All my first time anal experiences.

First time anal stories are usually always hard to tell. Sometimes the story is all about how the guy’s cock was too big, or they didn’t use enough lube. Luckily, I played with my own ass before any other guy did. I was a naughty little kid so I started experimenting early! Everyone has funny stories about when they first started playing with themselves. I know guys that have gotten caught red-handed, girls that used toys that they shouldn’t have. I was a dirty-minded child already, and very curious. On top of that, my bedroom TV had access to one of the Playboy channels, when they aired amateur porn videos in the middle of the afternoon.

Hell, I even had my own laptop to play with. All I ever did was play games and do homework on it, but sometimes I got curious and started looking things up. After enough Googling, toy experiments, and playing with my own fingers, I branched out. One of my funniest involves a banana. Sometimes I even joke about it to you guys, when you ask about my first time anal stories. Sometimes I skip right to the first real cock I took, but I have many more stories before that, with my own toys. I was a curious 14-year-old, looking at online forums and websites. I knew I was a little deviant.

I’ve always liked sex and there was no denying that.

However, I wasn’t ready to fuck somebody yet, or even get the guts to let them that close to my pussy or ass. With such a curious nature, I’d definitely been lightly playing with myself for a while. After enough comments and research, I’d gotten really curious about anal. There were these ‘truth or dare’ websites that I loved to frequent, and my friends always made little comments about it too. The boys were all super-horny all the time, so they always cracked jokes about fucking their girlfriend’s asses. Let’s face it, they weren’t really getting laid yet. However, I just grew even more curious.

I saw someone suggest that I use a banana for the first time anal, just to try it out. What they failed to mention, though, was that it should be a frozen banana. It would have been a helpful tip because no amount of lube was going to get a soft banana into my virgin ass. It squished on one of my many attempts to slide it in. I kept stubbornly trying to stretch my big teen ass with my own fingers, spreading my cheeks and everything. However, nothing worked to make me a little looser. So I called it quits. I left my poor, un-fucked ass alone, and threw the squished, useless banana away.

I was just a teen, so I couldn’t go to the store and buy a dildo.

All I had was cash, so I couldn’t even order one online. The next time, though, I used something a little easier to play with. I had plenty of lotion bottles, lipsticks, lipglosses, and much more. After a little experimentation and picking out a small bottle, I licked the end of it and sucked on it a little, getting it nice and wet. Then, I pushed on it a little, then a little more. My ass was complaining and sore after I’d tried to get so many different toys inside it. However, I needed it badly.

With how hard it was to try to slide the toy in, was a little scared of how much force I’d have to use. On top of that, I feared that I would slide the toy in too fast once I got past the barrier. Once I got it in, though, I kind of liked it. My ass felt full and stretched out, and I knew I wanted more of it. After all, I wanted to fuck my pussy as well, and I’d only experimented with first time anal so far. Two weeks passed and I finally started dropping hints to my boyfriend.

He was a big, black football player in high school.

I’d been dating him for about a year, ever since I was a freshman in high school. The guy was tall, aggressive, and attractive. He hit almost every checkbox and requirement that I ever had. To put it simply: he was my type, and I’ve had the same type for my entire life. I have a thing for black guys and big black cock. Luckily for me, he took my virginity and allowed me to really experience first time anal with a big cock. I should have let him be the first to play with me, honestly. However, I hadn’t met him yet when I tried all those horrible experiments with lotion bottles and bananas – LOL

Regardless of all my crazy childhood experiments that I’d never admit to someone I personally know.. I’ve had plenty of fun experiences, and I regret none of it. Hell, after all of it, it’s really opened my mind up to the world of fetish phone sex.

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