As an 18-year-old Canadian gal, I feel compelled to tell you that you rock. On to business: Forgive me if this is an asinine question (how often do you hear that?), but how do I put it tactfully to my boyfriend of 1.5 years (and going alarmingly strong!) that I think I want to do him with a strap-on, in part because I'm pretty sure from things he's said that he'd enjoy it? Is there even a way to put it non-bluntly? I would rather suggest it subtly if I can. Any information regarding obtaining said object, such as prices, sizes, etc., would also be much appreciated.
Timid In Toronto
You think you want to do him in the butt with a strap-on?
Well, TIT, I think I speak for all straight boys everywhere when I say this: No straight boy is going to offer up his butt cherry to a girl who isn't completely certain that pegging his ass is something she absolutely, positively wants to do. Not something she's contemplating, TIT, not something she's mulled over. Because the last thing a straight boy wants to hear once he's face down, lubed up, and white knuckling the sides of the mattress is... "Naaaaaah, I guess not..."
Actually, that's the second-to-last thing he wants to hear. The very last thing he wants to hear is, "I didn't know there would be so much blood."
So before you broach the subject, TIT, you're going to need to commit. You need to present this idea to him with so much passion and fire that he understands that you wanna, that you gotta, fuck that beautiful little ass of his. Can you accomplish this while being tactful, non-blunt, and subtle? No, no, and no. There simply isn't a tactful, non-blunt, subtle way to tell a man—any man, porn star or virgin, gay or straight—that you want to fuck his ass. There is no comforting euphemism, no way to soften the blow. It would be easier to drop "I'm pregnant" or "You have leukemia" or "That was my dad who got arrested for fucking a dead deer by the side of the road" into a casual conversation. You're just going to have to let him have it, TIT, if you ever want to let him have it.
As for pegging supplies and equipment, check out the goods at these fine websites: *censored to make sure it's SFW but you can find it at the link*