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“I got the stuff.” Illi said, pulling the box of condoms out of her shoulder bag. She’d shoved them in there earlier at the drug store - too embarrassed (not to mention broke) to buy them herself. She’s pretty sure that the old lady working the register had seen her do it, but she hadn’t called Illi out so she was considering it to be a win. Maybe the lady was just glad that teenagers were practicing safe sex.
Condoms were a non-negotiable for Frank - not that Illi was planning on forgoing them. He wasn’t on any kind of birth control seeing as his parents didn’t even know that the two of them were dating. They’d met Illi a few times but didn’t know that she was trans, nor that she was dating their son. They didn’t even accept that they had a son, something that Illi hated about them. It didn’t take long for the young couple to decide that their dates were better off being held in Illi’s basement bedroom or outside.
“Illi!” Frank’s face blushed bright red as he saw the box. “Warn a guy first!”
Illi rolled her eyes. Frank tried to put on such a brave facade most of the time, acting the part of the brave punk boyfriend. He stood up to the jocks who made Illi’s time at school a living hell and paraded around the mall holding her hand and puffing his chest out like he was the luckiest man in the world. He really made her feel special, like she was the prettiest girl ever.
He was her first boyfriend, and now he was going to be her first. They’d fooled around before, but never gone further than just touching or using their mouths. She’d gotten to see Frank’s mouth stretched wide over her cock (hot), and gotten to bury two fingers into him until he came apart on her hand. She’d buried her face between his legs and licked into him until he sobbed, and she’d let him explore pressing a few fingers into her own hole and experience the pleasure that was having someone else finger her. They’d been toying around the idea of having penetrative sex for weeks now. Frank was anxious about it, probably more anxious than Illi herself was. She supposed that it made sense, seeing as he was going to be the one bottoming for this time at least.
Someday she hoped they could find Frankie a harness so that he could be on top, but as it currently stood neither of them were ready to go into a real sex store to shop for that kind of thing, and Illi had no idea where they would store it even if they did get one. Her mom was supportive of her identity, but she was too much of a snoop for Illi to trust having something like that in her room, and Frank’s mom would go crazy if she even thought that her son was using something like that. So for now they were going to do what they could.
“I did warn you.” Illi said, ripping at the plastic film that coated the box. She’d used a condom before, but never for the intended purpose. She remembered her mom giving her and Mikey some, all red in the face as she stumbled through an explanation of how to use them. Illi didn’t want to remember that moment, but she was ashamed to admit that she had used that condom on herself just to see how it felt. It made her feel a little less like a fish out of water as she finally got the package open. Looking up, she found that Frank was still looking at her with uncertain eyes.
She frowned, had he changed his mind? “Is something up?” She asked, her voice soft. “If you’re not ready we don’t have to do this. I know that you’re nervous.”
Frank shook his head, “No I’m ready.” His face was red as she made his way over to her bed, sitting down on it. “A little nervous I guess, but I trust you.”
That made Illi feel better. Once she had one of the condoms in her hand she walked over to sit on the bed next to him. “Just talk to me ok? We can go as slow as you need to.” Frank nodded. Reaching over, Illi took his hand. “Thanks for this by the way. I trust you too.”
That got her a smile. Illi figured that if they were going to do this, they’d better do it right. Leaning in, she pressed a light kiss to Frank’s lips just like she had a thousand times before. He lets her in easily, what started as a simple kiss quickly becomes something deeper. Illi tastes his tongue on her own, feels Frank leaning into her and the kiss. She dives back in for more, pulling Frank closer and closer until they are nearly chest to chest. They’d been in this place before, and it was easy for Illi to keep things going until they were horizontal in the bed with her leaning over Frank.
Her cock was already starting to harden under her skirt, and she was sure Frank could feel it even through his own pants. Illi moaned into the kiss - the thought of getting to feel him from the inside making her cock stiffen up to full hardness. She was so glad that he wanted this with her.
“Illi~” he whined, pulling back and panting heavily. Illi stared in awe at the strand of saliva that connected the two of them even though they were no longer actively kissing.
“You’re so pretty.” She said, enamoured with how gone he looked even though she hadn’t even touched him yet. “So pretty for me.”
