u/LittleCrazyOneYes

*Names changed.*

*Everyone involved was in their final semester of high school; we were all 18 years old.*

Context: My boyfriend Mat and I had been together for two years. To be honest, everything was fine. He was sweet and attentive, he never gave me a reason to do this, and I was pretty awful, and I know it. I don't want to make excuses. I just want to make it clear that I had this huge curiosity about big dicks. About the size Mat wasn't bad, but he wasn't anything special either. I don't know, porn rotted my brain from a young age LOL.

The sex was good; maybe 7/10 which is more than enough for that age, and it was plentiful, I had my house to myself after school because my mother worked too much and my father never existed LOL.So, you can imagine that we spent a lot of time there every afternoon.

Then came his big mistake. Telling me about his friend Dan. To make a long story short, they were on the same soccer team. After a big win, they were shouting and making more of a fuss than usual. Shouting, fooling around, throwing things, and although they usually showered wearing boxers, that afternoon they stripped completely naked to continue behaving like idiots. And he told me that now Steve had a new nickname because of a mole that was too big on his butt, Alex because he had "too much hair on his balls," and Dan was now "Mr. Three Legs."

He laughed like a little kid, giving me way too many details about everything and nicknames. I obviously only remembered that Dan "had something so big and obscene that it reached halfway down his thigh", and as I understood it, flaccid. Of course I didn't ask and I kept my poker face.

But of course everything changed.

I was SERIOUSLY a little obsessed with this idea of a big dick. My best friend Gaby and I. We used to send each other porn, theorize about it; look at the crotches, of classmates and even teachers. We made a silly promise that if we slept with a guy like that, we'd share him, not necessarily in a threesome, but you get the idea. Of course, our boyfriends didn't know anything about this.

Of course I told her. We began to see the clumsy and unremarkable Dan in a different light. He was a very thin guy, not particularly tall, very pale, and not exactly the most outgoing or popular. Just a guy. With an equally unremarkable and somewhat chubby girlfriend.

We honestly couldn't believe it, although it didn't make sense that Mat would have lied about it. Gaby pressured me to be the one to approach him, since "at least he was a friend of my boyfriend" and I had a pretext to talk to him; she had never even spoken to him. Perhaps I could say that we weren't taking the idea of doing anything seriously; perhaps we just wanted to find out if it was true? The thing is, I started greeting him more enthusiastically, trying to strike up a conversation if I ran into him alone, and I added him on social media. Mat never asked any questions or complained, that it made everything much easier. I like to think that I would have stopped the nonsense if problems had arisen.

A couple of weeks later we could finally have a conversation as if we weren't two awkward strangers, although there was no progress on the topic. Gaby suggested stupid ideas like directly asking him for dick pics, I thought of something more elegant.

I had already run into him a significant number of times in the hallway after algebra; he had a free period, I went there and there he was. I walked nervously towards him, took a deep breath when he greeted me amicably from afar, reached him and said: "Hello, Mr. Three Legs."

OMG, I still remember how he turned red as a tomato. The guys had kept that nickname in "the group of guys", either because they weren't cruel or because of their insecurity, idk, but only in the group. It was a secret and I knew it, Mat told me clearly.

He got really nervous and embarrassed, saying Mat was a bastard for telling. I quickly calmed him down; he was clearly so naive and inexperienced that he didn't realize they were doing him a favor and that obviously it wasn't really an insult.

I bet everything; I knew beforehand that this would be The Important Talk. I told him that surely they were very insecure and that's why they were trying to make him feel bad about it. And that was clearly AN ADVANTAGE with ANY GIRL. Yes, I literally said that and I saw how it changed his mind in real time.

He went from stuttering and not looking at me to laughing nervously. Then he asked if he could ask me things and if it was okay. I nervously said yes, and he began to asking me a thousand times if I really believed that, if "we" (girls) really paid that much attention to that. He thought it was all porn nonsense since his girlfriend didn't seem particularly interested when "he showed it to her," and they hadn't even had sex.

