Why wouldn't he just ask for a date? Sure in the face of an 11 year friendship the answer will most likely be no, but at least he doesn't come off nearly as creepy.
He honestly would have had better luck asking her to actually sleep with him. Probably still be told no, but it's definitely creepier to have a friend tell you "I want to jerk off to you" than to have them say "I want to have sex with you"
Jock_Thespian on June 14th, 2018 at 22:46 UTC »
“Hey I’ve known you over a decade and I haven’t groveled for nudes once, you kinda owe me on this one right?”
Monkeyguy959 on June 14th, 2018 at 23:20 UTC »
Why wouldn't he just ask for a date? Sure in the face of an 11 year friendship the answer will most likely be no, but at least he doesn't come off nearly as creepy.
MadnessofKingHippo on June 15th, 2018 at 00:13 UTC »
He honestly would have had better luck asking her to actually sleep with him. Probably still be told no, but it's definitely creepier to have a friend tell you "I want to jerk off to you" than to have them say "I want to have sex with you"