Tristan Taormino's Anal Sex 201

After I did an interview (part 1, part 2) with the lovely Tristan Taormino earlier this week, we headed over the Tristan's workshop at Early to Bed (makers of Special Delivery), on Anal Sex 201. Now I admit I hadn't been through Anal Sex 101 yet, but after reading Tristan's books and watching her videos on anal sex, I'm pretty sure I was prepared for it. Even Tristan announced at the start of the seminar that she expected us all to "have a working knowledge of the ass." Yes, ma'am!

Her first tutorial was on enemas, a topic she sometimes gives entire workshops on, but is a good starting point for preparing the ass for anal sex. If only all those submissive men I fucked with strap-ons during my domme days were only so prepared! There's several different types of enemas you can get, but she warned that if you buy one of those store bought (Fleet) enemas, you must dump out all the contents in in beforehand. Store-bought enemas contain a laxative, and in order to avoid a big mess, replace the contents of the enema with plain warm water and keep squirting until all that comes out of you is clear water. Then you're clean. You can also buy your own personal, re-usable enema bag if you're a real professional, but make sure not to share it with anyone and always use warm, not cold, water in order to avoid cramping. She also mentioned that you should do the enema two hours before doing anal, not right before, as a "second wave" can always come along, and you really don't want that to happen during sex. I would think not, but then, how many people prepare for anal sex that far in advance? It's a little tricky, but good to know.

Next she went into the various toys that are good for anal play. Flexible materials, such as silicone or rubber toys are good for beginners, whereas glass, wood, and other harder materials work well for the anal pros. However, sometimes the toys of harder materials are easier to insert, and glass toys I've found are really nice because of their smoothness. As far as how big a toy is...it's all about getting past the sphincter muscles. if you can get the recipient to relax better, the larger the toy you can get in their ass. Length of toy all depends on the person. Most people have 10-12 inches of rectum, anything larger can get into the lower transverse colon and well, I've never been able to get anyone to take something that long myself. But hey, it all takes practice.

Now if you really want to prepare your ass for anal, you gotta start with butt plugs. Tristan likes butt plugs because they go in and stay in and she even has a plug she designed herself that's named after her (which we later learned she was wearing that night). They're a fun way to warm your ass up for anal and you can wear them for extended amounts of time, though she mentioned 6 hours as a cut-off point for most people. Use one of soft and flexible material, such as silicone and make sure to use water-based lube for extended wear. Silicone based lubricant is incompatible with silicone toys and will ruin the toy unless you put a condom on it first. The longer you leave a butt plug in, the more relaxed your ass will be and the more prepared you will be for anal penetration. She also showed us several butt plus harnesses, which work similar to dildo harnesses, that help keep your butt plug in place for long-term wear without popping out.

As far as strap-ons go, Tristan recommended "the mistress", a purple, skinny, medium sized dildo for first-time strap-on play. It was just small enough to not be intimidating, but large enough to work the ass up to larger toys. Shorter, curved dildos hit the g-spot for women and double headed curved dildos are perfect for girl-girl, vag-to-anal fucking.

Next up came to the anal positions demo, where me and my friend Kimberlee were chose to be the live models! She had us get up and demonstrate all sorts of positions such as the reverse cowgirl (woman on top, facing away from man), the tailgate (I forget this one, but it was a little complicated), the yab-yum (something that involves tantra), and several others. It was a bit awkward for me, but funny and helpful for the participants, which some of them told us after the demo. Anything to help!

She then went on to talk about actually "getting it in", which is something most people do wrong when it comes to anal. It's best never to "stuff" the cock in, as the sphincter muscles are too tight. One should just insert the tip of the cock in to start off and never force it in. Let the recipient control how much they receive of the cock (or dildo) by bearing down, as if they were pushing something out. To put it bluntly, you should act like you're taking a shit, but of course, you're not. Most women may need clitoral stimulation in order for anal to feel good and oftentimes it's best to have an orgasm before you even try anal, as your muscles are already relaxed by then. Also, men may lose their erection when on the receiving end of anal, as they are relaxing so much as there is nothing to support the erection.

As Tristan always insists, anal sex should never hurt, but I'd be willing to believe that most people would disagree with that. She says one should =never have to work through the pain to get to the pleasure, though, and if it hurts, stop. Most pain is caused by not properly lubing up the ass or preparing it for anal. I'm sure we've all head the stories from guys who "stuck it in the wrong hole" as a way to initiate anal sex, but this should never happen! Anal sex can't be rushed and lube must be used no matter who the recipient is.

Finally, she concluded the presentation on a subject that usually makes some of us a little queasy...fisting. Now the thought of putting my hand up someone's ass or someone putting theirs up mine is just not one that brings pleasurable thoughts to me, but obviously lots of people disagree and enjoy this act. Tristan does warn that this act takes a lot of patience and although in certain circles it is common to take "poppers" or other drugs, she recommends doing it totally sober. Obviously, the recipient here absolutely must have an enema before engaging in fisting and the fister should wear a glove no matter what. I sure as hell wouldn't want to shake the hand of the one that doesn't! Butt plugs with a wide base are best to use for warm up here. I seem to remember reviewing a butt plug here at SK called the "Big Red" that would be just perfect for warming up to a fisting session. Thicker lube such as Astroglide or a thicker silicone lube work nicely and always remember to use more lube when removing the hand!

Ok, enough of that...

Several people asked Tristan questions, the first being about double penetration (where ass and vagina are penetrated at the same time). She says there's two ways to go about it, but the most popular involves putting something in the ass first, whether it be cock or dildo, and then working something into the vagina. The other way is to insert little by little in each hole, a little in the ass, a little in pussy until they are both completely penetrated.

Next a guy mentioned that his chiropractor hates him because every time he gets fisted, his back gets tweaked. This one had Tristan stumped! She'd never heard of this issue before, but was willing to research it and get back to the guy about ways he could prevent it. Well, I have to imagine it probably has something to do with the intensity of the fisting and the size of the fist going in, but hey, I'm no expert.

Lastly, my friend Jack posed the question we all wanted to know. What butt plug was Tristan wearing at that moment?

Why of course, the "Tristan", the butt plug designed by and named after her.

Now how many of us will ever have the honor of having any sex toy, let alone a butt plug, named after us?

Tristan's a legend, and rightly so.