Now This is How You Request a Dare - Orgasm Challenge
DigitalKat issued me this dare/challenge, but as a poem!
I remember reading somewhere
You cum just a couple times a week.
That number feels really low to me
Unless my drive makes me a freak.
That's why "four" has been given to you
As a dare in which you'll complete.
Writing your stories of how and when ...
Will be an extra little treat.
But we have unfinished business
You have an outstanding dare from me.
A frontal wedgie for three hours
Tugging hard occasionally.
I'll increase the hours to four
If you don't start Immediately.
Don't sit on this dare too long
Else you'll receive the wrath of me.
I've never been much into masturbation challenges, since most guys don't get how women pleasure themselves (that will be a blog article one of these days). On the average, since the divorce, as the poem states, I pleasure myself about twice a week, usually less, but occasionally more. Most of the time it isn't to a full orgasm. So this is going to be a challenge for me to have four full self-inflicted orgasms within a week.
What makes this dare so sexy, however, isn't that it is simply commanding me to masturbate, but the challenge came (ha, unintentional pun!) as a poem, which is so sexy.
I will report back in the comments on my attempts to fulfill this lyrical request.
I remember reading somewhere
You cum just a couple times a week.
That number feels really low to me
Unless my drive makes me a freak.
That's why "four" has been given to you
As a dare in which you'll complete.
Writing your stories of how and when ...
Will be an extra little treat.
But we have unfinished business
You have an outstanding dare from me.
A frontal wedgie for three hours
Tugging hard occasionally.
I'll increase the hours to four
If you don't start Immediately.
Don't sit on this dare too long
Else you'll receive the wrath of me.
I've never been much into masturbation challenges, since most guys don't get how women pleasure themselves (that will be a blog article one of these days). On the average, since the divorce, as the poem states, I pleasure myself about twice a week, usually less, but occasionally more. Most of the time it isn't to a full orgasm. So this is going to be a challenge for me to have four full self-inflicted orgasms within a week.
What makes this dare so sexy, however, isn't that it is simply commanding me to masturbate, but the challenge came (ha, unintentional pun!) as a poem, which is so sexy.
I will report back in the comments on my attempts to fulfill this lyrical request.
Total Comments 31
Comments
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First Attempt – Day #1
I've never masturbated before with the sole intent of achieving an orgasm. As I have said in other reports, I have been masturbating more frequently since the divorce, but having a full orgasm happens rarely. Since this dare requires me to “cum” it means more than simply playing with myself to relieve stress.
I thought about this challenge throughout the day, which made me feel a bit naughty, which helped me get in the mood. Originally, I thought of taking one of my special bubble baths, but when the time when I was free in the early evening I was already a bit horny.
I stripped down to an old pair of cotton panties and the tank-top t-shirt I wore on my last dare. There not sexy to look at, but I love the feel of soft cotton against my skin, even more so than silk. Sitting on my bed against my husband (i.e. the portal chair back shaped bean bag) I place my laptop on a pillow on my lap and I started to read and write getDare material.
I read a few posts, worked on some blog articles and stories as I slowly became more aroused. When I read over the material for a story I am working on I began to gently cup my breasts. As the writing became more salacious my proof reading time went from mere touching to full fondling, as I massaged my breasts and gently pinched at my very erect nipples.
My thoughts and then my words wondered over to my “sister's” new concept of having a harem. I thought of the cover picture I found and what it would be like to be a dominate woman having three gorgeous male gladiatorial slaves chained up for her pleasure.
I realized that my fantasizes this time, however, were not for myself, but that I would have to publish them. I felt shame at having such pornographic thoughts for this wasn't the normal things I would think about when I pleasure myself. I tried to put my more common vanilla thoughts back into mind about romance and tender love, but it was too late.
Pushing the husband off the bed I bunched up the pillow and mounted it in between my legs as I laid on the bed so I could type. As increasingly lewd images danced through my head I humped and grinded away on the pillow pushing myself to the goal. My perverted fantasies went from me being my sister having her way with those gorgeous muscular slaves, to me being just Amy, a slave myself thrown to the gladiators for their pleasure.
