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I walked out of the dressing room to show Jackie my outfit and to ask him what he thought and he was walking around in six-inch heels like a pro. He turned to check me out and his mouth hung open and all he said was, ‘Wowww.’ I took that as a good sign and then asked Heather where the stockings were so I could get some red and black thigh-highs to go with my new outfit. As I was perusing the stocking collection, Jackie strutted over in his black stiletto heels and started fondling my ass under my skirt. As he started rimming my hole with his middle finger, he told me that my new outfit was quite sexy and he wanted one to match. I told him that if he kept up what he was doing, mine would be dirty before I even paid for it, so he led me into the changing room and dropped to his knees. It only took about a minute before I was cumming in his hot mouth and he didn’t spill a drop. After Jackie stood up, he leaned in and gave me a great kiss along with half a mouthful of my own cum. As he. When we got checked into the hotel and into the room, I grabbed Sierra by the arm and pulled her to me and kissed her. She giggled and pushed me off and told me that she wanted to try something and that I had to be patient and do what she asks without question. I gave her an inquisitive look and she just said to trust her. We unpacked and went to a small café for dinner. After dinner we walked down to the Fort to see the sunset and sat on one of the benches holding each other. My cock had been restricted all day and it was getting to be unbearable. I whispered in her ear that it was hurting and she reached up my shorts leg and began to pull it off. The ring came off relatively easy but the stretcher on my balls wasn’t, I had built up such a load that it wasn’t coming off very easily. She looked around to see if anyone was in the area and there wasn’t anyone close, so she unzipped my shorts and pulled my cock and balls out. This allowed her free access to stretch the ring over.
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