NEW! What Goes Around Comes Around *Illustrated

Karen Jensen 

The local high school is now closed, Mark Taylor's mother enrolls her son after learning about a prestige all girls private school that recently allowed boys as part of a coed pilot program. He meets lovely Serena Brogdon, who is partnered with him after a unique school fundraiser event, a  beauty pageant...one without girls!  

“Mom, please don’t make me go to this school. It’s for girls!”

“It was for girls only dear, but they are admitting boys for the first time and it is an excellent school. With Adams HS closing the only other option would be to bus you to Centerville and that is an hour each way."

 

“But the uniform makes me look like a sissy. It is the same as the girls’ uniform except they exchanged the skirt for shorts. No boy wears them this short.”

The shorts were made of a thin fabric that were comfortable, but looked snug against my pelvis. They also slightly rode up between my butt.

“I think you look adorable.  I don’t want to hear any more. This is where you will be going to HS. Now give me a kiss and go before you are late on your first day.”

I leaned over, kissed her cheek and got out of the car.  I adjusted my tie and straighten out my blazer that came with my red uniform. I saw a few other boys I knew heading towards the school and ran over to join them so I wouldn’t have to enter the school alone. Some looked like familiar faces from my old school and was thankful I was not alone. I was sure the girls would tease us about attending a girls’ school and my instinct proved to be correct.

Adams HS was the school I was slated to attend before the county closed it just a month ago. Attendance was dropping and it made no financial sense to the governing school district to keep the school open. The only school close by was Jane Powers Finishing School for Young Ladies. It had been founded back in the 19th century to teach girls feminine grace, child care, and how to take care of their future husbands. However it changed with the times and at some point it transitioned into a college prep school for girls but the name remained the same. The school maintained an older turn of the 20th century exterior, but also had more modern buildings for their tech and science classrooms. Over 99% of their graduates attended college and the large majority of those women were very successful in their chosen field. They also had a scholarship program that was envied by most schools in the state. That was one reason why my mom was so anxious for me to attend. When the announcement was made that Adams HS would close, the Jane Powers School agreed to admit 20 boys as a pilot program to see how that would work. If the program was successful they would admit more boys the next academic year. They would then transition to a full coed school. So, in other words, I was a guinea pig.

That first day was orientation for the new students, both girls and boys. We met in a large auditorium and were introduced to all the teachers. While there were only 20 boys in the incoming class, there were about 40 girls, so we were a small minority. It was no surprise but a bit shocking seeing the numbers. The boys all gravitated together and we were all quite nervous as one can imagine we felt unwilling invaders.

The principal, Ms. Schultz, the principal, was a well dressed woman in her late 40s who walked with grace and confidence to the center of the stage. The spot light illuminated her tight white pencil skirt and sleek blazer along with her immaculate updo hair style.

"Welcome new students to the Jane Powers School," she said. "This institute is rooted with a tradition of academic excellence combining our rich historical traditions with the latest in state of the art facilities," she said.

After a brief history of the school and its various programs she explained the various rules we had to follow and told us about the school in general. They were all in the student handbook we had received. The last thing she mentioned was the annual fundraiser the school held in the spring. It was up to the students to come up with ideas for the fundraiser. The staff would pick out what they thought were the best ideas and the student body would vote for the one they wanted to do. With the students involved in the selection process the staff felt they would be more apt to participate. She told us that the previous year had been a fashion show and had been very successful.

The next day was the first day of classes. We had been given a tour of the school as part of orientation so we knew where our classes were located. I was relieved to find that our classes were all single sex. The only opportunities for mixing with girls were at lunch and daily assembly which was held first thing in the morning. I was too shy to do that. Instead I found a few other boys who also preferred to ignore the girls.

I managed to settle down after the first week and actually enjoyed my classes. There were only 10 students to each teacher so we got a lot of individual instruction. The professors kept us engaged and were demanding, but were reasonable with the number of assignments. With their encouragement and attention, I saw my grades rise significantly. It still felt strange to see so many more girls than boys in the hallways when changing classes.

We were teased a lot by the girls during the first couple of weeks but that gradually died down.  I think part of it was due to us boys invading their school. They had to give up some of the restrooms as well as give up one of the newer locker rooms to us. Either way I still I blushed when a girl asked me if I had an extra tampon, or was I wearing panties under my shorts. Being extremely shy I rarely interacted with any of them.

When we returned from winter break we were asked to suggest possible fund raiser events by Ms. Chen the Director of Activities and Events.

"Young ladies and gentlemen, as you all know we are holding our annual fundraiser, and last year was a smashing success. We hope this year will be even better."

The staff would pare them down and present what they considered to be the best to be voted on by the students. The final candidates were another fashion show, a womanless beauty pageant, and a carnival.

On April we had an assembly where Ms. Chen announced the results of the vote. Overwhelmingly a boys’ beauty pageant was chosen. I was certain that few, if any of the boys voted for that. I certainly did not.

"After the votes and our meeting with students and staff, we believe this event will be a success in terms of raising funds and will serve as a unique gender learning experience," she said.

 I had never heard of anything like that but knew that I was not going to like it. Each boy would dress as a girl and strut across the stage like a model on a runway. We would have to wear two different outfits. The first would be casual dress that a girl might wear to a movie or to hang out with friends. The second would be a more formal outfit to be worn to a dance or perhaps dinner at a fancy restaurant. Each boy would be assigned a girl to tutor and advise him. The girl would be in charge. Any boy who refused to participate would see his grade point average negatively affected. Since all of us were here to prepare for college it was a sufficient incentive to participate.

