I had been seeing Ellie for a few months before I told her about my little secret. We enjoyed straight sex, but something was always missing for me. After I told her about Vanessa, and my desires to dress up and be treated like a woman, I was really scared she was going to cut and run, but she actually was interested in knowing more. I confessed some of my innermost desires to her. I told her about how I loved being with her, but that I really wanted to know what it was like to be with a man. I wanted to feel that combination of sexual power, and helplessness as I gave myself to a masculine guy.
She was unsure how far she wanted this to go, but she wanted to at least go out dressed with me. We planned a date together. I met at her place with my clothes and makeup which I usually had to hide away. She put on some girly pop music, and took out all of my stuff, then directed me to go shave myself clean in the shower. When I came out of the shower, she had all the clothes laid out on the bed, and my makeup on her makeup table, ready to go.
I took the hint, and began to get dressed. I was more excited than every before as I slipped on the silky black thong, bra, garter belt and stockings. I pulled on my little black dress, but decided to wait to slip on the 4″ heels I brought with me. I called down to her, and she shot up the stairs excited to see how I looked all dolled up.
She giggled a little, but said that she loved it. She had done her makeup already, so she sat me down at her vanity so she could do mine. I was OK at makeup, but I could never do it as good as my girlfriends. She gave me these sexy smokey eyes, and slutty red lips. Then, she slipped on my wig, long and blonde. I grabbed the heels, and we were ready to go.
We drove out to a local LGBT friendly club. I was so nervous to even get out of the car. She assured me not to worry, letting me know that she’d be with me the whole time. We held hands as we walked into the club, then made our way to a table, and had a seat. This club had a lot of straight people as well as LGBT people, and as I looked around, I saw some beautiful women, and some hot guys. Before I could say anything to Ellie, two drinks appeared in front of us. The waitress let us know that they were bought by a couple of men across the way.
We began to sip our drinks, as the men approached. They were in their early 30s, in good shape, and were very sexy. They asked if they could sit with us, so we let them, and we started chatting together. Derek and Ken were their names. We made small talk for about 20 minutes, and then Ken put his hand on my leg. I wasn’t sure what to do. Would Ellie get mad? Was this OK? I wasn’t sure, but I liked it. But as we kept talking, I felt Ken start to move towards me like he was going to kiss me, and I panicked. Then, Derek asked us if we wanted to go back to his place. I grabbed my purse, and grabbed Ellie by the hand, and rushed us to the bathroom. She told them we’d be right back.
In the bathroom I asked her is this was okay. I didn’t know where this was going. She told me that she loved me, but she knew that this was something I had wanted. She said that this would be a one time thing. This is what we came here for. I wasn’t sure how I felt about Ellie fucking another guy, but I know that I was really turned on by Ken, and like she said, this is what we came here for. “Okay,” I said. “Let’s go.”
We followed them back to Derek’s, and headed inside. He fixed us some strong drinks, and we sat on his two couches, me next to Ken, and Ellie with Derek. After some more small talk, Ken put his hand on my leg again, and this time moved right in for a kiss. I was so scared and confused, but I opened my mouth and let his tongue in eventually kissing him back. His lips locked against my mouth and our tongues rolling around our mouths felt so hot. I could hear Derek and Ellie making out too, and for a second, I wasn’t sure I liked that, but then Ken started rubbing my cock through my pants. He leaned into me, and I could feel his hard cock pressed against me. “Let’s go upstairs to the spare bedroom,” he said.
I looked over at Ellie and Derek. It was really uncomfortable, but I went with Ken to the bedroom upstairs. As soon as we closed the door, he kissed me hard again, pressing himself against me, grabbing both of my ass cheeks in his hands. I put my hand on his cock and rubbed him through his pants, until he just unzipped and pulled it out for me. I stroked his hard cock and it felt so good in my hand. I had fantasized about touching a man’s cock, and now I was, and it was wonderful.
He pulled up my skirt, and rubbed my hole through my thong. I moaned, and kept rubbing his dick. He licked his finger and moved my thong aside so he could slide his finger inside me. I had never had a man’s big finger in my ass, and I loved it. He knew exactly how to finger me, rubbing my prostate, sending shocks through my body. From this point on, he ignored my penis, and just focused on my pussy hole as his object of desire. He slid in a second finger, and fingered my pussy so good, I could feel a little cum dribble out of my dick. The whole time he was fingering me, he was also still kissing me deeply, kissing my neck, and letting me stroke his cock. But I definitely didn’t want to cum yet.
“Do you want to taste my cock, Vanessa?”
These words were like magic to my ears.
“Ken, I want to take my virgin ass. Will you do that?” I asked him.
His face lit up. He laid me down on the bed on my back, and pulled my thong off. He lubed his cock up and then slowly pressed the head against my asshole. I could feel him pressing inside me, slowly, and it filled me with pleasure. The more his cock went inside, the more I felt like the little slut that I always wanted to be. As my hole started to loosen up and accept him, he began fucking me a little deeper and a little harder. His big cock slowly driving in and out of my tight asshole sent waves of pleasure through my body. With my legs up on his shoulders, he fucked me so his cock was hitting my prostate just right. I could feel a girly orgasm building up.
He continued fucking me, and kissing me, deeply and passionately. I never believed my first time with a sexy man could be so hot. His cock kept filling me, and I loved the feeling of every inch sliding in and out of me. Finally, he whispered in my ear, “Vanessa, I’m going to cum inside of you, my little slut.” I melted at the sound of those words, and then melted more as I felt his cock throbbing inside me as he shot his hot load into my girly hole. His moaning turned me on even more. He pushed his cock into me as far as it could go, burying his cum deep into me.
He asked me if I wanted to cum, but the truth was I didn’t. I just wanted this feeling to last forever. We laid there together for a while, his arms around me. He kissed my neck a little, and then told me that he always loved girls like me more than real women. He loved how we treated him, and loved how we fucked. His fantasy was to meet a crossdresser that he could make his full-time girlfriend, and he eventually thought he wanted to get married to girl like me. I felt so wonderful. I didn’t even care about Ellie fucking Derek anymore. But I knew deep down inside, that her thought that this was a one-time thing was wrong. I told Ken, I definitely wanted to see him again. In fact, I think I decided right then and there that I was ready to be Ken’s girl.