• Published 13th May 2021
  • 1,116 Views, 29 Comments

Birthday Gyrrl - shallow15



Flash Sentry has come home from college for his birthday. Sunset Shimmer and Rarity have the perfect gift planned for him.

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The Present

Flash Sentry contemplated the panties sitting in the box. They weren't anything exotic. A simple black cotton pair of briefs from an 8-pack purchased from Value Mart, one of thousands of mass produced pairs that the retail giant sold every day. There was nothing overly sexy or fetishistic about them.

And yet, they filled Flash with contradictory senses of excitement and dread.

It was his 19th birthday and he had gone home for the weekend from college. A celebratory dinner with his mom had happened the night he got home, which left the rest of his weekend free to meet up with friends. Unfortunately, most of his friends were also away attending school, which was why the call from Sunset Shimmer was both surprising and welcome.

“Hello?”

“Hey there, birthday boy!” Sunset's voice was lively and vibrant. “How's it going?”

“Not bad. Mom got me a GameStation 5.”

“How the hell did she find one?” The envy was audible in Sunset's voice. “I've been trying to score one for months!”

“You know mom,” Flash replied. “Probably just had to ask a clerk to hold on to one.”

Sunset let out a snort of laughter. Flash's mother, Azure Flame, was ridiculously attractive and radiated sexual charisma for miles around her. Fortunately, Azure was also blissfully oblivious to the effect she had on men and women both and she wrote off the various favors she was able to acquire as just running into several very nice people.

“Anyway,” said Sunset. “What are you doing tonight?”

“No real plans,” Flash answered. “Why?”

“Wanna get together for another birthday celebration? Rarity and I have a surprise for you.”

“Really?” Flash blinked.

“Yep! And you know Rarity. If you say no she'll be devastated and I'll be spending the whole night trying to keep her from drowning in ice cream and mascara.”

“Well, we don't want that. What time and where?”

“Say, six o'clock? I'll swing by and pick you up and we'll head over to Rarity's place.”

“Since when do you have a car?” Flash asked.

Sunset laughed. “See you at six.”

True to her word, Sunset arrived at Flash's house, driving a small elderly car. It wasn't much to look at , but Flash noticed it was clean as he climbed in.

“Nice car,” he said. Sunset smirked.

“It's paid for,” she said. “Come on, mustn't keep her waiting.”

The ride to Rarity's house didn't take long. Sunset parked in the driveway and the two of them walked to the front door. Rarity answered the door almost as soon as they rang the bell.

“Sunset! Flash! Darlings!” Rarity wrapped them both in a tight hug. “So good to see you!”

“Good to see you too, Rares,” said Sunset as the fashionista released them. Rarity stepped over to Flash and smiled.

“Happy birthday, Flash, darling,” she said, air kissing his cheek. “I'm so glad you decided to come over.”

“Thanks for the invitation,” said Flash.

“Well, come in, come in!” Rarity stood aside, allowing them access to the house. She led them up the stairs to her bedroom. Flash had never been there before, but it was everything he expected. A four poster canopy bed. A desk with a sewing machine set up on it. A dressmaker's dummy in one corner and assorted scraps of cloth, ribbons, and spools of thread scattered haphazardly across every surface.

A large gold gift box bound with a blue ribbon was sitting on the bed. Rarity picked it up and presented it to Flash with a dramatic flourish.

“I know I'm being a terrible hostess, but I simply cannot wait any longer to give this to you. Happy birthday, Flash, darling!”

Flash looked a the box in his hands, then back up at her. “Rarity, you didn't need to.”

“Of course I didn't!” Rarity grinned. “That's why it's a gift. And you can thank Sunset as well.”

“It's kinda from both of us,” Sunset confirmed. “I told her what I thought you'd like, gave her your measurements, and she went to work making it.”

“'Making it?'” Flash stared at Rarity. “You made something for me?”

“Well, the largest component of your gift. There's a few little... er... odds and ends I purchased off the rack.” Rarity flushed slightly as she explained, but Flash was looking back down at the box again and didn't notice.

Sunset nudged him in the side with an elbow, bringing him out of his stupor. “Open it! I wanna see your face when you see it!”

Flash grinned at her and went over to Rarity's bed. He put the box down, then undid the ribbon and lifted the top...

… and stared. He reached inside and pulled a bundle of cloth out. It unfolded and billowed down, flowing from his hands and swinging freely in the air.

It was a dress. A dress in lime green and black with cap sleeves and a flowing skirt that was guaranteed to billow out with the slightest twirl. It was soft and silky, but with just enough weight that signified its durability. The bright green was spread out across the upper half of the dress, deliniated in sharp lines by the black which over took the majority of the skirt.

