Milking/Forced Orgasm Dice Dare for Boys: Slick, Warm Lust Cocoon

[WolfpupNX]

First off, this dare is partially (and that part heavily) based on a brilliant (but very involved, time consuming, and messy) dare by codesunflower, where the idea of plastic sheeting and baby oil and the pillow/blanket fort came from - I want to give credit where credit is due as I absolutely LOVED this idea! That said, the rest of the tease was past my personal limits, so I decided to make my own quite different dice version. =)

This dare involves cum control/multiple orgasms/ruined orgasms, oil/lube, toys (most optional), water, ice, piss (optional), alcohol (optional), and a decent chunk of time available. I've designed this to be FUN, so if anything is in your hard limits (for example, piss play), you MAY reroll until you get something you're comfortable with or skip that specific section; please note this is NOT permission to cheat, and deep down you'll know the difference.

You'll need a few items for this dare:
- some time, likely at least a few hours, for the dare itself and cleanup after
- heavy plastic sheeting, enough to cover the bed twice
- pillows and blankets, the more the better, in order to make a humpable fort so the bed is "interesting"
- baby oil (recommended), silicone lube (careful; this doesn't clean up easily!), or some other extremely slick and long lasting slippery stuff
- various sex toys (but if you don't have them, skip or reroll)

You're going to want to strip your bed at least to the mattress pad and fitted sheet. Now arrange pillows/blankets around the bed, building or body pillow or fort-like structure that would be comfortable to lay with and basically hump, but also relax into (sometimes less is more - you don't have to go overboard - one variation I may use is a body pillow + 2 or 3 smaller pillows). Once that's done, apply the first sheet of plastic, with enough slack that you can tuck it in so it doesn't move. You should end up with a plastic covered pillow fort that's snug to the nooks/crannies. Liberally apply baby oil all over the center of this (being aware of your floor and cautious should any spillage occur). Then lay another plastic sheet over the first one, and optionally your comforter over that (though I'm just going to make my room warm and use only the plastic cover sheet).

A few rules. You will oil up liberally before climbing into your slick, warm sex lair. You should turn on the heat to make the room as warm as possible (within reason; it'd be nice if you could get a bit sweaty under there, but don't pass out). Put on some sexual music, porn, whatever sets the mood for you. You may NOT touch your genitals with your hands unless otherwise instructed. You may ONLY hump your pillow/blanket fort and use your toys for pleasure. Unless it's an emergency (obviously use common sense), you may not leave your pleasure cocoon until the dare is finished. You may take your time and rest as much as needed between cums/edges. If you do not own a certain toy OR if a roll/instruction breaks one of your limits, you MAY reroll/skip; the aim of this is fun and accessibility despite the somewhat high starting requirements, so feel free to adapt the rules to your play style; just try not to cheat (you know who you are)!

Now, it's time for the dice to determine your fate. You're going to be rolling a six-sided dice for each of these categories:

Number of Edges Before First Cum:
1. Two Edges
2. Four Edges
3. Six Edges
4. Eight Edges
5. Ten Edges
6. Twelve Edges

Number of Cums Required to Finish Dare:
1. One
2. Two
3. Three, but ruin your first.
4. Four, but ruin your first two. If you'd like, you can change this roll to Three by rerolling and doing an ADDITIONAL Toy roll.
5. Five, but ruin your first three. If you'd like, you can change this roll to a roll of Three by rerolling and doing an ADDITIONAL Toy roll AND an ADDITIONAL Humiliation roll.
6. Six, but ruin your first three. If you'd like, you can change this roll to Three by rerolling another Edges roll (added to your first number of edges) AND doing an ADDITIONAL Toys roll AND an ADDITIONAL Humiliation Roll.

