As I massaged she began to grind and my thumb started to enter her. This leads to an increased tempo and her orgasming wildly. I have no objection, this is free sex. This is about me enjoying her and her enjoying me. And we do. Because we are truly in love with each other and have been for a very long time. That is the honest truth. However we cannot ignore things that must be addressed. And the timing could not be better. That caring caress of her little pink asshole has prepared it for the punishment that is now due. I withdrew from her, only for a moment long enough to plunge forward. Forcing the head of my cock through the tight restriction that is her ass. This is the beginning of the punishment. The end of any free sex. This is going to come with some pain. I know it causes her pain, because it causes me pain, to break through the tightness. Pulling at the head of dick. But I shut my pain out, because this is not about me or my pain. Only her and hers. As I work it in. If he says no then you win and get your spa day.” Almost as soon as I sent my text I got Stacy’s: “Okay. Deal. ” I knew the night would be interesting. An hour later I arrived at our apartment just as Stacy and her friend Jessie were leaving, and let me tell you, wow… They were both dressed like the twin secretaries on one of those movies where most of the dialogue is moans and grunts. Stacy had told me what she was wearing before, but words didn’t do justice compared to seeing it in person. She had done just a single button on her shirt, letting her lacy black bra show up top, and her stomach with a small stud, down below. Her tight skirt came just a few inches down her thighs. You could just make out the top of her thigh highs peeking out from under her skirt. She had topped off the whole ensemble that bright red lipstick she knew I loved. Stacy oozed sex appeal. From my expression they could tell they looked good. Stacy wrapped her hands around my neck and pushed her lips to mine..
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