Peg Me Gently

Are you looking for a relationship or are you looking for a mistress or just a one time fucking? Exactly WHAT you’re looking for changes how you go about “getting” it.

I myself would NOT be interested in a fuck for hire or a fling with a stranger, it seems so... dirty. If you’re a consenting adult and that is what you need or want and both parties are down for that type of arrangement, power to you, I won’t stand in your way I just won’t be lining up to take part in the festivities. I support your right to get down and dirty with someone you just met.

To speed track to a pegging, I would want to be in a healthy relationship and then be open about my sexual desires. If the person your with (or trying to get) is shy to the subject of sex or sexual fantasy, the likely-hood of a pegging is pretty low.

Don’t expect to just get a pegging, even in a relationship. Realistically, you’ll find a lady would will indulge your fantasy once in a while, about as often as you reciprocate and indulge in her fantasy.

Well, Tumblr really let me down on your question! I never got a notification that I had received a ask/message.

I had a desire to be pegged by my wife. I thought the ideal of a cock she could wear, like a feeldoe, was worth giving it a try so I ordered one. When it finally came we made a few attempts at making it “work” but it just wouldn’t. Either the strap-on wouldn’t stay in her or it was painful and wouldn’t go in me.

The desire didn’t quite go away but since we weren't making any progress we abandoned it (for like 5 years)

Things didn’t really go in our favor until I learned to explore myself and practice inserting smaller toys and working my way up to small diameter dildos over a period of time. Ironically, some of the cheapest dildos we ever bought were “right”, in shape (curve) and size that made penetrating comfortable.

The right lube also goes a long way for anal! I *LOVE* Doc Johnsons Anal Lube.

I got to the point where I could easily take a 1″ diameter toy without warming up. At that point penetration was no longer an issue and it paved the way for moving on to pegging and some GREAT love making sessions.

Things are going to awkward to start out when you’re both getting the hang of it, it’s new. Think of when you were teens and didn’t know anything about sex (hand jobs, blow jobs, full on sex, etc). The difference between then and now is that you both shouldn’t be afraid to communicate. If it hurts him in any way he has to speak up and let you know. Communication is key.