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John had withdrawn his cock from Jane before emptying his balls and as I watched he pushed towards me and I eagerly opened my mouth so John could shoot down my throat at exactly the same time as I filled Jane's mouth. As I lay on the sofa,naked now, John said he liked transvestites and sometimes wore a skirt & blouse to make himself sexcited when he had a wank. It turned out Jane had a friend who crossdressed all the time and she often helped out regarding what looked good and sexy,so seeing me in women's underwear didn't shock her,and if I wanted she'll let me borrow some items from her. John urged me to go for it and I was soon wearing Jane's black bra(36A) and matching silk lacy pantys & a mini-skirt,a c-thru white blouse as well as lipstick and nail polish. What a thrill and Jane agreed it turned her on, letting me feel her soaking wet pussy. John also said he liked seeing me dressed up and may he rub his cock against mine and as his and my cocks played together I felt John slip. She let go again, and the next thing I felt was her finger on my tailbone. Slowly it started moving south, and just before it reached my hole it stopped and pulled away. Then I felt the slow drip of lube into my crack just above the hole, and then the finger came back, spreading the liquid closer and closer to the pucker. Finally the finger came to rest, and then began to massage the hole. “Wow,” I said. “That feels good.” She kept this up for a minute or two, and then I felt her adding a bit more lube. The finger stopped in the middle of the pucker, and she began to push. The pucker opened slightly, and the tip of her finger went in. I drew a sharp breath. “Relax,” she said. It wasn’t easy, but I did. She pushed a little farther. It was hard not to tense up, but by breathing deeply (thank goodness for yoga classes) I was able to stay relaxed. Her finger slid in about halfway, paused, and when I had relaxed fully it went home. “Lord,” I said. “Does it hurt?” she asked. “A.
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