Carrie blushed and shyly looked away. Still, she didn’t let go of my manhood. She slowly stroked my dick over my slacks, and after a while, she seemed to have gotten comfortable with touching it.
We kept on kissing, but she didn’t let go of my cock. If I didn’t know any better, I’d say she was just as curious about me as I was about her.
Chapter Four - Carrie
The night was going better than I had expected. Jackson, the man who bought my virginity, sent a car to pick me up from my apartment. It was an offer I had gladly accepted since car problems were what got me into this mess in the first place. I felt excited as I dressed, but I got into that town car, unsure whether or not I was willing to lose my virginity to a stranger.
When I got to Jackson’s house, I was amazed. The word house didn’t seem befitting to the fabulous, gorgeous, and expensive-looking estate he had. However, when I met my host, my jaw really hit the floor.
Jackson was a tall, well-built man with crystal white teeth. He was much younger than I expected and also much more attractive. The dark-haired man could be a model with his square chin and full lips. A t-shirt and a pair of slacks that looked both comfortable and expensive clung to his frame. It seemed like he was in his forties, right about twice my age — something about our noticeable age difference completely turned me on.
My buyer looked like a guy with a lot of experience with women, so I knew right away that I would be in good hands.
As the evening went on, he pushed me against his living room wall, and I got scared. I didn’t know what to expect, but then he planted a warm and gentle kiss on my lips, and I just couldn’t resist. I found myself wondering what I had been waiting for all those years. Making out with Jackson felt amazing! I loved the way he gently but firmly pressed against me when we kissed, and there was something about his scent that made me want him even more.
A few minutes into making out, I felt his hard-on press against my tummy, and I got a little scared again. Jackson must have seen my fear because he went on to explain what it was. I mean, I knew what a hard-on was. I was a virgin, but that didn’t mean that I lived under a rock all my life. I had watched a few porn videos online before just out of curiosity, and there are a lot of hard dicks in porn. However, I thought it was nice of him to try and explain what was happening.
I loved that my host tried to make me as comfortable as possible. He told me what to do, where to touch him, how he liked being kissed, and I liked that he gave me some direction. It eased my anxiety.
Jackson’s hard dick made me feel almost faint, a way that I had never felt before. My panties got wet as he continued to push against me, kissing and touching every inch of my body. I quivered a little when he guided my hand to his dick, and I could touch the full length of his manhood. His cock felt huge and hard, which got me excited and scared at the same time.
“It’s too big,” I whispered after stroking it a while.
Jackson chuckled then kissed me on the neck, sending shivers down my body. “Don’t worry, Carrie,” he whispered into my ear, “it will fit.” My knees felt weak at his words.
I looked across the room and saw our reflection in the mirror. We looked perfect together. Jackson’s house was full of mirrors, and they reflected the firelight, making the situation feel almost like a dream.
“I don’t even know you,” I whispered. It was almost as if I was trying to get myself out of the situation, but I just wanted us to move a little slower, to be honest.
He stopped kissing me and pulled back. “You know my name. But it’s okay to call me ‘sir’ if that’s what you’re comfortable with.”
Everything about this wealthy man was intriguing. I liked how he was polite and didn’t want me to do anything I wasn’t comfortable with. It made me feel safe. I decided to refer to him as sir. It sounded more respectful; plus, I was already used to it, being raised in a military family and all.
“Can I keep kissing you?” he asked for permission. My date didn’t seem like the kind of guy who would ask anyone for permission to do anything. I knew he was making an exception. That really turned me on.
“Yes, sir,” I said with a smile.