I've yet to buy a prostate massager or butt plug - just haven't gotten around to it. Have used a glass dildo occasionally to try to milk my prostate but only produced a couple of drops of fluid and didn't find the sensation to be all that pleasurable. Attempts to massage my prostate internally with my finger feel good but are hard to sustain in order to orgasm.
I do a lot of external prostate massage while I wank and find that it really heightens the pleasure for me. I like to edge daily and can sometimes go up to 2 hours. I'll often massage my taint while edging and that helps to produce a little more precum.
My most success in massaging my prostate has been lying on the floor on my back and putting my legs up on a couch or chair. I can then play with my cock and easily rub my taint. In this position, I use one hand to shake my cock and the other to rub my taint. I never stroke - just wave my cock around - and I thus don't get really erect. When I get things just right (hitting the prostate), I'll start leaking and spurting a watery white fluid all over. It is not as thick as cum but the amount is definitely more than my normal amount of ejaculate.
I enjoy porn where a guy milks his prostate with a dildo. I notice that a lot of the milking occurs while squatting on a suction cup dildo. It seems that squatting might "expose" the prostate more or that it may be easier to stimulate the prostate in that position.
So, a few days ago, it is early afternoon. I'm horny from edging in the early morning and the urge for more playtime is strong. I found a quiet place in the house, took off my clothes, and got into a squatting position. This exposed my taint and made it easy to rub, prod, and press. I grabbed my cock at the base with one hand and shook or waved it while I rubbed my taint with the other. I interrupted the waving several times but continued the taint/prostate rubbing and pressing. Within 5-6 minutes, I could feel my prostate begin to tingle and feel REALLY good. I kept massaging the taint and the feeling inside kept getting better. My prostate began to flutter - I envisioned that it was moving as you can your tongue when trilling. OMG, it felt amazing.
Fluid started to pour from my cock onto the tile floor. I was waving/shaking my cock while rubbing my taint. After what seemed like more than a minute, I had to stop - the feeling was so intense. My prostate felt like it had been zapped with an electric current. The floor was a complete mess. Fluid everywhere - whitish, watery splats - nothing thick like my normal ejaculate.
I really need to buy that aneros or prostate massager.