YourName2000 saidThe buttplug is a good idea, imo. I'd also suggest investing in a shower attachment anal douche --if you're fretting about something coming "out", you might be clenching as he's going in. Perhaps if you feel really confident that you're "good to go" (after a douche), you'll feel more comfortable gaping yourself open so he can slide on in. And hopefully you're doing this with a guy you like a lot, who makes you feel safe and whom you trust...any kind of nerves can make you clamp down a bit too hard in the beginning. Go slow! You've got all the time in the world to explore with the right guy. Use lots of lube. Try different positions (some guys think climbing on top of their guy and lowering themselves on his dick gives them more time/control to adjust.)
Once he's in, and he's got a few strokes into you, I personally find it easier to open up and stay "flexible", lol. So I suspect you just need help getting the party started. Being really comfortable with your butt and the fun you're about to have can really help, imo. The toys will help (that can part of the foreplay, too....he can work you over a bit with smaller toys until you're ready for the real deal.) And some people do find poppers or smoking a joint helps relax them.
It sounds to me more like nerves/tension that's making it painful for you at the start, so you're giving up. With some experience, your mind/body will just know: "we've got 90 sec of discomfort until we get used to this glorious dick....then hopefully a good 30 min of pleasure afterwards, heh heh heh." So I go back to "practice, practice, practice".
Wow, pretty much spot on!! I am doing it with my boyfriend of a year so I am comfortable with him, it is just the nerves complicating things. I have only had him try entering while I am on my back, maybe a different position will help ease things for me...very sound advice. Thanks so much!