Losing all decorum I slid the laptop away and rolled over on the pillow, forcing my back to arch up as my hands ravaged my body. One hand furiously rubbing away on my aching sex and the other hand molesting my breasts, spanking them occasionally for being such a bad girl. I saw the massive and ripped gladiators glare at me, their eyes full of rage for being so mistreated by my sister as they took out their anger and lust on my defenseless body, ravaging me before a cheering crowd. I literally cried out, “no, not like this” having a sweet and horrible double meaning. As the fantasy slave to the crowd vainly hoping for mercy from my attackers, while at the same time realizing I will have to share this with the community, ashamed that everyone will think this is how I normally masturbate.
“It's normally not like this” I whimpered as my body quivered into a full, sustained, orgasm, lasting a few minutes.
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I have to confess, this was one of my more intense orgasms I have had in a while. I feel quite dirty. At the very least I was successful on my first attempt during my first day. One down, three to go and I have six days. I usually go several days before masturbating again after achieving such a full orgasm, but I will be back at it tomorrow, trying to go for two in a row.Posted 04-08-2017 at 03:14 PM by cariadferch 
Updated 04-08-2017 at 07:21 PM by cariadferch -
Amazing read! I truly feel honored that you are enjoying the dare!Posted 04-08-2017 at 04:58 PM by DigitalKat
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Second Attempt - Day #2
This morning I got up early to go for a morning run, one of my favorite things to do on a Sunday morning. While in the shower I started to play with myself, which, beside the bed, is the most common place I masturbate.
I love the feel of the pulsating caress of the warm streams of water as a I sway back and forth while hands roam across my body. My mind doesn't usually create a story per say (like the night before) but more streams of emotions. I feel like an elegant dancer in a grand ballroom wearing a beautiful Nicole Miller dress or a salsa dancer slowly shaking her thing in some island club.
Sometimes I turn on music to go with my private little dance. At first I didn't, but when I realized I had stopped and I hadn't orgasmed (I usually don't orgasm when I masturbate like this), I flipped my phone from the news to some sweet jazz and continued the dance for a few more minutes. It was fun to "dance" to the music for a bit, but in the end it didn't work, as the mood slipped away, so I gave up.
My record is now 1 for 2, but I still have six days and probably will try to take another crack at it tonight.
Hwyl am rwan (Bye for now)Posted 04-09-2017 at 03:45 AM by cariadferch
Updated 04-09-2017 at 03:54 AM by cariadferch -
Even your attempts are beautiful to read!
Posted 04-09-2017 at 04:32 AM by DigitalKat
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Third Attempt - Day #2
So, I had a full and fun day. Went for a nice long leisurely run this morning, the weather was just beautiful. It is really starting to feel like spring. I can't wait for beach weather! After some shopping this afternoon I went out on a causal date this evening, just dinner at an Italian restaurant. I'm still not sure I want to get into any serious relationship, but the company and the food was very pleasant.
Back at home I was still in a good mood, the wine certainly helped, and I remembered my ongoing wager. Stripping naked I put on my silk bathrobe and laid on my bed. I tenderly caressed myself through the bathrobe, slowly opening more and more of it up as I imaged an impeccably dressed fantasy date gently stripping me and himself as he prepared to take me. With my robe full open, my legs spread, I fantasized about him stripped down to but a clean crisp oxford shirt, wide open, exposing his magnificent body as he lowered himself onto me. I squeezed down on my breasts, pretending it was his muscular chest flattening mine as I slide a finger towards my sex, moaning in anticipation, imaging he was preparing to mount me.
Then the phone rang.
It was my hypochondriac elderly step-aunt.
We talked for over 45 minutes.
Needless to say it was a buzz kill.
I didn't even bother to try and finish pleasuring myself. So afterwards I caught up on my social media and I plan to go to bed.
