How it all started [Cuckolding/Cheating]

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I figured I’d post my experience to how I became a cuckold & I might give some helpful insight to some people or others can share there experiences or thoughts on how they got into this lifestyle.

I’ve never had an issue with girls, in high school I had gf’s and was very active, almost to a fault, hypersexual some would say, it caused alot of issues in those young relationships where some gf’s were almost intimidated by my sex drive, so i’d cheat and be an awful person in those younger years.

at one point early college years, I’d been in a long relationship that had ended abruptly, I made a point to avoid relationships, going from a small town to a large college campus, I thought this is my chance to get with as many girls as possible, I had successes and for the first time failures, losing out on someone I was “chasing” to someone else or just being turned down. The obvious college guy, loud & drunk wasn’t playing as well as I had gotten older and into a bit more mature levels of dating, I had a hard time adjusting to that, so that was the first turn in taking down my ego a notch.

I was hanging with a girl from work, I was about 21, she was quiet, a runner, long legs, had the nerdy librarian look going for her. great boobs, runners ass, perky but not that large. honestly wasn’t my type personality wise but at that time, whatever. We went out one night, she came back with me and we hooked up. Both drunk, both didn’t remember much, she woke up before me and admittedly i am a grower not a shower.. fast forward a few weeks. Young and immature as I was, I kind of ignored her, didn’t particularly enjoy the time hanging out with her before the hook up etc… not a great guy at the time. She texted me a long rant how I’m cocky and think I’m hot shit and the part that drove into me said (and you have a small dick)! lol I remember stopping in my tracks and that was the first time in my life I’d even considered penis size and a girls reaction to it. We ended up hooking up later a few times so my brain should have said she was just being mean but it has always stuck with me, not angry just something that made me realize what’s in a girls brain when thinking about sex.. maybe?

I’m about 7.5-8” & girthy. probably 5-6″ diameter, but I’m a big guy, exercise but just big and stocky so when flaccid, it looks small admittedly, she saw me sprawled out naked in a cold room, I’m sure it wasn’t great, but the first gf i ever had who was petite, who we lost our virginity to each other had trouble taking me for the first couple months of our trip into the sex world. So subconsciously, I think my ego maintained that “Im so big, girls can barely take me” which obviously isn’t the case. so this random one night stand defeated me for months, years? I can’t remember how long, completely tanked my ego for some reason, more than it should, now when I watched porn I hyper analyzed penis size and girls reactions, I know it was acting, and the “you’re so huge” was just part of the show (even if the guy was huge).

This carried into my dating & personal life more than it ever should have, now that I reflect, I almost completely stopped chasing the one night stand, and started on the nice guy routine, trying to connect with girls, which is probably a good thing but my confidence was not there.

A few years later, after a few quick relationships, always ending in jealousy or accusations of cheating, by me, a lot of it probably insecure projections from my younger days of cheating on any girl i got close with, I moved out of this college town for a real job in another area. I started talking to a girl a few years younger, she wanted to “settle down” (really just wanted a bf to take care of her in retrospect) but being still dumb and naive at 22-23 I thought well this is it, she was way above my league, model looking gorgeous, trying not to be a gooner and come across as some porn addict but we’d watch porn together and she was almost an identical image of Janice Griffith, she’d agree (who wouldn’t) , she was oddly into porn, more than me, so I initially started fetishizing her selections internally. She just had a ridiculous round butt that stuck out and she flaunted it, tiny frame, big perky C cups that would spill out the sides of her bra and covered up her entire chest because of her petite frame, dark skin and an ass you’d not just not expect on a 5’3. 105 lb frame.

she moves in, first year we’re just in bed fucking or at work, both probably, on the border of sex addiction, eventually we grow apart as the honeymoon phase goes by but still both very hypersexual, I start getting paranoid as the connection seems to fade, obviously it’s not sustainable to just expect sex at any time forever, so when that slows down, still young, dumb full of cum brain thinks immediately, she’s cheating. she posts pictures on IG and gets dozens of comments half from dudes telling her to hit them up or name dropping a place I’ve never heard of “come to the lake again this weekend” me thinking what lake?