Toys:
1. Cockring (occasional breaks allowed between cums; these shouldn't be worn extremely long-term; use common sense)
2. Butt plug OR Prostate toy (stationary or vibrating/rotary; whatever you have available or want to use)
3. Pair of panties OR sexy underwear you'll be wearing/humping/cumming through the whole time
4. Vibrating toy (owner's choice - anal, penile, whatever turns you on; just be sure the oil won't destroy it; if you're worried it will, reroll)
5. Nipple Clamps/Clothespins OR Icy Hot/Tiger Balm on nipples (if using clamps or clothespins, breaks between cums are allowed if necessary)
6. Ice cubes (at least a medium bowl's worth) placed around the sex fort that you're sure to feel while humping

Preparation (optional for those not into piss play; if you choose to use alcohol, don't go overboard, but it could be fun to have a nice buzz going):
1. None needed; you may drink water or alcohol as you wish, however.
2. Drink ONE *large* glass of water or alcoholic beverage at least 15 minutes before starting the dare. If you have to pee, either hold it, or go ahead, let it go, and piss the bed, but no cleaning up until the dare's over!
3. Drink TWO *large* glasses of water OR alcoholic beverage at least 15 minutes before starting the dare. If you have to pee, either hold it, or go ahead, let it go, and piss the bed, but no cleaning up until the dare's over!
4. Drink TWO *large* glasses of water AND TWO other beverages (either alcoholic or fruit juice, milk, soda...whatever) at least 15 minutes before starting the dare. If you have to pee, either hold it, or go ahead, let it go, and piss the bed, but no cleaning up until the dare's over!
5. RIGHT NOW, piss in a glass, emptying your bladder, and drink it down (whether it's tiny or large), then wait 15 minutes to start the dare. If you have to pee during the dare, either hold it, or go ahead, let it go, and piss the bed, but no cleaning up until the dare's over!
6. Drink whatever beverages (alcoholic or non) you wish and wait until you really, REALLY have to pee. Then piss in glasses until you're empty (use more than one if necessary), and drink it all down. Wait 15 minutes before starting the dare. If you have to pee, either hold it, or go ahead, let it go, and piss the bed, but no cleaning up until the dare's over!

Humiliation:
1. For every full orgasm, you may not take a break from humping for a full two minutes (slowly count to 120), no matter how intense it feels. Whimper and let me hear how sensitive you are and how you don't think you can take it.
2. For every edge, ruined orgasm, or cum, you must be worshipping/licking either armpit while doing the deed and crying out how fucking horny licking your pit makes you. Hopefully by the end you'll be nice and sweaty and getting a nice slutboy flavor/aroma.
3. For every edge, ruined orgasm, or cum, you must be spanking your ass and exclaiming what a naughty boy you are to deserve to be humiliated and milked like this.
4. Anytime in between every edge, ruined orgasm, or cum, you must reach down and slowly tickle your baby-oil-slick cock and balls for a full two minutes (slow 120 count) while you whimper about how much of a ticklish horny little slutboy you are.
5. If you have any sort of anal toy in your ass, in between every edge, ruined orgasm, or cum, you must reach down and slowly fuck yourself with it for two minutes (slow 120 count). If you're not using an anal toy, either fuck yourself with your fingers OR just tease the perenium with your fingers, your choice.
6. Anytime in between every edge, ruined orgasm, or cum, you must polish your cockhead with the palm of your hand (circular motion with constant contact with your glans/cockhead) for two minutes (slow 120 count), declaring what a cumslut you are.

Once you have your rolls, do any preparation and get any toys ready, oil your body up liberally and climb in your pre-oiled lust cave, spreading the oil all over you and the sheets, getting slick and warm and horny at the feeling! Start your edges and go from there! Be safe, have fun, and hopefully by the end of this, you'll be, sweaty, exhausted, fucked silly, and completely drained of cum! Let me know how you did! Try your best; if you feel you've failed, however, I'm open to doling out punishments!

I haven't tried this myself yet but hope to soon and will post results. Obviously, be mindful of slick conditions after the dare (ie. linoleum and showering), alcohol limits, and the floor around your bed. =) Have fun!

