Over an Ex and Under a T-Girl

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A messy breakup and a soft seduction with a gentle TS top.
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TGPstories
TGPstories
740 Followers

"So... When's your harpy getting here then?"

"Ah she's not that bad really," Jeff replied unconvincingly. She was and she was getting progressively worse.

"She's just using you Jeff. If you didn't work in advertising and take her out to fancy parties to hobnob with celebrities she wouldn't give you the time of day. Do you even like her?"

"Yeah I kinda like her, she's... OK," he lied.

"No she's not. And as soon as she meets someone better she'll be off like a shot... Oh, shit... I mean... umm when she meets someone she thinks is better. Not that err, she can find someone better than you."

"Ha! Yeah, yeah don't worry I know what you meant. And yes I'm pretty sure she's been looking around too. To be honest I really hope she finds someone soon and just naffs off and leaves me alone."

"So why haven't you left her already?"

"Well she looks amazing so it's pretty good to have her hanging off my arm at all those events." Even that was a bit of a lie. While it was good to walk in with a stunning woman she did tend to flirt a bit too much with other people and sometimes it became a little embarrassing, especially when she was drinking.

"Plus everytime I'm planning to finish it with her we somehow end up in bed. You can't just dump someone straight after having sex you know, it's just wrong," he said, finally admitting the truth. "So then I have to leave it a few more days, and then we argue, and then we go to bed, and then I have to leave it a few more days. Do you see my problem?"

"Yeah. You're an idiot. Just man up and finish it already, even if it is just after sex. Just pat her nicely and say there you go sweetie, I've left you a nice little creamy going away present. Now fuck off and don't come back."

"Ha yeah right, like you'd ever do that," Jeff said laughing. "Seriously though the sex isn't even that good anymore. She doesn't even look that interested half the time and sometimes we're just going through the motions. I'm half expecting to catch her scrolling through her phone mid coitus one of these days," he chuckled before turning a little more serious. "I think she might actually be seeing someone else behind my back."

"Then you should be looking around for someone else too you dumbass."

"Nah can't do it. I know what you're saying but that's not me. It's not right and... Oh hey Tiffany, good to see you."

"Hi Jeff," she kissed him on the cheek with a faked warmth, "David." She said with an unfaked coldness.

She sat down and ignored them both, glued to her phone and lost in one of her frequent moods. Jeff shook his head and sighed, he could ask her what was wrong but that would risk her telling him and then he would have to pretend to listen and care.

Tiffany could be really witty, fun and charming when she wanted to be but there was a dark and manipulative side to her personality that was becoming more and more obvious as time went on. To his shame he had put up with her antics for almost four months now. Her killer body and sexual availability keeping him by her side, between her thighs and under her thumb. Admittedly it was nice to walk down the street with a girl who could turn most people's heads but the trade off had stopped being worth it a long time ago.

Right! All he had to do was avoid sleeping with her for a couple more nights and wait for their next fight so he could walk away as the good guy. He knew he wouldn't have to wait long but the opportunity was about to come up a lot sooner than he thought.

"Hey guys did you miss me?" Rita called out as she walked over to give David a kiss on the lips. "Sorry I'm late, woman's prerogative, come on Dave we need to leave now or we'll miss the concert."

"Yeah we need to be leaving too," Tiffany said, finally putting down her phone, "Jeff's taking me to the Ivy today. It's expensive but he loves to treat me and it's really no less than I deserve and... Oh Shit!"

They looked in the direction Tiffany was staring and saw a redhead approaching them with wide open arms and a warm, infectious, heartfelt smile that Jeff couldn't help but return. She was carrying quite a few extra pounds but was curvaceous and carried it well. On first impression she seemed like a really nice friendly girl. Bubbly and cute. Just watching her walk in was enough for him to instantly know they'd get on like a house on fire.

"Tiffany! How are you? I saw you from outside and I'm so excited to finally get to meet some of your friends. I'm Gwen by the way and I don't know how much she's said about me, nothing bad I hope, but me and Tiff are... well kinda going out now I suppose." She gushed. "Early days but she's been so sweet."

"Shushhh. Not here, not now Gwen! You're embarrassing me!" She hissed.

"What do you mean?" she said with a hurt expression. "You said you'd told your friends about me. That you'd introduce me to them. You promised Tiffy."

