A Bad Bet with a Playful T-girl

Jack gave her a quizzical look. "Really? How does that work?"

"Well wouldn't you like to know. And if Beth ever agrees to share you with me you'll find out," she winked and giggled sweetly. "But unfortunately I think she might want to keep you all to herself and I can't blame her. You're a fox baby."

"That's right Alice," Beth interrupted, smacking his ass and giving him a little squeeze, "this is all mine."

"Aww so I can't stick anything in her butt then?" She pouted, before her eyes lit up. "Oooo that still leaves her mouth? Can I slide something between those sweet tender lips of hers? Give her something tasty to suck on?"

Beth rolled her eyes, a small mischievous smile creeping into the corners of her mouth and turned to leave. "I'm walking away from this conversation now Alice, I'm going to go and sit on the sofa next to 'your' boyfriend." She called back as she ambled into the living area to plonk herself down next to Tom.

"You didn't say no," Alice called after her. "So is that a yes or a maybe?" There was no answer and she turned back to Jack with a wide grin. "Well it looks like we might be able to have a little fun with you after all."

"I..." It didn't seem right but... he didn't completely hate the idea. A whole new world of sexual possibilities was opening up to him at the moment and it felt like Beth had left that particular door slightly ajar. He knew he'd always be faithful to Beth but if she was OK with them exploring together at some point then maybe... "Just with you or with Tom as well?"

Her grin expanded. "Ooo would you like that?"

"I... don't think so?"

Alice bit her lip, like Beth before him Jack definitely hadn't said no. She'd drop it for now but maybe one day they could all have a lovely little play together. A horny kinky t-girl like her could always dream right?

"Come and give me a hand in the kitchen, we'll make dinner tonight and let the tops talk. They can cook tomorrow. I've known Jack for years but never met Jackie before so it'll give us girls a chance to get to know each other."

He shook himself back together. "Yeah I'd like that but what do you mean let the top's talk. What makes you think I'm not the top?"

"Yeah, cause you're 'definitely' the top," she smirked.

He opened his mouth to reply and shut it again. He'd somehow got himself into a whole raft of arguments he couldn't possibly win today and the end result was him wearing a dress, having a belly full of cum and having a plug in his arse. It probably wasn't wise to engage in another so he decided to let it go.

As they walked into the kitchen Alice leaned over and whispered into his ear. "Oh and I didn't want to say it in front of the others but you still have some of Beth's cum on your face?"

"What!" he cried out, "Where?" He wiped his face and looked at his clean fingers, he'd had a shower since then and... Oh damn.

"Ha. I knew it. You and Beth had se-ex, You and Beth had se-ex," she sang as he rolled his eyes.

"No. I just... I may have... OK I sucked her off in the shower."

"Nice." She held her hand aloft, maintaining eye contact until he acquiesced, smiled and slapped it.

"Yeah it... it was pretty damn great actually," he giggled girlishly.

"Mmm, I bet it was you lucky thing. I've seen it, remember. I even got to hold it in my hands as I measured it. It's a monster and I can't help but feel a little jealous to be honest."

"Well there's a lot to be jealous of," he giggled, relaxing and feeling more like Jackie by the minute. "But I've been meaning to ask you something for ages. You two have always been really close but never hooked up. Did you ever consider going with Beth?"

"Ha, no chance. You've seen the way she goes through boy and girls. I know it would have been great while it lasted but I value our friendship 'waaay' too much to risk damaging it for a brief fling." She looked into Jack's worried face. "Shit! Sorry, I didn't mean it to come out like that. It'll be completely different between you two. The reason she goes through so many people is that she's always been searching for someone to match up to you and in her eyes no one else does. Certainly not me. You and Beth are simply meant to be together."

Alice paused in thought for a moment. "The only doubt she has in all this is if you decide you can't cope and break her heart. I think it's one of the reasons she's been so desperate to feminize you this week. She wanted to prove to herself that she was right about you all along but also wanted to force you into a corner. That way you'd either show her you were ready to fully commit or run for the hills. She didn't want to get her hopes up only to have them dashed again. She's not actually as confident as she acts."

She grinned. "And besides, whenever we talked through her fantasies about pinning you down and filling you up we both agreed you'd look frigging awesome riding her in a frock."

"Yeah thanks Alice, that's good to know. Not the creepy frock thing but the other parts. So you think she's definitely in for the long haul?"

