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Gwyn’s POV:My ploy to end my spanking when it really had begun to hurt had failed and Santa’s spanking of me had continued with a zealous appetite on his part, but now it was my femme challenge to cease his spanking while my bottom was still intact without a lasting hurt while relishing the stingy feeling that made feel alive for the sexual circus I was now plotting.A strange feeling worked its way up into my loins as I lay over the lap of my Secret Santa.I began to be honest with myself and acknowledge that I actually enjoyed being spanked by him, well as long as it didn’t get to serious. “Hee, Hee.”Sure he was spanking me and my ass was turning considerably redder, but I was handling it just fine, thank you sir. Actually I was quite proud of myself.The pain in my butt was manageable and I was not squirming around and crying like a little girl of eight certainly would. Boy that would really humiliate me!Instead I was relishing the dreamy feel of the masculine hand on my bottom. We had met several months before while walking on a beach very popular with the gay community. I am a very passable full time crossdresser and was wearing only a bikini when we met. I told him off the bat that I was a CD but at first he didn't believe me. After some convincing, we agreed to meet up for coffee and after a short time, began dating. He is married but has a thing for shemales. We began having sex a few months later and he likes to play the role of a john with me as his whore. I liked the role and played it with enthusiasm.I arrived at the park and he was already there. At 6'03" and 240 lbs, he is a total stud. We kissed and headed down the trail toward a stand of redwoods where we could be concealed from anyone else who might walk by. "You look so hot!" he said as he slid his hand across my ass concealed by my tiny shorts. "You little whore, your're wearing a thong!" he said as he ran his finger down the narrow strap between my ass cheeks. We set off hand in.
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