Anal sex pain and prostate orgasm help?

    • Anal sex pain and prostate orgasm help?

      Hi everyone, Im not sure if this is the right place to post this, other places have been pretty helpful, or if its appropriate, the rules and agreements dont seem to prohibit it, I dont think it is, and the forum says sex advice, some other posts too are pretty frank so here goes...


      I'm kinda young (18) and new to sex in general (still a PIV virgin actually), but Ive developed a FWB thing with a really nice lady a few years older than me(33). The only thing, and its not a problem, but she doesnt enjoy PIV sex, lovely wonderful oral but.. anyways to the issue.

      She really enjoys strapon sex, I was pretty apprehensive and scared at first but I've found myself enjoying it quite a bit. Its been a few weeks since we've started getting physical, seeing each other every couple days. I was hoping the bit of pain might go away after the first couple times but it persists a bit (maybe a dozen sessions now), during its almost all pleasure, but initial penetration is a bit painful as is pooping slightly now and then afterwards. No pain when not using my bum, and its only near the entrance. She's very gentle and all that, takes her time, lots and lots of super slippy lube and we don't rush into it, she spends quite a bit of time baby-oiling, lotioning, blowing and fingering me before the sex starts.

      Its awesome and I'm always rock hard when penetration begins, I dont honestly mind the little pain, its brief and maybe she gets off on it. Realistically I know a smaller dildo in my very recently virgin bum would probably be the best, and she has a couple, but this one is her favorite so I'm inclined not to ask, I'm sure she wouldn't mind but I do enjoy the size/shape/texture too. Our sex does get a little animated at times and she puts me in all sorts of positions, Im a touch on the "petite" side and she's not, not big, just big enough to kinda woman-handle (hah) me when she gets close to cumming. She apologizes profusely and showers me with kisses and cuddles and lotion when she can tell shes gone a little too far, and I almost hope she does get a little rough because of that, its very very nice.

      So uh, large penis/dildo anal sex havers, does the body adjust after a bit or do you have any tips? Is there maybe a position that works better for vigorous/long thrusting and getting her off? Right now when she really needs to cum she puts me on all fours or laying on my stomach and goes pretty deep, then pulls nearly or all the way out then all the way back in with her pressing on my cheeks for a bit, the dildo is 8 inches or so and I think the long stroke and harness pressing on her clitorus is what does it for her. It feels absolutely amazing but it is when it can hurt a little too. Theres no allergic or chemical reactions (lube and dildo is all the proper kind and shes safe with the lotion and oil careful not to get anything but lube inside). We've discussed the pain so she knows, and we both think its worth it, at least if it doesnt get too much worse. I also want to be sure the pain isnt a sign of something unhealthy, its not her first rodeo boy-virgin/strapon wise, and shes very reassuring, shes completely mature and trustworthy as well as working in the healthcare field so its really more a matter of piece of mind.

      Oh, one more thing, shes been trying to give me a prostate orgasm, and says when it happens Ill know for sure, sometimes it feels reaaally close but Im not sure having not had one before. She's alluded to this not being a problem with other boys in the past and has ordered a couple of those aneros toys as well as a few plugs of various shapes and sizes to try on me. She also ordered a prostate attachment for her big hitachi vibrator... so I suspect I will be having prostate orgasms soon come hell or high water, but if anyone has any tips for coming while being fucked that would be great, thanks!

      Um I think thats all, wow long post, sorry for any grammar errors and thanks very much if you're still reading! Sorry again if this is the wrong place!