“Our next contestant tonight for the title of Miss Octoberfest is Miss Heather Honeywell,” the announcer’s voice came blaring over the loud speaker. “Miss Honeywell is just a sweet, innocent sixteen years old. Yes fellows, she’s sweet sixteen and never been kissed. When she is not sitting at home studying, waiting for her favorite young man to call, she can be found on the sidelines of the football field cheering our boys on to the state title.”
“Join your hands together and see if we can get her to come on out. She seems just a little shy. Let’s make her feel welcome.”
As the announcer spoke, I went into my act; first sticking my head out, acting a little shy, and then finally I began to walk down the aisle of the local gymnasium – dressed not in a long gown as the other men in this crazy competition. No, I had chosen…well chosen was not the right word…it had been decided for me that I was dressing as a high school cheerleader.
How in the world did this happen? How in the fuck did I end up dressed as a girl walking down this aisle in front of all these damned people?
Those were just a few of the thoughts going through my mind as I sashayed my butt down the make-shift runway.
I was swinging my hips down the aisle trying to act in full cheerleader persona; trying to work the crowd up, shouting in my best female voice, “Give me an H!”
The crowd cheered, yelled and roared as we spelled out H-O-N-E-Y-W-E-L-L.
After my cheer was done, I continued my walk to the make-shift stage at the end of the gym, and stood with the other men who had taken their walk before me. We ranged in ages from 16 to over 50. Some of us were dressed as public figures, while others chose the typical beauty queen gowns, and then there was me – the cheerleader.
I was decked out in a brunette wig, complete with two pony tails tied with red ribbons and wearing a tight school sweater and short tartan-print skirt. Underneath I had on red panties covered with our school’s red bloomers. What a sight I was. I stood there with the other guys as we watched the other twenty-two guys make their walks into the gym. They too had been conned into doing this somehow. I couldn’t for the life of me imagine that any of them chose to do this voluntarily.
So how did this sixteen-year-old boy end up on that stage dressed as a high school cheerleader?
It all started during the summer. My girlfriend, Tammy, and I were hanging out at her best friend’s house one night after a men’s softball game. We all lived in the same neighborhood. My house was on the corner of our road. My girlfriend lived across the street from me, and her best friend, Michelle, lived on the corner of the next block. We often chose to meet at her best friend’s house as they had the only pool in the neighborhood, and had plenty of room for our whole group of friends. Their parents, especially Michelle’s mother, Gail, often hung out with us as well.
That night it was just me, Tammy, Michelle, Gail, and Michelle’s brother, Russell, who we all called Rusty. We were eating chips, salsa, onion dip, and other things while talking, watching television and playing poker. We were not playing for money, but just for fun.
Gail had recently been chosen to organize our town’s annual Octoberfest festivities. This was and still is a big festival in my hometown complete with fair, craft show, yard sales, cake walks, music concerts usually featuring a new country artist and even a big fancy ball. The money raised supported the chamber of commerce; some went to the schools in the form of scholarships, and much of it to local charities.
Gail was telling all of us about something new they were going to do. It was to be a beauty pageant. Rusty and I kind of hooted and catcalled, saying we couldn’t wait. We even encouraged Michelle and Tammy to sign-up. Both of them said there was no way.
“Is there going to be a swimsuit competition, Mom?” Rusty quickly asked.
“Well Rusty, it’s not exactly that kind of pageant,” Gail replied. “In fact, instead of Michelle and Tammy, I need you and Mike to be contestants. It’s a male beauty pageant. You know, the kind where the men dress like women. The committee thinks it would be a great deal of fun.”
“To hell with that,” Rusty said.
“Language Rusty, you know you are not allowed to talk like that here,” Gail scolded him.
Rusty was going to be a senior when school started back. He was about to turn eighteen and I’m sure felt more of an adult than he actually was. As my grandfather used to say, he was a little big for his britches at times.
Rusty and I played on the school’s baseball team together. That summer he and I had been chosen to play for a men’s softball team. Rusty was one of our star players.
He had recently gotten in trouble on one of our out-of-town games. He and a few other boys were caught drinking. He had been suspended from playing for awhile. So that night he sat in the dugout. We managed a slight victory, but we really missed Rusty on the ball field.
Even more of a disappointment, I had not gotten to see Rusty naked in the locker room after the game.
Since the town did not have a field for our team, during the summer the team rented the school’s ball field, and we got to use the locker room facilities as well. It was always good to shower and change after the game especially if we had something planned to do. It saved a trip home.
I was the youngest guy on the team, and not as good as the others. I often sat out the games in the dugout. I volunteered to be the equipment manager for the team. I took care of the equipment, cleaned up the locker room, washed the towels, made sure each of the guys had clean towels after the game and plenty of water to drink during it. So even when I didn’t really get dirty during the game, I still had a reason to be in the locker room. It was a nice perk.
Rusty was one of the finest specimens I got to enjoy. Of course I was clever in doing it. I was sneaky and only stared when I was sure no one was looking. Rusty was 6’4”, 189 pounds and had dark brown hair and green eyes just like his sister. Rusty and his sister were both blessed with a dark complexion. They didn’t have to tan like the rest of us. Rusty had a full-body, perfect golden tan all year long. I think somewhere in their lineage, they were of Italian or Greek heritage.
