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His mom was surprised, but delighted, to see her son having such a good time with a girl. She often wondered if he'd ever be able to get along with them, but it seemed Cindy was bringing him out of his shellWhen they finished lunch they went back up to Cindy's room and she asked Jeff why he was holding her pantyhose up against himself when she came back. "I'm not sure, it's just that as I was putting all your pretty clothes away I couldn't help but imagine what it must feel like to be able to wear such nice, pretty things. And I thought about how cute you are and how great you must look wearing this stuff. I guess I was trying to imagine what it must be like to be you," he confessed to her. She thought that was the sweetest thing anybody had ever said to her. She ran over to him and hugged him and said, "Well, thanks for saying I'm cute. And as far as feeling what it's like to be me, well, you'll never really know, but you can at least know what it feels like to wear my clothes.. She asked, "Do you do anal? My boyfriend takes it in his ass all the time but Autumn won't. She says it is too big. Come to think of it, I have never had a girl take me in the booty. You want to give it a try?"Considering how much I enjoyed anal with my boyfriend and even though Mercedes's penis was twice as thick, I curiously agreed, "Sure but please use lots of lube and go slow."As she disappeared into the bathroom to retrieve the lubrication, she agreed, "I always do baby."Soon, I was on all fours on the Ottoman with my bare feet hanging over the edge. Mercedes slathered her dong with plenty of lube and wiggled the tip against my anus. Gritting my teeth, I prepared myself for entry. She pushed slowly and the head stretched my tight sphincter until it popped in. I gasped in pain but took quick choppy breaths to deal with it while I instinctively began to pull away.Mercedes grabbed my hips, "Don't run from it baby. Stay strong. Let me get it in."I could feel inch after inch slowly.
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