A New Friend for Jaina

Hello. This is my first story. It is 100% pure fiction based on personal fantasies and not based on any actual events. I hope you enjoy.

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I am a software programmer by education and training, although my current job has me doing a lot less in the way of programming and a lot more in the way of being an account representative for the software company I currently work for. I work closely with two other account reps, Shane/Shayla and Trevor/Tiffany. This is the story about how I came to meet Shane/Shayla. The story of meeting Trevor/Tiffany will be coming soon.

Things weren't good at home. My wife and I were arguing more frequently, and the arguments were getting bigger. We had started drifting apart, as occasionally happens when two people have been married as long as we have. And to make things worse, I discovered she was cheating on me. I hadn't told her I knew, mostly because I kept hoping it wasn't true. I had the evidence right there in front of me, though. Hundreds of text messages and photos between the two of them, talking about how great their dates were, what they were going to do on their next date, photos of what she planned to wear on their next date, and more. In a way I felt like it was my fault, as I traveled a lot for work. But never in our entire relationship had I strayed.

I also kept my knowledge of her affair to myself because my discovery got me to thinking. I had been bi-curious since my teens, and I had been crossdressing on and off for as long as I could remember. I started thinking about having my own little side affair, or at least finding someone to hook up with to satisfy my curiosities. The problem was, I was in no way, shape, or form attracted to men. Without a doubt, I liked women, or at least I liked the appearance of women. Even when I was crossdressing while on a business trip, I typically found myself watching crossdresser or transexual porn and imagined myself having a lesbian affair with one of them. But I had never met with another crossdresser or transgendered woman. That was about to change.

I had a trip to coming up. It was time for the annual conference hosted by my company. Hundreds of other employees, clients, prospective clients, and representatives from other companies in the industry would be attending. I would be travelling from San Diego to Portland. I would be in a city unknown to me, but I would also be unknown to them. I decided Portland would be the place to have my first encounter with another crossdresser or transgendered woman. And I would be doing it as Jaina.

I put my plan in action by checking out the Doublelist ads for Portland. I was specifically keying in on any ads that mentioned "CD" or "Crossdresser". I found a few, but most of the ads were from guys who liked to wear panties or were from people who were looking to get high and fuck. I like the beauty and I appreciate the time it takes to get all dolled up, and I don't do drugs of any kind, so those were all out. But I wasn't going to give up. I had a couple of weeks before the trip, so I kept searching.

As the trip got closer I still hadn't found someone I was willing to meet up with. There were a couple of promising people that I contacted, but when I contacted them, I discovered one of them only dressed from the neck down and had facial hair, and the other was looking for a quick fuck as soon as possible and wasn't willing to wait another week. So, I posted my own ad with a couple of faceless pictures wo anybody who thought of responding could see what I looked like from the next down.

DL, MWM, Bi-curious CD. Not just a pantyboy. I dress fully from head to toe, including makeup and wig. Traveling to Portland next Thursday through the following Monday. Looking to meet a local gurl for some dress-up time and more if the vibe is right. Would like to email or chat a bit over the next few days to make sure we are both comfortable. Absolutely NO masculine men. NO hairy crossdressers. I'm smooth all over, you be as well. And NO druggies. I know, it's Portland. 420 is OK, but not in my presence, please.

The ad got a lot more response than I expected, and a lot more than I wanted. Within a couple of hours my inbox was flooded with emails from guys claiming they would treat me like everything from a lady to the little sissy slut I was. Hairy guys, smooth guys, chubby guys, skinny guys, tall guys, short guys, and more dick pics than I could shake a stick at. While some of them looked enticing, that wasn't what I was after. I mean, sure, some of the dick pics got me horny and I imagined myself going down on them, but I wanted the full CD on CD experience.

As my bad luck would have it, by the time my Portland trip arrived I still hadn't secured a date for any of my nights in town. I got to my hotel and checked in, then headed straight to my room. Along with my male business suits, I also packed some sexy but classy ladies' business attire, lingerie, and heels as well as my makeup bag. Anybody looking in the suitcase would have thought a couple was sharing a suitcase on a trip. I unpacked my things and hung them in the closet and decided to see what else Portland had to offer. I was checking the Doublelist ads again and an ad for Grindr popped up. I wasn't sure what Grindr was, so I checked it out. As it turned out, I discovered Grindr might provide me with more success than Doublelist. I created an account for my alter ego and began browsing.

