We’ve been having this casual thing, and despite all the rubbish you read in the papers and on your TL from those ‘higher-than-though’ witches who can’t land their brooms, this girl actually knew how to make a casual fling work. I didn’t trust her, didn’t need too, that’s why there were condoms, circumcision and lube.
So just out of the blue, in the midst of texting about her annoying boss and some guys she is thinking of going out with, a text is received: “When are we trying anal sex?” I am obviously stunned by this q, and well, trying to hide my nervousness I respond: “whose anus first?” Yeah she was kinky, but I doubt she was the type that wanted to put on a dual and romp me as I did her (modern sex can be so overwhelming)… I have always wanted to try anal; I just didn’t have it in me to put another human being through so much pain just to fulfill a pleasure or even curiosity. For me that is how those thin psychopath misogynistic lines are easily crossed, so I have never wanted to ask any woman, because those odd beings tend to want to bare pain as a form of leverage for love.
Crazy I know, but that is just them for us.
So, I decided to do some research on it (anal sex) and stumbled across a very informative piece on vice mag that is a step by step guide fit to equip any hole hopper sufficiently. I stock up on lube and keep repeating the words: “She is not a pornstar, I need to take it very slowly” about 49 times. I am still nervous and excited at the same time, with a very high anticipation of being stopped just as I enter, cause truth is, it seems like a very unnatural thing to receive as oppose to giving out on that passage of life. The mood is right, we are well underway, I am in her vagina, pleasing her and making sure that I at least feel it contract, with her legs shaking at the same time, before we jump onto the elephant in the room.
I reach 10 yards and am ecstatic, it is time. I reach out for the lube on the side of the drawer and position myself in such a way that I can keep at my strokes in the “P” while have a good angle at the “A”. I start applying lube around the “A” area, then I apply more lube, the article advised that lube lube lube lube is the only way one stood a chance. Then after what seems like sufficient application, I slid my middle (lubricated) finger in to check the reception, without stopping the strokes. Her breathing changes, but she doesn’t reach for my hand or anything, it seems she is enjoying this. Great! I keep that up for another minute, then I decide it’s do or die, nervous as a virgin but focused, I apply more lube on my “D” then go back to apply a bit of lube on the area again, I hold my tool closer to the area of penetration and slip in, but it goes in too quickly and there is no drastic reaction from her. Yep, “wrong hole fool” but I am looking for the wrong one this once “Uwrong Uright”. I slip out and decide maybe let me keep a finger there as my flagstick, I am not experienced with this side of town so I will take all the help I can give myself.
I manage to hit a hole in one with my second attempt; sliding it in slowly on high alert for any discomfort on her side. To my relief, she decides to stretch her hand to my waist and indicate I can gyrate (what a queen). I start gyrating and well it is as warm as everyone claims it is, but it is not that incredibly gripping, but grips more than the “P”. I lasted for like 2 minutes, cause to be quite honest, I was totally astounded by living this fantasy with someone who seemed to be enjoying it as much as I was. Yeah yeah, I was wearing a condom you joy kill. I have to say my first anal experience was A-Okay and I am highly convinced I am now the A-master. I just won’t try it again anytime soon, because I wouldn’t like to let woman think they have over-invested in me now that they gave that away.
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