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Mistress has gotten herself a brand new strap on and has decided that she wants to train me not only to be able to take it with ease but that she wants my asshole to be able to gape open. Any advice or anything I should be aware of about anal training?
You'll gape upon exit. especially if you don't "expel" it with a squeeze. Learn to suppress that... breathing ala Lamazz (sp) training is key imo.
As far as taking it easily, start small, wear ever larger plugs to stretch the sphincter... and lots of kegals to keep it strong and resilient.
Lots of lube will help entry...
I think just fucking yourself with larger and larger toys is all you need. I think a fat dildo is better for stretching with a plug of the same thickness, because you relax around a plug after the wide part has passed.
Don't forget to push out like your pooping when pushing whatever your going to use in; it really takes away much of the discomfort.
I just started my bum training with my Daddy more or less 2 weeks ago. I was really new to it and was feeling really scared about it. But I really want to try it out. So we started using a finger first, then a marker, then a hairbrush. And finally I have my first new toy! Thanks to my Daddy! I was really terrified at first, but Daddy was there to help me.
Help! My Master wants me to wear a butt plug all day. I am very new to BDSM in general, not to mention plugs. I don't want to disappoint him but I don't know how I'm gonna keep the plug in all day!
For me the most difficult part is keeping it in when bending over. If I go too long between wearing it, it gets a bit uncomfortable to wear all day unless enough lubrication is used. The mental challenge of wearing it at work is wondering if someone will notice, but is so much fun and it pleases Him greatly to know that I do it for Him.
If I may suggest usage of the bathroom at some point before putting things in there. :)
As for your question bound_for_you: it's wonderful you're trying your best I personally would be happy with that if I were a/your Dom. Just be honest with your Dom and yourself, do what feels right and your best. :) *pat, pat*