Open to advice, mostly venting and seeing if others have same experiences
My whole sexual life I’ve been super into anal— I’ve had multiple dildos for 10+ years that I use regularly. For several years I was using them every single day! (Get off before going to bed.) They 100% reliably get me to finish, even on nights when I’m not really feeling aroused in general & also with direct clit stimulation. When I AM already in the mood and add anal toys, I can cum almost instantly. Sometimes I can even cum with anal dildos with ZERO other stimulation! Moral of the story: I love it, I’ve always loved it, and I’m solo experienced in it.
I’ve had various partners in my past but never engaged in any penetrative sex (including PIV; i have terrible vaginismus) until my current boyfriend. I was super excited to try anal with him when we first got together because I know it’s something I enthusiastically and thoroughly enjoy! Finally, I can experience the real thing and it should be EVEN BETTER! Only… I hated it. We tried it six or so times over the course of a few months and every single time I hated it. It was extremely painful. I feel like we did everything right— lots of lube, multiple different positions tried, prepped with 2-3 fingers anywhere from 15 minutes to 35 minutes, had regular foreplay beforehand to “warm up”, etc.. Tried doing non-penis anal play during “regular” sex (like rubbing, caressing, fingering, toys) to try and get my body used to it outside of only the lead up expectation even! Without fail I found it to be too painful to enjoy to any degree, even with a vibrator, and felt so vulnerable from the penetration that I’d feel emotionally hollowed out after from the sheer shock of sensation. Even had a panic attack a couple of times. We gave up for a long time.
Eventually, we started trying again Nothing changed, really. We did all the same things we tried before, but this second run around was much more successful. We were able to do it until he finished almost every single time with little struggle… only I still didn’t like it. It wasn’t unbearable, like before, but I still didn’t enjoy it. The stretching is always wildly uncomfortable and weird and slightly painful, no matter how slow we go or often we do it or how much lube is/isn’t used. The actual penetration part is less uncomfortable than the stretching, honestly. But the thrusting? It honestly either feels like absolute nothing or feels that overwhelming-not-pain-but-shocking-too-much-sensation that isn’t pleasure and just kinda makes me tremble. And the issue is that he’s BIG. He’s seven inches so he’s very mindful to not go too deep, because it hurts BAD. But when he’s shallow it feels like nothing. But going any farther makes me so nervous that I tense up and get anxious because if he accident thrusts any harder, any faster in throws of his pleasure then suddenly I’m getting sharp, stabbing pains.
I don’t find thrusting to be pleasure anyways— I don’t even thrust when I use toys on myself. I like more of a roll/grind/back and forth wiggle action. Thrusting has never been something I find arousing, even when warmed up. Going fast/slow doesn’t help, it’s just not my thing. But he needs thrusting to enjoy it himself! Grinding/smaller motions that work for me don’t stimulate him at all and he gets soft really fast. There was ONE single time out of dozens where he seemed to have a good depth and angle and I was really, really, really getting turned on and feeling horny and enjoying how it felt but he doesn’t have the stamina to keep it going for me to be able to even get myself off while it’s happening! And sure, I can finish AFTER… but the whole fucking thing I want is to be able to get off while enjoying active anal! We tried rings of various sizes and types to see if it helped keep him hard longer but none of them really did anything. We do usually have me get off before we start because it’s almost guaranteed I won’t be able to finish during the act, and afterwards I’m usually so uncomfortable or emotionally worn out from being dissatisfied with it that I don’t even want to finish anyways.
It’s really disappointing to have something I looked forward to for years be nothing at all like I wanted or expected. I don’t understand why I love it so much solo and can’t seem to enjoy it even a decent amount no matter what we try with “the real thing.” It’s such a massive let down in my personal desires for my sex life. It’s also really frustrating because I WANT to like it because I WANT us to connect over it. I know he enjoys it and I want to be able to enjoy it with him, give myself away to him, let him have fun and have fun in return. Enjoy it together. I medically can’t have PIV so our sexual avenues are already limited, I hate that a good penetrative alternative ALSO doesn’t work. And this time not for medical reasons but for… confusing, unclear reasons?? We don’t do it anymore at all because I couldn’t keep having sex when my mind was rebelling because it knew my body didn’t like it and he didn’t like that I wasn’t having a good time consistently. (Took me a while to be honest with him.) Has anyone ever experienced a similar frustration in their sex life!?
TLDR: I enjoy anal toys immensely and have for a very long time. Never had any issue with them and would consider it my #1 kink/pleasure. Tried it with boyfriend (never done it with anyone else) dozens of times in dozens of different ways and find it to be painful, uncomfortable, anxiety-inducing, and unarousing (mix and match any of those four) without fail. Feel discontent with this outcome and resent being let down from long-time “real life anal must be even better!” fantasies. Wondering if anyone else has similar experiences or advice.