"Are you fucking kidding me? She's been into you for years. Figuratively at least. It's about time you let her get into you 'physically' as well you naughty little cocktease."

"Cocktease! I'm not a cocktease. Since when have I been a cocktease?"

"Oh really! Cut the bullshit Jackie. We both know you've been flirting with her for years, tempting her with that sweet little ass of yours before running back to Janet to leave her blue balled. Well you've had your fun and now she's going to have hers. Tonight you're going to go from shameless cocktease to a well fucked cocksleave. She's going to bend you over, shove that big-ol-dick deep into your pretty little bottom and fuck your brains out. And it's going to be epic."

She bit her lip as her eyes drank him in, imagining the show. "Mmm, I only wish I could be there to see it. But... I suppose I'll just have to make do with putting my ear to the wall so I can hear you moaning away as she pounds your tight little butthole. Because you know I'm totally going to do that right? That I'll be listening at the door stroking myself while she breaks you in, makes you her bitch, makes you squeal."

She visibly shuddered at the thought before getting herself back under control. Alice smiled, gave his bottom a friendly little pat and winked before walking over to dice some vegetables. Jack stood open mouthed as she hummed happily while working away at the chopping board.

"Can you pass the carrots," she asked innocently.

**********

Dinner was surprisingly normal. A group of good friends eating, drinking and reminiscing old times and their shared histories. Other than a hand on a knee and an occasional peck on the lips nothing of a remotely sexual nature took place.

Once they'd eaten they all sat down to watch a film together under dimmed lights, still talking and laughing. It was like their first double date and each couple sat on one of the two mini sofas with Jack snuggling into Beth while Tom cuddled Alice. About half way through the movie Beth began to nuzzle Jacks ear and he angled his head away to grant her better access, making light encouraging noises as she started kissing his neck. Her hand wandered down his body, caressing his new d-cup forms as her hardening cock began to press against him.

As the wine they'd drunk started to lower their inhibitions he shifted around to meet her lips as they began a slow but heavy make out session, melting into each other's arms. Risking a glance to his left he noticed Tom and Alice doing the same only Alice had unzipped his pants and taken him in her hand, slowly jerking him in time with their kisses. A pang of jealousy coursed through him. If she got to play with a nice hard cock why couldn't he?

Knowing he should take Beth back to the privacy of their own room but unwilling to break the kiss he risked another glance to confirm that no one was watching. OK. He'd take it just a little bit further, he just needed to feel it under her dress. Just a quick touch that's all. No one would see, no one would ever know.

Beth felt the hand on her knee begin to move upwards to creep along her inner thigh and didn't need to think twice before widening her legs. Pulling the shaft from her panties he slowly massaged its length, teasing her as she hardened in his hands. Jack swooned into her mouth, once again he seemed to have forgotten how big she was, how hotly it throbbed within his grasp when he held it and how strongly it called to him.

Opening his eyes again to glance down he quickly noticed the travesty that was unfolding below. A wet patch was forming in the fabric of her dress. That was so wrong. That was his precious precum. He was the one coxing it from her and the dress couldn't have it. He jealously pushed the fabric clear to bring the object of his desire into the open, exposing her and marvelling at the glistening droplets of precum sparkling in the soft lamp light, his droplets, his lovers gift.

He needed to taste her. Jack gave her another quick peck for luck and moved rapidly down, his open lips stopping suddenly, hovering just millimetres from their target. Shit! What was he thinking? He couldn't do that here, they weren't alone.

Looking up he saw Alice staring back at him with a mischievous twinkle in her eyes, one hand still working Tom while the other worked away between her own thighs. 'Suck it,' she mouthed at him, 'Suck her cock'.

Maintaining eye contact with Alice and seemingly unable to stop himself he obeyed her command, opening wide and lowering himself onto her. Alice's grin spread out across her face as his lips closed around Beth's thick spongy head. "Good girl," she cooed softly as he began bobbing up and down. Disturbed and aroused in equal measure he couldn't tear his eyes away from Alice as he moaned and lowered himself to take more and more of Beth's length into his mouth.

"Mmm that's so nice," he heard Beth moan. "Keep it up baby."

The hairs on the back of his neck rose up the sound of her voice, was she fully aware of what was going on here? He sucked away as Beth rubbed his head affectionately and Alice turned away to whisper into Tom's ear.

