Being in your 20s is a strange time of your life. With the onset of adulthood you can’t help but face your distant but inevitable end, realizing it’s nothing but work and taxes from there on out.
Jack had his bucket list in mind. He wasn’t planning on dying any time soon, but he had a lot that he wanted to do so he figured he’s make a start after his 21st birthday. For this particular item on his list, however, he was going to need to request a little help from a friend. Particularly, a friend’s mother.
He walked up the flower-laden pathway to a cream door with a little frosted window to see Patty inside. They knew each other well, since he’d grown up with her son as a friend. She was a short lady with large breasts that always filled out whatever shirt or dress she was wearing, and she was probably the reason he turned out to be a boob guy.
“Oh, Jack! Hello!” She began.
“Hi, Missus Walker.” He answered politely, but bashfully. He knew why he was there, and it wasn’t a routine visit for his friend.
“Paul isn’t in right now, but he’ll be back later. Give him a call and see when he’ll be around.” Her voice was warm and reminded him of pie fresh out of the oven, a cold glass of lemonade on a hot day and all comforting, familiar things that are all too often taken for granted. She always seemed so genuine and pure, so matronly. That made it all the worse for what he was about to ask her. It’d taken him months to work up the courage to do this, but it was something that had to be done.
“That’s… I’m not here for him.” He started turning red as he came to the topic at hand. “I’m going to be entirely honest, I’m going to ask something… weird, ok?”
She tilted her head inquisitively. “I’m listening.” She still smiled. There wasn’t an ounce of judgement on her face.
“I have a bucket list, and… uh…” He stammered. “I want to … ah…” He couldn’t seem to find words delicate enough for her.
“It’s ok, just say it.” She said, putting a hand on his arm tenderly. He rolled his head back in resignation that he was actually going to do this.
“…I want to masturbate in front of you.” He grumbled quietly, but she heard every word. There was a slight pause as a silence broke between them. After a moment her warm smile darkened into a satisfied grin.
“Come with me.” She whispered to him, taking him by the hand and marching him through the house down into the basement. There was a little stage down there that she’d had built for the family and a karaoke machine that they busted out every so often. Nobody else was home but her, and she swiftly threw him up the stairs and rushed over to one of the sofas pointed at the dais. She crossed her legs and fumbled with a remote, turning on the overhead disco ball and coloured lights that washed over the stage.
“You’re going to give me a show, right? I’ve never had a personal stripper before. Should I get a pole fitted?” She giggled to herself. He wasn’t a stripper… this wasn’t supposed to be a show!
He was nervous; this was going far too well. He started to question if he really wanted this, but she was already wooping in her seat and cheering him on. “You have to dance!” she yelled over the song. “Show me those sexy moves!”
Jack couldn’t believe it. He wasn’t much of a dancer, but he started tapping his feet to the music and before he knew it his whole body was moving in rhythm with the music. He started lifting his shirt, giving her sneak peeks of what was underneath. It seemed from her reaction that she liked that.
“More!” she yelled, her beady eyes stuck on him, undressing him in anticipation of what was to come. He undid the button of his jeans and zipped down the fly, shaking out one leg and turning deeper shades of red with each article that he removed. Before the song was over he was there in nothing but his boxers. He could feel his cock swinging around visibly in the loose cotton shorts as he moved about and as he glanced over to her he knew where she was looking.
The embarrassment got to him, it was all too much too fast. He stopped his dance as the song ended and crossed his arms over his dick to attempt to hide the bulge, but she had already got an eyeful. He’d never seen her smile like this before. A huge, glowing grin was plastered across her face as she queued the next song.
“Don’t forget the rest; you have to do what you came here to do!”
It seemed like he didn’t have much choice. He turned his back to her and slid them down, kicking them off his feet over to her — right onto her face. She didn’t seem to mind, quite the opposite, she seemed to be really enjoying it.
Finally, completely red and almost fainting from the embarrassment, he gripped his cock and started pumping. The excitement of it all had already gotten him hard, he just needed to finish the show on a high note. Her glance kept moving up and down his naked body as he rubbed himself in time with the music, stroking harder and harder, squeezing his glans as she scrutinised every part of him with that satisfied smirk across her countenance.
As he reached climax she yelled and hollered her excitement as sticky globs of pearly white cum shot onto the wooden planks and dribbled out of his cock.
“You’ve turned into a strapping young man, you know. You don’t ever need to be shy now that I’ve seen you jacking your naked body.” She added with a wink. “And I’m keeping these.” She stuffed his underwear between her huge breasts. He didn’t have the gall to reach in there and take them back, but as he made his way home he wondered if that was what she really wanted.