One of the Girls

All characters in this story are 18 or older.

*****

"She's so hot," Mike sighed to himself, staring at the pictures on his phone.

The current one showed himself, with his neatly-trimmed brown hair and gentle hazel eyes, and a gorgeous woman next to him, with long, wavy golden-blonde hair and blue eyes, and a dress that was revealing quite a lot of cleavage. They had their arms over each other's shoulders, smiling to the camera.

He continued swiping through the photos, swooning over his attractive friend. Most of them were her and her alone, posing at a bar or nightclub, where she liked to frequent. Mike wasn't very fond of those places, but he loved Tiffany, and so he went where she did, even though she seemed oblivious to his feelings.

Suddenly, his phone vibrated and over the picture he was currently ogling, a notification appeared: 'One unread message from: Tiffany.'

He nearly dropped his phone in surprise. He suddenly felt guilty, as hers were the very pictures he had just been looking at. He shook this feeling off quickly however and opened the message.

'Hey M! Wanna grab a quick drink tonight? Could use one before I head out for my girls' night!'

Mike sighed. 'Before I go out for my girls' night', he thought. He always felt like just a buffer, just the pre-party to warm her up before she went out and really had fun. He'd always been too nervous to profess his feelings however, and so he couldn't really blame anyone but himself.

He slowly typed out the reply: 'Sure. That sounds fun.'

But his finger lingered over the send button. He stared at his phone, deep in thought. Then, he made a sudden, rash decision. He deleted what he'd typed and instead tapped up a new message: 'Can I join your girls' night too?'

He hit Send before he could begin to even regret the decision, and let out a long sigh, leaning back in his chair. As the minutes ticked by, he began to grow nervous, thinking maybe he'd finally took too far a leap. Just when he began to lose hope though, his phone buzzed once again. He looked at the message expectantly.

'That sounds like a lot of fun. Be at my place at 6. ;)'

For a long time, Mike simply stared at his phone. Had he actually asked to join Tiffany for a full night of fun, and had she really agreed to it? And not only that, had she really invited him to her place? He reread the message several times to make sure he wasn't hallucinating. Once he was absolutely sure he'd indeed read it right, he finally let out a little celebratory shout.

"Yes!"

He practically jumped up from his chair to get ready for the evening.

--

A little over an hour later Mike arrived at Tiffany's apartment. He rapped his knuckles on the door and shifted his weight from one foot to the other nervously. After only a few seconds of waiting the door swung open and he was met by Tiffany's beautiful, tall frame. Even without her heels she stood a few inches taller than he did at 5'11".

Mike had trouble keeping his jaw from dropping when she came into view. She was only clad in a sheer pastel pink camisole that went just beyond her panties, revealing nearly every inch of those long legs and quite a bit of cleavage. He could even see her nipples through the thin material.

"Come in, won't you?" She offered with a sweet smile.

Her voice dragged him back to reality. He shook his head for a moment, and then nodded.

"O-oh right, of course! I'm er...I'm sorry, am I too early?" He asked sheepishly, stepping inside.

"Not at all, love," Tiffany said, smiling sweetly. "I'd say you're right on time."

Tiffany turned around, placing her hands on her hips and looking up and down Mike's figure. Mike cleared his throat nervously, trying not to stare at Tiffany's chest.

"O-Oh. Th-that's great, then," was all he could come up with in reply.

Tiffany giggled and her smile widened.

"I hope you don't mind, but I still plan for this to be a girls' night," she said delicately.

Mike thought for a moment, trying to make sense of this. She'd invited him over and said he could come, but then what did she mean by a girls' night? He cleared his throat again and nervously managed to speak up.

"I don't understand," he finally replied.

Tiffany leaned over slightly, revealing even more cleavage as she blew him a little kiss and whispered, just inches away from his face.

"Have you ever worn women's clothes, sweetie?"

"N-No," Mike stammered, his brain trying to process the question fully.

"Would you like to try tonight?" Tiffany asked, edging just a bit closer, staring deeply into Mike's eyes. "For me?"

Mike had never entertained the idea of dressing up in women's clothing before, even though he had the figure for it. He had always been rather thin, never having been that athletic, and wasn't the tallest man in the world, either. Still, this was Tiffany, and he knew he'd do just about anything to be with her, and so he nodded his head.

"O-Of course Tiffany. Anything for you," he whispered back.

