Not sure what the more humiliating part of this is, actually doing and somehow enjoying these things or admitting that I did here, but here we go, I'll battle through my cringe to report on what I did last night.
My small dildo is about 5 inches and fairly skinny
My medium dildo is about 7.5 inches and quite girthy
My large dildo is 8.5 inches and really fucking thick
Since the last time I did a dare like this I leaked a TON of precum and cum I decided to wear a condom so I didn't make a mess everywhere and so I didn't waste any if I had a task involving cum at some point.
I flipped a coin for which version I got, despite preparing my ass the best I could I was still not wanting the A2M version...which is exactly what I got.
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3 - Do the same as role one except pour a little lube onto them instead. If you have no lube, that's bad luck...
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I had tons of lube, dont worry! Preparing my hole knowing what might be to come left me feeling pretty vulnerable, naked lying on a towel on the floor..
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1 - Slowly slip a single finger in as far as it can go and leave it there a minute before sliding it back and fourth 10 times slowly. Suck it clean.
2 - Do roll one but after you're finished, go again the same way with two fingers. Suck the clean and go again.
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This kind of just felt silly lying there with 1/2 fingers up myself. I quickly pulled my fingers out of my hole and into my mouth without allowing my self to look at them and think what might be on them. The lube I used was 'cum lube' so it had quite a thick consistency which made the experience a little scary in the mouth!
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4 - Small dildo: 50 pumps, fast, moderate. Only 50 pumps?! Take it out and suck it clean before rolling the dice again to see how many times you have to re insert it and fuck yourself before taking it out and sucking it again and again.
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I rolled 5 for this so 5 x 50 hard pumps with the small dildo sucking it clean between each set. At first I was feeling extra humiliated because the dildo closest to my cock size slipped in so easily and wasn't doing too much for me but on the 2nd set I found an angle that felt pretty amazing and I could feel my cock start to leet precum. I couldn't help but look at the dildo each time I pulled it from my asshole but 'happily' it always looked clean, just a little creamy (hopefully jut from the lube and the friction!!). I felt like such a slut cleaning my juices from the cock and having it rammed straight back into me again and again.
This scared me, my ass was pretty slick right now but it had been quite a while already since I lubed anywhere and that was just the outside of my hole. Maybe I would be able to take the medium dick but the large would be impossible.
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Medium dildo: 450 pumps, fast, shallow.
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I did this on my back with my knees pulled to my chest. The feeling of just the entrance of my ass being penetrated over and over again rapidly by the big head of the cock was quite a hot feeling but ultimately frustrating. By the end my hole was burning a little as the lube was running out
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2 - Pull your hole apart with your hands as best u can and sit down on the large dildo swallowing it - sit on it for three minutes. Suck both the fingers and the dildo afterwards.
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Okay there was absolutly no chance at all I could do this without a lot of lube
first person to send me a punishment for this I will attempt their punishment to make up for cheating. I lubed the monster cock up well and feared how it would feel when I sat down on it. After a minute or so of wrestling the lubed cock and trying to get enough grip to direct it into my lubed up asshole I am ashamed of how easy my ass gobbled it up the first 6 or 7 inches felt like no problem at all although I felt verrrrry full and stretched! I took some deep breaths and let my body weight force the cock deeper into me until I felt its balls against mine. Omg why did I feel so proud? Why did I feel like I was a good boy for taking this cock so deep and so easily. My cock twitched and exploded in the condom the more and more I thought about how big the dildo was and how full it made me feel. The pressure against my prostate throughout felt amazing, but as the time went down I started to realise I was going to be tasting 8.5 inches into my body soon. I raised myself off the meaty dick and the suction cup kept it firmly attached to the ground so I got down on the floor with it and began to greediliy suck it clean. I could only fit the head in my mouth which made me feel like my asshole was over achieving massivly so I licked sucked and yes I even kissed my way down the cock until I couldn't find any creamy lube on it.
No lube again but I could feel my ass was almost dripping with lube still so I braved it for..
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1 - Large dildo: 500 pumps, moderate, deep.
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I put it on the wall and took it doggy style, back myself up on it with strokes as long and deep as I could get. The pain/pleasure every time the head of the cock felt like it was opening up a new part of my guts sent me wild and half way through I had a strong orgasm (the condom was now basically hanging off my dick with the amount of liquid it had collected)
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3 - Cum on a dildo and suck them all clean.
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I grabbed the medium dildo, carefully removed the condom and let all the cum and juices pour down it. I hungrily sucked it clean imagining I was sucking a cock clean that had just cum deep inside me, the mix of cum and ass made me feel like a whore and once I was done I greedily made sure to suck the large and small dildos clean as well not even caring about the taste of ass anymore.
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Likes: RISK of getting caught,dice dares,skill/forfeit challenges, semi public, light humiliation, cock torture, sounding
Unsure: pee, anal, pic/audio proof, dildo sucking/swallow
Dislikes:light crossdress, edging/denial, extreme humiliation, full public, mild ass2mouth, ball torture
Limits: Diapers, scat, full cross dress, pics/videos that identify me
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02-26-2023, 05:56 AM
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