The next day at dinner, I told mom that I would be hanging out with Ashley on Saturday. She said "That's great! Do you plan on...?" Before she finished, I said "Yes mom, I plan on wearing a bra." She said "Oh okay. What bra do you plan on wearing?" I answered "You know that white lace bra you got me last week?" Mom answered "Oh, the Pretty Polly bra?" I said "That's the one." She said "Ashley will love seeing you in that." I forgot to mention that the week before, I saw an ad on TV that our local department store had an announcement, stating that they were going to start selling Pretty Polly bras. I had forgotten about that brand, but as soon as I saw the commercial, I knew I wanted some.
So, I had asked mom if she could buy me some Pretty Polly bras, which she did. They all had lace and microfiber. The colors were black, white and pink. Anyway, mom then asked what color bra I was going to wear and I told her that I would wear the white one. She smiled and said "You really like that white one don't you?" I said "It's my favorite bra!" She said "Really? I thought my blue Playtex bra was your favorite." I said "it was, until I tried on the white Pretty Polly bra." She said "I see." Before I knew it, Saturday had come. I was so excited. I couldn't wait to put on my bra and go to Ashley's house. Just before I left, mom gave me a hug and said "Have a good time Cory."
I said "I will." After hugging mom, I walked the three blocks to Ashley's house. When I got there, I knocked on the door. Ashley opened it, gave me a hug and she let me in. When I got in, she smiled and said "I see you're wearing a bra again." I said "Yes I am." She asked "Can I see it?" I answered "Yeah." So, I took off my shirt. Ashley gasped and said "Cory, that bra is beautiful!" I said "Thank you. This is a Pretty Polly bra." She asked "Did you get it at the store?" I answered "Actually, mom got it for me. I saw the ad on TV a week ago, and I asked her to get me some, and she got me this one, a black one and a pink one."
Ashley said "Well that was nice of her." I said "I know it, but I'm not surprised. I have a wonderful mom." She said "Yes you do." All of a sudden, Ashley walked up to me, wrapped her arms around my waist and she started to kiss me. I gently pushed her off and said "Ashley, I'm wearing a bra." She smiled and said "So?"
I shrugged and said "Well okay then." We then went back to kissing. As strange as it was, me being a guy wearing a bra and kissing a woman, it all felt so right. It didn't even feel weird when Ashley unhooked my bra and took it off of me. I soon removed Ashley's shirt and bra and I got a good look at her gorgeous 34C boobs.
We stopped kissing for a bit and I said "Ashley, I love you." She said "I love you too Cory. I promise that I will do my best to make you as happy as you can be." I said "You already have." She said "Awww, Cory," and she gave me a hug. She then said "Why don't we go in my room?" I said "Okay." So, Ashley and I went into her room. I'm sure you can guess what happened after that.