[FemmeAlice]

I love the idea of this ^~^ I'll be sure to try it out some time~

[WolfpupNX]

FemmeAlice, glad you find it hot! Please do share your experience if you try it! =)

[WolfpupNX]

So, in anticipation of this dare, I went ahead and did my rolls. I got the following:

Number of Edges: 2; Four Edges
Whew - that I can handle!

Number of Cums Required: 2; Two Cums
Mmf...hot and doable!

Toys: 5; Tiger Balm on Nipples
A little scared of this one, but I think it will work better longer term than clamps/clothespins! Still, I've never tried tiger balm on my nipples before and am a bit nervous, because there will be no relief if it really hurts. Still, I'm excited!

Preparation: 6; Drinking lots, waiting til I really, really have to pee, emptying my bladder in a couple of glasses, drinking it all down, waiting 15 minutes, and then doing the dare. Piss turns me on, but this should still be challenging...I may have to wet the bed...

Humiliation: 5; Finger fucking or perineum rubbing for two minutes in between each edge/ruined orgasm/cum. I'm going to save the decision until the tease (or maybe do a bit of both), but let's be honest...I'll probably be so horny I'll fingerfuck myself...

I *hope* to get a chance to do this tonight, but I have a ton I still need to do and it'll depend on how tired I am. If I can't fit it in tonight, I should be able to do this tomorrow night.

I'll report my results (and take punishments if I fail anything).

Also, assuming this works well, along with hopefully hearing experiences from other people who try this, from this point forward, if anyone requests me to, I'll reroll and do this again for *each* request I receive. =) So you could make me keep doing this and posting results many times (though it'll have to be as I get time as I won't be able to every day...probably at least a couple times a week, if the requests roll in, but I'll queue them up and do each one eventually).

I want to hear all of your experiences too if you try it!

[WolfpupNX]

Slightly sad news - the plastic sheeting I got isn't wide enough (I must have clicked the wrong one), so I need to get some more before I can do this and not make an uncleanable mess. =/

The good news is I figured out I can put the too small stuff on the floors to protect them in case there's any "spillage" (especially with the piss play).

More good news is I tried humping just a little baby oil on the plastic material over a single pillow, and it felt *wonderful*, so I just know this is gonna be fun. ^.^ (Also, baby oil washes off easily, I found out.)

Hoping I can get my hands on the right plastic Tuesday, so stay tuned, and I'll do the dare (with the rolls I got earlier) then! It's still fair game to order me to do this dare again for you for whoever wants to; they'll just pile up and I'll have to do them in the order received. =)

In the meantime, now I'm super horny so need to find other ways to cum for tonight! =oP

[WolfpupNX]

*UPDATE* - completed successfully; here's my experience (and it was very enjoyable I must say)! Now who's brave enough to join me, eh!?!?

I was super horny and decided to drop by the local Lowes store to see what kind of plastic they had. It's in the paint section marketed as drop cloths. They have some that are close to a perfect size (10' x 12') in various thicknesses, and then bigger/thicker ones as well you could cut to fit. So I got some (oh and it's fairly cheap) and was excited to do my dare tonight!

Getting the bed made up earlier in the day wasn't too bad. I put a large body pillow in the center, and three neck support countoured pillows (with dips) around it (I could probably get away with just 1 next time as I didn't really use the others much, and I'd probably also move the whole thing to the side of the bed I'm on a bit as it moves a little in the other direction over time...I mostly stayed in my spot near the pillow I was humping). You want to make sure any plastic sheeting isn't too tight so there's some play and it conforms to the pillows.

I cranked the heat up (as I wanted to be warm and sweat...I had also exercised a few hours earlier and not cleaned up after).

I drank my liquids and watched TV - 2 large glasses of water, a glass of wine, a cup of tea, and a good bit of vegetable juice (with celery - gotta replenish that cum!). After about an hour and a half, I had to pee badly! I filled up 3 large glasses and a little more (it's amazing how much a bladder can hold)! Downed it all like a good boy, and waited my fifteen minutes.

