Tell me all about your heartbreak. The ones that broke your heart

This might be long and over detailed, it will also probably be nothing compared to some stories others might share, but I'm gonna post it anyway.

In my first year of high school I ended up in a math class with nobody I knew. I also ended up sitting next to a cute girl who also didn't know anyone in the class. We started chatting during our downtime and doing our homework together.

At the time my group of friends and I referred to ourselves as "the Guys" and a group of girls we often hung out with as "the Girls". It just so happened that within weeks of starting high school the Girls had made friends with this cute girl and her friends. Now I was starting to see her when we all went to the movies or hung out. This was good, I started to think that I'd have a shot.

It didn't take long to learn that she had a massive crush on some skater guy. Her crush on him was so well known that even he and his friends knew about it. I figured that if he and I both went for her he'd have a massive advantage, so I decided to hang back and see if they ever became a thing. If not, I'd make my move.

Things got more complicated when the cute girl and her friends decided to try playing matchmaker with me square in their sights. They'd constantly pester me, asking who I liked and who I wanted to date and promising to help hook me up. This cute girl from that first math class, the only one I wanted to date, was the one most persistent in this regard.

A fair amount of time had passed and the skater guy, who knew about the cute girls massive crush, had made no moves to go out with her (as far as I was aware). So I decided that enough was enough and answered the cute girls question honestly the next time it was asked.

Well, that shut her up.

(End of part one. Part two coming soon.)

>>24934002
She avoided me for a while after that and eventually I stopped putting any effort into seeing or contacting her. Her matchmaking friends also ceased their own questions immediately, a pretty clear sign that the cute girl had told them what I said. This will be important for later.

Eventually she contacted me out of the blue, asking if I hated her. I said I didn't and things went back to the way they were before, as though I had never admitted to anything.

In the summer leading up to our senior year her friends invited me to a local fair. One of them lived near the fairgrounds and we were meeting at her place. I arrived to find that the party for the evening was me, the two matchmaking friends, and the cute girl (who had gone ahead to the fairgrounds). Take a moment to think about what was going through my mind at the time, it shouldn't be hard.

Got it? OK, that didn't fucking happen.

We arrived and met up with the cute girl, who was there with her new boyfriend.

Now, I hold nothing against this skater guy. He had no idea who I desired, he wasn't trying to be a dick to me, really his only fault was taking so long to ask out the girl he knew had a crush on him.

No, I had a problem with those girls. They fucking knew how I felt and they invited me and only me to tag along on what was likely my crushes first date with someone else. What the flying fuck were they thinking?

I decided to walk home that night, a long walk home. I decided that the three of them were fucking awful people and became a colder, less trusting person in general that night. After that I made no attempts to interact with them.

But, I was also young and stupid. At the start of our senior year the cute girl came to me, asking what classes I was in. It turned out that we had the same math class and apparently neither of us knew anyone else in the class.

I was struck with nostalgia and, in my youth and stupidity, got my hopes up.

(Looks like there'll be a part three)

>>24934042
Yeah, she was on friendly terms with about half the people in that class. At no point did we sit together, at no point did we work together, my foolish attempts to interact with her generally ended in nothing but small talk and ultimately nothing happened.

I finished the course, on some days never having uttered a word in that room, and went on to graduate.

Now, I heard down the grape vine that the skater guy dumped her shortly after graduation. I then later heard that a later boyfriend had gotten her pregnant and skipped town. As far as I'm aware now she's a single mother.

Whenever I think back to the emotional shit I dealt with and how it all ended, I laugh.

(Though I still have problems trusting people)

I've had several abusive boyfriends and I vowed not to fall in love so easily because it always hurts me. I also thought I was gay. But I met my best friend who is a girl and fell in love with her eventually. She fell in love with me too. However she's got a boyfriend.

Before, I dated out of a need for companionship and never truly loved any of my boyfriends. So I've fallen in love with someone for the first true time and they will never be available to me.

