An Introduction to Crossdressing Pt 4 - Sex Stories

An Introduction to Crossdressing Pt 4

... afternoon. Heather said that they were booked for the day but if we were willing to add a fifty she was sure she could get Amanda to stay late and take care of our makeup. We agreed to the deal and were told to come to the side door at six which left us about five hours to kill and we decided to go to the shop for more clothes. When Jackie and I got to the shop, we headed to the clothing side immediately, acting like two giddy school girls. As I was looking for the shortest possible skirts, Jackie was looking over the shoes trying to find the highest heels. Heather stopped by to see if we needed any help and I asked her for suggestions for a top to go with the super short black skirt I found. She found me a sheer red blouse that would go great with the red corset underneath and I went to try them on while she helped Jackie with his shoes. I removed my dress and put on the blouse, loving the way it looked so sheer that I could see my nipples just above the corset. Then I pulled up the skirt and saw in the mirror that it just barely covered my ass and if I bent over even a little, there was plenty to see. 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 walked away, he looked over his shoulder and said that he would prefer his outfit to be all black. When I started to regain my strength, I changed back into my dress since I didn’t think a see-through blouse was appropriate for the daytime. I then walked around and picked out all the parts of Jackie’s new outfit and brought everything to the cashier. I paid for everything since Jackie had already treated me last time and then we headed out for a late lunch. When we got back to the hotel, we both took quick showers and then put on our new outfits. By the time we were finished getting dressed, we had just enough time to get to the shop for our makeup to be done by Amanda. She took her time on each of us and did a superb job for which we tipped her well. It was about 7:30 as we were leaving the store and it was getting pretty dark so we decided to head to the first club ...