Harley Quinn’s Wedding Crash: A Best Man’s Makeover

An Unexpected Invitation

Timmy’s hand shook as he looked over the wedding invitation. It was for his best friend Erika’s wedding. They had been best friends since college and had even dated once upon a time. Despite breaking up, they were still best friends.

But the invitation still came as a shock. Ricky, Erika’s boyfriend or fiancé now, didn’t like that they still hung out. Probably felt challenged by their past relationship. As a result, Timmy could feel Erika hanging out with him less and less. With an invite to the wedding, he felt excitement that she was overcoming it.

Erika’s Unique Plan

Within minutes, he was dialing up Erika’s phone number. He was eager to talk with her once more. Erika answered quickly. Without missing a beat, Timmy spoke up, “Just got the wedding invite!”

“Oh! Yay!” Erika stated, “I am so excited for it! I am glad you liked my little idea.”

That caused Timmy to pause. “Idea? It is just a wedding invite.” However, he was curious if there was more to it. Maybe he should open it. Grabbing his letter opener, he ripped it apart.

“Yeah, just with how things are between you and Ricky? He refused to let you come along, but I really wanted you at my wedding,” Erika continued. “So, I remember that one Halloween when we were together. We wanted to have matching costumes, so I went as the Joker, and you went as Harley.”

“You want me to attend as a girl?” Timmy had finally gotten the letter open and read Erika’s ‘idea’. He remembered Halloween, wearing heels and a short skirt, and strutting around. He had been a college kid and practically lived off alcohol and dumb ideas. If it wasn’t for that, there was no way he would’ve agreed.

Thanks to his little outburst, Erika’s voice fell. “Come on, Timmy. I want my best friend at my wedding.”

Biting his lip, Timmy could feel himself giving in to Erika little by little. He was always a bit of a pushover when it came to her, but still. “I’m a guy. I’ve grown a lot since college.”

“We exchanged Christmas photos last year, remember? You could still pull it off with a little help from me and your fellow bridesmaids. You’ll come down, we’ll do the entire transformation at the Bachelorette party, and you’ll have fun. If you’re still not convinced, my maid of honor, my best friend, my one true companion,” Erika began to lay it on thick.

“Fine, fine, fine!” Timmy said with a laugh at Erika’s antics. “I’ll do it.”

The Wildest Bachelorette Party Ever

The night of the bachelorette party was starting. The butterflies in Timmy’s stomach hadn’t stopped ever since he got the wedding invite. Erika had been doing her best to calm his nerves. Despite it being her big day, it seemed like she was doing all she could to ease his nerves.

The party would start here with a few drinks and greetings. After that, the attention would shift to Erika’s crazy plan. Changing him away from mild-mannered office worker Timmy Olson. He would be transformed into the best friend of the bride, Harley Queen.

“So, Timmy, you’re tonight’s main entertainment,” whispered one of the bridesmaids as she walked up to Timmy. She had gone through two or three of the margaritas already. She was Rita, Erika’s roommate from her college days.

With his cheeks turning a bright crimson, Timmy tried to right himself. “I’m not sure if entertainment is the right word.”

“Nonsense, dolling you up is going to be so much fun!” cheered Rita, and a few of the drunker bridesmaids joined in. “So when are we going to see what we’re working with?”

“Not sure what you mean. What you see is what you get.”

A Dare Becomes Reality

“Strip.”

Timmy thought the first time it was a joke.

“Strip.” The second one seemed to be serious.

“Strip.” The third one was more of a command.

“Strip.” By the time the fourth one rolled around, it was a cheer that the entire room was yelling. The chant of ‘Strip, strip, strip’ was an almost hypnotic hum.

The attention and the drinks made Timmy cave in to the cheers and peer pressure. He started to unbutton his shirt.

“No, girlfriend, do it sexily,” one of the bridesmaids cheered as she wiggled her own body.

Once more, Timmy relented. Swinging his hips in time with some imaginary music. He threw his hair side-to-side and getting cheers from the girls. One of his hands slipped down his side, winding up on his hip.