Rusty had a light splattering of dark brown hair on his chest, stomach, arms, and even thicker on his legs. He had a wonderful happy trail that began at his navel and traveled right down to his neatly trimmed and slightly curly pubic hairs. His beautiful bush highlighted the most magnificent uncut cock. His cock, when I usually saw it, rested nicely on a big set of balls which were also blessed with beautiful dark brown hair. His cock was also a nice size. It usually hung at about four inches long when soft. The skin on his cock did not fully cover the head of his cock. You could always see the slight tip of the head reveal itself. I had only seen him erect a few times. Fully erect he was about six and a half inches but was nicely plump; it was perfection as far as I was concerned.
Yes, if you have not figured it out by now, even at the ripe young age of sixteen, I knew I was bisexual. I was still a virgin that summer. Tammy and I had talked about it, but she wanted to wait until that fall when she turned seventeen. We made out heavily that summer, and came close many times, but we always stopped. Even though I wanted Tammy so bad, and found her to be hot, I still couldn’t stop looking at the guys in the locker room that summer.
When I masturbated, I often thought of Tammy but I also many times thought of Rusty or one of the other guys. In fact even when I wasn’t masturbating, I thought of both sexes. That night as we sat there talking, playing games, and hanging out, I constantly snuck glances at Tammy, Michelle and Rusty. Hell, I even looked at Gail and ogled her.
After Rusty emphatically assured everyone that there was no way in hell he would ever be in the male beauty pageant, his mother turned her attention to me. I was just as emphatic as Rusty. Sure, I looked at guys and got turned on. At the same time, I wasn’t a woman and I wasn’t into dressing and acting like one either. Other than wanting to do sexual things with men, I had no desire to be a woman. There was no way I would ever do that. I also felt sure in my mind that even though I acted as masculine as any other guy, if I did what Gail wanted, everyone in town would automatically know that I liked guys. They would all think I was queer.
Gail was having it no other way. To make matters worse, she enlisted Tammy and Michelle in her campaign to get both of us or at least one of us in the Miss Octoberfest pageant. One of us was going to flaunt our stuff on that runway. There was going to be no ifs, ands or buts about it.
Finally they issued a challenge. It was to be a poker game. Gail against me and Rusty, and whichever one of us lost the game, he had to be in the pageant. If Gail lost, then we were both free. As part of the challenge, if Gail won, the girls got to choose our name, our outfit, do our makeup; we had no choice in the matter. We had to do whatever they chose. We all shook on it and agreed to the terms of the bet.
I could bore you with the details of the game, but I won’t. Never in my lifetime have I played a worse game of poker than I did that night. It was pitiful. I was determined that Gail or someone had fixed the cards. I guess it was just destined for me to lose. Not only did I lose to Rusty, but we both lost to Gail. So I was now going to have to grin and bear the consequences. To make matters worse, I wasn’t even going to get to choose what I wore when I received my punishment. The girls won the right to dress me any fucking way they wanted. I had to go along with it. I was from the South, and a good southern gentleman always keeps his word when given to a lady.
The next few weeks were filled with a flurry of activity with a great deal of laughter for the girls. They were also filled with much emotional turmoil for me. I kept imagining all the worse possible scenarios of how my public shame was going to play out.
One night, shortly before school started, we were all hanging out again when the subject of my undergarments for this event came up. Gail immediately said that I had to have the perfect 36 bust size. Tammy and Michelle instantly agreed. That led to me standing embarrassed before them as they measured me for my bra. They concluded with a little padding I could pull off a 36. Rusty insisted it had to be a D cup. Yes, now Rusty was in on planning my public shame.
When they began to talk about my panties, I put my foot down. I was wearing my white briefs or nothing. After some good natured ribbing and many protests that white briefs would not work for what they had planned, we reached a compromise and I would take care of buying some red bikini underwear. Gail insisted they had to be red.
The next few weeks proved to be exciting ones; the highlight being the loss of my virginity. I ended up losing my “normal” virginity first. I call it that because it is what was considered normal in the town where I lived. It was what was preached to us from an early age. Normal sex only occurred between a woman and a man.
My first time happened in September after school started. Tammy, Michelle and I started our sophomore years, and Rusty started his senior year. During one of our football games, Tammy and I slipped away and slipped into the back seat of my orange and white 1969 Ford Mustang. I had just gotten the car for my sixteenth birthday that summer. It was a gift from my parents. It was the car I had always wanted. I didn’t want a new car. I wanted a classic. I loved that car, but that night the car became even more special to me.
The night was cold. It was an unusually cold fall that year. Tammy and I were wrapped up in a blanket. We were your typical hormone-fueled, sixteen-year-old teenagers. Between stealing kisses and groping one another under the blanket, we were both worked up. I was so shocked when Tammy suggested we go to the car. It was at a crucial moment in the game. We needed this win. I told her to wait a little longer. At the time, I thought she was just cold.
After a bit she leaned over and whispered in my ear, “Remember what I told you I wanted to do when I turn seventeen? Let’s do it now.”
I looked puzzled for a moment and then nodded. “Really?”
She nodded her head an emphatic yes, smiling from ear to ear.
“But that is still almost two months from now.” I said.
“I know but I want it now. Let it be a belated birthday gift to you.”
Who was I to not accept a gift from my girlfriend? I was already hard under that blanket from our earlier groping, but damn my cock jumped in my pants and got even harder. I almost unloaded in my jeans and briefs right there. I was sure everybody around us knew it too. I was flushed. I was hot. I was suddenly sweating. One thing was for sure, I couldn’t wait to get to my car.
I stood up. To hell with the football game. I was sixteen and I was going to get my rocks off. I grabbed Tammy’s hand and we took off. I held the blanket in front of my erection the whole way to the car. I was still sure in my mind that everyone saw it and everyone knew what we were going to do.
