Over an Ex and Under a T-Girl

She finally pulled back to get him ready, quickly slipping in first one and then two fingers before twisting and thrusting them into him. The lewd sucking and squelching noises drifting across the kitchen. She didn't give him long, she was on fire, burning with a desperate need to claim her new boyfriend's ass.

"And you're definitely sure about this? You've just cum so I don't mind if you don't want to go again so soon," Gwen offered while lining herself up and starting to push.

"Yeah, just keep going I waaaaooooohhhsshhhhiiitttttt!" He cried as the slick head suddenly breached his ring and popped inside.

"Oh fuck yeah!" She cried out, "Oh it feels so good to finally be back inside you. I can't even begin to tell you how much my dick's been missing this tight little hole of yours." She bit her lip and ran her hands down his back feeling how tense he was. "Oh shit, sorry. You said you wanted me and I was just so horny I couldn't wait. Was I a little too fast?"

"That ugh, that depends." He rasped. "When you say were you a little too fast, are you trying to tell me you've already cum? Because if so then yeah, that was a little too fast for me. If you meant the entry, then yeah a bit but it feels amazing and I couldn't wait either."

He felt her leaning down, her lips on his skin as she lightly kissed his neck while her hands caressed him. The head of her cock twitched and pulsed within him, moving ever so slightly forwards and backwards. He pressed his stomach down onto the table and gripped the edges as he slowly began moving back and forth. Moaning softly as he did and only taking around a 1/4 of an inch in and out.

Gwen stood back up, sliding her hands down his body. Watching him rock himself on her and awaiting the inevitable. Waiting for him to give himself to her. Waiting for him to ask her to fuck him.

"Gwen I'm ready so umm, can you work some more into me?"

"Are you sure baby?" She teased. "Are you sure you want this big fat cock deep inside of you?"

"Yesss. Please Gwen."

"And you'll give yourself to me? Let me take you anyway I want?"

"Oh fuck yes, take me Gwen, use me, fill me, please."

"Whatever you say sweetheart."

Gwen's hands trembled with anticipation as she changed her grip, moving her left hand to his shoulder and her right to his hip. The first time they had sex he had rode her and the second he had taken her so both times he was in charge, in control. This was different. She had him bent over and spread wide open, arching his back and mewing like a little kitten. Her cock was already inside him, ready and waiting to breed him. This time she was in full control and that was the way she wanted it. It was time for his new top to give him a proper fucking.

She began pushing into him, determined to sink herself balls deep in one long slow steady drive and watched him shudder beneath her. "There you go baby," she grunted, "you can always rely on me to give you what you need." She bit her lip as inch after tortuous inch slid in, slow, steady and relentless as his eyes rolled and his whole body shook. "Almost there sweetie, almost there, annnnd... we're... allllll the way in," she groaned and threw her head back as her balls finally made contact with him. "Oh yesss, there we go."

She bent down and lightly bit his shoulder while she ground herself into him, rotating her hips to make sure he felt her full length.

"Mmm you like that baby?" She whispered into her ear. "You've got my full dick inside that tight little ass of yours now." She pushed again, forcing an extra couple of millimetres in to emphasise the point. "Oh and that question you asked earlier, about whether I'd already blown my load. Well you don't have to worry that pretty little head of yours about that, honey. Because when I do cum, I'm gonna cum so hard and so deep you'll be able to taste it"

She licked the side of his face all the way up to his ear before standing back up, giving him a quick spank and gripping him tightly.

"It's time for your new woman to properly break you in, baby."

She slowly withdrew until the ridge of her head just began to stretch his hole before pushing all the way back in. Long slow deliberate strokes to open him up and get him used to her girth. Nice and easy, the calm before the storm. Every time she pulled out Jeff seemed to be fighting against her, his tight tunnel gripping onto her and seemingly reluctant to let her leave but when she reversed course it seemed to almost suck her back in.

She grinned as she heard him starting to moan and began increasing the tempo. He'd already cum so she allowed herself to be a little selfish, concentrating purely on her own wants and needs. The clapping sound as her hips meet his firm round bottom began to ring out around the kitchen, accompanied by the slow sucking sound of his well oiled ass fighting to keep her in each time she withdrew. She ground herself into him as she bottomed out and became lost in the sensations as she built a steady rhythm.