At that point the principal called each boy up by name and the girl who was to be his tutor. We were told to come up to the stage with each boy and his girl tutor standing together. The girl who walked up on stage with me was what I would call a knockout. She was about an inch or so taller than me, modest breasts, piercing green eyes and long auburn hair that she wore in a high pony tail. She had the most beautiful smile and as I was to find out a real bubbly personality. I think I was in love before she even said a word.

“Hi Mark, I’m Serena Brogdon” she said as she held out her hand. Then she giggled and said “but I guess you already knew that”.

I smiled back at her as I took her hand. The first thing I noticed was how soft it was. I could feel myself getting hard and hoped no one would notice as I stood on the stage facing the rest of the student body. The thin fabric of the uniformed shorts wouldn't help me conceal how I felt about being partnered with Serena. After everyone was introduced and paired with their ‘girl handler’, the assembly ended. The school day was over and I went to my locker to retrieve my stuff. When I left the building Serena was waiting for me with that same beautiful smile.

“Do you have a few minutes?” she asked me.

“Yeah, my mom works so I don’t have to be home at any specific time.”

“Cool, let’s grab a soda so we can talk.”

I was surprised when she boldly grabbed my hand and led me to a diner a few blocks away. It was fairly empty and we grabbed a booth. We each ordered a chocolate ice cream soda.

When the waitress left she got a serious look on her face 

“I have to be honest with you, I really want us to win this contest! I think we have a really good shot, with my knowledge and skills and with your cute features we could win this and make this fundraiser a success”

I wasn’t all that anxious to win but I would be kidding myself if I even thought that I didn't enjoy being around Serena. I wanted to get to know her better so I agreed that it was what I wanted also.

“Great! I have a plan to give us the best chance but you are going to have to do everything I say. It may be a bit uncomfortable for you since I am going to teach you not just how to wear the clothes but also how to act like a girl. By the time of the pageant I want there to be a question in the judges’ mind about your true gender. Do you think you can do that Mark?”

I swallowed hard and thought for a few moments. I knew I would have to wear girls clothing for the pageant but it sounded like she wanted much more from me. I looked into her beautiful green eyes and at her gorgeous smile and nodded.

“Yes. I think I can” I responded.

Her smile grew even bigger and she reached across the table and caressed my hand.

“Thank you for putting your trust in me, I will not make you look like a fool, I promise. It will be hard work, but it will be so much fun as well!”

I gave her a weak smile and nodded my head, wondering what I had just agreed to.

The waitress bought our sodas and we attacked them, eating them without talking. When we left the diner we discovered that we lived two blocks from each other and began to walk in the same direction. She put her hand in mine and I felt my erection growing again. I tried to wish it away, but feeling her hand in mine made it get even harder. I vowed to myself to do whatever she asked no matter how embarrassed it made me feel. I wanted to win the contest for her.

We reached her house first and before she turned to go in she stopped. I thought I saw her glance down and was sure she noticed my obvious hard on but she did not mention it. Instead she gave me a knowing smile.

“I like you Mark”

“Aahh….I like you too Serena,” I stammered. 

I blushed a bit knowing how 'excited' I was.

“You will need to have a girl’s name”.

“Why?”

 “Each boy who participates will have one. Do you have a favorite name you want to use? If not, I will give you one. I will call you that name when we are together. I want you to get used to thinking of yourself as a girl. When you walk across that stage you will be a girl in mind, if not in body. I will only use the girls name in private. No one else needs to know about it.”

“Ok” I replied but it made me very uncomfortable.”

“Let’s exchange phone numbers” she suggested.

She handed me her phone so I could enter my number and I gave her my phone. After returning our phones, to my surprise she gave me a quick kiss on the cheek which caused me to blush and waved as she walked to her house.

As I walked home I realized that I had no idea what I agreed to with Serena. It sounded to me like it would be really intense and I began to question whether I could do what she wanted. I knew I had to compete but did I really have to be girly enough to convince the judges? I resolved to talk to mom about it that night.

“Well Mark, it does sound like she has an intensive training program for you, but shouldn’t you at least give it a try? Who knows, you might even enjoy pretending to be a member of the opposite sex.”

 “No way! I don’t want to be a girl. I don’t even want to try to be a girl.” 

“Okay, what do you think Serena will do if you don’t follow her plan?” 

I shrugged my shoulders indicating I didn’t know.

“You said you really like this girl and she seems to like you. What do you expect will happen if you quit on her?”

“She would probably  not want to be my friend”

“How would that make you feel?

 “Awful!.”

“So, do you have your answer?” “Yeah.”

Mom hugged me and told me she was proud of me and that I made a very mature decision.”

Serena and I met again after school the next day.

“Can you come to my house on Saturday? I want to try a few outfits on you to see what will be most flattering.”

“Why so soon,” I asked nervously. 

In my mind it was all happening way too fast.

 “Because it will take some time to teach you to be a girl.”

I sighed and responded “I have nothing planned. I will come to your house on Saturday”

“Great. You will have to bring underwear. My clothes will fit you but I’m not sharing my panties and bras with you.”

