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Alex and I. from friend to loverThe year was 1996, I was 36 yrs old, I was newly divorced and living on my own in a nice suburban apartment. Had been dressing for a few years and playing on the weekends, when time allowed. My preference at that time was for other gurls, but would not reject a nice gentleman if I found him attractive and appealing. But, I’m getting ahead of myself here. With the chat rooms geared toward the cd/tv scene plentiful, finding partners for a fun time was not hard at all. I was working 50 to 60 hours a week, so playtime during the week was nearly impossible.I worked as a truck driver during the week, making local deliveries to various companies and retail stores, and make a lot of casual friendships with people that I would encounter on my route. This one particular guy Alex (name changed) that worked at a company I was delivering to regularly was very friendly and we would always strike up a conversation, talk about personal issues and stuff. He was about 10-12 yrs younger than me, tall and slim, very nice looking man that nearly any woman would want. He was also recently divorced and our talks began to center on how we would find women and get laid. I told him how I would get laid nearly every weekend, altho I didn’t reveal that I was the girl and was having sex with men. He seemed amazed at my prowess, esp since as a guy I was older and wasn’t as handsome as he was. He would ask my secret, and I was vague and just said I would meet them online. He expressed that he hadn’t had any pussy in over 2 months and was desperate. So desperate that even a shemale would be appealing at this point. Wow! I thought, there was the perfect opening, I would love to have Alex in my bed. I was like, “Really? A shemale”? And he laughed and said, “Yeah, I’m that desperate for sex. As long as she looks sexy and I don’t have to touch her down there”. So I asked, “ What about a transvestite or cross dresser”? He replied, “Maybe if she was hot looking”. I began to wonder if I was hot enough for him when I’m dressed up. He knew me as a blue collar, jeans and T shirt type of guy, how would I approach him with this. A couple of more weeks passed and I would ask him how his search was going, and if he had any luck with the shemale of his dreams. We laughed about that. Then one Monday after a very exciting weekend, I was really horny and Alex was wearing a tight pair of jeans and I kept stealing glances at his crotch every chance I could get, without being caught staring. I asked if he had any luck over the weekend. He hadn’t. I decided to go for it and told him I knew of this cross dresser that might be interested if he was. He wanted to know how I knew her, I said she was distant family. Was she hot and sexy? I told him I would call her that night and see if she’d be interested, was he serious about meeting such a girl? He said he was a little nervous, but anxious and very serious if she was able to get his rocks off. I knew the answer to that, but didn’t reveal anything. I had taken a couple of photos of myself where my wig covered most of my face and was dressed in a tight mini skirt, low cut top, stockings and 5” high heels and showed them to Alex, hoping he wouldn’t recognize the girl in the photos as being me. He seemed very interested and started asking all kinds of questions, like what is she into, does she have real tits, will she blow me, do I have to kiss her or touch her. I don’t think I can kiss a guy in a dress, he said. I wish I was dressed at that moment, I just wanted to drop to my knees and pull his cock out and suck it. I told Alex, “I will give her a call tonight tunceli escort after I get home and see if she might be interested”. I saw Alex again on Wednesday and said I had talked to her, she goes by the name Lisa and she wants you to call her to talk. I gave him my home number and said, “call her after 8 at night, she seemed really interested”. I was home at the computer that night, talking to a couple of guys, trying to make plans for Sat night when the phone rang about 9 pm. I thought it was Alex calling, so I softened my voice and tried to sound feminine so he wouldn’t recognize my voice, picked up the receiver and said, “hellooo”. It turned out it was my ex wife, busting my balls about one thing after another. I cut it as short as I could, telling her I was expecting another call. Alex didn’t call that night and I didn’t see him the next day, but he did call me the next night. “hellooo” “Is this Lisa?” “Yes this is Lisa”. “Um hi, I got your number from Larry, my name is Alex”. “I tried to soften my voice even more, not wanting to give myself away as who I really was. “Hi Alex, Larry told me about you and I’ve been expecting your call”.We exchanged the usual pleasantries of how you were etc, and I asked him to describe himself, altho I already