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Hi, guys, it’s Autumn, and I’m here today to talk to you about strap on anal training! This is the second installment in my series about strap on play.

You may have also read my blog over on The Daily Cocksucker about dildo cocksucking training. If you haven’t, I highly recommend it because, while I wrote it from the perspective of someone who’s seeking good-quality dildos for cocksucking training purposes, it also applies equally to someone looking for strap on anal training with a dildo.

What You Need For Your Strap On Anal Training

Of course, you will need some sort of insertable for your strap on anal training. This can be a dildo, a butt plug, some anal beads, or even your own fingers. I recommend using a dildo if at all possible, simply because that’s what will be going inside you during strap on sex with me. But if you can’t get your hands on a dildo immediately or if you simply prefer to use something else, that’s fine, too. (But, please, please use something that’s designed for anal insertion. The risk of using household objects or vegetables is much too great. I don’t want any of y’all going to the hospital!)

In addition to the insertable of your choice, you’ll also need some lube. I wrote a blog for Domination Boot Camp about the best lube for anal training several months ago, so feel free to take a look at that one if you have the time. If not, to make a long story short, I recommend silicone lube if you’re not using a silicone toy or oil-based lube if you’re not using a condom. But water-based lube will also do in a pinch.

If you would like some personalized guidance with this process, you’re always welcome to call me whenever I’m available. I would love to help you! It’s so much fun introducing people to strap on play, after all.

Trying Anal Play For The First Time

When giving anal play a go, be it for the first time or the five hundredth time, it’s always very important to use plenty of lube. More than you think you need. No, more than that. There you go. When you think it’s way too much, then it’s enough for strap on anal training!

Be sure to apply it not only to your insertable, but also to your anus. The more slippery everything is, the easier it will be to insert your toy or finger. Then, once you and your insertable are lubed up, it’s time to find a comfortable position. Most people seem to have the best luck lying on their backs for this. But others prefer to sit down on their toys, while still others will get up on all fours and do it that way. Whatever is easiest/most comfortable for you is fine.

Once you get into position, all that’s left to do is take a couple of deep breaths to steady yourself and take the plunge! Go nice and slowly for me. Don’t get in a hurry. If you rush too much, you might hurt yourself. While I admit to having a bit of a sadistic streak at times, anal pain is not something I’d wish on anyone, so be careful!

Soon, You’ll Be Ready For Pegging

Once you get your toy or finger inside yourself, slip it in until you reach the base. Then, give yourself a minute or so to adjust to the size of it inside you. After you’ve done that, you can start moving it in and out. Adjust the angle from time to time as you fuck yourself with your insertable, to see what feels best.

And of course, I should point out that at any time in this process, you can give me a call for assistance or moral support. You may need to go through it several different times on several different occasions to get used to accepting something inside yourself like that. But that’s ok! Take all the time you need before you move on to the next step, which will be actual cocksucking and pegging with yours truly.

If you’d like some help or some company with this, please give me a call for some strap on anal training phone sex. I’ll be more than happy to help you out or just be a friendly on voice on the other end of the line, cheering you on. I look forward to hearing from you!

1-800-601-6975