"Oh fuck!" He cried out, breaking her from her reverie. "Fuck that feels so good."

Gwen snapped back to reality with a sudden concern but her face quickly broke into a smile. She had been so lost in her own desires that for a moment she thought she might have actually been hurting him. But no. He fucking well loved it and it was time to make him love it even more.

She bit her lip and changed her angle to drive down into his prostate rubbing along it and making him shudder. Her eyelids fluttered as she felt him tremble all around her length, massaging her dick with the spasming muscles of his tunnel.

"Oh fuck Gwen keep doing that, oh shit, we only did this yesterday now could... how could I have forgotten... how good it feels to have you inside me."

"Yeah you like that baby? You like it when I fuck you nice and slow." She pushed in deep and he moaned in appreciation. "Yeah you do. You want it so badly and I want to give to you just as much. Do you like it when I press here?"

She moved up onto her toes and pushed her cock directly down onto his prostate making him writhe underneath her, his own toes curling up as the waves spread through him and a few more drops of his pre-cum fell to the floor.

"Yeah you love it Jeff. It's so much better this way isn't it baby."

Again she forced herself into his prostate.

"Ohhh yesss, fuck me Gwen, don't ever stop."

A massive toothy grin split her face as she thrust into him. She had no intention of ever stopping. She would be pounding this tight little butt of his forever if she had her way. Gwen pulled him into a standing position, leaning him forwards to support himself with his hands as she pumped in and out with renewed vigour. It gave her a far better angle to get him going and his tightly flexing hole was clamping down on her more and more as she milked him. It dribbled down to form a long viscous strand that spun back and forth as she worked him harder. She leant down onto him, her breasts pressing into his back as she angled his head towards her.

"Kiss me." She demanded, pressing her lips to his and slipping her tongue into his mouth as his hand moved to cup her neck and hold her in place.

As they moaned into the kiss she reached between his legs for his cock and as soon as she made contact it twitched and flexed wildly, pulling up and away from her fingers. Fuck he's ready to blow again she thought and quickly withdrew her hand. Smiling into the kiss she began attacking him with far greater passion. Hands free. She was going to make him cum without anything touching his dick to reinforce in his mind just how good it felt to be dominated by a sweet, kind and well hung t-girl.

Knowing what she was doing to him was making her harder than ever and she felt the tingling in her balls as her own army of little swimmers mustered for their assault on his back gates. She was close but wanted him to cum first, she wanted to feel him clamp down on her, to feel Jeff milk her as she was milking him.

"I'm almost there baby," she cooed, breaking the kiss and standing back up. "Are you close too? Are you going to cum for me baby."

"Ugh, ugh, ugh," he grunted in response.

His mind was swimming. Unable to form rational thoughts let alone talk as his cock bounced and dripped with every drive of her cock. His prostate was under constant pressure and the feeling was permeating his entire body, shaking him to the core. It was coming, the wave was cresting, a tsunami was about to hit.

"Oh fuck Gwen I love you," he cried out as the wave finally broke and his cock began to flow. "Ugh, ugh oooooooh fuck, yesssssss oooooooh yessssss."

It was longer and deeper than anything he had experienced before as the cum didn't so much explode out of his dick as ooze and dribble. Every time she drove into him more and more cum poured out of him, forced out of his cock by Gwen's thick hard rod squashing into a magic place he hadn't even known existed.

"Ooooooooh," he groaned, collapsing back down onto the table, unable to fathom how he had been cumming for so long. "Ooooooh god."

Gwen was clenching her teeth, trembling and fighting back her own orgasm as he gripped onto her like a vice. His tight loving tunnel was contracted rhythmically all along her cock and sending ripples of pleasure pulsing outwards to travel through her entire body. Finally she stopped fighting and just let it go. Succumbing to her own need for release.

"Oh yessss," she shouted, "Oh yes, oh yes, oh yesssss. Ugggghhhhhhh."

She drove herself as deep as possible and held herself there, her balls contracting as she blasted her load deep inside him. Her legs shook and buckled beneath her as she held on tight, relying on him to hold her up and keep her from collapsing.

