A Bad Bet with a Playful T-girl

"Well yeah, of course I do, it stands to reason doesn't it?"

"Really? And you're sure about that are you?"

He looked at her, the smirk on her face told him to be wary but they had already started down this road and the amused look on their friends faces was making this hard to walk away from. And besides. Of course he would be bigger than her. It stood to reason didn't it. Beth had always been a force of nature, strong willed, assertive and a natural born leader. She was a natural top. But she was also trans so she was bound to be smaller.

"Yes. Definitely. There may be a few girls with big cocks when you go on those shemale porn sites but almost all are a lot smaller than average. And that makes sense. If you're inclined to dress up and want to become a woman then you probably have lower testosterone levels, ergo, more likely to have a smaller cock and balls. So yes. I'm pretty damn sure that my dick is bigger than your dick."

Ugh. How did he even get into this ridiculous 'my dicks bigger than your dick' debate? They weren't pimply adolescents for fucks sake they were supposed to be adults!

"Uh-huh." Beth's eyes lit up. "So you watch a lot of transexual porn then do you?"

"What? NO! I..." He looked around to see a number of raised eyebrows, shaking heads and broad grins. "Well..." His face was turning bright red. How the hell could he get out of that little admission. "Well after we met and I got to know you I was a little curious so I checked out a website or two. You know. Just once. Just to see." He wasn't convincing anybody and he knew it.

"Oh yeah?" The excitement was clear on her face. "So you became curious after meeting me and simply couldn't resist checking it out? Wondering about the size of my package. Oh you have no idea how pleased I am to hear you finally admit that, but tell me." She purred. "How long have you been thinking about me in that way?"

Oh fuck! That certainly wasn't the off ramp from his 'I watch transexual porn' admission he'd been hoping for and if his face got any hotter it'd probably ignite.

He gulped. "Well I umm..."

She smiled as he instinctively reached up to loosen his collar, as if aiming to release the steam that her mere presence was causing. She loved to get him all riled up like this, she didn't manage it too often but when she had the upper hand like this she would always tease him mercilessly. It was so much fun and she knew he'd do exactly the same to her if their positions were reversed.

She continued to watch as he blushed furiously. Mmm, he's such a little cutie, she thought while running her eyes over his lithe body, her smile growing wider. And if all goes to plan I'll have him looking so much cuter by this evening...

**********

Jack had known Beth for about three years and they had always got on really well. During most of that time he'd had one steady girlfriend whereas she'd had gone through quite a few boys and girls. As they were both attached and unavailable throughout most of their time together they had the advantage of just being able to relax and be themselves. They'd been able to develop a fun and platonic friendship but also one which included a large dose of safe and enjoyably flirty banter.

She had always joked that even though she was the trans one she would still be the man of the house if they ever got together. That she would be the one wearing the pants while he wore the panties. That she'd turn him into her perfect little housewife.

Ha. Yeah right, whatever, like that was ever going to happen.

They spent so much time together that people were always commenting on how they seemed way more than just friends. Jack had always shrugged it off, despite being the same age he'd always seen her more like a big sister and up until now he had been sure she felt the same way. He now realised that if she did view him as a sibling then she had a completely different idea of what constituted a normal relationship between a brother and sister.

For the last month and the first time ever they had both been single. Jack had finally split from Janet, his long term girlfriend and Beth had immediately jettisoned the guy she'd been seeing. Ever since she had been making her interest in him crystal clear and all that innocent flirting of the past had suddenly gained a new significance.

He was now constantly on edge around her as she used any excuse to get close and brush up against him. Every lingering touch caused his heart to race, his loins to throb and his stomach to twist. He'd seen how she was with her previous boyfriends though. Fun, sweet, kind and loving but also so very clearly dominant. The three big questions he had were... Could he resist her? Did he want to? And, if he did go for it, could he cope?

A week ago while they were at a party together, she finally found the courage to make her opening move...

**********

"Come on, I love this song, let's dance!'' Beth cried, pulling him from his seat and dragging him to the makeshift dance floor.

