tagTransgender & CrossdressersTransexual Encounter Ch. 01

Transexual Encounter Ch. 01


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.

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bySluttyValerie© 2 comments/ 41932 views/ 42 favorites

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