1 for 3 thus far, with 5 days to go to get to 4.Posted 04-09-2017 at 08:08 PM by cariadferch
Updated 04-09-2017 at 08:10 PM by cariadferch -
Day #3
Briefly thought about masturbating in the shower this morning, but woke up hard, allergies and what not, so it wasn't going to happen. Off to serve the man (i.e. work).Posted 04-10-2017 at 03:46 AM by cariadferch
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Day #4 (Tuesday)
As I feared, the early and mid parts of the week gets busy for me, and I am falling behind. I got in late last night and though it was an okay day, I was too tired for any night time calisthenics. It's early Tuesday morning and I'm not really in the mood either. I did realize that I have never had an orgasm (at least a self inflicted one ) in the shower before. I might make that an additional goal for this week.
Well, off to post on my other social media and then work. Tuesdays and Wednesdays are my late days, so this is getting to be a real challenge. I need to have 3 orgasms before the end of the day of Friday or I fail this dare.Posted 04-11-2017 at 02:48 AM by cariadferch
Updated 04-11-2017 at 02:51 AM by cariadferch -
As a reader, sometimes the struggle is hotter than the accomplishment!
Posted 04-11-2017 at 03:32 AM by DigitalKat
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Pervert!Quote:Originally Posted by DigitalKat
As a reader, sometimes the struggle is hotter than the accomplishment!
I'm just trying to be honest, it makes it more fun.Posted 04-11-2017 at 03:39 AM by cariadferch
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Day #4 (Tuesday) – Fourth Attempt
Okay, so I got home late tonight, which is my usual for Wednesday night and I wasn't really in a sensual mood. Again, not a bad day, but didn't feel the need to masturbate. However, I have to cum three times by Friday, so I realized I really needed to give it a go tonight. I've never tried to have an orgasm solely for the reason of having one, so it became an interesting experiment.
I'm not much into toys, but I do have two vibrators that I use on occasion. A new “egg” design I bought early this year and my good old trust wand vibrator. Stripping down to but a lace bra I laid on my bed and took my old friend to myself. I first it felt kind of awkward not being that much in the mood while hearing the fairly loud whine of the ball head massaging my private parts. I toyed (hmm, bad pun) with giving up, but I hate to lose.
Closing my eyes I let my mind wander, cycling through various scenes and emotions that might turn me on. It took me a while but I hit on a rather mundane schoolgirl trope. Basically being white knighted by some gorgeous guy. (Look, I'm a traditional girl, I want the guy to be the guy.) After being saved from some random bad guys, my hero, who strangely looked a lot like Chris Evans (damn he is so hot), escorted me back to my house. I felt honored bound to give him my thanks for his efforts. As a gentleman, he at first, of course, refused payment and even my advances. But after asking his advice whether some of my bruises need medical attention, which of course required me to remove of some of my clothing, we ended up in my bedroom with all our clothes off.
At first I fantasized about his tongue skillfully probed my inner most regions, while my old friend was slowly bringing me closer to the goal. But then I remembered this fantasy was not for me alone, but to be consumed by the public. That dirty little thought pushed me further.
I began to image what my audience would want to hear. Yes, I prefer to receive, but I know what guys like. My thoughts now had me on my knees before my hero. His hand firmly grasping my hair, forcing my willing mouth to his erect cock. There was no doubt want he wanted as payment and I was honor bound to service his every need.
I saw his manhood twitch as my wanting warm breath gasped against the naked flesh of his most private part as I was brought near. I loved hearing him hold back as slight moan as I began to kiss his shaft, at first with small caressing touches and building up to my mouth hungrily ravishing up and down is pulsating weapon.
I went to grab his manhood, to masturbate him with my hands, but he would have none of it. Calmly, pushing my hand aside, he pressed the tip of his cock against my mouth, making his demands clear. Looking up at his eyes, he glared down at me with animistic lust as his grip on my hair tightened as he forced his shaft into my mouth.