“Wait! Hold on! Why do I have to wear panties and bras? We are not doing some lingerie runway show!”

“Relax Mark, The bras, because we need to make it look like you have breasts. As for the panties, your dress won’t hang right with boxers and if the skirt is short enough your boxers might show.”

“Wait! How do you know I wear boxers?”

“I can see the outline through your shorts. The material is too thin. Haven’t you notice it on other boys?”

“No. I don’t usually stare at boys.”

“I’m sorry. I wasn’t implying anything.”

“It’s ok. I’m not comfortable with the whole idea of dressing like a girl.” 

“I understand. Try to look at it as a challenge. Girl’s clothing s so much more interesting and comfortable. It’s possible you might enjoy it.”

“I doubt I will, but it is possible I suppose.”

She gave me a big smile and any doubts I had about working with hee were gone.

“Where will I get panties and bras?”

“Well….you could ask your mom to get you some. I think you will need at least 4 or 5 pairs of panties and maybe 2 bras to match your panties.”

She took my hand and said “Mark, I know this is not easy for you but remember you are not the only boy who will be wearing a dress.”

I nodded. I was afraid I was going to cry. The idea of wearing all that girly stuff was messing up my mind.

Then she kissed my cheek again and waved as she walked off to join her friends.

That night while mom looked over the bills at her desk, I asked for her help concerning the project with Serena.

"Mom…"

"Yes, honey?" She said sorting her mail.

"Do you think….you could help with..umm…getting me some panties and bras?"

Mom paused for a moment and giggled a bit before saying, "I certainly can."

When I came home the next day, she left me a bag reading, "Stacy's" on it on top of my bed. 

The note on the bed read,

"Mark, hopefully these fit you."

-Love, Mom. 

She bought me a package of panties and two bras. I never looked at them because I was afraid I would get sick to my stomach just thinking about wearing them. As I walked to Serena’s house on Saturday morning I really considered telling her I wouldn’t go through with it. I had just about made up my mind to tell her that when she opened the door. She was wearing a tiny jean skirt and tank top and before I could even say hello I had an erection. All thoughts of quitting left my mind. I just stood there staring at her with my mouth open.

“Do you like what you see?” she asked with a big grin on her face.

 “You’re beautiful!” I managed to say.

“You will be also when I finish dressing you.” She said with a big smile on her face.

 Well don’t stand there! Come in! We have a lot to do today.”

She closed the door and shocked me when she put her arms around my neck and kissed me briefly on the lips.

“We are going to have so much fun!” she said.

She took my hand and led me to her room. Serena's room was a typical teenage girl’s room with pinks and boy group posters adorning the wall. Noticing the package in my hands she asked if it contained my bra and panties. I blushed as I nodded.

“Great! Now go into the bathroom, strip, and put on a bra and a pair of panties so I can see what we have to work with.”

When I hesitated she smiled at me.

“I would see less if you were wearing bathing trunks. Don’t worry, I will not laugh at you.”

I went into the bathroom across the hall from her room and stripped to my boxers. Again I asked myself if I really wanted to do this. Then I thought of how she looked and knew I couldn’t walk away. I dropped my blue boxers and trembled as I opened the package of panties mom had bought me. They were all silky with lace. I realized I should have gone with her and picked out my own as she had suggested but the idea of doing that was too embarrassing. There were seven pairs each in a different color. I chose the white pair thinking they were the least feminine. My erection which had started to go flaccid enlarged to its full size when I slipped my panties over it. I couldn’t believe that wearing panties was turning me on.

I tried to will my erection away but it had a mind of its own. I finally decided to forget about it and hoped it would subside. Mom had gotten me 2 bras, one white and one pink. I selected the white bra and tried to put it on. I could not hook it in the back. I heard Serena calling out to me.

“Are you alright in there? Do you need help?”

“I can’t hook the bra” I responded forgetting for the moment my erection.

 “I’ll help you with that.”

Before I could stop her she was in the bathroom. She clearly saw my erection through the panties and giggled a bit looking away from my bulge. Then seeing my reaction she apologized.

“I’m sorry Mark. It was a shock to me. Do you like wearing panties? I promise to not tell anyone”

 “I..I don’t know” I said feeling like I was about to cry of embarrassment.

She sensed my distress and hugged me.

“It’s ok if you do. There is nothing wrong with it. Boys underwear is so plain and boring. If you like the panties I won’t say anything to anyone. You can enjoy wearing them with me. It will be our little secret” she said with a wink.

She was so kind that I felt a bit better after she said that. I vowed to get to know her better. I hoped we could even be boyfriend and girlfriend. Then she had me turn around and hooked the bra and adjusted the straps.

She took my hand and led me back to her bedroom. She took what she called breast enhancers and slipped them into the bra cups giving the impression that I had small breasts.

“If you tell anyone about these I will so kill you!” she said with a smile. 

“I was a late bloomer and very self-conscious watching my friends develop while I was completely flat.”

“It will be our secret” I replied feeling a bit better knowing I had a secret of hers. 

“You’re an angel Emma” she said and gave me another hug.

“Emma?”

“Unless you have a better suggestion, that will be your name while you are wearing girls clothing.”

I shrugged my shoulders. It didn’t matter to me what girl’s name she wanted.

“I want you to try on a few outfits and then I’m going to put makeup on you.”

The first outfit was a short black pleated skirt and a white peasant blouse. She had me put on black pantyhose.

