I’ll admit I’m a little weird. But, I’m not hurting anyone, and everyone has fun, so why not, right?
It started when I was really young, playing doctor with my brother. I got a rather excited kick out it, especially when he’d have me get on all fours and ‘examine’ my asshole.
Then in school, we had a sex education day. For the most part, it was pretty ridiculuous, with a somewhat embarrassed teacher telling us boring stuff we already knew, and a whole class of kids tittering and carrying on. The only good part was where we all got bananas and condoms, and had to practice putting them on. The teacher then handed out a second condom to each kid, both the girls and the boys, and told them they were ours to keep, and use if needed. How weird is that?
The teacher said one little thing that I found particularly interesting. I doubt it affected the other kids in the same way. She said the girls should get hand mirrors to look at their vaginas, and both girls and boys could use hand mirrors to become familiar with their own anuses.
Oddly, I was greatly affected by that. When I got home, I couldn’t wait to grab my mother’s mirror, get naked in my room, and look at my asshole. I didn’t care that much about my pussy – I don’t know why, but really wanted to see my asshole. And when I saw it, I went nuts. Well not entirely. It just struck a chord in me, and I masturbated something silly, giving myself two orgasms in a row. That’s the first time I ever had two like that. I didn’t even know it was possible.
So now, the image of my anus was permanently front and center in my mind. I decided to take it step further. Although it was difficult to get the angle right, I took a picture of my ass on my phone. Over the next several days, I studied that picture over and over, for minutes at a time.
I started to want others to see my butthole. It took a few days to figure out what to do. I tried it on my brother first. When my parents and sister were out, I knocked on his door and asked, “Hey Kyle, I’m worried about something.”
“Yeah, what?” he asked, evidently annoyed.
“Well…” I hadn’t expected it to be so hard to ask. I decided it was now or never. “I don’t think my anus looks quite right. Will you take a look?”
“What’s wrong with it?”
Oops, I hadn’t thought that far ahead. What should I tell him? I couldn’t hesitate long, or he might know something was up. Finally, I got an idea. “It itches.”
“Why bother me with that? Go ask Mom or Dad.” he replied, but his voice was oddly squeaky.
“I can’t. Too embarrassing. Remember when we used to play doctor, like a hundred years ago? Well, you’ve already seen it, so what’s the big deal?”
“Oh alright, pull your pants down.” he said a little too quickly.
I did just that, and with them bunched around my ankles, I hobbled over to his rolling office chair, facing away from him. I felt him touch my ass with both hands, and gently pull my cheeks apart. That alone, was absolutely amazing. What a feeling! And the cool little puff of a breeze from his air conditioner suddenly blowing against my anus – to die for!
“I can’t see anything. Here, why don’t you take your shorts off, and get on your hands and knees on my bed.”
Without a word, I complied. I didn’t trust my voice. It would have come out all shaky.
He got behind me, and looked and looked. I was in heaven!
Finally, he said, “I don’t see anything wrong. You say it itches?”
“Let me know if this itches.” and with that, he started ever so gently rubbing his finger around my anus. Oh my god! Then, he started pressing his fingertip right into the middle. Just a little bit, but that was enough for me. I was orgasming. I don’t think he noticed, or if he did, he didn’t say anything.
“I guess not,” was all I stupidly said. For some reason, I was suddenly embarrassed. I grabbed my undies and shorts, put them back on, thanked him, and left his room. I heard him setting the lock on his door behind me. I didn’t realize it then, but he must have masturbated as soon as I left.
Next, I wanted my mother to look. I told her it itched. She said, “Put some cream on it,” and that was that. I couldn’t work the conversation around to asking her to actually take a look without seeming too weird.
OK, so there was my father. I told him my anus itched. He said that was something to bring to my mother, and went back to reading his tablet.
Now who? It took me days to realize I could ask Becky, my best friend. Why I didn’t think of her right off the bat, I don’t know. I found her sexy in a way. Goofy I know, but I’m just telling the unvarnished truth here. But how to bring it up? How in the world could I get Becky to look at my asshole? Oh my god, just thinking of her looking at it had me wanking away in my bedroom.
I realized what I had to do. I just had to come out with the itchy ploy, and hope for the best. What’s the worst she could do?
She could call me a ‘perv.’ She could tell a teacher, or her parents! Bad idea. My heart jumped into my throat.
A few days later, my horniness overcame me. We were in my bedroom. I squirmed around on the edge of my bed, hoping to make it look like I was dealing with an itchy butt. She fell for it. “What’s up with all that squirming?”
