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I didn’t want to scare her away and get too intense too quickly with her so we just all continued to drink and catch up on what was going on with our lives. Towards the end of the night, Greg decided to go to the bathroom and it was just Courtney, Portia and I at the table. I am typically a pretty calm and laid back guy who isn’t too forward but for some reason I felt the need to seal the deal and bluntly said to Courtney, “So, when are we going out?” right in front of my friend Portia. What? Did that just come out of my mouth? Me? Portia, knowing me, knew that this was out of character for me and turned and watched Courtney intently for her response. I will have to admit that it was a pretty bold and cocky move but it was done with such precision and confidence while not breaking eye contact with her gorgeous ice blue eyes. She said, “I don’t know, Ryan. How do I know that you’re a good guy and will know how to treat me right? I said confidently, “You don’t. That’s the excitement of. ..please may I cum Master? My fingers dig into her clit harder and faster as my thumb pushes deeper inside her. I see her ass cheeks clench around the anal plug and her legs begin to tremble. Yes my pet, you may cum. Her moan is long and low from deep within as she reaches her climax. Her head jerks back as the spasms over take her. I reach around and pinch her clit between my thumb and fore finger as I thus two fingers into her juicy pussy. She moans and bucks as my finger drive in and out of her. She struggles against her bonds as she racked with her orgasm. The waves of pleasure begin to recede and slumps over the back of the chair her breath is ragged as the last of the spasms subside. I move around from and take her by the hair pulling her face up. "Thank you SIr...thank you Sir". Her face is flushed and her her hair wet with sweat. I push my crouch forward and rub the fabric of my pants over her mouth. She gives a moan as she traces the head of cock through my pants. I unzip and.
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