Stretch My Hole: A Tale of Reluctant Feminization (Patreon)

Eugene’s friend, Patton, has been depressed since the sudden passing of his brother. His depression is so bad that he attempts suicide, landing him in the hospital for many days. During Patton’s stay in the hospital, while on a combination of strong drugs, he tells Eugene his secret: that he’s never been in bed with a woman.

Now, Eugene is determined to make his friend’s dream come true, to make him happy so he doesn’t try to hurt himself again. He’s willing to go to great lengths, even ready to pay a girl to do the deed. But Eugene can find nobody, except for a girl named Astra, who is willing to go on a date with Patton, but she’s not willing to go that extra mile. So Eugene is ready to take over the rest. The plan is for Astra to get Patton into a dark bedroom, then she’ll make the switch with a dolled up Eugene. It’s a sacrifice he’s willing to make for his best friend—but it’s a sacrifice that comes with consequences.