I could feel my cock stretching to its max when I felt the dildo pressing painfully on my sphincter. Judy pushed slowly and I could feel every bit of ...he head as it entered, and then suddenly the pressure was off and the pain subsided as the head was fully inserted."How do you like that, Jed?"I was still too breathless to say everything was just fine, and I wasn't sure if this was going to start feeling good. I just grunted an assent. I could feel the dildo as Judy continued to push and it. You should see the look on his face when I exit the bathroom in nothing but a towel. I laugh and tell him to turn around. Rummaging through my suitcase I find clothes for the evening, I return to the bathroom to change. I know his eyes were on me as I walked away. This is NOT how I had planned this. After dressing I apologize for the awkwardness of the situation and he puts his hand on my cheek and tells me it’s quite alright. I am pulled towards him staring into his eyes. His eyes are begging. More

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