Last year I left a dead end relationship and shortly thereafter bought a one way ticket to Australia. This sudden change in life had me soaking in the exciting possibilities to come. I had been living in a hostel in Melbourne for weeks now and while it was a fun type of lifestyle I found myself desperately longing for a bed that wasn’t shared with multiple other travelers. I needed space, and lord knows I needed a good lay.
That’s when I found myself calling Ben* (names have been obviously changed for protection of privacy.) I’ll be honest when I say that Ben was kind of a douche. I met him through friends of friends from back in LA. and he was one of those guys who would boast publicly about all the women he’s been with and interrupt the convo of friends to show a crazy tinder conversation he had going on. The first night I met him, as I left the restaurant he hollered “If you ever want to fuck call me!” as i hopped into the taxi (gross.) He was quite attractive though and tall, had that thick Aussie accent and a nice apartment strictly to himself with a pet dog. A full package for a backpacker who was sort of living like a bum and who was also incredibly hungover. So I shot him a text and asked him what he was doing. He invited me over for dinner (couldn’t turn that down) and next thing you know I’m on a tram headed towards his house.
Immediately into the hangs I made a mental note to not do anything sexual with him. My mind was made up and our snoringly awful conversations thus far had me falling asleep, but he prepared a delicious steak dinner with 2 bottles of wine and as the glasses kept pouring I found myself edging on the border of No-way-town and okay-just-this-once-ville. We began making out on the sofa while watching Daria. It had been months since I had any sort of male interaction so I was shockingly enjoying myself more than expected. Kisses led to grinding, grinding led to erections and next thing you know we were headed to his bedroom. On his bed, clothing was being removed on each party. As I reached into his pants I felt, what most resembled some kind of fleshy anaconda. I knew Australia was known for it’s snakes but by god, I was sitting on a big one. As foreplay commenced, it was already well known to both me and my vagina that this massive cock wasn’t going to come inside me very easy.
“Do you have lube?” I asked.
“Yeah in the bedside table.” he said, ocker AF.
I pulled open the drawer and that’s when I came across a gold mine of sex toys including handcuffs, ball gags, cock rings, butt plugs and of course, the one object I pulled out immediately.
It looked like a big black strap on dildo.
“It’s a strap on dildo.” he said.
“For who?” I asked and that’s when I got the most magical response one could ever ask for.
“For me. Wanna try?”
That’s when I wasted absolutely no time strapping that baby on.
I lubed it up, he grabbed onto the bedpost in doggy-style position and …….well……. I fucked him in the ass. This magical moment was over as soon as it began and he came in almost 4 thrusts. Then I went to sleep. I woke up the next morning naked with his dog wedged in between us and a slight pounding headache. I put on my clothing from the night before and began the long trudge home on foot where I felt both excited and confused. I see him around from time to time, but no further sexual encounters or pegging is to be reported, just a great memory to cherish forever.
- Karen Holland