My girlfriend and I are interested in getting into toys and anal play for both of us. Where do I start? I need some advice.
Learning how to enjoy anal sex requires a certain amount of patience. Vaginal intercourse ís all about thrusting in and out. But anal penetration requires periods of waiting. Remember that the lower bowel is conditioned to react to fullness by contracting and voiding waste. Too much stimulation will thus be uncomfortable, especially to the beginner. You are gradually easing a well-lubricated finger, cock, or toy into an orifice that is tense and very sensitive. To avoid uncomfortable cramping, it ís important to slow down. It can feel very good to insert a bit more, stop and wait for the anus and rectum to relax, then proceed with a bit more insertion. Simple pressure feels good. The weight of what one contains is an intense sensation. A subtle bit of movement can cause waves of physical feelings.
Begin your exploration of anal sex by taking showers together. Get clean and playful. Massage the lower back and buttocks. Get everything in the area nicely warmed up and relaxed. Then put some lubricant on a gloved hand, rub it into your fingers to let it warm up, and stimulate the OUTSIDE of the orifice. Don't penetrate until your partner is practically begging you to go on. Then follow the above instructions for gradually training the rectum and anus to relax and accept erotic sensations. We all carry a lot of shame, tension, and anger in our assholes. This part of the body has often been the object of pain and shame. It needs comfort and affirmation and appreciation. Make a no-pain contract with your bum. If you try to tense up and "power through" anal sex, it's bound to hurt, and the next time you try it, that sphincter will be screwed shut even tighter.
Most people don't like poop, even though elimination is an important natural function that we need to say healthy. The poet Muriel Rukeyser referred to "our useful shit ... a clear clue to what we need," but she was pretty advanced on other issues too. To quote my friend, the recently deceased sex radical Steven Brown, "Shit is a substance not unlike mud, and can be made to go away with a brisk application of running water." Most waste is stored above the rectum. You aren't likely to encounter any shit if you are simply fingering or putting a cock or dildo into the ass, unless your partner hasn't had a good bowel movement that day. Some people feel that they can't proceed to enjoy anal sex without an enema; other people find that enemas are not a great form of foreplay.
If you want to see if an enema can enhance your sex play, buy a water bottle with an enema hose and nozzle attachment at the pharmacy. Use tepid water. Cold water will cause cramping. Use lubricant, insert the nozzle, and allow the water to flow out slowly. You'll have to pinch the hose to slow the water down. When your partner has had enough, he or she should perch on the throne, and evacuate. Walk around a bit afterward to allow any water that's left over to come down and be expelled. The colon has a few bends in it, and water can go far enough in to go past these bends, in which case it takes longer to come out. You don't have to go for repeated bouts with the hose unless your excrement is unusually prolific. Getting an enema makes some people feel tired, and the process itself takes a minimum of half an hour, so allow some extra time for this. Don't add anything to the enema water like mineral oil or wine, and do not use commercial prefilled enema bottles; they are extremely irritating.
You'll be able to tell when you are ready for anal intercourse with a strap-on or a penis when you feel relaxed enough to be able to tolerate penetration by three fingers. Before that, you can try wearing a small anal plug to promote relaxation. It can feel really good to wear an anal plug while you're having intercourse (for either one of you). People tend to buy dildos that are too big, especially the first time around. Remember that you can use a small one for every occasion; but a large one is for special times. So get something that will always fit; it'll be the mainstay of your toy box.
Your girlfriend need not buy a dildo harness unless she wants the experience of fucking you hands-free (and you also want to see what this is like). She can certainly use a dildo or assplug just by holding it in her hand. But if she does want a harness, try to get one that can be cleaned in between use. Lube will get on it. I think a two-strap model is more comfortable, but if she is used to wearing a thong, the harnesses that feature one strap up the back may be just fine. You will probably enjoy anal sex more with something that is longer than a finger. A dildo is more likely to reach and gently stimulate your prostate.
The advice I gave you for fingering the ass goes double for intercourse. Going slow in the beginning will yield big dividends of pleasure in the future. Wearing a condom might help cut down on sensation and help you to last longer. It will also protect your urethra from any germs that might be lurking in her colon.
Good hygiene is important when you start getting into anal play. Be careful not to get anal bacteria or other problematic things into the vagina. It's best to have separate toys for vaginal and anal use. Use condoms on all your toys to keep them clean. Remove condoms and wash them with soap and hot water before re-use. For finger and hand play, use gloves. Take them off and wash your hands after anal play. The same thing goes for your cock. Take off the condom, wash off your dick, and use a new condom before entering her vagina.
Talk to each other while you explore these new parts of your bodies. The person who is being fondled or penetrated can speak erotically about how they are feeling, or ask for a different kind of touch, or request a break. The one who is doing the touching can talk about what this means to them, how beautiful the other one is, and what they would like their partner to experience physically and emotionally. Take time to breathe together, and enjoy! The myth that anal sex is dirty and painful simply isn't true. With a few reasonable precautions and a decent helping of sensuality, it can be a wonderful way to bond, come, and reclaim your body from the harpies of Puritanism.