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I then felt another sensation of coolness. This time, Jimmy had squirted some of the lube directly onto my asshole. I froze, knowing what was about to happen but allowing the event to unfold like a spectator, rather than the participant I was. I had tried anal sex before with my ex-boyfriend. The first time was horrible but the second time was somewhat pleasurable. He was only five inches long, though. Jimmy was eight inches and much thicker. I was scared and went to mutter an objection but none came out.His cock head pressed against my hole. My ass was tight, nervously tensing. He pushed forward regardless. I felt his thick head enter me first. He did not thrust in hastily as my ex had. Instead he slowly pushed his thick cock into my ass despite my hole’s natural reaction to tighten up and restrict entry. He had broken the barrier. His thick cock was now in my ass and he held it there. “Ow, ow, owwww!” I cried My body was calibrating this new feeling. It hurt so bad. This type of situation had arisen before and I had always dealt with it successfully. The technique was simple. It takes only a couple of minutes for the train to get from one station to the next, not long enough for FUCK to take effect, so I would simply get off at the next stop and wait for the following train, seldom more than five minutes later. Gentlemanly fellow that I am, over the previous couple of weeks I must have preserved in this manner at least half a dozen unknowing pretty girls from a life of sexual enslavement. At this point the train came to a standstill in the middle of the tunnel. Everyone sighed wearily, including the young couple in front of me. I mentally withdrew my previous complacent thoughts about how to cope with the situation. As I contemplated the pert little bottom in front of me and the rich golden hair hanging down from above, and remembered the cute precocious face I had glimpsed when she got on, I knew what would happen unless I quickly put some.
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