Usually when the chick and I start fooling around its already after my pockets, and everything are empty but for this time, I was not even kissing, touching, or initiating anything...... She's very afraid of anal and only lets me do it every once in a blue moon BUT heres where the fun begins... She grabs the doc johnsons and my brass guitar slide (Didnt see she had the slide) and lubes her self and I was thinking "alll right!!!!!" and I got insta hard, went to the other side of the room to undress/put things away. then I see her playing with her ass (I was on the other side of the room still undressing and taking off jewelry unloading gun, etc... Its a routine I always go through and she knows this, I dont leave my gun unloaded very often but tonight I did)... Anyway I hear a gasp and a grunt and moan and look over and she has the damned tapered guitar slide (and its a thick one too) in her ass!!! to her for doing this on her own without help!!! Anyway I went over and her vag was seriously nearly dripping wet, and hoootttttt.... I asked her what she was doing and she said "I want to stretch some I got this idea because your head always hurts me bad as you enter so I think stretching will help" I tried to talk her out of it but she was persistant.... Apparently she had been planning to do this all day! its kinda fun looking into the rectum through the opening in a guitar slide btw, and was kinda a turn on, looks like vag walls anyway, she told me to go get her a glass of water, so I did and when I came back from that she had a small coke bottle that I had recently emptied, I immediately knew what she was thinking and I was telling her sweetie, dont you think we should use some plugs or a dildo or something to do this? I'm not 100% sure but I think this is something you should work on gradually and not force all at once" She said "shut up and get your pants off and get over here!" Yes ma'am! Anyway, after one of the most amazing blow jays ever (seriously she has NEVER been this wild), i got her on top of me ass in my face and started to lick her ass, gradually pressing my tongue into her anus.... mm warm clean anus ftw!!! After a bit of this, and some more lube, and using my fingers in her anus, she soaked the bottle in lube, soaked her ass in lube, and proceeded to work the bottle top into her, as I sat back and in amazement at this seriously new phenom I was watching! She put the tip of the bottle (where the cap clamps on) and gently pushed, relaxed, pushed sideways, and relaxed, and finally brought the bottle perpendicular to her ass and with a gently push broke through and now the ribs of the cap area were in, and she was panting heavy, she told me to hold the bottle in her ass, and then started sucking on my balls, and more blowjay goodness, then she started fingering my ass a bit (FTMFW!!! I love when she does this! ). While holding onto the bottle, she started to grind back onto it, and I would sorta let the bottle move with her, and she said no! Hold the bottle in place... She gradually, while sucking me, pushed back onto the bottle slowly over about 5-10 minutes, groaning and grunting until the top of C's were at the rim of her ass, she couldn't get any more in... She said that the bottle wouldn't go any further it felt as if it were hitting bones in her ass area, she we lubed, and tried and tried but could not get it in any further.... After gentlly coaxing her and telling her that I didn't want her to go any further anyway, that this was amazing (seriously, its fucking awesome seeing the insides through the bottom of a coke bottle) we gently worked it out..... the bottle came out with a hollow pop sound finally and I giggle but her anus was gapped a bit and when she would pant, it would close up and open up as if winking at me, the bottle ended up on the ground, the girl got tossed to the other end of the bed and got fucked in that winking "little" hole. after I came in her ass, and she sucked me off and cleaned me up she asked me to take pics (of which I am not allowed to share) of her ass so she could see if she damaged anything.... She said it was sore and when she went to go to the bathroom it hurt a lot but afterwards, the pain subsided, and this morning she said it was if nothing ever happened Wow, what a night!