For the two years prior we'd had quite a few mutual masturbation sessions. This had progressed from jacking off while talking about various girls we knew in school to jacking off each other. Of course, at that time neither of us had actually done anything with a girl, but that never slowed us down - quite the opposite. One day he convinced me to wear some of his sister's clothes, namely a par of panties and a bra, while I jacked him off. I hadn't argued with him since I had secretly worn female clothes for several years. While I jacked him off, I easily fell into the role of being a girl and would often lose myself in that fantasy. On this particular day I had something special planned. I was up early and as soon as I had the house to myself I began making preparations. I showered quickly, shaving my legs and beneath my arms and then carefully applied makeup so that I looked much more like a teenage girl. After that I brushed my long blonde hair and painted my finger and toe nails. ”A moment later, they were under the big oak at the far end of the yard, seated with their backs against its retaining wall. They faced away from the house, and were shielded from the bright moon by the oak’s thick blanket of leaves.Carla weighed the two bottles in her hands and passed the lighter one to Ana, then yanked the cork on hers and tossed it into the grass. Less sure, Ana followed suit, her delicate toss giving away her caution. “So – what do you think about your first time?”Even in the filtered moonlight, it was obvious to Carla that Ana was blushing. “Wow, I mean … I loved it. It was a little strange for me, but so natural, you know, which made it stranger … that it didn’t feel strange … you know?”“I think I do,” Carla replied, before tipping her wine bottle to her lips.Ana looked skeptically at her bottle before doing the same. The wince that followed told Carla something else.“First time for wine, too?”Ana nodded. “Except for church, yeah.”“So many things for you to.
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