Fuck it, I did not care.
Tammy and I got into the backseat of my Mustang right there in the parking lot of the high school. We didn’t even get fully undressed. She pulled down her pants and panties to her ankles. I grabbed them and pulled them off, laying them in the floor. I unzipped and unbuttoned my jeans as quickly as possible. I pushed both my jeans and briefs down to my knees at the same time. I still don’t know how I did it, but somehow I found her opening very quickly and I pushed my cock into her. She was tight. Her entrance resisted at first, but finally gave way to my achingly hard dick.
I would love to tell everyone I know that it was the fuck of the century. Well it was for me, but poor Tammy. I almost shot my load just as soon as I entered her tight passage. Thankfully I didn’t, but I didn’t miss it by much. I thrust into her about four times, before I began cumming. I shot a big load inside of her. My load was much more impressive than my technique. When I stopped shooting, I collapsed on top of her panting, reveling in the fact that I was now a man. I was the big man on campus. I was the stud. I had fucked that girl better than she was ever going to be fucked in her life.
Then it happened. I realized what I had just done. I had come inside her and she didn’t stop me. I began to panic. Oh shi
t, I thought to myself. She is trying to trap me. She wants to get pregnant and have my baby.
I pulled out and began to ramble. I was talking but I wasn’t making any damn sense.
The wonderful, more mature Tammy calmed me down. She was on the pill. It was all okay. She wanted this as much as I did. We began to make out again, and ended up going at it one more time.
That second time was thankfully longer. I will never forget that just as I shot my second teenage load inside her, the crowd in the stadium exploded with a mixture of shouts, whistles, yells and applause. I found out later, our team had just won the game. In fact, Rusty had made the winning touchdown. How wonderful that the second time a young teenager gets his rocks off inside a tight pussy, he gets a standing ovation. I laughed at myself for even having the thought.
In the weeks that followed that first encounter, Tammy and I had several more encounters, each better than the other.
A few weeks after losing my “normal” virginity, I lost my other virginity. Yes I lost my anal cherry to a guy. Not just any guy. I lost it to Tammy’s older married brother. I was sixteen, and I knew I was bisexual. I loved women. I loved looking at and being with them. At the same time, when I watched porn, looked at porn magazines or was in the locker room with the guys, I was aroused by the naked guys as well. My time with Tammy’s brother happened with a weird chance encounter around the first of October, just a few weeks before Octoberfest. I will save that story for another time.
I was walking with a new sense of pride in my step after my encounters. I felt I was fully a man.
About two weeks after being fucked by Tammy’s brother, my day of shame arrived; it was the day of the Miss Octoberfest pageant. It had been decided that I would dress at Michelle’s house. I packed a bag of clothes and some toiletries so that as soon as this thing was over, I could change and get back to just being me again. The last item I tossed into the top of the bag was my new red bikini briefs. I threw the bag into the back seat of my car, and drove down the street to meet the others.
When I arrived, Rusty, Gail, Tammy and Michelle were waiting for me as well as Paul, Rusty and Michelle’s dad. I was so embarrassed. Of all the people that were going to witness this, I did not want it to be Paul. He was one of the most macho men I knew. I knew that he would never think the same of me again.
“Come on back this way Mike,” Gail said and started to walk toward the master bedroom she shared with Paul.
I followed her with the rest of my torturers following close behind. When I walked into the room, my eyes went straight to the bed. There laid out in front of me was my outfit for the night. Lying there neatly was one of our school’s cheerleader sweaters, white with a big lion on the front. Lying below it was a short cheerleader skirt, red and blue tartan print. Some other things were arranged on the bed as well; one of them being a red lacy bra. Sitting on the nightstand next to the bed was one of those white foam wig heads featuring a long-haired brunette wig.
I stood there speechless for just a few moments, letting my eyes scan the items.
“Oh, hell no, there is no fucking way I am going dressed like a cheerleader!” I exclaimed and started to walk out of the room.
Tammy and Michelle were trying to calm me down while Gail was constantly reminding me of my language.
As I calmed down, I was quickly reminded of our agreement. We all walked back into the bedroom. It was decided that Paul and Rusty would help me get dressed, and then the ladies would take over and do my hair and makeup.
The girls went out into the hallway and closed the door. I tossed my bag on the bed and sat down to take off my shoes and socks. I was going very slowly, trying to put this off as long as possible.
After a few minutes, Paul spoke, “Okay buddy hurry this up. The sooner you do this part, the sooner you get it over with.”
I had played sports for years as well as being in high school gym class for two years now, so undressing in front of two guys was no big deal. I was finally down to my briefs, and even though I had undressed in front of many guys before in the gym, I was suddenly embarrassed when I realized I was going to have to slip my briefs off and put on the red bikini ones. I thought that maybe Paul and Rusty would realize this and step out. They didn’t. I considered slipping into the bathroom, but didn’t want them to think I was embarrassed.
“Come on boy,” Paul said. “It’s just us guys here. You don’t have anything we don’t have.”
I took the red bikinis out of the bag, and turned around with my back to Paul and Rusty. I lowered my white briefs, and pulled the red ones on.
I guess Paul had not been let in on this part of my wardrobe. He immediately wanted to know where my red panties were. I tried to tell him I refused to wear any, but he said this wasn’t going to work.
Paul went to the door, and he and Gail had a whispered conversation through a crack in the door. All this time Rusty stood there looking at me. I was straining to try and hear what Paul and Gail were saying. He finally said okay and shut the door.