>>24934063
thats for sharing anon

I haven't really updated this since i wrote it last year, so the end might not be completly correct for my current situation, but here we go

>be me some time ago
>kissless 22yo virgin
>family's friends come to eat at our house one summer (they live very far away so we hadn't seen them for years, still our parents are best friends)
>well those twins are looking pretty good, especially that one
>or is it this one?
>anyway she has great boobs for someone her size (95D in France, i'll let you search in your own system)
>meh, she is just parent's friend's daughter so i don't think too much about it
>knows her since she was 2yo so she is still just a little girl to me (i'm 5 years older)
>it's some music holiday where i live, so concerts all around town
>"Hey anon, why don't you take the girls to town so you can show them around?"
>Tomorrow? But i was supposed to raid whatever was relevant at the time... Well i suppose i can go, some guy i was in highschool with was playing, and it's true that during summer the city is nice to walk in during the evening
>one of the twins doesn't come since she has to work the next day (i'll learn later it was just an excuse)
>so the both of us just drive there and spend the night listening to several bands singing, playing, and just walking around town. It was pretty nice
>i finally drive her home and tell her we can do it again the next day, it spreads over several days
>still no afterthought at this point, but the next day was our day off raiding, so why not spend it with a friend, after all she said she'd buy the food this time
>next day i pick her up and we go it some kebab
>don't want to spend the night walking around town again, want to watch a movie?
>"But there is nothing good right now"
>Well praise the internet, i have over 300 movies at home, so we go back to see what i can have that would interest her
>she picks LoTR (extended version of course) because she never seen it

>>24935866
>it's on my computer which is in my room, so we lay on my bed me behind her
>whenever it gets really graphic she kinda roll away from the screen into my arms
>when the giant spider appears, she refuse to look back until i assure her we won't see her again
>i'm still fucking clueless at that point
>i say it's over when she is wrapping Frodo in her web because LOL i made you look again
>she screams when she sees it and just holds on me for dear life (apparently she's really scared of spiders, woops)
>she finally falls asleep during one of the great battle after this scene (to draw Sauron attention away maybe?)
>all i can think about is that i'm lucky that such a beautiful girl is sleeping in my bed, this has never happened before
>too bad she isn't interested... (in the land of the blind ... i'm the fucking virgin moron)
>the movie ends and i cannot turn the computer off, she buried her face in my chest. Well i think it's time for LOTR round 2
>The battle for Minas Tirith finally wakes her up, it's the middle of the night
>she realizes what happened and apoligize, she never managed to fall asleep with someone, that's strange
>ok this is too much, with the very light clothes (it was summer remember? And she wasn't as dumb as me, this dress was revealing a little bit of cleavage, which on her was quite a bit) she has i try to go to second base
>i awkwardly try to at least
>she says that it's too quick
>But that i should kiss her first
>i'mokaywiththat.jpg
>lean in and kiss the first pair of lips ever
>Holyshitthisisheaven!
>I'm in love
>spend the rest of the night kissing her
>finally bring her home at 7am so she's back before parents wake up
>but she has to leave the next day... God WHY?
>i don't care i'll see you next time right? But we don't come back here before next summer...
>then i'll come next holidays (3 months from now)
>we start a LDR aided by skype that will last 2 years while she finishes highschool

2/6 (i think, if i calculated right)