"Yeah! Well I didn't, did I! I actually have a boyfriend Gwen and even if I didn't, do you really think I could have all my friends thinking I was going out with someone like you?" She seethed.

"What!" Gwen's face dropped and she took a couple of backward steps as she saw the dark side of Tiffany coming through for the first time.

Jeff jumped to his feet, he had no idea who this woman was but he couldn't just sit there and watch her be abused like that.

"Fucking hell Tiffany, why do you have to be such a bitch! What the hell has she done to deserve that!"

"Oh shut the fuck up Jeff, we can talk about this later after we've eaten. Now let's just go. I've got all dressed up for tonight and I don't want this evening ruined."

"Unbelievable. There won't be a later Tiffany, that's it, we're done, we're over."

"What do you mean we're over? We're not over, we have plans. The award ceremony is next week and I've been looking forward to it for months."

"Wow! You're seriously delusional aren't you? I'm not taking you anywhere. I don't know how or why I've put up with you for so long but you're dumped Tiff, do you need me to draw you a fucking diagram or something, should I take an ad out in the local paper. You. Are. Dumped."

"What!" Shouted back a furious Tiffany. "You're actually dumping me! You," she gestured dismissively at Jeff with a look of incredulity, "dumping me!"

She shook her head, genuinely struggling to comprehend what was happening. Him dumping her! No one fucking well dumps her she was gorgeous and he was... Argh! How fucking dare he! How the hell could he humiliate her in public like this. Her shock quickly turned to anger.

"Fuck you Jeff. I've been slumming it with you! Do you think you'll ever get with someone as hot as me again? You," she said jabbing at him with her finger, "were single for well over a year before I took pity on you."

She stopped talking and paced angrily back and forth while considering her next verbal broadside, carefully considering how to cause maximum devastation. It was a forte of hers. She rounded on him with an evil glint in her eyes, not caring who got caught in the crossfire.

"I've been fucking Gwen here behind your back for over a month Jeff," she said with a cruel smile, "and do you know why I've been cheating on you? It's because you can't satisfy a woman in bed." She held up and wiggled her little finger. "Your dick is too small, too thin and you've got a fucking lousy technique to go with it. You're not even any good at oral and with your tiny prick you really should have upped your game in that department. Why do you think I had to go out with Gwen? She's a shemale Jeff," she smirked, "and she's fucking hung."

"What! You're joking right?" He glanced at Gwen who's eyes were wide with shock and then back to Tiffany who was practically creaming herself in pleasure at the revelation.

"Nope, it's all true babe. Gwen has a big, thick, fat, shecock and unlike you she actually knows how to use it. Maybe you should let her fuck you too. She's a top and prefers men anyway it's just that she can't get one. You'd be perfect for her though. You're a big enough pussy to simply bend over and take it like a good little bitch. The only thing you've got going for you is a nice arse so you might as well get it filled. Go for it honey bunny." she added with mock sweetness. "You might learn something and if you do turn gay then what the hell, it'd be no loss for womankind." She shouted the last part with real venom and stood there panting.

"Tiffany!" Gwen shrieked, finally breaking out of her shock. She shook her head and quickly dropped to a tone not much higher than a loud whisper, designed to reach the ears of Tiffany only but easily overheard by the three friends. "How could you? And how dare you tell people my secret!" She seethed. "I'm the only one who can decide who does and doesn't know that. I've told you how sensitive I am about it! I trusted you for fucks sake. How could you betray me like that?" ... "I thought you cared." She sniffed sadly.

"Oh fuck off Gwen," she replied at the top of her voice. "I'd tell you to grow a pair but you already have. And why the hell are you acting like this? Like you're the one who's being wronged here. I'm the one who has just been outed as going out with a fat fucking tranny! How do you think that makes me look?"

"I... I..." Gwen turned and stumbled back out into the night, leaving the silenced bar with it's staring denizens behind and fleeing into the darkness.

"Oh you're leaving... Shame! And what's that I can hear in the distance? Is it the sound of cakes crying in terror at your approach?"

"What the fuck is wrong with you!" Jeff screamed at Tiffany and set off after the poor girl.

"Oh yeah that's right Jeff. You just chase after the girl with the big cock rather than stay here with your hot girlfriend... Arsehole... You don't even know her... She's such a needy fucking nightmare... You come back right now do you hear me..." You could hear a pin drop. "Well you just fuck off too then... You know I'm totally out of your league you small dicked loser. You'll never get another girl like me... Fuck!"

