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Old 01-01-2021, 08:13 PM   #31
PredicBabe
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Hey, I'm back!!! I am terribly sorry for having vanished, and I really owe an explanation here.

You might have wondered why I disappeared. Well, it's been because of this (last) year's malady. I don't want to go too deep into it because it has been truly hard, but the virus hit my family first and then me, and while we are all completely fine now and we could enjoy the last bit of Christmas without worries, there were moments in which things really seemed to go bad (like, *really* bad). As I said, at the end it all ended up being one big scare of which we all came out with no long-lasting effects, but since it took us by surprise, I have not been able to think about anything else for a very long time - including GD and the post I had started here.


Well, now that things are better I am resuming this task and taking it up from where I last left it. I am having some time tonight, so I will do what I was doing (30 mins with medium plug, widest part stretch for 10 mins, and then trying on the big plug) and will report in the morning.

Again, I am so sorry for disappearing, but now I am back amd stronger than before, so I will give my best to fulfill this task!!!
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Old 01-01-2021, 09:34 PM   #32
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Glad to see you are okay. Welcome back.
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Old 01-02-2021, 09:22 AM   #33
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You might try this.

Sit on the floor with you legs bend under you. Place the but plug on the floor (lots of lube) and sit on it. In this way your legs will remove some (but not all) of the pressure down on the but plug.

Now watch some porn (likely some anal), or other activity that makes you really horny. Try play with you pussy and edge a few times. Making you really horny will allow you to "want" to put pressure on the plug.

One thing you should be aware of is when it do goes in, be careful when you take it out, to avoid hurting the ring muscle the first few times.
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Old 01-02-2021, 02:28 PM   #34
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Alright, so I did the dare last night and this is how it went.

Since it had been long since I worked on this, I decided to take a lot of time to do it so I could use as much time as needed. I also added a small modification (a small surprise, you could say if you like reading reports) to the tasks that, I think, became key for things to turn out as they did.

I started by inserting the medium plug in (I don't actually need barely any lube for it) and keeping it in for 10 minutes while doing some stuff on the laptop, doing some kegels every now and then. Once I felt completely comfortable with the plug, I added the modification: a few days ago I read a dare about hanging some weight from the plug to make the anal muscles work and get tired (and therefore to stretch them easier), so I did just that - grabbed some cord and hung a 750ml water bottle from the plug. I squatted on the chair, so the weight would be hanging, and held the weight for approximately 10 minutes before removing the weight an taking the plug out. It definitely worked - my ass felt quite stretched and ready for the next step.

So I grabbed the big plug, lubed it up really well, placed it on the chair, and got on it. After the exercise done with the medium plug, the first part of the big one slided in really easely, but I felt the widest part resisting to go in, so I decided to take it easy (I still remember the last time's sting) and moved just slightly up, to a comfortable width, to do some kegels. After the exercise, I went back to push the plug deeper, but it still was not enough to comfortably push the widest part through. I started "bouncing" softly on the toy and, slowly slowly, I managed to work the plug in, stretching me without pain.

It finally went in. I pushed it slowly to ensure there was no pain, and when the plug went all the way in, the feeling of fullness overwhelmed me. I am extremely sensitive to physical feelings, and for a moment I almost panicked at the feeling of such a big object inside me (that would have meant taking the plug out), but I grabbed a hold of myself and breathed in and out till the strong feeling subsided and the plug became bearable. I was amazed. My ass felt soo comfortably stretched, and taking the plug in had been easier and more confortable than what I had imagined.

I decided to keep the plug in for some time to get my ass used to it, but I was fearing that my sphincter would get "closed" around the stem of the plug and that I would do some damage when taking it out. So I decided to do the same exercise that I had done with the medium plug. After holding the plug in for some minutes, I attached the weight to the base and knelt on the chair, letting the weight hang and pull on the plug. I knew that my automatic reaction would be to clench my muscles to resist the weight (and so I did), but after a few minutes, and knowing that the plug would not get out that easily, I relaxed and just cautiously enjoyed the feeling of the weight pulling on the plug and of the toy's widest part pushing against my muscles.

After some time in this position, I removed the weight and carefully took the plug out. It slided out without problems, since the exercise had perfectly fulfilled its duty of softly stretching my sphincter, and left me gaping, feeling so stretched open. The feeling of my ass open was such a big turn on, and finished the whole ordeal by masturbating and orgasming to an anal stretching video.

The experience has been sincerely amazing. Today I have been feeling stretched (without pain) the whole day, and now I am wondering if I should repeat the routine tonight or if I should give it a 24h rest before repeating it.

Please, tell me what you think and, if you have any ideas of exercises or dares to do for the next day I take the big plug in, just let me know
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Old 01-02-2021, 07:24 PM   #35
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I'd do it again and maybe add a second bottle and double the weight or maybe just fill the second bottle half and then the next day do double and so on
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Old 01-02-2021, 11:18 PM   #36
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You should probably wait a day but I would find it fun to see how you would do with more and more weight on the plug. Maybe you could use a bigger bottle and continuously add water.

For example, insert your plug and get an empty 2L bottle. Masturbate for 2 minutes, if you cum in the two minutes add 250mL if you don't add 125mL. Whatever weight the plug comes out at you will need to do the inverse with the large plug, so 1.5L with the first plug means 0.5L with the large.

