I've got plenty of tales of sexual woe, but I like this one because it was just such a wonderful introduction to human sexuality et al that... ah, I get all aflutter thinking about it. I've probably told this story before so if you've heard it, my apologies.
The second girl I ever made the whole penis-vagina interface with was a mormon. Shortly after telling me this, she put my hand up her skirt - I was waaay too shy to make the 1st move - and ground on my hand like it was a Sybian.
Sounds great right? It was at first. Lots of making out, second and third base.... after a few weeks we went all the way and it was fucking fantastic, legs all akimbo and moist hot flesh everywhere. Still sounds wonderful right?? It fucking WAS, until it was all over with and we're lying there, spooning. I'm all purring and shit and she's really quiet, like short little breaths, so I push myself up to see her face and a little tear is running down her cheek and I'm like what the fuck?? She already told me she's done it before so it's not like I tore her hymen or whatever and she never acted like this when I had half my hand in her and what the fuck??
So I ask her what's wrong as she's trying to play it off on some "oh, nothing, nothing" and I'm just like caressing her, trying to be smooth but thinking "christ why is this girl crying like this??". I went to go get a drink and when I got back, she's rocking back and forth in a ball on my bed and combing through her Book of Mormon. I almost dropped my Fresca. I sat down next to her and asked her if she was feeling guilty? And that just made the floodgates open, y'all - she just started bawling and saying yes, she felt guilty, and she liked me a lot, and she wanted me to like her, but she didn't think i would be interested if we didn't have sex, and she was trying to "Choose the Right" (Mormons! holla!). I was stunned. I told her yeah, we could take it slow, whatever... so she stops crying and cuddles up to me. I'm all trying to be supportive and loving and then she fucking starts stroking my dick! After all that fucking crying and praying and drama, she starts squeezing my fucking swanson and what the hell are you supposed to do THEN? I pushed her away and she said she was sorry, how she's just seriously conflicted.
Still ended up fucking again. This went on for... nine months? I know I was totally stupid for sticking with this but it WAS pretty good sex, in all honesty, and I just thought I loved her. When now I see I was just completely pussy-whipped.
That was a doozy, total. I honestly thought I was going to die when we broke up, like I'd never love again omg - now I look back and god, that's just been TAME compared to some shit I've been through since then, emotion-wise. But still. The first heartbreak is always the worst.