2 comments/ 33587 views/ 31 favorites Transexual Encounter Ch. 01 By: SluttyValerie I few years ago I had been downsized out of a lucrative executive position with a company I had worked for years, worked my way up through a few promotions until I was too expensive to keep around when things turned sour in the economy. I really liked my work and it afforded me the opportunity to live comfortably, travel and indulge my secret kinky side. On typical business trips, when time lent itself, I would add in an extra day in which I did very little work and transformed myself into my alter ego. I kept it under control and only did this a few times a year while on company business. I also "invented" a few weekend business trips in which I could play unencumbered and use my own personal time vice the company's time. I had slowly over time progressed into a quite passable cross dresser. I have detailed in a couple of stories already posted. My intent was to chronicle the progression, but this story somehow jumped ahead of the list. My ability to find time to write has been an issue that I was unprepared to deal with when I thought out the stories that I intended to write. I have been very athletic and was blessed with a slender build, I ride, run and swim but would not consider myself and true triathlon type as I am just average. I was a runner at first and subsequently used the riding and swimming as a cover to shave my body. I don't have much hair but enough that it would hamper the ability to pass as a CD. I actually have to work at keeping weight on, losing weight is a problem for most everyone but not for me, I wish I could bottle and sell my metabolism. I am 5'11'' and 160 pounds and have become quite good at transforming myself into a virtually passable female, my voice needs work and it is something I don't think I can really change as I only do this part time. I have used the internet sites to find other likeminded individuals, most often I answer postings looking for compatible play partners, on the rare occasion when I post an ad myself and my inbox gets flooded with responses so I know I can attract a lot of attention when the desire arises. I have figured a way to get a sexy tan line in the summer as well. Aside from spending time at the beach, when I run, I run with no shirt and when I finish, I jump in the pool and strip off my running shorts and swim in speedos. Then I will lie out on the steps of the pool and roll the Speedo sides up so it look like I have on a high cut pair of panties and soak up the sun. It gives me a bikini tan line. I have very good quality wigs and silicone breast forms with perky protruding pink nipples. You get the Idea that I can really get guys lined up to come and be my cock sucking panty slaves. When I do post, however, it is for other CDs like me. It never stops the endless onslaught of guys trying to get to see me as the majority of the responses are guys. I am not attracted to guys, even when I am fully dressed, just transsexuals and passable and even semi passable CDs. I can let a non-feminine face slide by if the body is sexy to me. This particular story takes place at a time when I haven't dressed or played for a while and as I stated earlier, I was looking for work. The preamble to this occurred six months before I was laid off, I was traveling and had my special things with me and I was looking to dress and meet someone. I had seen an ad periodically posted by someone who had interested me greatly, but we never connected due to myriad reasons. This time however we were chatting back and forth and it looked promising. She was a transsexual, 5'7'' and very slim with natural budding breasts, probably 34A cup with nice dark nipples and mocha skin. She was not a professional, unusual for real TS. She was a full time female with a real job and was looking for bottoms. She has naturally long hair and a very feminine face, everything about her was attractive to me and completely female even her 8 ½ inch horse cock, thick, cut and perfectly proportioned and symmetrical. Her balls were average in size and did not hang to low off her body. Her pictures were awesome. Her posting read the following: Bring your ass and throat over or pick me up ...fuck you for hours ...I love deep ass n pussy 8.1/2 hung ts you looking for some real fun can host or be picked up... Older guys are a big plus. She was a total top so I told her I was a bottom but also a CD. I sent her some of my hottest pics dressed like a slut. I have a beautiful white smooth tight butt and I sent her my best ass shots in order to entice her into meeting me after seeing my picture, she told me to come over and bring my clothes to dress. We set a time and I hurried to get ready in my hotel. I wanted to be fresh and clean, so I shaved my face very close. I shaved my ass, cock and balls quickly to ensure total smoothness. I am obsessive about cleaning myself out so anal sex is completely clean, and that took some time, the feeling of warm water filling my ass is oddly pleasurable and with the anticipation of what was to come, I was getting hard. I hadn't taken a cock in my ass for a while so I used a couple of dildos to stretch my ass out. First a small one then a much bigger realistic cock with balls. I was turning myself on sliding this big silicone cock in my ass. I couldn't wait to see her. I put on a pair of black lace stockings and a sexy black garter belt with 6 garter straps, three for each leg. Next I put on my black satin waist cinching corset and a see through black lace bra. I had so many pairs of panties I had a hard time deciding, eventually I put on a silky stretchy pair of dark pink panties with a small bow in the front, high cut on the sides to give me more of an hour glass shape. With the waist cincher, my shape was totally feminine. I really wanted to go to her fully dressed but there was no discreet way to leave the hotel as it was 3 in the afternoon. I decided to push things a bit and put on some make up to make the trip more exciting. I just put on some eyeliner to accentuate my eyes. I put on a suit jacket and trousers with no tie. The black lace bra was visible through the white shirt if you looked closely, with the jacket on it was less noticeable, and the thought of the cute little desk clerk noticing my eyeliner and bra sent chills through my body that settled in my crotch. I picked up my bag of gurl things and headed towards the door. Then I decided to push things a bit further. I wanted to be a bit more daring so I put on some lipstick, not too much and a very translucent pink, just enough to make me feel excited but probably not enough to make someone from across the lobby notice, but if there was someone in the elevator, they may notice. Walking down the hallway I was surprised and a bit nervous, it seemed as if the maids were having a convention on my floor and in my hallway. I looked a couple in the eye and smiled and said hello. I don't think they noticed and the trip to the car was uneventful. On the way