My final year of high school had just begun, and the whole class was getting ready for the entrance exams, with classes in the morning and prep school at night. The afternoon was the only time I had for leisure activities. As the weekend approached, we'd leave the prep school and go drinking at a friend's house or even on the street, the traditional vodka and Schweppes.

Before high school, I didn't really go out; I was a typical nerd with low self-esteem. I was never ugly; my friends said my only problem was being sloppy. I didn't dress up, get out of bed, or even comb my hair, I was always wearing the same clothes, and so on. But that year, the atmosphere was different. I can say that high school was the best year of my life. I stopped spending weekends at home playing video games and started going out with friends and socializing.

This allowed my friends and I to connect with a group of freshman girls, all two or three years younger than us, but very pretty. One of my friends, the girls' cute friend, organized our get-togethers, usually a barbecue at someone's house. At one of these get-togethers, few people had confirmed their attendance; there would be six of us, three girls and three boys. So, we decided to watch a movie, have a more romantic evening, and increase our chances with one of them.

Up until that point, no one had hooked up with anyone, just friendships between boys in high school and girls in high school. Of course, there was a lot of teasing and innuendo, but everything was discreet. We then agreed to watch a horror movie, and my two friends and I discussed who was into whom, so that when it came time to sit down on the couch, we'd be next to the right person.

The day of the movie arrived, and I went early to my friend Vitor's house. Soon after, the girls' cute friend arrived. It wasn't long before the girls arrived, taken by one of their mothers. There was a problem: one of the three girls couldn't go—it was the girl I was going to try to kiss that night. It was just Gabriela and Amanda. Vitor was going to try to get with Gabriela, and his cute friend and Amanda were there just as friends.

I was frustrated, but the night had to go on. We sat on the couch, in order from left to right: me, a blank space where the girl I was going to meet would be sitting, Amanda, her cute friend, Gabriela, and Vitor. The movie had just started, and I could already hear Vitor talking to Gabriela; he was already making moves and didn't want to waste any time. I was curious to see what would happen, and every chance I got, I'd glance over, but nothing. Gabriela didn't seem interested in Vitor. At one point, Vitor tried to kiss Gabriela, but she turned her face away, rejecting his advance. I almost laughed, but I didn't want to embarrass my friend.

" I'm going to the bathroom, I'll be right back, " Gabriela said. We paused the movie so she could go. When she came back, instead of sitting in her usual spot next to Vitor, she sat in the empty space between me and her cute friend. It filled my head with doubts: could she be into me?

Gabriela was a beautiful girl, blonde with brunette highlights, with a sculpted body. She wasn't very tall, maybe about 5'7", a little shorter than me. Her eyes were blue, seemingly mixed with brown. Of the girls, she was the prettiest. Of our group, Vitor was the most handsome, so from the beginning of our dates, we kind of pushed each other, but apparently that wasn't what Gabriela wanted.

I looked at Vitor, who was alone on the other side of the couch. He looked at me like he was saying, " Try it, " but the only thing that stuck in my head was, " Is that really true? " It wasn't that I didn't want it, quite the opposite, but my low self-esteem wouldn't let me believe she could want me. The horror movie started playing again; it was still halfway through.

The first scare the film gave us, Gabriela came closer to me, I felt her arm brush against mine. We were under the covers, it was a cold day, just that light touch there made my heart race, I started to get excited, but I was able to hide it well thanks to the blanket.

Another tense scene. This time, Gabriela put her hand on my arm. I glanced at her quickly. She looked at me. I became nervous and turned my face away again. I didn't know what I was doing. I started to get angry at myself. I was a coward, I was chickening out. Gabriela was two years younger than me, but I felt like a child there. I looked back at her. Gabriela was still looking at me. I noticed her breathing was uneven. She was nervous too. For some reason, that calmed me down. I leaned in and kissed her. A passionate kiss. She kissed me back, and I just stood there. Our cute friend started celebrating, "finally," he said. Vitor and Amanda joined him in the celebration.

We stopped kissing to laugh, they stopped celebrating, and went back to the movie. This time Gabriela and I settled in better, making it easier to kiss. We didn't watch any more of the movie, just sat there making out. When the movie ended, I felt like I was all sticky. Everyone left, I waited a bit under the covers for my excitement to pass, and then I left too. I got home and had the quickest handjob of my life; I was already ready and came really quickly.

Movie night was on a Friday. We went out again on Saturday, Sunday, and a few more days the following week. On Thursday, we skipped prep school and invited the girls over for pizza and drinks at Vitor's house. This time there were a few more people; Gabriela came too. As soon as she arrived, I poured her a drink, and we went for a drink away from the rest of the crowd. We quickly started kissing.

