Angelic posting, hope everyone is having a great day/weekend!
Oriens and I have been getting into anal recently. Its been months really, though we normally only 'try' two days in a row before getting side tracked. Its hard at times to find alone time, because we are a same sex couple living with her Baptist mother, so everything is very hush hush as she just thinks we are friends!

I'm not sure if the problem if that we are doing it so infrequently, or if I need to suck it up and take it, or if we're just not doing something right. I bought some glass toys off EF months ago, and I LOVE the glass beads we got (link) I can take them no problem.

But What I'm aiming for is to take it up the ass from her while she is using the Realdoe (link).

Now the first time we tried getting the realdoe in was after anal play- she used her fingers first, lots of lube, then the toy for a bit. Admittedly I got impatient and begged for her to stick it in- I think I got maybe the full head in before she had to pull out because it hurt SO bad.

The most recent try, we took more time. Fingers, and the beads again- then I tired to get this plug in, which I bought together with the beads (link) and again I had the same problem.
It hurt to much, had to stop- and I was sad.

Are there any tips you guys can give us on what to do? We use astroglide gel, and I do LOVE having something in my ass. I WANT to do more, but its like I hit that pain wall. Any help would be wonderful D: less

My advice would be to spend a little more time warming up. Glass toys have absolutely no give, so I suggest buying something a little softer. Perhaps try something soft/silicone with just a slightly larger circumference than your beads, like about 1 1/4".

I've heard really good things about the Ryder. You can even keep it in for a few hours in your free time, just to get used to the feeling of being stretched. less

My advice... patience. It sounds like you are on the right track with experimenting and loosening up. But it sound like you just get worked up and eager, and that's when it goes wrong. It sucks... I know, I've been there and been so disappointed. I don't think the length of time between sex will make too much of a difference. I think that learning a few tricks will help avoid some of the missteps of anal.

Warming up and slowly working up to the size you want is key. Take incremental steps and resist the urge to take a toy in all at once. When moving up to the next size of toy resist the urge to rush it and instead just play around for a little while. As I have gotten more experienced I have found I can relax quicker and this doesn't take as long, but early on it was key for me.

The cobalt bubble plug is not an insignificant size of toy. Take advantage of the tapered part and just play with the tip for a long while. Then start playing with a little more of it and play for a good while. And so on. When some people are working up to a new toy size they can often spend a lot of time just playing with it before it will go in comfortably. Sometimes that can take multiple play sessions. It gets easier over time but it takes a while before the body get used to it.

Also, you may try warming up the temp of the toys slightly. This may be challenging under the in-law's roof. I find that sometimes when toys are cold (especially glass) can cause the muscles to involuntarily clench up. When the muscles do that during anal play it is bound to be uncomfortable. If you can you may want to try running the toys under some luke warm water. Body temperature is what you are aiming for. It doesn't take too much to warm them up and if they are too hot that is not going to be comfortable either.

If it were me, I would spend a lot of time experimenting and playing with the cobalt to loosen up before the realdoe. When playing with the realdoe it will probably involve more thrusting, and that is something that will be much more enjoyable if warmed up and stretched a little.

I hope some of this might be useful in getting past the uncomfortable part of anal and on to the good stuff. Good luck. less

Slow down and enjoy the sensations. Getting use to bigger toys will take time and there is no sense in rushing things. Why Not has some great advice.

You might also try have an orgasm before the anal play, for a lot of women this helps to relax which will make anal play much easier. Also, you might try inserting the toy yourself at first. Even after all 23 years with the wife I find it hard to relax when she is driving the toy on me. I can use a 1 3/4" toy to warm up with by myself but I have to use a 1 1/4" toy when she uses it on me at first. There is nothing wrong with this, it's just the driver cannot feel what is going on so going too fast is easier to do. less