“I forgot about shoes. What size are you?”

 “7 – 7 ½”.

“My shoes won’t fit but I think my mom’s might. Wait here!”

She came back with several pairs of shoes and had me put on black sandals with a small heel. They fit perfectly. She closed the door to her bedroom and had me stand in front of the full length mirror on the door. From the neck down I definitely looked like a girl. What was distressing me though was even above the neck I looked somewhat androgynous and thought I might be mistaken for a girl.

“I don’t think we will use this outfit. Take it off and we will try something else.”

I stripped down to my bra and panties and she handed me a black a-line leather miniskirt and pink sweater which left my navel exposed. She had me put on nude pantyhose and gave me black wedge sandals with 4 inch heels. I was sure I couldn’t stand, much less walk in them but I gamely gave it a try. With Serena’s help I was able to stand and take a few steps to the mirror. Again the feminine image in the mirror shocked me.

“Sit down here. I think it’s time to try some makeup.”

I sat still as she applied foundation, powder, blush, eye shadow to make my eyes pop, liner, mascara and bright pink lipstick. She took a comb and restyled my collar length hair. When I looked in the mirror again I saw a pretty girl staring back at me. It was exciting and also disturbing that she could feminize me so easily.

“Ok, there are a couple of out fits I still want you try on. Strip but leave on your pantyhose.”

Once down to my bra and panties she handed me a blue sundress with spaghetti straps and white flowers on it. It had a white lace trim on the bottom of a flared skirt making it appear as if I wore a petticoat underneath.

I didn’t have much hair under my arms but Serena told me I would have to shave them. I should point out that puberty was late and I had little body hair other than my underarms and some light hair in my groin. My legs were still pretty much hair free.

We both agreed that this dress wasn’t for me. Once again she told me to keep my pantyhose on and handed me a dress. It was pink, had long lantern sleeves and a floral print, and was smocked with an elastic high waist, a square neckline, and ruffles. It barely came to mid thigh.

Serena handed me black pumps with a 3 inch heel and helped me to stand. They were much harder to walk in than the wedge sandals.

“It’s perfect. It could be for the casual or the dressy competition. I think I like it for the latter. Take a look and see what you think Emma.”

I went to stand in front of the mirror. I was so confused looking at my image. The dress looked great on me. I liked what I saw and at the same time was distressed by the vision. I had been made into a pretty teenage girl. Serena stood behind me with a big smile on her face.

“You will overwhelm not just the judges in this dress, but everyone at the pageant. What do you think Emma?”

I just kept staring at myself in the mirror. I would have loved to have been with the girl in the mirror and was having trouble accepting that the girl was me. I turned to look at Serena.

“I can’t believe it!” I said.

“Believe it! I told you I could make you look like a pretty girl. But we will have to solve that problem” she said pointing towards my groin.

I looked down and realized that while staring at myself I had developed an erection.

Serena saw how embarrassed I was and said “Hey don’t worry. It’s ok. It's natural, nothing wrong with that. I have a solution. She reached into one of her drawers and handed me a panty girdle. 

“You will wear this under the pantyhose but for now just slip it on under the dress.”

I did as she told me and my erection was hidden, though it was still rampant under the girdle.

 “Let’s have lunch” she said. "That should take your mind off certain things."

”Great! Can I change back now and remove the makeup?”

“No, we still have a lot of work to do.”

 She reached into her closet and handed me a white shift dress that was very, very, short. 

“Change dresses so you don’t get the pageant dress dirty. You can wear this for the rest of the day.”

She had me keep on the pumps so I could become accustomed to walking in heels which I would have to wear for the pageant. She made us a couple of sandwiches and put out some chips and sodas. We were having a nice lunch when we heard the front door open. I panicked and looked around for a place to hide but there was no place to go. We heard footsteps coming towards the kitchen and I thought my life was over for sure.

“Hi mom!”

“Hi sweetheart! Who is this?”

“My friend Emma. She came over to borrow this dress. She is meeting her boyfriend later and thinks he will like it.”

“Hello Emma. It’s nice to finally meet you. Serena has been talking about you.” “H..h..hello Mrs. Brogdon. It’s nice to meet you too.” I said softly.

Of course the first thing going through my mind was she knew I was a boy. She didn’t react other than to give me a big smile.

“I left some papers home this morning that I need for my presentation this afternoon. I’ll grab them and be out of your hair. Nice meeting you Emma. Bye Serena!”

I breathed easier when she left. I looked up at Serena and she was starting to laugh. 

“It’s not funny! I was petrified she would know I am a boy”

 “I told you that no one who sees you like this would think you are a boy unless you told them. I bet even then they wouldn’t believe you.”

“Still I was scared” I said though my anxiety level had dropped. The other thing that happened was that I was trying to get hard inside the panty girdle which was very uncomfortable.

Serena cleared away our lunch dishes and announced that I was going to learn to walk in heels wearing a dress. We spent a couple of hours with my learning to walk in heels and shaking my booty. Actually shaking it seemed to be natural in heels.

She finally said we had enough practice for the day and suggested we listen to some music. 

"That should take your mind off certain things."

She insisted that I stay dressed as I was. We sat on the sofa with our legs and hips in contact. We both wanted to be together. I put my arm around her. She leaned into me, smiled and we smooched. I wanted so much to touch her breasts but I was too afraid of scaring her off. So we sat listening to music, neither of us initiating the next step.

