It has been a while since I went out on a proper date. Most of my fucking has been with sex buddies. Tonight was an actual date I needed to get dressed for! I had no clue what to wear for an actual planned date with a new man.
I didn’t hear my stepson come home from school being in the middle of deciding what to wear. He hugged “hello” and then asked what I was doing. I explained I had a date but I was clueless on which way to go. He was very sweet and we had a talk. He said he is glad I am dating but that things have changed a lot since I dated before I married his dad. I knew he looked at his hot teachers so we talked about just what made them hot clothes wise.
He waited as I came to his room in my first choice. I was wearing a sundress with wedge sandals. I could tell by the way his nose kind of made a face that this wasn’t it. He sweetly explained the dress was cute, maybe too cute and definitely too long. The only thing he approved of was the little straps holding it up. I went back to my room and tried again. This time I wore an off the shoulder top with a shorter skirt and heels. He smiled and told me that was so much better. He really seemed to be giving good advice so I asked for more. Jason told me to roll up my skirt to show off my toned legs. I did till my ass was barely covered.
He asked if I had any push up bras which was adorable as he seemed shy but somehow knew a lot about lingerie. I bought several to his room and when he helped me pick one he turned around so I could change. He told me to explain what I was doing which seemed like an odd request. Suddenly he began to groan and turned around spurting cum all over his mommy’s chest. What a dirty little boy.
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