Graduation Present

“Syd, what the fuck am I gonna do?” Ezra groaned. “School’s almost out, and that meathead’s gonna kill me as soon as I step outside.”

“Well, I’m not gonna say I told you so,” Sydney shrugged. “Tiff, you tell him.”

“She warned you, dude.” Tiffany looked up from her phone. “She said if you put that photo in the yearbook, he’d kick your ass.”

“I know, but how could I not? It was the perfect shot! The expression on Jack’s face as that goat rammed him in the nuts? Come on.”

“Yeah, it was funny,” Kiki agreed, “and it’s what he gets for stealing another school’s mascot. But Syd totally warned you. We all did.”

“Fuck! This is it. This is how I die. Seconds after the last day of high school, all because you talked me into joining the yearbook club.”

“Quit your moaning,” Sydney teased, poking him in the shoulder. “You’re being overdramatic. All you have to do is avoid him as we leave school. It’s not like you guys hang out in the same places. He’ll forget all about it. And even if he doesn’t, you’ll be heading to college while he goes to, I dunno, learn how to drive a bulldozer or something.”

“How am I gonna avoid him? He said he’d be waiting for me!”

The other students shuffled restlessly, picking up their bags and staring at the clock.

“Well,” Sydney considered, “I’ve got an idea, but you’re not gonna like it.”

“Syd, I’ll do anything! Please, save me!”

The bell rang, and everyone streamed for the exit, ignoring the teacher’s requests to slow down.

“Alright, follow us.”

Ezra let Sydney and the girls lead him into the hall, against the flow of students laughing, cheering, and heading for the front doors. As they waded through the crush, the crowd eventually thinned until they led him to a girl’s bathroom.

“What are we doing here?”

“You’ll see,” she grinned, pulling him through the door.

Inside, two junior girls at the sink squealed at his presence, and left quickly, laughing and winking. Ezra grinned sheepishly and waved.

“Okay,” Sydney said, pushing him toward the far wall. “Take off your clothes.”

“Wait, what?”

“You heard me.”

“Is this a prank? You’re gonna make me strip, and then take off with my clothes? Real funny, Syd.”

“Do you wanna get your ass kicked?”

“No.”

“Do you trust me?”

“I guess?”

“Then strip. And face the wall.”

“Why?”

“So you don’t catch an eyeful.” She gestured. “Go on. Turn around.”

“Alright, fine,” he grumbled, turning away and starting to undress.

“Kiki, you’ve got your gym clothes, right? Okay, change into your shorts and give me your leggings and skirt. Tiffany, let me have your bra. And I’ll donate my shirt. I can wear Ezra’s button-up.”

The girls started laughing when they figured out what she was suggesting. By the time Ezra had stripped down to just his boxers, they had assembled an outfit for him.

“Underwear too, Ez.”

“Seriously?”

“You can’t wear boxers under leggings, they’ll bunch up weird.”

“That’s your plan? Dress me up like a girl?”

“Sure. Lucky for you, you’ve got a slim build, so most of this stuff should fit you okay.”

“This is humiliating,” he groused, shucking his boxers and trying awkwardly to pull on Kiki’s leggings while not letting them see his junk.

“Ha!” She laughed as she put on his shirt, tucking it in and rolling the sleeves. “Be glad I’m not making you wear a thong to get the full experience.”

“How do I put this on?” He frowned, holding up the bra. Kiki and Tiffany burst out laughing.

“Oh come on,” Sydney teased, “you must have taken a girl’s bra off before, right?”

“Well, yeah, but that’s not the same thing.”

“Sure it is,” she laughed, helping him pull the straps up his arms. “In reverse. Hold on, I need to loosen these up. You’ve got broader shoulders than Tiff, but I think it’ll still fit…”

“Oof, it’s tight!” He complained, moving his arms awkwardly. “This is really uncomfortable.”

“Tell me about it!” Sydney giggled, snapping his bra strap. “Here, let me stuff some toilet paper in the cups to pad them out a bit.”

“I can’t believe I’m doing this,” he grumbled, pulling her shirt on over his head.

“Hey, careful, you’ll rip it! I like that top. You can’t just tug it on like a cheap t-shirt!”

“Alright, how do I look?” He asked grumpily, putting his sneakers back on.

“Well, you forgot the skirt,” she snorted, pointing to the obvious bulge in the crotch of his leggings.

“Of course,” he sighed, stepping into it. She helped him with the zipper, then the girls moved back to look at him critically.

“I dunno,” Kiki sniffed. “The shoes are all wrong.”

