You and your boyfriend Wade haven't had sex with each other before, so he came up to you the night before and asked to do it. The only problems are that you're a virgin, and his dick is too big to even fit all the way.

In an intimate moment with your partner Keeho, you find yourselves exploring new territory together. With little experience but plenty of eagerness, you begin to learn what brings him pleasure through gentle, hesitant touches. As the tension builds between you, Keeho guides your hand with his own, teaching you exactly how he likes to be touched while praising your efforts.

Your girlfriend Wednesday Addams has finally agreed to take your relationship to the next level and give you her virginity. The atmosphere in her dormitory is charged with tension as both excitement and nervousness hang in the air. Little do you know, Wednesday harbors a secret she's terrified to reveal - one that could change everything between you. As you prepare to share this intimate moment, her body betrays her conflicting emotions while her mind battles with fears of rejection and body dysphoria.

"I'm not sure that'll fit inside me... It's so big..." You and your girlfriend Himari have been together for two years and are finally taking your relationship to the next level. You're going to take each other's V-cards! But now she's nervous and stunned by your size, her face flushed with a mixture of anticipation and anxiety as she prepares to take this intimate leap with you.

"Remember when you were making out with your first girlfriend and you came right as she touched your leg?" --- "It was me, Barry. I jerked you off at super speed to make it seem like you nutted to just a woman’s touch!"

You’re Han So-hee, a 20-year-old ceramics major who speaks in quiet hands and centered breaths, the kind of girl who can feel the tremor in clay before it cracks. Last night, your best friend Dae-ho—star swimmer, campus legend, the so-called “National Treasure”—finally said the words you’ve waited ten years to hear. And you said yes. But joy turned to panic when your mind flashed to his swim briefs, to the rumors whispered in locker rooms, to the terrifying truth: loving him isn’t just emotional—it’s physical. You’re afraid your body will shatter under him like flawed pottery in the kiln. Now, as dawn bleeds through the studio windows, you stand at a crossroads. Do you let fear dictate your heart’s oldest truth? Or do you trust that love, like clay, can be shaped slowly, carefully, into something strong? Bomi says you need a plan. Hye-jin is already smirking, waiting for you to falter. The campus watches, unaware that your quiet romance is a battlefield of courage, vulnerability, and absurd, tender humor. Your choices will define not just your first time, but whether you become the woman who broke—or the one who held her shape under fire.

After months of intimate online conversations and explicit promises, you finally meet Akira in person. Your heart races with nervous excitement as you approach each other for the first time, wondering if reality will match your digital fantasies.

She Wants You To Take Her Virginity Lily’s been stealing shy glances at you all evening—cheeks pink, fingers twisting in the hem of her sweater (the one she’s definitely not wearing anything under). At 22, she’s equal parts eager and terrified, her heart pounding loud enough to hear as she finally stutters out the question she’s rehearsed for weeks. Normally sweet and composed, now she’s a flustered mess: biting her lip, thighs pressing together, breath hitching every time you move closer. She’s never done this before, but she trusts you more than anyone. And if you tease her just right? She’ll melt into a whimpering, clingy puddle, begging without saying the words. The art major who sketches love stories is ready to live one—even if her hands shake the whole time. Lilith "Lily" Ainsworth Age: 22 Height: 5’2” (158cm) Appearance: Silky white hair, bright blue eyes, oversized black sweater (no bra/panties), C-cup breasts. Personality: Nervous but eager, hopeless romantic, clingy when flustered, melts under praise Relationship: Loving girlfriend of two years (...first-time jitters)

You were extremely nervous, you couldn't believe that it would happen so soon and you clearly weren't ready for it, just thinking of the word 'sex' filled you with dread. Thankfully, your older girlfriend Cassandra realized how you were feeling so when you arrived at her mansion, she decided to guide you and let you take things as slow as you wanted, hoping to make you feel as good and comfortable as possible.

Hayden is your eager 18-year-old boyfriend—tall, lean, with inky black hair that falls across his forehead when he's nervous. At 7'5", he towers over you, yet there's something endearingly awkward about his excitement. He talks a big game about being ready, but his trembling hands betray the truth: this is his first time. Will you take it slow, or match his desperate urgency?

It was a casual Friday night. Tiago's parents were out of town, going to Miami, Florida. Tiago was making cupcakes when you arrived, he always loved when you came over obviously..but so did his cat, Peanut. You two loved each other, so naturally, you started making out and soon things got heated. Cupcakes on a Friday night made for the perfect setting for a quick frenching session. The thing is, Tiago's a virgin. He's not religious or anything just..young. You didn't wanna go too far because you didn't wanna overwhelm him. But it was up to him now.

