I've typed and re-typed this 4 times now. I'm having trouble putting my thoughts into words that flow and make sense. So, I'm just going to post this and let y'all read it.
WARNING, the following words are graphic descriptions of anal play that my wife and I engage in. So if you don't want to read about that, might want to hit the back button.
I think you either like anal stimulation, or you don't. I do. I still struggle with embarrassment about it. I guess I can't get over the societal "gay" stigma associated with men and anal sex. I'm not gay or bisexual at all. The thought of being naked around another man is revolting to me. My wife indulges my anal fetish about once a month. She used to joke with me about being gay, but I had a heart-to-heart with her about it and explained that those types of comments were very hard for me to deal with, since I struggle with the fact that I enjoy stuffing things up my ass and the whole society stigma. She was understanding and has never made another comment of that nature. She just switched her teasing and verbal humiliation to other things related to a guy sticking things up his ass.
My fetish started when I was a teenager. I would insert various cylindrical objects into my ass and masturbate. I never had the guts to ask any of the girls I dated in my teens and early 20's to engage in anal play. I met my wife when I was 28. After about 6-8 months of discovering our kinky side together, I finally felt comfortable enough to ask her if she would use a dildo or strapon with me. She practically left a vapor trail, speeding like a maniac, to the adult toy store to buy one. We went home and had our first anal encounter with me being on the receiving end.
It's been a downhill slide into debachery since then.
Somebody mentioned that thrusting can be irritating. It certainly can be. I find it's better to start with a small dildo and go very slowly. Initially, thrusting shouldn't even be considered. We just focus on slowly inserting and lubing until I am VERY relaxed. It can take anwhere from half hour to an hour of slowly stretching with progressively larger and larger dildos before I am relaxed enough to enjoy any thrusting. My wife has learned over the years that I enjoy the strecthing and the feeling of fullness more than any vigorous thrusting. I don't mind slow/medium thrusting with a medium dildo - 2" diameter or less, but my wife can rarely stop there. She always has to "go for the gold" so to speak, and work me up to one of the largest in our collection, then pound the hell out of me. I like being stretched with dildos up to 2.75" diameter, but she gets off watching me go batshit when she thrusts a large dildo into me hard and fast. I don't really like being pounded hard and fast with a 2.75" dildo, but the flip side, is that will almost always cause me to have an explosive orgasm and shoot 3 or 4 feet into the air. So, it's sort of a catch 22 for me. She enjoys "destroying" my ass with a big dildo and heavy thrusting. I don't really like it, but I love the orgasm. We don't do that every time. Some times, I just can't take that much, since we only do this once a month or sometimes it's 2 months between these sessions. Thats a long time to recover from the last time, so I'm not loose/relaxed and ready to go for the largest toy in our collection every time. Sometimes a 2" diameter dildo is all I can stand. I'll admit that I do kinda like it when she works me up to the largest in our collection and pounds the living daylights out of me. I think I just enjoy the power exchange - I like being 'taken' and abused for her pleasure. And believe me, when a woman is pounding the hell out of you with a 12" long x 2.75" diameter dildo - you feel abused. I'm almost always securely tied up and unable to wiggle away or escape. I can't help feeling guilty and sorta dirty about it later. Mentally, it just feels wrong. I'm a guy and guys aren't supposed to like that kind of stuff. But physically I don't have the will power to say "no" when she suggests a night of anal play and threatens to pound the hell out of me.
We always use TONS of lube. I prefer J-Lube because it can be mixed to any consistency you desire, and it's extremely slippery. You can shake powdered J-Lube onto toys and then spritz them with water. That will provide very good lubrication because the lubricant sticks to the toys much better that way. Use that technique in combination with a squeeze bottle of lube already mixed with water.
Hope that wasn't too graphic or TMI for very many of you.