There were a lot of very pretty trans women on there, but they were all looking for muscular jocks. While I exercised when I could, I was by no means either muscular or a jock. They were pretty much out of my league. There were a lot of crossdressers, too. Some were way sexier than others. I started getting taps and a few guys messaged me, but like the Doublelist ads, most were hairy men that I had no interest in. I was about to shut down the app and head down to the bar for a drink when I received an email. It was another Doublelist reply:

Saw your ad. You look sexy. I also like to fully dress from head to toe. Like you, I'm also from out of town and will be arriving tomorrow. Would love it if we can get together for some gurl time while we're both in town. I attached a couple of pics. Let me know if you like what you see.

I definitely liked what I saw. What I saw was an average but curvy "woman" dressed in a red blouse, black knee-length pencil skirt, nude stockings, black sling-back platform pumps, and wearing a brunette wig. Her makeup was flawless, and if she hadn't told me she was a crossdresser I never would have known. I was about to reply that I would love to meet up when I got another tap and message on Grindr. I checked and the user's profile pic was the same as one of the pics in the email I had just received. I opened the message:

"Your profile pic looks familiar. I'm pretty sure I just sent you a reply to your DL ad. Small world."

I replied and we had a brief conversation. I learned her female name was "Shayla" and she was coming into town for the same conference I was in town for. She was even staying at the same hotel as me. She suggested we get dolled up and meet in the hotel bar for a couple of drinks after the end of the day's events the next evening, then head to one of our rooms or a little more intimacy. I shyly explained that I wasn't anywhere near as passable as she was and didn't go out dressed in public. Ultimately we both agreed that we liked what we saw in the pictures and decided meeting as our male selves wouldn't be bad.

I could hardly contain my nerves the next day. Every fellow employee I talked to and every potential client I met had me wondering if they were secretly Shayla. The days events were fairly mundane beyond that. We had the typical opening ceremony, followed by breakout sessions and seminars all day with lunch and dinner provided to us. After dinner was the daily cocktail party in one of the bigger conference rooms. It was during the cocktail party that I noticed a shorter guy of average build staring at me. There was something oddly familiar about his face, but I couldn't quite put a finger on it. I chalked it up to probably having seen him in passing during the day. I gave him a typical guy's "what's up" nod and he started walking over to me.

"Hey, how are ya? I'm Shane. I handle the accounts for the South region", he said. He went on to tell me he was from Dallas and he always looked forward to the annual convention. I introduced myself in return and told him I was from San Diego and was the account rep or the Southwest region. We chit-chatted for a bit and learned both of us were actually programmers, but the account rep positions paid better and had the added benefit of all expense paid company travel all over North America, Europe and Asia. After a few minutes, Shane looked at his watch, looked me up and down, and abruptly told me he was sorry, but he needed to meet someone in the bar in a few minutes. I mentioned to him I was also had someone to meet in the bar and suggested we head over together.

We walked into the bar and discovered it was fairly empty. There were two couples sharing a table, laughing amongst themselves, and two men chatting with the bartender at the bar, but no one else. Most of the hotel guests were attending the conference and they were still at the cocktail party. Free booze over expensive hotel booze wins out every time. We ordered drinks and grabbed a table to wait for the people each of us was supposed to be meeting in the bar. As we chatted for a few minutes longer it dawned on me. I suddenly knew why Shane looked so familiar. I couldn't believe how much different he looked without makeup, but there was something about his eyes that told me Shane was Shayla.

I grabbed my phone and told Shane I was going to send a quick text to the person I was supposed to meet to let him know I was in the bar. I opened the Grindr app and went to our conversation. I looked closely at Shayla's profile pic and felt confident that Shane was indeed Shayla. I sent a quick "I'm here in the bar" message. A few seconds later Shane reached for his phone. He looked me in the eyes and said, "Something told me you were Jaina, but I wasn't sure."

