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Even though he looked good, he was still a male and usually not my first choice for a Saturday evening in this seedy bar. I was also wondering how much I was daring to go with this guy. "Aren't you having fun? I saw you dancing." I dared to pull him a little closer, wondering how much I would get away with, teasing him as if he was a real woman. I am working on it." Sam's reply feigned gratitude, not even bothering to remove my hand from his waist. "You are doing a great job with the voice, Samantha. Sliding my hand around the brunette's waist, I said to him. "Bartender, a couple more rum and cokes, please." A soft voice cooed to the burly but affable man behind the bar. I turned my attention back to the game, nursing a couple beers before I felt a nudge. They probably did but liquor changes people's judgment. Among the patrons, 'Samantha' could be seen in tow with his girlfriend and two guys! I chuckled as I watched them dance for a little while, wondering if they knew she was a he. I watched their banter for a couple moments before returning my attention to the game playing on the television behind the bar.Ī short time later, I heard the music play and several couples were cheerily moving to the dance floor a short distance from the bar. I got a huge kick from the whole experience and watched as he handed his girl the drink and sat at the table. "Samantha," he said dejectedly before quickly walking to his girlfriend. "Hey." I called to him before he scampered off, "What is your name?" The drinks arrived and he hurriedly grabbed them. Just soften your voice." I said, evening my voice to calm him. "No way! Great lipstick and ass, pretty face with all that make up, and you have to admit, you do look hot.
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"You are kidding me, right?" He looked at me, shocked by my comment. I might not have known you were a guy if you did not talk." Your make-up really helps you look feminine. "Maybe that will be enough to sate her appetite." I smiled at him. "I can't believe you just squeezed my ass!" He said quietly but still shaken by the experience. "That wasn't so bad, was it?" I asked innocently. "That is enough," he said, swatting my hand aside. She is getting a huge kick out of it as the crossdresser eyed me angrily the whole time. I see his girlfriend watching as I put my arm around his waist and slide my hand to his ass, squeezing each shapely globe for a few moments. "Oh my god!" He said exasperated, "I can't believe I am about to say this," he replied seemingly resigned to his fate. I will buy your drinks for small recompense. He glared at me, "What do you mean? You know I am a guy, right?" "Well," I said with a wide smile, "Maybe I can be your first experience."
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Hopefully, I won't be too embarrassed or humiliated." He said gloomily. "She wants me to experience what it is like to have men ogling and using me." He looked in her direction, then back at me. You are a lucky guy!" I say to him, patting him on the back. I looked over to see an amused, pretty young woman, about aged 30, smiling at us as we talked. She figured this would teach me a lesson." He said exasperated. "If you must know, my girlfriend caught me cheating on her and she is tired of me making passes at women. It is all good." I said while raising my hands up in surrender.
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He looked at me and almost scowled, "My girlfriend is right over there and I am just trying to get a couple drinks." Your skirt and blouse match perfectly sexy shoes and I love the stockings." I openly admired. I have never done this before." He replied gloomily. "At least you look real good." I smiled at him. "I don't want to talk about it." He replied in a husky voice. "Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks. "Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone.