Starting with hygiene, this is a no-brainer. Anal sex shouldn't be attempted just before or after deification as there will likely be some poop in the canal. A long soapy shower or bath beforehand is always recommended and some women even prefer an enema. During that time, use your own finger to gently probe deep inside and learn how to relax when doing so. Not only does it clean the canal, the touching, rubbing, and penetration can stimulate all those sensitive nerve endings at the entrance. This can also be used as a sensual foreplay technique. My partner and I will often bathe/shower together before the main event and we take turns exploring, probing, and deeply massaging each other's private parts. There should be no fecal matter or smell afterwards. To be safe, you can go from the vagina to the anus, but not the other way around.
The second component is lubrication, lots of it. As mentioned in some of the above posts, silicon lubricants seem to work the best. The anus does not naturally produce enough lubrication for sex and you want to avoid any potential for tears or rawness that can eventually lead to subsequent pain and possible infection. Nothing will ruin the mood more than that.
This is the part where the gentlemen must pay attention and put on their listening ears! If your partner is not totally relaxed before, during, and after anal sex, it may be your last session. Any guy who watches mainstream porn to learn about anal sex will fail, period. We have all seen clips where the guy with a monstrous penis forcibly plunges his manhood inside while the woman withers about in fake ecstasy. Trust me fellows, this is acting by paid performers and has nothing to do with an erotic pleasurable encounter.
Long anal foreplay is best served with massaging and light probing starting with the tongue and then progressing to a finger. Allow the woman to relax and enjoy the sensations. Listen carefully to her body language and moans and don't be afraid to ask questions along the way. Trust me, if she is enjoying your technique, you can expect more in the future. Once you are both "ready", try some vaginal penetration first (but never after you have penetrated her anus).
This next part is the most important guys especially if you are trying anal for the first time. Always remember, the woman has full control over position, penetration, depth, and rhythm. Let her find the most comfortable technique and go at her speed. Usually, the penetration of the penis head is the most critical stage. Allow her to push the head inside without you thrusting. Once the head slips inside, let her get used to the feeling. She will push down once she is ready and not before. If one technique doesn't work, transition into a different position.
Before I met my current partner, I had anal sex a few times and always hated the experience. It was painful, unsatisfying, and not pleasurable in the slightest. We were together almost 4 years with the topic of anal sex never being discussed. Sure, he would tease my rosebud with his tongue, mouth and fingers during foreplay, but it never progressed to full penetration with his penis.
I'll never forget the first time we had anal sex. That night we had hours of great passion. Loads of foreplay at first and just about every position imaginable. I lost count how many orgasms I had and we both passed out exhausted without even cleaning up afterwards. I remember waking up early that morning from an erotic dream. I must have been masturbating in my sleep since my ***** was drenched from our mixed juices from hours before and my fingers were soaked. I quietly continued my self-pleasure and started probing my rosebud. I was so sensitive at the time, I could feel an orgasm building.
My partner was still sleeping on his back at the time but he had a partial erection (must be the morning pee thing, lol). At that time I couldn't help myself as I got closer to massage his balls and stroke his shaft. I then replaced my hands with my mouth and it didn't take long for him to become fully erect. By that time, he was partially awake but too tired to do anything but lay back motionless and enjoy my work.
I'm not sure what got over me at that time, but I climbed on top of him and started rubbing his engorged head against my rosebud. It took very little pressure before it slipped inside. No pain, no fear, and my insatiable desire to have more increased. By the time he was fully inside with just me controlling the rhythm, I had the first of many orgasms. I had no idea what I was missing until then. Since that infamous morning, anal sex in all positions has become an incredible new addition to our sex lives.
I hope this helps some of the hesitant people out there. This still doesn't mean anal sex is for everyone. But if there is any chance of enjoying this sensation, all the elements discussed is paramount.
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