and maybe after today, even more.” He said hesitant to the reaction that might come.

“It’s OK if you want more from your relationship with Josh.” Mom said reassuring me. “I know this part of you is new to me but I will not stand in the way of whatever you three decide is right for you. And no matter which way you decide to go Matt I will support you.”

“Thanks Mom. You’re the greatest. Karen, Josh and I will talk about it more. I think a nice walk to the park would be nice and help to clear our heads.” I recommended.

“That’s a great idea Matt. I guess Josh and I will wait downstairs for you to change.” Karen said as she stood up.

I thought about that for a minute and thought, screw it. “That’s not necessary. I would like to go as I am. Now is the best time to take another big step and let Mattie out for a walk.”

“Are you sure about that Mattie? I mean you look nice and I’m sure no one would recognize you. I just want to make sure you are ready for such a big step?” Mom asked with a concerned look.

“Yeah I’m sure. I have always wanted to do that and its high time Mattie left the confines of Karen’s or my room.” I said with assurance. I really was excited to step out into the real world for the first time.”

“Ok Mattie it’s your choice. Watch out for my new daughter, you two.” Mom instructed Karen and Josh.

Karen and Josh followed me out the front door of my house and, no sooner had I stepped out into the open, those damn butterflies showed up. I froze in fear, but Karen nudged me out farther.

“You look beautiful Mattie, go ahead.”

I swallowed hard and took a few more steps. As Karen, Josh and I reached the sidewalk, we headed towards the park. This took us right in front of Josh’s house. His Mother was outside getting ready to leave. She waved at all of us and smiled at us as we walked past.

“Josh, please come over here for a second.” Josh’s Mom called to him.

“Uh oh. Now what? I guess we’ll have to explain all of this once again.”

“Sure Mom, what’s up?” Josh greeted his mother.

“Hi Mrs. Benson. How are you?” Karen said sweetly as we approached Josh’s Mom.

“Fine. Thanks Karen. Josh, who is this young lady?” Mrs. Benson asked while smiling at me.

“Hi Mrs. Benson. It’s me, Matt. But you can call me Mattie.” I thought I might as well get that out of the way. Mrs. Benson smiled even more brightly than before and I got another big surprise.

“You look nice Mattie, your Mom and I have talked about this a few times and we were wondering when Josh would introduce us to the girl next door.”

“You knew too?” I asked puzzled.

“Yes, it was the little things. I know that Josh had feelings for you for a long time. And when I found out you were into girls clothes, I had hoped you two could have a relationship.” Turning to Karen she said. “Karen I know you and Matt are boyfriend girlfriend, but I hope you understand that all I am hoping for is my son to find his true love.”

“I never told you anything Mom. How did you know? Josh asked surprised as I was.

“A Mom knows her children honey. And the way you two looked at each other over the last few years gave me clues. How do you feel about this Karen?”

“To be honest Mrs. Benson, it kind of turns me on, and I told them that I will be involved one way or another if they decide to act on their feelings.” Karen told her of our deal.

“Wow, I’m impressed with your attitude Karen. I will tell you all now, that if you act on your feelings, that all of you need to act responsibly.” Mrs. Benson commanded.

“Oh we will Mom. In fact, Mrs. Drayson insisted on the same earlier.” Josh assured her.

“So what are you three up to now anyway?” Mrs. Benson asked.

“We were just headed to the park to clear our heads and have a talk.” Karen told her.

“Ok you three, be safe.”

“We will Mrs. Benson. Today is a first for a lot of things. Like today is my first time out fully dressed as Mattie. I kind of like it. I might do this more often. Well, except for at school.” I was truly enjoying being outside, the way the skirt and pantyhose felt was fantastic. “We’ll be back in a little while.”

Karen, Josh and I continued our walk to the park. Once we arrived, we picked a table to sit at. Karen and Josh both sat on either side of me as I sat in the middle of the table’s bench. Josh put his arm around my shoulder and Karen put hers around my waist. I could get used to the attention I was getting. The only problem was that I was getting hard. I was straining against those pretty pink panties I was wearing. With all the attention along with being in the park dress, I was I was in sensory overload and needed relief soon. Karen started rubbing my tummy. This did not help my current situation, and Josh started south and put his hand on my left breast.

“I love you both, but if you don’t stop what you’re doing, I’m going to make a mess in my panties.”

“I don’t care Mattie. I’m so hot for you right now, we need to find a place to go.” Karen said putting her and up my skirt and found Mattie junior. I audibly moaned my approval.

“I can’t agree more, but where can we go?” Josh interjected.

Karen was now sliding her hand inside my panties and stroking my hardness. I turned towards Josh and smiled at him. He then leaned in and our lips met for the first time. I melted into those pert lips of his and felt his tongue slip between my lips. My senses surpassed overload into imminent danger of explosion now. I broke Josh’s incredible kiss and pulled Karen’s hand from my panties.

“Stop please you’re going to push me over the edge.” I pleaded with them both.

“You’re just so hard to resist Mattie, I love you.” Karen said and kissed me next. Oh I could definitely get used to this for sure.

