Let me make one thing perfectly clear: I love anal pleasure.
And I'm very, very good. At both giving and receiving.
The difficulty is finding a partner with enough experience, or an open mind. Anal pleasure is probably the most misunderstood activity of adult relations, not least of all because its the least-practiced.
A.P. is more than just "butt sex", or "topping". In addition to that, it includes rimming, fingering, fisting, and toying. I have a lot of experience with all aspects. When I first began to explore my transitioning body, anal was one of my wonderful and unexpected discoveries. And I've brought this wonderful practice to countless gentlemen.
But it gets a bad rap. Largely from people who don't know what they're doing --- or haven't even tried it! Though anal pleasure has been around at least as long as genital sex, modern western society has stigmatized it to such a degree that any serious discussion first involves clearing away widespread fallacies.
"Enjoying A.P. means you're gay."
Wrong. A significant number of married and other hetero couples enjoy it, too. I've been married several times, myself (yep) and enjoyed anal relations with all my female wives. If you hear women saying "he always wants anal, he must be gay", the unspoken subtext here is "I have hang-ups about anal, so feel threatened & frustrated that men want it from me". Anal is a sexual act. That's all it is.
"Anal sex is always painful."
Also wrong. In fact, the anal-rectal region has thousands more pleasure receptors than your genitals. If it hurts, you're doing it wrong. Its not vaginal sex, so different rules apply. Also, because we've been told anything back there is "bad", you probably need to re-learn the pleasure you experienced as an infant, before the brain "shut down" such impulses during your potty training.
"The best anal sex is rough"
You've got to be kidding, right? Many straight men harbor this wild fantasy about being "taken" by a trans-woman. They have "sub" feelings, turned-on by putting their partner in control, so being virtually raped can sound exciting. This is a prime example of fantasy having nothing to do with reality. Anal pleasure requires relaxation, time, lots of lube a sensitive touch, and incredible cooperation between partners. Forced, fast, and rough has nothing to do with anal pleasure. For advice on pain, please go elsewhere.
"Its all about the prostate"
No, anal pleasure is not your family physician's digital rectal exam, and finding your prostate is not your partner's Holy Grail. The prostate is not a magic G-spot for all men. If yours is enlarged or enflamed, contact can actually be very painful. For some men, sometimes, yes, it heightens pleasure. For all, always, no.
"Bigger cocks are better for anal."
Actually, the reverse is true. A wide cock stresses both of the anal sphincters (yes, you have two) and a long toy or penis usually ends up whacking that first big bend in your sigmoid colon, causing pain and possibly injury. An experienced bottom (receiver) can eventually learn to maximize the pleasure and minimize the discomfort from a large cock, but few of us seek one for anal.
"Its no big deal to mix anal with genital and oral play". Another fallacy perpetrated by the porn industry, whose performers seem to move indiscriminately between oral, genital, and anal activity without cleaning themselves first. Bacteria from the rectum cause infections everywhere else. Its that simple. I love anal play. But its going to be the last chapter for us, not the warm-up, unless we first thoroughly wash and gargle.
Now, for the Real Thing
The back door is not like the front door. Throw away your rulebook for vaginal sex, and keep an open mind. These guidelines are a good start.
#1 You cannot use too much lube.
Vaginas make their own lubrication, the anus and rectum do not. You need plentiful amounts of a lubricating product close at hand. When in doubt, use more. More, more, more. And then some more.
#2 Once entering the back door, the front door is off limits.
The bacteria necessary to digest your food cause infections everywhere else.
#3 Anal pleasure demands a sensitive, cooperative connection between partners.
With this many nerve endings, and much of the "good stuff" rather buried out of sight, close attention helps prevent problems and maximize good vibes. Banging away absent-mindedly, not such a great idea.
Anal is usually about taking it easy allowing the receiver's body to process such new and varied pleasure. No partner has ever complained about my going too slow.
#4 Significant pleasure comes from no penetration at all.
That's right. The anal sphincter is extremely sensitive. Lightly caressed, licked or gently pressed upon with lots of lube, it can be so pleasurable as to actually accelerate the receiver's orgasm.
#5 Anal is more about width, and not depth of penetration.
Men are so hung up on the easier-to-quantify measurement of length, when in fact, its often a detriment. For the receiver, pressure against the inside of the rectal wall is what feels good, not your poking deep into the digestive tract. So its width that matters. The tricky part is, that same width can stress the anal sphincters. One good solution involves special toys, that inflate once inserted. Another involves clever use of the hand, spread inside.
Width also creates most of the pleasure for clitoral and vaginal sex, too ... a fact most men seem eager determined to ignore.
Hopefully this gives some idea how maligned anal sex has been, and what enormous potential it has. For more on this fun but misunderstood topic, watch these YouTube videos. Their content is largely accurate and the presenters knowledgeable. Most other clips on the internet are either misleading or downright wrong, and I won't vouch for them.
Laci's Guide to Butt Sex
Empowering Single Moms, Anal Sex, and Blow Jobs
(excerpted, starting near the 5 minute mark)
Her discussion of oral sex is also interesting so I've included that, too.