I'm quite experienced in this area, but would love a little challenge ;)

I’d like a dare please, if you are still doing them! I’m somewhat experienced, but haven’t played much lately.
Likes: anal, tease/denial/edging, nipple play, tit play, (very) hidden public (like a butt plug at work), long duration plug wear
Limits: public, scat/piss, enemas, anything permanent or exposing, breath play, sharps/blades
Dislikes: temperature play, overstimulation
Toys: vibrator (bullet-ish), small glass plug, “medium” njoy plug, large silicone plug (little tough to get this one in), anal hook, alligator nipple clamps, screw-up vice nipple clamps, clover clamps, nipple suction cups, ball gag, bit gag, open mouth gag, small dildo, tack bra

I'd like you to drink a lot of water and then wait until your bladder is really full. Don't go to pee, hold it!

Take your smallest toy and lube it up, put it in your butt. Remove it after 5 minutes and put it aside for later. Do this with all your toys, going from smallest to largest.

Take all your used toys and put in a pile them in the bathroom (shower or tub). Pee on them like a dog! Then choose any two of the pissed-on toys and try to put them into your butt at the same time. You may insert one after the other, but they have to be in your butt together at the end.

If you fail, you need to keep your biggest plug inside for at least 4h.

Nice on the Njoy plug, I have the Pure Plug 2.0, it's a good investment ;)

For your dare: Start your day with the biggest plug you can manage to wear continuously. The Njoy if you must, but if you can, go for the large silicone one -- go big or go home! Warm up with a smaller toy if needed.

Go about your day as you would normally (work, school, whatever). Choose a day where you have to leave the house. At one point during your day, go out and buy an insertable object that is slightly larger than your silicone plug. This can be an actual toy, but better if you misappropriate something. A vegetable? A tool? Be creative. You know where this is going, choose something large, but with a reasonable expectation of your butt being able to take it after some instruction.

When you get home, take out your plug and finger yourself with two fingers, one on each hand. How open does it feel? Can you "pull apart" your butthole? Start masturbating and edging at this point, but don't cum!

Lube your plug up again and reinsert it, then take it out fully. Do this 10 times at least. Repeat the fingering. More open? Yes? Reward yourself by starting to wear the ball gag. Continue masturbating, no orgasm.

Now take the object you've bought and lube it up (use a condom if you want). Push it up your butt. It's OK if this takes you a while, don't give up. If you can't manage, use your silicone plug to stretch more. Bite down on that ball gag to give it your all. You're only allowed to cum after inserting the object fully (as far as it will reasonably go) and edging 10 times with it in your butt.

If you cannot manage that, you must wear the silicone plug overnight and may cum in the morning before taking it out.

Hi there, i’m open to try a date. I’m pretty new to anal and exploring. I have a small butt plug, and I’ve tried putting a banana up my ass with debatable success ��. Go easy on me…well, go easy on my ass ��

Let's get your anal journey started, then! Your banana story sounds like you're quite adventurous with your butthole, so let's use that.

Have you had your cum dildo up your ass before? I'd like you to insert your plug and chug 1 L of water. Once you have to go pee, save the pee in a jug or similar. Then remove the plug (do you dare to take it into your mouth?) and insert the cum dildo as deep as it will go without being swallowed.

Assume a position on your back with your ass in the air (knees near your face).

Now take the stored pee, and "cum" it into your asshole. Bonus points if you're keeping the plug in your mouth during!

Once all the pee is in your butt, comes the critical moment. Remove the dildo, but without spilling any pee. Keep your butt high in the air. Be very quick, once the dildo is out, put in the butt plug to plug your hole.

See how long you can keep the pee enema in your butt. Can you do one hour? Can you cum with the pee still in your butt?

Please send me dare reports
 

Dear ladies of the anal interest in this thread,

How are your dares going? How did you find them? I always appreciate dare reports, either here in the thread or via PM.

Thank you so much!! I will do this the next time I have the apartment to myself - and I don’t think I can manage a full workday with the large silicone plug but I want to do it with that one so I’ll probably wait for a weekend and run some errands :) I’ll report back once it’s done but it sadly might be a couple of weeks!

Thanks for the dare. That sounds like a lot… is it safe to have pee up my ass? I don’t want to get an infection or anything… I’ve never had the cum dildo up my ass as it’s too large so that maybe a problem. But the idea of an enema intrigued me. I haven’t had any liquids in there yet.

I‘m sure it‘s fine, it‘s your own pee and it‘s generally considered sterile. Although I‘m no doctor!

Well then you have to be able to get the cum dildo up your ass first! Otherwise, you can use a funnel.

This could be interesting.
I have never done any anal games, but I have done vagina games.
I am student and live alone.
My toys are a couple of whips,handcuffs, a shock dildo, icy hot, regular dildo, and clamps.

Try again
 

I can try this again, please can you give me another dare?
Thx :)

Warm up your asshole with a finger and icy hot as lube. Also put some on your clit to get excited.

Put either of your dildos into your pussy, keep a finger in the butthole. Add another finger. How‘s the DP?

Take out the fingers, keep the vagina dildo, and whip your butt cheeks a few times. Try to get some butthole hits as well.

Then insert the second dildo into your anus. When you are fully DP‘d, shock yourself a few times.

Remove the dildo from your pussy. This should give some relief. To change that, try and see how many fingers you can fit into your butt next to the dildo that‘s in there. Can you do three? If so, try to put both dildos into your asshole at the same time.

Start off by repeating what you did last time: Three plugs in your ass, at the same time. Keep them in there for 15 minutes.

Then take either the largest plug, a dildo of similar size, or a household/food object, and lube it up. Sit in front of a mirror so you can bend over and look at your butthole. Put the object in your ass as deep as it will go, then remove it fully, with some speed. Jam it into your ass again and remove it. Each time you repeat, be a little more forceful with the insertion and speedier with the removal. Do this 100 times — count out loud. This will feel tedious, I know, just do it. You should feel your hole starting to loosen and open up. After the 100 time, pull out the object, keeping your anal muscles relaxed, and look at your butthole in the mirror. It should be completely open. Shine a light into it if you want to see. How long does it stay open before you „wink“ it closed involuntarily?

To reward your butthole, get any small fruit/veg item or piece (like a grape, piece of a banana, or similar), open up your ass again with some dildo/object thrusts, and drop the item in there. Plug up with any plug you want (might have to be big now because you‘re so open), and keep wearing it for at least an hour afterwards. Nicely done!

Dare
 

I am interested in a dare! I have a 5 and 10 cm plug, and a new tunnel plug. We can discuss the rest on kik! Onepiecelover12