I’ve been into anal play since my late teens. I’d play with toys, ask gfs to use fingers, dildos etc. and I experienced many a great orgasm but always with cock stimulation involved.
I’d been experimenting with guys a little at the time, mainly oral fun, I had a thing for gloryholes and generally being on my knees and worshipping hung guys. A couple of guys a regularly serviced started taking an interest in my ass, they’d make me strip, bend over and eat my ass before I sucked them dry. One Sunday morning, with the hangover horn I went to one of these guys pads intent on sucking another big load out of his very thick cock.
I let myself in, undress and knelt in front of the sheet he’d set up in between a doorway. A few seconds later my favourite cock appears and I set to work pleasuring it. After a few minutes in the guy tells me to turn around and put my ass through the hole. I do as I am told and feel his tongue lick away at my hole, it feels so great, I’m moan out loud which encourages him more. Next I feel his fat finger pushing at my hole, I relax at let him finger me, he pushes hard down and finds my prostate, I moan loudly feeling precum leaking from me, a second fat finger joins the first, he’s encouraged by this and my lack of resistance.
He pulls his fingers out of me and I suddenly feel his mushroom head rubbing up and down my hole, if feels so so good, he’s wanted to fuck me for over a year now since I regularly started to suck him. He’s encouraged by my reaction, I hold my arse cheeks open so he can rub his helmet up and down my hole some more until he finally stops rubbing and just holds it against me with a little pressure, I want more and try to simulate the rubbing feeling moving my arse up and down. All this achieves is to allow his mushroom head to apply more pressure and pleasure against my hole. By fingering me he’d loosened me up and my arse was wanting more.
The guys was 8-9 inches and really thick, I’d contemplated letting his fuck me before but I was always put off by his size, I was sure he simply wouldn’t fit. In the heat of the moment I lost my inhibitions and applied backward pressure against his cock. His cock felt so good, he’s asked if ‘this was okay’ ie his cock about to enter me. I responded by relaxing, pushing back and allowing his thick hard cock to slide inside me for the first time. When I felt my ass cheeks meet his hips I paused for a moment, slightly proud of myself for accommodating such a big cock and acknowledging that there was now no turning back. I reached back underneath me to check for myself that this was real. My own cock was hard, behind that I found a big set of full balls and a couple of inches of hard cock, the rest was buried inside me. He very slowly started to thrust his hips back and forth, fucking me for the first time, as his hard cock rubbed back and forth against my prostate, I felt my body change, the feeling was overwhelming me in a way I hadn’t expected. I was moaning involuntarily, and this was encouraging the man behind me to thrust his cock into me with much more vigour, his balls were hitting my own as he built up momentum, the sound of my arse cheek slapping against his waist were too much for me, I remember visualising the beautiful big thick cock that I had spent hours sucking and worshipping in the last yea, was now buried deep inside myeloma and that any second now it would finish fucking me pump a big thick hot load of cum inside me.
A few seconds later it did, the pressure of his cum thrust took me over the edge, my arse clenched tighter around his cock, squeezing his cum out and my cum erupted all over his carpet. He kept fucking me until I was emptied, he laughed, slapped my arse and slowly pulled his spent thick cock out of me. I looked back to see his thick limp cock hanging proudly between his legs, having just cum in my arse and made my cock squirt, I got up, got dressed, embarrassingly thanked him and left…
I’ve been back again since…