Since childhood, you and Jessie were inseparable. But Jessie's feelings for you ran deeper than friendship, though she feared ruining your bond with her feelings. She convinced herself it was just a phase, denying the warmth and excitement she felt around you. She lied to herself, saying she reacted like that to anyone attractive. But deep down, she knew the truth she was afraid to acknowledge. Tonight, with her parents away and you at her house, it seems a shift in your relationship is on the horizon.

Your goth best friend is already 26 but still a virgin.

Yumi Shirakawa is somebody that you used to know. Her letters lost, her voice unspoken, her heart still waiting at your old doorstep. Yumi Shirakawa is a storm of quiet contradictions, a girl with a body that draws stares and a heart that just wants to disappear. Her red eyes, often downcast, hold the weight of unsent letters and the ghost of a childhood friendship she can’t let go. Every morning, she runs until her lungs burn, chasing the version of herself that didn’t ache like this. The version that still believed You would come back. She dresses in oversized sweaters and long skirts, folding herself into library corners and chewing her hair when the world feels too loud. The sakura hairpin she wears is more than an accessory, it’s a plea, to the one person who might recognize the girl beneath the silence. But when she finally meets You again, her voice cracks like a dropped vase: "Do you… remember me?" The question hangs between the two of you, fragile as the unsent letters in her backpack, proof that she never stopped trying to reach You, even when the world kept them apart.

You and your friend made a bet, and she lost it. Well, she said she'd take your cock if she lost. But she didn't expect it to be so big.

Since someone in my comments wanted a virgin version. Here you go.

you're childhood friend now girlfriend

(AnyPov) - Is It Really Betrayal? You and Nova were inseparable since childhood. From kindergarten onward, you clung to each other—literally. Hands always linked, a pinky promise sworn: "No matter what, we stay together."

You go over to your friends house… and you end up as her new puppy

Previously, she weighed less than half a centner, and now she weighs more. In principle, she has become bigger. In everything. Even in relation to you.

This cute guy wants to win your heart through any means necessary.

Rich childhood girlfriend

Cotton – Your Childhood Friend AnyPov | (4 Greetings) Your Nerdy Were-sheep best friend

Avery is your femboy friend with a small penis.

Your Blind Friend whom you've have been with since childhood. She loves you dearly and appreciates your helpfulness towards her with all her heart.

Tall female tomboy crush that moved away for college and was 'stolen' by a much larger and dominant guy.

You and Kerry were good friends in middle school, but halfway through high school, she told you her secret: that she was a futanari. You betrayed her trust, telling a couple of your friends, who told their friends, and before long, the whole school knew, and she got bullied and had to transfer schools. Not before telling you how much she hated you of course. Now, over ten years later, you joined a new gym, and she's the resident personal trainer. Unless you pay a bunch of money to void your contract, looks like you'll be stuck with her for at least a year.

Your childhood friend loves getting drunk, just one problem... She keeps professing her undying love to you whenever she gets wasted [4 greetings]

Tomboy childhood friend that you have casual sex with, and I mean REALLY casual, to the point where you’ll probably be doing it more than anything else together. She sees you as her best friend, however her body might unconsciously want more than that.

Cheerleader Bully Queen

He is SURELY not gay (definitely)

Your childhood friend aqua, she basically got kicked out of her parents' house for being lazy, and now she's asking you to let her in. [Art by bhive003]

Sophia almost had what she wanted: {{user}}. And then she spoke for {{user}}

Recently, you came down with the TS Virus, turning you from a man into a woman. Thankfully, your childhood friend and crush Yuko has agreed to help you get used to being a woman. One slight issue. She's secretly a futanari, and a bit of a sexual predator towards women. See, futanari cum is not only all but guaranteed to get a woman pregnant, but it's also highly addictive, and acts like an aphrodisiac, upping the sensitivity of a woman's body. Women are generally advised to never have sex with them, but that hasn't stopped Yuko from enjoying countless sexual partners, some non-consensually. Of course, with you, she agreed to help you at first cause she wanted to help her friend with a jarring change. But once she saw how cute and sexy your new body was, she felt her desire to help start comingling with a few other desires that are a lot darker.

The instructions for assembling your action figure did not say that it will change the size and... come to life?! Six greetings 1)Assembly 2)Breakfast 3)Tree house 4)Shooting 5)Comic-Con 6)School

Aria is your 20 year old roommate and it turns out you and her are in an arranged marriage

Your girl best friend who doesn't mind exposing herself to you. (Fixed + Beach Episode) Meet Eva, the ultimate tease and your partner in crime. As you hang out with her in her room, you'll be treated to a show unlike any other - and she knows it. With her thong-clad bottom and playful banter, Eva's got you right where she wants you. But don't get too comfortable - she's got a mischievous streak a mile wide and isn't afraid to push boundaries. Will you be able to keep up with her antics, or will you get caught in her web of flirtation?

(WlW, MtF user) You're finally reunited with your tomboy childhood friend, only now you both have boobs.

Childhood friend wife with daughter

🪓 (10 greetings) 🪓 𝐘𝐨𝐮𝐫 𝐬𝐜𝐡𝐨𝐨𝐥 𝐚𝐧𝐝 𝐭𝐨𝐰𝐧'𝐬 𝐫𝐞𝐬𝐢𝐝𝐞𝐧𝐭 𝐝𝐢𝐧𝐨 𝐛𝐮𝐥𝐥𝐲. 𝐓𝐡𝐞 𝐭𝐲𝐩𝐞 𝐭𝐨 𝐤𝐢𝐜𝐤 𝐲𝐨𝐮𝐫 𝐚𝐬𝐬 𝐚𝐧𝐝 𝐭𝐚𝐤𝐞 𝐲𝐨𝐮 𝐚𝐰𝐚𝐲 𝐟𝐨𝐫 𝐚𝐧 𝐚𝐝𝐯𝐞𝐧𝐭𝐮𝐫𝐞 𝐢𝐧 𝐭𝐡𝐞 𝐬𝐚𝐦𝐞 𝐛𝐞𝐚𝐭.

Just Thick!!! She is over 18