I excitedly replied that ANY GIRL would want to try something like that, that maybe his girl wasn't ready but she surely liked what she saw. I was desperately throwing out bait, like with the "any girl" thing, hoping for a reaction, that he finally asked if even I thought about that, but he just laughed, stared off into the distance thinking, and NOTHING. I felt so frustrated. Men. LOL.

And then my boyfriend arrived. We both remained silent about the subject.

Luckily, my boyfriend asked about an algebra exam, and Dan said, still clearly nervous, that he had gotten an A. My boyfriend cursed while laughing. Somehow I knew it was now or never, that bringing it up later would be messed up or impossible, it was the moment, or maybe I was just really horny and desperate hahaha.

I told Dan that was incredible, that I was so bad at algebra. Mat knew it was true; he nodded, laughing. And I told Dan that he should show me that at my house. And of course I said it in such an ambiguous way.

We literally made plans right in front of my boyfriend to go to my place after class. I know, don't yell at me, I was a total bitch.

We went to my house after class. It was literally a 10-minute walk. My boyfriend came with us, and we chatted about everything. When we got to my door, Mat said goodbye to us, "because he wouldn't study a minute longer than strictly required," I even told him to stay a while at least for a soda. Maybe I wanted him to stop me, maybe I just wanted to dispel any minimal doubt, I don't even know anymore.

But he was firm, saying that algebra bored him to death, that he had things to do, and that if he stayed, he would only distract us.

And he left.

I went home with Dan, feeling incredibly nervous. I offered him something to drink, and we each had a soda. We went to my room, he left his things lying around, we sat down at the desk and... We studied for over an hour hahaha we were being such damn cowards.

We were clearly nervous. It wasn't flowing; he was trying to teach me algebra, I was pretending to understand, he was kind and pretending I wasn't a complete idiot and actually understood something. This went on for over an hour. And to be honest, being there, with everything so real and so close, I don't think I would have done anything else.

I was seriously terrified. I was a virgin before Mat, never cheated, never showed tits or ass to anyone else or looked at another dick, nothing. With Mat, it took me over a year before we started doing dirty things. This was a huge leap.

But luckily he dared.

He started nervously, I felt the blood drain from my feet because you men are painfully obvious, and I could clearly see on his face that he was going to talk about it:

—You know what? HAHAHA —he laughed so damn fake, it was awkward—. When you said, "at my house you'll show me that" HAHAHA it seemed like you meant something else.

—About what? Hahaha just algebra —I didn't want him to do it, I didn't trust myself anymore, fuck, my pussy was dripping.

—Yes, yes, now I understand what that was, but it didn't seem like it HAHAHA —he kept laughing like that—. You know, what we were talking about, umm, I mean... my penis. I even laughed afterwards hahaha what a silly thing to say, right? Sorry, it was just a joke.

He was clearly embarrassed. He didn't even look at me at the end; he was looking at his notebook. I could have left it at that; I had several opportunities to stop.

And I always kept going.

—The truth? —I said nervously, he looked at me the same way—. That would be good, right? That way I could give you my real opinion.

—E-exactly! Otherwise you won't really know.

—Yes. I would have to see it to comment.

—Yes, a photo or...? —I still remember that he had his cell phone in his hand, he wasn't looking at me.

—Nah, better live.

—Su-sure.

We both said it pretending to be normal and cool like idiots.

I remember him standing up awkwardly, we were laughing like idiots, I moved the chair aside so I could see better, he awkwardly unbuckled his belt and then his pants. He pulled down his pants, he was wearing tight black boxers, I'll never forget it, he was completely erect and that thing down there was HUGE. He awkwardly said something like "there it goes" hahaha OMG. And he pulled down his boxers.

His cock sprang out, fully erect. And yes, it was fucking HUGE. Loooong and FAT. With a huge pair of balls down there, and completely hairless, everything looked more sexual and morbid that way. His cock was seriously long and THICK, a little crooked on one side, thicker in the middle, with a huge vein running the whole length that looked like it was going to explode. Everything there was clearly darker than his pale skin. It was a fucking horrendous, appalling, horrible cock, with personality and power. A real cock.

