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She was, he told me, an extremely attractive and glamorous lady - a size 10/12. I had done some rough measurements of myself and, at just 6' tall, with measurements of 38/28/37, I reckoned I was a 10/12 also. He had never disposed of her clothes and I was more than welcome to use them all. In fact, he said, the notion of me, a young and inexperienced TV/TS in his wife's lingerie and skirts, made it all the more exciting and erotic for him. So that was it. I hardly slept that night but was determined to go ahead with this. If it didn't work for me then at least I would have tried it and could convince myself that dressing privately was enough, that I wasn't really a woman at all.I woke groggy and early on Monday morning, my bag already packed with a couple of days of male clothing, my wig and makeup. I travelled up to Paddington and boarded my train to Oxfordshire. I carried a little flask of scotch that I sipped from occasionally when the nerves got too much. An hour later I was in. Thus, neither the guards nor the prisoners were aware of her still-cherry condition.She had come very close to it on two occasions. Just before making her decision to enter the convent, she had gone to a long-awaited "going away" dance with a young soldier heading overseas to an almost certain death in the jungles of some dangerous Island. They had laughed and bounced against each other in happy exuberance like fumbling puppies discovering life. Before she realized it, Mary had spread her legs wide and the young man was guiding his long rod up into her untouched pussy. Fortunately or unfortunately for her, depending on your perspective, he had drunk a little too much punch and his cock started to spurt long streams of creamy cum before he had even reached his objective. His premature explosion startled her out of her comfortable dreamy state of mind and brought her back to the real world covered in nasty cum and under the semi-conscious body of a uniformed stranger.She had laughed.
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