Testicles getting squished during sex (accidental)

There was a request for accidental busts going around this subreddit and this reminded me of sex with my last ex-girlfriend. I'll call her Jane for the sake of this post. One big thing about having sex with Jane was that she was a BBW weighing well over 300 lbs. I didn't care, I've been with heavy women and light women before, and I think they're all special in their own ways. That being said, when it comes to sex with a bigger woman, one thing that can be a bit tricky is having sex with the BBW on top, riding. When things started to get physical, we had a conversation about things that we always wanted to try but never got to. For Jane, that was being on top during sex. While I understood that it can be difficult to get the woman on top during sex, I was still amazed that a woman in her thirties with multiple partners never got to be on top during sex even once. I agreed to let her try it for the first time.

I'll be honest, it was definitely a little intimidating, letting such a big woman put her body weight on me, but I figured, what's the worst that could happen? With me lying on my back, she leaned over me and hopped on my penis. At first, everything felt fine, mainly because my legs were spread out. However, she wasn't able to remain stable on her legs spread out that wide, she needed to pull her legs in as well as rest her weight on my legs. "No problem" I think, not realizing what this was about to do. with her on top and my legs pinned close together by hers, my testicles were bunched together tightly. Now she once again mounts my dick, and reaches the bottom of my shaft, then drops yet more of her weight down, so that her body weight pressed down on her ass, which is pressed onto my trapped testicles. Feeling this pressure against my balls, I reflexively let out a moan. She hears this and takes it as a sign that I'm enjoying it.

"Feels that good?" She asked with a chuckle. Without even thinking, I respond "yeah" reflexively. I figured it was just a one time thing. Especially since once she settled on top of my dick, the pain started to subside while she was sitting still. Unfortunately for me, this wouldn't last long. Starting to get used to the sensation of being on top, she then starts to rock her hips back and forth. She alternates between forward and backward and left to right. Left to right isn't that bad, but when she goes forward to back, she ends up putting more and more of her body weight on my nuts. For my dick, everything feels great, but for my balls, this quickly became agonizing. It was just good enough to remain hard, but just painful enough not to cum. After a few minutes of her rocking forward and back, pressing down on my balls again and again, I try to communicate something to her, but between the sensation on my dick and the pain in my balls, I'm barely verbal. "Jane..." I mumble out during a brief gap in between her testicle presses. Before I can say anything else, she immediately responds "Jared...". I guess she thought i was just saying her name out of ecstasy. Even if I could verbalize what I was experiencing, I didn't think I could bring myself to ruin her fun for her. I could feel her wetness and hear her moans of pleasure. It also dawned on me later that all of the signs of me in pain probably looked like pleasure to her. My moans, the faces I made, even me buckling forwards as pain signals from my ballsack shot up to my stomach. The line between ecstasy and agony had become so blurred.

After it was over, she thanked me for finally letting her go on top and how much she enjoyed it. She rarely came from penetrative sex, so this was a big deal for her. She then asked me what I thought and I was truly torn. On one hand, I was genuinely thrilled how much she enjoyed herself, but on the other hand, the idea of putting my testicles through that ringer again terrified me. I decided to split in the middle, I told her that I really enjoyed it too, but that at times my legs being pressed together was a bit uncomfortable. She said that it was no problem and we can definitely adjust that next time. She seemed happy, though a part of me remembers her sounding a bit disappointed. I'll be honest, I was actually kind of hoping there wouldn't be a next time. This ball-pressing sex was not enough force to do anything crazy like damage my balls, though I did wonder what would happen if this kind of force happened consistently over a long period of time. I decided to just not bring it up and hope she would forget and move on.

That didn't last long. It took only about three days before she wanted to go again. I asked her what made her want to do it so soon, and she told me that since we tried it the first time, she spent a lot of time looking up porn of sex where the woman is on top and that she had an idea for my comfort issue that I had mentioned last time. So after undressing, she once again has me lay on my back. Only this time, instead of my legs being straight forward, she has me pull my knees up, and spread my legs way out to the side. Then she sits over me and guides my dick into her vagina. "See babe? this way your legs won't be closed together". She was right, they were fully spread eagle this time. After guiding the head of my penis inside her, she quickly drops her weight down onto me. I'm caught off guard by this, and grunt loudly as she slams her weight down onto my testicles. It turns out, even though my legs were spread, she was still putting her weight on my balls because the way I pulled my knees up also pulled my ballsack up to where it was resting vulnerably on my taint. This time she gets to work going up and down on my dick (and balls) rather than the rotating motion she did last time. Now that my knees are tucked up, she can use them as leverage as she lifts herself up on my dick, and then drops her full body weight, slamming down onto my helpless testicles. Much like the first time, I can't do anything but make faces and groans that are again interpreted as signs of pleasure. I can't even hunch forward at all because my lower half is lifted up. All I can do is watch as she enthusiastically lifts herself up and down on me, punishing my nuts with every drop. The only consolation is to see her face and see how much pleasure this is bringing her. Trying to endure, I grip her thighs tightly. When she sees this, guides my hands to her breasts, but continues her bouncing on my testicles. To take my mind off it, I focus on fondling her tits, but when she slams her weight back down on my balls, I reflexively pull more firmly on her nipples, which judging by her reaction, felt great and added to the orgasmic feeling that she was getting from riding my dick and pressing down on my balls. As she finally came to an orgasm, she returned to her older ways. She slams down on my nuts one last time, and proceeds to rock back and forth, giving more, smaller presses on my orbs as she cums on my dick. Neither time I was able to cum, though I told her otherwise.

Mercifully, she finally hops off. Still breathing heavily, she takes to fondling my still-hard penis and my battered ballsack thanking me for a great night and promising me many more.