Masturbation Monday

Reinventing Himself #MasturbationMonday

After the reactions to last week’s “He Waits” post, I wanted to give him another story – a chance to change. Enjoy!

Still fuming over being stood up the week before, he’d finally told Mother that she needed to back off. He’d been following her rules all his life, and where had it gotten him? Sitting in a restaurant by himself, fantasizing about a woman who never had any intention of meeting him, and hard as a rock.

He knew women laughed at him behind his back. He knew that the guys at the gym thought he was weird. He looked in the mirror every day and saw what the rest of the world saw – a gangly, pale, thin, nervous-looking man. He was fed up!

“I’m fucking tired of this!” he shouted. Using such language still felt wrong somehow, but he shrugged the feeling off. How was he ever going to have a different life if he didn’t behave differently?

First thing’s first, he needed to move out of Mother’s home. She was stifling him, keeping him a little boy. He was a man, damn it! She hadn’t appreciated his assertion that morning during breakfast.

“Mother thinks I can’t make it on my own, but I’ll show her,” he whispered to himself as he began an online search for an apartment. He pored over pictures and descriptions for hours, worrying about location, safety, and price. Finally, he narrowed his picks to three or four and made plans to view them the next day.

He wasn’t sure why he’d never moved out before. His job paid him well, and he could certainly afford to live on his own. He wondered, for a moment, if Mother would still help him with laundry and cleaning. He shook his head violently. What was he thinking? He was going to be a man from now, and he didn’t need his mother! He’d live in filth if that’s what it took! Straightening his shoulders, he felt more determined than ever before.

He wondered if his perfect girl was out there. For a moment, he felt sad. Then he shook himself again. No! If he was going to be a man, he was going to act like a man. Casual dating, casual sex, no strings! The last thing he needed was to get tied down to a woman like Mother!

Was he man enough to handle casual sex? Could he pick up a woman in a bar? Questions filled his mind, followed by self-doubt. There had to be an easier way to know where to go and what to do, he thought to himself. A quick Google search later, and he wondered how there could be so much porn on the internet. He wondered how he’d missed out on all of it over the years. He grimaced to himself as he thought of all the evenings spent watching TV with Mother, driving Mother around, and spending nearly every waking moment with Mother.

Still fighting years of Mother’s influence, he found some images hard to accept. Page after page of beautiful, naked women touching their pussies, being fucked by one or two men filled his vision. He came across a short video of a man nestled between a woman’s legs, licking and sucking her pussy and clitoris. The man made love to her with his mouth. He stared in wonder and licked his lips. Why had he ever thought this was a bad thing?

His groin tightened, and he shifted uncomfortably in his seat. Normally, he wouldn’t consider masturbation during daylight hours – the fear of an unannounced entrance from his mother usually cooled any ardor he felt. After their argument, he’d installed a lock on his door and was keeping it locked tight. The more he watched the scene in front of him, the more unbearable the ache became.

Finally, he couldn’t take a moment longer. Pulling his cock out of his shorts, he gripped it hard. Keeping his eyes locked on the screen, his hand began to stroke the length of his shaft. Precum pooled at the tip. He used the sticky fluid as lubrication and closed his eyes as his hand glided up and down easily. Groaning quietly, he picked up speed, feeling his balls tighten. He wanted this to last longer, but he knew he couldn’t contain himself. Grunting as hot cum shot from his body, he opened his eyes in time to see the woman gush ejaculate over the man’s face. He smiled to himself. Yes, he could be the type of man who performed cunnilingus. No, that’s wrong, he thought. He would eat a woman’s pussy. He smiled again as he thought about it.

After cleaning himself off and changing clothes, he knew he needed to find a way to feel more like a man. He would move. He would cut the apron strings. He would reinvent himself. He would date and have casual sex as often as possible. Sitting back down at his computer, he did a little more searching and found exactly what he was looking for – a casual dating site called XXX Sex Guides.

This post was brought to you by XXX Sex Guides.

About the author

Kayla Lords

I am a sex blogger, podcaster, freelance writer, international speaker, kink educator, and all-around kinky woman. You can find me online sharing my innermost sexual thoughts and experiences, teaching other bloggers how to make money writing about sex, and helping kinksters have happy healthy BDSM relationships. I'm also a masochistic babygirl submissive with an amazing and sadistic Daddy Dom and business partner, John Brownstone. Welcome to my kinky corner of the internet!


  • I like this, when you first brought him out as a character he came across to me as being creepy. Reading this it is like he redeemed himself. It is as if he didn’t know he is creepy and is a victim of his mother.
    Mommy Dearest

    • I was surprised, pleasantly so, by all the different reactions to him originally…but he was viewed in a way I never intended, so I had to give him a little redemption…just a little…

  • I’m pretty sure I dated this guy in high school. He called my ‘Mommy’ during intimacy!
    If this guy comes out of it a dom, I’m a little nervous for his first sub. he’s got some serious mommy issues to work through. 😉

  • I don’t know if you ever feel like you’re giving your characters life, like I do. I just didn’t want this one unleashed into the world without some gentle guidance. Hey! Maybe he needs a domme!

    • If I understood the dynamic of male subs and female Dommes, I might be able to do that…

      Most of my characters are usually based on *ahem* myself…but yes, for the male characters, I do feel like I’m giving them life…and it’s a strange feeling when they cause a reaction I didn’t expect.

      I don’t know what will happen to him…I don’t want him to be a cliche, but I would like him to have a better life…

  • I know you read Dumb Domme. Honestly, to me her words are so much the words of a person who loves. Sometimes, I cannot distinguish her dominance from my own submissiveness. Besides, you know the sub is the one in control. 😉

    • Shhhh! Don’t give away our secrets! 😉

      I think D/s is a give and take thing as are most relationships…there really is equality (in a sense)…if you squint your eyes and open up your mind to abstract thinking… 🙂

  • Don’t get me wrong. Playing without a safe word gives up control. Certain men lose control and play too far. I think the non-sexual parts of the relationship should be very equal.
    What I really love is the illusion of having no control, of letting go of having to be responsible for my sexuality, of having to be a nice girl, of worrying about whether I’m acting like a slut or not, and just getting to be a Sexual Being.
    Hmmmm, where have I heard that phrase before?

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