Paul walked over to the dresser, and began rummaging around in one of the drawers. Finally he found what he was looking for. He held up a pair of red, very lacy, very skimpy panties.
I started to protest, but I looked around at the other stuff I was going to have to wear. I thought to myself, Oh fuck it. Those panties weren’t going to make my shame any greater. At least with them, only Paul and Rusty would ever see them.
I took them from Paul, noticing that Rusty had one of the most evil grins on his face. He was fully enjoying my embarrassment.
I turned back around, took off the red bikinis, and pulled up the panties. It was a slow go. They were tight. I had to work hard to get my junk arranged in them. Let me tell you, my cock and balls were not arranged very comfortably at all. I was so embarrassed. To make matters worse, having to touch myself so much to arrange things, I had gotten a little excited.
I finally felt comfortable enough to turn around. When I did both Paul and Rusty were staring. I glanced down and could swear that both of their bulges looked bigger than they had before. Yes, even during all the anxiety over my shame, I had stolen glances at both at various times that day. Even in times of embarrassment, a man still has time to think about getting some. Yes, I was an equal opportunity pervert; I noticed how great the girls looked that day too.
I stood there in front of Paul and Rusty for what seemed like forever, neither of them saying anything at all. I couldn’t stand it any longer.
“What?” I asked. “What the hell is wrong?”
Paul was the first to speak. “It’s nothing. The panties look great. Don’t you think so Rusty?” he said looking over at Rusty and then back at me.
“Yes, Dad, I agree with you there. But…..” Rusty said before I interrupted.
“But what….what’s wrong?" I asked very confused.
Paul said, “Just a minute,” and walked into the master bathroom.
He came back out carrying a razor and shaving cream. He laughed and said, “It’s all that hair. It just doesn’t go with the panties. It’s got to go. Don’t you agree Rusty?”
Rusty shook his head in agreement, and said, “I don’t know about you Dad, but I’ve never seen a cheerleader with such hairy legs.”
They both laughed out loud.
I began to protest. Paul just stood there shaking the razor and shaving cream tauntingly.
A loud knock on the door stopped all the chatter. It was Gail.
“Okay, you two, quit taunting Mike. The pantyhose on the bed will hide his hairy legs. Now get your asses moving. We’ve got to get this show on the road,” she yelled through the door.
All at once all of us yelled, “Language! Watch the language!”
Gail just said, “Shut up.”
Inside the bedroom, Paul put the razor and shaving cream down. I moved to the bed and picked up the red bloomers. I wasn’t even thinking. I started to pull them on when Rusty reminded me that the pantyhose needed to go on first.
Paul and Rusty watched as I began to slowly transform myself into a sixteen-year-old girl in front of them. I pulled on the pantyhose, struggling the whole time. I could not figure out how women did this all the time. I then pulled on the bloomers. I stood there looking down at the bra. I was dreading this one.
I started to pull it on and for the life of me I couldn’t figure out how women fastened these things. Before that day, my only experience with one of those was either staring at a girl in one or unfastening Tammy’s so that I could get to her hot tits. I still wasn’t an expert at getting a girl out of one, but it was still easier than getting myself into one.
Paul came over to me and said, “Here let me help you with that.”
Paul fastened it. It was loose. I turned around and there I stood. I had to look a sight. Here I stood in front of them -- a hairy-chested man, dressed in a bra with no padding, red bloomers and brown flesh-toned pantyhose.
Rusty confirmed my suspicions. “Damn you are one ugly flat-chested girl,” he said.
Paul said, “Give me a minute and I’ll take care of the flat-chested part.”
Gail and the girls were listening closely outside. I could hear the occasional snicker and laughter from them.
“Do you guys need any help in there?” Gail asked.
“No dear,” Paul answered. “I think we can take care of giving him breasts. I have always wanted to give you bigger ones. I’ll just have to settle for giving Mike some.”
We all laughed.
Paul went to his sock drawer and with Rusty’s help, they began to wad up socks and began to create me a pair of perfect 36D bosoms. This was followed by both of the guys starting their ribbing. They stood there teasing me and playing with my new set of fake breasts.
Paul yelled through the door at Gail, “Honey, you are definitely going to have to get a pair of these now.”
Before Gail could say anything, Michelle yelled out, “Ewwww Dad. We don’t want to hear this.”
Gail replied, “Grow up Michelle. You and Rusty wouldn’t even be here if Paul and I never had sex.”
“Mom,” Michelle yelled.
Inside the bedroom, I continued my transformation. Finally I stood before Paul and Rusty wearing my sweater and skirt.
“Well you’re starting to look better. A little makeup and some hair, you might make an okay looking girl,” Paul said.
Gail, Tammy and Michelle entered the room.
“Okay, Paul and Rusty, you two get out. We girls have got work to do. It sure took you three long enough.” Gail exclaimed.
Paul put his arm around Rusty’s shoulder. “Okay let’s go son. We did the hard work. We’ll leave the petty stuff to the ladies.”
Gail picked up her shoe and threw it at Paul as he and Rusty walked out.
The ladies sat me down in a chair. I spent the next hour being plucked, picked, poked, rubbed, snipped, and painted. They trimmed my eyebrows, snipped and plucked any stray hairs on my face, patted my face down with powder, and painted me fully with eye shadow, lipstick, eye liner, and mascara. You name it. If it has ever been created for a woman to put on her face, I got it put it on my face that day. Right down to the fake long eye lashes. During the whole process, I was not allowed to look toward the mirror once.
