As it got wider and wider I could actually feel my anus stretching. Trying my best to relax I kept pushing ever so slowly. It was only half-way in when I stopped and had a moment when I felt I had to ‘reset’. So I squeezed my ass tight and pulled it out completely. By this time Jenn was now kissing my chest, licking my nipples and stroking my hard penis, but still quiet and supportive. I still had my eyes closed, but I heard her whisper “Please don't hurt yourself babe.” After a few hard squeezes of my empty anus, I was ready to continue.With a quick breath, I pushed on my opening with the toy again and it made a much smoother entrance this time. I started gradually getting it further and further and now I could really feel the stretching. I had to start slowly pumping it in and back out slightly, then further in and back out slightly. I continued like that as it got closer to the thick base. There were a few moments where I had to hold it in place and take a breath. It was starting. “Phone.” Without thinking or pausing he reached into his suit jacket and handed her his phone. She accepted the phone and without looking at it she tossed it behind her head where it landed with metallic breaking sound on the solid marble floor. “You won’t need that.” Stuart started to feel uneasy on his feet. He couldn’t tear himself away from the hypnotic gaze of this woman. His arms were like lead weights at his side and it felt as if his feet were encased in concrete. She regarded him for a full minute. Her expression never changed. After what seemed like an eternity she finally said: “You need to learn your place when you’re in my store. Walk to the back of the store and go behind the counter. You see that door? Go through it and wait for me.” Like an automaton Stuart complied. His mind was completely blank. His fear was gone and was replaced with a feeling of resignation. He was not sure what was back there but at that point he didn’t care. He made his way to the room at the.
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