Message: Making Anal More Enjoyable
wet-n-wild-in-cali: I’ve lived most my life in a lesbian relationship. I’ve never had a man in ANY way. Lately though, had a lot of fantasies about trying anal, either with another woman and strap-ons or maybe even with a man. I’ve had toys in my ass in the past which were sometimes okay but rarely really pleasurable (often hurt) and sometimes fingers there while enjoying clitoral stim and the two lead to really intense orgasms. What advice toward preparing myself, making it more enjoyable? Too I have hemorrhoids.
Start with what’s been pleasurable for you in the past: it’s not at all uncommon to need clit stimulation along with anal to make it pleasurable, so be sure to include lots of that whenever you experiment anally. Start with well-lubricated fingers for a while, incorporating anal play at whatever level is comfortable for you when otherwise masturbating. Gradually increase the number of fingers you can comfortably fit. Everyone needs to go at a different pace when increasing size, so you’ll just have to see what works for you.
Work up in size until you can fit a medium size butt plug (1″ to 1.5″ in diameter, perhaps). These can be great for improving muscle control and temporarily loosening up before doing something else, plus they just help you get used to the feeling of having something filling you anally. They’re great to wear while masturbating or during other sexual activities, and they also can be worn while doing other things in preparation for planned anal masturbation or sex.
I’m not too familiar personally with anal sex with hemorrhoids, though I do know some people seem to think that careful anal masturbation and sex has actually helped reduce them—I have no idea if this is true, however. I presume the presence of hemorrhoids can add to potential pain. Usually, my advice is that if you are experiencing pain during anal penetration you’re either not using enough lube or you’re trying to go too fast with something you’re not yet ready to fit. With hemorrhoids, however, it may simply be that they’re causing the pain. I suspect the advice of taking things slowly so as to reduce or eliminate pain would still apply in the same way, but with perhaps a different mechanism triggering pain.
Careful experimentation is the key with anal. And lube.