99 Days

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Tom Allen
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99 Days

Post by Tom Allen » Tue Sep 28, 2010 2:57 pm

“How long has it been since you’ve come?”

We both knew very well how long it had been. “99 days,” I responded, thickly, straining against the bonds holding my arms to the headboard.

She knelt between my legs, the lube glistening on her fingers in the candlelight. She worked it into my ass while she spoke. “Ninety-nine days and twenty two hours. Almost done, aren’t we? Tomorrow will be one hundred days. You must be very, very excited by now.” She teased my cock and balls until I groaned an agreement. “And I promised you that if you could hold out for a hundred days, then I’d let you have your way with me for a month straight – any way you wanted, didn’t I?”

“Yes,” I whispered, “just a couple more hours to go.”

It was a good game, but with a terrible penalty: if I came without permission, then I would have to start over for another hundred days. Paradoxically, it got easier as time went on; I was able to allow my focus on my body go elsewhere. Most of the time, anyway; but in the last few days I’ve felt my composure slipping as the deadline neared.

“Do you know what this is?” She held up a black rubbery device and poured some more lube over it. “It’s a butt plug,” she went on, “I read your blog and you wrote that it was something you wanted to try.” I sucked in my breath as she eased the plug into my ass. “I ordered it a couple of weeks ago. It’s quite the toy.” I felt the cool taper stretching me, and then the sudden clenching as my muscle clamped onto the smaller diameter. I closed my eyes, panting slightly.

“And do you know what this is?” she asked again. I opened my eyes to see her holding a rubber squeeze bulb. “See, it’s an inflatable butt plug.” As I opened my mouth to answer, she gave it a squeeze and said “One.”

I gritted my jaw. She paused for ten seconds or so, watching me carefully.

“Two,” she counted, giving the bulb another squeeze.

Another pause. Ten seconds.


The sudden expansion made me twitch.


I started clenching my muscles, knowing that the plug was expanding deeper inside of me.


By now I could really feel it stretching my insides. I rocked my hips on the bed, but that only served to make it stimulate me.


Involuntarily, I let out a whimper.

“Oh, do you like that? It must feel really nice, being all full. I’m sure it’s pressing up against your prostate.”

I nodded. Every movement seemed to excite me, and I could feel my composure slipping.


I let out a small moan.

“Yeah, nudging up against your prostate, all swollen from not coming for ninety-nine days. Look, your cock is all swollen. Must be getting hard to hold back, huh?”

I shook my head back and forth. “No, I’m fine,” I lied. My voice sounded high and weak.

“Sure you are,” she replied. She held up the bulb. “Eight.”

I could feel my arms trembling. I tried to breathe through my mouth, slow, measured…


I bit down hard on my lip. It was filling me, both painful and pleasurable. Each motion nudged me just a teeny bit closer to losing control.

“Wouldn’t it be a real bitch if you came now, with only an hour and a half to go? All that time, only to have to start over again?” She smirked at me.

I tried not to move. When I looked down, I saw the fluid seeping from my cock, dripping onto my stomach. She followed my gaze, and arched an eyebrow. She reached down and gave a slow stroke along the length. I tried to move my hips away, only to make the plug nudge my sensitive spot deep inside. Oh no, I thought. I could start to feel some involuntary contractions.


I let out a long, low moan and writhed on the bed. “No, no, no, no, no!” I begged. “That’s not fair!”

“Would you like me to stop pumping?”

I nodded. “Yes, please, please, please. No more, I can’t take any more, it’s gonna split me open” I babbled. Every time I clenched my muscles to hold back, the plug nudged me a little more. I was on the edge of coming, and maddeningly without touching my swollen cock.

“I think that I’m going to leave you like this for a little while.”

I looked up at her, pleading.

“But don’t worry, I’m not going to pump any more, okay?”

I nodded, relaxing my tense body just a bit.

“Because it would be a real shame if you came now, with only,” she looked at the clock, “an hour or so to go, wouldn’t it?”

“Yes,” I whispered, “thank you.”

I closed my eyes and tried to focus. Breathe in. Hold. Yes, that’s it. Breathe out. The contractions stopped. Breathe in. Hold. I was winning! Breathe out. I was regaining my control. Breathe in…

“Do you know what this is?”

I opened my eyes. She was holding an electronic control in her hand.

“Did I mention that it’s a vibrating, inflatable butt plug?” She looked at me with mock sweetness, “I just put in fresh batteries. Let’s see if they’ll last for an hour.”

More of my ridiculous attempts at erotica can be found on my Stories page.
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Re: 99 Days

Post by dunno112 » Tue Sep 28, 2010 5:23 pm

Lovely story. Thanks!
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Re: 99 Days

Post by keyhldr » Wed Sep 29, 2010 11:12 pm

Excellent story Tom - thanks!!
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Re: 99 Days

Post by neranden » Thu Sep 30, 2010 7:31 pm

*bites lip* That is hot.
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Re: 99 Days

Post by Sir Chaste » Wed May 30, 2012 6:59 am

Wow! A great story, Tom!
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Previously wore CB6000s, Jail House, and MM Jail Bird. Currently wearing My-Steel Total System hip belt.

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Re: 99 Days

Post by LockedByBD » Mon Apr 09, 2018 9:26 pm

How cruel, how wicked, how funny!
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No means no, as in "I have no plans to unlock you." :o

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