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I want to share with you the night I came out of the TV closet with a friend of mine. Jeff and I have been friends for several years. I met him on one of our company’s many weekend business trips.
I’ve been cross-dressing ever since I can remember. My wife knows about my penchant for dressing up, but I usually save it for when I go out of town. I carry along my special suitcase and spend the nights with my favorite "girl."
A couple of months ago, Jeff and I were chosen to go handle an out-of-town case. There was a mix-up in reservations, and Jeff did not have a room waiting for him. When I offered to share my room, he readily accepted.
After we settled in, we went downstairs and had a couple of drinks in the bar. Frankly, we were trying to find a woman or two for a good time that night. But we didn’t have any luck, so we decided to get some sleep. When we went back to the room, Jeff asked me if he could borrow my toothpaste. Without thinking, I said, "Sure, it’s in my suitcase." I didn’t think he would look in my overnight bag. I was just getting undressed when he walked in with my wig and heels. "What are these for?" he asked with a silly grin on his face.
Since I had been caught red-handed, I confessed to him that I was a transvestite. He said, "Show me." Figuring there was nothing to lose now, I told him to go downstairs to the bar and I’d dress up for him.
Jeff left, and I got ready. I quickly picked out my favorite white dress and slipped it over my slender frame. I put on my wig — a curly, shoulder-length blonde one-pantyhose and my black spikes. I was just finishing putting on my makeup when I heard a knock at the door.
I looked through the peephole and saw Jeff waiting in the hall. I let him in, and all he could say was "Wow!" The next words out of his mouth surprised me. "You’re beautiful. Let’s go out." I try to dress tastefully, and I think I make a pretty woman, so I was flattered and said yes without thinking. I put on some dangling earrings, and we were on our way.
Jeff took me to an intimate restaurant, where we had a leisurely meal. Then he got a cab to take us somewhere to dance. I was really getting turned on during the slow dances. Jeff is about six-feet-two-inches tall, with an athletic build, so he was still taller than me with my heels on; we made a pretty attractive couple.
Jeff suggested we get back to the hotel. I was all for that, as I wanted him inside me. We were barely in the door when he started to unzip my dress. He pulled it down off me, leaving me in my bra, pantyhose and heels. I wanted the illusion to last, so I tilted my face up and kissed him. Our tongues tangled in a passionate struggle for dominance. I excused myself for a minute to use the bathroom, and when I came out, he had already stripped.
I saw that he had a huge dick, much bigger than my own. I couldn’t wait to taste it. I had redone my lipstick in the bathroom, and now I wrapped my red lips around the head of Jeff’s cock. He was moaning in delight, and all I could think of was "So this is what I’ve been missing." I could taste his pre-come in the slit of his cock, but I wanted to taste and feel his come splash against the back of my throat. Mmm, so delicious!
I started to suck for all I was worth, taking as much of his meat in my mouth as I could, my head bobbing up and down furiously. I couldn’t get it all in. so I used my hands on the base of his cock and on his balls. After only a few minutes, Jeff came with great gobs of steaming semen. I didn’t think it would end. and I didn’t want it to. I sucked him dry. I let his spent meat fall out of my mouth and stood up to give him a kiss.
Jeff took me by the hand and led me to the bed. He gently finished undressing me and started to sprout another hard-on. I told him to wait and made him lie down while I brought some hand lotion and condoms to the bed. Then I daintily straddled him, tore open a condom and was amazed by the feel of rolling it down this big, strange cock. Then I reached for the hand lotion and started smearing it on his rubber-sheathed cock. I climbed on and let him take me up the ass. What a great feeling! We fell asleep with his cock still in me. In the morning I came all over his chest and licked it off, driving him crazy.
Jeff and I go on as many business trips as we can manage, and each time we go, he brings along something new for me to wear when we go out. Since these are the only times we can do what we enjoy, we don’t leave the room that often anyway.