“My butt itches.” – OK, I came right out with it. My heart started racing. What was she going to do?
Well, what she did was totally unexpected. “Maybe I should take a look.”
I couldn’t believe I was hearing that. She offered! I pretended to be all embarrassed and shy, because I didn’t want her to think I was weird, but I went a little too far with the pretense. She said, “OK, then,” and left me hanging there, butt-unseen. I was so disappointed. If only I had not pretended to be shy to quite that degree.
We returned to our homework, or so I thought. While I was doing a math thing on my tablet, she was doing something on hers. She turned to me, holding up the tablet, and showed me a full-screen picture of a slightly hairy anus! Hanging below the anus, was a pair of testicles. She said, “Does yours look like this?”
Bang! Instant horniness! Thinking quickly, I answered, “Not quite like that. But I wonder if I have a rash or something?”
“So, you want me to look after all?”
“Yeah, I guess so,” I said, feigning moderate indifference.
A minute later, my school skirt and panties were off. I was laying on the bed, and my best friend Becky was spreading my ass cheeks and looking at my anus. Heaven!
You could have knocked me over with a feather with what she said next. “Mmm, it smells nice.”
I know I shouldn’t have, but I was thinking with my ovaries, not my brain when I answered, “I wonder if yours smells like that?”
About five minutes later a fly on the wall would have seen two naked girls, hugging, kissing, and rolling around on my bed. We explored not only our anuses in great detail that day, but our pussies, too. It turns out that as excited as I am by showing my anus, Becky just loves having her peehole seen. That’s right. She wanted me to spread her slippery inner labia and look at her peehole. Who knew?
On another occasion, we experimented with me looking at her peehole while she tried to let out a single drop of urine. To our amusement, that didn’t work out too well. She splashed me right in the face with a big squirt. It took us several practice sessions before she could let out a single drop of pee. But it’s something we had to learn, right?
One time, we got in the bathtub. I was on all fours, and she was sort of half-standing over me. She peed right on my anus. Taking it a step further, I tried to kind of hold it open so she could pee inside. We managed to do that a little bit. It turns out to be difficult to relax your asshole enough that you can hold it open. That’s especially true if you’re in a bathtub, reaching around to your own butt. It hurts your knees.
The rest of high school was quite a bit different than the beginning. That’s because for my next trick, I started ‘accidentally’ showing pictures of my anus on my cellphone. I’d let people see pictures of my dog, my house, or something like that, and either they’d scroll and find the next picture was my naked butt, or I’d scroll and go “Oops!” faking great embarrassment. This opened great conversations that almost always led to fooling around.
It was more boys than girls, although I enjoyed both. Some of the boys wanted to fuck, but I managed to keep it to just showing my ass, or maybe giving them a handjob until my first days of college.
I rather liked giving handjobs. One day, this guy, Juan, invited me to his house after school. It was a short walk. He assured me both his parents work. His older brothers were out working, so the house would be empty. I knew Juan fairly well from school, but I was still nervous. One hears stories about being alone with guys.
He was a perfect gentleman. We went through the actions of me showing him my butt, and I was all set to give him a handjob. I was even considering giving him a blowjob, something I had never done, but instead he instructed me to lay on the bed. He started rubbing my anus very lightly, as if he knew exactly what I wanted. He spit on his finger, and pressed it part way into my anus. I felt an orgasm coming on, but he pulled his finger back out.
He excused himself, and came back with a bottle of alcohol, and a tube of something. He coated his finger in alcohol, then put some cream on all the fingers of his right hand. Instructing me to roll over, he placed a finger against my labia. I wasn’t sure I wanted that. After all, I’m an anus freak, right? But his finger actually felt rather nice. I didn’t say anything. He kept just lightly touching my labia. Soon, his fingertip was entering my virgin pussy, and soon after that, there were two fingers all the way in there as I was orgasming over and over.
I don’t know where he learned it, but he was curling his fingers around and rubbing what I later came to know as my G-spot. Oh my, oh my! It was the best feeling in my life. But he wasn’t done. While he was doing that, he snuck the index finger of his left hand under my butt, and penetrated my ass all the way with that. Orgasm City!
Juan and I became an item until we went off to separate colleges. In college, my horizons have expanded. First, I learned all about intercourse. Fucking is great! However, for me it always has to start off by the guy looking at my asshole. I don’t know why, but I’m not going to fight it. I still really love people seeing that. I have also experienced anal intercourse, Oh, it’s lots of fun, no doubt, but still, when I can get a guy, or a girl, to just look in between my spread butt cheeks, and just study my asshole, I’m in heaven.