My First Boyfriend

The next day, while Tim was busy at work, I spent some girl time with Anna, telling her about how things were with Tim.

"So, you want him in you, like...in your ass?" she asked me, once the conversation had inevitably turned to our sex lives. Anna had two or three friends with benefits, and she had some pretty kinky stories about what she did some nights. I was envious; she was out getting tied up and spanked, and I hadn't even let my boyfriend fuck me properly.

"Yeah...I want him. Totally. Have you...have you ever had a guy in your ass?"

"Last night, Saturday night, and last Thursday night. I love it. It feels so different form having a cock in your pussy. I can't really describe it to you, but you'll have to trust me. It hurts like hell the first time though. I even stretched myself out with toys before my first time." She winced. "Hurts. Like. Hell. But then again, so did getting my pussy pounded the first time."

I nodded. It would hurt, but he would understand. And the second time, it would feel better, and the third time even better after that. "Can you help me find something extra sexy to wear? I have a plan in mind."

And what a plan it was. Step one was dying my hair a beautiful shade of red. With my pale skin, it looked a natural fit. Step two was buying a new dress, snug over my round ass, falling just to the bottom of the curve itself. It hugged my breasts as well, too snug for a bra. It did have a little room in the front, so I could go without panties if I wanted (all part of my plan). I felt so naughty. It was wonderful. I did my makeup, then drove down to the recruiting office. It was still pretty early, before lunch, so I had time to wait. After about twenty minutes, Tim was left alone in the office. I tossed my hair back a little bit, giving it a little bit of a wild look, before walking in.

"Can I help you, Miss?" he asked. My head was turned, so he couldn't get a good view of my face. I dropped my voice slightly, asking to use the restroom. He pointed me in the right direction, and I snuck past him. That was the hard part. In there, I was able to peel my panties off, a thong with a magic eight ball triangle saying "Signs point to yes." Curling them up in my hand, I walked out, hoping he was still alone. I was lucky. Before he had a chance to see me properly, I walked up and kissed him deeply. He stuttered, and as he did, I snuck the panties into his hand. Only then did I let him see who it was.

"Samantha! I didn't recognize you! God, you look amazing." He looked down at his hand, seeing what I had put there. Reading them, he grinned. "Tonight's the night?" he asked, even though I'm sure he knew the answer already.

I blushed. "I want it to be," I said, swallowing hard. He looked around for a minute, making sure that no one would see him neglecting his duties. Then, he leaned in and kissed me hard, his tongue forcing my lips open.

"Then tonight," he said, leaning in to whisper into my ear, "tonight, I am going to fuck my girlfriend for her very first time." He nipped my ear after he said that, making me shudder in anticipation.