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Natalie's New Student April 2022 SotM
🕑 Added 2022-04-10 04:42:15 +0000 UTCNow that Maddie's a new woman with her new husband Natalie has to get a new playmate to have fun with. Who would have guessed it would be her muscle bound crush from high school?
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Natalie’s New Student
Contains Gender TF
Written By: https://www.furaffinity.net/user/Roushfan5
Illustrated by: https://www.furaffinity.net/user/xchiseaxmargaritax
“You want me to what?”
Natalie hadn’t meant to laugh when Jeremy approached her at her little sister’s wedding.
She was all too well aware, even if only second hand, of the struggles that trans people went through as they fought for acceptance. Natalie also knew that it had probably taken a lot of courage for Jeremy to approach her with his problem. In a culture that stressed so much importance in acting ‘manly’ it wasn’t the sort of things most males would be proud to admit. It had likely a great deal of soul searching to even realize he needed her help. Yet, the busty dog girl had been unable to help herself, she was drunk and taken by surprise by Jeremy’s request.
“I want you to do whatever it was you did to Matt.”
“Maddie.” Natalie gently corrected, although she also found herself slipping up from time to time. It had only been three weeks since her sister had stopped using her ‘dead name’ and Natalie had only just started to get used to calling her ‘Samantha’.
“Fuck.” Jeremy cursed. “Yeah, that’s what I meant. Sorry, force of habit.”
Natalie said nothing, instead the two canines fell silent for a while as they turned to look out onto the dance floor, where Maddie and her new husband were still dancing together. The blushing bride’s rounded belly was already starting to show her pregnancy through her wedding dress, much to their father’s annoyance. Bits of wedding cake, when James had stuffed a slice of cake into her face, still clung to her short fur. But the mess didn’t hide the smile that was etched onto her face. It was a look that filled Natalie’s heart with a lot of joy, knowing the pain and confusion it had taken to get her little sister here.
Beneath the joy, however, Natalie did feel a small pang of sadness. The wedding represented the opening of one happy chapter in Maddie’s life, but also the closing of another. She was now a wife, soon to be a mother, and Natalie already missed the carefree fun she and her sister had together as her alternate ego ‘Samantha’.
She turned to Jeremy and looked at him appraisingly. Jeremy was an old high school friend of Natalie’s. The two had never been particularly close. In fact, Natalie didn’t think she had spoken or thought of him much since their graduation. It was a sheer coincidence that he’d been a caterer for the wedding. Still, they had run in the same social circles, Natalie one of the popular girls and Jeremy one of the popular boys, and had spent a fair amount of time together. Natalie had always liked him a lot: he was rather quiet at first, yet very smart and hilarious once you got him talking. He was handsome, tall with a lean yet muscular build and had a very kind face. Truth be told, he was actually Natalie’s first crush, even though it hadn’t gone anywhere. At a glance, the lab was an All-American boy, and it was hard for Natalie to see him as anything else.
Yet, he wanted Natalie to help turn him into a woman.
“You know you could just go to Lewd Brews and buy the same potion we did, right?” Natalie asked hesitantly. She hadn’t exactly wanted to tell him this, hoping that maybe he could help her more than she could help him. She wanted someone knew to train now that Maddie was on her own, but she didn’t feel right hiding that information. It turned out not to matter, however, as he shook his head.
“I know… but being a girl is more than just having boobs and vagina.” He said, looking nervously around the church, as if god would strike him down for talking about body parts in church. “None has ever taught me how to put on makeup or how to put together an outfit, ya know? And it’s not like I have a sexy big sister to help me like Maddie does.”
Natalie blushed a little, which surprised her. She usually wasn’t the type to get flustered after a compliment. Perhaps she was nursing more of a crush over the lab than she realized. “If you think I’m sexy, why did nothing ever happen between the two of us?”
“What do you mean?”
“You know what I mean!”
It was now Jeremy’s turn to get flustered. “I guess I never thought you’d be interested in the quiet type like me. You were always going out with the jocks and party animals.”
“I went out with the jocks and the party animals because they were the ones that asked me out!” Natalie protested. “I’ve never, ever turned a guy down for a date. Unless he was being really fucking creepy or otherwise sending out untrustworthy guys. You though? I’d let you bend me over in the confessional booth right now if you wanted.”
She smirked as she watched Jeremy’s eyes light up with interest and surprise, even as he checked around to make sure none was overhearing their conversation. For a hopeful moment, Natalie thought the big stud muffin was going to take her up on her offer. “Maybe later.” He said quietly. “But does that mean you’ll help me?”
“Yeah, I’ll help you. Give me your number, we can work something out after the wedding.”
She could tell that Jeremy was a little hesitant as he reached for his phone, Natalie was starting to wonder if he was having second thoughts. But they did exchange numbers and left Natalie to hope for the best.
…
It took Jeremy three days after the wedding for the shy lab to reach out to Natalie.
By the time he finally called she’d been wondering if he ever would! Once he finally contacted her, Natalie made sure to set up a date as soon as possible, not trusting Jeremy to chicken out if she let grass grow under his feet. If Jeremy tried things on the female side of the gender divide and it turned out he didn’t like it, that was fine. But she wasn’t going to let him settle for a life of unhappiness due to cowardliness! Luckily, Natalie’s new job at Lewd Brews meant she could finally afford an apartment of her own, this made it much easier to invite friends over, especially boy friends. Her father would have a hissy fit if ‘too many’ guys started showing up at the house, which used to make setting up plans much harder. Now she didn’t worry at all when she told him to show up at five o’clock sharp.
“Five?” He asked curiously. “Why so early?”
“Because we’ve got to get you ready, silly.” Natalie laughed.
“Ready for what?” He continued to probe, a wary tone to his voice.
