Beginnings: My First time as a crossdresser (PT 1) - Sex Stories

Beginnings: My First time as a crossdresser (PT 1)

... looked quite the sight, my mascara was running down my face, my lipstick was smeared and my lips were red raw and puffy from the brutal treatment they had received from Derek. I don’t think anyone could have looked at me and not known what I had been doing. It took about ten minutes but finally I Iooked presentable. Walking out to the main area of the bar I realized Mikki was nowhere in sight. Danni was still there and I asked her where Mikki was. “She thought you left the bar without telling her so she left with that guy. What happened to you? You look like you’ve been rode hard and put away wet!” Feeling a bit naughty I replied “I was.” Then winked and walked out of the bar. I froze my legs off walking back to Mikki’s dorm, when I got there her door was locked and I couldn’t hear any noise coming from inside. I knocked but there was no answer. I was totally screwed. I couldn’t hang out in the hallway and I couldn’t walk home in those heels, especially dressed up the way I was. My clothes were in Mikki’s room and I had no idea where she was. I thought about it for a bit and realized that I did have one option open to me. One I felt oddly appealing, I played Dungeons and Dragons back then and one of the guys I played with, Tracey, lived in an apartment a few blocks away. Tracey was older, maybe around 30 and was gay. I also knew he had a bit of a crush on me. I had turned him down months before but now seemed like a good opportunity to have some more fun while I was dressed ...

... up and I knew he wouldn’t out me to everybody as he had told me it would be our little secret if I ever changed my mind. I walked the five blocks to his apartment and was chilled to the bone by the time I got there. Praying that he was home, I rang his doorbell. It was about 2 am. After another minute I rang it again. I saw a light flick on, Thank God! After a couple minutes Tracey answered the door in his bathrobe. Blinking, he looked at me in confusion “Excuse me miss can I help you?” “Tracey , it’s me Rob. Can I come in?” Now he looked even more confused for a moment until I saw realization blossom in his eyes, grinning broadly he stepped back and motioned for me to come in. “And to what honor does bring the warrior maiden Leighanne to my humble abode?” (He always talked that way and Leighanne was the name of one of the characters I played sometimes, an elven warrior princess.) Looking at me he could tell I was freezing so he took me over by the fireplace and got a fire going while I huddled under a blanket he had put around my shoulders. Then he grabbed us a couple glasses of Brandy, waited a few minutes until I had stopped shivering and said “So this is a story I’ve got to hear, Out with it. And I want ALL the details!” First I needed some more weed, so I had him load us a fat bowl, and then I told him everything between deep pulls on the pipe and sips of Brandy. It was a very good brand, smooth and mellow and also quite strong. By the time my story was finished I was ...