Brian had been dating Jan for about two years now. A few times each year, she tended to disappear for a weekend to attend one of the local "Renaissance Festivals" in nearby towns, but Brian had never had much interest in going with her. Every time Jan tried to convince Brian, he would claim to be "too busy" or make up an excuse. One day, he found himself unable to think of a reason, and decided to blurt out his real opinion.
"It just seems so childish." He explained, "You should grow up and stop wasting your time, too."
Naturally, this did not go over well with Jan, and he spent the next few weeks trying to make up for it. He tried to apologize, suck up to her, even doing anything she wanted in the bedroom, but still he felt like she was giving him the cold shoulder. Then, she approached him one afternoon.
"You're coming to the festival with me this weekend." She said, plainly, "Or it's over."
"Ok... but I won't enjoy it."
"Oh, I'm not so sure about that." She grinned slyly, "This weekend is special. It's the Faire's 'Adults Only' weekend. We'll see how childish it really is."
"Adults only, you say?"
"Yep. You'll probably see your fair share of tits. But I need you to sign these papers for... registration purposes. You know, confirming you're over 18 and all that. And you're coming in costume; I already have one picked out for you. "
That Friday, Brian got a look at his costume, and it wasn't what he expected.
"That's... that's a girl's outfit." He stuttered.
"More of a wench's outfit really, but you get the point," Jan replied.
Brian didn't know what to say. They had experimented with a bit of cross-dressing in the bed room before, Jan really had a thing for it, but never in public. If anyone who knew him was there, he'd be humiliated for life. After a pause, he butted in.
"But... what about accuracy" He said, trying to get out of his fate, "I doubt people went around in drag back then."
"Tell that to actors. Anyway, accuracy isn't so important on Adults Only weekend. I didn't hear you complain about accuracy when you were imagining women with their tits hanging out."
She was right, of course. Brian hadn't been concerned about accuracy when he thought it would be a chance to see some barely dressed women. But now, it had been his last hope to get out of this.
"If it's any consolation, you won't be the only guy there as a girl. And I'll make you up so it will barely be noticeable."
Saturday morning, they arrived at the faire with Brian decked out in a white chemise with a brown bodice, and a long brown skirt with a white underskirt. His makeup had been done up by Jan, but to an extent where he looked a little trashy, and not as subtle as he had hoped. On his head he wore a dirty blond wig that was long and braided. Despite accuracy, she had insisted he wear a bra and panties under the outfit to complete the illusion. He had to admit, he did look like a woman for the most part, ignoring the obvious giveaways of his Adam's apple and broad shoulders. Perhaps he could get away with this without being too noticed. Jan, meanwhile, was dressed as some sort of noble woman. Her red hair braided behind her, she looked quite elegant.
Looking around the faire, with its many shops, Brian finally began to understand why Jan liked these things so much. There were costumes and games and interesting foods all around. At the center of the fairgrounds, Brian saw two pillories sitting side by side. Seconds later, his hope of anonymity was dashed.
"There she is! The wench Brianna!" Someone yelled, as several men in costume approached, "For lewd behavior, you are hereby sentenced to an afternoon in the pillory!"
"Wait... what... you've got the wrong guy."
"We've most certainly got the right girl!" One of them said loudly, then quietly, "You did sign the agreement, after all."
Brian, or Brianna, understood now. His face turned pale under all its layers of makeup. The paperwork Jan had him do, was all for this. The men lead him to the pillory, and proceeded to lock his head and hands in place. A crowd was gathering around. Brianna had quickly become the center of attention for the guests at the faire. Then, he saw two of the men who had seized him carry buckets to the waiting crowd.
A tomato hit Brianna right in the face, splattering as it made contact. Then, another shot forward and hit him with such force as to knock his wig partially off.