Over an Ex and Under a T-Girl

Jeff was deeply concerned to find himself thinking along similar lines. Maybe Tiffany was right about him and he really was too small to satisfy a woman. Maybe what he really needed was a big, beautiful, fun, sexy and well hung redhead to satisfy him instead. He found himself wanting to explore the possibilities with her. Shit! He really wanted this. He really wanted Gwen.

As their interest became more brazen he looked at her more openly, god her tits were amazing, how he longed to hold them in his hands, to squeeze and fondle them. He could just make out the outline of her nipples. The hard suckable nubs showing through her top and bra, calling to his lips and tongue.

Gwen smiled as she saw him staring at her bust. She knew she had a cute face and a nice smile but her biggest assets were an absolutely gorgeous rack and a fantastic ass. Those were her money makers, those are what drew in the boy's stares. Gynecomastia. That had been her secret weapon when it came to her tits, a hormone imbalance caused by a genetic condition meant most of what you saw was actually real. Some small implants deep within to help with the shape and size and hey presto! She had herself a lovely big pair with the natural feel and softness of the real thing. She couldn't wait for Jeff to bury his face in them. If he wanted to of course. Unlike him she still had no idea if he would ever consent to the kind of relationship she desired.

Jeff's eyes wandered down her body to her lap hoping to get a glimpse of her cock, an outline, anything to help him draw a picture of it in his head and Gwen's smile faded. Fuck he's looking at my belly again, the one part of my body that I hate the most. She was unable to stop herself voicing her anxiety and instantly regretted it.

"You're looking at my tummy again aren't you. Look I'm sorry it's... umm." Oh fuck why did I say that! And what was I going to say anyway? I'm sorry it's there! Idiot. Way to blow it Gwen. Good job girl, well done. Five fucking stars... Fuck!

Jeff looked up. He'd been caught trying to sneak a look at her cock again but... hang on, what did she just say? After a moment of relief at her not realising he was just being a pervert he saw the sadness in her eyes. She was vulnerable right now and he had to make her feel better.

"No! Seriously I wasn't looking at your tummy I was looking at..." Shit, what could he say now! No, I was trying to see your cock! He couldn't say that either but she was clearly incredibly sensitive about her looks especially after what that bitch Tiffany had said. He needed to make her feel better about herself, let her know how attractive she was. Think...

"Well OK I was looking at your tummy, but I was trying to work out why you don't like it. I think you've got a lovely, cute little tummy and... well... can I see it?"

"What! No!" She crossed her arms over her stomach and looked flustered.

"Just trust me on this one. Please?"

"I umm, I don't know, it's..." He gave her puppy dog eyes and she glanced around nervously to see if anyone was watching. "Really?"

"Yes, really."

She hesitated before slowly and reluctantly pulling up her top to expose her midriff to him. Of all the parts of her he could ask to see why the hell was he asking to see her stomach.

"Well... what do you think?"

"I think it's beautiful like the rest of you. Can I... touch it?"

What the fuck! She looked nervous before giving a reluctant nod. Jeff tentatively reached out and ran his hand over her belly as she looked on intently, ready to pull her top back down to cover herself the moment he recoiled from her. He slowly ran his hand over it, it wasn't as big as she was making out, maybe like a three or four month baby bump, he wasn't the best at judging those things.

"Mmm it feels really nice. Smooth, soft and warm. Like I said, beautiful. I'd love to wake up cuddling up to a lovely little tummy like this, any man would."

"Really? You don't think I'm just fat."

"No, I'd say you were a bit chubby here and there maybe, but you carry it well. I wouldn't say fat."

"Chubby is just a polite way of saying fat." She added sulkily but with a slight smile at the corner of her mouth suggesting she was pleased with how this exchange was going.

"Or... another way of saying cuddly, curvy, voluptuous, beautiful and full bodied."

He continued to caress her stomach, boldly dipping the tip of his finger below the waistline of her skirt to brush across the very top of her panties. He watched her face, her mouth slightly open and her eyes willing him on as his hand made a second pass, this time dipping his little finger just inside the waistband of her underwear to feel the lightly trimmed hair below.

"And would it matter either way Gwen? I think you look amazing just the way you are."

