Dear Mistress Maeve,
I always wondered what it would be like to have a woman take me anally - I had read that stimulation of the male prostate is very pleasurable. Last fall I was dating a woman who brought up an interest in trying it. She already owned a "double-ended" dildo, so we gave that a try. She used plenty of lube and worked it in gradually, but part way in, I experienced a sharp pain. Different angles did not seem to solve the issue. Her "instrument" was not exactly small, but given the ways that women have been able to take me anally (I'm larger than her toy), size alone seems like it may not be the issue. So, what was going wrong, and what should we have done differently?
Dear Always Exploring,
Kudos to you for enjoying anal stimulation. Some men who have sex with women balk when a lady knocks at their back door because they are afraid to be vulnerable, afraid it may hurt or afraid it will mean they're "gay" (which is a level of ridiculous I don't have time to get into here).
While I can't say for sure what went wrong, the discomfort may have come from the dildo passing through your second set of sphincter muscles (yes, we all have two). If you're not fully relaxed, moving through that second ring can be painful. Or, perhaps your partner's dildo caused an abrasion to the sensitive lining of your rectum. Remember, the rectum is not a long stretch of straight highway; it's more like a curvy mountain road - and everyone's curves are different. Make sure you're using toys made of flexible material that will curve with your body. Next time, you might ask your partner to use a strap-on, rather than a double-headed toy; a dildo with harness will give her more control. Finally, always use a condom; not only is it safer, but it will ensure the toy has a smooth surface for easier penetration.
Don't let this one bump on the road stop you from trying anal again. If you're hesitant to give it another go, try playing with a smaller toy or butt plug. The male prostate is located only about a half inch into the rectum, so, once again - size doesn't matter.
Backing you up,