This is the real story of my cheating life. Everything has been recorded in journals since I was a teenager and I’ve been spending some time going through them and asking some of the people involved to tell me as closes as possible what they remember.

These stories start when I was sixteen, about to take my first exams to get into college (in Brazil some students can choose to take three exams three years in a row, instead of just at the end of high school) and continue all the way to the present. Now I’m twenty-three and still can’t stop, and don’t want to stop cheating.

I apologize in advance for my English. I’m a Brazilian woman with advanced but not superb English so the writing style will be quite simple. My vocabulary is not very extensive enough so I might make some mistakes.

At school, I always used any excuse I found to be around boys: Contact Sports, Dance, Theater, whatever. At 5’00” and 100” I was a popular little blond gymnast for a few years, but I lost interest so that I could grind on boys in sports like Brazilian jiu-jitsu. I studied in a private school, which is not such a privilege for the very rich like it is in the US. Yeah, the poor can’t make it, but most of us middle class could. It wasn’t the fanciest school, but it had decent facilities and students of all economic and ethnic backgrounds.

I had a small group of friends of roughly eight students who would hang out together most of the time since my junior year. We’d study, have fun, party and eventually drink and smoke weed together.  We also started our sexual lives together and, for the girls in the group, it was also the start of our cheating lives.

My first kiss took place in my junior year with one of the boys in the group, Bruno. He was the cutest little thing. Very handsome blonde with a boyish face and great smile.  He was just a tiny bit taller than me, also white and skinny. We had an excellent intellectual connection (if you can say that about teenagers) from the day we met. We understood each other very well and his charisma and willingness to always do everything possible to help me suited my bossy bratty personality really well.

The first kiss was anything but erotic. He was so shy and self-conscious that I had to do the whole thing, almost as if I was the man. We were great friends that kissed every now and then but were seen as a couple.

We were in this dynamic for two years, and we spent so much time together that he decided to ask me to be his girl. I kind of already was, but this made it official. He even gave me a 'commitment' ring. I didn’t see any reason not to accept. I was very young and didn’t understand the nuances of the feelings towards boys, and even though I was hardly sexually attracted to him, I was now his girl.

I wasn’t in love but liked his company a lot. I also can’t neglect the fact that he was a rich boy. Always gifting my with anything I wanted or needed and taking me to his family’s mansion and trips to fancy places with his folks. It wasn’t particularly a bad spot to be in.

Bruno was very shy and exceptionally well behaved. He never tried anything besides kissing me. One day I reached for his dick out of curiosity. Some of my girlfriends had already started going further with boys, and that had got me curious. I couldn’t feel much, but I couldn’t compare because it was the only dick I had ever touched. After a few more months I finally saw him naked for the first time. Even being my first dick and after an intense discussion with the girls, I came to the conclusion it was tiny.

Things started to change when one of the other boys in our group started hitting on me. Renato was a black boy a mulato, in Portuguese, which means his skin dark but not so dark. He was two years older as he had repeated the same grade twice and had lots of attitude. Hip Hop Dancer, Skater, and all of that.  Brazil is a racist country, so many of the girls loved to hang out with him and were attracted to him but wouldn’t admit it. He would score lots of make outs and became somewhat of a legend when word came out that he had been having sex since his sixteen and one of the women was one of our teachers.

There was a subgroup of five in the group who lived in the same area. The school was right next to the Confederação Brasileira de Desportos, and we would walk home together almost every day after school. One of those days, a Thursday, the two other girls didn’t come to class because it was a long weekend and they took off early and Bruno, my boyfriend, didn’t attend because he was sick, which meant I was going back home only with Renato.

Controlling my attraction for him was hard. Older, more experience, more swagger, with a thick deep voice, taller and stronger, so much different from Bruno! Almost from a different species. It’s easy to see how obvious it was, in hindsight, but I was naive. It didn’t seem right to be having these thoughts towards someone other than my caring boyfriend.

That day, coming back home together, somehow we started talking about sex, and I asked if it was true that he had already had sex. He said yes, with three women and one of them was a teacher in our school. I was very curious and begged for a name, but instead, he said: “Okay, I’ll tell you, but only if you let me grab your ass and boobs.”

I was shocked and paralyzed, but I felt as if an electric current was running down my spine and my pussy instantly got wet. It was probably the most sexual moment of my life up to then. After a few seconds, I got myself together and answered, “Are you crazy man? How about Bruno? Aren’t you friends?”

“Yeah we are, but I hate how he thinks he’s awesome just because he’s rich. Also, an outgoing, pretty girl like you needs someone that shakes her up a little. He’s too soft. Think I don’t see how he kisses you so shy like he’s a little girl?”

“What do you mean? What’s wrong with the way he kisses me?" I wanted to confront him, but deep down I knew it was true.

“Want me to show you?”

“Of course not, don’t be stupid!” I said while my body language totally asked for it. Needless to say, he grabbed me and kissed me anyway. The way he took me in arms made me even wetter. I hadn't thought it was possible. I was shocked again when I felt a HARD and HUGE thing pressing against my tummy.

“Renato, please don’t tell anyone, don’t tell Bruno, please.”

“Don’t worry, wimpy boy won’t know.”

Hearing those words made me so horny!

I was hypnotized by being intimate with a real man for the first time, and that trance lasted for about five minutes until I finally felt guilty and ran home.

I had no idea but that moment summarized what would be my life for the next eight years. Always cheating and humiliating my wimpy rich boyfriend. Most of the times with huge, strong, fit men. And even better most of them were black.

To be continued...

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