***FYI***
This is a bit of a transition chapter, so please bear with the details. Thank you guys!!
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Trish and I had settled on a local Italian food restaurant. I decided to go the gentleman route and offered to pick her up, which she accepted. It had admittedly been a while since I had gone on a date. I put on some cologne (from the one bottle I had) and I wore my nicest shirt, which was a polo. Needless to say, I was fairly ill equipped for the dating world. I figured I would have to update before too long.
On my way over to her apartment, I started feeling the nerves, but not the nerves one might normally feel on the way over. Trish was beautiful, but the last girl I had hung out with was Brenda, and just recently I had been... closer to her, for lack of a better term. Brenda had probably the biggest breasts I had ever seen in person, and although I never considered myself a chubby chaser, I would be lying if I said I wasn't thinking about her chest every other minute of my day. As of late, she had been bringing me closer into her life, and apparently with that came some close encounters with her breasts. Unfortunately, I had overheard her mentioning that she needs a bigger guy than me (in multiple ways, but penis size specifically had come up), so a relationship with her seemed unlikely.
Trish was waiting outside of her apartment, in the parking lot. Well isn't that convenient. She was pretty before, but all dolled up, she was gorgeous. Her blonde hair was perfectly wavy, and her model esque physique should give me pretty major bragging rights. She got in and we hit it off right away.
"Wow you look fantastic," I said, shaking my head. "I'm gonna have to try a little harder."
She laughed. "Thank you! No, you look great. We're going to be the talk of the town!"
We both laughed. We made small talk all the way up to the restaurant. She was working as a barista at a local coffee shop. She said the pay was low but the tips were pretty decent. We talked about the party, and how much fun we had. We glossed over my "event" with Brenda's breasts, which was definitely for the best, but otherwise we talked about the whole thing. Some of it was a little bit hazy due to the alcohol, but we tried to piece it all together.
We shortly wound up at the restaurant and took our seats. So far, I felt it was safe to say the date was going well. I finally got to sit across from her, which was cool. She was very attractive, so it was nice to have a consistent view of her. Despite her beauty, I found myself slightly disappointed at her small chest. She must have been an A cup, which would have been perfectly fine with me if not for my recent experiences. I just had something in me wanting... more out of a woman. I shook off the feeling though. Come on man, I thought to myself, this chick is a 10. You would brag about having her as a girlfriend.
"So, am I your type of girl?" she asked me.