there I was contemplating slipping my silicone breast forms into my bra, but since I did not know her neighborhood or how to enter her place, it thought better of it and decided against doing so. I arrived at the address and texted her that I was there. It was raining so she did not want to come out. The place was a rather large house that must have been converted to apartments. Hers was on the top floor and there was an entrance on the side. I went up the stairs and knocked, she opened door immediately. I was nervous because there is always the chance that someone is not who they say they are. I was expecting to see the woman in the picture, not some hairy guy in pantyhose...to my relief it was the girl in the picture that answered the door! She was dark skinned, very slender with a very feminine face, she didn't have make up on and looked as if she had just come out of the shower. I came in and we sat on her couch and chatted bit, she asked me how much time I had and I told her all night if need be. She said great, because she needed some time to finish getting ready. She said she had been looking for someone since recently moving here and most of guys wind up not showing up so she didn't want to get all dressed and made up for a no show. She was very sexy and hot without made up, I thought, she is going to be a knock out when she dresses puts on makeup. She made me stand up and turn around to check me out; she was impressed and said she really likes my body type. She then asked me if I understood her ad and what it meant. I said yes. She said are you sure you are OK with that? I said yes. She said tell me what the ad said. I told her that I was here to offer her my ass and throat to do as she pleases, that I was going to change my clothes and dress like a woman and have her use me as she saw fit. She stood up from the couch and ran her hands up the back of my legs and with both hands and squeezed my ass. She felt the garter belt so I took off my jacket and she put her hands on my chest so I knew she felt the bra. I think at this point having her stand so close to me; she noticed my eyeliner and lipstick. She smiled and said that she was going to have fun with me. I told her that I needed time to get ready too so she showed me to the bedroom and she went to the bathroom. I stripped off my clothes as fast as I could and started to get dressed. She left for the bathroom. I was in heaven. I slipped in the silicone tits and put on a tight clingy black top with black lace around the neck. Tightened the waist cincher a bit snugger and put on a black mini skirt then a pair of Italian 4 inch heels. I quickly put on concealer and foundation and filled out my lips with a red lip liner and put on a darker red lipstick. A bit of blush and some eye shadow and the makeup was complete. A few drops of cologne on my neck and a silver beaded necklace and a silver bracelet. I skipped the earrings and donned the shoulder length brunette wig. I put on a cute white plastic headband across the top of the wig to keep the hair out of my face when I am busy bobbing my head up and down in anticipation of sucking her thick long cock. I had time to primp a bit more so I laid out some of the other clothes I had and did some snooping through her things, she had a small hamper on the floor of her closet that was open so I looked through some of her clothes causally and then went through her hamper and found a black pair of panties, I unrolled them and smelled her essence and musky odor as I inhaled them. They must have been the ones she just had on because they were still damp and pungent. I thought about putting them in my bag but decided against it. I didn't want to tempt fate so I went to the bathroom and told her I was ready. She came out and told me I could wait in the living room while she dressed. I asked her if it was OK if I came in and helped her dress. She said OK and that it was cool as her previous boyfriend only wanted to see her when she was fully dressed. I said to her that he must have been nuts not to want to be around her as much as possible. She smiled and grabbed my hand and led me back to the bedroom. She had already put her makeup on in the bathroom and she now looked even better, she told me what to get and where to get it and I handed her the clothes. She said she wanted to get to business so she was only going to put on some sexy lingerie as she didn't want me to look sexier than her. I said that would be impossible. She laughed and told me to turn around and not peek while she dressed. I heard the towel drop to the floor and a minute or two later she came up behind me and ran her hands up the back of my legs and lifted my skirt and she grabbed my ass. I wiggled my ass and moaned like a school girl, she said was going to have fun with me. She pulled my skirt down to my ankles and told me it was sexy but would just get in the way. She pulled my panties down and marveled at the smoothness of my ass. I turned around to drink in the sight of her. More than I could ever have imagined. I kissed her neck and looked at her for approval to continue, she gave me look that said OK and worked my way down her neck to her tits. She had on a black bustier with gold trim and a matching set of panties. I pulled down the mesh fabric that held her breasts and started to suck on her black protruding nipples. No implants, just a mouthful of gorgeous mocha colored home grown flesh. I told her that natural tits were always better than gigantic rock hard implants, she said she eventually wanted implants and I said whatever you do don't get them too big. She agreed and I slid my tongue down to her panties. When she turned around initially, I glanced down at her crotch, not trying to make it too obvious, she looked completely flat, no bulge, I thought that maybe the picture was of someone else's cock. Now with my face right in her crotch, I knew that she must have really done a good job tucking herself because now there was a massive bulge staring me right in the face, one inch away from my lips. I could feel the heat emanating through the sheer black panties. I pressed my lips to her bulge and made contact with the panties and just kept pressing my face into the bulge, I reached around her with both hands and pushed on her ass moving her body towards my lips and I opened my mouth and put some of the panties and bulge in my mouth and rocked my head back and forth. She grabbed the back of my head and pushed it harder towards her body. I moaned and opened wider, licking the panties while moaning a lower guttural moan that I hoped would vibrate and make her harder. I pulled back and drew a few breaths and looked up at her as she looked down at me. I smiled an pulled back her panties, by now her cock was about half erect and was just beautiful, smooth, hairless, big dark cock...right in my face. I took it in my hand and lifted it up, it was heavy and solid and I thought to myself; how could someone this slender and slight be carrying around this huge cock? I