Finally, they placed some type of little cap on my head, and donned my head with my new shoulder length dark brown hair. Gail finished it all off by dividing and tying off both sides into a pony tail.
The ladies stood back and stared at me.
“You look good,” Gail said. “You’re a shoo-in to win this.”
Tammy and Michelle agreed with her. Gail then yelled for Paul and Rusty.
When the guys entered the bedroom Paul jokingly wanted to know where Mike went and who their new sexy friend was.
They all laughed but I still wasn’t finding any humor in all this.
Gail looked at Paul and Rusty and asked what they really thought.
“If I didn’t know it was Mike under there, I would never know.” Rusty said.
Paul continued in his joking. “If I was a little younger, and you were a little older, you and I would be getting our own room,” he said.
Gail hit him on the arm, and the girls once again voiced their disgust. Gail told him to get out. She then looked at Rusty telling him to get her car loaded. She had to get running.
Paul and Rusty walked out of the room. I heard them talking as they walked.
“Dad, I can’t believe you said that. That’s Mike…a guy, you know…under all that makeup and clothes,” Rusty said.
“Hey, as long as he didn’t speak, in that getup I would never know.” Paul laughingly said.
Gail yelled for him to shut up again.
I interrupted all of them. I still had not seen myself. They finally allowed me to stand up. I stared in the mirror. I could not believe what I was looking at. I wondered where in the hell the real me was. Someone was playing a trick on me. Where had the real Mike gone?
As I stood there the girls frantically tried to get everything together. Gail told them she had to go. It was up to Tammy and Michelle to work with me for the next hour.
“Mike looks great, but you have to teach him to sell it,” Gail instructed.
“Go on Mom, we’ll make sure he has everything right,” Michelle told her Mom.
The girls worked with me the next few hours of the afternoon with some assistance from Paul and Rusty. Most of their help consisted of catcalls, whistles, and the like.
The first thing the girls did was reveal what they had chosen for my contestant name. Tammy and Michelle just liked the name Heather, as they were both big fans of the movie Heathers
. They all knew how fond I was of the Porky’s
trilogy of movies, and that I especially loved the “Lassie” scene from the first movie. So they combined both and I was to be Miss Heather Honeywell.
I was taught to walk like a girl. They instructed me on how to lead my cheer and work the crowd up. They introduced me to my pompoms.
Finally convinced I had everything down, Paul and the girls had to run to the festivities to help Gail. Tammy decided she would drive my car so that she and I could use it later. I didn’t like the idea at first, but I had not even thought about driving with this garb on. It was decided Rusty would drive me to the gym. Besides, Rusty had keys to the gymnasium and we could park on the backside of the school. After everything was over, I could slip out, get my bag out of Rusty’s car, and get back to the real me inside the boy’s locker room.
Rusty and I watched some TV and talked for about an hour. I did not want to go outside and to the festivities until it was the exact time to be there; the fewer people that saw me like this the better. It was going to be bad enough having to be seen by the hundreds or so that would be at the pageant.
So that is how I ended up on that stage in front of hundreds of men, women, and children dressed like a high school cheerleader.
The other men and I stood there watching, proudly displaying our perfect pageant smiles, and watching our fellow contestants strut their stuff down the walkway. Finally we were all on the stage.
Our vice-mayor, Jack Stewart, volunteered to act as the announcer and emcee for the night. He instructed us to take another walk around the stage so that the judges could choose their top ten.
One by one we each took our walk, and tried to sell ourselves to the crowd and, most importantly, to the judges.
Then it began. Jack was handed the envelope and we were narrowed down to ten. I was the fifth name called. I stood there as he called each of the names before me. I was desperately hoping that my name would not be called. I wanted this all over with. I took my place in line with the other men, and listened for the next five names to be called out.
Our fellow contestants who were not chosen were cheered on by the announcer and crowd. As they walked off, I stood there wondering to myself which was worse. I couldn’t decide if it was worse to embarrass yourself this way and have to walk off the stage a loser or was it worse to have to stand there even longer, letting your humiliation continue. In the end it really didn’t matter. There were at least a thousand cameras as well as video cameras capturing our disgrace. I became even more embarrassed as I stood there. I had never thought about anyone taking photos or videotaping this.
My fellow contestants and I braced ourselves for the next part of our circus of humiliation. It was the question round. I wasn’t too worried about this round. The girls had prepared my answer beforehand. No matter what I was asked, I was to answer the question the same way.
I stood there as each of the four guys before me took their turn. I watched as they played up the audience, tried to answer with something funny, and did their best to playfully flirt and win the judges over. To tell you the truth, I was only focusing on what I was doing, and looking at the crowd. I was trying to find Tammy. I do not remember if I even heard the questions and answers before me or not. For that matter, I didn’t even hear the ones after me.
The only thing I remember was hearing my name being called to step up to the microphone. I playfully paraded myself to the microphone, using the sexy walk the girls and guys taught me. I gave my best come-hither and flirty look and said hello to Jack Stewart and the audience. As I walked the crowd clapped, cat called, whistled, and even one guy somewhere in the audience yelled, “Take it off baby!”
The moment arrived and I was asked my question by Jack. “Miss Honeywell, if you win the title of Miss Octoberfest, what difference will this title make in your life?”
I batted my eyes, and smiled my most seductive smile at the audience and Jack. In the sexiest dumb girl voice I could muster up, I spoke, “I don’t know about that one Mr. Stewart. I just want to do my best to end world hunger and bring world peace.” I finished off with my little giggle.
