The Fifth Day Was Full of Reminders

This flower vase if full of reminders about the pegging Cynthia gave Frank!

June 2, 2023 #23 (Link to Part One)

Frank’s fifth day was full of reminders of his punishment the night before. From the moment he got up, even sitting on the edge of the bed, his butt smarted. He checked his cheeks out in the bathroom mirror before his shower. Yep, a few marks, as he’d expected. They stung a bit with the hot water.

There was nothing like a good beating. It forced him to be in the moment so powerfully. Nothing else existed but his butt and whatever Cynthia used to deliver his ‘punishment’. He’d slept surprisingly well and suspected that was also a benefit. Once again, he thought about asking for nightly spankings when this week was over.

Cynthia was still in bed when he slipped quietly out the door to work. This time he was the one to leave coffee for her with a note next to it that said, Love you! Your Slut Boy.

Then he found himself immersed in his day, full of reminders. Sitting in the car, at his desk, and on the toilet - they were all a little painful. That was quite a beating she’d administered; just the way he liked it. He preferred to have a few marks that he could look at and be proud of for a few days. And the soreness brought his mind immediately back to getting fucked, getting beaten, and the apron. All of it! He felt his cock throb in its cage.

Things could change, but on day five Frank would swear that he would someday look back on this week as one of the best of his life. Living out fantasies could be fuck-all powerful. If they played out well, of course, because not all of them did. Lost in a reverie of aprons, panties, his caged cock, and his sore ass, little work happened at Frank's desk that day. He thought about so many other things.

Sharing this fantasy with Cynthia had been so difficult. The things he was asked for flew in the face of society’s fucked up definition of masculinity. A lifetime of indoctrination didn’t just disappear because he discovered it was all bullshit. So it still felt excruciating to express his desire for chastity, frilly and feminine things, and being fucked. It took courage to be that vulnerable and a lot of trust in Cynthia. She responded even better than he’d hoped. A dream come true. He smiled to himself, sitting at his desk, still not working.

Whenever he and Cynthia shared new kinks and desires with each other, they had an understanding that there were no expectations and no judgements. Everything was approached with an exploratory attitude. Above all, they practiced gratitude for the information given. This created a container of safety that allowed for more open sharing and exploration between them. Just to know Cynthia fantasized about experiencing DP with another guy was fucking hot, even if they never brought another person into their bedroom.

His phone dinged. It was Cynthia.

Hey, Slut Boy! I want a status report on your butt, ass, and cock. The report needs to be accompanied with photos of 1) any marks on your butt and 2) your locked up cock. Before lunch, K?

Frank felt a little ambushed. WTF? Seriously, Cynthia? Then he looked at the clock. Two hours before lunch. This was doable.

Good morning, Ma’am. Will do.

Inspired by her words, he headed off to the bathroom. His mind wasn’t on his work anyway. He chose the single bathroom at the end of the hall where he could relax and enjoy himself. He locked himself in and pulled down his pants.

Getting the right angle to show the marks on his butt was not easy, he discovered. After some trial and error, he had the pics he needed. Then he started to take a pic of his caged cock but hesitated. Felt silly, but he wanted to send Cynthia a pic of his cock straining against the bars instead of just relaxed in its cage. It seemed sexier.

Setting his phone down, he started caressing his balls with one hand and flicking his nipples through his shirt with the other. He pressed on his taint and felt the nearby slight soreness of all the anal action he'd endured. More to come tonight! He teased himself until pre-come was dripping from his swollen, constrained cock. Carefully taking a close up, he captured the glistening pre-come and the desperate appearance of his cock being denied an erection.

Though Frank sat on the toilet, no part of it was visible in the pic, and that was purposeful. He never understood why anyone would take a picture of their cock while they sat on the toilet. Oh, that’s sexy. Not!

Frank pushed some toilet paper into his cage to soak up the pre-come and went back to his desk, where it was even harder to concentrate. His shirt rubbed against his nipples. His locked up cock was talking to him; pretty much a constant WTF, dude? And his sore butt had him shifting around in his seat.

He composed a reply text to Cynthia.

  • Butt: Smarts when sitting down. Several marks (see pics). My butt is full of reminders of our play last night. Thank you, Ma’am.
  • Ass: Still slightly sore. When I did my business this morning, I could feel it, butt (ha ha) no worse than yesterday. Good to go for tonight, Ma’am.
  • Cock: Desperate for release. Begging! Weeping! (see pic) Please, Ma’am!

Frank proudly pushed the send button and made sure the pics had sent. Fifteen minutes early!

Work wasn’t really work that day. Instead he fantasized about Cynthia throttling his ass again later. He made three trips to the bathroom to replace the tissue in his cock cage. And every time he sat down he winced.

On the way home Frank stopped to buy flowers for Cynthia. Purple irises and pink roses. He hoped the sight of them would be full of reminders of his love and appreciation for her. He had them in a vase on the kitchen table when she arrived home shortly after he did.

Part 24 - His Heart Swelled, Along With Other Things

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

2 Responses

  1. I just started reading this series a few weeks ago, and I’m just in awe of this highly charged erotic adventure. The scene descriptions are inspiring (i e., they get me hard), and the interaction between Frank and Cynthia is what all D/s should aspire to (actually, any relationship). It probably helps that the series hits nearly all of my fetishes.

    I especially like the links you embed to other posts, like The Beating in this one, for context to your meaning. I didn’t really pay much attention to those until the last few installments and and to go back to catch others.

    I’m anxious to see what the next three days brings in this adventure. I just hope I don’t have to wait for it until the next Masturbation Month.

    1. I’m glad this series is frosting your cake! I do plan to jump back in to it before long and not make people wait another entire year… even though I am a sadist! 😉

Leave a Reply

Your Source For All Things Pegging

Information and resources for anal sex, bdsm, strap-ons, intimacy, and female domination. Let Ruby know what you think! Leave a comment, register for erotica, or catch a webinar.

More Articles

Ruby Ryder shares stainless steel chastity cage with lock for chastity play

It’s Good to be Clean

Masturbation Month 2024 #29 (Link to Part One) Cleaning day! What the actual fuck, thought Frank. Sure, he could see the point behind it, and honestly

Read More »
Sportsheets Thigh Harness offers the best kind of railing

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

Read More »
Anal training cone pops right up

Podcast #303 Pops Right Up!

Pegging Paradise Podcast #303 Just when you wondered if you’d lost me… Another podcast pops right up! Information/Articles Equipment I hope you enjoy this podcast.

Read More »