I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me.
It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you. Let's go on a date sometime."
He knew that I wanted so badly to have a sweet man take me out on a real date, and treat me like a lady. Of course he also knew that I wanted to be seduced at the end of the night.
We texted back and forth a few times to try to nail down a day and time. There was some playful flirting too, but I didn't want to overdo it. We had been talking to each other for months off and on, and he was one of the few men that I had met online that actually made me think that maybe I could get serious with a man. My few encounters were brief, but the idea of becoming someone's girlfriend was one that always intrigued me. It made me wonder even further, could I maybe someday become someone's wife?
On the night of our date, I made sure to go all out. I took a nice hot shower, and shaved everywhere, making my skin nice and smooth. I put on some lotion, and then got dressed. I wore a sexy pink and black lace thong, with a matching bra, and garter. I slid on my lace stockings (always my favorite part), then got up and slipped on my sexy blue dress. My shoes, were black four inch heels, which I knew he would love. I did my makeup like a girl going for a night on the town should. Smokey eyes, sexy lips, and my favorite Victoria's Secret perfume. My wig was a sexy, wavy, long brown wig, which perfectly framed my face. I slid on a pretty silver bracelet, and my little heart pendant, and I was ready to go.
We decided to meet at the restaurant being that it was a first date and all. I was so nervous walking to my car, but I gathered up my courage, got in, and was on my way. The drive there was a mix of nervousness and excitement. We had exchanged enough pictures that I wasn't worried about him not being attracted to me, but I was still worried about what to expect. As I pulled into the lot, I got a text telling me that he was waiting in front. I parked, turned off the car, and took a deep breath. It was time to finally go on my first real date as Vanessa, and I was loving it.
I met him at the entrance, and he greeted me with a kiss on the cheek. "You look amazing Vanessa," he told me.
"Thanks, you look very handsome, Greg."
He took my hand, and led me into the restaurant. I was so nervous as we were seated. Were people looking at me? Could they tell? What would they think. Greg made me so comfortable though, I didn't even care. We had such a lovely dinner, and he was a gentleman the whole time even after all that wine. I wasn't sure I wanted him to be, but it was a nice gesture. We skipped coffee and dessert, and decided to go for a walk after dinner.
We walked by the river, and he took my hand as we just talked. After a few minutes, he stopped and turned me towards him. He looked deep into my eyes, put his hand on the back of my head, and gave me a slow deep kiss. I kiss him back feverishly. I was waiting for this moment all night. Our kiss ignited a passion in the both of us that was welling up for months. He wrapped his arms around me and pulled me close to him as our tongues entwined in our open mouths.
I whispered into his ear, "Why don't we head back to your place?" He agreed that would be a good idea.
I had drank a bit too much, so we both went in his car. Without my car it was like that one last bit of security had disappeared. I was totally at his mercy now. As we entered his living room, he asked if I wanted another drink. I told him a vodka tonic would be great, so he made us a couple of drinks. I looked at him, thinking about how long it could take to sip at this thing, and just downed it. I couldn't wait that long.
I wrapped my arms around him, and started kissing him again. I could feel his cock getting hard against me, as his hand slid up my leg and slowly up my dress. He grabbed my ass tight, and I moved my hand down to his erection. I undid his pants, and pulled it out. It was so beautiful to see it for real rather than in photos. I stroked his cock, and he told me that he had been dreaming about this.
I moved my head down to his cock and started kissing the head. I hadn't had many cocks, but this one was really something nice. It was so pretty and smooth. I loved the way his cock skin felt on my lips. I opened my mouth and took it inside, running my tongue around the underside as I bobbed my head up and down. His moans made me even hotter. I took him all the way down to the base. I loved the feeling of his rod in my throat as I licked the base with my tongue and played with his balls.
He stopped me and started kissing me again. Slowly he stood me up and took off my dress. "You're so sexy," he told me. He laid me down onto the couch and kissed me some more. He licked his fingers and pushed one inside my hole. He was kissing me so deep and fingering my pussy, and I felt so sexy. He pushed another finger in which hurt a little bit, but felt so good.
I looked him in the eye hoping he would be able to read that "it's time for you to fuck me" look. He got the hint, and he positioned himself so he could put the head of his cock against my hole. My dick was so hard at this point, I was leaking some precum on myself. He was teasing me with the head of his cock and I was loving it.
Slowly he pushed inside of me and I loved the feeling of every inch as it slid into me. My legs were up in the air as he started to pump me faster and harder. It felt so good, and I felt like such a sexy, slutty woman, as his cock found all the right spots. He was so deep and moved with such passion inside me, I could feel an orgasm welling up inside me even without touching my dick.
I had only had one anal orgasm before, and I couldn't believe that my next one was about to happen. My eyes rolled back in my head as his cock pushed me over the edge into orgasm. I shot my load all over myself as he pumped in and out of me. It must have turned him on because I felt him start to pump harder. His cock started to spasm as he shot his cum deep inside of me. I loved the feeling of his hot semen filling me up.
He lay down next to me, and put his arm around me. "I'd like you to stay the night if you'd like," he said.
"Oh yes I would," I told him.
We kissed some more, and talked a bit as we lay there naked on the couch. We fell asleep together, and the next morning, I woke him up and told him I had to go.
"When will I see you again?" he asked.
Music to my ears! I told him he could see me again whenever he wanted. "I had a great time last night," I assured him.
We agreed to get together again really soon. Was this the beginning of a new level in my femininity? Would Greg become my first boyfriend? It was a fantasy I wanted to explore more of, and I hoped we'd get the chance to do some more exploring soon.
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<a href="http://www.lushstories.com/stories/crossdressing/a-great-date.aspx">A Great Date</a>