Yes. It's only happened once but I really enjoyed it. I'd like to do it to my boyfriend but I'm afraid he'll freak out.
Anal play during masturbation is ideal & I milk myself dry - work into my masturbation dates regularly and will have fun with it now in my second time around this evening
I do enjoy it. It is difficult to get past stereotypes with certain people, but once the dam is broken, all bets are off.
It all depends on the skill of the person doing the fingering. After all, just ramming the fingers up there isn't going to get that far in appreciation points, whereas having the prostate conciously stimulated is a different matter altogether.
Im str8 but dont mind anal stimulation. when i was younger (highschool-college) i got real curious and firstly tried jerking off with my index finger in my butt, that felt kinky, and a vibrator twirling around the butthole felt intense. For any of you guys who are bi-curious , or you've fantasised about being given a prostate milking- the best thing i bought and used is the 'aneros' toy. look it up. its a specially designed anal plug for men that is shaped and contoured to target and massage prostate. now the cool thing is the toy also has an external bit that presses into your perineum(btwn anus scrotum), with more practice, you can master male gspot-orgs. the more you practice the breathing and relaxing techniques , the better you get at handsfree orgasms, because the way the toys is shaped, its designed to go in and out with each of your own anus/pelvic contractions..follow me? you dont need to thrust it in and out yourself. i dont play with my ass all that often, but over the 6 months after i first bought it years ago, i had my first prostate-orgasms that were incredible. the way i describe it is, when the ejaculation starts, its kinda delayed and kinda in slow-motion, the "im gonna cum" stage feels like it goes for eternity, and i noticed the ejaculation is slowed down and way more intense. the main thing i noticed is how my streams of ejaculation were cumming out slow and oozing, rather than the usual strong spurts. the whole orgasm feels prolonged and really satisfying. id luv to have my next gf do it for me;-) finger in the butt, mouth firmly planted on my member hehehe