The UnChonological Adventures of Classyguy Book 1:High School- Chapter 1: My Experience with a 34 Year Old Brazilian(m/F)(Part 1) | 2016

So let me give some background information. It was my senior year of high school (I had just recently turned 18) and one weekend my parents had a guest over for dinner, who I'll refer to as Carmen to protect her identity. My mom teaches ESL classes, and Carmen was a student of hers- the two had stayed in touch and remained friends, until soon after this ordeal, but I'm getting ahead of myself.

Carmen was a slender, attractive woman with a deep accent, but I didn't yet pay any attention to the attractive part- we just got along really well. We were instantly consumed in conversation because I felt so cultured, having just finished a summer exchange program in Europe, that I came across as such. One example of this was when we were all eating at the table my little brother was complaining that he didn't like something and I put on my airs explaining how I was able to wolf down food that looked completely unappealing out of respect for my host family. Carmen was impressed and agreed with me. Also during conversation I mentioned the different colleges I was applying to, and it turned out a couple of them were in the city in which she lived, so she offered me a place to stay to save on a hotel room when I visited them. I agreed, and my parents didn't even notice.

Fast-forwarding to when I came back from my evening run, I saw my parents and Carmen sitting on the couch watching a movie. Mom and dad were snuggled under their own blanket and Carmen was sitting alone under hers. After showering, I came downstairs and sat next to Carmen with my parents on the other side of her. She offered me to get under her blanket either right away or a little further into the movie- I don't really remember- but we were still sitting apart. At some other point I asked her a question; something long the lines of how she was doing or how things were going- again I can't really remember details too well anymore as this was a few years ago. She immediately answered "34," thinking I had asked her age. I found that a little funny, but didn't read too much into it. By now all that I knew was she was a very cool lady whom I could get along with like we were two adults, she seemed to view me as an equal, and even under the blanket with her any sexual thoughts were faint "what-ifs."

After the movie my parents pulled out her blow-up mattress and went up to bed, because they're old farts. But Carmen and I of course wanted to stay up later and continue chatting and enjoying the Nintendo Wii Sports that we had started playing with while dinner was cooking. In case you don't know what the Wii is, it's a video game system where you stand up and pretend you're actually doing something while a little guy in the screen mimics your actions. It's not intense lifestyle that consumes your days while you level up killing zombies and "noobs," but rather meant for social fun, and most importantly to this story, it involves physical activity. When our volleyball game started to get going, she took off her sweatshirt, revealing a tight black tank top and looking at that helped me notice the black yoga pants she had been wearing the whole time- the full-black attire accentuated her slender body and very nice ass. Her face and hair were okay, which was why I only just now noticed how actually hot she was. After a few more rounds, I forget who initiated this, but a thing started where we would reach out and tickle the other when one of us got beat. Now things were getting real. I was up late literally playing with a physically attractive 34 year old woman with whom I was getting along really well. I obviously had no certainty that this would lead anywhere further, but what I did know was that I didn't want this night to end. I went into the bathroom to compose myself, and made a resolution that if a window of opportunity arose, I would take it, because this opportunity seemed so once-in-a-lifetime. Coming out, my only strategy was to suggest we keep going after each game, and from what I remember she beat me to that most of the time. Keeping the night going was becoming a mutual effort on both of our parts.

Somehow we moved to the couch, and the tickling picked up in frequency. We were playing soccer, and after we finished the first game, and we opted to play another without either of us having to suggest is, I formulated a plan. I didn't want to get into trouble by crossing a line, even though by now the odds were in my favor that she was being more than just friendly with me. Therefore, I thought of a way I could create a window of opportunity for her to give a more obvious sign that something here could happen, while leaving me room to retreat without much suspicion in case she didn't respond. I purposefully lost the second game, and then used that as an excuse to tickle her (whoever lost each round of whatever game had earned tickling rights by now), but this time it wasn't a quick jab. I reached my arms around her back and tickled her sides enough to make her jump and thrash around giggling out of control...onto my lap. Now we were going into full body contact. I kept my hold, and in the frenzy we both ended up laying on the couch with me on top. Now I honestly think this was one of those kisses where it really did just happen. I remember looking down at her, and then we were kissing. Passionately. I was making out with this 34 year old hot Brazilian. It was pretty surreal.

