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I should have listened to my friends when they said that an English degree wouldn't be worth the paper it was printed on. Instead, I spent 4 years studying Medieval Romance Literature and wound up walking out of the ivy walled buildings of my university and straight into unemployment. After spending 8 months pounding the pavement, constantly downgrading the level of position I was willing to accept, I finally accepted a job teaching English to foreign students. They come here to Canada for the immersive experience of learning the language, being forced to use it outside of the classroom in their every day dealings with the outside world. Some of them are students taking courses at university, but some of them only take the English language course and spend the rest of their time as tourists. It's not a great job, but it pays the bills and allows me a little extra money left over from time to time for a treat for myself. When I have a couple hundred dollars saved up, I'll go and cruise down to "Tranny Alley," the street where the transsexual prostitutes work. It was the start of the month and I was flush with cash, having just been paid. After paying my rent, I went out with some friends to a pub for a night out. It was a good night, but once last call came around I felt in my pocket. I still had $180 and was feeling a little randy. So after saying goodbye to my friends, instead of walking towards my house, I walked from the pub we were at towards Tranny Alley. I was walking east along the street approaching the area where the girls usually work. I looked at my watch. It was almost 2:30 am, and I was starting to think that this wasn't a great idea, seeing as I had a 9:00 am class the next morning. As I walked along, still about 30 feet away from the block where the girls usually were, I saw her cross the street from the North to the South side of the street. From a distance she looked very nice, with a slim figure. As I continued walking along, she was walking in front of me at a slower pace, which provided me both the opportunity to catch up to her and to check out her ass as she walked. When I had closed the gap to about 20 feet, she turned and faced the street. I continued to walk towards her, and got a better look at her. She was white with black hair. She was wearing a pair of heels, a short electric blue mini skirt and a black top that exposed most of her mid-riff and the space between her breasts. On her hands she had lacey, black gloves. She appeared to start to turn and walk away from me, but then saw me, and instead turned to face me. I approached her, and started to get close. I could see her smiling, and I am a sucker for a pretty smile. I was hooked. She was still some distance from me, but as I approached I could see the look on her face change. Her smile disappeared, and she turned to walk away. This sometimes happens to me, I think mainly because I am a potential client without a car. But the fact that she had been looking at me and making eye contact with me prior to me getting close made me think it might be something else. "Hey," I called out, "wait a moment, please." She stopped and looked down. I approached her and walked around to face her. She was still looking down, so I couldn't quite see the face, but I did look at her body. She obviously had fake boobs and her black hair was a wig, but her flat exposed stomach had me hooked. "Hello there," I said. "Aren't you going to look at me?" She looked up, and I saw her very feminine face, and had obviously done a lot of work on making sure her makeup and hair was just right. I looked into her eyes, and saw that she had an expression of trepidation or fear. It took me a moment to figure out why. Beneath the makeup, I recognized that she was one of my students, a Venezuelan named Carlos. Carlos, in his early twenties, was short and slight, about 5 foot 7 and maybe 120 pounds. In class, I had always thought he didn't seem very masculine, but I had no idea that he could look so feminine. I had no idea the transformation that Carlos to make. I wasn't sure what to do next, and neither, it appeared, was the woman in front of me. Should I walk away? Should I tell Carlos I know who he is? Should I proceed like I have no idea? I was trying to figure out how to decide my next move as we both stood there in silence, when I felt my cock rising in my pants. It was apparent what my cock wanted to do, and that was to get to know this beautiful Latina woman in front of me. "You are a very pretty woman," I said, figuring a compliment might help ease the tension. "I am a lucky man to have met up with you tonight. Can I ask your name?" "My name is Carmen," she said, still looking unsure of the situation. "Hello Carmen, my name is Daniel. How are you doing tonight?" Carmen shifted her feet warily, and replied, "I am fine. It is a nice night to be outside. The weather is