His Pain, Their Pleasure

Hello all! This is another story I had written a while ago and posted on Tumblr that I wanted to share with you all! Hope you enjoy, and let me know your thoughts down below!

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(Based on a true story)


Natalie was a young brunette with wavy hair reaching just below her cleavage. She was tall, around 5’7” with a petite but curvy and athletic figure. She was 19 and had lightly tanned skin with soft but deep green eyes.

We had been dating for 3 weeks now, and had been on several dates but they had all ended the same way. I would walk her into her apartment building, ride in the elevator with her to the 32nd floor, and eagerly follow her to her door only to receive a hug, a kiss on the cheek, and a painful erection as she gazed into my eyes to thank me for the date.

God I wanted her.

But tonight was different. I joined her in the elevator, followed her up to her door, but this time after she unlocked her door she wrapped her arms around my neck and pulled herself up to my face to kiss me. As she slowly let herself back down to the ground, she gave me that familiar gaze. She lightly grabbed my hand and guided me through the door and into her small studio apartment.

It was dark, but I could tell that she kept it neat and organized. She didn’t give me much time to look around though as she pulled me through her living room into her bedroom and started to undo my belt. I went along with it and leaned in for another kiss as we both disrobed and buried ourselves under the blankets of her bed. We didn’t waste any time getting to work as I was already rock hard from the moment she kissed me in front of her door. My dick rubbing up against her neatly shaved pussy. I reached my hand down to guide it in, but her pussy was still dry.

We paused for a moment and with an impish smile she asked ”how much do you want me?”

I replied “I would do anything to have you.”

And with that, she rolled out of bed and reached back towards me. But this time, she wasn’t grabbing for my hand, she was reaching lower.

She wrapped her hand loosely around my balls and led me into her bathroom. With a wide smile on her face she released my balls and lifted the toilet cover. Confused, I asked her what was going on, and she instructed me to kneel on the floor and put my balls on the seat.

“You said anything remember?” she teased.

I definitely wasn’t expecting this when I said I’d do anything, but I was willing to try it if it meant I’d get to have her. After all, how bad could it be? I obeyed and rested my loose ballsack on the seat and she slowly lowered the cover to sandwich my vulnerable balls between the seat and the cover.

She pressed down a bit on the cover, enough for me to feel the dull pressure in my balls. What had I gotten myself into? Natalie let off the cover and I regained myself, but not for long as she stretched one leg across the cover and sat down on top of it.

With my balls being crushed flat under her weight I yelped in pain and instinctively tried to pull back, but it was to no avail. My balls were firmly squished under her and could not escape. She smiled even wider than before and leaned in to kiss me and drown out my cries. Then she scooted her body forward on the seat, her body inching closer to mine.

As the pressure on my balls increased, so did the pain I was in, immensely. But Natalie knew this and she was loving it.

As she continued inching closer, my still hard cock came into contact with her pussy, which was now soaking wet and leaking out into the toilet cover. Without removing her lips from mine, she reached down and in one slick move slid her pussy around my pulsing cock.

Holy fuck did it feel good. The warmth. The tightness. The moistness.

The pain was immense but so was the pleasure. My body was confused to whether or not it should be enjoying this. But Natalie was certainly loving every moment of this. She moaned into my lips and she began to bounce on the seat, both flattening my balls like pancakes and riding my dick like she owned it.

She moaned again, and started bouncing harder and faster on the cover. I wasn’t sure how much more my balls could take, but after only a few minutes she slowed down her bouncing as she reached orgasm, and feeling her pussy squeezing and releasing my dick inside her, I found myself cumming inside her. Her body weight crushing the cum straight from my balls.

We both sat there for a minute, regaining our breath. She then leaned back in to kiss me harder and I groaned from her weight still pressing down on my tender balls.

She stood up, lifted the seat and we watched as my balls reinflated after having supporting all of her weight. Neither of us were able to say anything in excess of “wow.”

We both cleaned ourselves up and returned to her bedroom where we laid down and quickly fell asleep. My hand caressing her breast, her hand gently laid upon my balls.