"Look Tom, Jackie is putting on a little show for us." She giggled, turning back to Jack as Tom lowered his head to look too, both watching him intently and talking in hushed barely audible tones. "Mmm and just look at her go. She's such a good little cock sucker isn't she?"

"Uh-huh," he whispered back, "the girl's a natural. And as for Beth, well... after hearing all the rumours I've always wanted to see her in action," he grinned.

"Hell yeah! If we're lucky we might actually get to see Beth breaking her in. Can you imagine that? Seeing Jackie taking that huge thing in her ass." She smiled as Jack trembled at her words, sucking that little bit harder. "Ooo I think Jackie really likes the idea of that," she added gleefully. "I think Jackie's a dirty little girl. I think she wants us to watch."

No! No I don't! Jack's feeble denial echoed around his skull even as the thought of it made him shudder, twitch and leak into his panties. He shifted into a slightly better position so he could take more in. The fact that it gave his observers a much better view was surely just a coincidence. Because that certainly wasn't something he was into.

This was so wrong, so dirty, and yet... "Mmmm," he moaned around her as he ground himself into the sofa... so fucking good. Why was this turning him on so much? Why was he getting off on this?

He slowly pulled off Beth's cock, staring at them the whole way up. Smiling, he lapped away at her slit, before kissing and sucking on her very tip. 'Jackie' gave them a salacious wink and dove back down to take in as much as possible. A loud moan of pleasure from both him and Beth echoing around the room as she bucked upwards into his mouth.

Oh shit! Why the hell was 'she' so into this! Because it was 'her' doing it, not him, not Jack. Despite all the lewd banter Jack was actually quite reserved but it seemed like Jackie was a wild and shameless hussy at heart who was loving all the attention. There were a lot of new and disturbing things he was learning about himself and his alter ego today.

He was wondering how far Jackie was prepared to go with this when a rush of cooler air on his backside caused his eyes to shoot open. Uh-oh. Beth had just flipped up the back of his dress. He paused for a moment, staring at the grinning couple on the other sofa before Beth's hand began to gently but persistently push on his head to get him moving again.

Jack began to relax again, returning to gently sucking as she played with his exposed butt cheeks. He felt her hand sliding over his pantie clad ass, gliding across the smooth flesh, stroking, squeezing and... 'Slap'. "Mmmpphhh." He moaned onto her cock and took it deeper as she spanked him.

"Oh yessss that's it, give her a good spanking," Alice moaned huskily under her breath.

'Slap,' "Mmmmphhh," 'Slap,' "Mmmph, mmm, mmmm."

After the last playful spank Beth's hand drifted down to his inner thigh and pulled upwards with just enough strength to make him realise what she wanted. Jack moved up onto his hands and knees, arching his back and spreading his legs wider to give her better access.

She gave him another quick spank followed by a little loving squeeze and ran her hand lightly over his creamy orbs.

"That's it baby," Beth cooed as her fingers drifted along his crack. "Open yourself up so I can play with this cute little bottom while you suck my big fat juicy cock."

Beth tapped the end of the toy still buried deep within him as Jack moaned and wiggled his tongue into her slit. He continued to worship her cock and was rewarded with an extra spurt of her pre-cum, the taste overwhelming the last of his inhibitions. Fuck it this was happening and he was just going to embrace it. He was going to let Beth take his anal virginity while her friends watched.

Beth gripped the flared end of the butt plug and rotated it inside him, the heavy ball at its centre helping to stimulate him each time it rolled into his prostate. He whined and gyrated against her, rocking his hips to encourage her and show her he was ready.

Smiling, she began to push and pull the plug in and out of him, the thickest part of it stretching and relaxing his sphincter over and over again as she prepared him for the inevitable. She suddenly ramped up the intensity by angling the plug into his bottom button and pressing down hard. Jack let her slip from his mouth and moaned loudly into the room.

"Mmm you really like that don't you baby?" She cooed playfully, "Come on Jackie, I think we need to go somewhere a bit more private so I can pull this out and put something else up there instead. Something a lot bigger and a lot more fun. Would my little girl like that?"

He looked across to Alice and saw her face fall. "Aww!" She pouted and turned to whisper to Tom, "that's such a shame, I had really had my heart set on seeing the full show. Oh well." She sighed despondently before turning back to Jack, a warm wistful smile creeping across her face as she thought of what could have been. 'Thanks anyway sweetie' she mouthed at him, winked and blew him a little kiss.