Feel free to make modifications, for example maybe instead of masturbating you could strap a vibe to your clit. Or you could change the time or additions.
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Old 01-03-2021, 05:35 AM   #37
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Alright, I'll increase the weight on the plug. Should I do it in any specific way? Or just adding weight and seeing how much time or weight it takes to pull the plug out?
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Old 01-03-2021, 09:46 AM   #38
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Go with the increased weight and seeing how long it takes to pull it out
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HMU on Kik and keep my sissy ass stretched or wedgie me till I'm begging you to let me go
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Old 01-03-2021, 10:19 AM   #39
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Yessir, will do that
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Old 01-03-2021, 12:00 PM   #40
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Have you tried taking your dildo anally yet? Don’t try to fuck it yet, just use it like a plug to get a stretch. No neck means a better stretch when it’s inside you, but you’ll have to use panties or a rope harness to hold it in.

Dare 1: put your dildo on a chair and sit on it for at least 15 minutes. If depth is a issue, you can stack books to either side of the dildo for you to sit on.

Dare 2: put your dildo in, and then put on a rope harness, panties, or leggings to hold it in. For at least 30 minuets, clean your home while it’s inside you.
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Old 01-03-2021, 01:01 PM   #41
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No, I haven't tried the dildo yet, but I was also thinking that I should start with it.

Dares noted! I will do the plug weight to prepare my ass and then I'll do the dares with the dildo. Thank you very much!!!
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Old 01-04-2021, 10:46 AM   #42
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A'right, here's last night's report.

I started the session with a small warm-up that I had been given through PM. I applied a teeny tiny drop of hot sauce on my ass while using a vibrator on my clit, I I just rested on my bed, edging a couple of times, until the hot feeling subsided. Since the amount of sauce I had used was minimum, it didn't take long for the sensation to disappear, but by that time my pussy was so wet and my ass felt nicely warm. I inserted the medium plug in and edged once again, which helped my ass get used to the full feeling of the plug, and after that I proceeded to do some kegel exercises and to push the plug out of my ass with just my muscles, pushing it back in with my hand.

After a few minutes doing this, I felt I was ready to get the big plug in. And I indeed was: I lubed the toy up, set it on a chair and sat on top of it, and unlike the past days, this time it barely took a minute or two for the plug to slide inside me. The widest part of the toy still stretched my sphincter in a not-so-pleasant way (it did not hurt or sting or anything, it just felt like a bigger stretch), but my ass soon adjusted to the big size of the plug, and I found it way more comfortable than the last times.

At this point, I decided to experiment a bit and to leave the weights part for the end. Instead, I did some kegels and repeated the exercise I had done with the medium plug: pushed the toy out until it almost popped out of my ass, and then took it back in, all this completely hands-free and using only my muscles. I could feel my ass ring slowly stretching, and when I felt comfortable with the exercise, I held the plug base with my hand and pulled it out of me until it was about to pop out, with the widest part stretching my sphincter. I held it there for 30 seconds and pushed it back in for 30 seconds more, repeating this sequence three more times. By the time I finished, my ass felt so wide, and I thought it was time to try the dildo.

So I placed the dildo on the chair, lubed it up and sat on it. I was expecting some resistance and stretching, but lo!! It went fully in in just one go!! It was too long though, so I had to stack some books I had prepared before hand so I wouldn't have to be squatting the whole 15 minutes, but I sat there with the dildo almost impaling me for the whole time, watching some porn and gdtting wetter and getter at the thought and the feeling of ny ass being stretched.

After the time was over (I didn't do the 30mins walking around, because I just could not hold the dildo in since it's so big and heavy), I stood up amd grabbed the big plug again. I inserted it in my stretched ass and edged once, just so the sphincter would close around the plug's neck, before putting the cord with the weight around the base. This time, I used 1.5 kg, and half squatted on the chair while watching porn and trying to hold the plug in. I could feel my ass squeezing the plug, trying to resist the toy, but after 15 minutes my ass was so tired that I just relaxed and felt the weight pulling the plug out of me. It still took some time, though, since my sphincter had closed around the plug's neck and the weight was not heavy enough to pull the wide part of the plug through my ass ring in a short time. The weight still hanged for some minutes, pulling veery slowly on the plug, forcing it through my ass ring, until it finally won the battle and the plug popped out of me.

The feeling of having my ass forced open was enough to make me orgasm, and I enjoyed the wild ride of feeling my ass stretched open and having an orgasm due to it. The experience was truly nice, and now I know I can definitely take the big plug AND the dildo in my ass!! I would say it's a goal completed!!
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Old 01-04-2021, 11:19 AM   #43
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Very nice! Congratulations!!

How about a rule for this week? You’re only allowed to cum with the dildo in your ass, and only after it’s been inside you for 30 minutes that day. The time is culminative, so it doesn’t have to be the 30 minutes immediately before cumming.
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Old 01-04-2021, 12:43 PM   #44
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I glad you loved the plug getting pulled from your ass with weights part.

I honestly want to try some of the stuff you have done cause I'm in the same boat of I have a small and medium plug that fit fineish, but then I have a large plug that is still way to big that I get that sting before I hit the wide part. I might have to try from ground one like you did and follow the dares on my own since it sounds like it really worked for you
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IM A WORTHLESS SISSY

I am trapped in diapers almost 24/7 for an unspecified amount of time. Release of 3/1/23 at the earliest.

M/23/Straight

kik- Anonymos404

Sissy Name: Anna Naomi

Loves, Likes, Limits https://www.getdare.com/bbs/blog.php?b=93084

PM dare- https://www.getdare.com/bbs/blog.php?b=90880

Spoiler:
HMU on Kik and keep my sissy ass stretched or wedgie me till I'm begging you to let me go
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Old 01-04-2021, 12:44 PM   #45
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Heart Nice thread

Hey there, since you like to destroy your butt with heavy objects, why not push a boules ball in there ?

I've been wanting to do this for a while, but was never able to fit it! But if you're able to I promise I will give it another go !!

Goodluck
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