I sashayed my hips back to my place in line and waited. Finally each person had their turn. We smiled and carried on as the judges tabulated their votes. Finally Jack was handed the envelope, and we were one step closer to this all being over.
“Let’s give all of these fine contestants a hand folks,” Jack began. He paused as the audience cheered us all on.
Then he began. “Our fourth runner up tonight is Miss Elly Mae Clumpett.”
I watched as one of our town’s most popular volunteer fireman made his walk to his position on the opposite end of the stage, accepting his sash and flowers from our mayor.
“Our third runner up is Miss Mae Westover.”
Mae Westover was one of our town’s longest running policemen. Everyone loved him. He accepted his crown and flowers, and had to throw in one more jab.
“Ya’ll don’t forget to come up and see me sometime, boys,” he said as he smiled and winked to the audience. The crowd roared with laughter.
Jack laughed and said to the mayor, “At least she didn’t ask you if that was a gun in your pocket or were you just happy to see her.” That kept the laughter going.
Once the crowd settled back down, Jack began again. “Coming in as our second runner up is Miss Marilyn Mornroe.”
The crowd broke out in applause as one of my favorite teachers, Mr. Johnson, strolled across the stage. He blew a kiss to the audience and giggled as he accepted his sash and flowers.
“Okay folks, just two more spots. Who is going to be our first ever Miss Octoberfest? First let’s see who our first runner up is.”
Jack went into the normal beauty pageant spill about how important the first runner up is; blah, blah, blah.
“Our first runner-up is…….Miss Heather Honeywell.”
There was a mixture of boos, applause and whistles as I smiled and walked across the stage to get my sash and flowers from the mayor. I gladly took my place with my fellow runners up.
We all stood there as Jack tried to build the audience up and build the tension. Finally he spoke.
“Here she is folks. Our first Miss Octoberfest is…….Miss Dolly Partone.”
The crowd roared and applauded, rising to their feet in a standing ovation. To me, there could have been no better winner. Miss Dolly was our high school’s principal. He was a man in his fifties and beloved by the whole town. He put on a great show for the audience right to the end. As I stood there, I couldn’t help but wonder how many socks he had stuffed in his bra.
Finally it was over. Well not quite. We had to meet for photos with the local paper. The local radio station wanted sound bites. It seemed to go on forever. I wanted to be back in my clothes. I wanted out of these shoes and out of these damn pantyhose. Most of all I wanted my briefs back. Every chance I got and thought no one was looking, I reached back to pull the panties out of my crack. They were constantly riding up.
We stood around for over an hour. People were constantly coming up and congratulating us. Some would say that I should have won or they hoped I would. I guess the group had done a better job on me than I thought. I got tired of people asking if I was really a man under there. I got so tired of both sexes poking my breasts to see if they were real. Some got overly flirtatious and copped a feel of my ass. I don’t know how often I got pinched. I just knew that my ass would be black and blue the next day.
The worst was when one lady who had obviously had a little too much to drink moved her hand the other way. She wasn’t convinced I was a guy until she copped a feel of my cock and balls in my panties. She was quickly rushed away by the security set up for the event.
The worst part of it all was that with all the touching and feeling, cat calls, etc. I got a little aroused. Thank goodness those panties, nylons, and bloomers were as tight as they were. The only thing about that was that as my cock lengthened and then relaxed, it would get in the most awkward positions in those panties. So not only was I pulling the panties out of my crack, but every chance I got I was adjusting my junk as well.
Finally my torture ended. Everyone was finished with us and I could slip away. Rusty, Michelle and Tammy had been nearby most of the time. I kissed Tammy and told her that I was going to go get changed. Then I had to get something to eat. Tammy said she would go ahead and order something and have it ready. I said great.
Tammy and Michelle went on their way. I asked Rusty for the keys. To my surprise, Rusty said he would go with me in case I needed any help. I told him that would be cool since I might need help with this damn bra, pulling on it at the same time. We set off toward the door and to his car.
“Congratulations man, you did a good job,” Rusty said for the first time.
I have to say it was relief to hear him say that. I was scared of what he must be thinking of me after the display I put on. “Thanks man. I am just glad it is over.”
“I bet. I know I would be. I’m just glad you lost that game instead of me.”
I just shrugged. Rusty just kept stealing glances at me. I wasn’t sure what was wrong or why.
We got outside, and started walking around the side of the gymnasium which was the dark side when the lights were out on the tennis courts. That night they were. As soon as we got away from the crowd, and in the dark, Rusty reached in the pockets of the jacket he had on and pulled out two beers.
“Here they have gotten a little warm, but I snuck these in. I figured you might need one.”
I took it, popped the top, and downed a big gulp of it. “Thanks bud. That hits the spot. I have been so thirsty for the last two hours.”
We kept walking. Not only had I been thirsty, but with all the up and down movement with my cock for the last hour or so, I needed to pee. I kept pulling at my panties as we walked.
“What’s wrong? You’ve been pulling on those panties all night. Are you trying to jerk off?”
“No man,” I said embarrassed. “I was hoping no one noticed, but I have had the wedgie from hell all night. Not just a wedgie in my crack either. These panties keep pinching my balls. I can’t wait to get out of them.”
Rusty just laughed. We kept walking. Finally we were behind the gymnasium and close to where we parked earlier. It was dark and I looked around. I didn’t see anyone. I was just a short walk from the door to the gym, but I couldn’t wait any longer.
