Any advice appreciated. I’m dying to bottom for the first time. I’ve tried the ‘relax’ thing, tons of lube, water based, silicone, oil, Vaseline.... I can get 3 fingers, nearly 4, no problem. Any toy, however, as small as one starting at 3/8” tapered up to 1”, might as well be three inches thick and covered in tree sap. And once I get it in, forget sliding it around, and coming out feels like my intestines are coming with it. I’d say I’m way too tight, but after being able to slide fingers in so easy, that can’t be. Does a greased up dick slide that much easier? Wtf? Frustrating...
Generally, you cannot get your fingers as deep in your ass as a toy will go. Any other problems there? You might have an obstruction in your rectum that a longer or wider toy hits. You might try a softer toy and different lube.
Sounds to me like you're not able to relax your sphincter. Might I suggest an anal training kit and small silicone vibrator. Sometimes you have to train your ass to relax. Butt plugs can be worn for hours and the vibrator can help the muscles to relax also. For lube I suggest Astroglide. It's very slick. Relax, take your time and don't rush, you'll get there bubbaatuse.
I feel your frustration and would recommend using a vibrator around your bung hole to relax your sphincter while gently and slowly making penetration. It can be difficult to relax it enough for enjoyable penetration but I experienced (early on) that the "spooning" position had mine the most relaxed. As I experienced anal more and more I was able to relax in different positions. Don't give up too easily because successful anal penetration will provide you with some amazing feelings.
Also a good warm enema to clean you out and expand the cavity and relax you helps a lot. I never do anal without cleansing. Google it. There are good instructions on the net.
It took me a long time to properly enjoy anal because I would tighten up as soon as the other guy's cock approached my hole. The trick that eventually helped me enjoy it from the start was to learn to relax my sphincter by counter-intuitively trying to push back as if I was trying to do #2, which despite what you might think relaxes the sphincter. Just make sure you have an enema first and are properly cleaned out, otherwise you might accidentally push out something else... Seriously, it really does the trick. Also try slowly with a small dildo or toy and slowly move it around in a circle once inside to relax and loosen up the hole, then you will find getting something larger in there isn't all that hard. But use lots and lots of lube, always.
I was with a rather large guy and I use really big toys. I find that teasing myself and then going in and out a few times helps but a very important thing that I forget sometimes too in the heat of the moment is to slowly breath out during penetration. Believe it or not that one small thing makes a huge difference. I squeeze and release while it’s in such a fun workout lol. I still feel just as tight but I can stretch and accommodate just about anything, never hurt myself. Keep practicing it’s worth it to me I have the most intense orgasms ever I can feel it through my entire body. I can sometimes find a rhythm and have myself on the edge for what feels like hours (probably just minutes lol).
