50 anal cherries

You just kind of slip it in.

.

Offer her an extra $100.

When doggy action act like you have chosen the wrong hole.

TBH, it isn't that big of a deal; especially if she isn't into it. I had one chick that would only do anal and blow jobs because she figured that wasn't cheating.

Wouldn't it be great if you could say it with a Hallmark?

If you love her give her a 3 month heads up that it's "going to happen" & mentally prepare. Then, one night, after some wine & bad jokes, make it as romantic as possible. Basically, you have to set ground rules. For me, anal is required 6-10 times a year. That's less than once a month. That's fair.
Ds

...and a couple of chicks that were virgins, and did anal, yet kept their virginity while doing porn.
{Until one lost her virginity live on Kink...}

Slip it in and be done with it

- "Can I fuck you in the ass?"
- "Yeah, just take it slow at first."

Done!

Too late... :1orglaugh

The same way you introduce sex into any relationship. Pretend to be indifferent about it.

alcohol. that's typically whats worked for me to get my girl to try stuff she wasn't really into. a good number of drinks, eating her pussy like no tomorrow to get her good and worked up and then while fucking her doggystyle stick a finger/thumb in her ass. from there hopefully she will give you the ok to fuck it.

http://www.xvideos.com/video580763/oops_wrong_hole

http://www.xvideos.com/video4213530/...e_motherfucker


5 years in relationship and engaged, i think you are fucked.

You don't ;)

??? just tell her you want to fuck her in the ass...bring it up light...be like..."your ass!......i want to fuck it"....

Reposting this pic for all those recommending just sticking it in there (without prep).

This. Will. Happen.

Now I'm hungry, thanks. :(

:1orglaugh:1orglaugh:1orglaugh

Surprise him.

I like the surprise effect since i am not the one who takes it!

http://img204.imageshack.us/img204/306/502vo71a.gif

:1orglaugh:1orglaugh