Can you fill a condom in one go anonon?

You need to start with fingers and/or smaller dildos, and fuck yourself while jerking off how you usually do. Eventually your body associates that "filled" feeling with jerking off, and your prostate responds in kind. You'll be having sissygasms before you know it, my friend.

>you will never have your prostate milked by a milf.

why live?

I don't know. Maybe with the right diet and a week of prep time.

so, you mean do anal only?

Yeah, i have a small dildo i use. I can get to the point of having a dry orgasm, so usually I do that and then just fap after. I heard it was good to not touch your dick at all when first doing anal stuff, to dissociate sexual pleasure from dick touching, but i guess what you said makes sense.

You play with both for a bit before switching to anal-only. Your body/mind needs that first bit of both for the anal orgasms to hit more intensely.

thank you user, hoping i can eventually completely indulge this fetish

it helps to put some pressure on your dick. You often see traps squeeze their dick behind their thighs, cock rings work well too.

How do you even find your prostate with your fingers? I can never find the "almond"-shaped bump in there.

Question bros.
From the dildo in the webm, do you think that the head/bumps on the dikdo will be sufficient in stimulating a prostate to hands-free orgasm?
The dildo is listed as a g-spotting dildo, so would it also apply to prostates?

Attached: SecondIncredibleAmericanindianhorse_2918.webm (524x1042, 1.61M)

it's not almond shaped, more like a walbut

I still don't feel anything up there. Maybe my fingers aren't long enough or I just wasn't aroused enough.

>tfw gfd gf likes to milk me

you might not be far enough, it should feel like it's right behind your dick sort of. Maybe a little higher

Could a dildo like in do the trick?

any dildo should work fine, looks pretty thick if you're a beginner though

Hmm, I always thought that was just to show things off, didn't realize it actually helped the whole milking process

yeah I tried it with a cock ring yesterday, it makes a big difference.

do you still get the fabled prostate orgasm with no refractory period? or is it a normal ejaculation when you do it this way?

nah I still get a refractory period, it was basically hands free though

Any other good tips for milking? No homo btw

get a toy specifically made for prostate massage basically. Dildos are ok if you're getting off on the idea of a dick, but otherwise you basically want to just do as much prostate contact as possible. You don't really need to fuck your ass too much even, just pressing against the prostate works fairly well.

anyone got any hot nurse/medical related stories?
is there any dumb but real scenario where some guy would be milked by a nurse?

Will cumming hands-free solely from prostate stimulation still cause me to feel post-fap regret/shame for going to such lengths with a dildo up my ass to cum or is the process different and will not result in post-fap regret?

I assume that you'll have whatever regret you normally have, it's still just masturbation at the end of the day

>ywn inspect user's dicks and watch them awkwardly shuffle around
>ywn try to hold back laughter as user cums in his pants from the slightest touch
>ywn tell user that his penis is too small for underwear and put him in a diaper

seems a little too soft, I'd go one just a bit more firm, good thiccness tho

only if you end up having a normal orgasm, you won't have it with just the anal ones (but you won't feel sexually satisfied, either, so it's a catch 22)