Fucked at a gloryhole
I lost my anal virginity at a gloryhole. Although I’m married I was curious for a long time and used to wank watching shemale porn, then Sissy Hypno, then it was gay porn. Once that wasn’t enough I used to flirt with guys online until I once was on a night out, some guy hit on my and I thought ‘fuck it, I’ll blame it on being drunk.’ We went back to his place and we’re kissing and I sucked him off in the shower. It was absolutely incredible. If you’ve ever been curious, just try it, it’s better than you can imagine. Anyway. This was a one off and nothing similar ever happened again but I imagine it while fucking my wife now. Fast forward a few years, again I’m drunk on a night out and hoping some guy would hit on me but no one did. Being horny and drunk I decided to go to a known gloryhole on my way to get an uber home. I’ve been here before to watch but this time this unbelievable dick came through. It was massive and looked like it came straight out of a porn video. At first I just looked at it until the voice on the other side got annoyed. Before he took it back out I wrapped my hand round it and tried to fit it in my mouth. It was pretty hard to fit in my mouth so I ended up licking it up and down and sucking His balls a bit. Next thing I know, he pulls it out, I hear some movement and it comes back with a condom on. Being in the mood and drunk I thought ‘fuck it, I’ll blame it on being drunk.’ I pulled my trousers down fully and spread my legs and backed up. Next thing I know his cock head it pressing against my asshole and with about 5 minutes of trying and pressing my ass gave way and this huge cock slid in. I have to admit, it was fucking agony at first. So so painful. I’d fingered my ass before but this felt like it was ripping me in half. I didn’t move a muscle for what felt like forever and then all of a sudden I felt him push in to me slowly, then out, then back in. My ass was accepting his meat and slowly the pain was fading. 10 minutes later he was at full speed and groaning a lot, then with a strong deep thrust I felt his balls slap against me as he came deep inside me.
He slid back out, left me feeling hollow and that was that.
I blamed my walking and sitting the next day on a heavy gym session so my wife didn’t suspect a thing.
And that’s the story of my anal virginity.