Anonymous: Hiii everybody! I’ve been going anal only for a couple of weeks now and I have one advice for all my friends out there: Start wearing buttplugs! 😉 It makes spontaneous buttfucking sooooo much easier and pleasurable! 🙂 xoxo Linda

Thanks for the advice! It’s great advice, too: wearing a butt plug, even a small one, for extended periods of time, helps train your anal muscles and gives you increased control over them, both to tighten and to relax at will. Over time, you can gain the ability to easily jump right into spontaneous anal sex with little to no warmup and just some lube.

Plus wearing butt plugs is a lot of fun and can be really hot.

Anonymous: So I would love to perform anal on my gf, I myself like a prostate stimulator. We have used a small plug and my fingers on her, plenty of lube. All seemed well to me. She said it was painful and then told me he has hemorrhoids and was embarrassed to tell me. After the anal play they flared up and caused her discomfort and bleeding and was not fun. I would like to try again, kinda given up on my penis as girth is large, any suggestions?

Anal sex and hemorrhoids are one of those things where there’s a lot of conflicting information. Some people insist anal sex causes or makes hemorrhoids worse, while others say it’s possible to comfortably have anal with hemorrhoids or even that anal helps cure them.

In the short term, starting out, anal penetration can be physically stressful on the region while the recipient has a difficult time relaxing to allow easy entry, which may make hemorrhoids worse if it’s overdone.

In the long term however, it increases muscle control and makes it easy to relax and open up without strain, which can be a positive factor with hemorrhoids.

Ultimately, consulting a doctor and additional sources is the best approach with something like this.

Anonymous: I was never very open to anal but I recently started exploring and I’m very excited. I bought some plugs to play with until my boy can come fuck me but he’s asking about ass to mouth and having me rim him. I want to please him but I think I’m stuck on the idea that it’s risky and unclean. Thoughts?

Congratulations on your anal exploration! I hope you have a lot of fun with it.

Rimming is usually done externally only, so if you do it shortly after bathing and the recipient of the rimming cleans the area thoroughly (soaped up and well-scrubbed) there isn’t really anything unclean or dangerous about it. I think it’s only fair that you ask him to do it to you as well if you do it to him.

As for ass to mouth, many people only do that after having an enema to clean themselves out. The rectum is usually fairly clean when empty, however, and it may be perfectly fine to go ass to mouth without using an enema beforehand for some people. You’re unlikely to get sick from exposure to your own bacteria. It may be something you want to explore with a dildo or toy beforehand to see if you have any interest in it at all. If the idea doesn’t appeal to you at all after giving it a chance, don’t necessarily feel obligated to do it just because it’s something he wants.

tman79: What is a good way to train my ass to take a large and long cock?

With toys. Use butt plugs and dildos regularly, gradually increasing the size as you can comfortably do so. Avoid all pain—if it hurts, stop and rest and resume more slowly.

Extreme length can be tricky—there is a bend at the end of the rectum which has to be temporarily straightened if the object is particularly long. The best way is with a flexible dildo and to gradually press up against the bend and back off repeatedly until it gives way painlessly and opens up. Then pass the dildo back and forth through it for a while as it relaxes further.

Always warm up with a butt plug and/or dildo before attempting penetration with the real penis, and be sure to be able to comfortably fit a toy the size of the penis before trying it for the first time for real.

Anonymous: What do you think about butt-plugs? I’ve been thinking about getting one for my wife, but what size is recommended? And should they be left in just for a while before anal sex or left in most of the day for best results? Will it make much difference if thinking about getting her to make anal sex what we do most of the time? Thanks in advance for your help.

Butt plugs are amazing. She should probably be at least slightly familiar with anal play before using one—a finger or two up the butt during oral sex, and the like. If she can already take two or three fingers (or a penis) fairly comfortably, you should get about a 1.5″ diameter plug like the Tantus Ryder. There are smaller ones as well, but they don’t stay in very well, so I like 1.5″ as a minimum size. Always go for silicone, glass or steel—the other materials aren’t body safe and smell awful, even though they’re usually a bit cheaper.

You can do all sorts of fun things with butt plugs. She can wear it during oral and vaginal sex, or in preparation for anal sex. Wearing it around the house or out in public is a lot of fun as well if you enjoy the sensation of being filled anally and feel like being naughty wearing one in public.

doublemyass: Anyone have any idea of what I should stick up my ass? I’m getting tired of how small my butt plug feels 🙁

Sounds like it’s time to upgrade to a new plug. The Tantus A-Bomb is pretty amazing but somewhat large (2 ¼” at widest, 1 ¼” at neck).