During our conversation, she brought up that she has never tried anal. We ended up not going into it, but later I realized that she might have been asking for advice.
It also brought up memories that of how anti-gay my state-school-provided sex ed really was. (There was no mention of homosexuality, and my teacher referred to anal sex as being demeaning towards women.)
The following is designated to be a virgin's guide to anal sex. Essentially I came up with this as the cheat sheets that I wish I had a few years ago. Hopefully you can find it useful whether you're gay or straight.
But if I ever have to give my sage like guidance and boil it down into one sentence, it would be:
Masturbate with a dildo before trying anal sex; also think about getting poppers if you find it difficult to relax.
The Forewords:
1. I have a prostate; women tend not to have those. From my personal experience, anal sex is enjoyable because of my prostate. If you don't have a prostate, I don't know if you will enjoy it. All I can offer is years of learning and experience. Please keep an open mind.
2. If you don't want to do anal, you won't enjoy it. There is no "fake it 'til you make it": only pain. Related to that point, if you don't feel well on a particular day, don't do it. It might be painful, or you just might shit on a dude.
3. If you want to try it, you will need to prepare: not just for the first time, but every time.
4. I don't have a vagina, but I know that it's not vaginal sex. Respect the anus for what it's worth. That means don't just start shoving shit up there. Make sure your partner understands that anal sex is a shared gift (I don't know if there is a word to describe what I mean), but it is not an entitlement. Your partner does not deserve sex; they do not need sex; they are allowed to have sex with you. They need to be gentle, understanding, a good listener, and appreciative of your needs.
Basic Sex Ed
Hygiene:
1. Poop. Yes, scat comes out of the anus. To really enjoy anal sex, you'll need to poop before you do it. I usually need 15 minutes to "reset" afterwards.
2. Wipe down. I use wet wipes to get extra clean. Some people warn to avoid wipes with alcohol or fragrance but I've never had a problem.
3. Douche. Or not. I'm not a doctor; I don't know if this is bad for your body. I have done this; it helps me feel like I'm not going to poop on my partner. If you douche, you need to give your body a chance to rebuild the mucus lining on your colon. It's recommended that you wait 2 hours afterwards to have sex.
4. Take a shower. Do I need to explain this one. It will also help relax you. Brush your teeth, put on deodorant, and wear fresh undies (in my experience, this ones more for the guys.)
5. Keep tissues by the bedside.
6. Choose a hand for lubricating your anus and toys, and a hand specifically for your genitals.
Protection:
1. Condoms every time!
2. Even if you are monogamous, you still can get a number of infections; so, always wear a condom. Allergic to latex: latex free condoms. You don't like how they smell: orange scented condoms. Your partner doesn't like how it feels on their cock: internal condoms. You like a little pizazz in your display: colored condoms.
3. Condoms every time! (Change condoms if you decide to change orifice.)
Lubrication:
1. Lubrication is as necessary of a component for safer sex as is a condom. Condoms fail without condom safe lubrication. Silicone is my preference as it doesn't get absorbed by the skin. If I am masturbating, I use a water-based lubricant because I use a silicone toy. You will need to stop at some point and reapply lube because it will be absorbed by the rectum. NEVER USE AN OIL BASED LUBE! It will destroy the condom; it can also lead to an infection on its own.
2. Have you ever had a sunburn on the inside of your rectum? That's what anal sex feels like without enough lubrication. So to recap; lube is necessary for enjoyment and safety.
3. Do you have enough lubrication? The answer is, if you're asking that question, you do not have enough lube.
4. Treat yourself! The better the lube; the better the experience. Find a brand you love and always keep it with you. (I have a bug-out bag for one night stands complete with my favorite lube, condoms, and toothbrush.)
What Your High School Instructor Didn't Teach You:
Masturbation:
1. Before even trying anal sex, masturbate by yourself. You need to learn the mechanics of anal sex before you should even consider letting someone into your body. Masturbation also allows you to find out what is and what isn't enjoyable.
2. Get as turned on as you possibly can. For me, I turn on sexy music, I light candles, I turn on porn, and I sniff poppers. (For straight reads, poppers are nitrite compounds that are inhaled. Do not drink them. Do not use them with alcohol or Viagra. Open the cap and sniff the vapors. Don't get the solution on your skin as it burns. If you're going to do them, try them before hand to understand how it will affect your body. It instantly relaxes my anus, and honestly makes me lose my mind while having sex.) Oh yes, also relax.
3. Start small and simple, and move on from there. If a particular toy comes in three sizes go with the small one. I prefer a dildo that I can ride while stimulating my other genitals; some people prefer a plug that stays in place while they stimulate their genitals. I would also suggest starting with a toy that lacks texture or ridges while learning your body.
4. Use a non-porous silicone toy. It's easy to clean. With a larger toy, I finger myself first, before moving to the larger toy.
Entrance:
1. Relax.
2. Push out. One method is to clench your anus for 15 seconds, until you can't hold it any longer and then push out. (This is where learning your body with a toy helps.)
3. Breathe out.
4. Take control. Especially if it is your first time, control the pace of entry, either controlling your partner with your hand or pushing yourself back into their cock. If there is minor pain, readjust your position. Sometimes it helps to pull out and try it again. If pain continues, stop.
Once again this is why masturbating first helps. If there is pain, you either need more lube, more foreplay, or you need to just flat out stop.
Position:
1. There is no right answer, but the right position for you will make a world of difference.
2. I prefer being on top as it gives me greater control of pacing and timing. I am more likely to orgasm when it is appropriate when I'm on top.
3. If you are comfortable enough to continue having sex, explore and find your position.
TL; DR- Masturbate with a dildo before trying anal sex; also think about getting poppers if you find it difficult to relax.
Additional Reading:
1. Dangerouslilly.com on silicone toys.
2. Vice.com on poppers.
3. Goaskalice.columbia.edu on lube.
Liam '16
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