He moved his hand from her stomach, gliding it to her side as the other hand moved to her back, rising slowly to gently turn her head towards him.

"Can I kiss you," he asked quietly.

She didn't answer but licked her lips and made no effort to pull away. He took that as a yes and slowly pulled her in for a kiss. Tender, soft and chaste. Him with his eyes wide open, watching all the way in for any sign that it might be unwanted. Gwen with her eyes closed and lips slightly parted, leaning in to welcoming their first kiss.

"Mmmm," she purred as he pulled away again, a huge grin returning to her face and sighing contentedly as her confidence came flowing back. "You really know how to make a girl feel special don't you. And I think you might be someone pretty special too but... I didn't know if you'd be interested in a woman like me."

What am I doing? He thought. OK this might be my last chance to turn her down gently. Come on man, come to your senses because this isn't going to work. You're straight and she has a penis. Just tell her that although you find her really attractive, that although you think she's bubbly, fun, quirky, sweet, playful, intelligent and... umm... Aww she's got the cute sexy smile again... OK what was I planning to say... Oh yeah. Just tell her that although you find yourself getting lost in those big beautiful green eyes of hers, with their devilish, mischievous twinkle... that despite the fact that you feel drawn to that sweet kind smile and those plush kissable lips, that, umm... Oh no I think she's expecting me to say something back. What do I say?

He smiled and gave up. "I didn't think I'd be interested in a girl like you either but everything about you is..." He shrugged. "You're an amazing woman Gwen, how could I not be interested." He saw her eyes light up at his words. "But what about you? You were dating Tiffany so do you prefer girls?"

"Well I may have been going out with Tiffy but I generally prefer to date someone with a little more cock." She tittered.

"Yeah, well apparently she did too." He shot back half joking and half insecure.

She giggled, "Aww don't worry, I'm sure you have a lovely little cock." Oops, wrong wording. "I mean a nice cute cock." Damn it, try again. "I mean a nice 'big' cock. And even if it isn't, I wouldn't mind." She reached out to stroke him through his jeans, smiling as he groaned and opened his legs wider to give her better access. "Mmm you certainly don't seem to have anything to be ashamed of down here, although if you want to show it to me I'll give you an honest opinion," she winked.

"Yeah! Well I'll show you mine if you show me yours." Fuck! Did I really just say that?

"Oh wow really?" A broad smile split her face. "Do you really mean that?" Was this actually going to happen?

I really don't know, he thought. "Yes," he said with certainty, "your place or mine?" His penis brain had apparently taken full control of his vocal cords while his rational brain could only scream 'What the fuck are you doing!' into the ether and beg him to slow down and consider this more carefully. Begging him take time to think things through before he crossed that invisible line that could never be uncrossed.

Yes, this is actually going to happen! Gwen thought excitedly. She quickly brushed down her clothing, smoothing out her top with trembling hands and practically jumped to her feet.

"Well come on then," she said with the excitement clear in her voice, "my place is just around the corner." She pulled him up from his seat and ran her hand down his chest. "We can go there and umm, get to know each other better, see what we both have to offer if you know what I mean." She bit her lip, internally debating whether to say what she wanted to say before deciding to just go for it.

Leaning in she whispered into his ear. "And you know the unspoken rule about dick size don't you? That the person with the biggest cock does the fucking."

"Yes."

"Well..." she asked with a trembling voice, "do you agree with that rule baby?"

"Ye-yes," he stammered.

"Oh wow, Oh yes. Oh you won't regret this. You're going to love having me deep inside you, I can just tell," she squealed excitedly, wrapping her arms around him and leaning in to give him a full, long and deep kiss. Her tongue easing it's way between his lips to dominate and claim ownership of his mouth, leaving him weak at the knees. He squeaked adorably as one of her hands slid down to squeeze and grope his firm virgin bottom. "Mmm," she said, pulling back with a dreamy smile. "You're such a good kisser, I can't wait to get you back to my place and put those sweet lips of yours to work somewhere else." Her eyes sparkled and she gave him another wink. "Come on let's get you home."

"Okay... Ahh," he chirped as she gave his bottom a quick little swat, grinning at him as he walked past her.