Sucking cock isn't my favorite thing, but I have done a lot of it, since my ex loved it so. But for my hero, I would do anything to please him. As my head bobbed back and forth with ever greater rhythm, I took more and more of him down my throat. My mind, however, turned to all those who might be reading this blog, and the thought that they might be masturbating to my words made my ego swell.
And then I came, my groans drowning out the vibrator noise.
Well, that is my second orgasm. I need two more in the three days.Posted 04-11-2017 at 08:56 PM by cariadferch
Updated 04-11-2017 at 09:03 PM by cariadferch -
Wow, for the best erotic reads, subscribe to Cariadferch's blog. Wholly Hell that's hot!
Posted 04-12-2017 at 03:36 AM by DigitalKat
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Super excited for your next attempt!!
Posted 04-13-2017 at 01:23 PM by DigitalKat
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Well I played with the tiger and got bit.
I have to concede defeat.
Wednesday, Thursday and especially today have been crazy, so I won't have the time, or inclination, to begin that day's race, let alone "finish" the course, if you know what I mean.
As per our arranged I now owe Digi the following . . .
* Sometime soon will masturbate by humping a pile of pillows, with my ass high in the air, to a full orgasm, while reporting it live here on my blog.
* Another dare owed of his choice to be called in whenever he wishes.
* Some form of punishment to be decided by him in the next few days.Posted 04-14-2017 at 02:49 PM by cariadferch
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Ah, the bitter sweet sounds of a defeat.
Posted 04-15-2017 at 07:38 PM by DigitalKat
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Took you long enough to decide my punishment. Cat playing with the prey, huh?Quote:Originally Posted by DigitalKat
Ah, the bitter sweet sounds of a defeat.
Okay, so in the next week I have to . . .
* Flip a coin and determine if I get a frontal or rear wedgie and then go for a run. Stopping several times to make sure it stays in place. (I don't get this wedgie fetish at all.)
* At the end of the run I'm to take 100 on my rear with a home made switch (i.e. a thin green tree branch).
* Once I have spanked myself I have to masturbate by humping a pile of pillows, with my ass high in the air, to a full orgasm, while reporting it live here on my blog.
* Also, DigitalKat gets another dare of his choice to be called in whenever he wishes. This dare trumps all other dares. If there is a conflict I have to ask the other person for mercy.Posted 04-15-2017 at 08:41 PM by cariadferch
Updated 04-16-2017 at 03:18 AM by cariadferch -
I'll take as long as I need to determine the proper punishment. There is no need to understand a fetish, just do it!
Posted 04-16-2017 at 03:51 AM by DigitalKat
Updated 04-16-2017 at 04:09 AM by DigitalKat -
Look at the little kitty trying to play as a dom, very cute. Should I get a ball of yarn for you to play with?Quote:Originally Posted by DigitalKat
There is no need to understand a fetish, just do it!Posted 04-17-2017 at 06:54 AM by MistressCariad
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Just do it!
She requires training as her actions of questioning, excuses, and reading too deep into things needs to just be more of a "yes sir" and then do it.Quote:Originally Posted by MistressCariad
Look at the little kitty trying to play as a dom, very cute. Should I get a ball of yarn for you to play with?Posted 04-17-2017 at 09:15 AM by DigitalKat
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Okay, so this is the payment for failing Digi's dare of having to have four orgasms in one week. I'm suppose to do this “live”, i.e. post it in incremental threads as I complete the various punishments required. I have to admit the idea of doing this live with the feeling that others are “watching” me has made me rather aroused all day. I'm also a bit nervous that I have to spank myself with a switch, something I have never done before. (Also, please forgive the lack of proof reading.)
But first, the run. I am suppose to go for a run with a wedgie. The run part, is sexy, not sure about the wedgie part. Since I am suppose to report everything, and this is a punishment, I have decided to go with a bit more daring running outfit then the usual sweatpants, old t-shirt and light jacket.