I leaned against Rusty’s car, and slid my shoes and bobby socks off. Then off came the bloomers, and the pantyhose. I pulled the panties out of where they had been wedged. I couldn’t believe how wet they were. I knew part of it was sweat, but I also could feel that some of it was pre-cum. I guess I got more excited by all the touching than I thought. I got on the side of Rusty’s car, looked around again to see if anyone was looking. I didn’t see anyone. I pulled the panties down under my balls, took hold of my cock and let out a hot stream of piss. I lightly groaned at the relief.
Rusty stood by watching me. He never took his eyes off me during all this. I seemed to piss forever.
“Boy you did have to go,” Rusty said.
“Yes. Boy it feels so good.”
After what seemed like forever, my stream stopped. I shook the last drops off the end of my dick, and put it back inside the tight panties. I thought to myself, Just a little longer
I began to walk around to the opposite side of the car where my bag was. As I got closer to where Rusty was standing and I could see him better, I noticed that Rusty had his hands in the pockets of his jeans. I looked down at his crotch. It was dark but I could swear that Rusty was hard. It also looked like Rusty was using his hand to rub his dick inside his pants.
I shook it off. Maybe since it was dark, I was just imagining it.
I got to the passenger door on the driver’s side of Rusty’s car, opened the door and leaned in. I put the stuff I had already taken off into the car, and tried to find my tennis shoes and socks inside my bag. There wasn’t any light and I was having a hard time finding them. As I was bent over there, I thought sure I heard the sound of a zipper being undone. I looked around, but nothing.
I bent back over and continued my search. As I leaned over, I heard footsteps moving behind me.
“You need any help finding anything?” Rusty asked.
“Do you have a flashlight? It would sure be helpful about now.”
“No, I don’t, and sorry about the light in the car. I need to get that changed.”
As he was saying this, I felt him right behind me. Then I felt his hands on my skirt, lifting it up. He threw it up, letting it lay on the lower part of my back.
“Rusty, what are you doing?”
“Shh!!” he hissed. “Just go with it. I know you want it as bad as I do. I’ve just got to look at this ass again. I’ve got to look at these panties. Damn I’ve been so horny since I first saw you in them.”
I tried to pull away some, but he gripped and pulled me back to him. His hands began rubbing all over my panty-clad buttocks. He rubbed back and forth, up and down my crack, stroking my rosebud through the red panties.
“You don’t know how good your ass looks in these panties. I have been hard as a rock ever since you pulled them on.”
He took his hands off my hip and butt. He moved in closer and I felt it. I did hear a zipper. Rusty had his erection in his hand. He began to rub it over my panty covered behind. He felt how wet they were.
“See I know you want this. You are so wet. You need to be fucked in the ass. You want it.”
“No,” I moved my head at first. I wanted it but I was scared. I was scared to admit what I wanted. I was scared someone would see.
“It was just all those ladies touching me. I got excited. That’s all," I told Rusty, but also trying to convince myself.
Rusty kept on rubbing my ass. With everything that had happened that night, and now Rusty rubbing my ass, what did anyone expect. I couldn’t help but get turned on. I had lusted after Rusty for so long too. I had admired his naked body so often. At the same time, I realized how dangerous this was.
“Rusty, what if someone sees? Shouldn’t we go into the locker room?”
“No, I can’t wait that long. I am going to explode if we don’t do this now.”
He slid his cock, now wet with pre-cum, inside the leg band of my red panties. He began to thrust in and out. His cock was so wet. As he thrust, I could feel him leaving a trail of his juices on my buttocks and crack.
I was beginning to moan, and found myself thrusting with him. Back and forth I moved against him. I reached down and began to rub my cock which had grown to a full-fledged erection by now. Normally my cock when hard is between six and three-fourth inches and seven inches. I was so hard that day. I felt like I could erupt at any moment.
I kept wanting to protest. In my mind I was thinking no. My mind was saying we can’t do this here. But my body wanted this. I wanted this just as bad as him. I didn’t stop him. I didn’t stop myself. I kept going.
Rusty began to talk to me just like I had imagined him talking to one of his many girlfriends. I finally heard the words I had fantasized Rusty saying during those times I stroked my cock thinking of him.
“Come on. Let me fuck you in the ass. Let me butt fuck you,” Rusty moaned as he continued to thrust inside my panties.
I continued to thrust back into him even when I felt him pull his hard shaft out of my panties. I looked back and saw him wrap his hand around his throbbing boner. He began to stroke it. With the other, he once again rubbed my ass. He pulled the crotch part aside; he placed his finger against my rosebud. He held it there, gently stroking my tight bud. He finally slid the finger in and I let out a loud gasp of air and moaned. It felt so good.
“See you want it. I knew you did. Doesn’t it feel good?”
I moaned and nodded my head yes. I pushed my ass back onto his finger.
Rusty continued to stroke his cock. He continued to finger my now aching butthole.
“Come on baby. I’ll just put it in for a minute. If it hurts I’ll take it out. I promise. Let me fuck you in the ass,” Rusty begged. “Tell me you want it. I know you do. Have you ever been butt fucked Mike?”
I didn’t know what to do. I was still struggling. My arousal won out in the end. I nodded my head yes. I admitted my inner desires and what had happened to another person for the first time. I admitted that I wanted Rusty to fuck me. I was breathing heavy. I was panting.
“It was only once Rusty. But I liked it,” I said. “Fuck me Rusty. Just don’t come inside me. Pull out before you come.”