>>24935868
>i go see her whenever i have holidays from work or she comes when it's hers. So we see each others every 2-4 months
>she finally graduates and moves just one hour away now
>WOOHOO SEX EVERY WEEKEND BITCHES
>one year later, everything is going great. I asked without really thinking about it "If i asked you to be my fiancée what would you say?"
>she sits up faster than my cat when it hears is bowl "Wait are you asking me what i think you are asking me????"
>i realize what i said, "Maybe"
>"OMG YESYESYES more inaudible words"
>i don't have a ring or shit so i use my hairband as a ring (so smooth...)
>life is bliss, pretty cool job, nice coworkers, and a loving (now) fiancée
>always saying how much we love each other, this will be forever blablabla
>she starts another year of university, since the housemarket is crazy cheap around here we start to talk about buying a house here for when she's done with her studies since i would be glad to still work where i do for a long time
>during the week she is away studying, so like any sane man with an internet connection would do i look at porn and take part in some thread on some other board on this website
>ends up chatting with some of the frequent posters, espiecially one who liked my work quite a bit
>she isn't really my type (really fat), but she has nice tits, and more importantly it seems i'm one of the few reasons she doesn't kill herself and let her little child alone
>i talk with her more during the week (on another skype account, i'm not crazy) and try to make her feel better. After all she DID have nice tits and some nice aspects to her personnality (with a lot of bad, really bad ones but hey, the personal touch made her tits better you know what i mean i think)

3/6

>>24935877
>on the fiancée side, everything is going better and better, spend the whole summer (well 4 weeks but that's all i get) with her family in the south of Italy, i love her more everyday, the sex is getting better and better (after a veeeeeery slow start)
>I managed to made her squirt (which is my biggest fetish), one of the best moment in my life
>beginning of next school year (i might have gone back and forth in time sorry), things continue to go this way
>one day she comes to pick me up from work (she had an extended weekend and she needed the car to buy some stuff)
>she is very silent, barely saying hello to anyone when we get out of the store
>on the way home i ask her what's wrong, you can guess the answer "... Nothing... . . ."
>i can clearly see something is bothering her so i try a few more times during the evening (one of her friend was having a really rough time with a trial, suicide attempt and everything i thought it might be that)
>i cook and we eat in utter silence, and then straight to bed
>she lies away from me
>ok something is clearly really wrong, i ask one last time
>she starts to cry
>what was bound to happen happened
>i knew this would blow up in my face, in some corner of my mind it was always there
>she didn't say anything yet but i knew what it was. I knew it from the moment she got out of the car at work
>"... did you think i would never find out...?"
>i'm speechless. My brain, my heart, my whole body just stopped at that moment
>she wasn't even yelling or anything. But it was even worth
>i ask her what she read
>she had read the whole thing. Months of tame, but sadly mainly not so tame conversation
>the one that was too much was the fact that "the only reason i'm not sucking on YOUR nipples right now is the distance"
>i just want to die right then and there. I live pretty high on my building and it was still pretty hot weather so we were sleeping with the windows open
>i consider jumping out of it for a moment

4/6

>>24935881
>then i just break down crying too and try to apologize and explain what it was, nothing serious, just harmless (or so i thought) fun during the week. Plus the fact the i actually stopped her from cutting her veins in front of her child one night
>we talked, we cried, we talked some more during most of the night
>we end up in each other arms, i honestly can't remember if we had sex that night
>the next morning i cut all communication with that account, and make everything in my power to get her to forgive me
>things slowly get back to normal after that, even if she wasn't into freaky kinky shit she was still pretty hungry for sex, which i took for a good sign
>but a few months later she becomes a bit more distant and stressed, but with the approach of her "finals" it seems logical. She wasn't from France and was barely over the average all year, so she has to study hard if she wants to pass
>i'm sure she will, like she did last year. She freaked out for a month and passed (not by much), but still much better than a lot of french born student
>but this only get worse with the time. She even spends a weekend away "to focus on her revisions" (this didn't happen once since she arrived in France)
>finally she says that she needs some time to think about "us", she has so fucking much on her mind yadda yadda yadda
>whatever you want, take as much time as you need (i was blind at the beginning but i can see that i'm losing her, and i can't stand the idea)
>In the end, after almost 4 years (well i know exactly after how long but ...) she breaks things up, but it wasn't the yelling, throwing things kind of break up, rather the "we each need to go our own way" one.
>this happened a few weeks before summer, and once she came back from her holiday i went to see her again (she was staying at a friend's house close to me)

