Pegging in it's simplest terms is a woman fucking a man's ass with a dildo that is usually strapped on.  

Urban Dictionary:

"Anal sex reversed. Instead of the man sticking his penis up the woman's butt, the woman wears a strap-on and sticks it up the man's butt."

Wikipedia:

"The sexual practice in which a woman performs anal sex on a man by penetrating the man's anus with a strap-on dildo. The neologism "pegging" was popularized when it became the winning entry in a contest in Dan Savage's "Savage Love" sex advice column, held after an observation was made that there was no common name for the act.[1]"



 
 
It's not always easy to get the words out "Honey, I'd like you to strap on a cock and fuck my ass."   For some men, it's downright terrifying.  Somewhere along the way we decided that assplay was dirty and closely tied with being a homosexual.  For that reason many fear their partners making assumptions and looking upon them with disgust.  So I always recommend a little education in those situations.  These two videos are fantastic to watch with your partner, whether it be for him or her.  Don't judge the videos by their covers they are extremely educational, funny and downright sexy, with several pegging sessions between different partners after the "how to" part.

Expert Guide to Pegging
Expert Guide to Anal Pleasure for Men

Now, if your partner is sexually open and up for most things, here are a couple of ways to gradually expose her to the idea of pegging: 

1. Start A Couples Blog on Tumblr - This is a great way to explore as a couple all of the things that turn you both on.  You would each be able to post to the same blog by reblogging pics you see that turn you on.  It opens up dialogue and is easier than just blurting out what you want.  You can start with light assplay pics and scenarios so he/she gets use to the idea that it turns you on to have your ass played with.  Every couple should start with some basic play before jumping into pegging.  Fingers, small toys, rimming, etc.  Once she is open to the idea that your ass is a pleasure zone, the fun can begin!

2. Watch Porn Together - Watch some porn together that has elements of assplay (fingering, rimming, etc).  Really let your arousal be known when those scenes come on so your partner gets the idea that this is a turn on for you.  If it doesn't open up dialogue right away then the next time you are in bed and both aroused, mention how much that porn turned you on the other day.  Ask her if she would be into giving it a try.  Tell her you've heard how pleasurable a man's prostate can be and you'd love to try it.  If you make it about your pleasure then chances are she will consider it.

3. Bring It Up During Sex - If you aren’t into watching porn together another way to open up conversation is to bring it up during sex.  If you are comfortable with it, let her know how much you love when her fingers brush your taint when has her fingers down there…or better yet her mouth.  If she is sucking or licking your balls, you can tilt your hips up and when her tongue slides down be verbal (moaning) and let her know there is a new pleasure zone she may be neglecting.  Same with fingers, if she is rubbing your taint, work your hips so that her fingers inevitable graze your asshole.  Again be verbal, like she just did the best thing in the world.  If you are feeling a bit forward and know she is in her kinky zone, grab her fingers and drag them lower, working them against your hole.  Tell her how fucking good that feels.  Once she is comfortable with playing with your ass from the outside, encourage her to work a finger in.  Tell her you’ve heard how hard guys can cum with their prostates stimulated and want to give it a try.  Once she is comfortable fingering or rimming your ass…then you suggest a toy (perhaps in your case not cock shaped right away).  You want this to be about you and her and exploring new pleasure and not about her being dom or having to be the "man" in bed.  Even if you crave your partner to be dominant, there will be time to ease her into that later.  Baby steps!

4. Phone Apps - For a more direct approach plan a hot night where the theme is reveal secret kinks to each other.  If you have a smart phone download an app called, Kindu (available for Android and iPhone).  It’s basically a series of questions about kinks and scenarios and you each answer them separately with things like yes, no, open to discussion.  I recommend going down on each other while the other one answers the questions!  Then you review them together and see what each others kinks are, which ones matched up and which ones didn’t. At the very least she will read through all your answers and see that your ass is turn on for you.


 

Types of Pegging

01/16/2015

 
Whether you are a man who's interest has been piqued by pegging porn or a lady who wants to show her man how pleasurable his prostate is, there are lots of different reasons why people want to try pegging.  The bottom line is they are all normal desires and should be embraced and explored. 

1. Prostate Massage/Play - Many men and women are drawn to pegging because it takes prostate play a step further.  Perhaps they have tried plugs and beads and prostate toys...even dildos and want to see what it's like to experience the ultimate in prostate play.  Often hands-free orgasms are explored as will as multiple male orgasms.  I like to refer to his as the softer more passionate side of pegging.

2. Femdom Play - This type of play cast the women in the dominant role and the man in the submissive one.  Often larger dildos are used as well as restraints and collars.  The focus is usually her pleasure and will often involve chastity devices and other forms of orgasm control/denial.   This is typically how you see pegging portrayed in porn. 

3. Cuckold Training - Some couples in a cuckold relationship will use pegging as a way to train the man to suck and fuck cock if they're interested involving the man in some bi-play with another man, typically called the Bull. 

4. Bi Play - For some men the attraction to pegging lies in their hunger for cock.  It may be a singular lust that does not extend to men in general.  It's a chance to suck and fuck without crossing any bisexual lines and can be the gateway to actual bisex.

5. Sissification - Some men enjoy being dressed up and fucked like a woman, taking it a step father than traditional femdom.  This dress can include make-up/wigs/heels and helps that man fully immerse himself in the female role, enjoying "the other side".