thought that if it got any bigger I might not be able to handle it. I opened my mouth and slid my lips over the head and sucked on the head only for a minute or two. I stroked the length of her shaft gently with one hand and bobbed up and down on the head. Fortunately she grew in length and only a bit more in girth. As she stood in front of me, while kneeling in front of her, I made my way down the length of her penis and sucked her balls in my mouth, smooth no hair or stubble, just the way I like it. Her balls were bigger than the pictures indicated. It was all I could do to get them both in my mouth. I slid my tongue up to the head again and was now determined to see if I could get this fucking monster in my mouth and throat. I started with the head and with each pass went a bit further down the length of her womanhood. In no time the head was hitting the back of my throat and I had a good 3 or 4 inches of cock to go. I came up for air and took a few breaths. I looked up at her and smiled, she sensed I needed a rest and she put her red nail polished finger in my mouth and I sucked it, then two fingers, then three. I knew where this was going so I backed off her fingers and looked back up at her, she smiled and said I was a good girl. Without hands I opened my mouth and sucked in the softening head of her cock and pushed my way down the length of her shaft until my nose was pressed up against the small patch of curly hair. I pressed further against her pelvis as if to say, here I made it all the way; like spiking the ball in the end zone. I could feel her getting harder and my celebration was short lived. I pulled back up quickly and took a deep breath. Her cock was engorged and hard again, she told me to keep going and show her what I had. This time was going to be different. Before I put my mouth back on her, she grabbed my hand and put it around the shaft of her wet cock and motioned to me with her hand. I stroked her cock in a rhythmic manner and it turned rock hard and stood straight up! I felt her hand on the back of my head and heard her say OK "get to it bitch." I opened wide and with one motion down took half of the length into my mouth. With half of this slim girl's cock in my mouth, she was already in my throat, my God I thought, what the fuck am I going to do? I pulled up to where the head was just in my mouth and sucked in some air and swallowed a mouthful of saliva and relaxed my mouth and throat as best I could and slid my way down again, this time making it three quarters the way down, no doubt now that the head of her cock was no longer in my mouth, it was in my throat. I held it for three seconds which seemed like an eternity. I pulled out again and drew a few breaths. This time she grabbed her own cock and stroked it furiously, I thought she was going to spray my face with cum, I was wrong, I didn't know it at the time but this chick was going to display an amazing feat of self-control and stamina and the harder I tried to make her cum the more she was determined to not release her hot, thick, syrup unless she wanted to do it. After stroking herself rock hard, she put two fingers in my mouth and opened her fingers forcing my mouth open and put my mouth over the head of her cock and said to me "all the way this time girlfriend." It was now or never, I opened wide and went back to the three quarters point that I previously reached, again I could feel her cock in my throat and then without her hand on my head I pushed my way all the way down her cock until I was again pressing my nose against her pelvis. This time it was different, her cock was rock hard and this fucking behemoth was no doubt where no cock had ever been. I held it until I started to gag, I was going to pull out and I felt both her hands on my head forcing my face even tighter to her body, at the same time she started thrusting her hips, she let out a moan and continued to moan. She released my head and I came off her and collapsed to the floor sucking air as fast as I could. She knelt on the floor and stroked my hair away from my face and said I was a good girl and I was her best cocksucker ever. She said I deserved a rest. We sat on the bed and drank some water and I wiped my face and put on some more lipstick. I told her I loved her cock and asked her if I could suck on her tits while I rested a bit. She was on her back on the bed and I was next to her, I rolled over and started sucking on her tits, pinching the nipple that wasn't in my mouth between my fingers. A bit harder each time until I sensed her limit of how hard I could pinch. I like mine pinched really hard and I told her that hoping she would do it later to me. I was trying to suck milk from her breasts the way an infant sucks a breast. I told her I wanted her milk; she picked up on it and said I would be getting some milk later if I was a good girl. I told her I would be for her. We drank a bottle of water each and I had my hands all over her as we sat on the bed. At this point I had my panties off and she was exploring my ass. She made me stand up while she sat on the edge of the bed. She asked me how I kept my ass so smooth and I told her I shaved right before I came over. I told he about my cleaning out regimen and she was surprised at the length I went to; about 10 bags of waters worth. She stuck her finer in my ass to check and she pulled it out clean as a whistle. The she lubed up two fingers and stuck them in and twisted and thrust them in and out and again they came out clean. She wiped the lube off my ass with a warm wash cloth she got from the bathroom. Then completely by surprise she bent me over, she was still sitting on the edge of the bed, she stuck her tongue in my ass and just kept at it. I was moaning like a slut the whole time. She sucked on my ass and jammed her tongue in and out like she was fucking me. Transexual Encounter Ch. 01 Finally she stopped and said to me " I guess you liked that?" I just moaned yes, yes, yes to her. She said I really want to fuck you now. I said to her that my ass was hers and she could fuck it anytime she wanted. We went over to the couch next to the bed and she sat down and I bent over in front of her and took her semi erect cock in my mouth and sucked her until she was hard. She slipped on a magnum condom and turned me around; I put my hands on the bed and bent over. She stood up and squeezed some lube on my ass. Where she had gotten the lube from was a mystery to me. I felt the head of her cock press against my ass and I told her if it was OK with her that I'd like to back onto her cock and if she could just hold steady that I would tell her when I was ready for her to take control of my ass. Thank God she agreed with me; stories of how gurls who have miraculously never had a cock in their ass and take a big thick cock in one stroke are not believable. My story here is absolutely true. I slowly backed onto her cock and pulled out once or twice for a bit more lube. I finally had her cock all the way in my ass and could feel