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The first half of this story really happened, the second half is sort of, what I would like to happen, if I was completely reckless and happy to play with fire with the best relationship of my life for the sake of cumming really hard, lol. Sorry if it is a bit meandering and not very jerk-able.
So, I had a girlfriend I probably should’ve known wasn’t actually the most into me a girl could be, very much into me “proving” my worth via planning dates, spending on her, and looking as good as I could in front of her friends. Don’t get me wrong, now it’s all over I look back and can smile on some parts, she was fun in bed when “rewarding” me for being perfect, and I self improved a lot socially and appearance wise for her.
The end came about when I looked through her snapchat. Far from a meticulous cheater, she had saved over 100 messages, pics and vids with the man she was cheating with, including ones calling me a pencil-dick (according to calcsd, 13cm is average length but 9cm is bottom 1% girth, so she wasn’t wrong but it still really hurt) ones praising him for how amazing he was in bed, nudes sent at the spa I went with her to and paid for, and from what I gathered from the vids, her praise for him had good foundation as much as it made me sick seeing how easily she was promiscuous with him, riding him, throating him, licking his butt. When I broke up with her she was equally heartless and unbothered, actually affected me for a long time how little she cared and how easily she moved on from me. And yes, before you ask, I did in fact cum to all this, many many times after, suffering from horrendous post-nut regret but still returning
Now, this guy I actually vaguely knew from some volunteering I do. A confident, muscular man a little older than me (though not some crazy Chad stereotype) with, what I now knew to be a decent sized dick. Confronting him, he was slightly less heartless in his response, but refused to apologize. To him, he feels for me, but he likes fucking lots of different women, and he can’t help it that he attracts taken ones so much. If they didn’t fuck him, they’d cheat with someone else.
I seethed hard at this for a while, but I think really I was just mad at the idea that I could have done all this for miss “high standards”, and this guy did nothing but have a big cock and she had wild sex with him behind my back so casually.
Anyway, enter my new and best girlfriend ever. She doesn’t see me as someone who needs to “perform” or some series of metrics. I have told her a lot that I’ve never told any other girl and she’s always continued to surprise in how understanding she is.
And yet, my cuckold kink has really lit on fire with her. We’ve talked about how hot it would be to spitroast her or something, and after discussing how it turns me on, she makes jokes about my thin dick while we fuck and it gets me going so badly. But still, she doesn’t know the extent of it.
Almost every time I cum with her it’s while thinking of another man ravishing her. I have since moved past resentment and become better friends with the guy who fucked my ex (he really helped me in a bad time next year) and he’s even shown me nudes from some of the cheating sluts he’s currently fucking. I keep imagining him doing it again, slyly working his way into my new gfs innocent pussy. I imagine it wouldn’t be as easy, maybe he’d have to resort to some unethical tactics, get her a lil drunk or blackmail like a cheap NTR plot. In any case it’d end the same, with her creaming on his big dick and realizing how much she was missing out on with mine.
Obviously in reality it wouldn’t be gone about this way, he has joked about loyalty testing her for me, or fucking her in front of me, and while both are hot, it probably is too risky.
I cannot overstate how hard I would cum if it happened though.
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