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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. Tim was a nervous, conservative, young academic and the only visitor to Julia's flat who had met her mother and had not uttered the ritual "You two must be sisters" speech. This upset Julia's mother more than she cared to admit. When they first met to talk about his tax problem Timothy had just looked at the former oh-so-nearly Bunny of the Year, blushed, looked away and mumbled a polite greeting.Julia's mother thought he might be gay, and said so when the diminutive philosopher had departed. Her daughter disagreed. Timothy, she said, was known to be shy, and despite his small stature and stammer, he was regarded as"quite a dish" by the faculty females. Julia hoped one day to coax him out of his shell. Her mother was skeptical."I've spent hours on his tax problem and he hasn't once made a token pass at me!" she exclaimed, "It's not natural. Just wait until Friday, when I see him next. I'll show you how to 'coax' him!"Julia should have heeded the warning."Be a Darling," Julia's mother.
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