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Obviously these will be written with Ted’s permission and a little help. Enjoy!!xSo Ted and I got into the whole playing with others thing in our ea...ly fifties and the first couple of guys I had fun with were very well endowed, which I just loved and thus decided this was my main criteria for a potential playmate. However there have been a couple of occasions when it felt like I had “bitten off more than I could chew so to speak.”We were on holiday in the Caribbean and I had gone back to our. " I'm fine, Miss Fuller," Cassie said a bit loudly. "Um, sorry. I'll be getting along to my next class. Bye."She quickly turned and fled again.Cassie now understood that something was seriously wrong concerning Marcie, and it had something to do with the Principal. She had wondered why Principal Bendon had remained largely silent through everything that was happening at the school. Was she instead focused on doing something to Marcie all this time?The frustrating thing was that there was. Closing her eyes, she takes a deep breath.“Relax Natalie. Just relax.”She pushes back harder this time, much harder than she had when she first tried it in her pussy, and feels the dildo bending under the pressure. She wiggles her ass a little, trying to make sure the cock is right on the whole.“Come on. Come on.”She pushes back even harder, now using both hands to hold the dildo in place. And then, with a shooting stab of pain, the head pops into her and starts to push her virgin asshole. This device I had modified slightly the previous night – drilling it full of 2 mm holes, all round the circumference in the first inch after the tip (for all those copy cats out there, drilling from the outside inwards so as not to leave any rough edges). With the little hole relaxing and expanding, I started inserting the dildo (well lubricated as I knew I had only one chance at this and would not want her to have a bad experience – the first time is what will swing her to be more.
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