“And the shirt’s too tight,” Tiffany noted.

“No, it’s his face,” Sydney observed. “We have to do something with his hair, and he needs some makeup.”

“Makeup?” He looked nervous.

“Oh please, you’ll wear a bra and a skirt, but you draw the line at makeup?” Sydney laughed. “Just be thankful your hair is long enough to pass. If it were cut short, we’d have to borrow a big hat from the theater department.”

Kiki set about brushing his hair, while Tiffany and Sydney gave him a quick makeover. After a bit of foundation and eyeliner, they all stepped back again to examine their work.

“I mean, it’s not terrible,” Kiki shrugged.

“I like how you did his hair,” Tiffany agreed.

“Honestly, you’re kinda cute,” Sydney grinned, gesturing at the mirror.

“Huh.” He tried to frown, but even he had to admit the transformation was more convincing than he expected. “This might actually work.”

“Of course it’ll work,” Sydney said confidently, bumping fists with Kiki. “And if not, we’ll get to watch you get your ass kicked in a skirt, so, you know, win-win.”

They left the bathroom and headed for the front doors. Most of the students had already left the building, so there wasn’t much crowd cover as they stepped outside. Sydney motioned for Ezra to walk behind her, with Kiki and Tiffany at her sides.

Jack was standing by the flagpole, arms crossed and glowering. He was flanked by three friends, each bigger than the last. When he saw them leave the building, he called out.

“Hey Sydney, where’s your loser friend? The longer he makes me wait, the harder I’m gonna beat his ass.”

“Fuck off, Jack,” she called out cheerily. He glared as they giggled and kept walking, but turned his attention back to the front door, muttering something to his friends. A few minutes later, Ezra laughed with relief as they boarded a bus, sitting as a group in the back.

“I can’t believe it worked! He didn’t recognize me at all!”

“I told you,” Sydney beamed. “Now cross your legs, you’re sitting like a dude.”

She stifled a laugh as Ezra exaggeratedly crossed his legs, placed his hands on his knees, batted his eyelashes, and smiled at them all demurely. Kiki and Tiffany lost it. Sydney stuck out her tongue at him.

“Hey,” he asked, looking around for the first time, “where are we going?”

“To the mall. We can find a dressing room for you to change in, and then you can buy us all fries to thank us for saving your life.”

“Cool.” He nodded, then scrunched up his face. He rolled his shoulders a few times, trying to adjust his bra band. “How do you wear one of these all the time? This is so uncomfortable!”

“Welcome to being a woman,” Kiki observed dryly.

“Right? My mom freaks if I go out without a bra,” Tiffany said, “but sometimes I take it off as soon as I get to school.”

“Well, as much as I appreciate the loan,” he grimaced, “I’ll be happy to give this back.”

“You know, if the fit’s the problem,” Sydney grinned, “we could get you something in your size? Maybe you’d prefer a different color? Something lacy?”

“Ha. Ha.” He turned to look out the window.

Tiffany and Kiki distracted themselves by looking at something on their phones. Sydney found herself watching Ezra. Every few seconds, he would shift awkwardly in his seat. He uncrossed his legs, stretched, slouched, then sat up and crossed them again.

“Everything okay there, Ez? You look like my dog when it needs to go outside.”

“Huh?” He looked startled, then flushed as if caught doing something inappropriate. “No, I’m just a little, um, uncomfortable.” He adjusted his skirt nervously.

“Oh?” She leaned closer, sensing something interesting. “Uncomfortable how, exactly?”

“Just, you know, wearing women’s clothing,” he mumbled, still fidgeting with his skirt.

“Come on, it’s something more than that. I can tell.”

“No, it’s just that these clothes are a little, um, snug.” He looked deeply uncomfortable. “In places.”

“In what places?”

“Just, places, that’s all.” He nervously shot a glance at Tiffany and Kiki, who were still absorbed in whatever they were looking at.

“Tell me!”

“Fine, fine, just keep your voice down.” He leaned closer and whispered conspiratorially. “The, um, leggings are a bit tight.”

“Tight?” She grinned, deliberately misunderstanding him. “What, like, they’re cutting off your circulation?”

“No, that’s not, um…” He grimaced, putting his hands over his lap. “They’re a bit tight in the, you know, crotch region.”

“Oh my god! Are you hard right now?” She eagerly tried to lift his skirt to peek.

“Stop that!” He hissed, swatting her hand away. “Why are you being weird?”

“Are you into this?” she whispered with delight. “Is wearing our clothes turning you on?”