her thighs pressing against mine. I told her to push harder all the way in. She grabbed my hips and pulled me harder towards her. She was now in me as far as she could go; I could feel her balls pressing against my perineum. I said hold that there for a minute. She kept the pressure up and I could feel my ass expanding and stretching to accommodate this huge fucking hard cock. I moaned like a bitch to her over and over, "I love your fucking hard cock in my ass." I said I am ready for you to fuck me, please start slow. She started fucking me, gradually picking up the pace. A few times I asked for more lube and to slow down a bit. Eventually I was opened up and lubed up and I actually started telling her I could take it harder, each time she picked up the pace and intensity of the thrusts. We eventually moved to the bed, me on my knees doggie style and her behind my thrusting like a machine that would not tire. She started with both of her legs between mine but switched off by putting one leg outside of mine and drilling my ass at an angle, she did that several times left and right. There was no stopping this woman, she never let up but for a couple times to take a sip of water, I was a sweaty mess and she gave me drinks out of her water bottle too, in my predicament I was still thinking about how her lips had been on the bottle and now mine are mixing with hers. The pounding and slamming of my ass continued on with no end in sight. I could not believe she was still going at it. My knees were tiring from the doggie position as was the rest of my body. I tried to lay flat on the bed and have her lay on top of me. I like the weight of her body on mine as she pounds my ass with her cock but she kept pulling me up so I resigned myself to taking it doggie style until she was finished. Periodically I stroked my cock until it was hard, I didn't want to cum so I was careful not to overdo it. She just kept on ramming my ass over and over, she was rather quiet during all of this and then she started to talk about how she wanted to bareback me and shoot a load of cum in my ass. I thought to myself at this point she probably wore out the condom away anyway. I hoped it was idle chatter as I was still leery of disease and didn't say OK to it. I told her she could fuck me as hard as she wanted and she replied that if I would probably regret it if she turned herself loose on me. I really didn't think anyone could fuck any harder then what she was doing to me right now so I said can you actually go harder than this? She laughed and said I was not ready yet for her hardest. Apparently she could, I shuddered to think what that would be like. She started talking again how I was going to be a kept woman and that she was going to own my ass and throat. The more she talked the hotter I got. When she said something hot I responded by telling her I was her bitch and my ass was her property. She liked that because I always got an extra-long deep thrust that she held tight to my ass and pulled my hips towards her and then she held her throbbing cock at the hilt for a second or two. She told me she was close to coming and she wanted me to come at the same time, I told her if she grabs my nipples while she thrusts into me and pinches and twists my nipples that I will cum like a whore. She unhooked my bra and the silicone tits fell to the bed and she reached around and checked my cock to see if it was hard, I pulled my hand away and she grabbed my cock and stroked it while her other hand pinched my nipples, all the while she was still pounding and thrusting away, unbelievable the stamina on this woman. I went back to stroking my cock and she was pinching both my nipples and I told her at this point I could cum on demand and she should just tell me when she was about to cum. She picked up the pace which was amazing in and of itself. Her long thick cock had been pounding my ass for at least 40 minutes nonstop since we got on the bed, total time must have been an hour of her 8 ½ thick monster fucking me like I was her prison bitch, which I was. I told her to start spanking my ass when she started to cum and I would make sure I came at the same time. I begged her to give my nipples a few good long hard pinches before she started to spank me. She said she liked that idea and that she would start spanking my ass now and when she stopped spanking me she would be coming. Little did I know that she was going to turn my ass red before she allowed herself to cum. She was a machine, but having been spanked and done some spanking, I knew that a good hard hand spanking can take its toll on the spankers hand almost as much as the spankee's ass. My ass was being drilled to no end and the cheeks were flush from being spanked but it was finally coming to an end. She relented on the spanking and grabbed my hips and stated moaning pulling my ass to her as hard as she could as she lurched forward with each thrust. I stroked my cock furiously as she let out each heavy moan. I started moaning myself and kept repeating to her over and over "your bitch is coming, your bitch is coming" I sprayed cum all over the bed sheet and shuddered as I did so. She pounded away and then rammed her cock in me as far as she could get it and stopped, held it there and we both collapsed onto the mattress. She let out one long guttural moan as the weight of her body lay on top of mine. She whispered in my ear "I came baby, I came in your ass" We lay there with her cock still up my ass as neither one of us could move. Eventually she pulled out and her condom was still on and hadn't broken open. I rolled over and slipped off the condom. Eventually after resting and wiping my dripping ass of lube, I snuggled up to her soft cock and sucked it into my mouth I sucked the sticky cum off her cock, I rolled over between her legs, she was on her back with the pillows behind her head sitting up and resting and I had my mouth on her cock sucking her cock like a baby sucking a bottle, cleaning her cum with my mouth. I kept at it which after all I had been through even surprised me. I was much easier sucking this soft monster, I reached up with both hands and fingered her nipples, she surprised me, I thought she was just going to lie back and rest while I snacked on her cock a bit,. She casually said to me "suck my balls like you did before." I sucked both balls in my mouth and put some suction on them and then backed my head away from her gently pulling her balls tugging them away from her body. I repeated that several times and I noticed she was stroking her cock with one hand and twisting a nipple with other. I moved her legs wider and had her bend her knees so her feet were flat on the bed and ran my finger around the dark bud of her ass. She scooted her ass up a little higher indicating that what I was doing was OK with her. I kept sucking her balls and inching my finger into her ass. She continued to stroke her cock, that fucker was getting hard again, I the thought ran through my mind that I started