“He needs more assets to shake,” one of the girls laughed. Soon, two large flesh colored squishy mounds of silicone were glued to Timmy’s chest. This gave him a pair of fake breasts. The girls had definitely gotten a bit too excited, and Timmy couldn’t find his voice to say no.

These only exaggerated his motions. Now every swing also came with a jerk as the extra weight pulled and bounced. The crowd grew more and more rambunctious. “Blow us a kiss!” “Flutter your eyelashes!” “Where are your high heels?” Among several other excited cheers.

Every single one of these cheers melded with the crowd and soon added another item to Timmy’s wardrobe. The heels were skyscrapers at least 5 inches high and made every step Timmy took tiny and bouncy as he adjusted.

Huge fake eyelashes covered half of his vision. His lips felt puckered into a kiss, and they left a smear of red on anything he drank from. He also knew his cheeks had a dusting of pure red blush.

Catching Erika’s Eye

He was now dancing in high heels and a pair of large fake breasts. Had he been asked a week ago, he would’ve thought it humiliating, and maybe it was a little bit. But it was also fun! Besides, it also wasn’t like he was going to see many of these girls after this. He didn’t even know their names. He would see Erika, but that was about it. And she wasn’t even here yet.

Just then, his eyes crossed the room, still hooded with long false eyelashes, and he saw her. Erika sat all by herself.

Sitting in the back of the hotel room and just enjoying the show. She had a water in one hand and one of those crude novelty pieces of candy, the one shaped like a cock in the other. She twirled it around in her hand, noting that Timmy had noticed her.

She pinned the candy between her forefinger and thumb and then used the other three fingers in a wave. Slowly curling them and uncurling them one by one. She patted the seat beside her as an invitation.

All at once, Timmy became painfully aware of how hard it was to walk in high heels. How much his breasts jiggled, how much make-up coated his face. The entire walk over there, the bridesmaids cheered him on with catcalls and cheers.

As he sat down next to her, he had another realization. Not only was he now in a neon pink thong, but several dollar bills were now lining the string. They tickled his exposed thighs. “H-hey Erika.”

“Hey, Harley,” Erika sang as she looked her best friend up and down. “Here I was thinking it would take a lot more to coax you into this role.”

“I was just having fun.”

Erika crooked a single finger and lowered it down to Timmy’s waist. It caught on the thong, and he pulled it slightly before letting it snap back onto him. “Certainly looks that way. I think you’re going to have a lot of fun tonight.”

Timmy opened his mouth to protest, but Erika was a bit too fast. She shoved a novelty cock shaped candy between his lips. This silenced him as his mouth filled with the taste of the sweet.

“Relax, Timmy,” Erika perked up, “I am glad to see you like this. If I had known you would get into it like this, I would’ve suggested it sooner. After my wedding, I’ll have to have more girl nights out with my best friend Harley.”

Harley could only nod with the candy cock sticking halfway out of her mouth. Then Erika gave her butt a quick swat, and she was back on her heels. She was back to being that night’s entertainment with a strong feeling that other nights would follow.

Harley at the Wedding

The next day, Harley was standing in front of the crowd. She was dressed more modestly now. Now wearing a long ball gown that covered her assets while still highlighting them. Her corset pressed her two soft, jiggling breast forms together and up to accent her cleavage.

She tried to organize her thoughts from last night, but the burning hangover made it hard. She could only remember half of it, but it had all been great. Everything was going well. She thought back to last night, and even now, it was all worth it.

The introduction to Ricky was awkward. It seemed like he hadn’t put together that Harley and Timmy were the same person. If anything, Harley was certain he had checked out her breasts once or twice.

But now Erika was here, and all eyes were on her. The beautiful, blushing bride made her way down the aisle. The room was quiet throughout the whole ceremony, the priests spoke, and the happy couple both said ‘I do’.

The transformed Timmy smiled on throughout it all. He wondered if someday he, too, would be such a beautiful bride.