I decided to roll all of our anal adventures into a series. This is #1.
It's interesting to note that on our first date we got fairly candid (drunk) with each other. She told me that the only thing she wouldn't do is anal. The odd thing is she just blurted it out, we weren't even having a discussion about sex. Naturally, I took this to mean that she desperately wanted to try anal.
First story takes place about a year into our relationship.
1 The first attempt
We're in Vegas baby, and have an amazing room at one of the hotels on the strip. She didn't know it at the time but this was the weekend my future wife was going to lose her anal virginity. Being the sneaky bastard I am I methodically planned everything thing out. I had all the supplies pre purchased, and ordered her a massage in the hotels luxurious and highly rated spa. My thinking was, is if she's clean enough for a massage then she's probably clean enough for butt stuff.
Everything was ready, water based lube, bottle of champagne, dirty movie purchased from the on demand service in the room. It was perfect.