When I realized that I had to get home she told me to change in her bedroom. I was embarrassed to call her to remove my bra but I couldn’t undo the hooks myself.

When I got home I told mom about the day including meeting Serena’s mom. My mom said she wanted to meet Serena and for me to ask her and her parents to come for dinner. We arranged it for the following week. 

That night, as I was about to go to bed I remembered I had the package of panties still in my backpack. I said to myself 'what the hell, no will know' and went over and took out the pink. I slid off my boxers and pulled up the lacy fabric underwear on and quickly got into bed. It felt so soft and wonderful against my intimate parts. Aroused I reached for one of my softer pillows and humped it under the covers until I let out a groan and spilled my seed inside my lacy underwear. I slept well that night. 

The next morning I woke up groggy as hell, I got out of bed, adjusted my T shirt. I usually use one as a PJ and adjusted my underwear that had slightly riden up my butt. I walked over to the bathroom across the hallway from my mom's room. She was already dressed.

"Morning mom."

"Good morning dear-" she paused and stood there in silence looking at me before trying to contain a giggle.

"Well, I'm glad that you are certainly taking this project seriously," she said.

"Oh shit!" I realized I was still wearing the pink panties. I quickly got into the bathroom and shut the door.

When I finally came down for breakfast, I tried to explain that I got my boxers mixed because it was dark in the room and I was too lazy to turn on the light. Mom just said it was ok, she didn't see anything and nothing happened.

When the dinner date came with the Brogdons, mom cooked one of her delicious Italian meals. She had worked briefly inside the kitchen for a well known Mediterranean restaurant while still in college, where she learned a lot of their cooking secrets.

When Serena and her parents showed up at the door, my mom greeted them with a hug and complimented how pretty Serena was dressed. Serena wore a one piece long sleeve dress that was conservative, but showed off her form and highlighted her perfect light skin. While we had dinner mom chatted with Serena's parents about how much the town had changed.  Mean while I felt Serena caressing my knee stroking it back and forth while our parents conversed. Our parents got along famously since they were the same generation. Mom whole heartedly supported the fundraiser event's idea of making over the boys as a somewhat gender experience assignment. 

"This whole thing sounded weird at first, but now I think it's a marvelous idea for the boys to learn how it feels to be the opposite gender. Almost like a cultural gender exchange program," she said. 

Serena’s parents both agreed with mom’s assessment. I was a bit shocked that her father was in agreement. I didn’t think that most men would support such a program, but then again Mr. Brogdon didn’t have a son.

"Serena honey, you have done an amazing job with Mark."

"Thank you Mrs. Taylor, it’s been my pleasure."

"No, thank you. He has become more helpful around the house and thoughtful instead of staying up all night playing his video games."

"Mom, stop it you are embarrassing me."

My mom made it no secret that she supported Serena’s plan for making me over. 

"I think enrolling my Mark in the school was the best decision I made for his education. His grades are the best they have ever been."

Both Serena and her mom nodded in approval.

After Serena and her parents left, I cleaned up the table and loaded the dishwasher while my mom finished up the laundry. 

I could not get the touch of Serena's hand out of my head. Remembering made me hard. I went up to my room, laid down on my bed, pulled down my shorts and boxers slightly out of the way and started to stroke myself. I thought about how pretty Serena looked in her tight black dress and imagined that instead of stroking my thigh she was stroking my penis under the dinner table. 

I was rock hard. I could feel my heart racing as I pumped my tool. I gripped the bed sheets with my free hand as my orgasm felt near, suddenly I heard my door open!

"Mark, I brought your laundry- ahhhh........I'm so…so sorry," mom said looking away going back out and closing the door shut.  

I quickly pulled my pillow over my waist, but knew she must have seen enough to get the idea. That night I stayed in my room. I really need a lock on the door I told myself.   

The next morning, mom apologized about not knocking and carried on like nothing happened. It was kind of awkward on the drive to school. 

All day in class all I could think of was Serena, I even started doodling her face with mine in class. I couldn't get her out of my head.

Serena taught me how to walk, how to hold my hands when I walked on the runway, how to sit and other things I thought I would have no use for, but I went along just to spend more time with her. I realized I was in love. She taught me not to stand with my legs apart, but to put them together and turn one foot 45 degrees out.

“That is the way a trained model stands and it looks much more feminine.” She stated.

Finally the day of the pageant arrived. The pageant was held in the High School gym and there would be a DJ to play dance music after the pageant was over.

We learned that day from Ms. Chen that the Smith & Wellington Law Firm who finances our scholarship programs loved the idea of the Beauty Pageant, so much that they would be offering cash prizes to the winners of the pageant and runners up.

 Serena brought the clothes I was to wear to our house where I would dress in the leather skirt and blouse for the casual dress competition. Mom wanted to take pictures before we left the house. We took several mother daughter selfies and some silly ones with Serena. I think this experience finally gave my mom a chance to experience in some small way what it would have been like if she had a daughter. 

Serena styled her hair up in a bunched up ponytail. She wore pants, a white man-tailored blouse and a blazer. She said that she wanted to be sure that the judges’ focus was on me when she escorted me down the runway.