He blushed deeper, canting his hips up so that his hipbone rubbed against her erection. “Illi!” he whined, “Come on, I wanna do it!”
She holds back a giggle, Frank gets so needy when they’re together like this. He puts on such a bold face when they are around other people, but when they’re alone he’s so soft and sweet like this.
“Paitence.” Illi shushed him, “Don’t rush it.”
Frank just rolled his eyes, “We’ve been waiting for weeks, I’m ready.” he thrust his hips up again, reminding Illi of what they were here to do.
“I know, but I wanna do this right.” Illi pointed out, it would be both of their first times and she wanted it to be special. Maybe she read too many romance books, but she had an idea of how she wanted this to go. She wants it to be good for Frank, she wants him to feel good, even if she knows that it might be a bit uncomfortable for him at first. She wanted this to feel right. She and Frank had been together for nearly a year and she could confidently say that he was the only person that she could imagine a future with. They’d talked about the idea of moving out together once they both graduated, even if Illi was a year above him. She would wait for him, even after she moved out for school. Maybe, once Frank graduated too, they could get an apartment and really start to live as themselves. She didn’t want anyone else but him, and she hoped that he felt the same way.
“You are doing this right, I just want you to do something.” Frank whined, “Touch me already!”
Illi can’t deny him that. She works the buttons of his shirt open, pulling it down his shoulders and pressing a few light kisses to the pale flesh that it reveals. He’s wearing his binder. Illi knows that he prefers to keep it on when they’re getting intimate, but she doesn’t think that it’s a good idea for his health alone. “Let’s get this off, ok?” She said gently, “You can borrow one of my shirts if you want.” Frank looks uncertain, but he lets her help him peel the article of clothing off. His breasts are so cute. Illi knows that he hates them, so she tries not to pay too much attention to them, but they sit so cutely on his chest.
“So pretty.” she said, tracing a finger down his sternum. “Pretty all over, and just for me.” Frank flushes.
“Illi.” He says, crossing his arms over his chest. “You know I’m sensitive there!” since he wore the binder all day she knew that his breasts got tender. As much as she wanted to tease him a little more by playing with his little pink nipples while she kneaded the soft flesh, she didn’t want to push him too far out of his comfort zone. Instead, she reluctantly gets up and grabs the first shirt she found - an old and faded batman shirt that she’d owned for ages - and throws it to Frank. He put it on, looking much more comfortable with it on, and it didn’t take long for him to start undoing his belt and pulling his pants down his legs.
“Come on Illi, get naked for me.” She rolled her eyes at how crass he was being, but did as he said. She figures that it was about time that the two of them got onto equal footing. She unbuttoned her shirt, pulling it off her shoulders and revealing the black bra she’d been wearing under her school uniform. Frank’s eyes went wide. He always liked it when she wore lingerie for him, her bra for today wasn’t as sexy as some of the others she’d worn, but Frank looked enamoured all the same. Illi felt a flush rising to her own cheeks, and as Illi unzipped her skirt and let it fall to the floor as Frank pulled his pants down his legs and revealed his boxers. In just a few seconds the two of them are left in their underwear. With a red face, Illi reaches behind her back, undoing her bra and letting it drop to the floor with little fanfare. She doesn’t have much by the way of breasts, but as she climbs back into the bed, Frank’s hands find them right away.
“So pretty, Illi.” Frank says, pulling her into him and kissing her deeply, “You really are the most beautiful girl in the world.” His hands roaming over the bare skin of her body. They run down her back, over her spine making her shiver. Frank’s not a patient man though, and soon enough his fingers are playing with the waistband of her panties, “Off, need these off.” He panted, “Need you now, Illi.”
Illi smiles, too far gone in lust to deny him. Her cock his hard, and the moment the panties are under her cock it springs free and slaps up against her tummy in a way that should be obscene but just makes her giggle instead. The hungry look in Frank’s eyes tells her that he feels the same. “Stay focused Frankie.” She teases.
“I wanna suck you.” He whined, already sounding breathless, “You know that I love sucking you.” Illi does. She knows that well, she loves how into blowjobs Frank gets. But that isn’t the goal for today.
“I know baby, but I wanna fuck you today.” She said, leaning in to kiss his nose. “As long as you’re still good with that, I’d like to give it a try.”
