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This all happened at the tail end of my senior year of HS and everyone was 18.
So in HS there was a girl I knew from class, Annie, who I had a thing for. She was a slender girl, pretty but in a cold way with light brown hair, grey blue eyes. She was a straight A student, she ran on the cross county team but also mostly kept to herself. She seemed cold, boring. Almost asexual. But in conversations with her I saw some sparks that made me think she was hiding a lot.
So I worked up the courage and asked her to prom...which she shot down and told me she was going with Ryan. Ryan was a 6 ft 1, broad shouldered athlete on the football and baseball team.
I was a little taken a back, he was way more popular than her but I guess I wasn't the only one to notice she was pretty.
Still I was without a prom date. Luckily for me a girl from a nerdy club I was in decided to take matters into her own hands - I had no idea she was interested despite admittedly obvious signs in hindsight - and asked me.
The prom itself was fun. Lots of dancing, lots of grinding.
First SPH story
Afterwards my date and I and some friends went to cabins by a lake. We drank a bit, ate s'mores and then retired to individual cabins. There my date - Sarah - and I lost our virginities.
Sarah, I should mention, was 5 ft 2, brown hair, green eyes slender with c cups
She was voracious and we made out fiercely. Clothes came off and soon we were naked on the bed groping and kissing. She took a break to look down and finally saw my cock.
She smiled and looked at it a little quizzically "does it get bigger?' she asked.
It was a raging hard on, any bigger and it felt like it would burst. So I said "no, it is as big as it gets."
She said "I thought they were bigger...ya know like online." She blushed a little as she said it.
I laughed "well some guys are bigger than others, this is just as big as mine gets. It's about 6 inches which is basically the average."
She nodded "oh ok. I guess it'll do." As she went back to kissing me.
The first time we had sex went off fairly normally, with her on top. The second time though I was on top and as I was thrusting in and out she'd shout "deeper, deeper" even as I was balls deep.
I told her that and she goes "oh that's too bad, but keep going."
We had a bunch more sex and then the next morning we left and had brunch and then made our way home.
Second SPH story, featuring Annie
The next day was the big skip day where all seniors did stuff like go to the mall or a theme park.
My friends and I opted for the mall, and while I was waiting for them to get there I ate lunch in a mall restaurant with booths. And who should sit in the booth behind me but Annie and Leah. Leah was Annie's friend and a year above us, she was I guess back from college already.
They talked about prom and all that and I'll try to replicate their conversation below:
L: So how was prom?
A: Eh, fine.
L: oh no, what's wrong? Was Ryan a jerk? Did he hurt you? You can tell me.
A: No, no...eh it's well..let's just say I'm still a virgin.
L.: oh no honey, what? Did he not want to or something? He'd be crazy not to?
A: ah no..he did. And he got hard too..no whiskey dick or anything.
L: so what's the problem?
A: well...you know how he's so big? You know tall..broad... muscley...big hands and feet?
L: Oh yea... [Pausing] oh no...was he too big?
A [snorts with derision] I wish...no. he was too small. I didn't want to lose my virginity to a small dick.
L: [laughs out loud] oh my god. What. I mean it sucks he's small but it couldn't have been that bad. How did you find out? Did he wonder why you two didn't fuck?
A: I mean I guess I had a hint when were dancing. He felt hard but it just seemed too small. Then of course when we got back and made out eventually I took it out and saw it.
L: oh wow. And then what did you do?
A: I asked if he was fully hard, he said yes and I said it was too small for me to suck or fuck but I'd jerk him off.
L; [in clear shock] No. Annie..you didn't!
A: yes I did, It was true after all!
L: oh god..what happened next?
A: well he was upset but he was fine with me jerking him off if he could play with my boobs. So we watched [some movie], he played with my boobs and I jerked him off. It only took like 5 minutes.
L: Wow. I was worried he got like violent...you shouldn't say stuff like that! It hurts guys feelings and it's mean
A: whatever it was true
L: well I'm glad you're alright even if you're still a virgin...
After that the conversation meandered away and so ends the main story but a few notes on after.
1) Sarah and I hooked up a ton over the summer but she refused my offer to date long distance. She also fucked other guys that summer and somehow I was still the biggest by the end.
2) I hooked up with a girl at my 5 year reunion that had dated Ryan and she said I was a little bigger than Ryan but not that much and she has heard that story about Annie's reaction. That girl was not hurting for experience with men either...
3) I heard albeit 2nd hand, of Annie dumping a guy and citing his size (though apparently this one she had sex with first).
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