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We were eventually seated and enjoyed a nice meal before she dropped me off at home. “I had a really good time tonight,” she said. ”As did I,” I replied, “Maybe we could do this again sometime?”She agreed and gave me her phone number so we could continue to talk. We continued to go out and eventually I asked her to be my girlfriend, to which she gladly said yes. A few weeks later after a night out I found myself at her house all by ourselves. She put on a movie and cuddled up with me on the couch. The perfume she had on was intoxicating and it felt wonderful to have this gorgeous woman pressed so close against me. We started some heavy making out which was typical over the last few weeks we spent together. I suddenly felt a hand slowly creeping up my thigh. While she had expressed interest in doing more than just kissing, I had been reluctant due to my inexperience. I quickly sucked in a breathe to calm my nerves and managed to urge her forward by boldly grabbing ahold of her firm. Despite himself he pulled the sissy off his cock saying "let's try out your pussy".Immediately Sissy assumed the second position which would become her favourite. She got on all fours lowered her shoulders so that she was resting on her elbows and then reached around to take out the ever present butt plug. "That's okay, leave that to me" Daddy said. He remembered the previous evening when he had gently fucked his sissy with the butt plug. He started to pull it in and out of sissys pussy but quickly realised that this was much bigger and fatter. His admiration for the dedication his sissy had shown him knew no bounds. He thought he actually felt love for his sissy.As he pulled and pushed on the butt plug he was aware that there must be some pain for sissy, but also knew that if he were to be able to get his own cock in there and to fuck sissy like they both wanted, that he had to be cruel to be kind. He pulled and pushed on the plug watching the sphincter ring tightened and loosened.
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