“I am.” Frank nodded, his dark hair flying against the pillow as he did. “I want you to fuck me.”
“Then you need to take these off.” Illi pulls at the elastic of his underwear. Frank goes bright red, but he shimmies his hips until they’re lost to the corner of her already-messy room. Her mouth starts to water as the sight of Frank’s pussy comes into focus. He’s so cute down there, with the little patch of black public hair framing his perfect cunt. Illi can’t resist the urge to reach down, placing her thumbs on either side of his labia and pulling to reveal him and make him squirm.
“Illi!” He whined, writhing against the sheets as she puts the entirety of his sex on full display. He always gets so self-conscious when she gets a good look at him. He’s already a little wet, and the musky smell that drifts off of him is enough to get Illi’s mouth watering. She really wants to eat him out, and honestly? Eating him out might make things easier for him when it comes to the main event of today. That thought alone is enough to have her meeting his gaze as she slowly lowered herself down, leaving no questions about what she was about to do. The first press of her tongue against his clit was enough to have him crying her name out loudly as his fingers tangled in her shoulder-length hair.
She loves his taste. Loves the musky scent and the way that his juices get all over her face. She’s sloppy with it, licking around his hole and kissing at his clit, making him whine. She wants him to be relaxed, wants to make him feel good. She pulls back just enough to ask him, “Can I use my fingers?”
“Yes, please Illi!” Frank whined, bucking his hips forward and practically fucking her face as he rubs against her and tries to gain more pleasure. Illi is careful as she reaches her hand down between them, gently circling his hole before deciding that he’s probably wet enough that it won’t hurt him for her to enter him now. She eases the first one in, relieved to find that he’s not too tight. The first time she’d fingered him, he’s been so tight that it had been almost uncomfortable for him. It took them some trial and error to figure out that Illi needed to stimulate his clit and spend some more time on foreplay to make sure that things were comfortable for him. Now, she’d learned his body enough that she could confidently finger him without causing him discomfort.
He humps up into her finger, and quickly she’s able to add another and then a third. She goes slowly enough to make sure that Frank isn’t in pain. Honestly, she’s a little bit worried about hurting him with sex. She’s heard so many horror stories from straight girls about their first time with their crappy boyfriends. She’s heard about girls that bled, about girls who were in so much pain that they cried and couldn’t find any pleasure, so many stories about girls who had horrible first-time experiences and she didn’t want any of that for Frank. She wanted this to be good for both of them.
“I’m ready, I promise that I’m ready.” He begged, “Get that condom in and get inside me.”
Those words made Illi’s cock jump, she wanted to get in him so. Damn. bad. But she reminded herself that she wanted to do this right. “Ok.” she said, pulling herself back enough to get up to her knees. She grabbed the forgotten condom, pulling it up and ripping the package open and sliding it onto her hard cock. She had a tube of lube as well - just for safety. Once she’s sure that the condom is good, she pours a little bit of lube onto her fingers, lowering them back down to Frank’s hole and pressing inside again. He’s still pretty open from the way that she’d fingered him earlier, but she wants to make sure that he’s slick enough that things feel good for him too.
“I’m pretty wet already.” Frank pointed out, “I think I’m good.”
“I just wanna make sure that it doesn’t hurt you.” Illi said, “You have to tell me if it hurts.”
“I will.” Frank promises her, “I promise you that I will yell at you if it hurts me, but I really want you to fuck me now.”
Illi has to admit - that sounds like a really good idea. So she positions herself above him, nudging the tip of her hard cock against his hole. This is it. She’s about to take her boyfriend's virginity and lose her own at the same time. This was it.
She started to press in.
She’s about to get the tip in without any issue, but after about an inch she feels Frank’s grip on her shoulders tighten. “You ok?” She asked, worry filling her chest.
“Yeah, I’m good.” Frank nodded, “You’re big.”
“Sorry.”
“Not a bad thing.” He smirked, though there was a tinge of uncertainty in his eyes, “You can keep going, but just be slow about it. I’m good though.”
Illi nods, trusting her boyfriend enough to know his limits. She presses in, the next few inches going in fine. Now that she’s more than halfway inside she can really feel what it’s like to be inside of him. He’s tight, and so warm. It’s different than when she’d been in his mouth, he feels so soft and slick even through the condom. “You feel so good.” she moaned, “You’re so tight Frankie.”