"Oh-oh-oh, oh wow, oh my god, oh wow." She repeated over and over again as shot after shot entered his bowels. "Oh wow."

She half fell half laid down upon him, wrapping her arms around her boyfriend. Panting and clinging on as the last of her seed seeped into her man.

They stayed like that for several minutes, smiling and recovering, unable to move and simply enjoying the contact and closeness. As time passed and her energy started to return Gwen began planting small kisses on his back. She gave him one last big squeeze and stood, stretching and giggling as she slipped out of him and a little stream of cum dribbled out to join the messy pool of oils and bodily fluids already on the floor.

"Oops, that's going to take a lot of cleaning up," she giggled, "but totally worth it. Here use this to umm, well you know." She tore off some kitchen roll and pressed it into his crack to plug the leak.

"Oh, umm yeah, OK thanks," he mumbled, standing back up and holding it in place.

He turned around looking a little embarrassed but she just beamed back and threw her arms around him. Kissing him on the lips and holding him tight. After briefly considering his options he clenched his butt cheeks to hold the kitchen roll in place and cuddled her back. One hand quickly running down to fondle and hold her bum as she chuckled at his newly acquired tissue paper tail. Her own little sex bunny.

"So... You love me do you?" She lightly taunted and giggled as she felt him stiffen in her arms.

"Umm well Gwen... You see I..."

"Oh don't worry I'm only teasing," she said, pulling back to look into his eyes. "I know it was only said in the heat of the moment. And damn was there some heat in that moment." She grinned with smouldering eyes. "That doesn't mean I didn't enjoy hearing it though."

"Ah well, about that Gwen, I..." she raised an eyebrow and smiled, waiting for him to finish the sentence. Shit! How do I finish that sentence? "I really, really like you Gwen but umm..." Crap! He still didn't know how to finish it.

"But you need more time to see how this develops and get to know me better?" She said, taking pity on him and completing it for him. "That it's not love yet but you know there's something real and special between us? Something waiting to grow?" She moved to whisper into his ear. "And when I say something real and special between us waiting to grow. You know I'm not just talking about my cock, right?" she smirked.

"Ha, Yes exactly," he chuckled, grateful for her intervention and moved to rest his forehead against hers. "Thanks Gwen you're amazing. Things like that Gwen, that's why I... I really like you." Shit, he thought I was about to say 'love you' again.

"Anytime Jeff, anytime."

As he pulled back she studied his eyes closely. There was one more thing she really needed to know and she couldn't wait anymore, the suspense killing her. She took a deep breath and began the conversation that could very well make or break their burgeoning relationship.

"So... you looked like you really enjoyed that Jeff and you seemed to enjoy it both ways. In fact if anything it looked like you came harder the second time around. Are you going to be OK with us having sex like that? With me topping you?"

"Umm well yeah of course. I didn't know if I'd like it but it actually felt really good and I'd definitely do it again so I guess I'm... flexible? Is that the term?"

"You could also use verse or switch but yeah, flexible definitely covers it. Personally I'm a bit more narrow in that I very much prefer being the main top but for you I'd be prepared to change that. I'd be prepared to meet you in the middle. So if we are going to be together would you want to keep it more even? A bit more 50/50?"

"Well yes and no, umm... Oh crap." He said going red.

"Hey," she rubbed his arm and gave him a gentle and inquisitive look. "Say what you need to say. It's far better we talk about this now so we know what we're looking for here. I guarantee whatever you say will remain between us."

Her calm exterior was in stark contrast to the raging storm inside her. She could be wrong but she was convinced he'd enjoyed it much more and cum far harder when she was taking him. The same short sentence was on repeat in her mind, echoing around and around in her head.

-'Please say you want me to be the main top, Please say you want me to be the main top, Please say you want me to be the main top.'-

For him she would be prepared to switch it up a bit, she'd flex. Gwen would put out however and whenever he wanted and she knew she'd enjoy it simply because she would be making him happy but... if he did want to take the more submissive role... She crossed her fingers.

"Well I'd still want to be able to take you whenever I wanted to Gwen but umm... Ah this is difficult for a guy to say... OK, so when I was inside you it felt really good. You're so warm and tight and I got to rub my hands all over your body as I eased myself in and out and... oh, well you know what it's like."