The pageant was supposed to start at 8:00PM but Serena started preparing me at 4:00. She washed, set, and dried my hair.. She put a wave in my hair that wasn’t there before and then put it in a high pony tail with a scrunchie to hold it. While my hair was drying she filed and painted both finger and toe nails. When that was finished she worked on my face. She spent far more time on it then she ever had including trimming my eyebrows. I thought she took off too much and when she was done there was not the slightest indication I was a boy. It didn’t take me very long to dress and by then 3 hours had passed.

Serena had me practice walking in the heels, turning gracefully, standing, and sitting. All the hours of practice had paid off and she pronounced me ready. Mom drove us to the school and dropped us at the gym entrance where we would have access to the locker rooms where we were supposed to meet. We would draw numbers there to determine what order we would parade down the runway. With 20 contestants Serena hoped I would be towards the end of the line thinking that the judges would more likely remember the later contestants, but I drew number 3.

Shortly before 8:00 we were told to lineup in the order we would be walking. We would be walking the length of the basket ball court, stopping n the middle and turning to face the judges. Our escorts would leave us at that time. We would introduce ourselves (as girls) to the judges and tell them what our career plans were, as if we were really girls. Then we would continue walking to the end of the basketball court, walk around to the opposite side of the court from the judges where we would take seats. Our escorts by then would be standing behind our designated seats. 

I noticed that many of the other boys were not making a serious effort to look like girls. Most hadn’t bothered to shave their legs. They walked like boys wearing dresses, which of course is what they were. There were a few, however, who really tried to look like girls and I knew they would be my toughest competitors. I surprised myself when I realized that I wanted to win, though I kept telling myself it was for Serena, who worked so hard. We could hear the principal asking the audience to calm down and prepare to greet the lovely ‘young ladies’ who would be entertaining them.

Then it began. The first ‘girl’ walked and when she was seated the second girl walked. Then she sat it was my turn. I suddenly got very nervous but Serena smiled at me and whispered “think of the fun we will have after this is over.”

I was grateful that she was escorting me to the judges and felt her loss when she stepped away. I curtseyed to the judges though I don’t know why I did that. It wasn’t something Serena had taught me nor told me to do. Then I introduced myself. The short speech was crafted by Serena.

“I am Emma. I hope someday to be a fashion designer creating new styles in women’s clothing.”

I smiled at them, finished my walk, and took my seat, crossing my legs at the knee as she had taught me to do. The boy next to me whose name tag said Ellen leaned over to me and whispered “Sissy!’. He hadn’t shaved his legs, nor did he wear a wig. I chose not to respond nor did I even look at him, but it did give me cause for concern when we returned to classes on Monday. Serena squeezed my shoulder and left her hand there which calmed me a little.

We watched the rest of the ‘girls’ parade in front of the judges and then we waited. They were going to pick 5 finalists to compete in the formal category. Serena was rubbing my shoulders and telling me not to worry. As she expected, I was one of 5 finalists chosen. We all left the stage and returned to the boys’ locker room, that is all except me. Serena had somehow gotten the key to the girls’ locker room and led me there where she had left my dress and shoes. We had ½ hour to get ready. Fortunately, the way Serena had planned it, all I had to do was change my dress and shoes which left her time to change my hair style and makeup. 

She took the scrunchie from my pony tail and combed out my hair so it fell in waves on my shoulders. The she darkened my makeup so it was more suitable for night time. She placed a small jeweled flower barrette on one side of my head.

"Just a little something to help you shine" she said.

She hugged me and air kissed me not wanting to ruin my makeup.

“Ok Emma, this is it. Knock them dead!”

We redrew numbers for the order in which to walk before the judges. This time I was 4th. With only 5 contestants left I didn’t think the order mattered much. We did not have to speak on this walk, just stop before the judges, turn slowly, and stand until they waved us on, each time getting applause from the audience.   

We sat there nervously waiting for the results. It took about 15 minutes before they were ready to announce them.

“The 4th runner up is Laurie”.

She went up to the judge and was given a certificate and a bouquet of flowers which was what each of the runner-ups received. Jasmine was the third runner up and Wendy was announced as the 2nd runner up. 

Serena squeezed my shoulder and whispered “Keep the faith sweetie.”

“The second runner up is Emily which makes Emma your winner and our first ever boy Beauty Queen!”

I couldn’t help it but I raised my hands to my face. I thought I was going to cry from joy. I really was happy to have won and did not consider any consequences that might occur. Serena hugged me tightly and if I weren’t wearing the panty girdle I would have had a very unladylike display. In addition to the certificate and a bouquet twice the size of the others, the principal placed a sash over me and a tiara on my head.

We took photos with the runners up, the student event staff committee, Ms. Chen and Principal Shultz both standing proudly next to me and Serena. They told me that tonight’s photo will be displayed proudly in the main office along with all the other historical moments in the school's history.

Afterwards, Serena took hold of my hand and led me around the gym one more time. Most people applauded and cheered but I did here a few derogatory remarks directed at me and questioning my masculinity.

The floor of the gym was cleared, a DJ set up his equipment and the music started for the dance. Mom came up to congratulate and hug me followed by Serena’s parents. Mom had the outfit I had worn for the first round and took it home with the certificate and flowers. I wanted to give her the tiara and my clothes from the final round but in my nervousness preparing, I forgot to give her my change of clothes and she forgot to grab them. 

So I was left to attend the dance still dressed as a girl. It was embarrassing since the other contestants had changed into their masculine attire.