something I may have wished I didn't start. We kept at it and I was grinding my cock into the sheets and it was hard again too. She pushed my head away from her balls and said to me that it was time for me to rim her. I slipped my finger out of her ass and took the tip of my tongue and rimmed her ass, flicking the tip of my tongue over the tight muscle. I licked, sucked and rammed it into her over and over as I dry humped the bed. Her cock was back at full mast and totally erect. I was actually afraid that she would fuck my sore ass again. I heard the words "suck your girlfriends cock." I complied and this thick juicy shaft was once again in my mouth. She then said something that scared the crap out of me. She said the cock sucking I did before was just a warm up and that if I remember that I agreed to let her use my ass and throat and that she hadn't used my throat yet. I was terrified and didn't know if I could go through with it. We switched positions , I was on my back and she was straddling my face with her cock right in my face. I said to her please let me rim your ass a bit to stall her but she just pushed that big fucking throbbing hot cock in my mouth. She looked so beautiful, her flat stomach and perky mocha tits with dark nipples, my mouth full of her meaty cock. I had no choice anyway. I sucked and sucked like my life depended on it. She pushed her way down my throat, I was deep throating her now with a bit less trouble but still barely, I was still gagging and have trouble but she seemed pleased. She was ramming away when she said I want to cum in your mouth, she looked me in the eyes, I couldn't speak with a giant mouthful of cock so I just nodded up and down, her big cock moving up and down with my head as I nodded the OK signal that I was on board to receive a mouthful of cum. When I cleaned her cock of her own cum, it tasted great, sweet and sticky. I figured she blew a load into the condom already so how much could she shoot a second time? I was about to find out. It still amazed me that this petite little slender 5'7'' 125 pound woman was sporting this huge hunk of meat between her legs. She pulled out of me and I gasped for air and wiped the slobber off my face. Like a machine on full, she stroked away at her cock, getting closer and closer, I was jerking myself off at the same time but couldn't time it with her, I grimaced and shot my load, being under her and between her legs my cum sprayed onto her ass and small of her back, she felt it and said that it was not polite to cum without permission. I couldn't speak, I think the cum on her back was enough to put her over the top. She placed the tip of her cock on my outstretched tongue just like the porno movies do it. A spurt of hot sticky cum shot out of the tip and I caught it with my tongue, then another bigger spurt went right in my mouth and hit the back of my mouth, then another just as big as the second, unbelievably the fourth spurt was bigger than the second and third. I caught all of them and I could feel the cum pooling in the bottom of my mouth, my mouth was actually filling with cum. Another spurt and it was less volume finally. I opened wide and moved in toward the spurting cock so the tip was in my mouth, no chance of missing any cum. I closed my mouth around her cock and started sucking; surprisingly she shot a few more spurts of cum in my mouth with my lips sealed around the circumference of her womanhood. I held her cock and a mouthful of cum until she pulled out a semi erect softening cock out of my mouth. My mouth was full of sweet sticky cum. I opened to show her and she put two fingers in my mouth and stirred the cum. I closed my mouth instinctively around her fingers and sucked them like I was giving her fingers head. She pulled her fingers out and held my mouth shut and pinched my nose. I wanted to swallow her cum so it was not necessary to do that but I played along and let her think she was forcing me to swallow her sperm. With a couple of big gulps it was down my throat. We both smiled and she said to clean up the mess on her ass and back. I went behind her and licked off all of my cum which wasn't much but I licked and licked until told to stop. We rested on the bed for a while. I was exhausted, totally spent and had a sore ass. She was happy and said that her former boyfriend never even came close to pleasing her like that. I showered and left in my male attire back to my hotel where I rested my sore ass. This would not be my last encounter with her. Transexual Encounter Ch. 02 It had been a while since I had first seen this slim sexy TS, she was so sexy I thought about her quite a bit. My company had laid me off a few months after my encounter with her. I was still comfortable since I saved and had a decent severance package, but I was antsy about getting back to work. I looked around for things that I normally wouldn't have considered. I came across an opportunity to do some temporary consulting work in the field I was well versed in as a 1099 contractor. As I scoured jobs boards, I saw an opportunity that would put me back in my mocha gurl's city for a few days; I had to go meet the people for an interview and proposal. I booked a room not too far from her house in hopes she would be available. I told her about my plans and made arrangements to get in early the day before my meeting. I arranged to meet her. This time I asked her to come to my hotel, she said OK but I would need to pick her up. I told her if she was OK with it, she could spend the night. She said she might but had to figure a few things out. I didn't press her. I picked her up and she came out looking pretty, a skin tight black leotard type pants and a tight shirt with a loose jacket as the weather was nasty cold. I know the size of her thick long cock and I was totally amazed at the fact she had tight pants on and there was no bulge at all. We headed off to my hotel and I mentioned about going out to eat and she said she didn't dress up enough to go out. She said to me "you should have told me about dinner, I would have sent more time getting sexy" I told her she looked fine but she balked and we drove on. On the way she wanted to stop and get some things. I asked her about condoms and lube and she said we needed to pick some up. I went into drug store and picked up a bottle of lube and a dozen Magnum condoms for her. I am waiting on line at the counter and finally get to the register to pay. I am thinking to myself as I checked out, if this cashier only knew that the condoms were for my honey sitting in the car, and that in a short time I would be taking her huge thick cock in my ass. I thought about how cool would it be to just blurt that out to her as I picked up the bag, my cock stirred and started to engorge right there. I chickened out and said nothing and left. Back in the car, I said I wanted to get some beer and asked her what she wanted. She told me that she wanted a bottle of Hennessy. I looked over at her as we came to a red light and I looked down