Dating a Married Lesbian
A young man finds the love of his life. There's just a few issues to get past.
Chapter 1
by
Themanliestdude
Alex Matthews was not a unique individual. He had a normal life, with normal parents and a normal sister. He went to a normal school, had normal friends, and decided on having a normal life. It's not that he tried to be boring, but rather circumstances kept forcing him to be boring. He tried to have unique and cool hobbies, like swimming, musical theater, debate, hell he even tried cooking at one point. But for one reason or another, nothing really stuck. He still had interests in all of these things, but the universe just never gave him the opportunity to hone any single one. Whether it was due to bad luck, or Alex's own inability to commit to one of these subjects, nobody was able to figure out.
Despite this, he still managed to get good grade and get accepted into a good college. But for most of his time, he just drifted. He choose to go into accounting because it seemed like a good stable career that he was good at and not because he actually liked the field or wanted to go into it. And he was good at it, to the point that some firms were trying to scout him. He was getting ready to have a quiet and stable life, but he didn't want it. At the end of the day, he was lonely 20 year old doing something he didn't want to do.
Which is why, when he was sitting alone at the bar, wondering what he was going to do to change his life (assuming he could do anything at all), he was a little surprised to see a woman approach and sit next to him. She was unsure how old she looked, and simply assumed that she just took good care of herself. She was wearing a large and snazzy looking dark blue coat that was covering most of her body, coming down to just past her knees. She had long brown hair, chubby cheeks, wore bright red lipstick, and had these piercing blue eyes. She was beautiful and looked as though she wasn't even trying. She was just being.
The woman smiled and looked over at Alex before speaking "Bad day?" she asked
Alex looked up a little confused. "Sorry, what?" he replied
"Oh, I'm sorry. You just looked a little down. I figured you needed a little pick me up."
"Well, I think my entire life needs a pick me up, but I appreciate the thought."
She chuckled at that self-deprecating comment, but still showed a little bit of concern as she kept speaking. "Wow, I guess you really need it, huh?"
"Well, it's not that my life is bad, it's just that I'm not happy." Alex explained
"You're not happy?" the woman responded
"I'm trying to be happy. I WANT to be happy. But I don't think what I'm doing is enough, and I'm not sure what else to do."
The woman paused for a moment and looked as though she was considering something. After a short while, she smiled at Alex and extended her hand out.
"My name is Angie. What's yours?" she asked
"Oh, sorry. Where are my manners. I'm Alex." Alex quickly answered while taking Angie's hand and shaking it.
Angie didn't let go of Alex's hand at first. Instead, she clasped his hand with both of her hands in a comforting way and looked Alex in the eyes. "You know, if you want something that can help with your problem of not doing enough, I think I have a solution to your problems. Would you like to take me up on my offer?"
"Depends? What is it?"
"I don't think I should share that with you in this crowded bar. My car is parked in the alley behind the bar. Do you mind if I tell you there?"
Alex looked at this woman and considered her words.
Should Alex take Angie up on her offer?
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A young college aged man gets dragged into the dream of many horny teenagers and struggles to figure out how to deal with what he has been offered.
Updated on Dec 18, 2025
by Themanliestdude
Created on Nov 26, 2025
by Themanliestdude
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