He promised he would. I bent over; Rusty moved behind me. He didn’t even pull my panties down. He spit into his hand, rubbed it onto his cock, and put his cock into the crack of my ass. In one deep thrust, he was inside me. He buried his entire cock to the balls and began to thrust all in one motion.
I went crazy. It fucking hurt. I screamed out. It felt like my ass had been ripped open.
Rusty kept thrusting, trying to quiet me at the same time. He had his hands on my hips and was holding me as I struggled to deal with the pain.
It was too much. I pulled loose and pulled myself into the backseat of the car, away from the hard cock that had invaded my anal canal. Rusty grabbed my hips and pulled me back toward him.
“No way boy, you are not stopping this now. I see the way you look at me in the locker room. I see you staring at my crotch all the time. You want this dick. And you know it. Don’t you?” Rusty pleaded, stroking his cock as I looked over my shoulder toward him.
He wasn’t making any attempt to stick it back in. He kept one hand on me, but I was no longer fighting. I was watching him stroke his cock. Even as dark as it was outside, it looked so good. I couldn’t deny what he was saying. I wanted it. It had hurt so much though.
Rusty saw that I wasn’t fighting him anymore. He let go of me and moved his finger back to my tight hole where he had buried his aching cock a few seconds ago. His finger entered me. He began to fuck me with it.
I began to clench my ass, massaging his finger with the insides of my canal.
“See I knew it. You want it don’t you? You want my big cock inside your ass. Just tell me and I’ll put it back in. I know you want it,” Rusty kept on.
I finally shook my head again. I was his and he knew it.
“Just go slow, Rusty.” I asked.
Rusty pulled my panties down my legs this time, pushing them all the way to my ankles. He pushed his pants and briefs down almost to his knees, and moved behind me. He hit the inside of my leg, sending the message to spread them wider.
I tried to give him what he wanted, but the panties would not allow me to move. I stepped out of them and spread my legs wider.
Rusty positioned his cock again, and pushed slowly into me.
I began to moan louder and louder as he slid into me deeper and deeper. He would slide an inch or two into me, then pull out and thrust back in. Each time he thrust back inside me, he went deeper.
I looked back over my shoulder to try to see his face. I couldn’t, but from the sound of his breathing and his moans, I knew he was enjoying this as much as I was.
Finally, he was fully inside me. He was thrusting in and out. His hairy balls were slapping against mine with each thrust.
He moved his hands up, and pulled me up toward him, and leaned against my back. He placed his hands on my fake boobs, and began to rub them.
“Oh, this feels so good. Your ass feels so good,” Rusty said.
He finally pushed me back down toward the seat, pushing my head against it. This thrust my ass up higher, opening it up more for him. Rusty grabbed my hips, and thrust harder and deeper into me. Each thrust jerked my body as he drove his cock into me over and over.
I could feel my balls tighten up. I could feel that tingle I always felt shortly before I came. I had not even touched my cock once since this began.
“I’m going to cum, Rusty. Fuck me harder, please.”
Rusty thrust harder and deeper. I took hold of the seat as best I could. He fucked harder and faster, using his right hand to occasionally smack my ass.
I squeezed my ass around his cock. He moaned as he felt the walls of my asshole massage his cock from the inside. Hearing him moan, as well as the constant thrusts against my prostate, sent me over the edge. I never even touched my cock, but now I was shooting onto the seat below me. I came so hard, and shot so much cum from my cock. I thought it would never stop.
Rusty continued to thrust into me, although it was made more difficult by how tight my ass was clamping down on his dick. My orgasm was all it took to set him off.
He yelled, “I’m cumming!!!”
True to his word, he pulled out of my ass with a plop, and grabbed his dick. He told me to turn around and let him shoot into my mouth. I turned quickly to see him stroking his dick. It was so hard. The veins were throbbing. I opened my mouth, and he kept stroking. A few more strokes and he began shooting his creamy load onto my tongue, face and into my mouth.
When he finished, he moved and leaned against the car. His cock began to soften, and point toward the ground as he stood there.
I had not swallowed a man’s cum at this point in my sex life, but I wasn’t sure what to do with the load in my mouth. I moved it into the back of my mouth and swallowed. It wasn’t bad. I used my fingers to clean off what was on my face, and swallowed it too.
I looked up at Rusty. “Did I get it all?”
Rusty stared at me, and said that as far as he could tell I did.
I didn’t even bother pulling my panties back on. I just picked them up and tossed them in with the rest of the stuff. Rusty pulled up his jeans and underwear. He zipped his pants and lit up a cigarette.
I tried to make small talk with Rusty. I could tell he wasn’t interested in talking. We walked almost in silence to the back door entrance to the locker room. Rusty opened the door and let me in. He told me he was going back inside and hang out with some friends. He said I could bring him the keys later.
I immediately regretted what had happened. Rusty and I had not been the best of friends, but I had always hoped we would be closer. I also worried that he would tell others at school.
Luckily the last part did not happen. For a few weeks things were tense when we ran into each other, but after a few months everything was back to the way it was before. We never did anything sexually again. I also never entered another damn male beauty pageant.
Rusty graduated, married, and moved away. Tammy and I later broke up. I’ve only see them a few times through the years. I remember what happened with both of them fondly. I guess Rusty regretted what happened between us, but I will always cherish the memory of the night I got screwed at the beauty pageant.
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<a href="http://www.lushstories.com/stories/crossdressing/screwed-at-the-beauty-pageant.aspx">Screwed at the Beauty Pageant</a>