**********

What the hell have I signed up for? He thought as he walked down the road arm in arm with Gwen. Tiffany was right about her, she's a total top and I think I've just agreed to... bottom for her. Oh fuck, oh fuckety fuckty fuck. Jeff didn't know whether he was more scared or exhilarated by this new confidence she'd found and the sudden dominance that came with it. One thing was clear to him though. There was no way he was going to back out of this now. For better or worse he was fully committed.

Gwen was equally surprised by her boldness. She had always been a top but a shy and timid top, almost like she was embarrassed for having such urges, for wanting to be the one doing the fucking. It could have been the crazy way the day had played out that had caused this seismic shift but she thought it was him. For some reason Jeff was pressing all her buttons and bringing this barely controllable passion out of her. Everything about him was adding up to a burning desire to take him to her bed and make him hers. She may have only met him this evening but no one had ever made her feel this way before, made her want them so badly.

They both walked on burning with anticipation.

**********

"Well we're here. Are you ready to come inside? Or... ready to let me cum inside you?" She asked provocatively and biting her lip before giggling nervously. Shit, I really shouldn't have said that. I want to be sexy and fun but... fuck I'm such a horny mess tight now, I'm no good at this sort of thing and need to get a grip before I scare him away.

"Yes I'm ready for... umm yeah I'm ready," he gulped. 'I think,' he added in his head. "Shall we go inside?"

She opened the door and he stepped into the lioness's den. Not knowing for sure why he was doing this but knowing with absolute certainty that if he turned away now he would always wonder what might have been.

Once inside they shut the door and faced each other, each pressed up against opposite walls, panting and waiting for the other one to make the first move. Moving slowly in to meet in the middle they both turned their heads the same way, bumping noses and giggling nervously before trying again. This time their lips met and parted as they slowly explored each other's mouths, neither rushing as they gently caressed their partners bodies.

They broke apart after several minutes. Smiling shyly at each other, more relaxed and at ease.

"Come on in, kick your shoes off and I'll show you around my place. There's not much to see really." He followed her around the small apartment, "There's the kitchen, this here is the living room, obviously, and through that door there," she said, fixing him with a steely gaze, "is my bedroom."

As she gave him her bedroom eyes she noticed a look of terror passing through his own. OK it was clearly too soon for that, he wasn't ready and she needed to slow things down again, give him more time. She knew something would happen between them, all the chemistry was there but she had to be careful not to scare him away, she had to pace this right.

"Or we could sit here," She said, plonking herself down on the sofa and patting the seat next to her. "First things first. I've got to do something because you've been making me feel really uncomfortable all evening."

"What? I have? Sorry Gwen I didn't know." He replied, panicking slightly as he sat down.

"Relax silly, it's nothing you've done wrong, you've been making me uncomfortable because I'm all tucked and taped. Just give me a minute to..." Staring into his eyes and biting her lip she moved her hand up under her skirt and into her panties before releasing herself and letting out a long exaggerated sigh of relief, "uhh ooooh yeah, that feels sooooo much better," she groaned. She continued to stare into him, keeping his gaze locked on hers as she settled back down onto the sofa, spreading her legs slightly and carefully withdrawing her hand. "It's been struggling to get hard all night."

She smiled at Jeff and tormented him by maintaining eye contact. Knowing he was desperate to look down but unwilling to let her see him do it. His eyes started flickering, the lure of her crotch becoming almost unbearable.

"Go on then, have a look," she giggled.

His eyes shot to her lap and his mouth hung open as he saw the bulge through the material of her clothing. She looked huge, far bigger than him. No wonder she was a top.

"You... You didn't take it out."

"Of course not sweetie, where would be the fun in that? If you want it you'll have to go in and get it," she teased before turning more serious. "But Jeff, I honestly don't want to rush you or pressure you into doing anything you're uncomfortable with. You just have to let me know if I'm moving too fast for you or if you need a timeout, OK? I'm guessing this is all new to you so if you'd rather just sit here for a while and talk then that's perfectly fine. Or maybe we could make out a little more, I'd definitely like that, Or..."

She stopped talking and held her breath as he tentatively put his hand on her leg, slowly running it up past her knee and under her skirt. It continued across her inner thigh to grip her through her panties, wrapping around to touch someone else's dick for the first time. He traced the outline a few times with his fingers, gliding them up from her balls to her tip before allowing them to drift back down again as he assessed her length. "Oh wow," he mumbled as he cautiously reached inside to take it in his hand, gripping and slowly massaging it to it's full size. He finally looked back up into her wide open sparkling eyes.