so of course go through her phone one night and she has guys saved as her friends names, one guy saved as “mom”, nothing specific about cheating but just implied conversation. I can tell there’s chats missing, I question her, we fight, we break up, we get back together, the cycle continues a few times over a few years. My brain, still hyper sexual is just essentially at this point saying this girl is so attractive to you, I don’t even care what she does, during the break up period, the obvious “who’d you get with” accusations fly, nobody is always the answer. so the relationship gets toxic but we stay together. we discuss open relationships, swinging apps, threesomes etc.. she always pushed the idea of two girls and me, she’d name friends and id of course say hell yeah! lets do it! It never came to fruition, almost like it was a tease, we’d get on dating apps and chat up couples, eventually, knowing she still took attention from guys whenever it was offered, id say, like that single guy or this guy etc.. so she did, sometimes I’d check her phone and shed have chats going with these guys and not mention it, scroll through, shed have some pictures in underwear or bikini’s, they’d be sending dick pics of course. she’d never open up about any of it just remain bashful, long story short we eventually broke up for good but remained in contact, she was still using me as her comfort crutch and essentially sharing her dating life, I loved it, idk why but being sick of being with her but still being wildly sexually attracted to her, this was the best thing ever, it eventually became messy when of course I started dating again and she found out, she’d call me complaining how these girls were ugly etc… at this point she’s living with a new bf and playing the same role she did with me it seems and thats when it all started

after dating a girl “officially” on social media I got the drunk call, “I fucked..” and she named about 6 guys she cheated on me with during our early days of dating. I’m guessing just a terrible part of her brain trying to exact pain on me for dating someone else, at this point she didn’t understand I had a fetish towards it more than it bothered me, she told me how big they were, how and where they had sex. A few stuck with me when she’d mention guys “bigger” than me. Probably hit that same part of the ego as the co worker in college but this time it excited me more than made me feel terrible.

in these stories told me how she’d cheated on her current bf with another guy who came in her and she wasn’t on the pill as she laughed, and i just said fuck it at this point and i said all this cheating on me and whoever why don’t you come over (this was over the phone) she did.. we had animalistic sex twice after she jerked me off while she told me about a guy she fucked while we were together, i was ready to go again after each story, she was clearly doing the same thing to this guy, she did to me. It kind of shattered everything i knew and cared about with relationships, I wasn’t mad, I was just indifferent. during this sex romp, we went a few rounds over a few hours, her bf worked out of state for long periods of time (bad move, guy) this is when I started asking for specifics and she pulled out her phone and showed me a picture, me wondering what it was, leaned over and it was just a massive, insanely comically large penis, and i said is that your bf?! and she laughed noooooooo this is…. we’ll call him chad, and i said?? who?? and she pulled up his facebook… it was a guy I had worked with a decade prior, before her and I even met, she’d have zero reason to know him at all but turned out she somehow became facebook friends with him, my best guess is he saw me in a relationship and creeped on her (she was insanely hot, i can’t let that part slip) and years later, somehow they must have been talking here and there, they met up, 350 miles apart and had sex twice, she bragged to me how she took the whole thing. If i use another porn analogy, think brickzilla but white, bend and all, if i had to guess 12” and the 9” girth, she said she couldn’t get her mouth around it but she could fit it in her (and pointed to her currently bare vagina all wet and opened up on my bed at this time) smiling at me like i should be proud, as she proclaimed her current bf was so small she lets him fuck her in the ass (which was off limits to me and everyone else she’d been fucking over the years besides a upcoming story-walmart guy). she eventually admitted she was looking through his pictures and could see an outline of his cock in khakis in one and the next time he pestered her to hang out, she invited him over and he drove 6 hours to impale her. this was while she was with her current bf, not me. I barely knew the guy, just worked with him but still made me think this girl is deep, down insane

at this point, I was just curious and horny and my brain was humming, thinking this girl is just absolutely toxic, she’d never mentioned penis size to me once in 5 years but somehow it seemed all the guys she seemingly seeked out for hook ups were massive

