My GF and I were out of town on vacation and having a great time. We'd both gotten pretty drunk and often when she gets drunk she gets pretty horny. This night was no different. We'd just finished a great meal and a fair amount of wine and some more drinks at the bar and were stumbling back to our hotel when she started being extra playful and coy.
We get up to our room and she's begging me for it. She wants sex so bad and I'm just not up for trying to fight whiskey dick when I know I'll be great and ready to go in the morning so I keep trying to put her off... when she tells me those little words no guy likes to turn down....
"I'll let you stick it in my ass...". Now we'd done it a couple of times before. 1 or 2 times with good results and 1 or 2 times with uhm... not good results. But here I am, drunk as a skunk and a GF so horny she's willing to give me anal.
Who am I to say no?... So I grab a big bottle of lube and squirt it all over her hole and plunge the fuck in. She's screaming into a pillow and clawing at the sheets. I did not give her any warm up at all. However, the whole thing was pretty hot and totally overcame any sort of WD issues.
'Twas not one of my finer moments, I'll admit and we both laugh about it now. If Anal ever comes up (and with our friends that's kinda often), she will find a way to retell this story, even though it happened several years ago.
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A bit about sizing. I think I'm average (I'm guessing most guys think of themselves as average). 7" long, 5.5" circumference. I don't know if this is average, small or large. My GF is 5' 4", ~110 lbs. We just started playing with a new girl (5' 7", also ~110 lbs) and as such my GF said I can do anything with her, except anal (we are keeping that to just us). When I told our new girl this she looked at me, smiled and said, "When I first saw your penis I knew that you and I would never be having anal sex, so that's not really a problem." I do take that as a compliment but I'm also a little disappointed.
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