Sorry for the length of my story, but I feel details are important and I love to re-live these experiences! I'll post the condensed version below for the TLDR guys.
One time, a few years back, I dated this smoking hot chick, "Heather" for a couple months.
Man, did she have a body! She was tall, tan, long, perfect, athletic legs leading up to this perfect, round, firm, big bubble butt like two big muffins fresh out of the oven that you just wanna squeeze. And she's the only girl I've fucked (thus far) with fake tits, they were perfect (I wish she'd went a little bigger. Still keep some photos of her, which I included minus the face.
We knew each other in high school, she had a crush on me then, but I was too shy to do anything about it, and also knew she was a bit of a freak, which intimidated me as a small dick virgin. Well, thank God for second chances!
We went our separate ways after the summer we graduated, and I hadn't spoken to her since, until one day, after about 7 years, completely outta the blue, she messaged me on FB and we started talking and texting.
One day, in a text, she revealed that she used to wonder how big my dick is, that she even used to masturbate thinking about me, and asked if I used to jack off thinking about her. Then, she asked me point blank "So, how big is your dick?" I told her my dick was much smaller then, but had developed into my 20's, sent her a couple photos, and she loved it, told me the next day that she had played with her pussy while lying in bed that night.
Off topic, but her mom, a younger good looking single lady, borrowed her phone and ran across my photo. That made it really awkward meeting her mom! She told me her mom got angry about it, but I wondered if it secretly turned her on.
So, that weekend, I made the four hour round trip drive to pick her up and take her to stay the weekend at my apartment. We had both gotten each other so hot over the phone for the past couple weeks, that she was riding my big dick within thirty minutes after we got in my apartment, her moaning, telling me how deep I was, me gripping her fat, firm ass, and watching her perfect, perky, enhanced titties bouncing up and down.
So, I personally knew two of the guys she had dated over the years.
One guy, "Nick", had been a close friend all through elementary til we had a bit of a falling out when I started smoking pot in 8th grade. He was a bit of a poindexter back then, small and skinny, big glasses, a bowl cut hair style.
One day, we got to talking size, and he admitted to me he thought he might have a small penis, and asked how big mine was. We weren't gonna show each other, but we agreed to separately take a ruler into the bathroom and measure ourselves hard.
He came out with a sheepish look on his face and said he was like 3 inches. I took the ruler into the bathroom, got my dick hard, and measured for the first time. It was around 3.5 inches.
I was really impressed with his honesty, because I couldn't do the same. "It's about 5 inches" I lied. He looked at me with this look of envy and admiration, called me "big guy".
UNRELATED DETOUR FROM THE STORY! SKIP DOWN TO GET BACK TO THE MAIN STORY.
I remember one night, after graduating, all of us 18, at a friend's house who had a swimming pool. It was me, Nick, a guy Adam and his cousin Brandon, Heather, this other tall hot chick, and two twins, who were cute but nothing special, really. We were drinking a little beer, the parents were gone for the night.
Brandon was trying to get some skinny dipping going on. Me and Nick both obviously got red in the face, tried to avoid the topic, so me and him and the girls all got in our underwear (I quickly got in the water before my hardon became visible.) Adam and Brandon decided to drop everything and go naked, which elicited some stares and giggles from the girls.
They were both soft, but not fully soft. Brandon, a really well built, muscular, curly haired guy, had a decent cock from what I could see. Adam had a bigger dick, probably around the size of my soft cock right now, and two big low hanging balls. He was more of an exhibitionist, and a jokester, he had this signature goofy giggle he always did, chuckled "Look it's a helicopter!" With his hands held up, rotating his hips, trying to twirl his cock around, eliciting more giggles.
I overheard one twin whisper to the hot girl "Adam's got a nice dick." Then turned toward me and Nick "Why aren't y'all getting naked? You afraid for us to see your little weenies?"
"Shit (My Name)'s got a Superdick!" I laughed, hoped the subject changed, me and Nick stood around awkwardly, Brandon and Adam showed off their dicks, Adam even got one of the twins to touch his. We swam for a bit.
I had a system of pulling my shorts from my thighs to prevent them from clinging to my body, revealing my little package (made smaller in cold water) as I got out of the water, but I noticed as I got out of the water, Heather's eyes transfixed on my package, not sure how much she could see.
BACK TO THE MAIN STORY
So, a few years after graduation, I guess Nick came into his own, he and Heather hooked up a few times (before she got her new tits).
The other guy from high school that Heather had dated, was a guy named Gerard. He was an okay guy, we used to sneak behind the cafeteria and smoke bud, but I always felt he was kinda douchey, thought he was too cool, cocky, musician, long hair.
He dated this hot chick, Jessica, for a while. She was short, super thick, with big thighs, a huge ass, like two basketballs stuffed in her pants, dark skin, brown eyes, looked Latino, long brown curly hair.
One day I heard some of the girls talking, "I heard Gerard has a big dick." "Well, Jessica said she tried to give him head and she couldn't get her mouth around it, sooo..."
So, I was always curious about Gerard's endowment.
So, back to me and Heather at my apartment. The second night, we had just gotten out of the shower together, we were both completely naked on the couch, watching TV.
I was getting the Royal Treatment. I was smoking a cigarette, laying on my back across the couch, Heather was sitting up, I had one leg laid over her thighs, the other leg stretched out behind her ass. She was staring at, playing with, stroking my big, hard dick.
"You like my big dick?"
"Uh, yeah! It's perfect."
I didn't wanna come off too weird, but I'm always so damn curious about this kinda thing, so I just decided fuck it, I'll ask.
"What's the biggest dick you've been with?"
"Oh, I don't know, you don't wanna talk about that...."
"Ah, come on! I don't care, I'm comfortable with what I got, it's just a turn on to know. Was Gerard big?"
I could tell by the look in her eye, they widened just a little. "Yeah!"
"How big compared to mine? Be honest, it ain't gonna bother me, I'm just curious..."
"I don't know, probably like..." She held my dick up at the base of the shaft with one hand, and with the other she held her two fingers up, probably about an inch, maybe an inch and a half above the tip of my head. It was so hot, it took me back to the days of having a baby dick, comparing to this really hung guy in front of this hot chick, feeling embarrassed and envious, but also really turned on, wishing my cock would grow to be able to reach her fingers, knowing he had been deeper inside her than I could ever get.
"It was really thick, too."
"Did it turn you on when you first saw it?"
"Yeah, it was hot. I had heard he had a big dick before that so I wasn't surprised."
"Did it feel better than mine?"
"No, I think you're the perfect size, and you know how to use it a lot better." Don't know if that was true, or she was just being nice.
"What about Nick?"
"Haha no! What's funny is, he told me it was big, but he showed it to me, it was like..." She put her two fingers on the shaft of my dick, about 4.5 inches up from the base, around the area where the color of my dick changes from a darker shade to a lighter shade. "I was like, Aw poor guy! Haha!"
This was also really hot, especially because I used to feel so insecure about being small, knowing I had fucked her in places where he couldn't, that I made her feel full, made her cum, made me feel like a Big Dick Man, powerful, masculine.
I put my cigarette in the ash tray. Opened a Trojan, unrolled it down my big 7 inch dick, pushed her back down on the couch, lifted her thighs up in the air, she was wet and ready as I entered her, gasped as I slid the full, curved link all the way in, started fucking her, making her call me Superman while I jack hammered her until she came!