So during this time, here’s some of what she told me

One time while we were together apparently she’d left work, fucked a coworker in the parking lot and came home, jumped in the shower with me and I remembered vividly how “creamy” she was and wondered what was going on, just assumed she was horny and turned on, years later I learned that was a creampie from one of those “dick pic” guys I saw years prior she claimed was from the dating app but was really a coworker with a big, 9-9.5″ dick. The guy was like 19 and she was 22-23, I said you were fucking that guy? and she claimed only once but I gave him head all the time at first & without much prodding admitted she had sex with him a bunch of times and I quote “how could I not, his dick was huge”… and she noted how she’d slide him in and he’d cum right away so she’d suck him off until he was hard again. now I had tried to get her to be open and freaky with me in our relationship like this for awhile! She’d never bite, she always played the coy, nervous type, I genuinely did not think she had it in her to participate in a threesome, she just came off to me as the quiet, closet freak, and in theory that’s great but once you date one of them you realize it’s probably not so great, and it turns out the entire time she was doing about the most brutal cheating you can imagine.

Another story went, a night she was supposed to be spending with friends started on a boat in the afternoon with this random guy who i always saw commenting on her posts, (those posts about the lake) she said she went inside to change after the boat ride and her bottoms were off but top on and he walked in and said sorry I thought you changed by now so according to her she just on a chair and spread her legs and made him eat her out (this guy was like 40, divorced, a loser overall from her own descriptions, think lumberjack who survives on booze and mcdonalds) but he was like 6’6 350 lbs and she vividly described how his dick was like a monster can and when he pulled out he came so much she joked she thought he poured milk on her that it covered her stomach, face and in her hair, it was so runny she had to take a shower and wash her hair two times with his shampoo. As I’m in awe listening she goes on

That evening she went to her friends where she was supposed to stay, they went out, she ended up going home with another guy she sort of knew, this was the last night we were “together” and she did actually admit to cheating, now remember she’s finally spilling these stories a year later to me, that incident she stopped responding and basically went offline until the next day, i reached out to her friends who all just claimed they didn’t know where she went, she showed up the next late morning and was visibly upset, this was the first time she admitted to cheating, with this guy, who had a small dick and couldn’t cum and was so gross etc… etc… in that moment leaving out the part she had fucked another guy the same day while sober and he covered her in a bucket of cum, She was obviously not a great person, especially considering by this point I’d had opened fully up and would have been somewhat interested if she’d have been honest up front but she wanted the attention and must have just gotten off on the lies.

another incident she tied up the loose ends on, we matched with this couple, beautiful blonde girl and black guy, whom we both saw on the app and “liked”, the guy got her IG via the app. every once in awhile she’d show me the guys message, at first a video or pic of the guy with his gf having sex or her laying on the bed covered in cum, eventually she said he stopped or so i thought, I’d randomly see her phone and open the convo and it would just be pics of him with his dick out (of course huge, down to his knees, probably 10-11”) or a video of him jacking off, usually she didn’t respond except one time it was a video of him and his gf in his vehicle, she was riding him from behind, it was zoomed in so you could really only see dick, pussy and steering wheel in and out of sight, it was like 30 seconds long , she was squirting and he pulled out but was shooting cum into her, like tip just barely out but her holding her pussy open to shoot it in, than stuck it back in and cum and squirt was just gushing out, I remember seeing it and asking her if she’d want to meet up with them and her saying idk she seems hot but he seems pushy and weird, what threw me off was she actually responded, she said yumm with a heart emoji,