“Hey, I love you to Mattie. I need to have you soon or I’m going to blow. That kiss was fantastic.” Josh said with a huge smile.

“I know I almost blew when you did that. Let’s go somewhere quick.”

“I get to watch remember.” Karen instructed. “We can go to my house; Mom and Dad won’t be home for hours.”

“Ok, let’s hurry.” I said leading the way to Karen’s. We couldn’t get there fast enough. As we entered her room, she took me into an embrace that would melt a witch’s heart. I even lifted my leg. It was so intense. Then Josh butted in.

“Hey I want some too.” He whined.

“Oh alright, I get to watch.”

“I want to watch you two also. I’ve always wondered what it would be like to see two girls make love.” Josh said with a smile of anticipation.

I could see the lust in his eyes and I am sure he could see in mine. I took him in my arms and we kissed for the second time. I was in love with the second person of my life, it was fantastic. I wanted more. I broke our kiss and slowly went to my knees. I know what I wanted now. I pulled down his pants and underwear and slid his hardening cock into my mouth. I was soon sucking him for the first time and loved it. The feeling of the hardness and the soft skin on my tongue was amazing. I pulled him out temporarily to get his hairless balls into my mouth and rolled them around with my tongue. They felt wonderful in my mouth but I missed the main prize and slipped his shaft back into my salivating mouth. It was not long when Josh let out a loud moan and I felt jets of his sperm flow into my mouth and down my throat as I swallowed all he had to offer. When he was done, his legs buckled and he sat on the floor with me never letting his cock fall from my mouth. I finished cleaning him up and let his flaccid cock fall onto his flat stomach. At the same time I heard a squeal from Karen and saw her playing with herself feverously as she came with a shudder.

“Oh my god. That was too hot to watch Mattie, I must see the encore now.” Karen said almost out of breath.

“Oh yeah Matt, that was amazing. You were great and now it’s my turn. I called you Matt because I am going to suck a boy’s dick and not a girl’s clit right now.”

“I don’t care what you call me Josh. I’m too hot to care right now, so go for it.”

Josh complied. He raised my skirt and lowered my pre-cum covered panties. He did not hesitate to put me in his mouth. He was sucking me like a pro. I was surprised that he was able to deep throat me in one shot. His mouth felt amazing and I knew I would not last long. I had Josh pumping my cock in and out of his mouth and Karen fingering herself next to me. I then shot my load down Josh’s waiting mouth without warning. I was surprised again when he willingly swallowed my gift to him. He quickly cleaned me up and did not miss a drop.

“That was so good Josh, thank you.” I said breathlessly.

“I know I loved every second of it and well definitely do that again. I love your cock Mattie.”

“I love yours too Josh, I guess it’s my turn to help out Karen?”

“You got it. Now get those pretty lips and tongue over here and finish me off.”

I immediately did what I was told and started to lick up and down her pussy. I found her clit and she then started to buck wildly. She had an orgasm in short time. I guess watching Josh and me made her hot. We all lay on her floor together as our teen bodies recovered quickly.

“That was the most incredible thing I have ever experienced. It was so hot watching you two.” Karen explained still coming down from the intensity of our play.

“It was wonderful wasn’t it?” I added. “I love both of you so much. We should get cleaned up and get home.”

“You girls need to fix your makeup before we go, unless you want to look like a couple of tarts.” Josh said laughing.

Karen and I looked at each other in the mirror. Both of our faces looked disheveled and needed fixing. Karen and I redid our makeup after washing our faces and cleaned up our hair. After we finished, we walked out to get Josh’s assurances that we looked presentable.

“Josh, how do we look?”

“Beautiful. Good enough to kiss.” Josh said with a grin.

The three of us walked out of Karen’s house and went over to mine. Mom was watching television when we all walked in.

“How was your walk to the park?” Mom asked as the three of us sat down on the couch.

We all gave each other a knowing look and I answered her. “It was good Mom. We discussed our options and came to an agreement that the three of us are now together. I now have a girlfriend AND a boyfriend.”

“I see. And did you have fun over at Karen’s?” Mom asked with a smirk. She obviously knew more than she was letting on.

“What do you mean Mom?” I asked nervously.

“I saw the three of you go into Karen’s house over an hour ago.”

“To be honest mom I had sex with Karen and Josh. It was wonderful Mom.”

“I knew something like this would happen. I am just glad it was with people you love. I expect you to be careful and use protection from now on.”

Mom talked to us about lots of things for the next half hour. Then when she finished, Josh and Karen left to go home. Mom and I were still sitting together on the couch.

“So Mattie, now that you have been out dressed like that in public, what’s next?”

“What do you mean Mom?” I asked puzzled.

“Well, are you planning on being dressed as a girl more often?”

“I guess I will. I have wanted to go out in public as Mattie, and the urge is stronger now that you and Josh both know.”

“Well it’s OK with me if you want to. However, if you decide to do it again, I would like to help you.”

“You do? That would be great Mom.” That being said, I went to my room, took a shower and changed for bed. I went to sleep knowing I had a great Mom, a beautiful girlfriend and a sexy boyfriend. I then dreamt of being at school as Mattie and being accepted.

TO BE CONTINUED