Beth began gyrating up against him, invading his personal space and holding him closer than normal as he struggled to hold her off in an 'I'm not holding you off' kind of way, praying for the music to change to something less intimate. After initially fending her off for the duration of the love song they stayed on the floor, dancing for ages. Sometimes wildly and stupidly with all the twists, turns, pirouettes and terrible singing they could crowbar in. Sometimes up close and personal. And sometimes, rarely, they even danced well.

They could both sense the atmosphere changing. Beth and Jack were almost always the first ones up when the music started but this time it felt very different. There was no group, no boyfriends or girlfriends, just the two of them dancing together. For them it felt as if everyone else at the party had simply ceased to exist. There was a new tension between them, a fire and intensity in their movements, their eyes rarely leaving the others' gaze. Every time their bodies brushed against each other they could feel the electricity and desire building.

Beth could see the internal battle in Jack as he tried to resist her. After all this time she was so close to landing her man. His resistance was crumbling but she needed to get him somewhere quieter where he would feel more comfortable and less self conscious. It was time to get him alone for their first kiss.

"Come on Jack, let's go and get another drink."

She dragged him into the hallway before spinning him around and backing him up into a corner beneath the stairs.

"Fuck Jack, I want you so badly," she growled and went for it.

Beth quickly darted her tongue between his lips as they hungrily made out for the first time, full, drunken, deep and passionate. He willingly surrendered control, allowing her to dominate his mouth, her hands to roam his body, letting her pull up one of his legs to wrap it around her as she groped and squeezed his bottom.

"Oh you have no idea how long I've wanted you," she moaned as she finally broke away, "And you're such a good kisser, such soft lips." She slowly traced her index finger around them, "so soft. I wonder what else you can do with those pretty lips of yours." His mouth opened invitingly and she quickly pushed it in, moving it back and forth along his tongue, a wide smile on her face as he instantly began sucking on it. "Oooo good boy... or maybe I should say good girl?"

He glared at her but to Beth's delight he continued to suck on her finger. Like the good little girl she knew he could be.

"What?" she asked innocently. "You know I've always wanted to get you out of your pants and into my panties. And I mean that literally," she grinned. "I'd love to dress you up. You'd look so good in some pretty lacy panties, maybe some nice high highs with a cute skirt and a pretty top, all femmed up. Down on your knees or bent over a table for me. Mmm, but right now I'm happy just to finally hold you in my arms and kiss you."

She withdrew her finger and dived back in with her tongue, moaning into their kiss as she upped the intensity. Before he knew it she'd snaked her hand down the back of his pants and his eyes went wide as her saliva slicked finger drifted up against his tight rose bud. Jack tensed but she maintained her tight grip while easing to a slow and gentle kiss, calming him until he began to relax and accept what was happening.

Beth gradually started massaging around his hole, her mind racing as she imagined how each and every one of those bumps and ridges would feel against her cock. He gently started pressing himself backwards against it, wanting more but she was becoming a little dry. Did she risk pressing him further? Fuck it, she'd thought, lets go for broke.

She pulled away from his lips as she withdrew her hand and moved it back in front of his face. Extending her finger back to him. Her other hand softly caressed his back, tracing small, gentle comforting circles through the thin material of his top to put him at ease.

"Come on baby, open up, make this nice and wet for me." She said, waiting patiently as he hesitated.

Beth bit her lip and maintained eye contact, her hazel eyes were flecked with a myriad of other colours that radiated out through her irises, mesmerising him as they bored into his, all perfectly framed by her dark wavy hair. The corners of her mouth slowly began twitching upwards into the sexy bewitching smile that she knew would make any man tingle in all the right places.

He gulped. He'd seen her work her magic on others countless times and it had always made him chuckle. How with just one look she could bring a man to his knees and bend him to her will. He'd assumed after knowing her for so long he'd be immune but this was the first time he'd ever been on the receiving end. Her raw sexuality was like hypnosis. How the hell was she doing this to him? His knees started to feel weak. Maybe it's because I've been drinking, he thought as his mouth gradually opened, yes the drink. I'll blame it on the drink.

