A Bad Bet with a Playful T-girl

"Always!" She said with finality.

He looked into her smouldering eyes and took a deep breath. He couldn't believe he was going to do this. Equally he couldn't believe he hadn't done it sooner.

"Fine... I'll be your boyfriend."

A beaming Beth leaned in to plant a single soft gentle kiss on his lips, her face a picture of joy.

"Awww I'm so happy for you two," Alice cooed.

"Finally." Tom cried out, throwing his head back. "You two have been doing my fucking head in for years. You're always acting like an old married couple but without the sex."

"Sooo... exactly like an old married couple then." Alice interjected.

"Hey! We are not like an old married couple," Jack shot back somewhat tetchily, aware that this whole thing was spiralling out of his control.

"Yeah Tom, we've not even picked out the ring yet, the wedding won't be for months." Beth retorted playfully and stuck her tongue out at him.

Jack squeezed his eyes shut and rubbed his temple. This was going way too fast and they hadn't even checked out their bedroom compatibility yet or discussed the... mechanics? Still, at least she had stopped talking about dressing him up.

"Months Beth, Really?"

"Yes, months. I can't wait to see you walking down the aisle in your wedding dress." She grinned back, their friends laughing at her over the top antics.

"Argh, you just don't stop do you?"

"No. And that's why you love me."

He looked into her eyes to say something but the denial got caught in his throat. Once again the most infuriating thing about her was that she was right. Fuck it.

"Yeah well, maybe, whatever," he said leaning in to give her a quick peck on the lips before pulling back.

"I knew it," she cried and playfully launched herself at him, practically knocking him off the seat as he laughed and tried to push her back. "But you know I'm going to keep on kissing you now until you say the actual words don't you?"

"What! Hey stop that!" he laughed as she planted a flurry of wet sloppy and totally over the top kisses all over his face. Each one accompanied with a greatly exaggerated 'Mwah' done only for effect. "OK, OK, I love, I love you," he laughed, finally manhandling her back into her seat, "now get off me will ya."

Jack smiled and shook his head before remembering where he was and quickly trying to regain his cool and composure.

"Hey guys, can you cut out all that lovey dovey shit? I'm trying to keep my lunch down," Tom complained.

"Oh don't be so mean," Alice admonished, slapping his arm, "I think it's cute. Plus I'll get to be one of Jack's bridesmaids."

"Oh come on Alice," he cried out, the constant teasing was starting to get to him now.

"Oh sorry honey, I'll rephrase that... Plus I get to be one of Jackie's bridesmaids," she giggled.

Jack lowered his head to the table.

"Aww don't worry babe, they're only being like this because it's all new. They'll soon move on," Beth comforted as she rubbed his back. "So you just put your panties on and we'll say no more about it." Without looking up his hand snaked out from beneath him and he raised his middle finger. "Oh don't be like that," she cooed. "Mmm I'll tell you what, let's make a deal. You're so sure you have a bigger dick than me so let's get measured up. If you're bigger you get to be the one in control of our relationship, but if I'm larger... then I'll be the one in charge!"

He raised his head from the table.

"I don't want to control our relationship."

"Mmm, yeah that makes sense. Smaller penis, smaller balls, less testosterone, more submissive, less likely to want to be in charge. Probably why you sought out a nice hung girl like me to take you under her wing." He rolled his eyes as she turned his earlier words against him. "Oh that's right, you still think you're 'big' Jack and I'm 'itty bitty Beth'. Well? Care to bet on that?"

"And if I win you can drop the underwear?"

"Oooo yeah. I can drop my underwear right now if you wanna get down under the table for me babe. That definitely seems like a win-win."

Completely Ignoring that last part he stared at her in thought for a while, she seemed so sure of herself. Was this all a setup? No. Previous girlfriends had said he was big. They may have been lying of course. He only dated nice, kind people so he didn't think anyone he dated would ever tell him if they thought he was on the small side. He glanced at Beth. Ok, one person would tell him if they thought he was a bit on the small side.

Fuck it. Trans equals titchy, or at least below average. I'm bound to be bigger. He held out a hand and she eagerly took it.

"You're on."

Beth grinned and pulled a tape measure out of her handbag. Oh crap this was a bloody setup!

