Wrestling with Femininity

by Bolter

 

As a cheerleader in high school, I was always most interested in the wrestling matches.

The other cheerleaders, of course, were into the more popular sports like football or baseball. After all, those brought the biggest crowds, and the football players had the best bodies and threw the best parties.

But something about wrestling got to me. The uniforms they had to wear. The intense, passionate struggling. The desperation.

It was such a ritualistic, intimate sport to watch. Sometimes ruthless.

I guess that was when I was starting to really understand my desires to dominate men -- just to see them squirming and helpless.

And that's when I discovered Lucas.

**

Lucas was a freshman and came from a different city, so he didn't know anyone. He was terribly shy and kept to himself, but was an undefeated wrestler in his weight class.

He had a lithe, feminine frame and probably did not weigh more than 130 pounds. But he was strong.

I enjoyed watching his matches most of all. Because of the look on his face, and how hard he would breathe. He would keep his eyes shut sometimes, and I could swear he was in another world.

Sometimes I would notice him hard, too. And that was a huge turn-on for me. The other cheerleaders wondered why I had so much interest in wrestling matches; after all, we weren't even required to go.

I wasn't about to tell them that I was attracted to the younger, feminine little wrestler with the cute blonde hair and big blue eyes.

I also wasn't about to tell them what I would do to such a boy if I had him alone with me for just a few hours.

***

It was right before the nationals, and of course our wrestling team had gone all the way. The cheerleaders were all sitting together at Peg's house, and we were trying to come up with ideas for the spirit rally and other activities.

Mostly related to football, of course.

Peg came up with the idea of a kidnapping, and somehow I managed to take over the entire conversation. And somehow, I got them all excited about my idea. About a real kidnapping, something that would rock the entire school.

And more amazing was that I was able to talk them out of abducting the quarterback of the football team.

"He's too big. You think the seven of us can take him down?" I asked.

Lisa Johnson stuck out her chest. "Just show him our tits and when his mouth drops open, hit him on the head with a pan."

"Seriously, the wrestling team is about to go all the way. They never get any attention. Let's take one of them. A smaller guy."

They looked unimpressed.

"Then we can dress him up like a girl," I smiled. "And drag him out to the pep rally."

The others visibly brightened. "We can dress him up at a cheerleader!"

And from there, it was easy. Only one weight class would fit into one of our outfits.

"Lucas Daniels," I said.

They didn't care at that point. They were ravenous, they just wanted to dress up someone -- anyone.

And I got my wish.

***

When we kidnapped Lucas, he was terrified.

Of course, he had every right to be. It is not every day a freshman in high school -- a shy, reserved freshman at that -- is kidnapped by the most beautiful, popular girls in the school. There were five of us at his abduction.

We had prepared during a slumber party the night before, giggling and staying up all night, talking about kissing, orgasms, blow jobs. Then we took a van and went to the school at around 5am, when we knew the wrestlers would be running before practice.

After clearing it with the coach ahead of time, who was thrilled to be getting some attention from the spirit team for a change, we diverted Lucas off his track and behind several trees by saying we needed help loading some equipment into the van to go to a cheerleading competition.

He was blushing already. I could see him from my lookout point, perched behind the van. He looked simply adorable - his hair wet from sweat after the morning run, wearing nothing more than tight sweat pants and a white t-shirt.

Walking behind the Asian beauty, Trina, he was wiping the sweat from his forehead with his arm. I could hear his voice. He was asking her something.

At that point, he had no idea.

**

Inside the van, it became clear to him that something sinister was about to happen. Three of the others grabbed him by the arms to pin him, and I slammed the doors shut from the inside. Trina started the van from the cab, and we were already leaving.

We were lucky he was a gentleman, because it was obvious he could have easily taken us all down. Just by helping hold down his arms I realized how strong he was. And that turned me on even more.

First, we tied him up. I enjoyed that a lot.

He kept asking, "What are you doing to me?? Is this a joke??"

Peg tried to duct tape his mouth shut, but he kept turning away. When I leaned over to help hold his head still, I felt the erection in his sweats.

It was clear he was enjoying it. Maybe a little too much.

**

Peg had put a dog collar on him that we'd bought from the grocery store the previous night. This made us all giggle, and we found ourselves walking him up the drive way to Trina's house.

Trina's parents were gone for the weekend, so we had free reign of the house. This is where Lucas would experience his "transformation".

All of the tools were on the table in the main room. Trina led him by the leash into the house, careful not to trip him as he was blindfolded.

Soon Lucas found himself tied to a chair, looking around at all of us. Surrounded by a handful of beautiful women, women he had probably dreamed about. Women he had prayed would one day just say "hello" to him in the hall.

It was apparent that he saw himself as somewhat of an introverted geek. And the other girls treated him that way. Cruelly, enough to make me cringe. But somehow it turned me on.

"I think we need to give him a girlie name," Andrea said as she picked through the make up. Lucas was watching, and by the look on his face I think he knew what was about to happen.