my presumption was she responded because it was a hot video simple as that, turns out that was her, he filmed it and sent it to her after the fact. She said he had her number and they’d text, which I did not know, he was in the area one day and he said “I want to shoot my load into that little pussy” and she said “please ? “so the act of shooting it in and recording it was pre planned, I thought, that was hot, didn’t make me angry at all, she seemed to not like that, almost like she was trying to hurt my feelings, I don’t think she understood the dynamic I was into still l. she said he came so much in her and the angle made her squirt so hard (for the first time, I’d never seen her squirt, I don’t think she was aware she could) and she said she felt like she was peeing but knew she was cumming, this was while i was at work and they were in a walmart parking lot apparently, she said they went inside, she had a skirt on and no underwear and he asked her to walk with his cum dripping down her legs, which she did, and he took a video of but I never saw it. They got a morning after pill, she took it and they walked out to their vehicles (she had an SUV) and he said we should have done it in there, theres more room! She always had her seats folded down for the dog, so she said she nodded to the back, and didnt know why because she was done but felt like she had to say yes, and she said he just put her on her stomach, pulled up her skirt and in her words “pounded me so hard into the floor I thought I was going to break through it” she said he power fucked her for 15-20 mins to the point she said she squirted again and felt like she was going to pass out, without asking he spread her cheeks open, and she said his dick was so creamy from her he somehow got it about halfway in her ass and she told him not to go further so he stopped and she jerked him off since she couldn’t take him thrusting, she said she thought he was going to rip her open if he started pumping, but he was so big she could just jack him off while still filling her ass up, she said his 2nd load was bigger than the first by far and it was bubbling out, while he was still in her ass, the only real defeating part was it was the first time shed ever done anal was with a random black guy in a walmart parking lot, they parted ways, she said she drove home with cum leaking out her pussy still and ass while making a puddle on the seat. i didn’t know about this for 2 years. I recalled the day easily, when i got home she was scrubbing the back of her vehicle saying the dog puked, still in the skirt and I could see her ass out the bottom so i started grabbing on her and she got mad and said gross ik cleaning up puke, when in reality it was her squirt all over the carpet, and i vividly remember her not wanting to have sex that week out of the blue because she was sore, which made no sense to me. now she was telling me this story with my dick in her hand and I came harder than i’d ever come before, as she giggled while discussing her cleaning up the mess that day, complete psychopath, but I loved it. She said she wasn’t sore at all she was just worried I’d be able to tell she got fucked in the ass by a giant black dick. Her words

fast forward a few years, a few quick relationships with safe girls, none of which i really opened up with any of this too, just safe flings, who I think in retrospect helped me rebuild my confidence, i met another skinny, hot, big ass, small tits, much different personality than that gf and upon chatting her up we start talking sex, our kinks, likes etc… she mentions how she loves bbc, mainly from porn and eventually just dating a few black guys and i remember saying ya it is a stereotype etc… and she said not really a stereotype if its true and i said huh? and she says i’ve been with 4 black guys and they are all “slangiiiiin dick” jokingly to me and i said to myself “this is my girl” shes not hiding it, shes open, she doesn’t care what I think… so long story short I’ve been with her for 5 years now, we are happy, we have sex daily, sometimes 2-3 times, we go on vacation, we get on dating apps, she exclusively selects black men who advertise large dicks, we’ve only been with 2 in that time, both times they were averging 11-12” and girthy, one time we dp’d her and she loved it, she cums and squirts and leaves happy and we go back to normal life with more memories and a few video clips. everytime we travel we look on the dating apps, she selects a few guys and talks them up, were usually busy and content and it doesn’t work out but her kink is always there and i guess so is mine now ?

I think cuckolding is a combination of things for many people, mine was shedding my ego, opening up my sexual experiences and also understanding relationships aren’t all about control, and once you relinquish one or all of those things, the sexual universe really opens up and you know who to seek and what real honesty and communication really is


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