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Pathfinding: An Adult Choose Your Own Adventure, Forty-fourth Entry

Popped a few cherries in his lifetime, and having been given pointers from windtooth, his father, on how to properly treat a first-timer, rufus forced himself to slow down a little, pressing his thick glans into that tense little permeation in imogen's hymen

Anal, Chipmunk, Choose Your Own Adventure, Creampie, F/F, Fantasy, Gnoll, Heat, Hippogryph, Hyena, Impregnation, M/F, M/M, Magic, Minotaur, Oral, Orca, Sixty-Nine, Teen, Teenagers, Tentacles, Unicorn, Vaginal, Voyeurism, Wolf

The Secret - Part 16

Our mom has me and my sisters visit a doctor four times a year, and he checks every time to make sure we still have intact hymens!

Bernese, Bernese Mountain Dog, Bisexual, Collie, Creampie, Cross-dressing, Cub, Cum Swallowing, Cum_internal, Daughter, Defloration, Dog, Exhibitionism, Face_slap, Feline, Female, First Time, French Kiss, Kissing, Kitty, Knot, Lesbian, Male, Oral, Panties, Samoyed, Sex toys, Son, Straight, Vibrator, Virgin, Virginity_loss, Voyeurism, boyfriend, fetish, girlfriend, sleepover, transvestite

The Heat (non-cub edit)

A couple of inches further down the shaft, he encountered resistance; he had bumped against her hymen.

Daughter, Explicit, Father, First Time, Forced, Heat, Incest, Knot, Rape, Sex, Short Story, Straight, Vaginal, Virgin

[COM-26] Fencehopping Folly

He felt her flesh squeeze him, tug at him, and seal him in past her surprisingly thick and durably hymen!

Anal, Anatomically Correct, Anthro, Anthro/feral, Barbs, Bestiality, Breaking the Hymen, Canine, Clit, Cock, Farm, Female, Female Ejaculation, Fence hopping, Fencehopping, Feral, Gender Shifting, Griffin, Gryphon, Knot, Knotting, M/F, M/M, Magic, Male, Messy, Night, Outdoors, Pussy, Quadruped, Size Difference, Squirt, Tie, Tied, Transformation, Tying, Vaginal, Virgin, Wolamute, Zoophilia, biped, hymen, mess, ranch, rural, shaft, sizeplay, wink

Hero new live

Anyway he made no further move allowing himself to spatter his seed up to her hymen.

Balls, Balto, Blowjob, Canine, Cum, Dog, Domination/Submission, Ejaculation, Feral, Jenna, Kissing, Love, M/F, Male/Female, Paw, Romance, Sex, Straight, Teasing, Virgin, Wolf Dog, Yiff

New Mates

He kept moving until he hit her hymen, stopping him from going any further. he knew what to do, but wasn't sure if he should. "are you really sure?" he asked her one more time.

Cum, First Time, Heat, Kissing, M/F, Mating, Pheromones, Pokemon, Shaymin, Vaporeon

Pound Puppies: Bright-Eyes 1st Heat

Whopper pressed forward until he reached her hymen. "are you ready bright-eyes?" asked whopper. "yes, just do it, i need it" bright-eyes screamed in anticipation. whopper wasted no time and break through the hymen.

1st time, Cub, Heat, M/F, Oral, Pound Puppies, Rule 34, Teaching, Vaginal, Virgin

Hermaphrodiary: Entry Six

I withdrew slowly, noticing some traces of her hymen on my shaft. "still alright?" she sighed in relief and looked up at me, a warm, loving look on her face now. "yeah, i'm fine. keep going."

Dog, F/Herm, Other/Herm, Otter, Virgin

The Cohia's Ch.1

Until he got to her hymen. it was then that he whispered to her that this was the part that was going to hurt and he drew back a little bit.

Age Play, Cub, Fox, M/F

The Alpha Male's new Pet Chapter 1

He growls hearing her scream in pain as he thrusts as hard as he can feeling a pop as his cock stiffen more knowing that pop was her hymen. "next time don't wonder off alone and this wont happen.

Forced, M/F, Male, Pet, Pup, Rape, Wolf, begining

The Midnight Discovery

"you looked confused when i said you broke your hymen, so..." he says as he sprays the water around on my crotch and inside my cunt, "i might as well explain. your hymen is...

C boi, C boy, C-boi, C-boy/male, C-boy/s, C-boy/solo, Cherry Popping, Cunt Boy, Cunt-boy, Cuntboi, Cuntboy, Cuntboy/male, Cuntboy/solo, Fennecfoxee, Fox, Incest, Intersex male, Intersex/Male, Intersexed male, M/solo, Male, Male/c-boy, Male/cuntboy, Male/intersex, Male/solo, Matthew, Matthew lupix, Midnight discovery, Oral, Oral Sex, Red Fox, Son/father, The midnight discovery, Vaginal, Vaginal Sex, Vaginal penetration, Virginity, Virginity Loss, Wolf, Xavier lupix, c-boy, father/son, intersex, intersexed, xavier

A Brother's Love

Mike took a breath, then thrust forward past her hymen, taking her virginity. the vixen cried out in pain as her hymen was torn, tears flowing down her eyes, which mike wiped away.

Abduction, Age Play, Fox, Incest, M/F, Snow Leopard