Crossdressing pics

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Oh Rider.....

I want to dress up really special for you - what do you like most?
 
I'm sure you must have the desire to show your stuff again. This is a word you won't hear me say very often: PLEASE?

Maybe in a few months, but for now i'm retired from the game. I don't even have the lowliest thong anymore.
 
Painfull....hmmm, well pain is such a relative thing now isnt it.

I wouldnt call them painfull, they are very restricting and I am always aware of them because of their weight and the fact that they do not expand, flex or give in anyway such as a rubber ring does. As I approach orgasm and my cock starts to swell the exposed part of my shaft becomes very veinous and thick, and my head swells to an incredible size,goes dark purple and very very hard. When I cum its an incredible release, its not just the feel of ejaculation, its as if my head explodes. My cock cant pump or expand under the rings so it is all left to the top of the shaft and head to handle the chore. At first a couple large drops of cum drip out, there is a pause of a few seconds( the calm before the storm) and then a burst of delicious warm seed explodes out of me. My head hurts at bit at this point but it feels soooo good ( see..its all relative;)), I shoot a couple more bursts with good velocity and am sometimes so aroused I keep on going until round 2. When I take them off there are indentations along my shaft from each rings which can be a bit tender if I`ve had a good session but again, its all relative.

Billy-boy's cock has to be trapped like that. I don't think he would like it, but I think his pain would be a huge turn on for me!
 
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