Seeing my distress, Serena hugged me and told me not to pay attention to anyone accept her. She was happy to be with me as I was. And she ok taking the role of the boy.

"Miss Emma, I see that you are unaccompanied tonight. May I have this dance?" she playfully said to me extending her hand. 

During the slow dances she led having her hands on my hips and mine on her shoulders. Her eyes looked in to mine the entire time we danced. Eventually we got really close during the dance with our bodies tightly together, my arms now around her neck. She was not shy about sliding her hands down my waist and putting her hands on my ass, giving it a squeeze which caused me great discomfort inside my panty girdle. When I squirmed, Serena gave me a knowing smile.

Serena’s parents picked us up after the dance and took me home. As I got undressed and removed my makeup I vowed that it would be the end of my cross dressing. 

We met at lunch each day the following week but with finals coming up all our free time was spent studying. I was teased a lot during the next week at school, some of which was downright mean. 

After long mile run in P.E class, we hit the showers. I walked over to my locker to change into my uniform and saw a red thong taped on my locker door with a note saying: We know you liked it.

I didn’t have many friends to start with and the few I had seemed to distance themselves from me. Whether it was how  good I looked in my girl’s clothing, the curtsey I dropped in front of the judges, my androgynous hair style, or my eyebrows which were shaped a bit too feminine for my taste, I couldn’t tell. As far as I knew none of the other boys were harassed the way I was. It seemed now that my only friend was Serena who defended me when she heard me being harassed.

I was only able to get a job 3 days a week for the summer bussing tables at a local diner, but at least it gave me some spending money. Serena was taking an online course in dressmaking since she hoped to go into fashion design. That allowed us to be together 2 afternoons a week. We realized that we had never had an actual date so we rectified it when I asked her to go to a movie with me the day after finals ended. We walked out of the movie with no idea what it was about since our attention was focused on each other. 

When we got back to her house I followed her in expecting another make out session and I was not disappointed. We couldn’t seem to get enough of each other. When I got home after these sessions I made a beeline for the bathroom to relieve myself, if you get my drift. 

Then the afternoon after she finished her course was quite a bit different.

“Mark, I have a big, big favor to ask.”

“You know I would do anything for you, Serena.”

“Are you sure?”

“I love you Serena, whatever it is I will do it if it is in my power.”

“Thank you, thank you, thank you. I love you too.”

She gave me a big hug and kissed me passionately. Then she took my hand and led me to her room. She started pulling clothes from her dresser. She pointed to a dress that was hanging outside her closet.

“I made this dress for my friend and I need to hem it. It fits me, but I can’t hem a dress while I am wearing it. Will you please put it on so I can hem it. Pleeease!”

That was not what I expected and it was not something I really wanted to do again, but I did say I would do whatever she wanted. When I looked into her pleading eyes I could not say no.

“You will have to wear the underwear also so the dress will hang right, but you know that already.”

I went into her bathroom, removed my clothes and put on the panties and bra she had given me. And I got an erection when I slipped on the panties. At that moment she knocked on the bathroom door and told me to open it a crack so she could give me something. When I opened it she handed me a panty girdle and I could hear her giggling.

When I came out of the bathroom she slipped the dress over my head and I threaded my arms through the sleeves. She zipped it up in the back.

“Now you are my prisoner!” she giggled and hugged me from behind.

It was a very short yellow dress with blue flowers, short sleeves, a round neck, and a short flared skirt. Then she gave me the wedge sandals I had previously worn and had me stand on a step stool so she could pin it.

After she pinned it, she unzipped me and I took off the dress and gave it to her.

“You can sit around in your underwear or I can give you another dress to cover yourself. It will take me about 30 minutes to hem the dress and then you will have to try it on again so I can see if it fits right. It doesn’t make sense for you to change back yet. I wasn’t anxious to put on another dress, but it was better than sitting around in a bra and panties, not to mention the panty girdle. She gave me the white shift that I had worn previously.

I played on her computer for about 40 minutes when she announced she was finished hemming the dress. I switched dresses and she had me stand on the stool again. She took some measurements and pronounced the dress finished. She held out her hand to me while I stepped down from the stool. Before I could say anything her arms were around my waist and we were kissing. I loved kissing her and almost forgot how I was dressed. She took my hand and led me to her bed and told me to sit. She sat down next to me and we resumed our kissing. I felt her hand on my knee working its way up under my dress. I was erect under the panty girdle and wanted desperately to remove it. As if she were reading my mind, she pulled at the waist. I lifted my butt so she could pull it down but only as far as my knees, effectively locking my legs together. She pushed me down on my back and lifted my legs onto the bed. Then she climbed on top of me and sat on my waist. She looked down at me with a big smile on her face.

“Oh my pretty Emma, what I am going to do to you!”

She slid down to the end of the bed and picked up my dress. Then she started rubbing me through my panties. She knew just where to rub and I got even harder.

“I won’t last long. Are you sure you want to do this.”

“Oh yeah! You are the best boyfriend ever and I want to reward you.”

She pulled my panties down freeing my cock. She stroked it a few times and I could feel it was wet. To my surprise (not that I wasn’t surprised already) she leaned over and put my cock in her mouth and started to suck on it. I had never had a blow job before. In fact she was the first girl to ever touch me below the waist. Feeling her warm mouth on my cock I thought was as good as it gets.