Wonderful.

If I could turn back time, I would improve my first impression. I was so mesmerized and shocked that, ironically, I responded with apparent coldness. I was staring at it so intently without blinking and with my eyes so wide open that he showed it to me and I just stared like an idiot without saying a word for several seconds.

—...and what do you think? —he said without looking at me.

—...Ye-yes, yes.

—Is it okay or...?

—It's scary —HAHAHAHA I swear I said that, I was transparent.

—Well, ummm, yes, I think so —he said, his ego already bruised—. HAHAHA anyway, thanks for the opinion.

He pulled up his boxers.

—No! Wait, wait! I want to see it good so I can tell you —I said desperately.

—O-ok —he said, leaving that halfway.

—You know? I don't know, can I... Umm, touch it?

—Yes, yes, if you want, why not?

I slowly reached out to take it, and he stared at me. It was SO hard, like stone, as if it had bone in it, warm, smooth on the surface but clearly hard inside. Great.

He squirmed a little when I held him; it was so fat I could barely encircle it with my fingers. My panties were wet.

—Didn't she touch it? —I asked, holding it, looking at that without looking at him. Without moving my hand.

—N-no, she just saw it. We were both standing there. She just looked down and told me to put it away. She didn't like it, maybe it scared her like you said, right?

—It's not a bad fear, it's... It's scary, it's just that it's so big. But it's not bad.

I said awkwardly without really saying anything, he just nodded surely without understanding either.

—You know what? If we're going to keep studying, maybe you should cum, so you don't get distracted.

—N-no, no! Don't worry, it's okay, it'll pass quickly, we can continue.

—It's just HAHAHA —now I was laughing fakely like an idiot—. I have a stupid idea, okay? You can say no, it's stupid.

—What? HAHAHA —I shook my head, I wouldn't let it go—. Tell me! HAHAHA come on!

—Okay, I mean, I can make you cum, with my hand in my sink, that's what I do to Mat sometimes, I know how to do it, okay? I have lubricant HAHAHA I told you it was stupid.

And we both laughed in that cringeworthy way. I told him I'd already told him he was stupid, he laughed, I laughed, he asked if I was serious, I said yes while shrugging.

He said it would be fine.

We went to my bathroom, I took the lubricant out of a drawer, he could barely reach to put it in the sink. I put it in one hand, thought for a second and put it in both, cruelly thinking that with Mat I could manage just fine with one hand.

I started desperately jerking him off, with both hands, we awkwardly adjusted ourselves and laughed. He said "he saw something in a porn movie", and told me how to get behind him and jerk him off with both hands.

My chest against his back, my face next to his, masturbating his cock with both hands. And I really did it. I'm even sure I went a little too hard, it felt amazing, I used both hands and I didn't lack dick, I could do it without it being weird, it felt right. I did it with a lot of force, I felt that I wouldn't hurt him "that I was masturbating a real cock", I never asked him if it was too much, nor did he stop me.

It wasn't that fast, maybe a good 5-10 minutes, he was holding back at first, looking at the ceiling with his eyes closed, then he started moaning and when I heard him I wanted to rip his dick off. I started masturbating him using my fingers properly, squeezing, pulling hard but trying not to squeeze too hard. He started saying that it felt incredible, he was writhing, we laughed at times, good laughter, natural, sexual, joyful.

He told me that "it was ready", we both looked at his dick and OMG that thing was seriously twisting.

I squeezed instinctively, stopped moving, but didn't let go, and that thing throbbed, jumped, and moved VIOLENTLY in my hand, seriously, as if it were moving on its own. I could perfectly feel it "pumping" his cum and that stuff coming out in firm spurts into the sink.

I said an absolutely genuine "wow" as he squirted hard in my sink. His cock was still throbbing, he was moaning desperately, we laughed a little at the end. His cock went limp and I snapped out of my daze. Guilt, fear, shame, self-loathing. I let go of him immediately and started washing my hands without looking at him, and he put his penis away.

We didn't say anything more about it; it was really weird. We studied for another hour, and then he left.