My heart started racing. I didn't find the person in front of my attractive at all. I mean, Shane was a good-looking guy, but I just wasn't into guys. But I know how Shane looked all dressed up. As if he could read my mind, he told me, "It's okay. I don't bite...hard. Unless you want me to bite hard."

I admitted I was nervous and asked if we could sit and talk for a bit to get to know each other before doing what we planned to do. Shane was happy to oblige and over the next half hour or so I told him about how my marriage was falling apart, my wife was cheating on me, how I had crossdressed off and on for most of my adult life, usually when travelling, and how I was bi-curious. In turn, I got to know Shane. I learned he was also married and that he and his wife were both openly bi. He had been crossdressing regularly since he was a teen and his wife was completely open to him dressing with her. His wife was who taught him to do makeup as well as he did and would even be open to teaching me if the opportunity ever came up. He told me they had shared several lovers, men and women, with him dressed as Shayla. He had a way of putting me at ease. Three drinks later and I felt my inhibitions leaving me. I gave Shane/Shayla my room number and asked him to meet me in a couple of hours.

I had to resist the urge to run to my room to start getting ready. I hopped in the shower really quick and shave any stubble that had started to grow on my legs, arms, chest and face. I reached around to my rear and felt some hairs, but decided this was not going to be my first time bottoming. I already knew Shayla was versatile, so hopefully if things went that far, she would let me top.

I grabbed my iPad and propped it up so I could see it. I navigated to my favorite YouTube makeup tutorial channel as I let my moisturizer set in. I picked out a cute purple and black bustier with garter straps and matching g-string, a pair of black Wolford stockings, black pumps and a purple and black bodycon dress and laid them out. As I pulled the stockings on a rush of exhilaration came over me. I had forgotten how wonderful stockings felt on freshly shaved and moisturized legs. I put on the bustier and attached the garters to the stockings and pulled on the g-string. I took a quick look in the mirror and almost instantly got an erection. I didn't look half bad, and I still had to do my makeup, put on my dress and heels, and put on my wig.

I headed into the bathroom and sat at the dressing table. It had a nice mirror and bright lights all around so I could see what I was doing. Foundation, contour, blush, eyeshadow, liner, mascara, false lashes, and finally a nice neutral red lipstick and I was satisfied with what I saw staring back at me. It wasn't perfect by any means, nowhere near as perfect as I would have wanted it to be if I was going out, but for a night in, it would do.

I put on my dress, a pair of clip-on earrings, a choker necklace, and some other jewelry and finally grabbed my wig. I loved this wig. It was ombre, from brunette to blonde highlights. Long, past my shoulders, and made of human hair. It was probably the most expensive thing I had in my crossdressing ensemble. I put in on and adjusted it. It was in pretty good shape, in spite of being packed in a bag and thrown in a suitcase. I adjusted it and applied a small bit of contour over the small bit of lace that lined the top of my forehead. I was looking sexy, if I did say so myself.

I finished by applying a small bit of Obsession behind each ear and on my neck. It was an older perfume, but it always got me aroused when my wife wore it. I was hoping it would have the same effect on Shayla. As I reached for my heels there was a knock at the door. I looked at the hotel alarm clock on the nightstand. Had it really been two hours already? Indeed it had. I couldn't believe it. As I put my heels on I felt my little friend come to life again. I made a quick adjustment and tucked my hardening cock between my thighs. There was no way the g-string was going to keep me tucked and I hoped I would be able to hold myself in. I took another look at myself in the mirror and made sure my erection couldn't be seen. Yes, Jaina, you look pretty damn good.

I carefully walked to the door. It had been a while since I walked in heels and I didn't want to look like a clumsy oaf. I took a quick look through the peephole and saw Shayla standing there. I opened the door and saw a beautiful woman staring back at me. She looked nothing like the Shane I had been sharing drinks and conversation with just a couple of hours before. She had on a sexy black blouse, a black mini-skirt, black platform pumps and black stockings. Her hair and makeup were flawless and just like her pictures, if I didn't know the person staring back at me was a man, I never would have guessed. She was wearing a choker that very effectively covered her Adam's apple.