Beth's grin widened as he trembled slightly before finally complying, unable to resist his sexy dominant friend. She slowly slid her finger back into his mouth and he gently wrapped his lips around it, unable to suppress a little whimpering moan as he lovingly nursed on it.

"Mmm that's it baby, now lap that little tongue of yours around it and give it a nice suck, imagine it's something else. Oooo, yes that's it," she cooed happily as he sucked a little harder in response, "you're doing such a good job."

She pushed a second finger into his mouth, pumping them in and out along his tongue as she fixed him with her steely gaze. Smiling, she spread them apart and felt his tongue eagerly flickering between them and couldn't help wondering if he knew exactly what he was preparing them for. He certainly seemed to have lost all awareness of their surroundings and if she was honest about it the outside world had faded away for her too. Not that she'd really care if anyone walked by and noticed what was happening in this darkened corner. She was way too invested in the moment.

"Mmm, such sweet lips. And you've made my fingers lovely and wet."

She slowly dragged them free, smiling as he gave her fingertips a tiny gentle farewell kiss. The hand on his back moved up to his head and pulled him in for a kiss as the other one drifted back down into his pants. The slickened fingers quickly zeroed in on his tight virgin hole and Jack offered no more resistance as she quickly got back to work. One finger preparing the way before the tip of the other slipped gently inside to explore. Jack groaned and moved his head to her shoulder where he whimpered sweetly as she stroked his hair.

"Mmm that's it baby, just lean forward and open yourself up for me," she whispered into his ear. Moving down she lightly kissed and caressed his neck, each kiss just grazing him with the tip of her tongue. "Yes, that's the way. Bend over a little and rock your hips. Oooo good boy." She kissed his neck again making him moan. "You're opening yourself up so nicely." The tip of her tongue traced its way up to tickle and nibble on his earlobe. "Just let your new girlfriend play with you. I'll be nice and gentle, make sure you feel good."

She quickly looked around before loosening the buckle of his trousers and opening the top button as his eyes widened.

"Don't worry baby, this is as far as we'll go for now," she whispered into his ear, "I just want a little more... wiggle room," she giggled, rotating her finger and pushing it deeper.

Jack moved his leg up to rest a knee on a small coffee table and arched his back slightly as their lips locked together again. Her gently probing finger finally found what it was looking for. A spot deep inside him that sent small but powerful shivers of pleasure radiating out through his body.

Smiling into the kiss Beth slowly but surely increased the pressure. Gradually building up until he was whimpering, bucking and grinding against her. He was so close now. This was it. She trembled in the knowledge that any moment now she was going to make her man cream his pants.

"No wait, please, I can't!" he cried out suddenly, breaking away from her and quickly ducking under her arm. "I'm sorry Beth I... I've just remembered something. I err... I have to be somewhere, I have to umm... I've gotta go," he squeaked as he rapidly scurried away, pulling up and fixing his clothing, shocked and disturbed by how close he was to blowing his load just from Beth's agile probing finger.

He got to the hall doorway before his mind momentarily switched from flight back to Beth. Oh crap what had he done to her? He knew how she felt about him and knew he had feelings for her too. Disturbing and intense feelings. But he'd run off. Abandoning her after she'd found the courage to put herself out there. It must have... well, it must have hurt. He suddenly felt really bad, although definitely not bad enough to go back and have his butt probed again. She must be devastated.

Pausing briefly in the doorway he glanced fearfully over his shoulder, expecting to see her looking bitterly disappointed. Sad, upset and rejected. Maybe even a tear or two. Instead Beth just grinned broadly, licked her lips and winked back at him before he turned tail and fled wide eyed into the night.

Beth was ecstatic, absolutely delighted.

"Yesss." She cried out and spun around before hugging herself. "Yes yes yes. He's going to be mine."

Over the years her feelings for him had grown ever stronger, first viewing him as a good, close friend and then, similar to him, as something more akin to a brother. She'd long ago realised she was deeply in love with him but held off out of respect for Janet. Now she was free to pursue him and everything that happened confirmed she was right about him.

