Another Friday Fantasy (99 days)

Stolen from inspired by Destiny & chance

“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.

About Tom Allen

The Grey Geezer Dauntless defender of, um, something that needed dauntless defending. Dammit, I can't read this script without my glasses. Hey, you kids, get off my damn lawn!
This entry was posted in BDSM, D/s, Erotica, Friday Fantasy, orgasm denial, The Stories. Bookmark the permalink.

13 Responses to Another Friday Fantasy (99 days)

  1. Pingback: Femdom Blogs » 100 Days of Chastity

  2. Sagittaria says:

    Pretty hot stuff. 🙂


  3. Tom Allen says:

    Hi Sagi –

    Did I mention that I’ve looked at those videos about, oh, two or three hundred times by now? Just something about the idea really pushes a button or two for me.


  4. maymay says:

    Wow, Tom, this was an awesome vignette! So am I to understand you write a fantasy such as this once a week? That’s actually a brilliant idea. Mind if I coopt it?


  5. Tom Allen says:

    maymay, I kept that up for about two months, and a few weeks ago I just had too much going on. By all means, feel free to join in – I suspect that you’d be good at this.

    Check my blog categories for Friday Fantasy, that should bring them all up. The last one I did was featured on several sex blog ranking sites, and has a pretty high hit count. The subject matter would probably be of some interest to you.


  6. rlewizr says:

    fantastic. I had to read it a couple of paragraphs at a time as my cage kept getting unbearably tight.


  7. Tom Allen says:

    Imagine how tight my cage was when I wrote it 😉


  8. Anna says:

    This. Story. Drives. Me. Mad.

    There’s something about being driven so close but trying so desperately to hold back.. I don’t know..

    And the worst part is, I’m in my own sort of chastity control – I really feel that sex is something I want to save for marriage, so that when it finally happens it will be all pent up and amazing.

    This story makes me want to throw that all away.. but I’ll just save this idea for my husband… 😉


  9. Excellent! I enjoyed it hugely, as you might say………….


  10. roadrunner says:

    I have read your story more than once, and each time, it makes me drool out of the end of my CB6000. You have described my wife teasing personality perfectly. If only I could get her to do to me what you described…


  11. Pingback: The Edge of Famous | First World BDSM Problems

  12. betlamed says:

    Ha! That was a good one right there! I really enjoyed this, thank you.

    It’s actually a very good idea. I wonder if there are many people who would actually come from this, though. I know butt plugs never got me anywhere close. Granted, I never tried them after 99 days…


  13. roadrunner says:


    One way for the key holder to punish the male who ACCIDENTLY ejaculates without permission, would be to use POT ( post orgasm tease/torment /torture) as a punishment. procedure. This procedure can even be used if the male is made to have an “accident” on purpose, giving an excuse to use this method to emphasize a key holder’s total control.

    Post Orgasm Torture

    ( Part of this article below is from another web site. I have edited it with a little embelishment. If the original article belongs to you, please accept my apology. )

    This is a fun one. To the uninitiated, “post orgasm torture” may summon images of a male being punched in the balls after he’s come, but it isn’t that at all. In actuality, the things done during post orgasm torture would be very pleasurable as pre orgasm. After orgasm a man’s cock become very sensitive. More specifically, what becomes sensitive is the glans, aka the cock head. If you are a women reading this, you’ve probably experienced the feeling with your clit. Touching it directly after orgasm is just too much. Forcing this sensation on someone is post orgasm torture.

    One important thing to know about post orgasm torture is that it causes involuntary motion. Think of being tickled, you can’t help but laugh and squirm. In post orgasm torture these reactions manifest themselves in sudden jerks, flailing, and sometimes even convulsions. While sexy for a key holder to watch, the unrestrained male is quite effective at stopping you from playing, and it can even be dangerous depending on your distance from said limbs.