"Why do you have that in your bag?"

"Oh I have lots of things in my bag honey. The tape measure, some nice sexy undies in your size, a beautiful jewelled butt plug, a huge bottle of lube because... well... you're gonna need it. And of course... your brand new cock cage."

"My what!"

"Ha, that last one was a joke." She watched him relax again. "I've actually left your chastity cage at home." She winked. "Don't worry it's cute, you'll love it. I know I will."

"Ugh, whatever," he shook his head, she was always teasing him, always joking. At least he thought she was joking. She did have a bit of a manic grin. Yeah she was joking about locking him away. 100% sure. He looked at her again. 99% sure... OK maybe 98%...

Beth started giggling again as Alice grabbed the tape off her. "Ooooo this is going to be fun. I'm impartial so I'll do the honours." We'll measure up in my room before the big..." she turned to Jack, "...and small," she winked playful, "reveal." She got to her feet. "We'll do you first Jack so come on, get yourself hard, I'm certainly not going to be doing it for you."

"Well I can't just inflate on demand. I..."

"Don't worry babe I've got you covered," Beth interrupted, leaning forward to kiss him hard and deep, surprising him as she wrapped her arms around him and dominated his mouth. Her hand drifted downwards forcing its way into his pants as she squeezed and groped his buns. As soon as Jack started to get into it she pulled away, leaving him panting and flustered. She reached down into his lap to give him a little squeeze and grinned.

"That did the job. Well go on then, don't keep the girl waiting. Oh and you don't have to worry about me getting hard. I'll be thinking of all the kinky, deviant things I'm gonna be doing to you later when I properly turn you out."

He knew that statement should have terrified him but it only made him harder and it took all his willpower not to touch himself.

"Come on," Alice sang as she pulled the still dazed Jack up to his feet. "Destiny awaits."

**********

With a sinking feeling in his heart he sat at the table, watching the two giggling girls re-emerging from the bedroom. Beth seemed far too confident.

As Alice sat down all eyes were drawn to her.

"Ok the results are in and there is a definite winner. So... drum roll please," Alice requested. Tom responded with a quick rhythmic beating of the table, quickly rising in tempo to a final loud smack on the hardwood surface that gave way to an ominous silence... "And Jack is..." a cruel pause, "slightly bigger..."

"Oh thank god," he breathed out heavily.

"...than Tom," she giggled.

"Hey, no fair," her boyfriend complained.

"But he is a little bit smaller than Beth." Jack's face fell. "Only joking. He's actually a hell of a lot smaller."

Oh no-no-no. What had he done? Fuck. Although... disturbingly a little part of him had been really disappointed when Alice had teasingly implied he was bigger. How much of his own reluctance in all this was just for show. As he was staring into space pondering that awkward question Beth reached into her handbag and something burgundy with a little bow on the front was suddenly dangling in front of his face.

"Time to put on your new panties my darling."

"I umm. Huh, these are umm... not what I was expecting." He took the bikini briefs from her and turned them over in his hand. Apart from a little bit of a lacy frill around the edges and a tiny bow at the front they didn't look too different from the men's ones he usually wore.

"Oh really? Did you want something a bit more racy then? I'm sure Alice has something nice you can borrow."

"Umm no, no it's fine it's just umm..."

"What? You thought I was going to put you in something more skimpy?" She grinned. "Well I am. But as you know I insist on all my boyfriends wearing something a little girly at all times." She leant in close to his ear. "To remind them that even though I 'allow' them to walk around looking all alpha male and masculine outside the house, that behind closed doors they belong to a dominant trans goddess. That each and every evening they'll be on their knees servicing my big fat girlcock. Either slurping down my yummy cum or begging for me to fill their hungry little bottoms with my thick creamy load." She licked his ear causing him to shudder uncontrollably as she pulled away.

"Plus I don't actually want to embarrass you. These are discrete enough for no one to notice what you're wearing as they only have a slightly feminine frill around the edge rather than the blindingly obvious band of a G-string. Even if you did get caught in these you could just say you got dressed quickly in the dark and put my knickers on by mistake." She stretched out her arms as if yawning. "But we'll both know the truth won't we my dear. We'll both know you're wearing them because you're secretly my little bitch," she said with a smile and a playful wink.

