The question came totally out of the blue. My boyfriend, Dean*, and I were laying in bed together after having sex when he turned to me.
"I’ve been wondering how you feel about...anal sex?" he asked.
My stomach dropped. It was a question I’d been dreading.
"It’s not happening," I replied quickly.
Even the thought of it terrified me.
MM Confessions: The weirdest place I've had sex. Post continues below.
From the grin on Dean’s face, I knew this wasn’t the last time he’d bring it up. And, just as I’d thought, it cropped up again a few months later. When Dean would casually bring it up, I'd firmly shut him down.
Then, one day, we were shopping when a Mulberry bag caught my eye.
Picking it up and admiring its perfect stitching, I sighed. Unfortunately, the two-grand price tag was out of my reach.
"I can get it for you if you want?" Dean offered.
Dean had always been generous with his money, showering me with gifts, but none as expensive as this.
"I can't let you do that," I said. "It's way too expensive."
"We'll put it in the bank of anal," he said.
My eyes narrowed.
"What's the bank of anal?" I asked.
"I need to get my money back somehow," he joked.
I decided to accept his offer, even though I had no intention of ever paying off my anal debt.
Over the next few months, whenever we were out shopping, or out for dinner and drinks, Dean would pay for everything and add it to the "anal account".
Then one night after dinner, I suddenly got the urge to repay the debt.
I figured why not give it a try? I could obviously stop at any point if I changed my mind.
So when we were getting down to business, the words I never thought I'd say came tumbling out.
"Okay, we can do anal," I said.
His face lit up like he’d just won the lottery.
"This is the day ever," he said.
Though it did nothing in particular for me, it wasn't as bad as I thought it would be and I actually enjoyed trying something new.
"That was amazing," Dean said after, with a huge grin he couldn't wipe from his face.
"I wouldn't get used to it," I said. "That's the bank empty now."
Over time, the anal bank value built up again, and every time I felt like it had reached a reasonable limit, I put it back on the table.
We did it another handful of times before Dean and I sadly broke up and went our separate ways.
When I started dating a new guy, Tim*, he casually brought up the possibility of anal sex a few months in.
"You couldn't afford it, hun," I told him, before explaining the bank of anal.
"The only way is to pay."
He dropped it, but the topic came up again a few months later when were on holiday in Bali.
"Okay, how much?" Tim asked.
When I realised he was being serious, I gave it some thought.
"How about $400?" he suggested.
"I'm worth more than that," I scoffed.
After a lengthy discussion, we agreed on $600. He pulled out his phone and transferred the money into my account on the spot.
"Tomorrow is the day," I said with a wink.
The next morning, Tim woke up like it was Christmas Day.
"I already can't wait until bedtime," he grinned.
We headed down to the pool, and with his mood elevated, Tim started knocking back the cocktails.
By the time we got home that evening, he was stumbling and could barely navigate to bed so we were both out like a light the second our heads hit the pillow.
"We're going to have to schedule another day," Tim said the next morning.
"Nope, you had your chance and blew it," I said.
His face looked like an injured puppy's, so we found another day to do the deed.
It was the first and last time we did it, as we broke up shortly after. As it turned out, mine wasn't the only arse Tim was interested in.
Not wanting to rush into another relationship, I settled into single-girl life for a while.
Then I was on a night out with my friends when I met Matt*.
He owned a restaurant in Sydney, and after a night of compliments and charm, we ended up back at his.
We were in the middle of the good old-fashioned sex when he bent down and whispered in my ear: "I'd love to do anal with you".
It seemed I couldn't get away from it!
"I'm afraid nothing goes in there for free," I told him and explained that he'd need to pay.
"Okay, how much do you want?" he asked.
"Well, I charged my ex 600, but I'll do you a deal for 500," I said.
"Done," he replied.
True to his word, he transferred the money from his restaurant's account rather than his personal one. I still wonder to do this day what he said to his accountant when the transaction was flagged up.
I don't know when I'll have it again, but I know it won't be free!
*Names have been changed.
This author is known to Mamamia, but has chosen to remain anonymous for privacy.
Feature image: Getty.