It was one of the most beautiful things he'd ever seen. He looked over to Sunset and Rarity.

“How...?” he began, but he choked up.

Sunset smiled at him. “You remember when we got drunk the night after graduation?”

Flash nodded. Sunset had procured a bottle of rum from somewhere and the two of them had gotten merrily blasted in her apartment. During that time, the two of them had confessed some of their deeper secrets.

It appeared Sunset had remembered one of his, and she now looked like she was unsure if it had been a good idea.

“Well,” she continued. “I thought, maybe, you'd like this. So I asked Rarity to make something for you.”

Flash looked back at the dress, imagining himself in it. How it would feel hugging his figure, the skirt swishing around his legs as he walked. Feeling the skirt shift and flutter as he twirled in place. It was everything he ever wanted in a dress.

“Is it all right, darling?” Rarity asked. Both she and Sunset looked at him anxiously. He looked at them, then back at the dress, then put it back in the box.

“It's beautiful... but I can't.”

“What?” Sunset asked, surprised.

“Why on earth not, darling?” Rarity said.

“Look, it's really sweet of both of you, but I can't wear it. It's... it's too nice to waste on me.”

“Flash, I can assure you it is most certainly not a waste!” Rarity leaned forward and took his hand. “This was made for you, darling, and I can tell you that you are not the first man I've made something like this for.”

“Yeah,” Sunset added. “There's nothing wrong with wanting to wear a dress, Flash.”

“It's not about wrong,” Flash protested. “It's just... I don't think I'd look good in it.”

“Pfft-tsk-tch!” Rarity stood up and grabbed Flash's wrists, pulling him to his feet. “Darling, if there's anything I've learned, is that the right dress with the right accessories and makeup can make ANYONE look their most fabulous!”

“But – “

Rarity held up a hand. “Ah ah ah! No 'buts,' Mr. Sentry. Or do you doubt my skills?”

Flash flushed. “No! No, it's an amazing dress, Rarity. I'm just...”

“Just what?”

“Afraid... I'll... make it look horrible. Like the whole thing will look ridiculous and you'll have gone through all that trouble for nothing.”

“Why don't you let us be the judges of that?' said Sunset, standing up to join them.

“What do you mean?” asked Flash.

“I mean, give us tonight. We'll help you with makeup, your hair, the dress, all of it. We'll see what the end result is, and if you still think you don't look good, we'll pack it all in and not talk about this again.”

“Oh, wonderful!” Rarity squealed. “And Sunset and I will dress up with you. A good old fashioned makeover night!”

“Yeah!” Sunset agreed. “Just the three of us. No judgment, no pictures, just fun. Sound good?”

Flash looked at their eager expectant faces, then down at the dress. They had gone to all the trouble of doing this for him and it seemed unfair to just write it all off because of his own stupid insecurities.

“Okay,” he said. “Let's do it.”

Rarity clapped her hands together and picked up the box and put it in Flash's hands. “Wonderful, darling! Let's go upstairs. There's one or two more things in there besides the dress.”

One or two more things. Like the panties Flash found himself starting at. He was in the bathroom and had been for some time, standing there in his boxers, waffling. The box had also contained a pair of thigh high black stockings, a black bra, and the panties. He continued to look at them, his mind wondering if this was really how far he could go.

The stockings weren't a problem. They'd easily cover up the fact that his legs weren't shaved. And the bra, well, given he didn't really have anything to fill it out, it was more or less optional.

But the panties...

It felt like it would be crossing a line. A line he wasn't sure he was ready to cross yet. Rarity had assured him she had acquired the right size, so the risk of them being too tight or too loose wasn't the problem. His mind kept insisting that it wasn't right, that he was somehow breaking a sacred taboo by even considering putting them on.

A knock at the door interrupted his hamster wheel of thought.

“Flash,” came Sunset's voice. “You okay in there?”

“Yeah, sorry,” he called back. “I just... um...”

He trailed off, not sure what to claim the hold up was.

“Listen, you don't have to wear anything in there you don't want to,” said Sunset. “We put all that stuff in there so you could go as far as you're comfortable. It's just for fun, Flash, so don't feel obligated to humor us, okay?”

“Okay,” Flash replied. He reached down and picked up the panties, rubbing the material between his fingers. It didn't feel all that different from his own underwear, maybe a tad softer, and they didn't have the seams in the front that opened up that inexplicable hole that men's underwear had, since the only conceivable purpose for it was too awkward and cumbersome to work with, when you could save time and effort by just pulling down on the front waistband.

So really, if it was the same material, and it was the right size, and they weren't much different from some of the pairs of black men's briefs he had at home, what was the big deal, right?

Flash took a deep breath, dropped his boxers and quickly replaced them with the panties.

