I can't stop thinking about what Chilchuck's first time bottoming would be like. Do you think it was with another half foot or a different human race? Did they have lube back then, or was it just spit? Was he embarrassed about it? Did he come quickly? Did they stop going after he came, or did they keep going?
I like to imagine it was with someone much bigger, maybe he was anxious about if it could even fit or if he got harmed in the process. Maybe the top could only get it half way in. Maybe he pretended he didn't like it at first but his dick leaking gave him away. I feel like he'd try to hide his moans until it felt too good and just couldn't hold back anymore from screaming. Chilchuck gripping the bed sheets, tearing up, groaning, as he comes hard.
And then, the cherry on top, the next day he asks "Why does my ass hurt so much?!" and then slaps his face as he remembers.
HOLY SHIT ANON
COLLAB WITH ANON<3 (NSFW)
CHILCHUCK BOTTOMING FOR THE FIRST TIME
When it comes to anal, Chilchuck knows its best for the one who will be receiving to be relaxed. And the best way to do so is by orgasming.
Halflings are known to have high libido as well as resistance. So it's no surprise that the man can cum and shoot loads into the mattress around 3 times before he's finally tired, out of breath and laying spread out in the bed.
That's when he's ready to spread his legs. They can either use Chilchuck's own cum, spit, or some oil to lubricate his tight entrance.
Fingering isn't something new, it just wasn't enough. Chilchuck would be pinching and playing with his nipples as his ass gets accostumed with the intrusion. By the time he's already hard again, he's already cursing and impantiently demanding his partner to "Just fuck me already I don't have all night!!"
Of course he reconsidered his demands once he felt the tight ring of muscles being stretched by the thickness of his partner's dick. But it's doable, especially if his other erogenous parts are getting licked, kissed, sucked and touched.
Once he gets used to the feeling of being stuffed. His body turns into jelly. He allows himself to be manhandled, as long as Chilchuck gets to order around and moan the dirtiest and naughtiest things in his mother tongue, and the common tongue as well.
The next day, Chilchuck is pretty grumpy that his ass hurts and stings like a bitch, BUT THAT'S NOT ALL OF IT!!! The poor halfling can't stop going to the bathroom because SOMEHOW, there's still an absurd amount of cum inside his colon that hasn't been expelled yet. gross.
