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The Breeder

Carefully i grabbed the base of my erection and turned it around slightly a few times to ensure spreading of the painkiller over her outer tunnel and hymen.

Feline, First Time, Human, M/F, Sci-Fi, Vaginal, Virgin

A Dragonair Tail

Feeling him against her hymen, and needing to be relieved, aria grabs dragonair by his body and shoves him in, breaking her hymen with the tip of his tail and making the water dragon growl mentally at her.

Bestiality, Impregnation, M/F, Pokemon, Tail Sex, dragonair

Hidden Feelings

He nodded at her, and pierced through her hymen. she let out a pain-filled scream, tears welling in her eyes. he didn't move, waiting for her to adapt. quite some time passed until she nodded at him to go on.

69, Human, Lucario, M/F, Pokemon, Pokephilia, Riolu, Vaginal

Prepared by Fate 2

He laughs maliciously at hir before roughly slamming his length into the girl, tearing hir hymen and making hir scream in pain.

Bat, Cub, Dragoness, Feline, Hermaphrodite, Male, Multiple Species, Rape, Violence, Virgin, Wolf, deflowering

Summer Heat – Chapter 13: Oh deer!

He heard her cry and felt his tip breach through her hymen and directly into her tunnel until she clamped down and made it too tight to push forward.

Beaver, Buffalo, Bunny, Cub, Deer, Elephant, Family, Female, Giraffe, Goat, Horse, Impregnation, Knot, Lioness, Lynx, M/F, Male, Mare, Oral, Pregnancy, School, Snow Leopard, Story Progression, Tigress, Vaginal, Vixen, Weasel, Wolf, Wolfess, Zebra

The Fallen Angel

He shifted forward a bit, working his footlong member into her up to the hymen, stretching her out enough that she began to bleed even before he broke the thing.

Angel, Bad Language, Deep Penetration, Demon, Domination/Submission, Double-Penetration, Impregnation, M/F, Rape, Violence

Lustful Lessons [Story+Art Collab]

With an abrupt shove, don's canine cock bent briefly before surging past his daughter's hymen. sierra gasped, looking up at her father, but his eyes were closed and his lips were curling.

Bad Parenting, Balls, Breeding, Canine Penis, Cave, Coyote, Cub, Cum, Cum Inflation, Cum in Vagina, Cum on body, Daughter, Desert, Dubcon, Dubious consent, Family, Father, Female, Feral, Humping, Incest, Knot, M/F, Male, Masturbation, Mating, Mother, Non-Anthro, Penis, Pup, Puppy, Scruffing, Snarling, Story, Tight, Vaginal, cum EVERYWHERE, cum inside, daughters, father/daughter, growling, mother/daughter, tight fit

A Hell Hounds Witch

“_it is i swear"_ she cried as she lifted her dress and spread her labia revealing her hymen.

Ball Worship, Canine, Halloween, Human, Knot, M/F, Magic, Oral, Snowballing, Vaginal, Virgin, Wolf, Young, hell hound

Summer Heat – Chapter 2: Incompetent Teaching

He had read that this was a hymen and that by something called 'mating' or 'sex' for the first time it was broken. sierah did not notice him gazing at the insides of her vagina for over a minute.

Family, Female, First Time, Heat, Incest, Knot, Lioness, M/F, Male, School, Story Progression, Vaginal, Wolf, Wolfess, babysitting

Jamie's Treatment

Desmond got up and gently placed his cock at the opening of jamie.she gasped at his touch.he pushed in,gliding his cock through her narrow tunnel.he hit her hymen and mentioned that there will be a little pain.she nodded and he pushed in,breaking her hymen

Kissing, Knot, Love, M/F, Oral, Teenagers, Wolf

Family's New Plaything - Chapter 1

As he pushed her further down on his cock, her hymen tore, her innocence, her virginity, ripped away in one act of lust from her father. it horrified her...she screamed.

Anal, Gang-Rape, Human, Human-Only, Incest, M/M/F, Oral, Rape, Underage, Vaginal, Virgin

Exile and his AI daughter

I brushed up against her hymen and stopped for a second. "seris this is going to hurt for a second," i told her as i backed up and quickly pushed through it. she winced ate the pain as i passed through her hymen.

Catgirl, Daughter, Father, Heat, Human, M/F, Sci-Fi, Semi-Incest, Space