A New Friend for Jaina

I followed suit by removing my dress. I pulled off my g-string and let my cock free. She reached down and gently stroked me as we continued to kiss. I couldn't contain myself anymore. I playfully pushed her back on the bed. She moved farther onto the bed and playfully waved her finger at me, telling me to come closer. I got onto the bed and moved toward her, eyeing those lace panties and what was surely hidden beneath them.

I reached forward and gently rubbed her. She was tucking, so I moved her panties aside and reached for her cock. She was still soft when I freed her cock, but she quickly got hard, and I began to gently stroke her. I gently pulled her panties off and tossed them on the floor. By now her seven-inch cock was free and fully erect. Thin, smooth, and completely shaved. I had never looked at another cock the way I was looking at hers. I had never so much as touched another cock before I touched hers. I continued to gently stroke her as she let out little moans. I could see precum begin to form on the tip of her dick. I wanted more, but I was nervous. As if she was reading my mind again, she gently told me it was okay. She told me to do whatever felt natural.

I leaned forward and, for the first time in my life, I took a cock in my mouth. I could taste the salty but sweet precum that had formed. I imagined her sucking my own cock and I tried to mimic what she had done. I gently swirled my tongue around her head as I stroked her shaft. I'm not sure if it was possible for her to get harder, but somehow she seemed to. She moved her hips up toward my head, as if begging me to take her cock fully in my mouth. I continued to suck, enjoying the feeling of her smooth cock against my tongue. I began to suck and stroke harder and she started to moan. "Are you sure you've never sucked a cock before? You're a natural, baby", she said to me as I took her full seven inches into my mouth. I felt the tip of her cock hit touch the back of my throat and I held my mouth there, resisting the urge to gag.

She gently stroked my hair as I continued to suck on her delicious cock. Suddenly she pulled away. She pulled me closer and kissed me. She told me I had her close to cumming, but she wanted to save her orgasm for something special. "Jaina, I want you to fuck my ass pussy. I want to feel your cock inside me. I want to feel your balls slapping against my ass. Fuck me, Baby!"

She reached over to the nightstand and grabbed a little handbag she had brought with her. She reached in a produced a small bottle of lube. She told me to get on my knees as she squirted a small amount of lube on the palm of her hand. She reached down and gently stroked my still hard cock, covering every inch with the lube. It was slippery and her hand slid up and down my shaft with ease. After my cock was lubed, she squirted another small amount on her palm and turned around. She bent over so her ass was facing me. She spread her cheeks and applied the lube to her ass.

She had a smooth ass. No hair at all. As she applied the lube to her ass, she slid a finger into her waiting hole. Then two fingers. She let out a little moan and told me she was ready for me. I grabbed her hips and pulled her toward me. The mushroom tip of my throbbing cock easily penetrated her ass. Was I really doing this? Had I really just finished sucking my first cock and was I really penetrating the ass of one of the most gorgeous women I had ever laid eyes on, even though she wasn't a woman?

Shayla let out a moan as I pulled the head of my cock back out. She moved her hips toward me, silently telling me she wanted more. I stuck the tip in again and she again moved her hips toward me, slowly forcing my cock into her hungry ass. I held her hips for balance as I slowly began to thrust my cock in and out of her asspussy. She continued to moan with every thrust. "Yes, baby. Right there. Your cock feels soooo good. Fuck me, baby. Treat me like the little slut I am."

It was almost surreal. Her voice and body were the embodiment of femininity. Her body was average, but curvy, the way I liked my real women. If I hadn't had her dick in my mouth a few minutes earlier I would have sworn she was a woman. And I probably would have bedded her just the same. As I continued to fuck her and she continued to moan, I began to wonder what I had been missing all these years. Why hadn't I done this sooner? I was in the midst of the most amazing sex I had ever had, and for all intents and purposes, it was gay sex.

I snapped out of my day dream as I continued to pound her. She was working her sphincter muscle around my cock in a manner that reminded me very much of an actual pussy. And she was moaning like a woman whose clit was being stimulated in all the right ways. I pulled out of her and turned her on her back. The lust in her eyes as I positioned her legs on my shoulders was almost powerful enough to make me blow my wad right then and there.

I stuck my cock back in her waiting ass and began to fuck her like there was no tomorrow. She pulled her legs off my shoulders and wrapped them around my back. The feeling of her silky stockings on my back was enough to drive me insane. She began using her legs to pull me deeper into her ass, begging me to fuck her harder. I could feel my balls slapping against her ass with each thrust. I reached down with my right hand while I steadied myself with my left and began stroking her cock. "No", she said. "I don't want to cum yet. Just keep fucking me, baby."

Hearing those words, mixed with the feeling of her stockinged legs on my back, were enough to bring me to the brink of an orgasm. "I'm getting close, babe. Do you want me to cum in your or on you", I asked. She licked her lips seductively as she said, "In my mouth. I want you to spray your love potion down my throat. I want to taste you." That did it. I could feel the orgasm about to happen. I pulled out and repositioned myself over her torso. She took my cock in her mouth and gave me a couple of stokes. I began to cum harder than I ever had before. She sucked every bit of cum out of my cock. She played with it, showing me her covered tongue. Then in one swift gulp, she swallowed every last drop.

"My God, you taste so good! I hope you find me as tasty." I looked down and saw her still hard cock, almost quivering. I took this as my queue to finish her off. I put my head between her legs and took her all in. I bobbed my head up and down as fast as I could, stroking and twisting her cock with one hand in rhythm with my bobbing. With my free hand I gently massaged her balls, using one finger to gently prod that wonderful ass I had just finished fucking.

Then it happened. I noticed a slight change in the way her balls felt a split second before she exploded in my mouth. The explosion of her warm cum caught me off guard and I reflexively gagged, causing most of her load to dribble down my chin. She laughed a bit and told me it was alright. Being able to tell when your partner is about to cum is something that is learned with practice. After the initial shock wore off, I held my head in place, her cock still oozing cum into my mouth. I swallowed what was left and licked my lips. It was a taste like I had never experienced. A little bitter, a little salty, and a little sweet, all rolled into one. It wasn't unpleasant and it was something I could definitely get used to.

We spent the rest of the night wrapped in each other's arms. Other than our shoes, we never bothered to get undressed. Throughout the night we constantly caressed each other. We chatted for a bit and she did everything she could to make sure I was okay. She knew this was my first time with a crossdresser, let alone also being dressed. I assured her I was great and she had shown the most amazing time I had ever had.

The next couple of days were uneventful. Shane was busy with his clients, and I was busy with mine. We had run into each other a couple of times, but never had the chance to talk about that night. We didn't get a chance to get together again that weekend and a part of me was sad that we didn't. Shane was beautiful as Shayla, much prettier than I was as Jaina. I had hoped to maybe learn some makeup tips while we were in town together. A part of me was also a bit jealous. I couldn't help but wonder if Shayla spent time with others the last couple of nights of the conference.

Monday evening rolled around, and the conference had come to an end. As I packed my suitcase I thought back to Friday night. I wondered if I would see Shayla again. The idea wasn't outside the realm of possibilities; after all, we both worked for the same company. I wondered if Shayla was wondering the same about me. Or was I just an easy lay for her? As I closed up my suitcase and headed down to catch the shuttle to the airport, I continued to wonder. Only time would tell, I guess.

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Thank you for taking the time to read my first story. I already have some ideas rolling around in my head for the further adventures of Jaina, including how Jaina meets Trevor/Tiffany, but until then, please feel free to DM me your thoughts and ideas.