    I recommend you always securely bind your male to a bed, spread eagled, lying on his back, for maximum access to his cock and balls. Use soft, but inescapable cuffs, with straps restricting his limb movements, beforehand. Although he will now be unable to stop you from erotically teasing and torturing him, he will still become very vocal. He cannot help himself !! If you don’t want to listen to his begging for you to stop, his laughter, screaming, and whining, you should have a mouth gag handy to silence him. An effective gag will allow him to only quietly moan, and muffle his screams, as he tests his bondage straps, trying to escape his torment. Not only does this make the act more “forced,” but it lets you safely go on as long as you’d like without being interrupted. Also, it’s very sexy to see someone straining against their bondage, hoping to be able to break free of their torture, but finding their efforts completely futile. You have him right where you want him, unable to do anything about your taunting and teasing!

    Prolonging the erection is important, as blood will quickly drain from the cock after orgasm, especially during post orgasm torture. Go to work right after orgasm, don’t let the cock sit for any amount of time. The harder the cock, the more full the head is, the more sensation it will feel. Cock rings or cock bondage can slow a falling erection, ( Set that up before orgasm, it will free both hands for maximum teasing. ) but if you prefer, all you really need is to grab the cock shaft near the base, pull the skin tight, and squeeze. This can slow, and sometimes even stop the blood from leaving the erection. If using the second method, I suggest using your non-dominant hand for this, so your dominant hand is free to do the dirty work.

    The ironic part of post orgasm torture is that the more pleasurable an action would normally be before orgasm, the more painful it will be afterwards. Lubrication increases sensation, so a good tip for post orgasm torture is to use lots of lube. Cum will act as a lubricant, but I suggest having a bottle of lube near by and making sure he is well lubed up before orgasm. Secondly, the more constant contact you are making with the glans, the better the reaction you will get. Thirdly, don’t hold back! This is entirely harmless fun. The reactions you get may be over the top and uncontrollable on behalf of your male, but again, compare this to tickling. This is actually one of the safer “torture” acts found in kink.

    The most common method for this is to just stroke up and down quickly over the head of the cock. Squeezing as you go increases contact and sensation. An easier method, and one that also tends to give better results, is palming. It’s pretty simple, close your palm over the flat of the penis head. Run your palm in circles back and forth over the glans, rubbing the tip, the flat, and the rim all at once. If your hand is small enough you can even let your fingertips brush the sensitive spots on the under side of the cock head, but focus your pressure primarily on the flat. You can also do this method in reverse, focusing on the underside of the cock, but for some reason it seems to get less of a reaction. Any hand job technique will work to some degree, and everyone is different. See what makes your male jump the most and repeat that, or try to find new ways to solicit such reactions. Just have fun with it. You could even make a game out of finding what gets the biggest reaction from your male. Since he is secured for your pleasure and attention, it will be easy to determine what he responds to most, by the amount of writhing, squirming and straining at his bonds he performs.

    And while you are at it, don’t forget about his balls. After ejaculation, some males become super sensitive to having their balls scratched with sharp fingernails, or gently, and suddenly touched by your fingers. If using the cock rings or cock bondage method, you can also gently cup his balls in your free hand, and massage them in a rolling motion, as you are busy with the other hand playing with his glans, cock head and his cock crown. The combination of the two different areas being played with simultaneously, should have him going wild, moaning, and working his bondage straps to the hilt!! This action will help make him realize how helpless he really is, and totally at your mercy, of which you should show him none…

    The best thing about post orgasm torture, as I’ve mentioned before, is that what you are doing would normally be extremely pleasurable. This is part of the fetish for those who are into it – forcing someone to endure something that they would normally find enjoyable, and for those on the other side, being forced to endure such things. If you want to play off of this element of the fetish you can tell your male thing such as, “But this is what you like!” Or, “If you don’t like this then why did it make you come?” The “you like this” angle is fun. Depending on the male, you could even use post orgasm torture as a punishment, perhaps for coming too soon, or as part of a game. “I’m going to play with you for X minutes, if you don’t come you lose your orgasm for tonight, but if you do come I won’t stop until the time is up.”

    Believe me, after you have finally worn him out with this procedure, he will remember the experience. He will think twice about the consequences of disobeying you the next time, whether it is truly an accident, or forced to happen on purpose.

    I would like to experience being teased as described in your 99 days story, and then immediately upon cumming, be forced to endure the situation, described in the article above.


Talk to me!

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s