– Are you a virgin? – she asked me, embarrassed.

– I'm not – I replied, I could tell she was insecure – is that a problem?

– No, none.

- You are?

– Yes – Gabriela answered very quietly and embarrassed.

I seized the moment, became incredibly aroused, and kissed her again. Never before had I touched her other than her back, head, or face. But this time, I slowly ran my hand down her back until I reached her ass. The mere mention of her virginity told me she was thinking about having sex with me; it drove me crazy. I touched her ass, but she didn't do anything. I gave it a little squeeze, and she stopped kissing me to smile and say, "Watch your silly hand." I took the hint; that was the limit.

I don't know what happened at dinner. Gabriela and I stayed away from everyone else all night, kissing in a corner. When we realized everyone was leaving, Gabriela said to me, "Do you want to come over to my place with me? " My heart sank. " Of course, " I replied. She noticed my excitement and said, " Don't get too excited ."

We walked to her house, about five blocks away, not far. On the way, Gabriela was put in my arms, and we chatted. We arrived at her house and went inside. Her parents had gone away, and her brother had gone to sleep at a friend's house. She took me to her room, and I could tell she was embarrassed. The room was all pink and white, with a single bed on the wall opposite the door and a desk full of her school books. I couldn't really notice the room. Gabriela started kissing me. We were still standing, but this time she was flustered. We bumped teeth; she was quite nervous.

– Stay calm, we don’t have to do anything if you don’t want to – I said trying to calm her down.

– I'm nervous because I want to do it – she said, I was also extremely nervous, but I tried not to show it.

We took off our coats, sat on her bed, and started kissing. She took off my shirt and looked at my body. This time I felt embarrassed; I'd always been a little overweight; I'd lost weight but hadn't yet reached my target weight. But that didn't seem to matter to Gabriela. I took off her shirt, revealing a beautiful black bra, a flat stomach, and very pale skin. I could see her chest rising and falling with her heavy breathing.

I put my hand on her back and unhooked her bra. She held it tight to keep it from falling and didn't take it off completely, even more embarrassed than before. I watched her as she debated whether to take it off or not. She did, revealing her firm breasts with their pink, hard nipples. I hugged her and kissed her. I placed my hand on her chest and squeezed lightly. She bit my lip. I broke the kiss and moved my mouth down to her nipple, kissing it. She moaned and said, " Wow, they're so sensitive ." I continued to keep my mouth on her chest, kissing it everywhere I could reach.

I lowered my hands to her waist and unzipped her jeans. I stopped kissing her chest and pulled them down, but I didn't take them off completely; she was getting even more nervous. " Go ahead ," she said after a few seconds of my pause. I pulled her pants off completely and dropped them on the floor. Her panties matched her bra. I kissed her mouth again, slowly putting my hand inside her panties. She quickly grabbed both my wrists, and I stopped the movement and kissed her.

“Do you trust me?” I asked, looking deep into his eyes.

“I trust you,” she said and released my wrists.

I started pulling down her panties. She lay down, and as soon as her pussy was visible, she put her hands in front of her. I pulled them off completely, dropping the panties on top of the pants on the floor. Gabriela closed her legs tightly, lying down with her hands still protecting herself. I sat still beside her, not going to do anything without some sign from her. I saw her breathing more heavily than ever. I noticed she released the tension in her legs. I placed my hand on her knees and began to gently move down the outside of her thighs, until I reached the middle. From there, I started back up, but this time, running my fingernail very lightly. I saw her skin tingle.

Gabriela took her hand off her pussy and began to spread her legs. She saw me staring at her pussy with my mouth open, and quickly closed her legs.

– Don't look at her like that – Gabriela said, completely embarrassed.

– Do I look like a pervert?

– No, you look like you don't like it – she said, her insecurity speaking louder.

"No way, Gabi. I'm loving it, you're so beautiful," I replied sincerely, making a gesture with my hand as if I were wiping saliva from my mouth and saying, "I'm drooling over you."

Gabi smiled and opened her legs again. This time I got a good look at her pussy. It was completely smooth and pink, so tiny. I was blown away; it was so beautiful. I got on top of her, my hips between her legs, and kissed her mouth again. I stopped and moved down to her neck, biting and lightly kissing her entire body, moving lower and lower, passing over her breasts, belly, and belly button. I could see her skin crawling under my touch. I realized my cock was throbbing inside my pants.