"Oh good!" She clapped her hands excitedly. Taking him by the hand, she led him into her bathroom, where he could already see she had clothes laid out for him, as well as a razor and shaving cream.

"I'm going to go get ready in my bedroom. Get yourself nice and smooth and then meet me in the living room, alright sweetie?"

"A-alright," Mike replied, more nervous than ever.

Tiffany gave him a tender kiss on the cheek and departed, closing the bathroom door behind her. Mike looked over the supplies that had been left for him and leaned against the sink. He loved Tiffany so much, but was he really willing to dress up like a woman for her? And go out in public like that no less? What was the worst that could happen, he thought to himself. Maybe Tiffany liked crossdressers, and by doing this he'd just be making himself irresistible to her?

"Fuck it," he said firmly, stripping out of his clothes quickly. "Let's do this," he said, strengthening his resolve.

He turned on the shower and after getting the water just right, hopped in and began to clean himself off and go through the process of shaving. He wasn't very hairy to begin with, so this process luckily didn't take him long. He got every nook and cranny, making sure his entire body, save for the hair on his head, was smooth and shaven.

After drying off he finally got around to looking at the clothing. He wondered how and why Tiffany already had things in his size, but regardless, began to get dressed. He sat on the edge of the tub, rolling up the black fishnet stockings first. Once the lace tops were snugly situated around his thighs, he moved on to the other undergarments. He started with the black lace thong, which had a front large enough to hold his penis and sac, which he found strange. Regardless he slipped it up his legs and was amazed by how good it felt as the fabric settled between his cheeks.

The bra, a black lace number that matched the thong, took him a moment to put on. He tried to snap it behind his back several times but eventually gave up, spinning it around to the front. He finally clasped it together and then spun it back around, pulling the straps up and situating it properly. He noticed then that the cups were padded, and gave him the appearance of a small but perky chest.

Finally, he slipped into the slinky black dress she'd left for him. It was a cute halter design and the straps fit snugly around his neck, and barely covered the tops of the fishnets. He smoothed out the front and looked at himself in the mirror. He saw what looked to be a hot girl in a little black dress staring back at him, though he definitely knew he could use a few finishing touches. He decided to go all in for Tiffany, and after minimal searching, found her makeup stash.

It took him several attempts to get it just right, but he managed to apply just the right amount of blush, mascara, eyeliner, gloss and eye shadow to make him look even more sultry and feminine. Extremely proud of his work, he smiled sweetly at his reflection. Lastly he went about styling his brown hair. It wasn't very long, but he still managed to fashion it into a little pixie cut. He couldn't believe how different he looked. If he didn't know any better, he would've thought he was actually looking at a petite woman in the mirror.

For the finishing touch, he slipped into the three-inch shiny black heels Tiffany had left for him, and practiced walking in them. The heels clicked on the floor as he teetered back and forth across the bathroom, but in no time he was sauntering in them like a pro. He couldn't believe how hot and natural he felt dressed up like this, and was actively trying his best not to get hard.

After taking just a moment to compose himself, Mike finally exited the bathroom, only to find Tiffany sitting on the couch waiting for him. As she stood to examine his appearance, her jaw dropped. While she herself looked absolutely stunning in a low-cut red dress with a pleated skirt and sheer black thigh highs with red heels, Mike looked just like a young woman. His mostly flat chest and pixie haircut made him look even younger than he was, and Tiffany smiled ear to ear.

"Oh sweetie, you look like an absolutely delicious little slut," Tiffany exclaimed, walking over and circling Mike, eyeing every inch of his feminized body.

Mike could feel his cheeks flush, and smiled shyly.

"You even did your make up and hair! You're a natural," she added in. "Now, what should we call you, I wonder?"

"C-Call me?" Mike stuttered. Even dressing up as he had, he hadn't considering picking a name for himself. Luckily, Tiffany was one step ahead of him.

"Let's go with...Mikayla!" She said happily.

"M-Mikayla?" Mike repeated, sounding unsure.

"You don't like it?" Tiffany asked with a cute little pout.

"N-No, I like it! It's...it's sexy," Mike admitted.

"Are you ready to go then, Mikayla?" She asked sweetly. "We're going dancing with my friend Carla."

