Joseph just met her one day in the city when she got off work. He said he's staying a week to catch up with an old friend of his. They obviously find each other attractive, and long story short they hook up in his hotel room.

He's a pro at eating out, laving his tongue over either of her folds before getting her just wet enough to plunge his wet muscle inside and slip it back out with ease. Her moans are breathy and high as she clenches the sheets below her but at one point reaches out to grip his scalp. It stings, but that's how he knows he's doing a good job.

They do typical missionary too but that was the highlight.

Anyway they part ways... only to meet again at the restaurant her mom, Hailey, booked reservations for on the Sunnytime Crew Show Reunion!

Jo laughs in disbelief, telling Cloudy Bell Sue's actress that he and her daughter actually ran into each other before (leaving out the sex obviously) but on the inside he's panicking. He didn't cross a line with this, right? Would Hailey feel disrespected if she knew??

And May is just in a cold sweat, stomach churning the whole night and giving clipped responses. Hailey scolds her silently for her withdrawn behavior but tells everyone she's just shy and naturally introverted.

When two of the other actors leave, May decides to turn in early, with Joseph offering to ride her home. Hailey is skeptical since they technically just met and he's already doing favors, but she supposes he just wants to be nice, and he's always been like that!

There's quiet tension during the ride to her apartment, until midway May gets to asking how well her mom and Josepb know the other. He explains that she was what he considered one of his only real friends on the set of STC due to her being a bit older and familiar to the show business whereas he was just some guy making ends meet since running away from home. She picks up that way he describes it is almost wistful, and asks if he and her mom ever had a thing.

Joseph: "Oh...! No, no, no. Hailey was uh... too put together for someone like me. I-I'm pretty sure she saw me as a brother."

May: "Yikes."

Joseph: "Yeah. Real kick in the pants for someone with a crush. Anyway she was already with your dad, met him, sweet guy. And it all worked out."

May: "You don't...still like her or anything don't you because... well, that'd be a little..."

Joseph: "Nah. I do respect her a ton though. But I just..."

They pull up to the parking lot of her apartment. Joseph glances long ways at May, who looks back with an expression that betrays ... need. Yearning and a bit of lust. And oh, he knows better than anyone what it means to do all three. Their heated gazes obviously affect the other as breathing gets heavier and their bodies react to their imaginations.

Joseph's hand reaches out and clasps over hers on the armrest. "We gotta get outta this car and... let your mom know you got home safe."

She gives a crooked smile, "Do you mind walking me up?"

(Smut under the cut)

-

Anon 🧡✨

Hi Nonnie! Thanks for the question <3

I think it's one of those things that can be awkward or good depending on how it's written. @dameronscopilot really nailed it with cut the brakes and this headcanon. Both of those are Santiago Garcia fics and some personal faves of mine.

I personally have a longfic in the works for a Rainbow Six character with a DBF situation.

I think it depends on how it's written that determines whether or not it's awkward. If the reader character has a really good or close relationship with their dad, or maybe if the best friend was an "uncle" figure while the reader was growing up it may be a little more awkward than not. However, if there's some distance between the reader and the dad's best friend it might not be as awkward.