"...or you could just stroke it like you're doing now," she whispered breathlessly.

"And what would you like me to do?"

"Oh I think you already know what I'd like you to do honey."

He moved in to give her a quick peck on the lips before pulling back and saying, "I want to do those things too." They smiled at each other and kissed again, longer and deeper as he gently worked her shaft.

"You like how that feels baby," she panted, breaking the kiss.

"Uh-huh. It doesn't feel hugely longer than mine but it definitely feels a lot thicker," he said with a touch of awe in his voice.

"Yeah I'm a girthy gal," she giggled, "and it's eight inches if you're wondering. Is this the first time you've touched someone else's cock?" She asked gently.

"Yes."

"Well... in that case would you like to go down and have a closer look?" She asked tentatively.

She moved her knees apart and with a glance told him where she wanted him to be, biting her lip as she waited for his reaction. She was still determined not to push him too hard or too fast but was desperate to see him on his knees. She needed this so badly. The hand holding her cock paused for a moment before it resumed its movements, he gave her one more sensual kiss, nodded and slid off the sofa to sink down between her legs. She giggled as he tried to take a furtive look up her skirt as he settled on the floor before glancing back up at her again, as if asking one last time for permission. He's so sweet and innocent, she thought, almost begging to be corrupted by a naughty little angel like me. She gave him the go ahead with a quick nod.

Running his hand up her leg, past her knees and across her broad meaty thighs he slowly hitched her skirt up to her waist, finally exposing her large cock. "Oh wow," he mumbled as he took in the sight before him, making sure to commit it to memory, "It's incredible!" He looked back up at her. "You have a beautiful cock Gwen."

"Mmm she likes you too, would you like to give her a little kiss."

She held her breath as he gulped and summoned up the courage to lean forward and kiss the tip. It twitched as his lips touched it and he drew back startled, causing her to chuckle lightly as he glanced up with a sheepish smile.

"No need to be scared honey, she's just excited to see you, come on now, open up so you two can make friends."

He leaned back down with an open mouth, extending his tongue like a red carpet to welcome in his new best friend as he closed his lips around it.

"Oh yesss that feels wonderful, mmm yeah she 'definitely' likes you baby. 'Oooo yes, just like that." She spread her legs wider and moved her hand to the back of his head, lightly petting him as he worked away. "Mmm I love what you did with your tongue just now, can you do that a bit more sweetie? Uh-huh, that's right just lap around the head a bit more and then tickle the slit. Oooo that's so nice. Now see if you can take in a little more baby. Yeah that's it, now you're getting nice and deep, ooooo gooood boy," she cooed encouragingly. He moaned loudly and started working himself up and down her member with far greater enthusiasm.

"Oh that's so good," she panted, "mmm yeah you really love that I don't you," she rested both hands on his head and started making slow shallow thrusts into his mouth, working in harmony with him. "Mmm you're doing really well for your first time, far better than most and far better than I expected, you're a natural baby, ooooh yesss."

Jeff paused for a second as the reality of that statement suddenly hit home. He was a natural. A natural cocksucker! He was actually sucking her cock. He'd got so caught up in the moment with this sexy, playful redhead that when she had directed him onto his knees he hadn't even thought about it. He'd just sunk to his knees in front of this beautiful woman, exposing her thick throbbing needy shecock and taking it into his mouth. Working it with his tongue, revelling in that first taste of sweet salty precum, swallowing it down and lapping at the slit for more. He moaned around her girth as another delicious little spurt was released and greedily sucked it down. Oh fuck her cock felt and tasted so good.

He looked up into her smiling green eyes as she gently slid herself in and out of his mouth, biting her lip with a look of sheer bliss and realised that he'd resumed sucking pretty much instantly. He mentally shrugged, whatever issues he might have to deal with could wait. All that mattered right now was pleasing Gwen, getting to see her face as she released, seeing the 'O' on her lips as she passed the point of no return and pumped her seed deep inside him. He'd do anything to make her cum and he wanted her to know it.