Mike recognized the name immediately. He'd met Carla on several occasions when hanging out with Tiffany. She was a spunky little thing, only about 5'4", with small but very perky breasts. She had long, silky jet black hair and piercing green eyes, and had a habit of wearing skimpy dresses that didn't even fully cover her thighs. To Mike she had always been equal parts adorable and sexy, but still didn't compare to Tiffany. He began to wonder if she'd recognize him in this getup.

"Will she...be okay with this?" He asked nervously.

"Oh I think so," Tiffany said with a devious smile. She patted Mike on the butt and collected her purse, clicking on her heels over to the door and opening it for Mike.

Mike smiled, still feeling nervous, and teetered on his heels out the door.

--

Tiffany drove Mike to the club, who nervously kept adjusting the edge of his dress so that it covered his stocking tops. This made Tiffany giggle.

"Relax, sweetie. You look hot. Every eye in the club will be on your sexy little body."

Mike blushed just thinking about that, wondering if it were true. He didn't have to wait long for confirmation though. In minutes they arrived at one of the many local nightclubs Tiffany liked to frequent. As they approached the door, the bouncer held up his hand and Tiffany extended her ID, then leaned over to whisper in his ear. Mike bit his lip, wondering what this was about, and suddenly saw the bouncer grin. He stepped aside, and both Tiffany and Mike went inside. Carla was waiting for them at the bar, already halfway into an appletini, dressed in a skin-tight, strapless silver dress, and glittery silver heels.

"Tiffy! And you brought..." Carla paused, the realization hitting her of just who it was Tiffany had come with. "...a new cutie to dance with us! What's your name, doll?" Carla asked with a sly smile.

Mike cleared his throat, trying to summon his most feminine voice.

"Mikayla."

"Well you're super cute, 'Kayla!" Carla said, swatting Mike's ass through the thin material of the dress. He jumped slightly, and blushed even more.

"Shall we?" Carla asked, nodding towards the dance floor.

They each had a few quick shots and then trekked out onto the dance floor. Tiffany and Carla started, sensually gyrating to the rhythm of the infectious beat together. Mike stood off to the side, nervously, watching them dance, until the ladies pulled him in and helped him find his stride. Before long, and with the help of a few more shots, he was dancing just as sexily as they were, enjoying being between the two gorgeous ladies, even dressed up as a woman himself.

Over the course of the night, he noticed several guys, and even a few women checking him out as he danced with Tiffany and Carla. He wondered if they knew he was a man, or if his clothing and makeup were so convincing, they saw him as the sexy woman he felt like. Regardless of their looks or desires, Tiffany and Carla were the ones to go home with sexy Mikayla that night.

They were all feeling a little tipsy as they stumbled into Carla's apartment. The ladies pushed Mike onto the sofa and giggled. Tiffany then pushed Carla down to sit next to him.

"You know what I think would be really sexy?" Tiffany asked, leaning over so that both Carla and Mike could see most of her breasts pressed against her dress.

"Carla, you should suck his dick, and then he could return the favor."

Mike's eyes suddenly went wide, as he looked between Tiffany and then Carla, and he gasped as Carla quickly pulled up his little black dress, revealing the bulge in his thong.

"I...uh...um..." He stuttered. The woman he'd always wanted was Tiffany, but he couldn't deny that Carla was gorgeous too, and if this was what Tiffany wanted to see, perhaps she'd join in.

Mike gulped as Carla situated herself on her knees and leaned over his lap, pulling the front of the lacey thong aside.

"Oh Mikayla, your girlcock is so sexy," Carla giggled.

"G-Girlcock?" Mike stuttered, still struggling to comprehend what was about to happen.

Carla opened her mouth wide and engulfed his achingly hard cock in one go, her lips tightly wrapped around the base. Mike groaned, feeling the head at the back of her throat in an instant; her warm, wet mouth enveloping every last inch.

"Ooooh C-Carla.." Mike moaned, leaning back on the couch, letting himself relax.

Mike was in total disbelief. Here he sat on Tiffany's couch, all dolled up in lingerie and a slinky dress, while their friend Carla sat on her knees, completely swallowing his cock and slurping up and down it's length with abandon, all while Tiffany excitedly watched on just feet away.

"She sucks cock well, doesn't she?" Tiffany purred, stepping closer.

"Y-Yeah.." Mike replied, somewhat shyly, even in the midst of what was happening.

Tiffany leaned down, grabbing a fistful of Carla's silky black hair and pulling her head up and down Mike's shaft roughly. Carla gagged briefly but made no attempts to stop, slurping up every inch of meat offered to her as Mike simply moaned and watched the show.

