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Straight guy, been into anal since I was 15, am now 20. Went from barely being able to fit a finger in me, to taking toys that are 3" in diameter and a foot long, and I have an XL Nova from Bad Dragon coming in the mail.
I usually do butt-stuff twice a week. I've done it every day for a month, and I've gone two months between sessions. Some advice for all the trans folk out there on how to make anal not be so unpleasant;
Enemas. When I first started out doing anal, I would use water bottles to give myself an enema. Fuck you, I was 15. While they worked pretty good (and I still occasionally use them, especially if I'm away from my usual gear) the threads on a water bottle, and the hard plastic used to make them, are fairly uncomfortable. Not the worst thing you could use, but definitely far from the best. Nowadays, I use a shower adapter that mounts on my shower head, and has a stainless steel nozzle. I fill myself up several times, usually between 4-6 times, and on the final time I fill myself up as much as I can and use a plug to hold it in for about five to ten minutes. Get a nice no-slip bath mat, so you can step out and empty yourself into the toilet. The last fill up is generally around a gallon, in terms of volume.
Whole process takes about twenty to thirty minutes, cleans out my entire small intestine, rectum, everything that's gonna be getting used during anal. This is coming from someone that's into fisting, and ridiculously large insertions.
After my current method, I've only had shitty-dick happen to my toys once, and it was a small pebble.
As far as eating habits are concerned; I eat whatever the fuck I want, because I'm huge as fuck, and have no qualms with blowing everything out of my ass for half an hour with a gallon of water at a time. For all the girls here, I would recommend going on an all-liquid diet, supplemented with vitamins (nothing crazy, a good multi once or twice a day as recommended by the bottle) for three days. There won't be anything there, but it wouldn't hurt to do an enema just to make sure.
For the record, I had a terrible problem with constipation, and my doctor recommended enemas, way back when I was 15. Worked …
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