The Best Kind of Railing

Masturbation Month 2024 #27 (Link to Part One)

Times past when Frank had wanted to be fucked hard and powerfully, and Cynthia hadn't been able to bring it, for whatever reason, he had resorted to suction cup toys. Solo play was never as satisfying. No matter how good the toy felt as he thrust it into his ass, precisely fast and deep enough, without Cynthia there it was never as exciting. There was something magic about being witnessed by her in all his trembling lust and vulnerability.

So, the situation she'd cooked up tonight was perfect. They'd played with the harness only once before and had issues with it holding the toy well enough, plus Cynthia was sitting on the side of the bed. The angles and height were all wrong. It got thrown into the back of the drawer and forgotten about.

The harness seemed to be working perfectly tonight, thankfully. That toy wasn't going anywhere but in and out of his ass, as soon as he felt ready. Right then, their kissing grabbed him as sure as that cage had his cock. He couldn't have pulled away if he wanted to, and he most definitely did not want to. The combination of his ass feeling so filled up and sensitive, along with the simple deliciousness of Cynthia, made his head spin.

She was right there facing him, as hot as ever. He didn't usually get to see Cynthia when she fucked him. Missionary was a difficult position and they usually defaulted to other ones. All her sexiness directly in front of him totally frosted his cake. The girls looked amazing. He loved Cynthia's tits! A small voice in the back of his mind said it would be way cool if the next time he was allowed to have an orgasm, he could come all over them. Frank smiled at that thought and recognized it immediately as his cock talking.

His ass had the mic now, though. So, he pulled back reluctantly and spoke on its behalf.

"May I fuck myself, Ma'am?" He wanted permission before he jumped on this train, the train he could feel rushing at him. Frank knew he was in for a serious and self-imposed railing, the best kind of railing!

"Yes, Frank. You may."

There it was. Permission granted! The train thundered closer. One more thing to say before he jumped.

"Let me know if I get too heavy or hurt your leg, okay? I might go a little crazy with this. It feels so fucking good!"

"Oh, absolutely! Mmm... Can't wait to see your crazy..." She kissed him again.

Frank leaned forward, into the kiss. He clasped his hands behind Cynthia's neck for balance. The girls bumped up against his chest. Damn. He closed his eyes and jumped on that train. Leaning back onto the toy, he broke the kiss.

Suddenly Frank felt very slutty, putting on a show like this for Cynthia, and it thrilled him.

First, he moved slowly and deliberately, exploring until he found just the right angle, depth, and speed. Then he began riding in earnest, like a well-oiled machine. The endurance of his legs might be a limiting factor, he realized, but that point was a long way off.

Cynthia watched Frank with fascination. Watching him masturbate was always a thrill for her, but this was next-level stuff! He moaned, squirmed, and slammed his ass on her leg, holding onto her tightly for balance and leverage. Once when he rose up off the toy Cynthia pushed up in a calf raise and shoved it back inside him as a surprise.

Frank gasped and looked at her in amazement.

"Oh, yes, babe! Yes!!" He stayed motionless above her leg as she rapid-fire pistoned with her knee, making the toy go wild inside Frank.

His reaction made Cynthia very glad one of her favorite exercises at the gym was calf raises.

Frank was beside himself, making the sounds she loved. Sometimes when she fucked him, he sounded like he was in pain. But, after multiple assurances, she trusted that he was just overwhelmed with pleasure. He couldn't stop those sounds from coming out, but they always meant ecstasy. Frank was chasing all the pleasure he could find, relentlessly. The best kind of a railing was indeed relentless.

They fell into a bit of a rhythm. She left her foot flat, and Frank would ride the toy forcefully for a while. Then he'd raise his ass up a bit, and she'd go to town with the calf raises. No breaks for Frank's ass. None. They went back and forth 4 times without a break, until the intensity of his moans grew. Each thrust into his ass brought a kind of roar out of him, primal and deep. Cynthia wondered how long he could keep this up. His cock was streaming pre-come from the confines of its cage,

Finally, about 15 seconds later, Frank stopped moving and held up one hand, breathless.

Cynthia held onto him as he slumped against her a bit, speechless, the toy buried inside him. His every breath was a gasping moan that got quieter as he calmed down.

That was an insane amount of pleasure," Frank said when he finally caught his breath, "but I think I'm done." They kissed again softly.

"Well, I have to say. That was the hottest 'crazy' I've ever seen, Frank! Fucking sign me up!"

They just laughed for a bit, holding onto each other. Finally, Frank gently rose up off the toy, disconnecting from her. He took the harness off Cynthia's thigh, and she jumped in the shower to rinse off. Frank cleaned up everything, smiling as he replaced the chair in the dining room. Perfect choice by Cynthia; sturdy and the right height. Harness play rocked!

Cynthia climbed between the covers as Frank took his turn in the shower. She immediately reach for her vibrator and enjoyed 2 quick orgasms, replaying the scene in her head. Fucking hot! Astonishingly hot! Wow.

Frank let the hot water beat on his back and leaned against the shower wall. He was still kind of swooning, like he did when he first sat down on that toy. Now it was his exhaustion and the post-ass-fucking yummies. It was a thing that happened to him when Cynthia fucked him. In that moment, he had a shit ton of the yummies. So, he just leaned against the shower wall and enjoyed it. He took stock of his ass. Butt cheeks were pretty sore, but he deserved that, letting himself get hoodwinked by his cock. Then he checked his hole. About the same level of soreness as this morning, which was surprising after all that action. He felt proud at that discovery. He was really getting the hang of this!

Coming to bed, he wanted to share his news with Cynthia, but found her snoring softly with the light still on. Frank's body was still buzzing. Everything felt good. The smooth sheets, the warmth of Cynthia's back and ass as he scooted into a big spoon. He loved the yummies.

Frank's cock, secure in its cage, was enjoying the yummies, too, and finally stopped pouting.

Part 28 - Freedom Beckoned, if Only For Two Full Seconds

Masturbation Month is celebrated every year in May. Let yourself sink into self-pleasuring and join the fun!