Geoffrey is nineteen and has taken a summer job as a bike courier, hustling documents from one office to another. Near the end of the day, he makes a stop at his favorite stop — the office where Cassandra works.
Cassandra is a MILF through and through. At least twice Geoffrey’s age, she’s got the maturity and experience he craves in a woman, plus the fact that she has a bangin’ bod only adds to her appeal. He’s had more than one late night one-handed session thinking about her.
Just as he’s dropped off the package and is about to head on to his next stop, Cassandra steps out of her office and beckons to him. It’s almost like something out of one of those late night fantasies — she calls him into her office, closes the door, and talks about how he needs to do better to please her.
But it crosses the line from fantasy to reality when she closes the blinds and sheds her clothes.
Soon, Geoffrey is living out all of his wildest fantasies.
The Delivery Boy And The MILF is a 4,500-word short story.
I don’t have to look. I know that voice. Cassandra Miller, the office manager here. She is a banging hot MILF but intimidating as fuck. I always get both a boner and a shudder of fear every time we cross paths.
When I slowly turn to face her, I feel my dick grow hard and I struggle to suppress a shudder. Every damn time.
“Yes?” I squeak out. I clear my throat and try to deepen my voice. “Yes, Ms. Miller?”
She puts her hand on her hips, a position that makes the open neck of her button-up shirt stretch open just a little more, giving just a hint of the fullness of her cleavage. She’s absolutely gorgeous. Blonde hair cut just at her shoulders, smooth face, banging body, full boobs, and a hot hourglass figure.
I’ve jacked off many times while thinking about her.
“Come with me,” she says and turns on her heel, sashaying to her office door just around the corner from the reception desk. I watch her ass swing side to side in that tight black skirt of hers.
I try to look casual and hold the clipboard in front of my crotch and then hurry after her. When I round the corner to her office door, I find her waiting for me. I squeeze past her and she shuts her door. This is how some of my masturbatory fantasies have started — so it’s not helping me control my boner.
“Sit down,” she says in a tone of voice that clearly says don’t fuck with me, boy.
I obediently sit, secretly thankful for the momentary excuse to legitimately put the clipboard over my straining dick.