Natalie bit her lower lip and wondered what to say. If she told him her full plan he might chicken out, if she didn’t tell him enough information he might chicken out anyway. “Don’t worry, I won’t force you to do anything you aren’t ready for. You’re gonna have to learn to trust me if this is a going to work out!”
There was another long silence over the phone, and Natalie was worried that she’d lost him but after only a slight moment of hesitation he agreed. And, five on the dot as he promised, he showed up to Natalie’s apartment ready for the first day of his new life.
Many transgender folk very quickly realize that there is something different about them from a young age. Jeremy wasn’t quite the same way, perhaps in part because he was the picture of masculinity. Tall, muscular, and hung the idea that he could be anything besides a guy seemed absurd, even to himself at times. But when he saw Matt, now Maddie, on her wedding day way happier than she’d ever seemed back in high school, he suddenly realized maybe there was an alternative way of being after all. Suddenly, things started to make sense. Why he’d never really been happy, even if from the outside looking in he seemed perfectly content. He decided that the only way he was ever going to find out was by trying it out, and that was why he came to Natalie’s apartment.
They greeted each other warmly, if a little awkwardly, as Jeremy still didn’t know what exactly to expect from his evening with Natalie. She offered him a drink and he declined, so they headed back to the vizsla’s bedroom. Now it was Natalie’s turn to felt strange, she wasn’t used to bringing a boy into her bedroom without the intention of sleeping with him before!
“Ok Jeremy, first things first…” Natalie walked to her bed and turned to present the lab with two different options, one clenched in each paw. In her right was a skimpy little outfit that she figured would look good on the lab, in the other was a small potion bottle. “Do you want to do this the fun way or the fast way?”
“Er, what’s the difference?”
“Well, the fun way is you and I go on a little crossdressing adventure. Sort of just dip your toe into the pool.” Natalie lifted the outfit a little taller, as if offering it to the taller fur. “The fast way is this little potion bottle right here!” She shook the small glass bottle, a pink liquid sloshing around inside.
“And what does the potion do?”
“Turns you into a full-fledged, cis woman. Tits, pussy, uterus, and all!”
“For how long?”
“As long as you want it too.” Natalie said with an excited grin. She was in her element, helping another wandering soul find his way to womanhood. “I got you the permanent version, but as long as you don’t get yourself knocked up, you can reverse it any time by taking the reverse potion.”
Jeremy’s eyes got big, matching Natalie’s excitement. He nodded his head and pointed at the potion bottle. “Definitely that one!”
Natalie was a little disappointed, but not surprised. She supposed she couldn’t blame someone for being eager to realize a lifelong dream. The busty dog girl put the outfit to the side, they would need it again shortly. “Potion it is, then! Why don’t you strip real quick, so we can witness your transformation better.”
It was a good idea, but the bubbly and fun Jeremy was starting to come out now that he was getting excited. He took his jacket off while flashing a flirty smile at Natalie. “Oh, is THAT why you want to see me naked?” He teased.
“Among other things…” Natalie responded while her tail wagged and ears perked up in interest. She watched as Jeremy threw his jacket across the room and then his shirt. Natalie had to work hard not to lick her lips as jacked canine exposed his delicious looking six pack for her. “Good boy…” She cooed.
Jeremy’s shoulders slouched a little and he looked away from Natalie, embarrassed over the ‘good boy’ comment. He wasn’t used to women taking control like this! Yet, Natalie could tell he liked it. The bulge in his jeans had become more pronounced, his tail began to wag back and forth a little. He hesitated to take off his pants, but Natalie came over with a little encouragement.
“Come on big boy!” She cooed, standing on her tippy toes to nibble on Jeremy’s neck while tenderly rubbing his muscular torso. “I can tell you’ve got nothing to be ashamed of!”
Her hand reached lower and started unbuckling Jeremy’s belt. He was shocked how effortlessly she removed it one handed, better than he could have done with two hands he guessed. “Get a lot of practice at doing that?”
“A fair amount.” Natalie responded, a pouting frown crossing her face. “But don’t be catty about it, I’m sure you’ll get plenty of opportunity once Ex-Y is coursing through your veins!”
Jeremy’s face fell a thousand degrees as he processed what his comment had sounded like. “Sorry!” He quickly said, not wanting to offend anyone. Least of all the woman who was helping him like this.
“It’s alright…” Natalie responded, with a gentle, almost motherly tone. She was doing her best to soothe her big giant now that she was working over his button and zipper, allowing his pants to fall to the ground. “Holy balls… literally!” Natalie had assumed his cock was growing hard inside his pants, in reality it was still half flaccid. Slowly yet impressively coming to life as Natalie flirted with him. It just wasn’t the lab’s cock that impressed her, though. Balls didn’t get enough love, Natalie thought. Sure, they were the second act compared to the cock, but that didn’t make them any less important. His balls hung low and heavy right behind Jeremy’s mighty cock and she could just imagine feeling them smash against her as they fucked.
“What’s wrong?” Jeremy asked, raising an eyebrow as his kick himself free of his pants.
“Nothing is wrong… it’s just are you sure you wanna get rid of this thing?” Natalie reached over to tenderly touch it, running her fingers up and down its length. “It might be the best cock I’ve ever seen.”
Jeremy looked sheepish yet again, unable to make eye contact with either himself or Natalie in the mirror. “Thanks…” He said sheepishly, before an idea suddenly came to mind. “You know though… even if I want to be a girl, I still like chicks. So if you wanna give it one last ride before.”
He didn’t even get to finish his sentence. Before he could get the words out Natalie had grabbed him by the scruff of the neck and started leading him over to the bed. “Oh, I’m going to give it one last ride!” She announced, shoving the big stud to the bed.
END
THANK YOU FOR YOUR PATRONAGE!
