First Time Bottoming

[cgreg2033]

I'm a total top and have been almost my whole life, however when I was just starting out exploring gay sex, I thought we both HAD to bottom and top equally, or somewhat equally. I had fucked my best friend several times at this point and he always seemed to love having my thick cock pounding a load into his hole.  He had repeatedly eaten my hole and fingered me, and it mostly felt good so one summer day I was so horny it was nearly painful and I decided to invite my best friend over for a fuck.

I was masturbating in the bathroom to kill time and started fingering my asshole.  It felt good, like I said I was incredibly horny.  I grabbed a dildo shaped object and put oil on it and slowly pushed it against my hole.  The object had a round end that was the thickest part of it, and it tapered down to the thickness of a finger.  The thickest end wasn't really very thick, about the size of a half-dollar coin.  It hurt like hell getting it past the second anal ring, but since the object tapered so much it was mostly smooth sailing after I got the thickest end past my inner ring.

I slowly worked the thickest end in and out of my hole, trying to get it relaxed and used to penetration.  About then my buddy showed up and we got onto my bed and began sucking each other's cock.  He was leaking precum more than usual, so I guess we were both more than the usual amount of horny.  He got between my legs and started sucking my cock and fingering my hole.  I rolled over onto my stomach and he got the hint and crawled on top of my body, forcing my legs open so they were spread wide.  He spat and lubed his cock head, ready to penetrate my ass.

Now I should say, that the biggest thing I'd had up my hole was the object I had just recently been fucking myself with and his cock is still, as of today, the biggest I've ever seen in real life.  It's over nine inches, uncut and incredibly thick.  I felt him place his wet cock head on my slightly oiled hole and start to insert his monster cock into my virgin hole.  Initially I cried out, although UI knew the first time would hurt.  Looking back all I can say is how dumb and uneducated we were.  We should've been using oils, or lube or anything besides just our spit to have our virgin holes fucked the first time and many times after. 

Anyhow, it felt like a telephone pole was being pushed into my ass and up into my stomach.  He lay completely on top of me working his gigantic cock in and out of my battered hole.  I was crying but he couldn't see it. All I could do was lay there and take his cock hoping he'd cum as soon as fucking possible.  It didn't take long, but it felt like an eternity before he finally filled my hole with his cum. 

I immediately went to the restroom and expelled an enormous amount of cum and some blood, but surprisingly I wasn't bleeding as much as I felt like I should be.  I rubbed my tender hole with my fingers and stuck two fingers inside my cummy hole while I jerked off, shooting cum all over my chest, stomach, wall, and floor. 

My first time getting fucked was a painful experience, but we didn't know the proper way of losing or taking a virgin hole.

[Gabe902x]

HOT

[Guest deleted1107]

So hot!

[Phallarchist]

Painful and bloody is a great way to start. How else will fags learn that they exist to suffer for male pleasure?