As I've shown in past posts the squid is not a small anal intruder:
As such I have to be slow and careful inserting it. As I've gotten older and my back has gotten stiffer, I came up with a little technique involving Rosa's "Queening Chair" and an old car jack. Basically it allows me to sit relatively comfortably and with slow, progressive turns of the jack handle, insert the squid in a pretty safe and controlled way. In order to enhance the dare, I included some images of the system in action so as to give context to the effect of the squid on my 'not-that-huge-to start-with' member.
So here is Squid Dare#1:
I took a sort of "before shot" for reference. I was already a bit nervous and so I did not start out in any state of arousal.....just regular old me. Here you can also see the opening of the queening chair from above.
A bit dark and grainy, but doing stuff like this solo is not easy. Here is the squid just starting to enter me from below. You can see the top of the jack in the bottom of the picture.
Once the squid started to make its way into my bottom, you can already see me "shrinking in defeat".
Again very grainy, but still pretty solid evidence for me being fully penetrated by the squid. The jack is now easily visible.
And here is the embarrassing final result! I took this from a different angle otherwise you'd just see a tiny button-nub.
And one final angle truly showing me in an utterly defeated state.
I wrote a story years ago about my 'weakness' called "The Mushroom Effect" (click to read)
wherein I describe the feelings I have about having this "shrinking-from-being-anally-impaled" issue. It revolves around all the thoughts men deal with in being submissive and contradicts a lot of fiction that depicts even submissive and anally impaled men still being excited enough to sport huge erections even as they are violated from behind. Not me! I feel like my body reads the anal penetration as physical proof of something more "alpha" having put me in my place. And in the case of this dare, I guess this time it was Ana......via a giant squid!