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"I never had a chance to practice with women's clothes before."Dana laughed. "I wasn't trying to be critical. I was just making an observation." She leaned back, arms splayed behind to prop up her torso. After a moment, she sat back up. "No, no. Bunch up the hose so you don't ... like this!" She took the panty hose from Steve and demonstrated. "It goes on a lot easier."Steve frowned. "I'll be glad to get back in my own body," he said with genuine conviction. He picked up the blouse - an ecru long-sleeved cotton shirt with colorful red and yellow and green floral embroidery. "This is so ... " He visibly recoiled from the feminine garb.Dana smiled. "I know. You think it's too feminine. But it's what _I_ would wear, so you have to wear it. Uh, uh!" Dana called out quickly. "Put your bra on first." She watched, amused, as Steve struggled with the bra, then with the 'reversed' buttons of a lady's blouse. Finally, Steve pulled on his long khaki skirt and buttoned it.. It felt weird at first, but once I got comfortable I really did like it. We kept dating for about another month and we worked up to being able to fit two fingers in my hole. After we stopped dating I started using my fingers and a small vibrator in my ass while I was masturbating. It made me feel so dirty and felt so good, I loved it. I would often take a finger or two in my butt while having sex, and even worked my way up to a small dildo.The first time I actually had anal sex was Thanksgiving night of this year. I stayed in town because I had to work until 5 on Thanksgiving. After work I went out to a bar with one of my fairly boring coworkers because my roommates and my friends were out of town for the holiday. By about 11 my friend decided she wanted to go home. The combination of a bit tipsy and knowing I had the apartment all to myself made me pretty horny, so I decided to stay and see if I could meet a guy. My friend left and it wasn't 10 minutes until this very very cute guy.
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