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About getting past my gag reflex while giving blow jobs: I have no idea what's the best way to practice this. I've tried bananas, but honestly that was just weird. I never bothered trying to deep-throat my ex because he was happy with a hand job. The new boyfriend has expressed much interest in it, and I think trying to deep-throat without practice first would be really awful. Any books on this? Recommended dildos? Anything?
Willing but Worried
Indeed, but first let's get our terms straight: Are you confutf8g the standard-issue blow job with the X-treme sport called "deep-throating" (taking the penis all the way into the throat), or has the boyfriend specifically requested the latter? "Deep-throating" has long had its place in the lexicon, but it has not replaced and ought not to replace "blow job," "giving head," or "going down on." They are not at all the same thing.
If all you two are interested in is mouth-penis contact, you shouldn't need a textbook or a night of, you should pardon the expression, "cramming." You can practice a bit with nothing fancier or more banana-flavored than your own finger or a popsicle stick, just to determine how far back you can tolerate an oral foreign body before you need to expel it. It does get easier with practice. Once you graduate to the real thing, you will find that the more control you take over the process (you do the moving, he just lies there being happy he has a penis), the less gaggy you will feel. If it still feels overly intrusive or out of control, wrap your hand (spit into it generously first, as though sealing a bargain) around the base and move this in concert with your mouth. Some men can easily detect the difference but many don't care — friction is friction, after all, and warm, wet, and deep are usually good enough without having to get all picky about it. Most men enjoy a blow job, period, and few — I cannot say "none," but let's not get distracted by the corner cases — get off on making girls gag or produce involuntary Roman showers.
If you can imagine yourself practicing on a dildo and not immediately collapse in giggles, you're ahead of the game and I give you my blessing. Buy something realistically sized and inexpensive (jelly rubber, probably), pretend it's attached to your boyfriend (the sillier the color the harder this is to carry off, I imagine) and see how deep, fast, et cetera, you can go without gagging. Keeping your neck straight and head slightly back are supposed to help, although the often recommended lie-on-your-back-with-your-head-off-the-edge-of-the-bed position strikes me as ill advised at best, since we are trying to avoid panic here, and what could be more panic inducing than having your airway and vocal capability cut off while somebody straddles your chest? Try lying prone or crouching, with the dildo upright as though projecting jauntily from your boyfriend's pelvis as he lies on his back, and practice opening your throat as though chugging a beer or saying "Ah."
You may find, in time, that you really can control your gag reflex. The feedback provided by a real live boyfriend, though, in the form of appreciative gasps and groans, is a motivator the likes of which mere plastic, no matter how colorful, will never achieve. Not, at any rate, with today's technology. Androids and replicants haven't yet started rolling off the assembly lines and into our toy boxes.
Faking it with inanimate objects will only get you so far; if you really want to learn, you're going to have to try it on the real thing. I don't know your boyfriend, but I bet he'd be game for a little experimentation. Just make sure that the session is approached as an experiment, and that neither of you brings to it unrealistic expectations of immediate, spectacular success. Nobody's born knowing how to do this sort of thing, at least not until those replicants get here.
If you two get this far and wish to — oh heck, there's no better way to put this — go a little deeper, there's good information to be found in instructional videos and DVDs, like the ones Nina Hartley puts out, and in books such as Violet Blue's The Ultimate Guide to Fellatio, which contains nifty tips like how to keep your lipstick perfect throughout, as well as, yes, bona fide deep-throating techniques. I think deep-throating is overrated, myself, but then, I only borrow a penis and ought to defer here to those who possess them full time.
One last word of warning: Yes, there can be a somewhat unpleasant surprise at the end of a successful blow job. Inform him that he is responsible for early warning and withdrawal, no "whoopsies" allowed. This probably ought to be considered nonnegotiable at the beginning, subject to later review.
Andrea Nemerson has spent the last 14 years as a sex educator and an instructor of sex educators. She is currently preparing to give birth; thus, we'll be rerunning some of her favorite columns from adventures past until she recovers. Visit www.altsexcolumn.com  to view more archived columns.