After reaching middle age, I can say that I’ve got a fairly healthy relationship with my cock.

It’s not the biggest (a very average 6”), and it’s had only a handful of complements for its looks, but I can honestly say that I seem to have the perfect cock for anal.

This is the trilogy of the three girls where my cock was the first to open up previously uncharted anal territory.

The first girl was Erica. And she was my first, too. How sweet.

As a first year uni student, Erica was quietly confident, or determined, to expand her horizons, in bed. As a first year university student, I was totally incapable of picking up very obvious signals. So when, one day, as I was lightly stroking her she said “You know, some girls prefer anal” I didn’t really register anything other than a useful fact to be stored away for use in pub quizzes.

It took another couple of months for her to get to the point. As I was waiting in her room for her to get ready to go to the college bar, she came right out with it: “I want to try anal”.

Reader, that was the longest two hours I have ever spent in a bar.

Ok, so forgive us for inexperience here. And this was before easy internet access, so we were own our own in figuring out the plumbing. But after we got back to her room, and clothes were thrown off (and folded of course - we are not animals), and we’d warmed up a bit, she turned to me, looked up with her utterly innocent face and said “why don’t you try putting a finger in my bum so I can get used to it”. So as we continued to kiss, she placed my fingers (yes, they are long) on her hole, and as I pressed, she wriggled and squirmed as we both worked it into her. A slight sigh as it went in, followed by more gentle grinding to take the first, and then the second knuckle into the tightest place in her tiny frame. We must have spent fifteen minutes just kissing as she got used to the feeling of my unmoving finger in her, just giving in the occasional squeeze.

After a while, she wordlessly rolled onto her stomach, turned away from me and presented her (ever so slightly open) arse towards me.

“So,” said Erica. “Shall we try?”

I did not need more encouragement. With spit and her own wetness as our only lube, we placed my cock on her, and gently built up some pressure. It must have been a sight. Me: large rugby playing 19 year old, still powerfully built at six foot. Her: tiny curly haired brunette, doe eyes, high cheekbones on an innocent face, five foot nothing and elf like. But she was determined. So for every quantum of pressure I applied, she pushed back with three, until finally she opened and in, slowly, I slid. And once I was in her, Erica was the one who took the lead in her mission to lose her anal virginity, and to get me my brown wings. Reverse grinding to take me in. Then circles, up and around, her arse pushing into me, her head buried in her pillow, until the excitement got too much (probably mercifully quickly) and for the first time, she had her arse completely filled with cum.

After a slow withdrawal, she shuffled off to the bathroom, one had trying in vain to keep the cum in her arse.

“How was it for you?” I asked.

“I do now feel like I desperately need to poo - but I am enjoying that feeling”

I couldn’t have asked for more.