between her legs and I was shocked to see a huge fucking bulge pushing through her black tights. I smiled and said that she must be glad to see me. I could not keep my eyes on the road and was actually glad to be at a red light. I reached over and felt her up through the tented material. I previously had this fucker in my mouth and ass and yet I was still amazed at it. I wanted to bend across the seat and plant my face and lips on it right then and there but the light changed. As we drove to the liquor store I continued to reach over and stoke her meaty bulge. When we got to the liquor store I tried to get her to come in the store with me. I said no one will notice your big hard cock sticking out, we both laughed so hard it was ridiculous. I got out of the car and started to walk to the store, and then I turned around and opened her door and bent over and kissed her on the lips and held my lips against hers and reached down and stroked her cock a few times. I released my lips from her and I could see she was flushed and I had delivered the desired effect on her. I said don't go anywhere and don't do anything I wouldn't do, I'll be back in a couple of minutes. She laughed and said to me. "When we get to the hotel, you are going to pay for making me so fuckin horny; your ass will be mine." I said to her, "it already is." Back in the car and back to the hotel. She was worried about going in together but I told her, it's my room and I can have a guest here if I want and if they don't like it, fuck them! I had a suite with a living room and small kitchenette, she sat on the couch and I put the beer in the fridge and took one out and poured her a drink from her bottle. I brought her the drink and sat next to her. We sipped a bit and chit chatted. I told he there was a Friday's restaurant on the other side of the parking lot literally a hundred feet from the side door of the hotel. She knew what she wanted and so did I. I was going to run across and order the food and come back and we would eat in the room, she said she would put on something sexier. I told her I needed one for the road. I finished my beer and instead of getting a beer, I put my face between her legs as she sat on the couch and I nibbled through the material of her tights, she had re-tucked herself to walk into the hotel. She lifted her ass off the couch to "free willy" so to speak. I moved the coffee table away and knelt on the floor between her legs and pulled her tights down around her ankles. She pulled her panties aside and it popped out in all its glory. God, I never get tired of thinking about it, talking about it and writing about it; that big thick long juicy meaty fucking cock of hers. I opened wide and put my lips around it and bobbed my head up and down on it. It grew immediately in my mouth and was less than a minute and it was fucking huge and so frigging hard, I was jealous of it but also in awe of it and happy that for tonight it would be all mine. I knew from past experience I was not going to make her cum quickly so I knew I had to break it off and go get the food. I was hungry and we had all night. I came up for air and took the tights off her ankles and saw some cute multi colored socks she had on. I took them off her feet and saw some pretty red painted toes. I have an unbelievable foot fetish that she didn't know about yet. So I took her toes in my mouth and sucked each one like it was a little cock. I counted them off one through ten. Then I rubbed her feet on my crotch, and I said, "I guess it was ten for the road." I kissed her once and said I had to go get the food. I headed for the door and she stood up and said to me, "come here for a second." I walked over to her and she said to me that she was really attracted to me and kissed me on the lips. She put her arms around me and we French kissed, intertwining our tongues. I wrapped my arms around her and held her tight to my body and told her that she was the most beautiful person that I was ever with in my life. I told her I'd be back as soon as I could and went to get the food. The restaurant was busy and getting the order to go was taking a while. Finally ordered and it was going to be 20 minutes to get food so I quickly went back to the hotel. Would the girl who took my order be shocked to know that 5 minutes before I was giving her the order, my gurl was giving me her cock in my mouth? In a few minutes it would be back in my mouth. Back in the room, she was in the bathroom when I came in so I grabbed another beer and drank a big gulp. I was still nervous, even though I was already with her previously. She came out and I told her it would be twenty minutes and I didn't want to be away from her for that long of time so I came back. She smiled and said, "How do I look?" She had on a sexy outfit that made her look like a dominatrix but not over the top. She was sporting a black bustier, black panties and fishnet stockings. I said she looked like a million and that it looked like she was going to be in charge in that outfit. She said she had plans that included me being her bitch all night long and I might as well start now. She sent me to the bedroom and told me to put on my lingerie and heels and then come out to the living room. I stripped and put on my black thigh high stockings and garter belt. I went with a smooth lime green sports bra that held my big nipple silicone breasts tightly to my chest. The nipples poked right through the soft spandex fabric, the main reason I purchased that bra. I really wasn't a sports bra because it had no padding but the design was the same; all the better to show off my tits I thought to myself. I didn't have time for the wig so I slipped on some black leather pumps and strutted out to the living room and told her I was at her service. She liked the lime green bra and felt up my tits and squeezed the nipples and I pretended that I felt her doing it. I said to her "ohh... squeeze them harder." Then I moaned as if I could feel her pinching them. She said to me," well it is apparent to me that that you are submissive little thing with a foot fetish." I said yes Miss, I am and I do. She put her foot up on the coffee table and pushed my head down, I got the gist. I knelt down and started kissing and licking her foot through the fish net stockings. I tried to lift her foot and put it in my mouth but she held it firm to the table so I kept kissing and licking. I tried to work my way up her leg to her crotch, but she kept pushing my head back down top her foot. I was rock hard and she knew it. I was stroking my cock and kissing away. She switched feet and I didn't skip a beat. I kissed and sucked away, I loved every second of it. She took her foot down and stood in front of me with her legs spread wide and pointed her red painted finger to her crotch. She was about half way hard already and tenting her black panties. I moved myself directly between her legs. As I moved toward her cock, she squeezed her thighs on each side of my head and held it like that, her cock