"She is, isn't she? I'd know," *Tiffany giggled, tightening her grip on her friend's hair.

"You mean you two have..mmmm..." Mike trailed off with a moan as Tiffany worked Carla's head faster over his length.

"We might've fooled around a little, isn't that right babe?" Tiffany giggled, releasing Carla's hair.

Carla slurped all the way up Mike's cock, releasing it and licking her lips hungrily.

"Don't be coy now babe, we've fucked plenty of times. And talked about letting him join in, if he could handle it."

Without another word Carla began blowing Mike again, slurping up his cock and messily drooling over it. The entire thing shone with her saliva, and some even trickled down her chin as she took it repeatedly into her throat.

"I-I can handle it," Mike said, trying to sound confident, though he'd never been with two women at once before, let alone two as hot as the pair he was currently with.

Carla slowed her sloppy sucking, dragging her lips along Mike's skin until only the head remained, circling it with her tongue a few times before finally releasing it altogether and wiping her mouth with the back of her hand.

"Are you sure about that, babe?" Carla asked with a wicked grin.

Mike was harder than he'd ever been in his life, and both of these gorgeous vixens were looking at him intently, Carla still kneeling between his legs, her fingers tracing gentle patterns over his fishnets.

"I'm down for whatever you two wanna do," Mike smiled, nodding confidently, his dick giving a little twitch of excitement.

"Glad to hear it," Carla grinned and stood up, taking a step back to stand next to Tiffany.

"Let's show him what we've got," Carla said, her wicked smile widening.

Both ladies pulled up their dresses and slid aside their panties, revealing huge, cut cocks that were as big as Mike's. His jaw dropped and his eyes went wide, though he remained just as hard. He had no idea that either of them were transsexuals, and though he'd always been straight as a razor, he was still insanely horny and still found himself wanting Tiffany just as bad as before.

"I...I..." He stammered, trying to find the words.

"Now now baby, it's not polite to talk with your mouth full," Carla said with a grin.

"W-What?" Mike asked.

Carla slid off her shimmery heels and climbed up onto the couch, her swinging she-cock right in front of Mike's face now. She reached down, running her fingers through his brown hair and pressing it against his lips. Mike hesitated but opened his mouth and she slid inside quickly. He winced and gagged at the sudden intrusion, but Carla gripped his hair between her fingers, her evil smile returning.

"Get used to your gag reflex Mikayla. You're going to need it, you little slut."

Carla slowly pulled her cock out of Mike's mouth, letting him catch a breath before thrusting it right back in. Again he winced, trying to overcome his reflex. He tried to relax his throat as Carla again pulled her hips back only to thrust them forward once more. After a few more times he'd gotten used to it, and began to enjoy having a nice, thick cock being shoved into his throat. He felt so confused; he wasn't sure if it was the booze or if he was just that horny, but he was beginning to feel it was a pleasant mixture of both.

Carla was fucking his face with a nice rhythm now, sliding her rock hard girlcock between Mike's painted lips, until it shone with his saliva just as his had with hers. Though Mike's view was obstructed by Carla, behind her stood Tiffany, jerking off her own cock, watching her slut of a friend fuck her best friend's face. She pumped her fist rapidly, groaning in pleasure at the sight before her. She knew it wasn't enough however.

She slowed her working hand and licked her lips, kneeling down between Mike's legs and taking his cock within her mouth without a word. Mike had gotten comfortable letting Carla fuck his face and closed his eyes, but they shot wide open when he felt another warm, wet mouth close around his cock. Though he couldn't see it, he knew it had to be Tiffany, and groaned around Carla's shaft, unsure if he could feel any better than he did now.

"Oh fuuuck, you little slut, I'm about to cum," Carla announced, her hips thrusting a bit faster, driving her hardness into Mike's mouth faster and faster. "You want my cum don't you, you little slut? You want to taste it and swallow it all down. You're just a little shemale slut like us, aren't you? Ooooohh ffffuuuuck, Mikayla, get ready!"

Mike's cock twitched between Tiffany's lips at these words. He considered feeling ashamed but instead felt anything but. He suddenly desperately wanted to taste Carla's cum, just as she said. He wanted to feel it in his mouth, on his tongue, tasting it and swallowing every last drop until he'd sucked her dry. He didn't have to wait long.