Like my two previous stories this one also happened with my ex girlfriend

To set a bit of the scene my ex I will call her F, was initially a really shy and timid girl but after our first couple of times she started to become really kinky, she started having all sorts of ideas she wanted to turn real, but we never really had the chance for it, since we were rarely alone in the house when together. She was also never able to take all of my dick (18.2x13.5/7.1x5.3) This was always a point of frustration for her, but she took it in stride and we found other ways to make our sex as good as it can be. This was one time where one of her ideas backfired on her a bit.

It was a regular saturday evening and just like every week we spend the weekend together. We were originally planning to watch a movie together, but as things usually go for couples in love, we didn't really care for the movie after some time, leading us into a classic couple makeout session, or at least as close to a makeout session you can get when your kissing skills are among the worst known to mankind like mine.

Eventually we were sitting there both just in underwear and then F said "Hey, wanna try something new for a change" I responded "Well what do you have in mind" And then she asked "Do you want to try anal with me?". The idea certainly threw me for a loop, because with how much she was already struggling taking me normally, I was against the idea initially, arguing that there was no way it could work, and that she would only hurt herself trying. But she was adamant on trying it out, trying to make her arguments about having cleaned up expecially for me more convincing with relentless teasing, I eventually agreed under the condition that we would use copious amounts of lube and stop if she felt any pain.

So after agreeing and an extremely generous lubing up session, we decided it would be best for her to be on top for this and went for it. For the first minute or so she tried putting it in slowly and gently, but it just didn't work, not even a little. Eventually she started to get a little frustrated and pushed down harder, still nothing. She then told me to grab her hips and try to pull her down a little. I was very reluctant in trying but helped along as well as I could until finally with her pushing and me pulling, my tip plopped in. And let me tell you it wasn't nice for either of us, I felt a painfully tight squeeze at my glans and she yelped and shot back up.

We looked at each other and before I was able to ask her if she was okay, she burst out into laughter, even though I was concerned for her, her laughter was too infectious and I ended up laughing alongside her. Once we finally composed ourselves and stopped driving eachother back into a giggle frenzy, she finally said "well at least we tried" I agreed with her. "Another idea down the drain" she sighed, "if only I wasn't so small". I retorted "I think the issue lies more with me being too big". She glanced in my direction "speaking of big, you're still having quite the big throbs over there" she said while pointing between my legs. I quickly said "I don't think that should matter right now it will calm down on it's own later" I stood up and tried to grab my clothes, but she stopped me "who said we're done?" she grinned "I'm not the kind of girl who teases and then leaves her boyfriend pent up"

We then proceeded to have sex in our usual manner. Afterwards we agreed that anal would not be a thing we should go for again in the future.

PSA: I'm not some kind of expert, but I still want to remind everyone. No matter what size you or your partners penis may be, anal especially requires lots and lots of prep, make sure the communication with your partner is on point and inform yourself properly before attempting it. So that even if it doesn't go as expected maybe you can at least get a good laugh out of it.