Question

I recently got into a new relationship and we’re planning on having sex soon (I’m a gay male by the way). The problem is that I’m not that experienced, both with partners and toys (and condoms for that matter). I’d like some help where lube and condoms are concerned. Do you have any lubes that you’d personally recommend, preferably silicone for anal play?

Also, would you have any flavored lubes that you’d recommend? We’ve tried a bunch of cheap samples we bought at a local novelty store and they were all pretty gross. Most of them were really thick, sickly sweet, and kinda burned our mouths. We obviously don’t need them to have a good time, but sometimes it’s fun to try new things. Any suggestions would be great.

Finally, I’m not that sexually experienced and quite nervous. Do you have any tips for a first timer?

Answer

Whether it’s anal, vaginal, or otherwise, first times can be overwhelming and scary. Trust me I know, I’ve been there. At some point we all have. With that in mind, the discomfort you may encounter during first time anal sex could be minimum or very intense depending on how relaxed you are. It’s for this reason that I created a post on anal sex tips for beginners, all designed to help make things a bit more comfortable and fun. I suggest reading the full post just so you’re not missing anything. In the meantime, I’ve copied the most valuable info below.

Sh*t Happens… Sometimes.

Before I get into the how-to’s of comfortable butt play, I think it’s worth mentioning the one thing most people are afraid of… having their partner remove whatever they’ve inserted and it being covered in shit. Yes, I really did write that and I really am going there.

The truth of the matter is sometimes it happens and sometimes it doesn’t. It can be as little as a tiny speck or a lot (though that’s usually not the case), or sometimes there’s nothing at all. Diet have have an affect, as can how recently your last bowel movement was. If it’s something you’re really worried about make sure to go beforehand, don’t eat foods that you know make you feel gassy or have to go (avoid fatty, fried, and spicy food as well as caffeine), and try using a quality douche to clean yourself out.

At the end of the day any time you engage in butt play there’s a chance shit will happen. It’s normal, natural, and should be expected. Sure, it can be embarrassing but if you’re having sex with a great lover that’s mature, understanding and informed, it doesn’t have to be.

Now that that’s said and done let’s get on to questions at hand…

Before engaging in full anal penetration it’s a good idea to take some time to warm up; relaxing breathing exercises, meditating, and getting comfortable with your partner will prove helpful in the long run. Remember, the more relaxed you are the more relaxed your muscles will be. This will go a long way when it comes to inserting a toy, finger, or penis comfortably.

After you’ve added some lube, add a finger and just a finger; trying to insert a penis right off the bat can be a shock to the system. Likewise, going too fast too soon can cause you to tense up, leading to a painful experience rather then a enjoyable one. By using a finger you prep the body, stretch the muscles, and allow yourself time to get used to the feeling.

Once the finger is inserted, have your partner leave it there until you’re totally comfortable and relaxed. Tell them not to thrust or move it around… just insert it and leave it.

When you’re ready have them slowly remove the finger. Doing it quickly can cause you to tense up, so make sure to go slow. From there I suggest adding more lube and a toy. You’ll want one that’s on the smaller side, flexible, made of 100% silicone, and has a flared base like the Small Tantus Silk (pictured right). This will give you the opportunity to work up to something larger with minimal discomfort.

Whether you decide to continue with a finger, toy, or penis, have them thrust gently in the beginning. Take your time, relax into it, and try to enjoy the moment.

I know we see the people of porn taking it like champs, but they’re trained professionals. It’s what they do for a living. You’re not expected to take a pounding the first time around. It’ll likely take a few tries, or maybe you won’t ever feel comfortable doing that. Either way, it’s totally okay and normal.

If you’re partner is having a hard time inserting, try doing it doggy style. This may make it easier as you’re the one determining how far it gets inserted and at what speed. Simply have your partner on their knees staying as still as they can. Then slowly back up onto it. Once they’re inside you can find a pace and depth that’s comfortable for you.

Finally, be gentle with yourself and know that if at any time you want to stop there’s nothing wrong with that. It’s your body, you get to call the shots.