I need Tombur fingering PLEASSEEE? IF THATS OKAY??
The thing is, Tommy is absolutely terrified of getting fingered. Trying to convince him that it's completely safe and actually pretty normal for guys to do this together feels a lot like Wilbur trying to get an anxious dog to not bite.
And Tommy looks about ready to snap, wringing out his sweaty palms as he squirms in his seat on the end of Wilbur's bed. It would almost be funny, if Wilbur had a bit less pity for the kid.
"We don't have to do this, you know." Wilbur states the obvious as he pulls his jumper off, tossing it to the floor as he takes a seat next to Tommy. The boy flinches when their knees bump, and Wilbur can't tell if he wants to roll his eyes out of fondness or true annoyance.
"I know that." Tommy replies immediately, but it comes out all wrong. He sounds far too stiff. His boyfriend has never been good about hiding the way he felt, and it was clear as day that Tommy was fucking terrified.
"It's just..." Tommy's eyebrows furrow, expression one of deep thought. "Y'sure it's safe?"
Wilbur can't help but huff a short laugh at that, unable to take Tommy's dubious expression seriously.
"I know, I'm sorry." Wilbur apologizes, not sound very sorry at all. "But I wouldn't ask you to do it if it wasn't safe."
Tommy quiets for a moment, considering Wilbur's words.
"And 'm not gonna... prolapse??"
Tommy's first time getting fingered ends up being treacherously slow. Wilbur doesn't mind. He's done his fair share of waiting when it comes to Tommy, and it's always proven to be worth it.
This time is no different. Tommy has always been a natural performer, and Wilbur is certain he could've found success as a different type of content creator entirely. It was a shame he wasn't recording the whimpers slipping out of Tommy as Wilbur massaged his rim with wet fingertips.
It definitely wasn't right of Wilbur to be teasing like this, not when Tommy was so obviously nervous. Wilbur couldn't find it in himself to regret it though, Tommy's reactions were just too cute! You'd think the boy was a proper virgin, with the way he gasped sharply as Wilbur started pressing inside.
"'S weird.." Tommy says after a moment of panting, shifting his weight on his knees uncomfortably. Wilbur can't help but smile as he thinks about how exposed he must feel, on his hands and knees trusting Wilbur to stretch him open for the first time. "Is it supposed to feel good?"
"No, I'm just doing this to fuck with you." Wilbur answers sarcastically as he curls his finger inside of Tommy. He only feels a little bad as Tommy shudders in response. "Just have patience, ye of little faith. Pretty soon you'll be begging for me to split you open.