This a fantasy of mine and my first story that I am submiting.
For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy hot woman.
She helped me to shave my legs and she picked out some hot looking clothes. As I put on the panties I could feel my cock start to get rock hard and she helped me put on some thigh high stockings and a garter-belt. She had picked out a bra that matched the panties I was wearing and I loved it. After I put on the very nice pleated skirt that went down to the middle of my thighs that made me like a hot little slut and the blouse that I put on finished it all off as I looked down I wanted to fuck myself. She did my makeup and helped me to put on the very sexy redheaded wig that she had put in to pig tails. When I tried to look in the mirror, she would not let me saying, “You can look when I am done ok, my slutty friend?”
To this I said, “Fine Stephanie, I won’t look yet.”
However, I really wanted to see how slutty I was looking. She looked at me and said, “What should your slut name be? Kendra or Mackenzie?”
“Whatever you think it should be, I feel like your creation since you dressed me all up.”
“My creation huh? I really like that idea.” She looked me up and down and said, “Come look at yourself in the mirror now, Kendra. Do you like what you see?"
I did. I loved it, and asked her “How many guys do you think will try to pick me up?”
“I don’t know let’s go to the club and see how many guys hit on us.”
As we sat at the bar and had a few drinks I had a really hot guy walk up to me and offer to buy me a drink. I was shocked but accepted. We went over to a table and started to talk and he put his hand on my knee and asked my name. I said, “Kendra, how often do you come here?”
“Not that often. I am only in town for a few days, by the way, My name is Rich why do you ask?”
“I think you’re hot”
“Really you’re a hottie too. Do you want to go back to my room?”
I could feel his hand moving up my thigh and when I tried to stop me he leaned in and kissed me, I did not think that I would enjoy kissing another man but it was hot. While he kissed me, I could feel his hand move up under my skirt and I did not care if he found out my secret getting rock hard in my panties. When he touched my cock, I felt his hand move and he stopped kissing me. He looked at me and said, “Are you in drag?”
I sighed and said, “Yes I am.”
As I was looking down and then he whispered in my ear, “I liked the feel of your penis through your panties, and would love to do more with you.”
Before we left, I told Steph what was going on and she said, “Be careful I don’t want anything to happen to you at all.”
“I know,” I told her as I walked away.
Rich lead me out to his car and I we started driving down to his hotel, and I started to feel him up through his jeans. I was amazed at how hard he was getting from me touching him. After we got in his room, he shut the door and tuned on a few lights. I unbuttoned his pants and dropped his pants and boxers to the floor. I then dropped to my knees and took his wonderful 8” cock shaft in my hand. I started to lick the tip slowly, then I went down the bottom of his shaft and he was moaning and grunting. I looked up at him and asked, “Do you like this? A guy in drag sucking your beautifully hard cock?”
He looked down at me and said, “Oh yeah! Suck that cock!”
I then took the tip in my mouth and was shocked at how much I loved it my mouth. As I took more of it in my mouth I could feel him getting even harder, I did not think that could happen. I started to deep throat him and lifting my skirt started to rub my cock through my panties with one hand and with the other one I started to cup and lightly play with his balls. I sucked on his cock and played with myself for another 5 min or so then I could feel his cock get thicker and his balls get tighter and I knew that I was about to get my mouthful of cum. I was a little nervous that he would shoot such a large load that I could not contain it all. I went back to sucking on the head of his cock flicking my tongue while I sucked and then I heard him grunt and say,
“OH MY FUCKING GOD, I AM GOING TO FUCKING CUM! WHATEVER YOU DO, DON’T FUCKING STOP SUCKING ME!” Just then, I felt his hot salty cum shoot in the back of the throat. I began to swallow his wonderful load and he started to spurt some more in my mouth and It was too much for me some slipped out of my mouth on my chin. When he was done cumming he looked down at me on my knees smiling with cum on my face and in my mouth and asked,
“Did you cum in your panties you hot little slut?”
“Not yet," I said, "I was more focused on giving my first blow-job why do you ask?”
“I want you to cum in my mouth now.”
I was so shocked and aksed him, “Really?”
“Yes,” he told me and helped me get up. He took off my skirt and blouse and looked at my hard cock just wanting to be let free of the confines of the lacey fabric. He undid my garter belt and took off my panties.
“How often do you do this?” I ask him, to which he replied "You’re the first one.” Then he took my cock in his mouth and began to flick the tip with his tongue and we he moved down on the shaft I felt myself get close to cumming and said, “That’s better than any woman could suck my cock OH, MY, GOD! OH SHIT!” just then I shot the load of my life in his mouth and I saw him try to swallow it but it was way too much for him to take down and some spilled out of the sides of his mouth.
“MMM that was wonderful,” I said.
He replied, "I thought you would enjoy that since I had a feeling it was your first time. When you asked how often I do this, I pick up girls like you a lot I love it when I feel their cock under their panties.”
“So I am the first one you have sucked off?”
“Yes, I have given a B.J. before but never sucked them off.”
“Well I am honored, I would like a shower would like to join me?”
“Why not?” he told me and we undressed and played a bit more in the shower. I could feel his hands touching my ass and start to play with my “man-pussy” a little bit and I loved it.
After we showered, we were both tired from our fun earlier and decided to climb in to bed. I put my head on his chest and it felt right to me. We kissed good night and I told him, “You can put that wonderful prick of yours in my ass in the morning.” He just smiled and then we spooned and I could feel his cock rubbing on my ass. I opened my cheeks a bit and we both went to sleep.
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<a href="http://www.lushstories.com/stories/crossdressing/my-first-time-3.aspx">My First Time</a>