Chapter 75
by
Mr Nice Guy
What's next?
He Wore an Itsy Bitsy Teeny Weeny...
His belly full, Jon excused himself from the table, happy to be returning to his room to get dressed for the day. Sure, he had felt completely comfortable dressed as he was in nothing but his white see-through bra, panties, and of course the apron he'd found in the kitchen (after all, what guy doesn't feel good eating breakfast in his underwear while on vacation?), but when he had seen what Kelli had worn that morning, all the comfort he'd felt vanished.
Maybe Jon had invited it, having dressed so casually, but from Jon's perspective it was too far over the line. It was bad enough that Jon had been **** to dream about Kelli all night, but when Jon turned around from the pancakes he had been making, his roommate has walked into the room wearing nothing but a pair of women's panties and a black, see-through babydoll! Lingerie! WOMEN'S LINGERIE!
Jon had tried to keep it light, keep it friendly. After all, whatever Kelli wanted to do on his vacation was up to him. Jon just didn't want to be associated with it!
"Got plans for the day?" Jon had asked, serving a plate of pancakes to his new companion.
"No plans," Kelli said, enthusiastically, "You?"
"Oh, you know," Jon said dismissively, "vacation stuff..."
It wasn't that Jon didn't like Kelli, but Jon was on a mission. He was here to bone women, and having a crossdresser like Kelli hanging around would just cramp his style!
Breakfast consumed, dishes put away, Jon retreated to his room to prepare for his day. The first thing for him to do was get dressed.
The closet wasn't huge, but Jon had never been a clothes horse. While it held none of his clothes from home (why hadn't he packed a bag for this trip, anyway?) it held everything he could need during his vacation. Dresses, skirts, blouses, exactly what any red-blooded man would want for a tropical holiday. Nothing too hot or bulky, everything exactly in his size. His dresser, too, held more than enough. Panties, bras, jean shorts, bikinis, and more. Jon felt relieved that he wouldn't have to worry about finding outfits while he had the apartment, that he could always return here if something happened to his clothes, as often happened in Girl World. With the selection available, he'd have no trouble convincing women that they'd found a suitable, and manly, mate when they saw him.
With a hint of disgust, he wondered what Kelli's room must look like. While Jon's tastes were obviously reflected in his masculine assortment of skirts and blouses, Kelli's must be reflected in his own room as well. Jon pictured Kelli flitting around his room, looking at skirts, dresses, blouses, clothes that a woman should wear, not a man. Why anyone would waste their vacation by coming to Girl World and spending the whole time crossdressed was beyond his comprehension.
The sun was up and the weather was hot, so Jon decided to start the day at the beach. He was, after all, on vacation, and what better place to relax (and meet women) but catching some rays on the sand! Sliding open a drawer, he pulled out a skimpy blue bikini, one that would prominently display his penis out front, only covering enough skin on his chest to give show of his broad, tough chest for any woman he met.
The problem was, he found as he stared at his body in the full-length mirror on the closet door, that his chest was looking a little weak that morning. Maybe it was the colour of his bikini, maybe it was that he hadn't had enough pancakes, but he was looking positively concave.
Returning to the dresser, he slid open another drawer and found something to solve his problem. Reaching in, he pulled out a large pair of breast forms, exactly in his skin tone, that he glued and then slipped beneath the cups of his bikini top. He turned and faced the mirror again from across the room, thrusting out his now huge, extremely manly chest. It was perfect. D-cup, the imprint on the back of the forms had said. D for Dashing he giggled to himself, enjoying the way the breast forms jiggled as he did.
Something about his reflection wasn't quite right, though. Jon turned and faced the smaller mirror atop his dresser for a closer look. It was just as he thought. The seams on his breast forms were showing too obviously. The last thing he wanted was for a beautiful woman to see him, see his chest, and think he's a faker. It was bad enough that he was being seen so much with his crossdressing roommate, but if a woman thought he wasn't manly enough to have breasts as big has he was displaying, if she realized he was only wearing forms, he would die of embarrassment.
Grabbing some foundation make-up that was on top of the dresser, he began to blend it in over the seams of the forms. All the way around, gently, smoothly, as if he'd been doing it his entire life, and soon the seams had vanished.
Jon smiled in satisfaction, only to have something feel wrong again. It was his lips. His lips were puffy, extremely puffy. It must be a reaction to all the sunshine during yoga, he thought to himself, I'd better treat them before they get chapped.
He reached over and grabbed the tube of lip balm, fire-engine red, and applied it to his puffy lips. Once they were covered, he blew himself a kiss in the mirror, enjoying the feel of his now medicated lips, and turned away from the dresser.

The last thing he needed was shoes. Since it was a beach day, he grabbed a pair of size seven flip flops, a perfect fit. For a brief moment a faint memory, as if something out of a dream, flashed into his head of bigger feet, bigger shoes, as if his feet had somehow shrunk. He giggled at the thought. Feet shrinking? That wasn't possible!
Confident that he was ready for a great day, Jon grabbed a blue and beige striped canvas beach bag which he filled with a towel, some sun-tan oil, a wide-brimmed hat, and a pair of big rose coloured sunglasses with pink rims. He had everything he needed for a fun beach day, the perfect day to pick up a lady. Now if he could only sneak out of the house without Kelli tagging along.
What's next?
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Girl World
Jon's vacation isn't what it seems
Jon finds himself on a vacation in Girl World, a place filled with beautiful women that promises to fulfil his every sexual dream. Only that's not exactly what's happening... but does he notice?
Updated on Jul 27, 2025
by Mr Nice Guy
Created on Mar 25, 2023
by Mr Nice Guy
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