Woman's Best Friend
"the pain comes when your maidenhead breaks, so if there is no maidenhead, there will be no pain from losing your virginity." he moved back, looking her in the eyes again. "did you feel any pain?"
The Stuff of Legends and Fables
She could tell, from the discomfort, that he was attemptingto stretch her maidenhead. all she really wanted him to do was to rupture itand take her. but he was so measured, so kind, and it was frustrating.
The Journey of Chloe Wintermane
"i will be sure not to break your maidenhead, but poor snowfur does not know how empty she is, yes! pretty puppy, this lovely wet slit between your legs is meant to be filled, you know that much do you not?"
Incident on Safari
With a simple, deft movement, nala then teased the finger of the hand that had just removed rianna's maidenhead, still slick with the human girl's juices, against her snug young anus.
The Windsar Adventures Part 6: Old Debts and New Leads
This sensation quickly passed as the wolfen slowly, carefully, squeezed his smooth tongue inside of her, getting a good, long taste of her intoxicatingly sweet, virgin inner places - for flintclaw had carefully stretched her maidenhead with his fingers
Epilogue Final
It started with her winking pussy and a paw pulling it open to show her maidenhead and her pearl. from the winking and the amount of juices it was clear that the girl was in heat now and in the upper corner it even said, "the first heat.".
Shadow-Moon Clan
The half-breed's breathe came in shallow pants and hisses, ramming his shaft knot-deep into her, blood from the tigress's maidenhead dripping silently upon the sheets.
Coming of Age
He thrust like mad, not even feeling the resistance as her maidenhead gave way to his lupine shaft. like an inexperienced cub, ario flopped around on n'hela, who cried for him to stop, but knew he could not help himself.
The Ritual Begins
There was an unpleasant stretchy feeling throughout the length of her birth-canal as her young body sought to accumulate the fully engorged girth of a full-grown stallion, but other than the initial jab of pain from having her maidenhead broken, and minor
Phade and Natalie - Have Faith
 while she was distracted by natalie's kiss, i gave a long, hard thrust.â i felt an obstruction within faith, her maidenhead, which stretched, flexed, and finally tore, granting me admission to her deepest reaches.â faith cried out in pain
Six Ribbons
It is my maidenhead... it's expected. every mare feels some pain as it is broken their first time... but it will soon feel good." she kissed him to reassure him, as she adjusted to the feel. it had hurt in truth, but less than she feared.
Praxeum Jewel of Mercy
Coco pushed her hips forward, driving every last inch o that thick, long black meat into the girl, ripping through her maidenhead if it was still there in an instant.