Soon Becky was commenting on his erection, and that mortified him. He turned so red that I thought he was going to pass out. But it got worse.

It got worse because Danielle, the more sexual of the team, actually pulled down his sweats and took it out. And they all started giggling. His cock sprung out at once. He was fully hard.

"Look! He's turned on that we are going to dress him up like a girl!" Danielle observed. She got right in his face and said, "You like dressing up like a girl, Lucas?"

"Maybe we should call him 'Lucky' since this is his lucky day!" Trina observed.

"I like the name Lucy."

Lucas looked at everyone, trying to find someone to give him mercy, trying to ignore Danielle's poking and prodding at his throbbing erection. She was making noises, pushing it to watch it bob up and down.

Still, even in this completely humiliating situation, I found him very arousing. When his eyes fell on me, I had to look away. I felt guilty; after all, this was all my idea.

"Let's get pussy-boy dressed," Danielle said, having tired of playing with his erection. She pushed it back into his briefs, under the sweats, and then said "Where are those panties?"

***

We realized, of course, that he might not cooperate during the dressing stage of the ritual. That's why we brought the polaroid.

We took pictures of him after we had done his make up. This was while he was still tied up and couldn't resist, although it took three people to apply it -- two to hold his head, and one to put it on him.

Then we took the pictures, and showed him.

Then Peg, editor of yearbook, dropped the hint that those, and even more incriminating photos, might end up in the annual.

"I'll cooperate," he said.

"Say, 'my name is lucky lucy, and I am ready to be dressed up in a cheerleading skirt for all my friends!' " Danielle ordered.

She was leaning over, purposely, teasing poor Lucas with her tits. She actually pulled her shirt down, when he turned, and revealed her nipple to him. She was known around school for being an exhibitionist.

Lucas turned bright red once more, turned away, and had his eyes shut.

"What's the matter, never seen a tit before?" she asked.

Trina was bringing over the outfit. "Not since his mama."

Perhaps their sheer cruelty would have bothered me more if he seemed upset by it. Sure, he struggled, and blushed, and sighed. But he was hard the entire time, and when he caught my glances, he almost seem to look toward me longingly.

Or maybe that was my imagination.

**

Dressed as a cheerleader, Lucas, or I should say "Lucy", actually looked quite hot.

We had him in the short version of the pleated skirt, with a tight sweater. The bra had been tricky, but we stuffed it with socks and he was sufficiently busty. So busty, in fact, Danielle reached down his sweater to remove some of the padding, stating, "No one on the squad can have bigger tits than me, not even you, Lucy."

Next, we taught Lucy a few cheers. His coordination left a lot to be desired, but he actually seemed to be somewhat amused at that point. I think after being flashed a few tits, having his cock out and exposed to all of us, then dressed up and covered in make up, he was comfortable around us.

When we felt Lucy was sufficiently trained, we decided to make our move. The other's left to prepare the van, and I was left alone with him for the first time. To "keep an eye on him."

I had planned it that way.

**

The first thing I did when we were alone was kiss him.

I kissed him hard, without warning, and he stood there, frozen. He let out a little muffled squeak.

His lips felt soft, and the feel of lipstick-against-lipstick was strange. I could tell at once that he had little, if any, experience with kissing. He definitely was a virgin.

That turned me on.

I was getting wet myself, and I could feel the bulge, under his skirt and in his panties, pressing into my crotch. The kisses became deeper, and finally he reached up and held me carefully by the arms. It was as if he did not want to offend me.

When we broke the kiss, I whispered, "You look good dressed as a girl. I just have to tell you that. Not many men can pull that off."

"Thanks," he said, looking at me strangely. "I think."

His eyelashes fluttered a little. The dark mascara made them stand out even more. This was probably when it all started for me -- the total lust for a man completely dressed up as a woman. Because he looked so hot, I wanted to have sex with him right there.

"I want to go out on a date," I said. I was always straight forward, and I knew there was no way in hell a freshman would have the guts to ask out a senior cheerleader.

He raised his eyebrows, shocked, flattered. "Do I have to dress like this??" he laughed.

I chuckled, looking him up and down. "Maybe. I do like it."

He twirled around for me.

"You like it, too."

"No comment," he said.

And then we were interrupted.

**

The rest of the story is history, as they say. We took "lucy" to the pep rally and made him come out on stage in front of the entire school. He received a standing ovation, especially from the wrestling team. Then we had him perform a cheer with us.

For most guys -- especially the football team -- it never would have worked. They would have been way too afraid to go along with it. Perhaps it helped a little that Lucas was shy and into being guided, and had always fostered a fantasy about being kidnapped by the entire cheerleading squad.

I found that out from him, actually, on our third date. We ended up being together for the entire rest of my senior year, and through the summer until I left for college.

And he used to dress up for me, on demand, and we'd have sex that way. I always called him, "Lucy", and he was as good in bed as he was on the wrestling mat.

  

  

  

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