Being the young horny man that I was, my hands began to roam. Even though our bodies were pressed together, I was able caress enough of her body to make her kiss me harder. I forget if neck-kissing was a thing of mine yet, but I definitely got to squeeze that fine ass of hers. As my hands went under her shirt in the front to go after her tits, hers went behind my back and clawed it under my own shirt. Her tits were definitely on the small side, like small enough where she didn't need a bra- personally I don't mind that- and again she kissed me harder as I messaged them. It was kind of cool again feeling like an equal, doing what I thought was more of a high schooler thing with this older woman. I think I did bite her neck, or at least nibbled on her tits when I pulled her shirt down and went down on them, because I remember her saying in her sexy latina accent: "You like biting? mmmmmm I LOVE biting!"

Eventually I was rubbing her vulva through her yoga pants and paying attention to the clit. Now I had definitely had some experience before, between online chatting, sex stories, a month-long relationship with tons of sex, and a casual encounter,so that coupled with her possible under-estimate of what any 17 year old American boy is capable of, led to her being shocked with what I knew how to do. She cooed at the mere fact that I knew to message the clit, but once the gold-star treatment wore off, she started holding me to a higher standard, and since I was still inexperienced, especially next to her 34 years on this planet, she helped me make her feel even better. She held my hand, guided it in slower, more powerful circular motions around the whole area. That was hot for me to be taught like that, and for her, well, she leaned back in ecstasy. I then surprised her even more by sliding my hand inside her pants and under her panties, putting two fingers into her by now very wet cunt. This time I lucked out and started doing it properly right away by pushing up, so she simply exclaimed "HOW DO YOU KNOW HOW TO DO THAT!" before arching back again in pleasure- no more teaching needed.

Her limit was reached when I tried to pull her pants off to eat her out. She said we can't. In her defense, my parents WERE sleeping just upstairs with an open door, and they usually come downstairs in the middle of the night. The music from the paused video game was still playing pretty loud and the lights were still on; if anyone came down we'd have been screwed- I was just too horny to care- thank god for the sexual temperance of women! Especially because lone behold only minutes later my dad did come down, and it was only because we stopped that we were able to have ourselves looking presentable in a few seconds, pretending to play the game. He just told us to turn the TV down and pointed out how late it was. After he went back up we commenced making out and fondling though. It felt so amazing to have such a mature woman in my arms- it was really a coming-of-age experience.

Eventually we slowed down and snuggled up, talking. That's when I asked if she had a boyfriend... and she didn't. We exchanged numbers, and while I was attempting to input mine into her phone, she made the process really hard by suddenly messaging my cock through my pants.

Of course all good things eventually come to an end. With yet another passionate make-out sesh, I bid Carmen goodnight. She did come down to my room (yeah I lived in the basement, but it's a nice basement) to visit me and kiss me when I texted her again (yeah, go ahead and cringe...it was a few years ago, remember), but after that I jerked off and spewed a shit ton of watery cum thanks to blue balls which had never never before been so worth it, then drifted off into one of the best sleeps in my life. For those of you who might wonder why she didn't give my cock attention, it was because A: I later found out she really only liked fucking, and not much foreplay, but since I initiated the stuff on her and there was no other option that night she didn't mind receiving it, and B: it's much easier to slip a hand out from fingering a girl and quickly act normal than to stuff a hard penis back into jeans in case anyone came down.

So the next morning for whatever reason my mom took a picture of me and my dad (I think for an early Christmas card or something)*, and then I left to my friend's place for the rest of the weekend as planned, but we started texting and plotting our next rendezvous within the hour...

To Be Continued in Part 2...

*Fun Fact: The picture of my dad and I still stands on the mantel in a frame. Every now and then when I'm back home I stop to look at that grin on my face from a few years back. "Damn that was a great night," I say to myself.