A First Time for Everything

"You know, when I bought this I kinda hoped *you* would be the one wearing it tonight."

"You told me you'd do anything for me tonight, right? 'It's your birthday, babe, and I'm totally at your disposal.' Exact words, there."

Michael looked in the mirror and sighed. She was right, of course, and he should have known by now that things rarely, if ever, went his way. Not that he had much of a problem with it - Sydney was great, and it's true, he'd do anything for her. But this...

As if reading his mind, Sydney said "relax, babe. This'll be fun! And you look amazing in it."

"Amazing" wasn't quite the word he had in mind at first, but he appreciated the encouragement. The black bodice strained to contain him, giving the impression of a sizeable bust and a slim, hourglass shape. From behind he was sure it looked a hot mess and could feel his love handles squeeze out between the strings that struggled to give him a ladylike figure.

Down below, however, was where things started to get a bit weird, at least for him. Before today he'd never been compelled to shave his legs, yet had somehow been convinced to go completely bare. Completely. Sydney had then made him tape his balls back and wear the bottom of the piece, a sleek leather bikini and mesh leggings which he found did little to flatter his, in Sydney's words, "thunder thighs." He thought that might have been a bit much - lacking much in the way of definition, sure, but hardly a force of nature.

He had made a point of not looking at his face, worried that he'd be disappointed.and that the illusion, such as it was, would fall completely apart. Sydney had made him close his eyes as she'd worked her magic, and in hindsight he appreciated it. The effect was so striking that it almost brought a tear to his eyes. He'd never had the most masculine features or been overly concerned with his manliness, and had for a long time wondered if he'd been born into the wrong body.

His lashes had been plucked and set, his makeup applied tastefully, and on his head sat a royal purple wig that gave him the long, luscious locks he'd always dreamt about having but had never had the courage to try. For the first time in his life, he felt hot - what he saw in the mirror reflected what he saw in his mind's eye when he was being honest with himself.

The two stood there in silence for a time, before Michael said, softly, "thank you."

Sydney looked up at him lovingly. "We're just getting started, Michelle. Come on, there's someone I want you to meet."

Michelle? he thought to himself. Simple enough. Works. I'll take it.

Sydney took his hand and led him into the bedroom as he wondered just what else she had in mind for the evening's entertainment.

--

She led him to a room in her mansion he'd never been in before, and it was immediately apparent why: it was completely filled with toys and devices of various sizes and shapes; furniture, or what appeared to be furniture, with restraints and attachment points; and, he was somewhat relieved to see, a rather large container of lubricant. So there's that.

"Now are you going to be a good little girl and cooperate, or am I going to have to get rough?" said Sydney as she flashed a mischievous grin.

"I'll be good," said Michael, his heart pounding. He never would have guessed that a passing mention of an interest in crossdressing and being dommed would have turned into this, and he wasn't entirely sure he was ready for it. Still, he trusted Sydney and had decided to give it an earnest shot.

"Hands behind your back, then," said Sydney as she pulled a leather armbinder out of a nearby closet. "Let me know if it gets too tight."

"OK," said Michael, who winced a little as she cinched the binder tighter and tighter.

Satisfied with her work, she retrieved a spreader bar from the same closet and went about fastening it to his ankles. She then bent him over at the waist and attached his binder to a winch in the ceiling and cranked it until he was completely immobilized, bent at a 90-degree angle and his legs spread to double his shoulder width.

It was an uncomfortable position, to be sure, but Michael could feel himself getting more and more turned on with every passing moment. He was always such a nervous person, planning and evaluating every possible permutation of every possible scenario, regardless of their chances of actually occurring, and he found it supremely refreshing to relinquish control so utterly. Whatever happened now was, quite literally, out of his hands.

"Wait here, hun, I'll be right back with a special guest."

Wait, what?

"Sorry, what?" said Michael, who hadn't expected any company this evening. "I thought it was just the two of us..."

"Well, you thought wrong, my dear. My birthday, my party, remember?" said Sydney as she left the room and turned off the lights, leaving Michael alone with his thoughts.

What on earth did I get myself into?

--

"Still awake, my dear?" said Sydney as she entered the room, her guest trailing behind with a large bag in her hands. "I know we took a bit longer than promised, but she looked so good I just couldn't help myself."

Michael twisted as much as his restraints allowed but couldn't see Sydney's guest. Sydney continued, "I believe you two have met before?" as the guest stepped into his field of view.

"Megan?" said Michael. "I'd, uh, shake your hand, but..."

"Hey, beautiful!" said Megan, her voice pitched a little higher from excitement. "Oh, Sydney, I just love what you've done with him!" For emphasis she slapped him on the ass and giggled.

"He was quite cooperative," said Sydney. "He's good like that. Could you join me over here for a minute?"

As Michael's eyes adjusted to the light, Sydney and Megan spoke quietly back and forth, just outside of his audible range, and his heart started pounding in his chest.

Megan? From the bakery? I'll need to find a new one. I can't let her see me again after this!

"Have you ever sucked dick before, Michelle?" asked Sydney out of the blue, snapping Michael out of his distracted thoughts.

"No," said Michael, who no longer cared about finding a new bakery.

"What about a prostate massage? Have you ever cum from being penetrated?"

"You already know I haven't! This isn't what I had in mind at all, Sydney."

"I know, babe, but I didn't ask," said Sydney. "Megan, gag him?"

Michael thrashed to what little extent he could, but quickly recognized the futility of it. However, despite himself, he was rock-hard and could feel his dick dribbling pre-cum.

Sydney knelt down next to him and held his face steady as Megan slipped the rubberized ring behind his teeth and fastened the gag behind his head. Sydney stroked his cheek several times and whispered in his ear, "trust me, OK? I love you."

