For me, anal was like a Holy Grail quest, but my first "win" was kind of weird and didn't end well.
The first time I succeeded in buggering, I was working as a DJ at a radio station during the summer of 1999. This girl used to call every DJ, every day, flirting, talking dirty, asking the guys about their cocks, the girls about the their pussies, and generally teasing us all.
I should have guessed that she had some psychological issues, but at the time, it had been about six months since I had "snapped the bean" and I was getting itchy. By early August I was really getting bothered. It was hot as blazzing balls and no amount of jerking could compensate for the balls and shaft's urgent need for pussy/ass. That day, I walked into the studio about ten minutes early and heard Sammy, the guy on before me, talking to the girl (honestly, I can't remember her name). He had her on the studio speaker phone and was interacting with her just enough to keep her going, but he was only doing it because he was bored and was amused by the act of leading her own.
I flirted with her throughout my shift. I could tell that she was a little bit touched in the head, but over the phone she didn't sound like the straightjacket type. By the end of my shift, I was ready to thump my rod on the control board, I mean it was so stiff that a cat couldn't scratch it and I knew that going home and jacking off wouldn't solve the problem. What’s-her-face was going to have chip in for the good of Hank's jewels. I snagged her phone number, planning a rendezvous for later that afternoon.
At about 2:30 PM, I called and she said that she was home alone and free for the afternoon. She gave me directions to her apartment and told me to bring a pint of whiskey.
Here I went, Jim Bean, brown-bagged, in hand, to her apartment, which was a glorified dorm room on campus. I hadn't ever seen her before and this was in the day before Facebook, so I was somewhat nervous about what would answer the door. I figured that if the door opened and I was confronted by a horrifyingly hideous creature, I could simply walk away. After all, it wasn't as if I knew her or had to work or go to school with her, so who cared?
She wasn't especially attractive, but no dog, either. She was a brunette with slight curls and soft, white skin that had a few freckles, but not enough to write home about. When I showed up, there really was only one thing on my mind, so as long as her looks didn't make achieving that objective impossible, I was ready for anything, even a whale.
I walked right in, handed her a swig of whiskey, and began stroking her hips. We were close enough that she could feel my erection bump her upper abdomen from my swollen pants. She reached down and felt it though my pants and I looked her straight in the eye and told her to take me to her bedroom so I could fuck her.
By this point, my cock was so turgid that it had become painful, though it was an erotic pain. I took her clothes off, laid her on the bed and began licking her large nipples as I stroked her pussy, trying to get it wet enough for action. Soon, I was sliding my cock inside her hairy pussy. During the missionary style pounding, she took a phone call from her boyfriend and talked to him. I suppose that I should have been unnerved, but I didn't give a damn, I wasn't there to date her and the idea of her boyfriend being forced to talk to her while some guy he never met was slamming his cock into her gash made me all the more excited.
As I stroked, I held her wrists down, looked her straight in the eye and proudly announced that I was about to put my shaft in her ass. To my surprise, her eyes lit up and she said "OK, but hang on." She left the bed and returned with a bottle of I Can’t Believe It's Not Butter, which she suggested that we press into service in lieu of lube. I sprayed liquid butter all over her spider hole and my member. With her asshole buttered like a Cracker Barrell biscuit, I slid my shaft into her tail hole: no fingers, no relaxation techniques, no nothing, just a guy she called on the radio sticking his prong up her choot while she talked to her boyfriend on the phone.
Who would have guessed that spray butter, used as lube, would burn? I hadn't stroked her rose more than five times before I had to withdraw and wash the little man. I returned with the intent of giving her a nice, old-fashioned cream pie, but she seemed to have pass out soon after I mounted her (too much whiskey), so I stopped my buggering and took my leave.
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