She'd made her opening move and before he'd panicked he'd been putty in her hands. Moaning sweetly and submissively as she kissed and fingered him until he'd been on the verge of cumming. And to cap it off she'd felt him shudder when she mentioned him wearing her panties. Sucking her finger just that little bit more enthusiastically at the idea of her dressing him up. She'd always thought he would make a great boyfriend but the thought of being able to truly bring his feminine side into play every now and again as well? Wow! She leaked into her lacy little undies every time she thought about it.

So she let him go. For now. Knowing he could run but he couldn't hide.

**********

So now here he was sitting in a holiday home on the lake front with Beth and two of their closest friends. They'd booked a week at the picturesque cabin six months ago when it was going to be all three couples staying there. He'd considered cancelling after his breakup but Beth had said... 'Oh, come on. We can still all go together, don't let us all down. It'll still be fun and I'll make sure I take your mind off Janet.'

She'd even convinced him they should both go to the local clinic and get themselves checked out in case they 'got lucky'. Well, he was now pretty damn certain that her version of them 'getting lucky' involved his currently one way exit being swiftly converted into her two way pleasure palace.

**********

Jack loosened his collar again and glanced across at Tom and his girlfriend Alice as they sat smiling and watching on the other side of the cabin's kitchen table, both enjoying the show. He would be enjoying it too if he wasn't the piggy in the middle. They were two of Beth's oldest friends and she'd first met Alice, who was also trans, at a support group. All three of them were still waiting anxiously to hear his answer and see how he would try to dig his way out. He decided to go on the offensive.

"Well I umm... Well so what! I checked it out once after I met you. Everyone does. It doesn't mean I spend all day dreaming about your package. But what it did tell me is that transgender people tend to be smaller. So, my little itty bitty Bethany, despite that wildly sexy and dominant persona you like to project I know you're only packing... a teeny weeny peenie. So just admit it girl. You're all talk and no trouser snake."

"Ouch! He just slammed you there Beth," Alice laughed.

"Maybe," Beth grinned back at her, "but not only has he now admitted to surfing through a lot of trans porn, desperately searching for a nice lady with a big cock. Which is something I can help him with by the way," she added, emphasising her point with widely stretched hands before turning them to point at herself and winking. "But also that he finds my dominance sexy. Don't ya baby." She said, returning her gaze to Jack. "Go on, admit it. Tell everyone that you find me damn sexy. Actually scrap that, you already have." She batted her eyelids at him.

Again he turned red. Damn she was infuriating. Especially when she knew she was right.

"Fine you're a sexy little minx, a cute little sex kitten, with a tiny little kitten cock." He moved his thumb and forefinger close together. "And that's why, no matter how dominant you act in our relationship, you will always be the woman and I will always be the man. Trousers." He said pointing at himself. "Panties." He said pointing at her.

"OK. So now we're getting somewhere. Let's summarise briefly. You think I'm sexy. You've finally realised we're in a relationship. And as soon as my big Beth meets your little Jack you'll accept your place as my sex toy and I'll have you wearing my panties." She stretched and breathed deeply. "Ah, today is a good day."

"You really want me wearing your knickers?"

"No, not really." She grinned, pausing to study his reaction and was delighted to find him looking a tad disappointed. "You have a peachy little bottom whereas I have a nice big bum. My ample curves and ample cock mean you wouldn't really be able to fill out my underwear either front or back. But don't you worry that pretty little head of yours about it. I've already bought you some of your own. Something sweet, silky and sexy just for you. We'll have to shave your legs of course. To get the full effect."

"No way! I'm not shaving my legs."

"Just your butt crack then?" He rolled his eyes but said nothing. Beth smiled. Little by little she was wearing him down. "Good. So it's agreed then. We'll get your back, sack and crack done and then pop you straight into some nice lacy lingerie. It's the minimum I demand from my boyfriends."

"You know I haven't agreed to be your boyfriend yet." Yet? Damn, this was seeming more and more inevitable.

"Yes you have," she giggled, "unless you'd prefer to be my girlfriend of course. You know I'd be totally down with that, don't you?"

"Ugh you're utterly relentless aren't you," he laughed back.

"Yep. And I 'always' get what I want."

"Always?"