“No! No, that’s not it. I told you, they’re just kinda tight, so there’s a bit of, like, pressure. It’s a normal reaction!”

“Sure, it’s a normal reaction. If you’re excited by wearing women’s clothing!” She tried again to reach under his skirt.

“I’m not! Shut up!” He looked nervously at the other girls again. “Stop it!”

Before she could get past his blocking, the bus stopped at the mall. Ezra got quickly to his feet, and exited the bus, closely followed by Sydney and the girls.

As they walked through the mall, she stared openly, hoping to catch a peek of the erection tenting his skirt, but he kept his bag in front of him, blocking her view.

When they got to the clothing store, Kiki and Tiffany wandered off to do a bit of a shopping, while Sydney led Ezra to the dressing rooms.

“What are you doing?” he whispered when she followed him in, shutting the door behind her.

“Okay, now you can show me,” she grinned.

“I’m not showing you!” He continued holding his bag protectively in front of himself.

“Why not? Tiff and Kiki aren’t here.”

“That’s not why! This is weird. Why are you being like this? You’ve never shown any interest in me before.”

“You’ve never dressed like a girl and popped a hard-on in front of me before.” She bit her lip. “And, I wasn’t lying, you look cute like this. I think I’m kinda into it.”

“Does that make you a lesbian?”

“Does dressing this way make you a girl?”

“No!”

“Then, I guess not,” she grinned. “Come on, put your bag down.”

“Ugh. Fine.” Despite his protests, he allowed her to take his bag and set it on the bench. He crossed his arms awkwardly. “Now what?”

“Show me what you’re hiding under that skirt.”

Sighing dramatically, he slowly raised the front of his skirt for her. His erection was pressed against his stomach, held in place by the leggings. She could see the shape of his shaft and the ridge of his head. As she stared, it twitched, straining against the fabric.

“That’s hot,” she whispered.

“See? I told you, it’s just a natural reaction to how tight this is.”

“Nothing to do with the clothes?” She scoffed.

“Nope.”

“You’re telling me,” she murmured, stepping closer, “that it doesn’t turn you on at all to be wearing Kiki’s leggings, that touched her the same way they’re touching you now?”

“No,” he protested nervously. “They’re just tight, is all.”

“You’re not even a little aroused,” she breathed, hooking a finger under the neckline of his shirt, and tracing the edge of his bra strap. “To be wearing Tiffany’s bra? Knowing that her little tits were in there right before you put it on?”

“N-no,” he breathed.

“Look in the mirror,” she purred, nudging his chin and meeting his gaze in the reflection. “You’re not excited by the sight of yourself? Look how good you look with a bit of lipstick.” She groped his padded chest. “Tell me you don’t like the way you look with breasts.”

“I, uh, I mean,” he stammered.

“How would you have felt if I’d given you my underwear?” She leaned closer, brushing her lips against his ear. “Would it turn you on to feel your hard cock straining against lace?”

“Fuck,” he groaned as she reached down, caressing the length of him through the leggings.

“Would you like that?” She pushed him against the wall, pressing her body against his. “We can do it now, if you want.” His cock throbbed in her grasp. “Do you want to wear my panties?”

“Okay,” he gasped.

“Yeah?” Her heart pounded. “You want that?”

“Yes,” he shuddered.

“Tell me,” she growled, squeezing him tightly. “Tell me what you want.”

“I—ah!—I want to wear your panties!”

“Good, take off your leggings.”

Eagerly, she stepped back, unbuttoning her shorts and stepping out of them. Ezra stared hungrily at her pink lace underwear. He unzipped his skirt and clumsily peeled off the leggings, kicking them both to one side.

They stood breathlessly before each other. His erection jutted forward, bobbing with anticipation. She started unbuttoning her shirt. He watched with wide eyes and followed her lead, pulling his shirt over his head until he stood before her wearing only a bra.

“Now you see why I couldn’t loan you mine,” she grinned, letting his shirt slide down her arms to reveal her bare breasts. His breath caught, and his cock twitched at the sight of her small, dark nipples, already puckered tight. She hooked her thumbs in the waistband of her panties and slowly lowered them.

“Here you go,” she said, offering them to him. “Sorry they’re a bit damp. You’re not the only one who’s excited.”

He took them from her, speechless, and held them up before him. It looked like he could barely believe what he was doing as he cautiously stepped in and pulled them up. She bit her fingertip as she watched the pink lace rise. It was deeply erotic to see him putting on her underwear.