Before I could reach her pussy to suck it, she stood up and I got off. We sat side by side, her eyes on the bulge in my pants. "Open it," I said, trying to sound sensual. She bit her lip and looked at me. She put both hands on my pants, ran her hand over my cock, over my pants, and gave it a squeeze. " It's really hard, " she said. I laughed. It felt like a rock; I was so turned on. Gabriela then opened the button and zipper. She put her hand inside, between my pants and underwear, and firmly grabbed my cock.

“It’s so warm,” she said, her hand was very cold, but it felt really good.

“Is this your first time touching one?” I asked, knowing she had had a boyfriend for a few months the previous year.

– Under my pants, yes – she replied, I didn’t want to know any more details.

– You can put your hand under your underwear if you want – I said trying to encourage her.

So she did, taking her hand away and putting it back, this time under my underwear. She squeezed it again and started masturbating me lightly. I took advantage and kissed her neck, enjoying the delicious perfume she was wearing. She stopped touching herself for me and started running her hand over my cock. I felt her fingers graze the head of it.

– Be careful, the tip will be very sticky – I said, she looked at me without understanding and I explained about the pre-ejaculatory liquid.

– I'm also very wet – Gabriela said with a little laugh, she was letting go.

I lifted my ass off the bed and pulled down my pants, she didn't take her hand off me. When she saw my dick, she squeezed it even harder, it wasn't hurting.

– How many veins… – she said while looking at my dick, it was being very exciting.

I kissed her mouth and made her lie down again. I knelt down, grabbed the condom, and started putting it on. Gabriela just watched. Properly protected, I settled myself between her legs. When I touched the head of my cock to her pussy, her eyes widened and her mouth opened, letting out a soft moan. "That feels so good," she said. I continued to rub my cock around her pussy. She was already very wet, but I wanted to ensure as little pain as possible.

"If it hurts, let me know and I'll stop," I said as I adjusted myself to begin penetrating her. She nodded, and I began to enter. It felt like I was hitting a wall; it wasn't going in.

– It hurts, but it won't stop – Gabi said.

– Are you sure? – I asked worriedly.

– Yes, I think it’s coming in.

It was true, I felt a slight entry. Gabi squeezed her eyes shut in pain. I pulled out what little was inside and slowly came back in. She opened her mouth and said, "It's pain mixed with pleasure, you can continue." I repeated the same process. When I realized the entire head had entered, I pulled out a little and realized there was blood.

"Okay, now you're not a virgin anymore, I can go home," I said. It wasn't a good time for jokes, but that's just the way I am. Gabi looked at me, startled, and I added, "Just kidding."

– You fool – she said, I could see she was a little embarrassed, but she recovered and said – I want you all inside me, find a way.

She smiled, and I smiled back. I went back to work, going in a little and then out. On the way back, I went in a little more than the last time. It went on like that until it was all in. Gabriela was holding my arms very tightly. She felt a lot of pain, but she held on.

“Is this when you eat me?” she said sensually, placing her hands on my back.

I pulled out almost all of it and entered slowly. It hurt a little for Gabi, but she asked me to do it again. I did it a few more times, around the fourth or fifth time, and she said she wasn't feeling any more pain. I increased the speed of penetration a little and went back to kissing her. Gabi was moaning, but it was muffled by my mouth on hers. I felt her digging her nails into my back; it was a pleasurable pain. I stopped kissing her and started focusing on penetration. It felt so good and tight at the same time; I couldn't take much more at that pace.

– My God, it's so good – Gabi said excitedly, that was enough to drive me crazy.

I felt her legs tighten around my waist, making it difficult to move, but I managed to keep going. She was moaning loudly. I was thankful no one was home. She dug her nails in even harder; I imagined blood was coming from my back. I was actually trying to distract myself; otherwise, I would have come. Gabi then tightened her legs around me, opened her mouth moaning, and squeezed her eyes shut. She ran her nails down my back, scratching my back. I came. I couldn't take it anymore, and I came hard. I almost lost the strength in my arms that were supporting me. I tried to continue, but I realized my partner was exhausted on the bed. I stopped, pulled out, and lay down, hugging her.

“What was that?” she asked breathlessly.

“I think you came,” I replied.

– That was so good

– I liked it too

I got up and took off the condom. Gabi wanted to see what the cum was like, so I showed her. I tied a knot, wrapped it in toilet paper, and threw it in the trash. I went back to the bedroom and she was sitting there wearing only her panties and bra.

“Lie here with me,” she said, patting the bed twice.

I put on my underwear and lay down. We stayed up all night talking, cuddling. When it was almost morning, I left, we kissed some more, and agreed to keep seeing each other. It worked for a while, a few months, we had sex whenever we could, but it didn't turn into a more serious relationship because the person who would become my wife appeared in the picture.

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