5/6

>>24935893
>we talk all evening and i decide to sleep there because it's too late to drive back home (i'm lazy, but moslty i wanted to stay where she was, even if it wasn't the same anymore)
>we end up sleeping in the same bed because we were talking and she can fall asleep mid sentence when she is really tired, and in her defence it might have been around 4am.
>we both missed each other but it was clear that this would never ever be the same again between us. Still we longed for each others contact after the break up.
>so much so that she seems to be having a nice dream, or maybe i'm just imagining things. I might be dead tired but there is no way i'm sleeping tonight. This might be the last time i have her arms wrapped around me and her smoking hot body just right against me.
>to make things even better/worse, summer time again meant we were burning (around 30-35°C at night), so i was just wearing a boxer short, and she was in her tshirt and undies.
>but no it was not the lack of sleep playing tricks with my head, she IS starting to moan. And even grind against my thigh (that i might OR might not have strategically place between hers)
>Oh my FUCKING god i missed that sound so much. But no, things are over, just enjoy it while she sleeps and move on... Or not
>i start moving against her a bit more so she really grinds against me, and i know that she is getting closer to orgasm. After all i've seen it countless times during the last few years
>when she is just moments away i start to kiss her and move even more so she wakes up right before she cums
>still half in her sleep she rides it, really enjoying the feeling of her 1st orgasm in the past month or so
>not really thinking, i move her on top of me and start "dry" humping (which is so far from how we were at that moment but anyway) and kissing her even more, removing her tshirt so i can finally taste her sweat covered godly breasts once more

6/7, looks like i miscalculated

>>24935898
>she is close to a second one, my brain has melted right now and my dick is doing all the thinking
>i remove her panties and my boxer so we can both feel each other even more, holy shit she is so fucking wet...
>that's too much, i have to take her right now. I try to raise her just a little bit so i can get it in the right position but she stops me
>Ohnopleasekillmenow.exe
>"Wait i'm not on the pill or anything anymore..." Oh shit right
>but wait i should have a condom in my wallet (always go out prepared kids!), let me get it it should be in my bag next door
>i get up and rush through the dark house that i don't know, kicking a door in the process and (almost) not noticing it
>i fumble for this motherfucking wallet and finally find the rubber
>i came back triumphant, already unrolling it onto my still rock hard dick (i didn't do anything else than jack off a few times either since we broke up), to find her sitting with her arms around her knees
>OWHELLNO.mp3
>"I don't think this is a good idea anon . . . "
>Are you sure? You know how it could hurt when we stopped this close to orgasm, maybe we just do it this time and see were it leads us, just 2 friends relieving some stress with each other?

But this was hopeless. This was the last time i was close to her like this. This happen about 2 years ago and she was the love of my life, i can stop thinking about her during a really busy day at work, but when i get back home, it all comes back. I feel like i've been surviving just because there is no way i would kill myself, but i can't sleep, everything seems meaningless, yaddayaddayadda you know the drill.
So this is to say, to all the anons around here who MIGHT be in a situation similar to this one, if you DO love her/him, please, for your own sake, don't do this. You will regret it so fucking much.

7/8, this time i'm sure, almost done

File: 1458674931640.jpg (1MB, 6000x4000px) Image search: [Google]

1MB, 6000x4000px

>>24935901

I didn't really believe in Love like you can hear about it, being so strong it physically manifest, but i can assure you, i swear, when i realized how much i hurt her, or when she finally broke up with me, i felt pain. I lucky enough that i've never been in a severe car accident, or shot, or anything like this, but this hurt more than anything i can think about. It's so oppressing. So just enjoy your couple while it last, i know i did, i just wished it never ended.

Pic kinda related, it's not here, but she was looking pretty similar to this body (with areolas a bit smaller, and smoother)