He knew from long years of experience that if it was up to him, he'd never try anything new. Sydney's approach was the polar opposite: just fuckin' do it. He knew deep down that Sydney was only giving him exactly what he wanted but wouldn't ever feel comfortable seeking out himself.

Megan stepped in front of him again and gently held his head back so he could see the height of her. He'd always been fond of her, flirting with her whenever he stopped in to grab coffee and a snack - he hadn't known that Sydney knew her, too! His heart pounded in his chest as she smiled down at him. "Like what you see?" she said, still smiling.

"Uh ooo," he said, more or less.

Michael could feel Sydney behind him now, stroking his buttocks gently with her fingertips. "Tell you what we're going to do, babe: we're going to have a race."

"Uh ahe?" he said, causing Megan to giggle.

"Megan, show him," said Sydney, as Megan started pulling down her miniskirt to reveal the biggest dick he'd ever seen in person.

Fuck me, it's bigger than mine. Goddammit.

Michael strained his neck to look up and could see Megan blush.

"You really didn't know, did you?" said Sydney, to which Michael replied with an affirmative grunt.

It never came up in the bakery, amazingly enough.

"I figured this might make your first time giving head a little bit easier," and Michael found himself nodding his head ever so slightly. She wasn't wrong, really.

"So, the race: I'm going to penetrate you, and you're going to blow Megan. If I make you cum before you satisfy her, you lose. If she finishes first, you win! We might even let you down to play with us for the rest of the night. But you'd better swallow everything she gives you, Michelle, or you'll have to be punished. You will *not* enjoy that."

And then, without further warning, he felt Sydney pull his skirt down and start pressing against his ass as Megan took her rapidly swelling penis and rubbed it on his face. Had the gag not been present he would have asked what he was supposed to do without use of his lips, but luckily for him, Megan seemed to relish the chance to use his mouth as her own personal pocket pussy. Without warning she grabbed him by the back of his head and jammed all 8 inches into his mouth at once - it was all he could do not to choke as she moved her hips back and forth, her cock sliding in and out of his mouth. He did what he could with his tongue, teasing the tip and the length as she face-fucked him.

Not to be outdone, Sydney breached his anus, not particularly gently, and he felt his vision blur with the intensity of the feeling. He'd experimented with his finger, but whatever size dildo she was using, it was way fucking bigger than that. It wasn't altogether unpleasant, just overwhelming at first.

"Feel that, Michelle? You're no longer an anal OR oral virgin. Congrats, honey."

"Glk glk glk," said Michael, whose concentration was somewhat divided. "Glk."

"You told me you wanted a threesome with one of my friends, right? Think how lucky you are!"

Not quite what I had in mind, but... not entirely unenjoyable, either.

If Sydney was the talkative one, Megan was all business, her tempo increasing gradually, her grip on his head growing tighter and tighter as he felt her dick start to twitch.

"And just think how popular this video will be when we upload it!" said Sydney with a hearty laugh.

"GLK GLK!!" said Michael as he tried to turn his head to the side and look her in the eye, but Megan would have none of it. She took her dick out of his mouth fully and slapped him across the face with it, marking another new experience he'd now had.

"Boyfriend tricked into being spitroasted by girlfriend and her trans friend," said Sydney as she pumped away. "What do you think of that for a title? How do you think the audience will react when they see her dick's bigger than yours?"

It was all too much for him to bear. His heart was racing, his dick was starting to twitch, between the humiliation of being recorded and penetrated at both ends - it was almost too much to bear. He heard Megan's impassioned grunts and felt her thrusts grow ever faster, then suddenly she pulled his head forward as she slammed her dick all the way up to the base in his mouth. Just as well, as Sydney had started stimulating his dick with her hands - he knew he was seconds away from losing the race, not to mention what remained of his dignity.

But oh, that dignity. Megan's dick started spurting thick, impossibly thick, ridiculously thick ropes of cum directly down his throat - like the diligent cock-slut he'd become, he swallowed it all, which was enough to make his own dick pop, spilling jizz all up the front of Sydney's new bodice.

"Did he lose?" asked Sydney.

"Nope," was all Megan could say as she pulled back and out, but not before ensuring she'd drained every last drop of semen into his gaping mouth. "This boy's a keeper, Syd."

"Tell me about it," she said.

I could really use some ice.

--

The three of them lay in bed later that evening, sweaty and satisfied. The sheets were a tangled mess at the base of the bed and a cool breeze blew in through the open window above them.

"Oh!" said Megan, sitting up abruptly. "I forgot the cake! I'll be right back."

As she padded across the carpeted floor and left the room, Sydney rolled on top of Michael and squashed her breasts into his face. "You were really good tonight, babe. I'm proud of you."

"Thank you," he said. "For everything. Although next time, if you're going to record it, at least let me know? I could've worn something over my head, maybe."

"Oh, come on, it was spur of the moment teasing. There's no video! I'd never do something like that to you."

Michael exhaled a huge sigh of relief. "Damn near stopped my heart when you said it."

"Well, it seemed like a good idea at the time," said Sydney, as they both laughed and kissed.

A few minutes later, Megan returned with 3 plates and 3 large slices of cake which the two of them sat up to receive. Megan sat on the edge of the bed and placed her plate beside her.

"Happy birthday, Syd!" she said, while Michael took his first bite of cake.

Not bad at all, but a bit salty... wait.

"I, uh, can't help but notice you two just staring at me," he said as he swallowed.

The two girls looked at each other and burst out laughing.

"There's cum in this, isn't there?"

"Batter and frosting!" wheezed Megan between guffaws.

"Oh, for fuck's sake," said Michael, not quite able to keep himself from chuckling. "Still tastes good."

When they finished laughing they took up their plates and started eating, too, in what he imagined was good humour. Or, they just really liked cake.