1. Business With Mom Chapter 1

    Date: 3/23/2024, Categories: True Stories Voyeur / Exhibitionism Incest / Taboo Masturbation / Toys Teen Author: Unknown Desire, Source: sexstories.com

    *Ding, the sound of the seat belt sign chimed as the captain made an announcement.
    “Ladies and Gentlemen, we have started our final descent into Chicago. We should be on the ground in about 30mins. We hope you enjoyed the flight as much as we did and we hope to see you again very soon, thank you!”
    As the stewardess passed through the cabin one final time to collect cups and all other trash, I caught myself sneaking in a little naughty peak as one of them reached over the seat in front of me. She was a long-legged blonde who I’d been fantasizing about for the past 3 and a half hours. She was maybe only a year or two younger than my mother who was sitting next to me reading the latest celebrity tabloid. I’m not usually attracted to older women but as a high school sophomore, honestly ever halfway attractive woman catches my eye.
    Hold on one second, let me go back a little. I’m going to tell you a true story (or at least how I remembered it) about a weekend business trip I took with my mother when I was 16 years old. A little about myself to start.
    My name is Chase, and like any other 16 year old boy my hormones were always raging. Anytime I would see an attractive woman wearing something that was revealing just a little bit of skin, that would be enough to get me thinking about the dirty things I would do to her.
    Funny thing is I was still a virgin...
    You could say I was pretty average in every way possible, I was about 5’9 at the time with average short brown hair and a little bit of muscle but not very much. Pretty average cock just a little over 6 inches but I was told by some of my football teammates I had a nice mushroom head.
    I played football but as you probably guessed I was pretty average. I lived a pretty average high school life up until that point. I’ve never had a girlfriend before but I did come very close to getting to second base with Stacy, one of the freshman cheerleaders a couple of weeks prior, at a party. She was a cute young blonde that looked a little too much like Torrance from Bring It On.
    Anyways, enough about my high school life. I wish I could tell a story about me fucking that long legged blonde stewardess in plane bathroom but that’s not the story, maybe another time. This story takes place on a weekend trip I took with my mother, we were headed up to one of her business conferences.
    My mom, Claire usually worked from home but sometimes would go out of state on business trips. I had been dying to go on one of these trips with her, since she was always telling me how great they were. She always would tell me how she got to stay in these massive 4 and 5 star hotels in big cities like New York and Los Angeles for up to 2-3 days at a time.
    Luckily for me one of those trips happened to fall on a weekend. So as you guessed I got to keep her company for 2 days while she worked. She gave me the choice to either stay home with my dad and sister or skip a day of school and go to a city I’ve never ...