Diary 17: Sex With A Pornstar
Chapter 77
I was never one to try to get the number of a woman at work, I was usually too busy getting the job done to have time for flirting or chasing after her. I found a way to do my job and do it right, so when I started my new job I took the same approach. I worked hard and focused, it didn’t take long until I was given more and more responsibilities and became a leader at the company. But, one thing changed. This time it wasn’t just my work that got my attention, I couldn’t stop staring at one of my coworkers.
The woman was stunning, and she had a confidence that I found very attractive. It didn’t hurt that she was wearing tight skirts and low tops all the time. It got to the point where I couldn’t keep my eyes off of her, and one day she caught me staring.
“Can I help you?” She said while looking at me with a raised brow.
“Sorry, I’m not sure what you mean.” I played it off like I was lost in thought, not that I was just staring at her cleavage.
“Look, I know you’re staring at me and I think it’s pretty obvious why.” She said with a smile. “But, you don’t have to hide it, I don’t mind.”
I was taken back by her response. “Sorry, I didn’t mean to stare.”
“I told you it’s alright, besides, you’re not the first guy to do so and you’re definitely not the worst.” She chuckled at her joke. “My name is Lily by the way.”
“Mine’s Sam.” I replied while shaking her hand.
I couldn’t believe what was happening, one minute I was staring at her, and the next we’re making conversation. I didn’t know what else to say, so I just looked at her with a smile.
“Well, it was nice meeting you, Sam.” Lily said before turning and walking away.
I knew I had to take the opportunity, so I followed her. I walked up to her desk and placed my hands on it while leaning over her. “Would you like to go get dinner with me?”
Lily looked up from the computer and smirked at me. “I would love to.”
I couldn’t believe I had just asked her out, and even more, she had said yes. I had gotten a lot of the work done and was feeling confident in myself. I knew I would see her again, so I decided to be a man and ask her out. I waited for her to finish her work and then we left to go get food. As we walked out of the building, I noticed everyone looking at her and I couldn’t blame them, she looked stunning.
We talked for hours at the restaurant and learned that we had so much in common. We shared our hopes, dreams and our struggles, and by the time we finished dinner we were laughing like old friends. I drove her home and couldn’t help but feel a little sad that the night was ending. I pulled up to the gate outside her house and realized how nice it was. I got out and opened her car door for her before we walked to her porch.
“Thank you for dinner,” she said. “I had a really nice time.”
I could tell there was something in her voice, and I wasn’t sure what it was. “I did too,” I said. “So, would you like to do it again?”
“I’d love to.” She responded before kissing me.
I wasn’t expecting it, but I enjoyed it. She wrapped her arms around me and pressed her body into mine. I couldn’t help but notice how much smaller she was compared to me, she didn’t even come close to my shoulders. I ran my hands through her hair and pressed her closer to me. I was amazed at how good she tasted, it’s like I had been wanting to taste her all night. The kiss was amazing, but eventually, we pulled away. We stood there looking at each other and breathing heavily.
“Wow.” She said with a sigh.
“Yeah.” I agreed.
“I’ll see you at work tomorrow.” She smiled before opening the door and walking in.
I stood there for a second with a stupid smile on my face. I couldn’t believe it, we had just kissed and now I was walking back to my car. It felt like I was on cloud nine. The next morning, I woke up with a hard cock and thinking about Lily. I reached down into my boxers and wrapped my hand around it. I began to stroke myself, thinking about our kiss the night before. I imagined her soft lips on mine and the way her tongue felt on my own.
I reached down to my balls and gave them a squeeze before wrapping my hand around my cock again. I began to stroked faster and faster, imagining her wrapping her lips around it and sucking me off. I pictured her tongue running across the head while she deepthroated me. I started to thrust into my hand harder and harder as the image grew in my mind. She was sucking me good and had me thrusting into her mouth hard.
“Sam.” She said in a moaning voice. “Cum in my mouth.”
I heard her moan in my head and my orgasm shot out of me like a cannon. I came so hard that I collapsed back on my bed, I was breathing hard and could only think about her. The next day I couldn’t take it anymore, we were sitting at lunch when I whispered something to her. “Will you come by my house this weekend?”
She looked up at me and bit her lip. “Yes.”
I couldn’t wait, it had been too long. She walked into my house and locked the door behind her. I could hear her heels clacking on the floor behind me and then felt her hand wrap around my shoulder. She pressed her body into my back and placed her lips next to my ear.
“What can I do for you?” she said.
I couldn’t answer, the words weren’t coming out of my mouth. She reached down and grabbed my cock through my pants, squeezing it softly. “You want this?”
“Yes,” I managed to say.
“Do you want it in your mouth?” She whispered in my ear.
“Yes.”
I felt her reach under me and unzip my pants. My cock sprang out of my boxers and into her hand. I felt her soft warm hand wrap around it before she began to stroke it slowly. She pressed her lips on the back of my neck and sucked softly on my skin. I felt a rush of pleasure go through my body and I was sure I was going to explode soon.
“You like that?” She moaned in my ear.