perfect, not too hot, not too cold." It was a weird conversation to be having with a transvestite prostitute at 2:30 in the morning, but I still think neither of us were sure of the protocol. "Your English is very good. You must have an excellent teacher," I said, winking. This seemed to cut the tension completely, and Carmen laughed. "I do have a good teacher, and he is very cute too," she replied. I put my arm around her waist and rested it against her bare back. I pulled her closer to me, so we could talk in whispers. I whispered to her, "So, Carmen, you know why I am walking down this street tonight, right?" She nodded, and I continued, "and I think I know why you are out here standing on this street tonight. I was hoping that perhaps we could spend some time together." Carmen looked up at me and smiled. "What do you want to do?" she asked. "I want to fuck you," I said. "Usually I charge $100 for that," she said, "but I would be willing to charge less for some private English lessons." "I can do that. What were you thinking the 'discount' would be?" I asked. She looked at me confused, apparently my turn of phrase not familiar to her. She could use some more work on her English, apparently. "I mean to say, how much do you want to be paid tonight?" "How many English lessons can you give me?" she asked. "As many as you want, as long as you are dressed as pretty as this," I said, looking up and down her tight body. "Then we will fuck tonight for free, and tomorrow you will teach me more English," she said, and took my hand. She led me down the driveway between two buildings, and we walked hand-in-hand along a driveway entrance to a condo, and then onto a dark path between the buildings. As we walked, I looked her over again. Her skirt had an elastic waist, and she had pulled it down so the top of her butt cheeks and her crack was showing. I love asses, and so already I was getting hard. We approached a dark area with some trees and a small brick hut, probably a utility shack or emergency exit from the underground garage. She pulled me into the dark area, turned to face the brick wall, and pulled her skirt down to expose her beautiful small ass. She kept her skirt pulled up in the front, hiding her penis. I undid my shirt and pants, and pulled my pants and underwear down. Carmen grabbed my cock, and guided it right to her asshole without me donning a condom or her applying any lube. I pushed inside her. It was tight at first, and my cock wasn't completely hard so it took a few thrusts, but soon I was rock hard and deep inside her ass. I pumped in her, as she was spread-eagle against the brick wall. I reached down and pushed her skirt lower in the front so I could feel her cock and balls. They were soft, but as I played with them they started to grow a little. "I want to kiss you," I said. With that, she flung her head around and pressed her mouth against mine, opening wide and shoving her tongue in my mouth. I continued to press deep inside her as our tongue wrestled with each other. I had to shift around a few times to try and get a decent position to really get inside her. We fucked for a couple of minutes, but I wasn't sure I could cum. I pulled out, and she asked if I came. "No, suck me," I said, stroking my cock. "No baby, you said you wanted to fuck me. Fuck me." I wasn't sure if she didn't want to do ass-to-mouth or she just wanted to get fucked, but I decided I would do what she wanted. I got ready to go into her again, but before I did she spit on her hand, and then lubed up her ass with the spit. I slid into her easily this time, and with the lube from her spit, I was able to really get some good pumping action going. "Come for me. Come for me," she repeated as she gripped the wall in front of her. I pumped furiously and soon was about to come. "I'm going to come," I said, giving her fair warning in case she wanted me to pull out. She made no move for me to stop, so I continued and shot my load up into her. I pulled out, and other than some slickness from the spit and my come, my cock was clean. She pulled back up her skirt, and I did up my pants and shirt. I pulled her close to me and kissed her. We quickly went our separate ways. She wanted to work a little more, and I had to get home to get some sleep. Carlos didn't have a class in the morning, but did have an afternoon class. After class, he approached the front of the room after all the other students had left. Carlos lives with a few other students in a shared house, so we arranged to meet at my place at 6 o'clock. When Carmen appeared at my door that evening, any thoughts of teaching English fled both our heads, and we were soon naked on my bed. If this is how all our sessions go, I'm not sure Carlos will ever get any better at English. But with Carmen naked by my side, I couldn't be happier. You can read more of my stories here: http://www.literotica.com/stories/memberpage.php?uid=872373&page=submissions