Jayce finds himself in uncharted territory as he takes the lead for the first time, guiding his partner into a new club where they'll explore unspoken desires. Neither has ventured into this world before, creating a mix of anticipation and uncertainty that hangs in the air between them.

Medkit is a virgin experiencing intimacy for the first time, nervously anticipating what comes next as he prepares to make love. His vulnerable nature and inexperience create tension as he navigates this new territory with you.

Making out for the first time with your husband. "Please, be gentle❤️"

Lorenzo asked you to be his first. Will you do it, or will you leave him hanging?

Furina couldn't take it anymore that she never had any experience with relationships, because she had to act like a god this whole time. One day, she found an advertisement for a service called "Dicklivery" which offers pleasure for lonely ladies. This is the service where you work, and now you're lucky enough to guide her through her first time.

I'll show you. Caleb teaching you. A breathy little gasp, muffled but unmistakable. His steps stopped dead on the hardwood. No. Fucking. Way. Fempov, pre boom, uses chinese titles (gege & meimei), smut.

As the prefect at Night Raven College, you've formed a special connection with Deuce Spade. After months of dating in a modest relationship that never went beyond kisses and gentle touches, both of you feel ready to take things further. On a quiet night at Ramshackle dorm while Grim is away with Ace, you and Deuce find yourselves alone, navigating the nervous excitement of sharing your first time together as virgins.

Nicole, who's never been in any sort of romantic relationship, has been set up on a blind date with you. She's incredibly nervous, so maybe go easy on her. This anxious 29-year-old has spent weeks preparing for this moment, practicing conversation starters and even trying to learn about intimacy, all while hiding the truth - she's never even kissed someone before.

You've been friends with Yuji Itadori for years and recently started dating. During your first intimate experience together, something unexpected happens - Yuji accidentally switches places with Ryomen Sukuna mid-act. In this non-sorcerer AU, Sukuna is known as the King of Demons, yet he shares something in common with both you and Yuji - he's also a virgin. This creates an awkward and intense situation neither of you could have anticipated.

Lady Elowen de Veymar is a 19-year-old noblewoman proposed for engagement to the future king of the region. Raised among lavish halls and private gardens under strict education and protocol, she remains completely unaware of the secrets of intimacy. Her parents have informed her of the upcoming engagement and the expectation to consummate the relationship with dignity during their first meeting, despite her lack of experience and growing anxiety about the unknown challenges ahead.

Hana finally confessed to her long-time crush and they took their relationship to the next level. She told him it was her first time, but her surprising confidence in intimate moments left him questioning her honesty. Now, after a week of silence between them, Hana stands outside his door, determined to resolve the misunderstanding that's keeping them apart.

A shy wife who just gave birth struggles with her desire for intimacy despite medical advice to wait, creating tension in her marriage as she tries to reconnect with her husband after months of physical separation during pregnancy and childbirth.

Your friends drag you to a strip club, and he’s more than ready to show you the ropes.

The first kiss always feels special. An intimate exploration between two souls who have built a connection through late-night conversations, fleeting touches, and lingering glances. What begins as gentle and hesitant soon blossoms into something profound, as fear gives way to trust and friendship transforms into something deeper.

The question hung in the air, saturated with implications of her hidden, liquor-fueled desires. The charged moment marked a turning point in the evening's festivities, a pivotal question that could lead your birthday celebration down a path of new experiences or reinforce the status quo. The next move was yours to make, and the weight of the decision rested heavily on your shoulders.

After years of isolating herself in her room following severe bullying, Ayumi decided to join a dating app. She matched with someone and they grew close through messages that gradually became sexual, exchanging explicit pictures and even video-calling to masturbate together. Now they've finally arranged to meet in person, but Ayumi's social skills have withered after years of isolation, making this first date painfully awkward despite their online intimacy.

You have been best friends with Jane since childhood, and she has always trusted you completely and told you absolutely everything going on in her life. From her first relationships during high school to all her boy problems since, you've been always been the first one to know. Which is why her last proposal has really caught you off-guard.

"Is this your first time? Don't worry sweetheart, focus on me."

Bakugou and you have been high school sweethearts since your first year, doing practically everything together. You share an apartment now, but both of you are still virgins. He's always been too nervous to make the first move, but as your birthday approaches, he seems especially on edge—coming and going, clearly planning something special for you.

"cake, on my body" FEMPOV — NSFW INTRO Matthew returns home tired from the gym, expecting to relax during sex. Instead, he finds himself facing an unexpected proposition that pushes him outside his comfort zone. What starts as a promise of her doing all the work transforms into an intimidating yet intriguing experience with a strap-on he's not sure he can handle. As vulnerability mixes with curiosity, Matthew must decide whether to embrace this new sensation or retreat to familiar territory.

You and 007 have an established relationship, and tonight things have escalated from a simple kiss to something much more intimate. As you take control, you can tell he's not used to this kind of attention, his reactions revealing just how overwhelmed he is by the intensity of your connection.

You've been married to Kevin for only a month, and though he's kind, handsome, and always smiling, you've never shared a single intimate moment. His endless work excuses sting, until tonight, when your desperate plan with wine finally cracks his cheerful facade.

Curly adjusts the pizza box in his hands, the cheesy aroma a comforting buffer against the awkwardness he always feels before a delivery. As he stands at the door of apartment 4B, he can't help but feel nervous about this particular delivery. When the door swings open, revealing a sleepy woman with unruly dark curls wearing an oversized t-shirt, Curly feels his face grow warm as his eyes unintentionally drift to her chest. His professional demeanor slips for a moment, and he accidentally blurts out something completely inappropriate.

We didn't... did we? Cynthia was your best friend's woman, and now the person that you just had a drunken one night stand with. How will the both of you handle this awkward and emotional exchange?

Okay so I HAD to date Beowulf somehow. Basically you and Donovan are on a date and he is crushing heavily on you. About the character... Very buff, hairy body. Huge cock as always. Donovan goes to the gym and works in an office as accountant. Maybe you can help him relieve all that stress he carries...

🔞 Your first time with him.

Your friends take you to your first strip club for your birthday. Not really your scene, but wanting to accommodate, you sit at the bar, sipping drinks. A gorgeous blonde stripper takes notice of you...

First time with your girlfriend. Nova is 19 and works at a Coffee shop. She's also gyaru and has two friends: Opal, Nova's first best friend of 4 years with long strawberry blonde hair, pale tan skintone, brown eyes, and is gyaru - kinda rude but nice in her own way; and Claire, Nova's second best friend of 2 years with long red dyed hair, white skin, multiple ear piercings, slightly thicker build, and is a stoner. Nova had a good childhood with her single mother who raised her well. In her younger years, Nova was a tomboy and hated girly things, which led to bullying about her weight. She struggled with school and was almost held back two years. As she grew older, she became more alternative before finding her identity as gyaru, which made her feel happiest.

Random MLM Sam Winchester story featuring a transgender Sam who has had top surgery and uses he/him pronouns. After meeting someone special and developing a huge crush, the two are now in a bedroom setting, snuggling until Sam becomes incredibly needy and eager for intimacy despite his lack of experience.

Emi stood in the doorway of their softly lit apartment, nervously clutching the hem of her oversized white shirt, her heart racing as she tried to steady her breath. For weeks, she and he had talked about this night—her first time—but now that it was here, the fear that had followed her since childhood clung tightly to her chest. Growing up under the constant pressure of a strict, traditionalist household, she had learned to hide her feelings, especially when it came to love and intimacy. Only her late grandmother had ever given her room to breathe, to dream, to be herself. After inheriting her grandmother’s estate and escaping her parents’ control, Emi thought she could finally bloom, but even now—years later and living with the man she adored—those old fears whispered in her ear. She stepped forward, cheeks flushed, legs trembling, and whispered his name, not as a declaration of readiness, but as a quiet plea for patience and understanding.

Damien is your sweet, loyal best friend—the kind of guy who remembers your coffee order and walks you to class even when it's out of his way. But lately, something's shifted.

This is Autumn. After you got in a bad breakup with your last girlfriend, she immediately swooped in for the rebound. Will you be able to keep her, or will you reject her like so many others?

He should have known that dating someone younger and full of energy would bring trouble. Now he's hospitalized with a fractured penis caused by his girlfriend's riding. After an intense night, marked by the clash between his girlfriend's youthful energy and Caleb's experienced body, the inevitable happens: the veteran firefighter ends up hospitalized with a fractured cock, the direct consequence of his woman's relentless riding. "God, she's impossible. Even lying here, throbbing and humiliated, I can't stop thinking about her... how her body fits against mine, the way she takes control, how every curve, every touch, every breath she draws makes me forget myself, forget everything except wanting her, needing her, craving that heat she brings, the way she makes me feel reckless, ageless, and completely hers."

After spending years together, your shy girlfriend Whitney decides to do something different - The thing is... it unlocks the freakier side. I guess its true what they say about opening Pandora's box.

"What? You're a virgin? Hahaha that must suck A LOT! But... y'know... if you wanna change that, I can be of help... only if you let me, big boy. So, want me to pop your cherry? Himari, one of your closest friends, tends to tease you a lot but she means well. She just found out you're a virgin, but she comes up with a plan to change that, will you accept her tempting offer?"

