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My Young Mistress

Sliding myself further in, i found her maidenhead and looked at her. she told me to do it. there was no going back if i did but she told me she didn't care.

First Time, Foreplay, Fox, Human, M/F, Master/Slave, Vaginal, Voyeurism

Three Little Nobles and the Big Bad Wolfen

For an instant, her maidenhead held, and then there was a burst of pain, making the poor little noble cry out and struggle against the strong grip and stout ropes holding her still.

Famous Literary Characters, Human, Impregnation, M/F, NC, Slavery, Teenagers, Virgin, Wolf

Dragon-soiled Priestess [Commission]

Her fingers had, of course, stopped once they encountered her maidenhead, but in her mind her lover didn’t.

Bestiality, Dragon, Feral, Heat, Impregnation, Kobold, Non-Consensual, Size Difference

A Child's Darkness, Chapter 2: A Blood Auction

Her gut felt like someone had punched it in, and then left a cinderblock there as she struggled to breathe past the horrific, ripping, shredding feeling of her maidenhead being ripped away.

Auction, Blowjob, Bondage, Cub, Desperation, Drugs, Exhibitionism, Facial, Fellatio, Fingering, Fondling, Fox, Humiliation, Incest, Kitsune, Knot, M/F, Nudity, Oral, Pain, Planning, Public, Size Difference, Vaginal, Virgin, Virginity, Vulpine, plotting

Sating the Beast

A low growl rumbled from its direction, and shadi shivered, her vulnerability and exposure making her blush with humiliation at the thought of being this beast's plaything for her heat, the thought of her maidenhead being broken by this... this beast

Amasii lion, Bestiality, Bondage, Feline, Feral, First Time, Forced, Forest, Fox, Heat, Impregnation, Keynari, Knot, M/F, Public, Rape, Tie, Underage, Virgin, Vulpine

Mind your own business

** **he slipped a finger into the warm, wet valley between her legs, and while she gasped and muffled, he explored and found she was indeed a virgin; her maidenhead was intact.

First Time, Fox, Gideon, Judy Hopps, Pain, Rabbit, Rape, Short Story, Underage, Zootopia

Ignoble Fates [Commission]

She was sure the girl's maidenhead had been claimed already, but judging by the groans of her master she was still too tight to comfortably take a kos member.

Bull, Canine, Dark, F/F/F, Humiliation, Impregnation, Jackal, Knot, M/F, M/M/F, Pregnant, Punishment, Rape, Slavery, Young

Illian: Ruff Days

Eve gave a yelp of surprise as her maidenhead ripped, causing her to bleed.

Bunny, Canine, M/F, Story Progression

Werewolf Story

She was still a virgin though, and the thought of losing her maidenhead to this monster scared her into running again. as she crashed through the brush and briers, her dress slowly was torn away until she was left wearing only her bodice.

Cum, Knot, M/F, Oral, Virgin, Werewolf

The adventures of Cearul - Attack of the Northmen

I want you inside me, i want you to take my maidenhead and make me a woman." "ok," cearul said. "roll over on your stomach then, and bring your knees up towards your chest," cearul instructed her.

Knot, M/F, Oral, Sex, Tie, Vaginal, Virgin, Werewolf

Pay backs Bitch...

The little fox smirked, as he rammed his bone against the wolf's maidenhead! brutally pushing through it, as he buried his quickly swelling knot in the wolf! kurrgurr struggle violently then, trying to pull away!

Athlete, Bisexual, Fox, Gender Shifting, Humiliation, Molesting, Wolf

Nightly Prowl: Part.1, Finding a Prey

Ehasaru screamed from the pain as a little blood from her maidenhead ran out of her womanhood and down towards her ass.

M/F, Rape, Vaginal, Vampire, Werewolf