I had porn and sexual music playing and after squirting baby oil all over the sheet and oiling up myself, as well as applying the tiger balm to my nipples both before and after the oil (and just a smidge to my balls since I was curious), I climbed in bed on top of the bottom sheet of plastic/pillows and under the plastic sheet. I'm glad I didn't do the comforter as just the plastic sheet on top was amazing!

The slickness and slipperiness was really fun and felt unlike most things I've felt before. As I humped away at the plastic covered pillow for my first edge, it felt amazing and I knew I was going to like this...it was super hard to stop though; I wanted to cum badly as I was turned on thinking about it all day!

In between I fingerfucked my ass like a good boy - this was fun but not the best part - I hope for a toy next time if I'm fucking as fingers just don't have enough leverage. It was neat to feel how slick my ass cheeks were with the oil though.

The only disappointment is I really didn't feel much as far as the tiger balm on my nipples. I applied a good bit both before and after the baby oil, so I'm not sure if the baby oil might have somehow neutralized it or what. I did feel it a little on my balls, so I know the stuff works, and I've used it for shoulder pain before and it's quite intense - I'm really surprised I didn't feel it in my nips more. Next time I might try icy hot (which is harder core I believe) or some kind of clamp.

As I hit my edges and fucked myself in between, I felt myself getting both slick and sticky and knew I was sweating a good bit...when I was fucking the pillows, I made sure that top sheet (which was thinner than the bottom - I had tried thin for bottom too, but it ripped to easily) was covering my whole back (from the shoulders) and butt, and feeling it cling to my sweaty body was a real turnon. I might try using a thick one next time to see how that feels.

I will say the sheets did move some towards the end, but it wasn't too bad to fix them when they did. I was very lucky as my edges/number of cums were low enough that even though I probably got the worst pee portion of the dare (again, optional) I didn't end up having to pee (I was getting somewhat close near the end but not desperate). If I did need to pee, honestly, I'd probably be doing bedding right now, but that's the punishment if you can't hold it I guess. I do recommend checking the sheet positions before pissing if you have to! (But I think I made the criteria easy enough that unless you're *very* unlucky, you can probably avoid it.)

Finally, the orgasms were FANTASTIC! I do pity the poor boy who gets the continue humping for two minutes after cumming roll. I tried to do this as an experiment and didn't follow through because it was just too sensitive (but fortunately I didn't have to this time as a criteria for success)... That kind of overstimulation might even cause me to pee if my bladder was full. I guess if I ever get that roll, I'll find out.

I was able to cum a second time pretty quickly...I'd say within 5 or 6 minutes... By then, I was very hot and sweaty but feeling great, though tired. The top sheet was literally all wrapped around me and even torn in a few places.

Cleanup was quite easy (though it would have been a different story had I pissed). I just got up on a towel I'd put down (in case the bottom of my feet were oily, which they were a little bit), got a large trash bag, and carefully (folding up by the edges) put all the plastic in it. Hardly any oil on the bed (tiny bit on the side I wasn't - not sure how that happened), but I was able to just make the bed as usual. =)

So in summary, this was really hot! I would LOVE to hear other people's experiences, and feel free to dare me to do this again (and again)! Hope you found my experience enjoyable to read!

[FemmeAlice]

Thanks for the reply! I'm even more tempted to try this now! I can't wait...!

[MALEficent]

I plan on doing this when/if I finish all my edges

[WolfpupNX]

@FemmeAlice, so glad you enjoyed reading about my experience! Can't wait to hear yours when you do it! (And if you want another experience report, feel free to dare me to do this again!)

@MALEficent, good luck on finishing your edges, and hope you enjoy the dare - would love to hear about it if you end up doing it!

[codesunflower]

Nice adaption of my original dare; I like it

[WolfpupNX]

Originally Posted by codesunflower

Nice adaption of my original dare; I like it

I'm so glad you approve! I thought your idea was absolutely amazing, so thank you for thinking it up; it's only because of you this adaptation was possible in the first place! =)

[Sissyboy998]

I really want to do this, but I’m having a hard time visualizing the layers of the bed. Someone please help me. Thank you.