Oh... wow.

They were soft. Much softer and less coarse than the cotton used in his boxers. The fit was a little more awkward, since, of course, he had things where things wouldn't normally be if a woman were wearing them. But overall, he found them comfortable. Very comfortable.

He let out a sigh of relief, pleased that he'd managed to get over the hurdle. He sat down on the closed toilet and pulled on the stockings. The tops squeezed his thighs slightly, but a little adjustment eased the pressure. He decided to forgo the bra, since it would require stuffing it, and he was worried he'd come off looking too artificial in that department.

That just left the dress.

He pulled down the zipper at the back and held it to his front, looking at himself in the large bathroom mirror. He frowned.

Still looks like a dude in a dress to me. Maybe it'll look better if I put it on.

He pulled the dress on over his head, and after a minute or two of fumbling around, managed to get his head and arms through the correct holes. He pulled the dress down the rest of his frame and looked at himself again in the mirror.

The dress fit him perfectly, of course. Rarity had clearly made sure of that. The skirt actually started flowing from the body of the dress just above his navel and came to rest midway between his hips and his knees, covering the tops of the stockings. He rocked his hops back and forth a bit, watching how the fabric moved and glided with him. The neckline was high, similar to the collar of a t-shirt, making the need for exposed cleavage a non-issue.

He became aware of the general airiness that came with wearing a skirt. His legs felt free and unencumbered, and the movement of the skirt sent pleasant little puffs of air across his thighs. The skirt was large enough and hung in such a way that the obvious bulge in his panties was invisible. The material felt wonderful against his skin and the colors complemented his skin tone and eyes. He reached behind his back to do up the zipper...

… and immediately realized he couldn't reach it to do up the dress. It was too far down, nearly at the small of his back. He contorted his arms in several different and uncomfortable positions but couldn't even get close to the zipper. He sighed in exasperation and looked back up into the mirror.

I still look like a dude in a dress.

Another knock at the door.

“You okay in there?” Sunset asked again. Flash stifled another sigh and opened the door. Then he blinked.

Sunset had changed into a slinky black cocktail dress that hugged her curves in all the right places. It wrapped around just below her bare shoulders, leaving a tantalizing amount of cleavage. Her geode was still around her neck, resting just above said cleavage.

“Wow,” Flash whispered.

“You look pretty 'wow' yourself,” Sunset said, a similar look of astonishment on her face.

That brought Flash out of his stupor. “If you say so,” he said, looking down.

“I do say so,” Sunset said, tilting his chin back up and giving him a smile. “Looks a little loose though.”

“I pulled the zipper down too far,” Flash admitted, blushing. “I couldn't get it back up again.”

“Oh yeah, that's a bitch when you're dressing on your own. Easiest thing to do is unzip it halfway, then you've got enough room to get your head through, but still able to reach back and zip it up again. But for now...”

Flash let out a yelp as Sunset spun him around, zipped up the dress, then spun him back again.

“Done!” she chirped. “How does it feel?”

“Um... airy?” he said, picking at a fold in the skirt. “Kinda weird but... comfortable too, I guess.”

“It looks good on you.”

“It does?” Flash gave her an incredulous look. “Come on.”

“No, seriously, it does,” Sunset insisted.

“I look like me in a dress.”

“And I like you in a dress. But what I like isn't important. We're here to make you like yourself in a dress, and the next step in that is makeup.”

She took Flash's hand and began leading him back down the hall to Rarity's room.

“I don't know anything about makeup,” Flash protested. “I'll wind up looking like a clown.”

“Nonsense!” Rarity appeared in the doorway of her room, having heard him as they approached. She, too, had changed clothes. Now in a blue sequined, off the shoulder gown with a floor-length skirt slit up to mid thigh on one side. Gold bracelets were around her wrist, and like Sunset, her geode was around her neck.

“By the time I'm through with you, Flash, darling, you'll be the prettiest thing you've ever seen. And I'll be explaining everything I'm doing so you can do it yourself at home! Er... assuming you decide you'd like to do this again,” she quickly added, seeing the look of panic on his face. “But! As I say, tonight, I can guarantee you will be fabulous!”

She stepped forward and took Flash's hand. “That is... if you trust me. I hope you trust me when I say that I am not out to make you look foolish. I want to help you become the most beautiful you can be. Will you trust me to help you do that?”

Flash looked at Rarity's earnest expression, then over at Sunset, who gave him an encouraging look and a thumbs up. He looked down at himself, seeing the dress. It certainly did fit him well and the girls had been nothing but supportive so far. He looked back up at Rarity.

“Okay.”

Rarity let out a shriek of delight and yanked him back into the bedroom, causing him to let out a yelp of surprise. Sunset chortled and followed them in.