knew what he looked like. He replied with, “I’m 27 yrs old, 6’1”, 180 lbs, dirty blonde hair, blue eyes and 8 inches hung and I like to wear panties if that’s ok”. Wow, I thought to myself, I didn’t know he had such a nice cock, I wanted Alex even more than before now. “what do you like to do Alex, have you been with T girls or men before?” “I had another guy blow me one time” he replied. I had to ask, “did you blow him too”. “No, but I jerked him off”. Then he asked what I liked. I told him I like being treated as a girl, want to be made to feel like a girl when with a guy, I like being kissed, caressed, touched, told him I was very oral. He then asked if I like to fuck. “with the right guy that can take it slow yes”. We talked for about an hour and I helped him get off over the phone and we made arrangements for him to visit me on Sat night at 8 pm. I told him to call me Sat afternoon to confirm. I saw Alex again on Friday when I made a delivery and asked if he called Lisa yet. “No, I haven’t had the chance yet” he lied. Oh ok, I replied and began to wonder if he would actually show up when the time came. On Sat morning I went to the liquor store and got some wine and some beer, did my grocery shopping for the week and then cleaned up my apartment. In the afternoon I took a short nap, relaxed in a long hot bubble bath, since it softens my skin, and shaved entirely from head to toe. I painted my toenails and then started on my makeup with foundation, powder, blusher, eye shadow, false eyelashes, mascara, red lip liner followed by bright red lipstick. Cocksucking red, as I like to call it. I chose a black lace trimmed thong and matching bra, stuffed the bra with my silicone falsies, a nice low cut black top, tight red mini skirt, black thigh high stockings and my black 5 inch cfm heels. I spritzed perfume on key parts of my body and neck, followed by my new long blonde wig. I then applied long red fingernails and stopped to admire myself in the mirror. I saw a gorgeous sexy woman staring back at me. I put a shemale vhs tape in the machine, dimmed the lights and lit some candles. I was totally ready for my exciting date and it was only 7 pm. I sat down at the computer and found a guy to meet should Alex not show up. I was getting turned on chatting with him as we talked about what we both like. He wanted uşak escort to come over right away, but I told him I was expecting someone already. He wanted to join in, but knowing Alex would be nervous I declined that offer for another time. He said if the guy doesn’t show he would be there in a heartbeat. It was now 7:55 and I was excited. Then it was 8 pm, no Alex. 8:10 and still no Alex. 8:20, I heard a car door and peeked thru the closed curtains and there was Alex, walking to my door wearing those tight jeans I admired him in. He knocked lightly, I looked thru the peephole and then opened the door slowly. I had my wig partly covering my face, softened my voice as I greeted him and invited him in. He seemed nervous, which is understandable and I offered him a drink. Then I clicked on the shemale video and with the light from the screen it lit up the room. He exclaimed, “Larry”? My secret was out, what would I do now, I thought. Would he bolt for the door? “Yes, but I prefer Lisa when dressed like this”. “Oh my God” he said, “I had a feeling when we talked on the phone”. “Damn, you look hot”. “Thanks” I said and sat down beside him and crossed my legs. He was full of questions, how long have I been dressing, (10 yrs) did my wife know when I was still married (yes, that’s why Im divorced). “So this is how you’re getting laid almost every week”? Yes. When we talked on the phone I described how I act with first timers. I will not make the first move, I will excuse myself to powder my nose and if my date is not pleased with my appearance or is too nervous to continue, that is his chance to leave with no hard feelings. If they are still there when I return I will sit beside them and not make the first move. If they want to play, just caress me or my legs in some way, that will be my signal. So I went to the bathroom to powder my nose and gave Alex time to decide. I didn’t hear the door so I came back to the living room and he wasn’t there. I thought he had left. It turns out he was in the kitchen making another drink and pouring a shot from my liquor bottle. I walked beside him and asked him to refresh my drink. “This is gonna be weird tonight, since I already know you” he said. I asked if he wanted to leave. “No, lets see how it goes”. We sat beside each other on the couch, watching this hot shemale riding this big cock. Alex didn’t make any move for the longest time, and I began to wonder if I would even get any cock tonight. I got up to fix more drinks and could see in the living room mirror him adjusting his crotch as my back was to him. I returned with the drinks and sat even closer