"Well, are you going to invite me in or are your going to just stand there staring at me?" she asked in a voice that even sounded like a woman's voice. I blushed, although I'm sure it couldn't be seen under my makeup. I stepped aside and invited her in. She carried with her a bottle of wine and two glasses. She set them down and immediately headed or the phone. She picked it up and spoke to room service. She ordered hors d'oeuvres and two more bottles of wine and asked that they be charged to her room. She gave some info to confirm her room number and hung up. The look on my face must have said I was horrified at the thought of answering the door dressed as a woman. She gracefully walked over to me, stood on her tiptoes, and before I had a chance to react, gave me a quick kiss on the lips and told me not to worry, that she would answer the door.

She returned to the wine and opened the bottle. She poured us each a glass, took a seat on the loveseat, crossed her legs, and patted the seat next to her. I gingerly and semi-clumsily stepped over to the loveseat. She let out a little giggle and told me, "Walking in heels gets easier with practice. I'm just glad you aren't also wearing platform heels. You would tower over me if you did." She was right. At 5'10" tall, I was probably 6'2" with the heels I was wearing. She was maybe 5'6" without heels, and maybe 5'11" with the heels she was wearing. I sat down, remembering to tuck the bottom of my dress under my legs when I sat, and crossed my legs.

She was gorgeous. I kept thinking to myself that I would make love to her even if I wasn't dressed. The thought crossed my mind that she may have found me attractive even in male form, but I decided to leave that question or later. As we waited for the hors d'oeuvres to arrive we chatted about all things feminine. I was actually getting into this persona more than I ever had before. As nervous as I was before meeting Shayla, I was now more comfortable than I ever though possible in her presence. As we chatted, I noticed her nails were also done. I asked her how she managed to get a manicure and get her makeup as flawless as she did in just a couple of hours. The nails, it turned out, were glued on acrylics. She kept three full sets ready to go and could put them on in a matter of minutes. As with heels getting easier to walk in, she told me getting quicker and better with makeup also comes with practice.

The hors d'oeuvres arrived and we munched on them as we finished the first bottle of wine. We sat there looking each other over and I told her how beautiful she was as she gently rubbed her leg against mine. God, that felt so hot. As much as I loved the feeling of my own two stocking clad legs rubbing against each other, it was nothing compared to the feeling of someone else's leg rubbing against mine.

Without a word she leaned over and kissed me. It wasn't like the peck she gave me when she first arrived. This was a passionate kiss. Tender. Gentle. She slowly slid her tongue in my mouth and I pulled her closer. As I pulled her closer, she stood up and straddled me, her knees on either side of me. We kissed for what seemed like an eternity, but I know it was only a few minutes. Without realizing it, my cock must have popped out between my thighs. It was rock hard. Rock hard for this beautiful woman who I knew had to be as rock hard as me.

Shayla reached down between my legs and gently stroked me. "Mmmm. Someone is excited." I admitted I was, but I wasn't sure how to proceed. Without another word she slid off the loveseat onto the floor in front of me. She lifted my dress and pulled my g-string to the side, freeing my cock completely. "Yummy", she said as she took my cock into her mouth.

She began sucking my dick slowly, swirling her tongue around as she gently stroked my shaft. Her mouth felt better than any pussy I had ever had. It was magical. As she took more of it into her mouth her hands went from gently stroking to a twisting motion. Without a doubt, this was turning into the best blowjob I had ever had. She pulled on my hips and pulled me to the edge of the loveseat. Without warning she took her free hand and began gently massaging my balls. I was in heaven. Shayla was sucking my cock better than any woman ever had. She continued sucking my cock for a few more minutes. I was nearing the point of exploding a hot load of cum down her throat when she began to slow her momentum. As she slowly sucked my cock she looked me in the eyes and gave me a knowing wink. She knew I was about to cum! Damn, this girl was good.

She got up from her knees and pulled me up. She pulled me in for a kiss and I could smell my cock on her breath. Instead of being repulsed, as I thought I would be, it turned me on. We kissed for a few more minutes and she gently pulled me toward the bed. She began to remove her blouse and skirt. Damn, she was sexy. She didn't have a hard body like the models in the porn videos I was used to watching, but she still looked damn good. She had on a black bra, a black garter, and a pair of black lace panties. There was no bulge in her panties, but I was sure they were hiding a treat for me.