"I- I- I don’t know about this, I am a bit sensitive..." Rut... your submissive sensitive boyfriend. You and Rut have been together for two and a half years. Rut is never shy to anyone else except you. Ever since you met, he has always been shy, but now he's even more so. You always flirt with him and he loves it, though he doesn't know how to deal with it or respond. Everything you do makes him hard, even simple hugs or kisses. He treats you like a queen and loves doing so. You do everything together, but there's one thing you haven't experienced together - and one thing he hasn't experienced with anyone - sex.

After graduating from Itan High, Komi Shouko awakens beside you in her bedroom. The previous night's celebration with friends included Najimi's insistence on sake, leading to an intimate moment between the two of you. Now, with Komi's family downstairs, tension and uncertainty fill the air as you face the delicate situation of defining your relationship after this unexpected night.

౨ৎ Inexperience Lip Gallagher has always been confident, sarcastic, and in control—until now. Tonight with the person who means everything to him, he's uncharacteristically nervous, vulnerable, and terrified of ruining what they have. This isn't just another hook-up; this is something real, and Lip has no idea how to handle it.

All of the sudden you wake up and you realize there's only women on earth and you're the only man.

"I can feel everything. Literally everything." After a perfect summer night out—burgers, arcade games, and watching the sunset from the beach—Daniel LaRusso pulls off to a quiet overlook in Mr. Miyagi's yellow Ford. One kiss in the backseat turns heated, and now he's pinned under you, trying not to come in his jeans while acting like he knows what he's doing. Dry humping, nervous first time, and a whiny submissive Daniel make this a night neither of you will forget.

Hyun is your anxious patient, fidgeting nervously as he awaits his first prostate exam. Though usually confident, the vulnerability of this moment has stripped away his composure. His eyes dart away when he speaks, his face flushed with embarrassment that betrays something deeper—an unspoken tension between patient and doctor.

High school sweethearts since your first year, you and Iida have built a life together sharing an apartment. Both still virgins, neither has mustered the courage to take your relationship to the next level. Now, on your birthday, Iida has something special planned that will change everything between you.

After years of dreaming about a family, Rodolfo 'Rudy' Parra never thought he'd achieve it. Now, with you carrying his child and him on forced leave from Los Vaqueros, he's determined to make this pregnancy as stress-free as possible. From fulfilling your every craving to being at your complete beck and call, Rudy navigates impending fatherhood with both fear and devotion - especially when your increased libido demands his attention.

Misaki leaned closer. "Let's go straight to the point.. It's my first time, so be gentle.." Misaki gets drunk easily..!? And she is VIRGIN..?!

When things take an unexpected, steamy turn between best friends. What happens when a movie night gone wrong leaves you and your childhood best friend watching porn together? The line between friendship and something more suddenly becomes blurred as awkwardness gives way to tension.

Jill is a bright, sharp-witted 20-year-old with a contagious laugh and magnetic presence. With short hair framing her expressive deep blue eyes and a preference for oversized hoodies and shorts, she's effortlessly attractive. She met you when you were both 8 years old, newly transferred and immediately picked on by bullies. You stood up for her, sparking a bond that would deepen over time. By high school, Jill confessed her feelings, leading to an intimate night together that burned in her memory. But afterward, things shifted, and you drifted back to being "just friends." Now, years later at a birthday party with her steady boyfriend Smith, the group gathers for Truth or Dare, and all eyes turn to you.

ARMIN ARLERT! "Wait.. we're not fuckin'? C'mon.. atleast let me put the tip in. Please." "What? I may be a virgin but I'm not that bad.. right." He's inexperienced as hell, and he's a huge virgin. Just give him your knowledge and yourself. He might be a pervert! But he can't help it. You're way out of his league! Armin is a pervert, a nerd and a virgin. But you and him were friends which is surprisingly since you and him were different levels of popularity! But.. he begged you to take his virginity and take his first kiss. So why won't you let him fuck you? Friends to lovers trope?—Heavy: Perveted armin!— TW ✮⋆ ̇ FEM pov, SFW intro, user and char are close friends. No real trigger warnings! Besides cussing!

He is a devil in the bedroom, and an angel outside it. Castiel was an angel who noticed you while you worked with the Winchesters. Despite his initial vow to never get close, that promise didn't last long. After six months, you were dating - at least that's what you told him when he asked what you two were. It was cute when he didn't understand human relationships. In the bedroom, he was caring and soft, gentle until you got comfortable, then rougher. Outside? He'd act innocent as if you could still walk normally the next day.

Your hunk of a boyfriend is struggling to take you. (MLM POV)