"Umm yeah. Yeah that'll work... Thanks Beth." He said warmly, leaning in and giving her a tender kiss before wondering why he'd just thanked her. She was making him do this right? It was definitely Beth that wanted this and not him wasn't it?

Beth studied his face carefully and detected that slight look of disappointment she'd been hoping for. Perfect.

"Well... if you'd prefer I also have a nice lacy white thong you could wear." She grinned as she pulled the skimpy item from her bag. "Would you prefer to wear these ones instead?" She asked innocently.

"I umm..."

They swung back and forth temptingly on her finger as Beth waited, already knowing what he would choose. They both did. She just wanted him to make the conscious decision to pick the more feminine lacy pair. For it to be his choice to go further. It would make it so much easier for him to accept what she had in mind for him later.

He tentatively reached out and took them, a thrill of excitement running through him as he felt the material "...thanks Beth."

"You're welcome sweetie. Now go put them on."

He slowly got to his feet and as if in a trance began to trudge off towards his bedroom to change, a surreal fog clouding his mind.

"Oh no wait! Sorry babe you can't wear them," Beth called apologetically. "I'd have to shave you first as you're far too hairy back there for a thong and I'm not sure you're ready for that." She held up the burgundy bikini briefs. "You'll have to wear the plain simple ones instead." Beth shrugged innocently, trying not to smile too broadly at his obvious reluctance to hand over the lacy thong. "Or... well I suppose... If you really have your heart set on that lovely pair in your hand I could shave you now. Would you... like that?"

"I... umm..." She held him in her gaze and he stole a quick glance at Alice and Tom before looking back at her. Shit. Why did she always force him to choose? He blushed. "Wellll... You'd probably prefer to see me in these ones so umm..." She raised an eyebrow, making him say the words. "Err yes please. Can... can you shave me Beth? But err... just the crack right?"

"Of course sweetie. Let's get you all cleaned up and ready." She replied unable to help her eyes from lighting up.

Beth was trying really hard not to show how delighted she was, trying to maintain her cool and feign indifference. And she was failing badly. Everyone could tell she was as giddy as a school girl.

Jack smiled and turned his head away to hide his own growing excitement. Beth really was incredibly cute and fun and for some reason he found himself increasingly looking forward to this. To spending time with his new... girlfriend. Damn. Was she really his girlfriend now? He'd said yes to that earlier but once they left the cabin could he really go out with her? He'd have to introduce her as his woman to all his family and friends and they all knew who she was and what she was like. They'd know the position he would be taking in the relationship and it wouldn't be the traditional male one.

He rolled the thought of them as a couple around in his head, imagining them in a number of different social settings. He was pretty sure his immediate family would either be OK with it or at least act OK with it. He also knew she'd tone it down in less accepting company and in none of the scenarios playing out in his mind did the stigma or disapproval of random fuckwits even come close to matching the fun, enjoyment and companionship he'd have from being with her.

Yeah. Fuck it. She was his girlfriend and he wasn't going to be embarrassed about it. Nothing about this situation made him any less of a man.

"So how did you know he was so hairy?" Alice suddenly blurted out, cutting into his thoughts. "I know most men don't bother with a back, sack and crack but you still seem awfully sure of yourself." She grinned. "Beth... Is there something you're not telling me?"

"Well... You know I told you that we kissed at the party the other night? That wasn't actually the full story..." Beth leaned in and whispered into her ear while wiggling a finger.

"Oh you didn't!" Alice looked at Jack in shock before smiling and shaking her head. "Oh you naughty, naughty girl," she giggled.

Beth's eyes sparkled mischievously as she stood up, walked towards him and took his hand. "Come on, let's go and get you prepared. I want to see you all smooth and tucked into those pretty panties."

"I umm..." Oh crap. He turned bright red. Yeah OK, going out with Beth might make me slightly less manly after all.

Beth, sensing his renewed reluctance simply kept walking and pulled him along behind her, the less time she gave him to think about it the better.

She'd planted the seeds of the penis size conversation over the last few days, relying on his ego to force him into taking a bet that in his heart of hearts he knew he wouldn't win. So far everything was going like clockwork.