Working from top down, I am going to wear the tank top t-shirt I wore on my last public dare. It shows a bit of cleavage, again, something I usually don't do. For running I always wear two bras. My usual light gray Nike sportsbra and for this occasion an old lacy, low cut black bra. I like the combination of support and naughtiness. Instead of the baggy sweatpants I am going with my tightest running pants, there not yoga pants, mind you, but tight my conservative standards. Since I have to do the wedgie thing I am wearing well worn white cotton thong. Finally, my running shoes and white socks (I confess I can get sweaty feet, so socks are always required).
Taking a coin, I have to flip it for a frontal or rear wedgie. I really am hoping for tails.
Yes! Tails, rear wedgie. Reaching around I yank up the thong. Its mildly annoying, and kills the sexiness a bit in one way, but does add to the eroticism that this is a punishment.
I plan to do my short run (1.5 miles with hills), be back in twelve to fifteen minutes or so.Posted 04-20-2017 at 02:14 PM by cariadferch
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I'm back.
The wedgie thing slowed me down at first, more of an annoyance then anything else. I got half way through the run and almost for got that I had to pull it up along the way, as part of the payment. I hate stopping when I run so I tried to do it discretely when moving, pretending I was fixing the back of the my shirt.
Fortunately, I didn't pass anyone while on the jog, save the neighbors' dogs and a few passing cars. I did feel like a bit of slut, running with my cleavage showing, making my breasts feel larger. It is a beautiful day for a run, however, which is always sexy.
Once back on my property I ripped off a three foot thin tree branch from one of my trees so that I can whip my ass with it a 100 times. I am rather nervous about this since I have only spanked myself with my hand, ping pong paddle and spoon. The spoon hurt a lot more then I thought and I am scared this will too.
Well I have to strip and make my bed . . .Posted 04-20-2017 at 02:28 PM by cariadferch
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Okay, I have stripped everything off of my bed save a pile of three piles. I am suppose to hump my way to an orgasm with “my ass high in the air.” The bottom pillow is a firm foam one, the middle is a large feather pillow and the top one is a old feather pillow that is rather dense because of age. I have made this into a ball to fit in between my legs. I have place my laptop at the top of the bed so I can write while I masturbate.
I have stripped down to but by thong. Looking at my “lover” and the switch I fondle my breasts to get more into the mood. Reaching back around give my thong as strong as a yank as I can. I grimace a bit at the slight pain and that my ass will be completely uncovered for the switch.
I mount my lover.Posted 04-20-2017 at 02:33 PM by cariadferch
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I am in position, on my stomach, my hands above me so I can type and my ass high in the air with my legs spread. I am slightly humping away on the pillows as I type this. Damn, I feel like such a whore. I image dozens of guys masturbating to my posts (I know, probably no one is reading this, but my imagination is quite worked up) while I masturbating at the same time as if it is some internet orgy and I am the prostitute.
I just took a break from typing to fondle my breasts. My nipples are rock hard. I hate typing with one hand, so there will be pauses. I will have no problem having an orgasm like this. The small pillow fits perfectly.
But first I have to take the whip.
I'm going to give myself 10 and report back.Posted 04-20-2017 at 02:37 PM by cariadferch
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Okay, that stung. Not as bad as the spoon, but worse than the paddle. I'm glad I didn't feel the knots in the branch, which was a concern.
I'm humping with every swat, fuck, why is spanking such a turn on for me? I'm such a whore.
Going to do another 40.Posted 04-20-2017 at 02:40 PM by cariadferch
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awww, my ass is really sore.
i again wavering with the force half way thru and had to will to pick up the pace.
on godo thing is the switch is so thin i can stirke different places,. i'm going around a circle from lower, mid, upper for each cheek – right to left.
with tht pause of from typing this i'm grinding away on the pillow, i want to cum. each swat drives me further into the pillow.
fuck
going to try the last 50Posted 04-20-2017 at 02:45 PM by cariadferch
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the lastl 50 was terrible i slid off the pillows had to remake them
look back at my ass, full fo lines
now i[m humping away on the pillows
tis hard to type
sorry
dam this feel liek the world is watching me
oh fuck
coming
fucmkPosted 04-20-2017 at 02:52 PM by cariadferch