She stood quietly for a few more moments in the silenced bar before sighing and continuing in a much lower tone.

"Why does no one ever ever think about me? Why does no one ever take my feelings into account," she sulked.

"Hey Tiffany."

"Ugh, and what do you want Rita?" She said, turning to face her with obvious disdain.

The last thing Tiffany remembered before waking up on the floor was a fist barreling towards her face.

**********

"Gwen! Gwen! Wait up."

She stopped in the road and wiped away a tear with her sleeve, sighing and slumping her shoulders before turning to face the guy from the pub. She thought his name might have been Jedd or Jeb or something. Once the shouting started she kind of got lost in the unravelling nightmare and all she wanted to do was get home, curl up into a ball and cry.

Gwen knew he'd been on her side at one point but now he knew her secret he'd have put up the barriers, he wouldn't see her for who she really was, he'd just see her as Tiffany saw her. Just as some fat tranny to be mocked and pushed around. That's what they would all see from now on. What was he going to do? Apologise to her or shout at her for sleeping with his girlfriend? Whatever he did she'd just accept it and move on. She felt broken.

Jeff walked up to Gwen and wrapped his arms around her as she froze. "I'm so sorry you had to go through that. No one should have to face that," he said, rubbing her back.

As he hugged her tighter her paralysis broke and she threw her arms around him, sobbing onto his shoulder and suddenly totally dependent on the comfort of a stranger, clinging to him like driftwood in a tempestuous sea. They stood in the middle of the road, simply holding onto each other and with neither willing to let go. Gwen slowly relaxed into the hug until the sound of new voices caused her to freeze once more as she desperately tried to work out whether they were friends or foes.

"Hey it's Gwen right?" Rita asked with concern. "Are you OK sweetheart?"

"Yes, yes... I'll be fine... Kind of used to it now," she gave a half smile.

"Well you shouldn't have to get used to crap like that." Rita shook her head and turned to Jeff. "You're going to look after her for a bit right? Make sure she's OK? We really have to be going but we'll ditch the concert if you need us to stay with you, it's no biggie."

She paused for a moment and remembered all the shit Tiffany had thrown Jeff's way. Damn she hadn't even asked about him. He was usually big enough and strong enough to hold his own but that was pretty rough on him too.

"And how are you holding up Jeff? Gwen got it far worse than you but she wasn't the only one to cop some flack in there."

"Yeah you don't have to worry about me Rita. Me and my mirco-penis are doing just fine," he smirked back. "And yes I'll make sure Gwen is OK, you two head off and have some fun."

There was a fair amount of bravado in that statement and although he was hiding it pretty well inside he was in some turmoil. Did she really cheat on him because he had a small dick and was crap in bed? He'd measured it before and it was just shy of six inches so not too bad at all. Just under five and a half was supposed to be the average but what about girth? Was it too thin? He wasn't about to ask David to whip it out to do a comparison and he knew comparing it to Gwen's would be a mistake. It would be a damn sight harder to ask her as well but he did find himself a little curious.

For some reason he found himself really wanting to see her penis and he started to actively scan his body for any feeling of her pressed up against him. Disappointingly, he couldn't feel it against his leg. Damn, why the hell is that disappointing? Well it's only natural isn't it, he told himself, to want to check out the competition, nothing more than that. He shook himself out of it.

David was, unusually for him, the only one who didn't have sex related anatomy on his mind, he was much more concerned with Rita right now. "Are you sure you don't want to get some ice on that hand?" After a quizzical look from the others he added proudly. "It's a bit swollen. Rita punched Tiffany out."

This earned her a high five from Jeff and she winced in pain at the contact but it was totally worth it.

Gwen settled down as they said their goodbyes to the couple and she allowed Jeff to convince her to go for a drink with him. The reluctance was pretty much faked and short lived. She had only recently moved to the city, had few friends here and really didn't want to be alone right now. She was glad to have someone to talk to and doubly so as he knew her secret and had accepted her. Maybe something good might come out of this horrible night after all.

**********

After a brief argument at the bar about who got to buy the first round a smiling Jeff brought the drinks back to the booth. It was so refreshing to have had an argument with a girl that didn't involve irrational demands.