He held Beth's cock in his hand, watching his watchers and considering his options before coming to a decision he never thought he'd ever make.

"Well baby?" Beth asked with concern entering her voice. His delay in answering had begun to feed into her own deep seated and well hidden doubts and anxieties. "Would... would you like that?" She had read this right hadn't she? He was still going to be hers wasn't he? He surely wouldn't back out now!

"No!" He kept looking straight at Alice. "I want you to fuck me right here on the living room floor."

Alice's eyes lit up as she returned to enthusiastically rubbing herself through her clothing, unable to stop herself from loudly moaning, "Oh yessss," to finally draw Beth's attention.

"Wha-what?" Beth looked over and noticed her voyeuristic friends for the first time and then looked back to Jack. "I... Oooooh," Jack had taken her back in his mouth to give her a long deep suck. "Jack I... Ahh... I don't... Ooooh... I don't know about thiiisss."

He pulled off with an 'pop!' and rose up to look directly into her eyes. "Neither do I, but tell me why you dressed me up like this tonight."

"What? I... I just thought it would be fun is all..." she mumbled unconvincingly.

"That's not the full story though is it Beth." He reached up to brush away a lock of hair that had slipped down to obscure her vision, forcing her to maintain eye contact. "Be honest with me. We both know you would've accepted me as either a boyfriend or a girlfriend so why did you go all out to feminize me today?"

"I... fine I needed to know you'd fully commit to me, OK!" She blurted out before dropping to a quieter, more vulnerable tone.

"I felt if you were prepared to be seen as my girlfriend around the three of us in private then maybe you'd be prepared to be seen openly as my boyfriend in public." She sighed. "It's really stupid I know but I needed to be absolutely sure about everything before I allowed myself to believe. And... Well I also wanted to show my friends that I was right about you all along. That you'd do anything for me, show off a little bit." She shrugged, her trademark cute mischievous smile returning even though her cheeks still flushed red. "Sorry, I'm a bit of a dom in case you hadn't noticed."

"Oh I've noticed baby! I know you're my sexy little Dom," he kissed her lips, "and it excites me so much." He turned to Alice. "Do you have any lube?"

"Yes of course!" She quickly took some from her bag and handed it over to him with a trembling hand. "Here you go Jackie. It's strawberry, quite tasty actually, I think you'll like it." She returned to her seat, her elbows on her knees and her chin resting in her hands in disturbingly rapt attention.

"Thanks babe," he replied, winking and putting on his best feminine voice, "gotta get my big girl ready for me." He popped the cap and began to massage it into her straining throbbing member. Once it was suitably coated he leant forward and gave the tip a little kiss. "Oooo Alice is right. It is nice and tasty."

Standing up Jack sauntered into the centre of the room swaying his hips seductively. Looking back he licked his red painted lips and reached under the dress to lower the waistband of the panties until he could shimmy them down his long smooth stocking clad legs to the floor. Biting his lip provocatively he stepped out with one foot and knelt down, the lacy white thong hanging off one ankle as he flipped up the back of the dress and crouched. Hands, elbows and knees on the ground. He looked back to see his woman slowly stroking her lube slicked cock with eyes full of lust and lechery.

"Well Beth. You wanted me to commit openly to you and I can't commit any more openly than this. So I'm begging you to take me right here. I need you to sink that big beautiful cock deep inside me and claim me as your own. I'll be your girlfriend, your boyfriend, your everything and I don't give a fuck who sees." He arched his back, presenting himself to her like a bitch in heat. "Please Beth, pleeease. I need your cum inside me."

With a low feral growl she rose to her feet, pulled her dress over her head and threw it violently aside. Jack looked on in awe as she stood in her deep red lingerie, a fire burning in her eyes, every bit the devilish seductress compared to the virginal white of her soon to be conquered lover.

A sultry smile spread over her face as she sashayed over to him, her cock bobbing away enthusiastically. With every step Beth's confidence flowed back as the last of her doubts about their future together crumbled away. Of course he'll want to be seen with me. I'm Bethany and I'm a goddess, she reminded herself, a dominant force of nature who's finally going to claim my one true love. It might not be quite the way she'd always planned it but maybe it was better this way. Maybe a goddess like her deserved an audience.