A bit about myself first. I'm 28 years old, and would describe myself as not an exceptionally nice person, although not horible or anything like that. I think i'm nice enough to the people who are normally around me, but when it comes to the men in my life I tend to gravitate towards humiliation and abuse. I end up staying with the men who enjoy it, since the ones who don't tend to run away really fast, if they're smart. I'm not a bad person, just one that enjoys seeing some men at their weakest.
Visually, I stand at 5'5", blond hair, well, see the pictures please, you're all grown up men here. My boyfriend at the time was a classic "gamer guy". Kinda chubby, low paying job, lazy, and (most relevantly) a tiny dick. Not super tiny, i'm not talking micro penis or anything like that, just small enough that it didn't hit any good places, and wasn't very satisfying. This whole thing happend when I was 24, so quite a while ago. I've just been browsing this blog a lot and decided to post this story, just to have a way to tell it, I don't normally get the chance to but I like reliving it and, as I said, it's hard to find guys who would take this.
So, me and my bf at the time dated for about 3 years. Near the end of our relationship I really started to dislike his attitude towards life. I guess I just ended up being a type-A and he ended up being a type-B. We started dating after college, so I guess we were just pretty insecure about relationships at the time. Looking back it was pretty clear we shouldn't have been together, but we were too young to act in a good way. He was so lazy and complacent all the time. I tried to keep up a facade of liking him, but secretly I really just resented his lifestyle. We started living together after about 2 years, and I really grew fed up with him then.
A few months before we broke up I started to fuck this other guy, we'll call him Josh. Josh was a guy who was more up my alley, we met at a mutual friends party and instantly hit it off. He was way more upfront and aggressive then my bf. Josh was 6'1" and bf was 5'9", Josh could actually look good in public while my bf just wore shorts and a t shirt everywhere. And Josh's cock was PHENOMENAL. Otherworldly. Etherial. It was everything I wanted out of a dick.
Me and Josh were lying in bed one night when I had convinced my bf I was going out to my friends house for a party. I was complaining about my bf and he was listening silently. He had just accepted that I had a bf right from the beginning (I decided to be upfront about this right from the get go) and had never said anything about it. Tonight I guess something snapped in him, he just said out of nowhere "why don't you just break up with him?". This was a startling thing to hear as it was something I hadn't really thought about much. Even though I felt some resentment, I guess I was pretty complacent too, so I just assumed I would be with him forever. I thought about it a while and came to the conclusion pretty quickly that I liked it in some way too.
This is where I learned that I love to humiliate people :)
When I decided to try this, I started feeling so powerful. I think my bf started to see a difference in my behaviour, he kept asking me if I was ok, if there was anything I needed to talk about. He just accepted when I said no and went back to whatever he was doing. I decided I wanted to humiliate him, by making him think I was going to break up. Humiliate him very badly. I talked to my Josh about this and he suggested something completely mischievous. He proposed that I let my bf walk in on me and Josh fucking. the idea turned me on so much me and Josh fucked right then and there.
The day came when we decided to make it happen. BF was out seeing a movie with some of his friends. I had Josh come over and we spent the length of the movie teasing each other. We didn't want to let either one of us cum before my bf saw us. We did this until I heard the front door of our apartment open. I pushed Josh onto the bed and started riding him, positioned so I was facing the door to the bedroom. BF called out for me, "Babe, are you asleep?"
"No." I said while panting.
"Are you ok? Are you working out?"
"No I'm not."
My heart was racing, the sex was feeling so good from all the teasing, his massive cock was pounding into me, I could feel him through all of me, each time my pussy came down on him it felt like a lightning bolt through me. Doing this while my bf was here was making me ecstatic, my body was shaking from excitement. Then my bf opened the bedroom door. Our eyes connected, he seemed to take a moment to visually process what he was seeing.
Me, riding a big cock while moaning in ways he had never heard me moan before. His jaw dropped open and just hung there, he seemed to stop breathing. His face had a look of fear, but his eyes had that look that men's eyes get when they want to fuck. My moaning grew louder, and I came while staring at him, all the emotion and excitement made me burst, squirming and whimpering on top of Josh's dick. After the convulsing stopped, I regained some of my composure and looked straight at him and said, "He's much bigger then you."
Josh knew what was up, because he pushed me up, got up, positioned himself behind me and thrust into me doggystyle. I started moaning again, and my bf backed against the wall and slid down onto the ground. Seeing him like that awoke something in me, I couldn't help myself from continuing to insult him. I said so many things to him, I insulted his friends, his life, his dick, his clothes, everything. When he started to shake I came again.
After my second orgasm Josh started really fucking me hard. Grabbing and pulling my hair, spanking me, even sometimes joining in with my insults. My boyfriend just sat there in the corner almost panting, with his dick making a tiny tent in his pants. I mentioned that several times. My bf couldn't say much other then the occasional "why" or the odd "no", which turned me on SO MUCH. After doggy for a bit, I got up and positioned Josh so that my bf could see me as I devoured his cock, at least as much as I could get in my mouth.
I tried to put on a show and act like a pornstar, just so my bf would feel even more jealous. After sucking for a bit he picked me up and threw me on the bed, pushed my legs up, and began to pound me missionary. He pounded me so hard, the clap of his body hitting mine was loud. It was by far the best sex I've ever had, both before and after. Josh looked up and said to my bf, "I'm going to cum in her." I felt Josh push deep inside me and start to cum, and I had the biggest orgasm of my life.
It was so powerful I could barely breath. It was violent, but it was incredible, I still masturbate to that orgasm. When my orgasm died down I stood up and walked over to my bf. I stood over him, thrusting my hips out so he could see my red and swollen pussy. I asked him, "Do you love me?" He had stopped shaking now, he paused a bit and answered "yes".
"Do you want to leave me?" I asked. Again, a pause, "no". "Good" I said, "Now clean me up" and he leaned forward slowly and started to eat Josh's cum out of me. I told him to go sleep on the couch. He left, and me and Josh laid together, and later fucked again.
I wanted to go into that with the intention of breaking up with him as a cruel, temporary joke. But I got so into the moment that I became someone else, someone that wanted to keep my bf around. I actually had feeling for him and through the humiliation, we both connected. It was something that I had been keeping in me for my whole sexual life, and having it out in the open felt incredible. The next morning me and my bf talked about what happened. He was heartbroken at first, but eventually became excited and incredibly turned on, I've never seen his penis so hard and even his size was a bit more. He told me he loved me and I felt myself saying it back, even though I don't know how that came out of me. He wanted me to do it again for him.
We ended up staying together quite a while longer, and eventually broke up for other reasons. All my men since then I have been very upfront with about what I want, and my relationships since then have been quite fulfilling. I also don't talk to Josh anymore.
So yea, that's the story. When I got more into the cuckolding community and more in tune with myself I felt bad about what I did, and eventually apologized to him, but If I were to go back I would do it again, in a heartbeat.
Thanks for reading! Feels good to actually type this out. Sorry for any typos or grammar errors that might be wrong with it.