Crossing the Line with my Best Friend: Straight to Gay First Time MM

by Ash St. James

“It’s okay, Matty. If what I said has you curious, you can just say so.”

Matty

While venting about my latest dating disaster, my best friend let slip exactly what he wanted in a hookup. How good it felt when someone got on their knees for him, knowing exactly how to drive him wild.

My body betrayed me.
I shouldn’t have wanted him.
I was supposed to be straight.

But over the next week, every woman I met faded into the background. All I could think about was Jesse. His hands, his touch, the way he made me ache in ways I couldn’t name.

What if I was wrong about how I felt and lost my best friend?
What if he rejected me since I didn’t have the experience he wanted?

Stand alone, M/M, best friends to lovers erotica with an HEA.

***See Content Note

Genres: M M Romance, Novella, Romance, Erotica, Contemporary

49 pages, Kindle Edition

Published May 18, 2026

Reviews

[James Hill · Rating 4 out of 5]

Crossing

I will give this story a 4\5. This short story is about a straight man decides he want to be with his gay best friend. It is interesting. I read short erotica sometimes when I finish heavy stories. This is short and sweet.

[SplatterGunk · Rating 3 out of 5]

Alternative cover is: “Exploring With My Best Friend,” but the book is still the same.

This was surprisingly wholesome and cozy. It wasn’t as steamy as I was hoping, but to be fair, the sexual tension between the characters and the chemistry made up for that, so really I can’t be too upset.

[Mary · Rating 5 out of 5]

This was rather wholesome for being a smut snack

[Stephanie · Rating 4 out of 5]

Short, smutty, and sweet. A very quick, little palate cleanser. Jesse and Matty are so cute together.