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.

She gets back from the massage still wearing the robe they gave her, and thinking back I think they brought it up to the room before she left for the spa. She looked relaxed, glowing, and beautiful. She was unaware of her rectums impending date with the head of my penis.

I start by pouring the sparkling wine for the two of us and chatting about what the spa was like. I make the same happy ending joke I make every time she comes back from a massage, and we make our way to the bed. I turn on the Porno, its a girl on girl. She will never admit it but she loves watching two girls play with each other. I must find a clever way to exploit this one day.

We get down to business. We don't 69 often but things seemed to naturally move that direction this evening. She's on top of me happily going to town on my cock while I'm face deep in her sopping wet pussy. I take this opportunity to stake out the battle field and plan my attack. I have in the past fingered her ass, and she generally seemed to enjoy it until I try to penetrate This was my first obstacle, breaking the seal. I started by fingering her pussy to get some of the juices flowing in the right direction.

I'm licking her clit delicately and spreading the honey from her honey pot closer and closer to the prize. When I start fingering her ass she's not surprised, it's something I've done before and its been generally agreed upon that this can and does happen. She squeals a little in a muffled, "cock in your mouth" sort of way.

I manage to break through the outer barrier of her asshole and am solidly penetrating her two knuckles deep with my middle finger. I slowly moved my finger in and out and I felt her start to tense up a bit, but she doesn't stop sucking my cock so I take this as a sign that things may be able to progress. And Progress they did.

She slides off of me on to all fours and I reach for the lube, with her looking back at me.

"Are you going to try to put it in my ass?" she asked.

"Is that alright?" I said devilishly.

"I guess. Just go slow." she whimpered.

Game on motherfuckers.

My heart is pounding out of my chest as I slather my hog with lube, probably using 3 times more than needed. I lovingly spakle my future wifes ass crack with lube until I'm convinced I've acquired an adequate amount of friction free area. I go in again with the finger just to make sure things are nice and loosened up. The moment of truth, I gently start applying pressure to her back door with the head of my cock. As I'm doing this she's pushing back, things are progressing nicely. The head of my dick finally pops itself into her ass, and I'm in.

I keep my promise and try to take it slow. Progressively moving my hips back and thrusting forward a little further in with every stroke. I immediately notice that this feels nothing like a vagina, it's much tighter and a little more grainy, but it feels amazing.I'm finally starting to get a bit of a rhythm going, and with all this excitement I'm literally imagining the holocaust museum to stop myself from cumming.

Then without notice she pulls away from me and rolls off the bed to her feet. She doesn't say anything just leaves me hanging there literally with my dick in my hand. She's headed to the bathroom. I'm concerned, but I'm also two seconds from cumming, I give myself a few wanks and fill my other hand with cum. I lay back on the bed with my mind racing. After laying there a few moments I hear the shower turn on.

A wave of concern rolls over me again as I move to the bathroom to offer help, or hugs, or toilet paper. What I saw when I got there made my heart sink, and made me feel like the worst human being on the planet. She was in the shower crying. I asked her if she was in pain. She said no. I decided to not bring up anal again after that.

Sorry if this killed a few boners, but it has a happy ending.

About a year later we got married, and surprisingly SHE WANTED TO TRY ANAL AGAIN ON OUR HONEYMOON.

but that's for the next story………..

Source: reddit.com/r/gonewildstories/comments/4162zp/anal_adventures_with_the_wife_1_mf