A Bad Bet with a Playful T-girl

Bending down she took the end of the plug and rotated it deep inside him one last time. Jack tensed as she began slowly easing it out, the bulb's tapered rear end stretching him wide until with a long guttural moan it passed its widest point and slipped free. He dropped his head to the floor as Beth inspected him. Gently prising him open she marvelled as his once tight hole winked and gaped invitingly. She grinned and squeezed his soft cheeks, the thick neck of the plug had performed its job admirably.

"Good girl," she praised, as she slowly inserted a couple of fingers. "Mmm that's opened you up so nicely." Beth twisted them around as she explored and tested his depths for a little longer, adding a bit more lube as she assessed him. "Yes, that's perfect, you're all ready for me my dear." She tapped his prostate a couple of times to make him squirm deliciously before she withdrew them.

Jack felt her digits leave and remained crouched and tense, his hole flexing in its brief respite. Her thick cock landed heavily in his cleft as she moved it back and forth, using her hands to squeeze his pillowy cheeks together. Yet again it felt huge in contact with his skin and he wondered if its size would ever stop surprising him. Shit what if she's too big! A wave of panic flowed through him along with a sudden urge to run that he struggled to suppress.

Beth pulled back and lined herself up, squirting on another generous layer of lube. It looked like overkill but she knew from experience that with an anal virgin you could never have too much. She tapped it once more against his hole. Knocking on the door and grinning as it opened up slightly before her, seemingly anxious to welcome in her thick spongy head.

"Are you ready for me baby?"

"Yes! I need you inside me." Another part of him cried out. The part that had belonged to this amazing woman for years and would never deny her, never run.

"Mmm such an eager girl," she cooed happily and began to push.

He felt the pressure increase but she had prepared him well and despite his worries he breathed deeply and held his ground.

"Don't fight it baby, just relax and let me ease into you," Beth cooed softly. "Let your girlfriend's big dominant shecock slide into its rightful home," she added playfully. He was still too tense but she avoided pushing any harder, instead waiting patiently for him to open up, unwilling to force it.

"Good girl. You're doing so well honey and I'm so proud of you."

He was still whimpering and trembling but she could feel him loosening up. Her well lubed head was starting to inch forwards, easing him apart as the ridge of her glans moved inexorably towards the event horizon.

"That's it baby, I'm almost there sweetie, almost there. Annnnd... Oh yesss there we go!" She cried out as he eventually gave way and she slipped inside. "Oh yes, oh yes, oh that feels incredible, Oh wow it's so good to finally be inside you honey, so, so good."

"Oh fuuccck! Oh shit, it's so big Beth, you feel so big I... Ugh... I feel so fulllll."

Jack lowered his head to the floor as he felt himself clenching and unclenching around her. Beth was holding his hips tight, enjoying the sensations as he pulsed around her, his hungry ass desperately trying to milk her. She waited until his convulsions began to ease, knowing first hand how painful it could be if you rushed.

She stroked his back, a small gesture to distract and comfort him as he got used to her girth. Beth knew it was working when she felt him rotating his hips experimentally, it could have simply been him trying to get more comfy but the soft girlish mewing of her partner suggested otherwise.

"You're doing so well Jackie and those wonderful little movements you're making feel incredible. Just oh so good." She leant down and kissed his shoulder. "Such a good girl." She kissed him again. "Are you ready for me to continue?"

He'd also felt the contractions in his ass fading. The whole experience had been so Intense that he couldn't quite work out whether it was painful or pleasurable but his mind was beginning to shift to the latter. He moved his hips around again, this time enough to alter her depth and groaned as he felt it shift delightfully within him.

"Oh fuck, Oh wow, I... I think I like it?

"Yeah? Does my dirty little girl like taking mommy's thick cock in her bum-bum," she giggled, "is she a bit of a butt slut?"

"Mhmm," he moaned, rocking slightly and wondering absent mindedly why he couldn't feel her balls resting on him, it must be the sheer volume inside him that had overwhelmed all other stimuli, yeah that's it. "Oh Beth I feel so full, I... I can't believe I just took you all the way to the base like that." He heard her try and fail to suppress a gentle giggle. "W-what is it?"