was a few inches from my forehead but I couldn't get to it. She finally let go and at the same time pushed the back of my head up and into her meaty cock. I pulled the panties aside so fast she couldn't have stopped me. The big gurl stick was in my mouth so fast, I put suction on the head and worked my way down the shaft, I could feel the this bitch stick getting bigger and harder as I went down. From previous experience I knew I had my work cut out for me. As I bobbed up and down she moaned and thrust her hips forward as I went down on her. I was determined to get all the way down before I had to leave for the food. I opened wide as I could and tried to breathe with the cock in my mouth and then pushed all the way down. This was starting to get somewhat easier. I made it all the way to the base of her thick slick shaft that was glistening from my saliva and held it, my nose pressed against her body. She had to be impressed; I was getting better at handling this python. I came up and took some air and looked up at her like a puppy looking for acknowledgment from her owner. She smiled and said "you are getting the hang of it; I think I'll keep you." I said I had to go get the food. I was putting on my pants over the lingerie and slipped out the silicone tits and I heard her say "leave the bra on baby." I put on a sweatshirt type shirt that was loose fitting and she gave me an evil grin and then said OK you can wear that, but she threw me the multicolored socks she had on and said "wear these." Shit, I thought, there is no way I can explain that if they see them in the restaurant, then I thought fuck it, if they see them I will say my girlfriend made me wear them, it was that or she was going to paint my toes red! Yes that would do, anyone would wear these socks over getting their toes painted. Truth of the matter I would love it if she painted my toes and made me go out in flip flops. The trip for food was uneventful, I thought about lifting my pants somehow to show off my girly socks but did not, wish now that I had. Back in the room we ate and drank as boyfriend and girlfriend, no shenanigans. She knocked back quite a bit of the Cognac that I had picked up earlier and I slowed down on the beer. We cleaned up the mess and I went down the hallway to get rid of the trash as we did not want it smelling up the room. Now she told me that she wanted me decked out in a sexy secretary type outfit with full make up, wig and jewelry. I opened the closet and showed her the assortment of clothes I had hung up earlier. She immediately saw a beautiful red silk robe and took it out and put it on herself and she told me how much she adored silk, it was kind of small on me and I had acquired it like most of my things from a second hand store so I told her she could have it. She kissed me and said "you are making it hard for me to dominate you; right now I want to feel your cock in my ass." I told her that I would do whatever she wanted. She said; "well let's get you dressed and we will see about that later." I put on my corset and tightened it to cinch my waist; she picked out my black bra and red panties. I still had on her socks and black thigh highs and garter. She picked out a grey pencil skirt that was skin tight and four inches above my knees and one of my favorite tops it had super thin material, silky, stretchy long sleeve purple top. It accentuated my tits and you could see the nipples budding through the material. I put on the clothes and did my make up like a secretary who puts on a little more before she walks out the door and heads to a bar for a drink after work. Heavier on the eyeliner and some purple and a dash of silver for the eye shadow, blended them nicely. I put on some darker lipstick to match the purple in the top. Then the wig, my favorite silver bracelet and a costume necklace with silver chainmail and beads. A spritz of perfume and I was almost ready. She was rummaging through my girl things and making comments on my style and tastes. All of it complimentary, she was surprised to find out that my favorite store was Goodwill and most of it came from there. It is more thrilling to wear things I know another woman wore, maybe on a night out the previous owner was dancing in the clothes I now wear. Maybe she picked up a guy or took her husband home and fucked him in a skirt I am now wearing. If the previous owner knew where her things were now, that would be priceless to see some hot MILFs face! I brushed out my wig and stood up for her inspection. She looked down at my feet and said "really?" I still had on her socks, forgot that small detail. I told her I would only take them off if she let me keep them. She said to me, "well I guess you have earned them." On went with my higher heeled black Italian pumps. She said let's go back in the living room. She sat on the couch and told me to fix her another drink and bring it to her. She had on the couch with the red silk robe on and had slipped on a pair sexy black glittery kitten heels with pointy toes, different than I expected but upon further review as the saying goes, they did kind of look sexy, cute and mischievous all at once. Yes I thought to myself I like them, maybe it will be my next purchase? I sat next to her and we talked a bit and she told me she was worried that she was beginning to like me too much and that she was afraid that I would not want to be with her the way she wanted to be with me. She said that she wanted to be my only girlfriend outside of my home life which she knew would not change. She said as long as I was hers she would be happy. I told her that I was not seeing anyone and since I met her I thought about her all the time anyway so I was OK with it. She smiled and I could swear I almost saw a tear; I almost teared up myself as I was taken by surprise. I kissed her softly and said yes that I would only see her. She breathed heavy and we made out on the couch like two high school teenagers. I slipped my hand between her legs and I deliberately ran my fingers up and down her shaft with an open palm as if I was stroking a woman's clitoris. She noticed and was humping my hand and grinding her pelvis. There was no mistaking her freakin bulge for a clit however. I cupped her tits that were out of the top of her bustier and put her nipple in my mouth and sucked as I slipped her panties to the side with my free hand and put my fingers around her shaft and stroked slowly up and down. She was breathing heavy and moaning and I moved my mouth off her tits and kissed the soft dark skin of her neck as I made my way up to her mouth. We locked lips like we did before I left to get the food. This time was different, she was frenzied and kissing and sucking with a much higher level of intensity, I was kind of hanging on for dear life. She was moaning and saying how much she loved what we were doing and that her last boyfriend would never do what I do for her. I was a bit surprised but kept sucking on her tongue and taking in her juices. We broke lip contact