As you like pain, insert your G spot vibrator in your ass, only taking it into your mouth once for lube.

With it in your ass, angle it so it touches the G spot and try to orgasm from that alone! Don‘t touch your clit. If you can‘t come like that, put as many sharpies in your butt as you can, again only spit as lube.

Sorryyy I never saw this.
Um not really anything bigger. I could buy a larger toy.
Any recommendations?

Sorryyy I never saw this.
 

Sorryyy I never saw this.
Um not really anything bigger. I could buy a larger toy.
Any recommendations?

Sorry!!! Did not log in for some time. Yes, i am still interested in a dare :)

Since I wrote, I have managed to stretch my ass to the point in which i can perfectly take the plug in, and i can take some centimeters of the dildo in if I go properly lubed. Would love a predicament bondage that would make my ass take the whole dildo in easely!!! (only if possible, of course)

Im notn super new to anal but im happy to have a dare made for me <3

Just recently got into anal! Looking for ways to help break me in and get used to having things plugging my ass

Did you do this?

Get a large glass plug on Amazon!

OK! Not a bondage expert, but position a toy under you that you haven‘t been able to fit yet, a large buttplug. Then squat down on it. You are not allowed to stand up before it‘s completely in you and will stay inside you when you stand up! Good luck, hope you have strong legs.

See how many sharpies you can put in your ass. If it‘s less than ten, write SLUT onto one of your cheeks.

Finger yourself a bit back there. When you can take two fingers, switch to the plug set. Wear the smallest one for half an hour, then go to medium. Masturbate with the medium in your butt. After you cum, leave it in for another half hour. Then take it put and try the large one. If you can fit it, you may cum again. Otherwise, try again the next day.

i'd really appreciate a dare! i have a small vibrator, and a small metal butt plug, but i've been wanting more toys, so i'm willing to buy something new! i also can use any commin household items. i love public (safely, of course), some humilation, pain, and dares that take a while. my ass isn't stretched very big, but i'd love to start stretching it more!

thank you!!

Hi! So as you‘re new to anal, I want you to keep your small butt plug in for 24h. Do it in a time period where you‘ll also go shopping, and maybe to the gym. The possibility for others to see your plug through thin leggings should excite you.

You may remove the plug to go to the bathroom.
In the 24h, you may not cum! Once you‘ve made it through the time, take a houshold object that is bigger than the plug, and cum with it in your ass. Then you should be nicely stretched!

I'd love an anal dare please. I have plenty of toys. I have 2 double penatration dildos, one is suction cup and the biggest other is smaller and not suction cup. I have 2 butt plugs that are pretty small now as I fuck my ass regularly. I have a big metal rabbit tail buttplug, I have a 3 ball type but plug thats pretty big. I have a 6inch dildo thats suction cup and a metal ribbed dildo too.
I like dice dares and being told to fuck my ass for prolonged periods of time. I dont have much privacy at home I usually get an hour to myself an afternoon in term time. Am open to hidden public dares and tempted to take anal to the next level by exploring a2m.

On a day where you will have privacy at home in the afternoon, start your day by inserting the biggest plug you can wear for a longer period before you leave the house or start working at home.

Throughout the day, feel how the plug stretches you and teaches your hole to stay open.

Once you get home, remove the plug and clean yourself up. Then take your longest dildo, and insert just the tip. Take it out and lick it. Put it in again, an inch deeper. Take it out and lick it again, the length of the shaft! Continue doing this until you can take the entire dildo and lick it clean once it comes out.

Next, take your biggest butt plug and insert it. Leave it in for a few minutes, start masturbating. Take out the plug and put it in your mouth. Cum any way you want, but the plug must be in your mouth.

Anybody else completed some dares? Or want new ones?

Wow! Thanks for this dare! I haven't managed to do the full thing yet due to lockdown 3.0! But I did manage to sneak some time to do the 2nd part.

I Got my biggest dildo with the suction cup and attached it to a flat mirror. This way not only could I slide it easily between riding it and sucking it but I could watch it slide up my ass hole and watch myself lick off the ass juice!

I put a little bit of strawberry flavoured lube on the tip and on my hole to get me started. I slid it to my ass hole so the tip just opened me up a little then I licked it off. I returned it to my asshole and slid a little further in and watched myself lick off the strawberry flavoured lube from my ass hole of the big smooth dildo. I really took my time taking the dildo little by little then licking it clean. By the time I was a couple of inches in I was pretty much lapping up the juices like a dog licking its water bowl. The strawberry lube quickly disappeared and it was all ass juice and spit!

By the mid way point I was practically swallowing my dildo eager to lap it up. I had to stop myself from sliding that dildo balls deep in my hungry ass. little by little I took more and more of the dildo and found it desperately humiliating that I couldn't wait to slide it out of my ass hole and gobble it up whilst watching myself in the mirror it was placed on.

By the time it was almost balls deep in my gaping ass hole I was practically dribbling at the thought of getting my mouth around it again and my pussy was dribbling with excitement. I made myself take it millimetre by millimetre to keep it going for as long as I could, by the time I was balls deep I was almost tingling with excitement and knew it wouldn't take me long to come at all!

When we finally reached balls deep I frantically rid the dildo for a minute or too, removed the dildo, easily shoved in the butt plug, I got my vibrator bent down and took the dildo in my mouth and continued to suck it whilst I teased my clit with the vibrator. Being extra careful not to come which was hard.
After a few minutes, I pushed the butt plug out with out using my hands, picked it up with my teeth and positioned it so I could take it in my mouth. Then I placed it against the wall and pushed my mouth all the way around it till my nose touched the wall and the butt plug was at the back of my throat! I then put the dildo back in my ass hole and used one hand to fuck myself with the dildo and the other to tease my clit! I came pretty much straight away!

Thanks again and sorry it has taken so long to reply!
I will try this again when I can get the whole thing done, but until then hope this is good enough!

Happy for more dares. Maybe some to spice up the house work as that's all I ever seem to do. (House full though so can only get away with privacy in one bedroom and bathroom, rest would have to be 'Hidden' dares)

Maybe...
 

I’m new to a lot of things, and I don’t know, if anal is a dislike as much as an unfamiliar thing. I don’t own any toys, but I have slender disposable things like q tips and candy canes...

Sounds amazing, well done! Maybe buy a bigger plug, one that would be a challenge?

For a next short dare, insert a plug in the morning and then do chores at home. Keep it in the entire day. You may only remove it to go to the bathroom. No lube, just spit! Everytime you take it out, it‘s either dry or licking it wet before reinsertion.

In the evening, but at least after eight hours of wearing it, take it out. Admire your loose, gaping asshole. Wet the fingers of one hand, put the plug in your mouth, and see how many fingers you can fit in that ass. You may cum. Take out your fingers and lick them clean afterwards. Good girl!