When he finally pulled them all the way up, he let out a shaky gasp. The lace couldn’t contain his full erection, which jutted up past the waistband. He stared at himself in the mirror, wearing a bra and panties. He seemed to have forgotten that she was standing next to him, completely naked.

“Look at you,” she purred, stepping behind him and looking at his reflection in the mirror. “How does it feel?”

“Tight,” he gasped, cock straining against the lace.

“But how do you feel?” She slipped her hands over his sides, tracing the waistband.

“Sexy,” he breathed, barely audible.

“You are sexy,” she murmured in his ear. “You look so good like this.” Unconsciously, she pressed her pelvis forward, grinding against him from behind. Her nipples dragged down his back, sending little sparks of stimulation through her body.

He shivered as she reached around to touch him. As she grazed her hand over the head of his cock, he twitched and a squirt of precum lubricated her palm. She rubbed it against him, savoring the way he moaned for her.

“You look so fucking sexy wearing my panties,” she whispered.

Both of their gazes were fixed on his reflection, on the way he looked. She teased her fingertips around the rim of his head. His hands moved restlessly, sliding up his chest and over his bra, squeezing the padded cups as if they were his breasts.

She rocked her body against him, squeezing her thighs together. His skin felt hot against hers, and her body was crackling with tension. Unable to resist any longer, she reached into his panties to fully wrap her hand around him.

“Yes,” she encouraged him. “Look at yourself. You look so naughty wearing a bra and lace underwear as I stroke your hard fucking cock.”

He grunted, and braced himself against the mirror, gasping at his reflection. His cock throbbed in her grasp, and she stroked eagerly up and down the length of his shaft.

“You’re so sexy like this,” she moaned, squirming against his back. “I want to make you cum.”

His head glistened, smeared with precum, as he thrust enthusiastically into her grip. But his eyes were locked on his own reflection, as if he was fucking himself.

“Yeah, that’s right,” she encouraged him with a constant stream of filth whispered in his ear. “Keep going. You’re so hard. You must be close. I want you to blow your load all over that sexy bitch in the mirror. She wants it. Look how desperate she is for it.”

“Oh fuck, Syd!” He gasped, leaning against the mirror with two hands, repeatedly pumping his thick cock into her grasp. She moaned, feeling a wave of lust roll through her body as he strained, ass clenching against her pelvis. “I’m gonna…”

“Are you gonna cum for me?” She whispered urgently in his ear, praying no one would hear and interrupt them. All she wanted right now was to watch him cum, hard, wearing her panties. “Do it,” she begged.

“I’m cumming,” he moaned, as his entire body went rigid, just before his cock started pulsing in her hand. She squeezed the base as rope after rope of thick white spunk sprayed against the mirror.

“Oh yeah,” she squeaked, her body clenching excitedly at the sight. “Come on, Ezra! Cum all over her!”

After the first few powerful shots, he shuddered, and the rest of his cum spurted over her fingers. She leaned against him, happily milking the last of his orgasm, until he dropped to his knees on the floor. She followed him down, breathing heavily against his shoulder.

“That was awesome,” she grinned.

“Holy shit,” he panted.

She looked at their reflections in the mirror. He was rocking gently in place and gasping for breath. One bra strap had slipped off his shoulder, and the tissues had fallen out of that cup. Her arm was wrapped around his waist, hand snaked under the pink lace, still holding his softening cock. She saw herself peeking over his shoulder. His eyes were closed, and…

“Oh, Ezra, look!”

“What?” He glanced up and opened his eyes wide in surprise. “Oh!”

They’d collapsed down to where his cum, splattered and dripping down the surface of the mirror, looked like it had been sprayed across his face. For a moment, the illusion was convincing, and she seemed to be looking at a flushed young woman with cum all over her face.

“Look at that,” she laughed. “You gave her a facial!”

He didn’t answer, but his cock twitched in her hand.

“Okay,” she grinned, coming to a sudden decision. “Get dressed. We’ve got to go.”

“Why?” He struggled to stop looking at his reflection.

“Because,” she answered, standing up and pulling on her shorts. “We’re going underwear shopping.”

“We are?” He looked unsure as she buttoned up her shirt.

“Call it a graduation present,” she said, pulling him up and giving him a kiss on the cheek. “Now, hurry up. I’ll go tell Kiki and Tiff.”

“Okay,” he said, then hesitated. “Wait, Syd, what do you mean tell them?”

“Don’t worry, they love shopping!” She giggled as she slipped out the door. “Hurry up!”