There is absolutely no reason to be embarrassed. Getting plugged is a beautiful way to make an intimate connection with someone you care deeply about. However, while I'm a firm believer in being an adventurous, open-minded partner in any sexual encounter, I am equally as convinced that it is never a good idea to do something that your gut is telling you is just plain wrong for you so first things first.

When you think about your boyfriend putting his dick in your butt, are you afraid in the Oh-no-I-think-that-bee-is-going-to-sting-me way, or in the Holy-shit-this-plane's-going-down! sort of way? If it's the big, stomach-in-knots brand of fear, then you should tell your boyfriend that while you care about him and really enjoy your sex life, mounting you is not an option and you will make it up to him in some other way that you both can agree upon. If it's more of the small, nagging variety of fear, then by all means keep reading, and I will do my best to make your foray into the world of butt-love a good one.

Many people will recommend starting out with a dildo before taking on a living, breathing partner. Personally, I've never found faux cock nearly as exciting as the real thing, and if you're not as excited, it's more difficult opening up that back door for company. Unless your boyfriend is unusually large down there, I'd say you can safely skip the toy-assisted warm up and jump right to the main event. That’s not to say you don’t need any preparation at all. At some point before the big day, you should take some alone time, get yourself nice and worked up, and slowly ease a finger (or two) up your ass. Not only will this give you a good idea of your own personal pain-to-size/thickness ratio (if there's any discomfort at all), but it will also give you a preview of what it's like to have something going in through the out door.

Assuming that doesn't kill your desire to continue with this, on the day of the big event you'll probably want to do a little spring cleaning. You can pick up a disposable enema at any drug or grocery store. (If you're too embarrassed to buy one yourself, send your boyfriend, and tell him it's his price of admission.) The directions are pretty straightforward, and in no time, you'll be all done. When the time finally arrives, make sure you both are comfortable, relaxed, and in the mood, and then get busy doing whatever it is you two do that has made your sex life great so far, making sure to go overboard on the foreplay since the more horned up you are, the easier it will be to open up and let him in.

When you feel like you're ready to make an attempt, use lots (and lots and lots) of lube. Slather it on him and on you, and don't worry about using too much. Trust me on this, you're not going to want a whole lot of friction back there your first time. As for what position to use, that's a matter of personal choice, but you'll definitely have the most control if he lays on his back and you straddle him and then slowly ease your way down onto his cock. Don't feel that you have to get him all the way inside in one try. If it starts to hurt, you can ease yourself off his cock, take a couple of slow, deep breaths, and when it feels better down there again, make another attempt at working that sucker in. Once he’s all the way up there, take a moment or two to get used to the feeling, and then you're ready to start slowly moving. A little up and down, a little back and forth, maybe a swirl or two, and there you have it; you're bottoming.

Of course, there is no one, correct way to get yourself ready for your first time getting screwed. I hope you find this helpful, but in the end follow your heart (and anus) and do whatever works best and makes you the most comfortable. If you feel you need more information (there's a lot out there), a quick search online or a trip to your local gay bookstore is a great place to start. Happy humping.