**********

"You jump in the shower babe and I'll join you in a minute. I just want to put a couple of things on our bed first," she said, pricking her ears and waiting for a response. 'Our bed'. Will he pick up on that and object? Remind her they had separate rooms?

"Yeah, OK Beth."

Yesss! She thought, we're spending the whole week sleeping in the same bed and bounced happily out of the door to prepare.

Jack looked at the shower with trepidation. For his whole life a shower had just been a shower but this one was different, it had a strange and potent energy about it. This one felt ominously like a cubicle designed for transformation, designed to wash away far more than just the sweat, dust and grime from his body. This was a portal into a whole new world.

He glanced back at the door and fought off a sudden impulse to lock it. That would upset Beth and he couldn't bear the thought of her being locked outside, sad and rejected. He shook his head, they had only been dating five minutes and already he was granting her full access to his life.

Turning on the water to heat up he began to remove his clothes as a new wave of excitement and anticipation washed through him. Beth was going to come in and join him in the shower and he was going to do whatever it took to make her happy. He took a deep breath and got into the little box of transformation knowing that he would be a different person by the time he came out. Beth would turn him into a different man, a happier man, a better man... even if that man was temporarily a woman. Damn. This was turning into a really fucked up bat shit crazy kind of a day.

**********

Beth returned wearing just a robe and with a deep breath and trembling hand reached out to grasp the door handle. She didn't think it would be locked but if it was then that might just spell the end of everything, game over. With a huge sigh of relief she felt the handle turn and stepped into the steamy bathroom to see her new man using the scented body wash she'd left out for him. The fuzzy outline of his body through the frosted glass gave her goosebumps as she bit her lip and allowed the dressing gown to slip from her shoulders. It was time to join him and let him see all she had to offer.

"Mmm you smell nice," Beth cooed, stepping into the spray and running her hand down his body. "I'm glad you used th... Umphh."

Jack turned round and kissed her lips, quickly darting his tongue into her mouth as it opened in surprise and wrapping her in his arms. He had spent every second he was in the shower thinking about Beth, imagining the smoothness of her skin, the sublime curves of her body, the softness of her large breasts and of squeezing that big juicy and gently yielding bottom of hers. Imagining what it would be like to sink to his knees and worship that glorious fat ass before driving his cock deep inside it. When she stepped in he couldn't hold himself back anymore. He was still the man in this after all so he should be the one to take control, show her she wasn't the only one who could be a top.

Beth allowed him to dominate her as he pushed her back against the glass panel and controlled the pace, kissing her as his hands explored. As they kissed they began to grind against each other, their cocks rubbing together and as they did the mood began to change. Jack still resisted looking down but could already feel the power balance beginning to shift back to Beth. Her cock simply felt bigger and despite not being able to see it he could sense its power and dominance, its need to be satisfied. He knew that a single glance down would be all it took for him to be lost.

Beth grinned into their kiss, she knew it too and began rotating her hips to strike his smaller manhood with her own heavier organ. Slowly but surely she began to take over the kiss, her tongue gradually pushing his back as she invaded his mouth. Moving forward she pushed and pinned him to the far side of the cubicle, her tits pressed against his chest. Jack's knees began to buckle slightly as he subconsciously lowered himself to surrender the height advantage to her. Twisting her hips forcefully she swung her mighty tool back and forth into his and was rewarded with a sweetly submissive moan.

Beth smiled knowing she had won this little battle for dominance. She wouldn't always win and she wouldn't want to but the opening rounds were only ever going to end one way. With her on top. It was almost time to claim her prize.

Withdrawing from the kiss she held his gaze, daring him to make a move. With his lip trembling his arm snaked down and they both gasped as he wrapped his fingers around her. His eyes widened as his hand drifted along its length. Oh shit! Is this real? When Alice said she'd had him beaten downstairs part of him still had trouble believing it, thinking even if she was it couldn't be by that much but she felt enormous.

"So what do you think baby?" She cooed.

"I... you feel so big!"

"Mhmm," she replied, reaching out to take his smaller one. "Mmm and yours feels really nice too. I could definitely have some fun with this one."

Jack glanced down and his eyes confirmed what his hand had already told him. She was significantly bigger than him in both length and girth.