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I've just done this now, I've been curious for a long time how anal sex felt. I've seen gay porn several times... too scared to come out as 'possibly bisexual' I just decided to experiment myself.
Ironically I used almost the same device as you. I used the back end of a toothbrush and olive oil as lube.
I can only say I rate the experience 'somewhat satisfactory.' the penetration felt great for awhile (5-10 mins) and I thought I was almost going to have a hands free orgasm, I was so excited. My penis kept getting to about a 8 out of 10 on the ejaculation meter, but never to 10 (orgasm/ejaculation) That disappointed me. So finally I decided to jerk off at the same time and it didn't take long to cum... But... it wasn't mind blowing... in fact, it felt like my orgasm was weak as opposed to what I was told it would be with anal play, explosive. While I was cumming I barely noticed it, probably cause I was distracted by the feeling of the penetration.
So in hindsight, I'd say it was (kind of) worth it. But not nearly as amazing as I've heard. The penetration was pleasurable but not mind blowing. If it didn't ruin my orgasm I'd have given the experience a 10, but since it did I give it about a 5. while the penetration was pleasurable it doesn't beat a good long contracted (penis) orgasm.
Sorry I kind of got off topic cause I wanted to write my story down. I didn't experience any physical signs of irritation or disruption. I did however have a bit of an anxiety attack after doing the deed, which I found odd.
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