to him now and placed my hand on his knee. “Larry, er, Lisa, you do have sexy legs” and with that he ran his hand up and down my stockings. The moment had finally arrived and I was so excited!!! I slid my hand up his leg and to his crotch. I could feel his hardness thru those tight jeans, traced my long fingernails along the shaft, gave it a squeeze. I fumbled with his belt and zipper, with these long fingernails it wasn’t easy and he helped me by opening his pants and I reached in to discover he was wearing a silky pair of panties. I started to rub his cock thru the panties and it dripped some precum that glistened and leaked thru on the silky material. I wiped it and brought it to my lips, savoring the sweetness of it. Alex stood up and removed his pants and shirt and I saw the most glorious set of 6 pack abs. What a perfect man I thought to myself. I dropped to my knees as he was still standing and pulled his panties down and there was the hottest 8 inch cock I had ever yalova escort seen. It stuck straight out, was not overly thick, trimmed nicely. I could contain myself no longer and leaned in to wrap my red cocksucking lips around it. He moaned as I slowly took it all the way down my throat. My clitty was so swollen in my tight thong and dripping its own precum. Alex grabbed the back of my head and began to methodically fuck my mouth, which is such a huge turn on for me. Without moving my mouth from his cock he sat down on the couch. He pulled me off of his cock and pulled me up onto the couch beside him. He ran his hands up my legs and under my skirt, felt my hardness thru my thong, then pulled the elastic band aside and pulled my hard clit free and started to stroke me. I had a hold of his cock as well, I closed my eyes and tilted my head back and let out a moan, this was so heavenly. To my astonishment, I then felt his lips meet mine and his tongue in my mouth, kissing me deeply like the woman I felt I was at that very moment. To my further surprise, he broke our kiss and said, “I always wanted to try this” leaned over and took my 6 inch throbbing clit into his mouth. He sucked me up and down for a few minutes and at one point I thought I would explode. I suggested we go to the bedroom and as I led the way, he placed a hand on my ass and squeezed. I had him lie on the bed and I turned around and got on top and we locked into a hot 69, sucking each other. He played with and then began to finger my ass. I sucked his cock up and down like mad and then I could not hold back anymore and told him I was about to cum. He just kept on sucking me and shoved his finger deeper into my ass. I started pumping his mouth, riding his finger and then let out a gusher of hot cum deep into his throat. He kept right on sucking until I went soft. All the while I kept on sucking him and thought he would never cum. Finally he stopped me and I lied down next to him. He kissed me again, caressing my legs and body. “Can I fuck you Lisa?” I got up and turned around on all 4’s and he positioned himself behind me. I told him to go slow til I got used to it. I felt his cock head at my love hole, what a glorious feeling. I slowly pushed back against it as he pushed forward and in no time he was buried balls deep into my pussy. He grabbed my hips and began pumping in and out of my tight hole for awhile, then pulled out and flipped me over, lifted my legs and slid his cock back inside of me. I wrapped my legs around his back and he liked running his hands up and down my legs as he pounded me with every bit of his 8 inch cock. His breathing became heavier, he was moaning and his crescendo was building. “where do you want it Lisa?” I replied, “anywhere you want”. He pulled his cock out, got up and straddled my chest, put his cock in my eager mouth and began pumping my face. Then he pulled out and started stroking it, and shot gob after delicious gob all over my face and into my mouth. He collapsed on the bed next to me as I wiped his cum from my face and into my mouth. “Lisa, that was the best sex I have ever had, I didn’t want it to end”. We got up to clean up and I offered him another drink, but he declined, saying he was probably already too drunk to drive home. “Can I sober up for an hour before I leave?” I told him he didn’t have to leave tonight, he could stay with me. I awoke in the morning with Alex spooning with me and his hard cock pressing against me. After another round and him cumming in my ass this time, I made breakfast and we talked. We promised each other that no one would ever learn of what happened here. As he was leaving, he kissed me deeply again and said he hoped we can do this again. I promised him that we could anytime he wanted, but only when Im dressed up. I saw him every weekend after that for about 6 months until he found a girlfriend. What a lucky woman she must be……

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