and I rested my head on her chest, my wig hair was all over the place but I felt the need to press my face against her body. After a minute I slipped my hand around her semi-soft hunk of meat and stroked it, I could not bear the thought of it growing unless it was in my mouth so down I went. She said I want to video you sucking me and grabbed her phone. I didn't flinch and continued to suck up and down trying to do my best porn star imitation. I sucked the head, licked the shaft, my favorite, sucking her balls in my mouth imagining the growing amount of semen filling up in her balls. By now I was back on the floor kneeling between her knees as she ran her phone cam. I sucked away taking brief moments to breath. I made it all the way down on her several times, each time holding it a bit longer. I could feel her shaft all the way down my throat, I still gagged but not as much, maybe someday I will be a deep throating whore that she will pimp out for cash. She pushed me off her cock and said, I need that fucking smooth ass of yours! She grabbed my stiff cock in her hand and pulled me along by the cock to the bedroom. She matter of fact tone of voice like she was giving a command to a dog, she said, "up on the bed on all fours and show me that ass." I knew what was going to take place and unlike the first time I met her I knew I would be able to take the length and girth of her womanhood is my ass. I had cleaned out as usual and used a big dildo before I picked her up so I was stretched out enough so it would be easier to have this torpedo in my pussy. She stroked herself rock hard as her other hand rubbed my ass as she marveled at how smooth the skin on my ass was, she even said she wished her ass was this smooth. Hard as a rock, she slipped on the magnum condom and put the head of her cock against my pink little button of an ass. She squeezed some lube on my ass and rubbed the head of her cock up and down the crack of my ass and then settled down right on my rosebud. I asked if it was OK that she could hold her cock in place and let me back onto it like we did last time until I am on her and then when I give her the go ahead she can thump my ass like a fucking bitch slut. That got her going and I backed onto her. Her hot thick head pushed its way past my ring and into my ass. Slowly I backed onto the seemingly endless shaft. A bit more lube a few times and I was all the way on her thick, long, hard shaft. I reached behind me and tried to pull her hips towards me and she picked up on it and grabbed my hips and pushed all the way into me, getting the last half inch of her glory all the way into my body. I said to her "baby I am ready to be your only piece off ass and you will be my only gurl. Fuck me now, fuck me long and hard and I will be yours" That got to her as her previous conversation was weighing on my mind so I took the chance and blurted that out. When she said yes and started to fuck me. I repeatedly said, "I love how you fuck me." I said that about ten times in a row as she plowed my ass thrusting in and out. Then instead of repeating that I said once as she pounded away, "I love you." She grabbed my hips harder and pushed all the way in to my ass as far as she could go and held her rock hard 8 ½ inches in my ass. She finally relented and went back to fucking me. Transexual Encounter Ch. 02 She came closer behind me with her lips by my ear still pumping her hot shaft into my ass, she said," I want to bareback you and feel your ass on my cock, I want to fill your ass with my cum baby. Let's get tested together soon and then I want to fill your ass with cum, I want to feel your cock in me and I want to feel your cum in my ass too." I said yes I would do that between thrusts and she just kept pounding away. We fucked or should I say she fucked me for an eternity. Finally I collapsed on the bed and she fell on top of me and laid on my back and kept pumping her way in and out of my ass, I could now feel her pressing up against my prostate and a tingling in my balls sent shock waves up my cock. I told her to pump faster because I was going to cum. My hard on was rubbing up against the sheets and I flooded the mattress with cum and I did my best to sound feminine as I came. I kept saying over and over to her, "please fuck me and make me come, make me your woman, make me come hard" I repeated that as I came like a possessed cock starved bitch. I was spent and went limp, but my newly acquired one and only transsexual girlfriend pumped away as if I hadn't come at all. Now I was a rag doll along for the ride. She kept pumping and pumping and grinding. I did not expect what happened next and this had never happened to me ever. The continued assault on my ass and her relentless pounding made me cum a second time into the sheets, but my cock was completely soft, I didn't think it was possible but it happened, a burning hot orgasm with a limp cock being slammed to the sheets by a slim petite transsexual with a big hard cock. She had a seemingly endless ability to fuck like a machine, no exaggeration. This was real and happened as I have just described. I won't tell you her name because I want her all to myself, yes I am selfish bitch and I won't share her. She finally pulled out saying she was about to cum. She ripped off the condom and I rolled over on my back and she jammed the head in my mouth, her shaft was so long that she kept the head in my mouth and she stroked furiously until I felt my mouth flood with cum. It filled my mouth and spilled out as she pumped my face. I held a giant mouthful of cum in my mouth as she pulled out. I opened to show her and then I closed my mouth and sat up, rolled her around until I was on top of her and she was on her back. I opened my mouth on her tits and spread her cum with my mouth all over her tits and then licked all the cum back off her chest and swallowed it all. She said that was kinky and I told her I wanted to taste her cum all night every time I sucked her tits. We jumped into the other bed with clean sheets after I took my wig and corset off, I left my tits on and she slept naked next to me. We slept soundly and I woke her up in the morning by slipping under the sheets and sucking her soft cock in my mouth, she woke up and grabbed my ears and pushed my head down on her cock. She said to me, "did you mean what you said to me last night?" I said, "Every word of it." She told me she was very happy. She said "let's go get some breakfast." I said OK, but "I only drink a hot sticky protein shake for breakfast, do you know where I can get one?" She punched my shoulder and said, "Get your ass out of bed and let's get going girlfriend." We showered together and I lathered her body with soap and sucked her cock in the shower on my knees as the warm water rushed over our bodies. She said, "You may get that protein drink if you keep that up." We both laughed and got dressed and went out to eat. To be continued... ***** Feedback appreciated. Looking for an editor/proof reader for future stories.