1. Jessie's Reward


    Date: 11/4/2014, Categories: Crossdressing, Author: JessieCD, Rating: 16, Source: LushStories

    door-bell rang. I ignored it as I was not expecting anyone. It kept ringing, so I took my heels and wig off. I quickly put on sweat pants and a robe over myself so no one could tell I was wearing woman’s clothing. I answered the door and Dan was there. “Hi Jesse! I thought we deserved to celebrate getting that program back on track this week.” “Dan, I’m really tired, I don’t think it really is a good idea,” I replied. “Well, you owe me. For payment, it is celebrating our success,” he said as he barged in. I shut the door as he sat down on the recliner with a beer. I sat on the couch. “So Jesse, what did George say once you let him know how we were going to fix the project?” I answered his questions, not realizing that my five inch heels and wig that I took off were visible to Dan. He got up and sat next to me on the couch. I thought it was odd, but didn't really move. He continued his conversation, and over time, his hand went on my knee to emphasize a point. His hand stayed on my knee. I was starting to get uncomfortable. Dan suddenly said, “Model those high heels and wig for me.” I blurted out unconvincingly, “Those aren't mine. My sister left them here.” “We both know that isn't true, they are way bigger than what your sister would wear. Don’t you remember? I met her? There is no way those are hers. Now put them on!” I reluctantly put them on. As I bent over to strap my heels up, my robe separated and gave away another secret. “Wow Jesse! What have we here? You’re wearing ...
    a pretty hot looking outfit.” I started turning red with embarrassment. “What else is going on?” as Dan removed my robe and started pulling down my sweat pants. “Well, well. Looks like Jesse, or should I say Jessie, likes woman’s clothes. I wonder what else Jessie likes?” “I don’t know what you are talking about Dan.” “I think you look really hot all dressed up like that. It would be a shame for that to go to waste. Remember, you owe me.” He leaned forward and softly caressed my left cheek just before our lips made contact. It was a brief soft kiss. Even brief, I was amazed at the fireworks that were going off in my head. I wanted more. I leaned back toward him and kissed him. Next thing I knew, his soft tongue slowly parted my lips, and we were locked in a very passionate kiss. This went on for minutes before we released. “You are so sexy Jessie.” He gave me another passionate kiss, embraced my body softly and with respect. I was melting like butter in his arms. My resistance was weakening by the minute. Next thing I knew, his hands were under the skirt of my costume, and his hands were on my butt cheeks. My hand started making its way to his crotch. When it got there, he was very hard, and big. I started rubbing his crotch through his jeans. “Mmmmm. Yeah Jessie. That’s it. Keep doing that.” After five minutes of rubbing his crotch, I teasingly lowered his zipper and unbuttoned his jeans. I lowered his jeans and underwear enough to free his manhood. I placed may hand on it ...