"Oh my beautiful sweet innocent girl," she cooed, lowering herself onto his back to speak directly into his ear, her breath tickling his neck. "You've only taken the first few inches you silly little thing," she chuckled and playfully bopped the end of his nose with her finger, "you still have a long way to go."

Jack opened and shut his mouth, a few half formed and unrecognisable words falling out.

"Don't worry about it sweetie, everyone thinks they've taken more than they have the first time they're breached but the good news is... You've still got another four and a half inches of throbbing cockmeat to go. Now prepare yourself baby because I'm about to start feeding you the rest."

Beth increased the pressure as he gritted his teeth. She went slowly, pushing just a little deeper each time and rotating her hips to stretch him out, never more than he could take but still at the very edge of his tolerance. She bit her lip and fought herself for control, preventing her horny inner dom from taking over and pounding him like a sex toy. At some point she'd be able to fully unleash the sexy dominant mistress that resided within, but only occasionally and only when he was ready. Only when she knew he was experienced enough to love it.

Jack put his head to the ground and arched his back, content to put his faith in his skilled partner as he alternated between hisses of pain and gasps of pleasure. As the pain slowly ebbed away he began moaning incoherently, abandoning his higher brain functions and surrendering himself to the moment as she fed more and more of herself into him.

One small residual part of him remained in the wider world and it became aware of other voices in the background. On auto pilot he turned towards the source but with his mind half lost he found himself struggling to focus on the faces or decode any meaning of the words.

"Oh yeah she loves it." somebody said, a man maybe. "I've never seen anyone take a dick that big outside of porn. I'm not sure I could."

His eyes were beginning to focus when Beth's cock bore down yet again on his prostate and the details slipped away. Arching his back he released another high pitched girly moan.

"Oh and she moans so sweetly," Alice gushed. "Our little Jackie will never be the same after this you can see it in her eyes. Every thrust is breaking her just that little bit further, moulding her body and mind to that beautiful big dick. Aww, it's such a wonderful thing to see. And you just know that by the time Beth floods that cute little bottom with her lovely warm cummies Jackie will truly belong to her. She's such a lucky girl."

Alice bit her lip and finally noticed Jack staring at her through lidded, fluttering eyes. "Oooo she's looking. Smile for the camera sweetie! I'm recording it for you."

Jack just about managed to zone in on an image of her waving happily and pointing a phone at him before another deep, powerful thrust into his bowels made his eyes roll. "Oh yesss," he moaned, shifting his head forward again. He didn't know what was happening to his side and he was too far gone to care. All that mattered to Jack was that the woman he loved was feeding an endless supply of dick into him and it was starting to feel sooo good.

Beth smiled as she felt his tight tunnel begin to relax and upped the pace, his strained groans had changed into sweetly encouraging moans. She grinned broadly. She might not be fully inside him yet but she was really starting to work his prostate. Not everyone could cum hands free, especially on that first painful time but she was a skilled and patient lover. She'd make him. Her earlier explorations had found all his weak spots, she knew exactly when, where and how hard to push and she was going to exploit it ruthlessly. By the time she was done with him he'd be addicted to her cock, she'd only have to point at the floor to get him sinking to his knees.

But that was for later. First he had to take her full length. Gripping his hips she slowed the pace slightly but upped the pressure as she sought to force home her final two inches. She felt him tense and shake as she speared six inches into him, held and withdrew.

This time, she thought, and drove forward only to be denied by an internal sphincter. With next few thrusts she knocked at that internal door, each time it widened, rocking on its hinges as her cock demanded access. She felt it giving way and drew almost all the way out, flexing her fingers as she altered her grip in preparation for her final all out assault. This time nothing would stop her. He would take it all.

"Almost there baby, not everyone can take all this dick but I know you can. I hope you're ready cause I'm about to go balls deep. Annnnd..." she pushed on, long and slow but utterly relentless as he shook beneath her, "...oooooh, yeah there we go baby!" she cried as the final barrier was breached and she slid fully inside. "Oooooh yessss allll the way in there, Wooohooo, yeah can you feel that!"