It also meant he'd got to watch her walk back to the table. She had a truly exceptional bottom, big but round and firm with a fantastic wobble as she walked. On his own walk back he was able to check out her front properly for the first time. Gwen had nice big boobs that were at least an F cup and suited her larger than average frame. She had long wavy red hair, green eyes that sparked when she talked and of course that wonderful warm smile. She really was a wonderful mixture of sexy and cute.

Jeff shuddered himself back to reality. She had a penis, an apparently huge and dominating top's penis if his lying cheating ex could be believed, so why was he looking at her as a possible future love interest. There was definitely something that drew him to her but it was far too early to know what it was, just a feeling, something intangible. Such a shame about the dick, otherwise who knows what could have been.

He sat down, sliding over her drink and raised a toast. "To crazy ex-girlfriends."

"To crazy ex's." She replied, raising her own glass and once again treating him to one of her dazzling smiles. "Oh, and I'd never have gone out with her if I thought she already had a boyfriend."

"Yeah you did look a bit shocked at that. And I'd have never gone out with her if I'd known how much of a psycho she was but that's life." He shook his head. "In the beginning she was actually quite nice and... well you should know. She's always been a bit Jekyll and Hyde and had her bad moments but tonight was something else. I seriously can't believe she did that though. I genuinely think she might be a sociopath."

"Ugh I don't even want to talk about her anymore. Let's change the subject err, kittens and puppies, let's talk about them instead."

"Ha, you're so girly aren't you, I love you already," he laughed, causing her to blush and she shyly brushed her hair out from her eyes before tucking it behind her ear.

Damn she's cute, he thought again, before wondering what her cock would look like, how big it would be, how heavy. What would it feel like if he held it in his hand with its supposed extra length, girth and weight. He'd probably have to give it a little stroke to find out, to get a proper feel.

Still blushing she glanced away to hide the colour spreading across her features and he stole a quick glance down, trying to catch a peak of the bulge hidden away in the panties beneath her simple yet elegant skirt. Gwen's penis was tucked and hidden away so he wasn't not able to see anything and he couldn't stop the flash of disappointment showing in his face.

Crap! Why am I so desperate to see it? Double crap I'm sitting here imagining giving her a handjob! Oh treble crap. He'd been staring at her lap too long and when he looked up she had noticed him. He could easily guess at what she was thinking.

And what he guessed was wrong. What she was thinking was far worse.

He's looking at my tummy, my big fat tummy, she thought with a little sniff. For a moment I thought he might actually be interested in me but that bitch Tiffany was right. No one wants a girl like me.

"I have a cat!" Jeff suddenly blurted out to hide the embarrassment of being caught. "So kittens, cats, same thing right?"

"Yeah?" She breathed deeply and forced a smile onto her face. "What's its name then? Tell me all about your cat," she asked as they finally pushed the awkward moment behind them and fell into casual conversation.

They talked for hours, the conversation flowing easily as if they had known each other for years. Much of it was banal at the beginning, work, tv, music and cats obviously, but towards the end it became deeper and she told him her full story. How she transitioned and moved away to get a fresh start. How she met Tiffany through a friend of her sisters and how she had eventually told her about her extra appendage as she was desperate for a confidant in the new city. Tiffany being Tiffany had insisted Gwen show it to her and on discovering how well endowed she was had, quite literally, jumped on the opportunity.

Despite her initial thoughts about Jeff having zero interest in her the pair found themselves flirting with each other ever more openly and the time swiftly flowed by. Both of them were unsure of why they were coming on so strongly and so out of character, both unsure about how far they would even be able to take this. It could all be just a reaction to the earlier drama, a need for validation and approval, a way to show the world that Tiffany was wrong about them and that they were desirable, that they were indeed wanted and coveted by another.

But of course there was also a more tantalising possibility that there really was a deep connection between them. They just seemed compatible, they clicked.

Gwen wanted someone to love and she ultimately wanted to express that love by spreading their legs wide and sliding herself deep inside them. She wanted to make her lover moan her name and cling to her as she filled them with her throbbing womanhood and hot creamy girl goo. She couldn't help wondering if Jeff would be open to the idea of accepting the alternative role in the bedroom. To allow himself to be penetrated by a kind and loving but sexually dominant partner. To be filled and fucked. Loved and taken.

TGPstories
TGPstories
740 Followers