The Struggle Of The Baggy Shirt Returns.

The Struggle Of The Baggy Shirt Returns.

The struggle of the baggy shirt returns.

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1 year ago

My First Time

Not my first time ever. But my first time with a man that wasn’t my husband.

Let’s call him…… Cowboy.

I had been talking to Cowboy for weeks. Finally we both had enough time to meet.

We planned to meet before work. So that morning I made sure to take special care getting ready. But not too much, so that Mr. wouldn’t get suspicious. I dressed carefully in a skirt and loose low cut t-shirt for maximum access to my body, without removing clothes.

I was nervous all morning. Then I headed to our meeting spot. Imaging what was about to happen. I had already set boundaries. I just wanted to make out and touch. Without crossing the line.

The more I thought about it, the wetter my pussy became. It was throbbing by the time I got to our meeting spot. My heart was pounding in my chest and my fingers were shaking.

Once he arrived I invited him into my car. I’ll never forget the first words he said because they gave me butterflies. “Hey Pretty Girl” so simple, yet so alluring.

He was so handsome. His skin was soft, his eyes were bright and inviting and he smelled wonderful. And he was tall! One of my biggest turn ons is tall handsome men.

I don’t remember if we talked or what was said. But I do remember feeling his eyes wandering all over my body. Pretty soon he had his hands on my face pulling me in for a kiss. From there it got hot and heavy. That’s when we moved to the backseat.

The downside to making it with a tall handsome man is that he needs more room to move around and get comfortable. But we still had a lot of fun. He sat in the middle of the backseat and I straddled his lap kissing him passionately. Our lips fit together so well. He slid his hands up my skirt and moaned slightly as he squeezed. I kissed his neck and had my hands all over him.

He was telling me how beautiful I was and how wonderful I felt. How much he wanted to feel me from the inside. I pulled out his cock and started to blow him. To this day I still love his cock. It might actually be my favorite to date. At this point I was fairly inexperienced in blow jobs and I’m sure I didn’t perform well but his dick was so yummy!

He was getting close and at the time I was not going to swallow so I had my hand wrapped around his hard member and began to stroke and kiss him. I was kissing his neck when he said. “I want to be inside you so bad. But I know you’re not ready.” Which sent me over the edge. And I insisted I was ready.

I tried to climb onto his lap but he layed me down on the seat instead and slid his long firm member into my pussy. Which made me gasp. He filled me all the way and it felt amazing.

Before I knew it I was about to cum. My pussy tightened around him and I started to moan loudly. Pretty soon he filled my pussy with his hot wet essence. He continued to kiss me and we sat and talked for a while.

He helped me out of the car and wrapped his arms around my waist kissing my deeply. Stroking my hair. And we parted ways.

I had a huge smile on my face the whole day.

I would love the chance to see him again, and show him all the new things I’ve learned.

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