“That’s because you’re the first one to ever get me like this.” Frank pointed out, “I was all pure and innocent before you came along.” Illi’s dick twitches, the reminder going right to her dick. She must have made a face, since Frank gets a devilish look on his face. “You like that, don’t you?” he teased, like her dick wasn’t currently practically splitting him open. “You like the idea that you’re the only person to ever touch me like this. You like the fact that I was a total virgin before you got her hands on me.”
Illi has half a mind to remind her boyfriend that she was also a virgin before the two of them got together, but she’s too lost in the fantasy of being the only one to ever touch Frank like this. “Fuck.” She whines, pushing further and earning a high, whining noise from Frank as she finally pushes all the way inside of him. They’re fully connected now, their hips touching from how close they were. “So tight. So perfect. Fuck, Frankie, you’re perfect.”
“Illi!” He pants, “Fuck that’s a lot.”
“Hurts?” She asks, concern overwhelming her, but he just shakes his head.
“Feels good. Just give me a few seconds then you can keep moving.” Illi listens, just lying there inside of Frank while his breaths slow down and he grounds himself. It’s only a few seconds later until he gives her the go-ahead “You can move.”
Illi does, starting slowly as she starts to pull out a few inches before pressing back in. Each time her balls slap against his cunt she can hear the wet, slick noise from both the lube and Frank’s own lubrication. It’s hot, and she decides that she wants to hear this noise forever.
“Fuck.” she whines, “So good, Frankie.” She pushes in and out, pressing into him again and again, fucking into Frank and making him feel good if the little ‘ah, ah, ah’ noises that he lets out are anything to go by. “So good.” she compliments him, loving the way that he flushes brightly and goes hazy-eyed each time she praises him. “You’re perfect Frankie, absolutely perfect.”
He mewls, rocking his hips up into her to meet each thrust. “Illi!”
“You’re so perfect Frankie, you feel so good.” she was starting to get close, the thrumming in her lower stomach letting her know that she didn’t have much longer. She’s been hoping to hold out for longer for their first time, but Frank just felt so good. “I’m close.” She gasped, bringing her hand down to rub at Frank’s clit to try and bring him closer to his own peak.
“Cum for me Illi,” He said, making eye contact with her in a way that sends a chill down her spine. Fuck, the way that he says that only brings her closer to the edge and soon enough she’s cresting that wave and cumming while still inside of Frank. Fuck, the feeling of releasing while inside of him was like nothing she’d ever felt before. Thank god for condoms. She pants heavily, the thrust of her hips slowing down until she finally came to a halt, still inside of her boyfriend. He felt so good, but she was sure that it was starting to get uncomfortable for him so she reluctantly pulled out.
“Damn, Illi that was amazing.” Frank said. Illi knew that he still hadn’t gotten off yet, and she wanted to fix that ASAP.
“Let me take care of you.” She said, her hands finding his clit again and rubbing a gentle circle over the flesh. She could get him off like that, but then she remembered the heady taste of him on his tongue from earlier and changed her mind. “Wanna taste you.”
“Then do it,” Frank said, his hands finding her hair and pulling her down until her face was buried between his legs again. It didn’t take long of her lapping at him like a woman starving for him to be shaking around her and crying out as he came with her mouth on his cunt. “Fuck!” he called out, shaking as he collapsed back onto the bed, absolutely boneless.
Illi giggled, taking a moment to dispose of the condom before she laid back next to him on the bed, wrapping her arms around his slim waist and pulling him close to her. “What do you think?” she asked, anxious to be reassured that it had been as good for him as it was for her.
“I think that sex is amazing.” Frank said with a snort, “10/10 would do it again. Just give me a few days.”
A smile broke out across Illi’s face at the reassurance that he wasn’t in pain and had a good time. The thought of a round two was pretty appealing to her as well. She pulled him closer, laying her head on his chest as she did. “I’m glad. Thanks for sharing that with me.”
“There’s no one else that I would rather have shared that with.” Frank said, running his hands through her hair comfortingly. “I love you Illi.”
Her heart fluttered, it wasn’t the first time that he’d said it, but it makes her feel the same each time he does. “I love you too.”