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Its been two years since i first did that insertion and i can now get something like 22-26 up. Im a big man tall that is and have been fascinated by trying to take large objects in my anus for years i know there have been larger objects taking but to date i think the largest ive managed would probably have to be a bowling pin not the big. Most people cant do the splits without a lot of stretching and training first turns out its the same for stretching your anus. Dear alice, i have encountered a problem i never expected my boyfriend is quite simply very large. I am unable to perform oral sex except for the first couple of inches due to the girth, and vaginal sex is not totally satisfying for him because he is too long and cannot fully penetrate without causing me significant pain.   anal sex is a bit of a taboo subject, despite the fact that its an increasingly popular sexual activity. As more couples explore this type of sex, understanding the risks, rewards, and proper. Anal herpes anal sex may spread the herpes viruses hsv-1 and hsv-2. Symptoms include painful sores around the anus that come and go. No need to be embarassed! Understand that the rectum is not a straight line, but is curved. Its not only curved, its kind of curved twice if the anatomy of your rectum from a side view was a map, wed essentially go in from the anus, take a left, take a right, then go up again towards the right. So, whats possible is that your partner is hitting one of those walls, and either a) you two.