"Mhmm," she nodded along. She wanted to tell him she knew exactly what it was like to be buried balls deep in his nice warm willing hole. How incredible it felt when she sank all the way into him and flooded her trembling lover with blast after blast of her hot thick creamy load. How good it made her feel when he clenched around her throbbing cock, cried out his undying love and came uncontrollably all over the floor just from having her dick lodged inside him. But she didn't want to interrupt him. She was far too eager to see where this was heading. Her fingers were still crossed.

"But..." He gulped, crap was he really going to say this. "There's this pressure to perform, to make sure you enjoy it, to hold back and delay things as much as possible. When you took me I could relinquish that control, just allow you to use and guide me. Now don't get me wrong I was still doing everything possible to make you feel good too but I felt like I could just let myself go more and enjoy the moment. The feeling of you sliding into me, hearing you moan, knowing how much you wanted me, knowing I was going to bring you to the edge and make you cum deep inside me. It's..." He took a deep breath. "I think I prefer being on the receiving end."

"Oh yes, yes, yessss, I knew it, I knew it." She squealed, hugging him tightly and bouncing up and down a few times before kissing him long and hard. "Oh yesss, I knew it and I'm gonna be fucking you morning noon and night baby. I'm gonna mould your tight little ass to my dick, fuck you until it fits like a glove and you're gonna love me for it. I can always tell Jeff and we're just made for each other. I knew it. I just knew it."

She pulled back beaming excitedly before seeing his worried expression.

"Really? You could really tell?"

"Oh! Err, sorry I meant I could tell from your reactions. From when we had sex. Not just from looking at you. You don't have an 'I like to take it up the butt' face or anything like that!"

"Oh gee thanks," he chuckled, starting to relax again. "My world has pretty much been turned upside down over the last couple of days and I've learned a whole lot of things about myself that I didn't know before... But it's good to know I don't have an 'I like it up the butt' face."

They chuckled and held onto each other for a while longer before they broke apart. Gwen began moving around the kitchen with an extra spring in her step, humming as she happily pulled pots and pans from the cupboard. She was now more certain about him than ever before. She was going to be able to have the type of relationship she'd always wanted with the type of guy she'd always wanted. She'd struck gold. Looking over he still looked a little uncertain about everything.

"Hey, whatever happens in the bedroom you know that when we go out you'll still be my man, right?"

"Yeah I know. Thanks Gwen I needed that."

"Sure thing. Now sit yourself down at the table and I'll get my wonderful little bottom boyfriend some breakfast." He gave her a mock glare. "Hey we're alone and we just had sex so the bedroom rule still counts here," she giggled.

They made small talk as she cooked and laid the table. As they finished eating Gwen brought up their unexpected matchmaker for the first time since the bar last night.

"So," Gwen mumbled, covering her mouth and swallowing her final mouthful of toast before continuing, "do you think you'll miss Tiffany at all?"

"Wow Tiffany, that seems like a lifetime ago, I haven't even thought about her since we began talking last night."

"Aww you're so sweet, same here. So is there anything you'll miss about her?"

"Well she was actually quite a lot of fun when she wasn't being totally psychotic, always keeping me on my toes. In some ways I'll actually miss some of the mind games she played, the mental sparring. Not the full on head fucks she used to pull to try to bend me to her will but the more gentle playful fun ones. We'd spin tall tales and make up silly stories and see how long we could make each other believe it, that sort of thing."

"Well it sounds like you might have a bit of a thing for bad girls, interesting, and yes I know exactly what you mean."

She paused in thought for a while as she finished her drink. Studying him intently and he could almost see the cogs turning in her mind before she spoke again.

"You know me and Tiff are actually very similar. We're both tops in our own way, we both love being in control and I learned quite a lot from her, it was almost like I was her apprentice. I'm kind of surprised you didn't realise that earlier but I suppose Tiffany always did say you were a little on the slow side.

"She did? But... I thought you said you didn't know about me."

"Oh, did I?" She answered innocently while flashing a disconcerting smile at him, suddenly showing an unnaturally large number of teeth and looking at him like a shark looks at a tasty snack. There was a strange glint in Gwen's eye that he hadn't seen before. Mischievous but something else too. Something darker?

"Jeff, make me another coffee!"