My sex life has been pretty bad lately. I've been single for over a year, and even before that, I'd say that at best my sexual prowess would be considered "vanilla" - and that's giving me some credit that I probably don't deserve.
Let me give you some back story. I'm a gay man who's doing far less than my dirty mind would like to be doing. Yeah, I've had some anonymous sex, dark parking lot blowjobs, and been with two different guys in the same 24-hour period, but that's really not much. I'm a bottom and really enjoy sex, but am not the most outgoing person, reducing my chances of hooking up or meeting people. My escapades of late have been limited to enormous amounts of porn and furious masturbation.
Lately, however, I've been watching a lot of anal play, and honestly, its been a turn on. About a month ago, I started playing more and more with my ass as I masturbate, 1 finger, then 2, then 3. It felt amazing, but it was one night while watching ass fisting videos that my interest completely changed.
I saw how hot it looked to be fisted, and watched huge cum shots from it, and suddenly I found myself infatuated with my ass, playing with it at every chance I get, and really working hard at stretching and opening myself up. I wanted to get to the point that I was able to insert huge, massive dildos into my ass, and fist myself entirely. I knew it would be difficult, but I was up for the challenge!
Every morning in the shower I would begin, soaping up my ass and 4-finger fucking myself to really open it up. After about a week, I was able to insert my shampoo bottle up my ass, using breathing techniques and rectal pushes and different angles to get it in. When it "popped" in, I felt so proud of my achievement, and so incredibly full. My legs were wobbling, and my ass felt stretched to the point of tearing, but I kept at it. I was limp, but started masturbating, and even soft, I had an earth-shattering orgasm. I nearly fell over from the effects of my weak legs, lightheadedness, and full body convulsions. I was in heaven, my ass felt amazing. I was blissful and couldn't wait to do it again.
If I had extra time in the morning before work, I'd finger my ass, working on getting all four deep, and even moving on to the fisting attempt of all five fingers, in the duck beak position, jamming it in and out of my ass. I felt so open, so alive. Gaping myself was exhilarating.
I've been using makeshift dildos, but it was apparent that I moved beyond them and needed something real and serious. I finally gathered up the nerve to visit the adult toy shop a few towns over. It was mid-afternoon on a Saturday. I walked right over to the walk of dildos and began my investigation. I was looking for something thick, long and realistic. I found a great 9" long, 2.25" wide black dildo that took my breath away. I grabbed a tube of water-based lube and practically ran to the register to pay. On my way out, there was a dildo on display that had to be 3 feet long and as round as a 2 liter soda bottle. I said to myself that one day I'd be purchasing that (and I'm determined to do so!).
I drove straight home, tore open the packaging, liberally lubed my ass and my new dildo up well, suctioned it to the floor, and immediately began riding it. I felt my eyes roll into the back of my skull - this purchase was perfect. The dildo felt so life-like, filled me up so well, and penetrated me so deeply. I didn't want to stop. I figured I could ride this until one of us broke.
As I figured, about 2 weeks later, I wanted something bigger. Back to the adult toy store I ventured, but this time it was late on a Saturday night, and the place had a totally different vibe to it. It was packed with tons of different people; couples, singles, groups, you name it. I walked over to the dildo section and found a massive dildo called an "Ass Stretcher". It looked like a miniature pylon, designed to stretch the ass excessively. I grabbed it, and a 12" long, 3" wide dildo and headed over to the counter.
The guy at the counter remembered me from my first visit. He made a comment about my upgrade in the dildo size and when he saw me "Ass Stretcher" he grinned at me. He asked me how much of it I thought I could get inside me, and I said maybe half, but looking to get the whole thing in at some point.
He stepped back from the register, looked me up and down, then stepped forward, leaned in and whispered to me that he'd love to see my try it out. I was a bit surprised, not quite sure what he meant or if he was even serious. He must have noticed the blank stare on my face, because he chuckled and again whispered that there is an employee room in the back, if I could hang around a few minutes, he'd take me back there so we could "talk".
Suddenly, I was a ball of nerves. I so badly wanted to, but my inexperience in this area nearly caused me to vomit. I muttered out an ok, and proceeded to stroll about the store trying to kill some time, carrying my bag of goodies alongside me. I got caught up checking out the anal sex videos when I felt a tap on the shoulder. The cashier was next to me, smiling, and led me to the employee room.
He was on a platform behind the register, but even in person, he was a big, tall man. Black, handsome and quite masculine. I followed him to the employee room, blushing as people watched me, probably assuming in some way this guy was going to have his way with me.
The employee room was part office, part break room, with a throw rug and a couch along one side, facing televisions connected to the in-store cameras. We both sat down, and I didn't know what to do next. He chuckled again, and told me to take it easy, no pressure. He asked to see the "Ass Stretcher" and when I handed it to him, he began to tear open the packaging, handing it back to me. I just stared at him, then he told me to lube it up.
I fumbled with the bottle of lube, nervous at all hell, and when I was done, i put it on the floor in front of us and just stared at it. It was massive, and I was suddenly starting to think I bit off more than I could chew. He suggested I take my clothes off, assuring me nobody would interrupt us.
