Have you ever come across someone who is excited by the idea of strap-on training but can't seem to relax enough for it to "work?" I'm that guy, I am so excited by it that it's virtually the only porn I watch any more, and yet when I have the opportunity it is just painful, and it makes me feel like I need to use the bathroom. I've tried everything, extra foreplay, going to the bathroom beforehand (of course) but nothing seems to help. I have had times when I've gotten past that and eventually loosened up enough to enjoy it but those times are infrequent and unpredictable.
You don't say how large your strap-on equipment is...I would recommend no bigger than 6" long and 1.25" diameter.
Loosening up enough to enjoy it can be largely emotional. Do you meditate? Consider working with some positive visualizations. Picture yourself relaxing, opening up and enjoying it just as much as you do in your fantasies.
Then start to include anal play with smaller items such as fingers and smaller toys every time you have sex...not followed by pegging. Have your partner use her finger to search for and find your prostate, with verbal guidance from you. The prostate is a spot that sometimes takes repeated stimulating to sort of wake it up and teach you the kind of sensations it gives, which are very different than penile stimulation.
The feeling of having to go to the bathroom is common in the beginning and doesn't last. That is what your anus is programmed to do - signal that you have to go to the bathroom when there is something in your rectum - completely natural. But almost all men report that the sensation doesn't happen every time after they get more familiar with pegging.
Get used to doing the anal play on a regular basis and then try the pegging, with a reasonable sized dildo, of course.
If you drink, a glass of wine might help, too.
Good luck to you!
I use the Share. I really like the idea of the woman being physically stimulated in the act, that really turns me on. It's a bit thick, and it gets thicker as it goes in, but the real problem is right at entry.
I don't drink, so that's not an option. I meditate a bit, and that does help, I mean, imagining her in me when she's inserting seems to help. I don't have a girlfriend so my opportunities are limited, and I'm very private about this so it's not something that I go out and create opportunities around.
Thank you for your advice.
You say the problem is at entry. When the toy is entering you, make sure you bear down exactly as if you are having a bowel movement - push as if to evacuate your bowels. That allows your anus to open up. The anus is programmed to open when there is something inside that needs to come out. So opening would not happen automatically if there is something outside that wants to come in - you must consciously push down.
Sometimes the best way to learn about your body is by yourself. Can you practice with the Share on yourself? And if it is still too difficult - you need to get a smaller toy and work up to the Share. They sell dildos that have suction cup bases that can be attached to a shower wall, for example. That way you can find out what works the best, what feels good and what doesn't. Once you get used to pleasing yourself, you will be more ready to explore it with a partner.
I hope that helps...