"Yesssss, oh fuck yes and it feels incredible. Oh that's so good," he moaned, rotating his hips and pushing himself back up onto all fours. Now he could feel them, those big heavy balls knocking against his own to tell him they owned him, reminding him of how much she could cum, of how much she'd fill him up when she finally bred him. And he needed it more than anything. He needed that cum.

"Mmm, that's it baby," she cooed as he began to rock backwards and forwards, "fuck yourself on my big fat cock."

He began moving faster and faster and moaning louder and louder.

"That's it baby." 'Slap!' "Rock those hips." 'Slap!' "Show me how much you want it."

"Yess, fuck me Beth, fuck me hard."

She gripped his hips and pushed harder, giving him all he wanted but still holding something back, unwilling to hurt her man.

"Ugh, I'm gonna cum soon Beth, fuck you're gonna make me cum."

No! Not like this. It was too impersonal. She needed to see his face when they came. To look deep into each other's eyes so they could burn the image into their very souls as their body's sang.

She pulled out, grabbing a cushion from the sofa as she flipped him onto his back and placed it under his hips. Jack opened his mouth to complain but returned to moaning happily as she speared back into him before he had a chance, his eyes rolling.

"Look at me baby, look into my eyes as I claim you." Again he struggled to focus but unlike last time once he did he locked on with intensity. The deep, warm hazel eyes of his best friend, his lover, his whole world, holding him like no other. He didn't think he could never tear himself away from them again. "Are you going to cum for me my love? I'm so close and I want you to come with me. I love you and I want you to cum when I fill you up." Leaning down she kissed his lips, slipping her tongue into his mouth as he wrapped his arms and legs around her.

She continued the kiss, her tongue dominating his mouth as she dominated his body, angling up into his prostate she felt his grip tighten and he broke away as he spasmed beneath her.

"Cum for me baby," she cried as she rammed his pleasure centre, "cum for your girlfriend, Show me how much you love meeeee."

Her own dam broke first, a powerful tidal wave of girlcum flooding into his bowels as she sent rope after rope of her seed deeper into him than anything or anybody had ever reached before.

"Oh fuck Jack, I love youuuuu," she screamed.

Jack felt the vibrations massaging his prostate and climaxed himself, unlike Beth he couldn't talk as he was too far gone, all he could do was tremble as the cum flowed from him, the same but different. While Beth came in a torrent his was long and slow, pulsing out each time she flexed within him. Beth moved back down to reclaim his lips and kissed him hard, her hips returned to life, pumping in and out of him as each thrust milked his prostate.

The mind numbing intensity slowly ebbed as their flows gradually petered out, their kiss easing from hungry and wild to slow and intimate. Beth finally ended it, pushing up on her elbows and smiling into his eyes.

"I love you baby," she cooed.

"I know Beth. I think I've always known... and I love just as much."

They remained like that for a little longer, smiling happily and gazing into each other's eyes until a high pitched excited voice dragged them back into the real world.

"Awww you guys are sooo cute!!!"

They both turned to look at the clearly ecstatic Alice, happily bouncing up and down in excitement by the sofa. Oh shit! They'd totally forgotten about their audience. With the release of all those years of pent up sexual tension the madness of what the had just done was finally beginning to dawn on them. Oh no... And they just knew she'd be going on and on about this forever.

Alice rushed over with her usual complete and utter disregard for social norms and personal boundaries to wrap them both in her arms.

"Aww man I love you guys. I'm so happy you got together and that I was here to share it with you. Oooooh I'm just so pumped!" She squealed, kissing them both on the cheek with an overly elaborate 'Mwah', 'Mwah'.

Beth and Jack looked at each other around the intruding Alice and smiled before both hugging her back and breaking into laughter. Eventually the weird three way hug ended and they rolled over to collapse on the floor. Slowly recovering as Alice bounced away to the kitchen to make them all some margaritas. Apparently she also had some great home movie to show them too but thought it might have to wait till tomorrow.

Still giggling and lying prone on the floor Jack and Beth looked over at each other before reaching out to lock their fingers together. It was going to be a fun week...