Serena's best feature was her smile, the way she smiled would light a room and now her mouth was firmly around my cock taking it all in. 

She looked up at me with her charming eyes and smiled, knowing she had complete control of my pleasure.

“I can’t hold back much longer” I said giving her a chance t release me if she wanted. 

“Mmmmm,” was all she replied.

And then I came. It was by far the best orgasm I ever had. Of course all previous ones were by my left hand. To my surprise she swallowed all of it. Then she crawled up the bed, lay down next to me and kissed me. I could taste myself but I didn’t care. We smooched a bit and I reached down to unbutton her shorts thinking I would repay her. She put her hand on mine to stop me.

“No, Emma. You can do something else for me.”

She sat up and pulled off the top she was wearing. Then she unbuckled her bra and tossed it on the floor. She had small perky breasts. 

“Why don’t you play with these Emma?”

I had never touched a girl’s breast before and I was anxious to do so now. I caressed each one in turn and she moaned and kissed me more.

“Tweak the nipples!"

I followed her order and she moaned even louder.

“Now suck on them!”

I did not need further urging and I found I could almost fit the whole breast in my mouth. I ran my tongue over the nipple and she jumped. I switched from one breast to the other and she liked that.

“Bite the nipple gently Emma.” she ordered.

After awhile she told me to stop, saying they had gotten too sensitive. She rolled on top of me and we made out a bit longer. She glanced at the clock and quickly got off the bed.

“My mom will be home soon. You better get changed”

I quickly removed the dress and the bra. I looked around but couldn’t see my boxers. She was in the bathroom and I realized I had left them there. I called to her.

“I can’t come out yet, just wear the panties home. You can have them. Hurry and get dressed, mom will be here very soon.”

No wanting to be caught wearing only Serena’s panties, I quickly put on my clothes over the panties. I heard the front door opening.

“Serena, your mom is home. What should I do with the clothes?”

“Throw them in the closet. I will sort it out later!”

I did that and sat down at her computer, brought up a game just before her mom came in.

“Hi Mark. Nice to see you.”

“Hello Mrs. Brogdon. It’s nice to see you too.

“Where is Serena?’

“In the bathroom. I’m just waiting for her to come out so I can say good-bye.”

She smiled at me and went to her bedroom. Serena came out and we kissed. I felt like I was walking in the clouds. We had taken another step in our relationship. I was in love with her and I was certain she felt the same about me. I could hardly wait to be with her again.

It was 3 days before we were able to get together again. When she opened the door she gave me quick a kiss on the cheek and seemed unsettled, maybe a little scared. 

“Please sit. We have to talk Mark.”

I got very nervous. 

“What is going on? Are you breaking up with me?” I asked.

“Oh no! Never! But I hope you will still want to be with me after you hear what I have to say.”

“I can’t imagine that anything you say would want me to leave. “I said. “I love you Serena!”

“And I love you Mark! But I haven’t been completely honest with you. I probably should have told you this before and I’m sorry for keeping it from you.”

“What are you talking about?”

“I’m a girl.”

“Of course you are” I laughed.

“But I am in the wrong body.”

“I don’t understand.”

Serena took a deep breath and then let it out.

 “I was born a boy.”

“You’re teasing me.”

She said nothing, looked away, lifted her skirt, and pulled down her panties.

Then I understood. She had a small dick and 2 tiny balls where I would have expected to see her pussy. I was speechless as all kind of thoughts went through my mind. She quickly pulled up her panties and smoothed out her skirt.

“I have known I was a girl as long as I can remember. I liked playing with dolls, dressing in pretty clothes. My parents took me to a psychologist when I was very young. I was diagnosed as being transgendered. I started on hormones before puberty so I have been going through puberty as a girl, hence my breasts. I can’t have surgery until I am 18. At that time they will remove my boy parts and create a vagina. I will be able to have sex as a woman. I love you Mark. I don’t want to lose you. I hope you can accept me as I am.”

I stood there stunned, unable to respond. She had tears in her eyes. I heard what she told me but was having trouble processing it. All I could think about was all the times we kissed I was kissing a boy. I allowed a boy to give me a blow job and to masturbate me. I felt like my whole world had morphed into something I was not prepared for. 

“Please say something Mark” she begged. 

Tears were rolling down her cheeks and falling onto the carpet. She dropped to her knees and continued to cry.

“You really are a boy.” I said softly, in disbelief.

“I’m a girl!” she cried. “”I’m just in the wrong body, but I will have it fixed. You’ll see!”

Her tears continued to flow. I wanted to hold her and tell her it was alright but all I could think about was how I had been kissing a boy the whole time and I felt ill. I then made the worst decision in my life.

“I can’t do this Serena. I am not gay. Serena? Is that even your real name? Never mind, you don’t have to answer.”

I turned and walked out of her house hearing her scream “Please don’t leave me!” as I left thinking about how ‘she’ had lied to me".

To be Continued…..

*From the Karen Jensen:

 

I wish to thank Annabelle Brito for reviewing and making suggestions that have greatly improved the story. Her very significant contribution to this story can’t be overstated. The characters and events are from my perverted way of thinking. This is complete fiction and any resemblance to persons living or dead is pure coincidence. I hope you enjoy it. Please leave your comments, good or bad. I try to learn from constructive criticism. If you prefer you may email me at kjensen0611@gmail.com. I will answer all emails.