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, realising 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.
Pt. 2
It wasn’t over for Jack after his previous run-in with Mrs Walker. He was satisfied with having one thing checked off his bucket list and was already deciding what the next item would be; stuck between hitchhiking across the mid-west, or spending two weeks at a nudist camp. Mrs Walker however, had other ideas. Unbeknownst to Jack, she fully intended to take advantage of his generous previous offer and dropped him a text one weekend saying that she needed help with their hot tub. She made it quite clear he should bring his swim shorts, so he stuffed a towel and his shorts into a small duffel bag and made his way over.
By the time he reached the house he saw a shuffling coming from the curtains and a few moments later, before he’d even reached the door, Mrs Walker’s beaming face appeared on the other side.
“Come in, Jack dear!” She giggled excitedly. Her giddy manner instilled a sense of unease in Jack. She’d always been a pleasant woman but never before had she been this excited to see him. He stepped inside and removed his shoes, all the while feeling a burning stare coming from her. She was examining him, undressing him in her mind.
“Go ahead and get changed, the hot tub is out the back.” She went on. She hadn’t explained exactly what was happening but trusted in his nature that he would comply with her request.
Slightly confused by it all, he dropped into the little bathroom under the stairs and got himself changed. By the time he came out, the house appeared to be empty. He called out but got no reply, so instead waited out the back, clambering up into the hot tub. One foot at a time, he tested the temperature of the water but quickly found it to be a pleasant, fizzy warmth on his skin.
He looked around the tub, trying to figure out what might be wrong with it but Mrs Walker soon came out dressed only in a white bath robe. He couldn’t help but stare at the curves that lay beneath it, imagining what she must look like beneath it all. He never expected it, but somebody else walked out in a matching robe – Paul’s younger sister Samantha, who’d had her 18th Birthday just the day before. Jack hadn’t been invited to the party, but he’d heard that she was going out with her friends for the evening. As wild as that must have been, things were about to get even crazier for her.
She was a short, skinny girl with a tight body and straight hair that ran down her back. Growing up she’d always been a little shy and clumsy around Jack, knocking over things and running across hallways as not to be seen as best she could. She’d always had a crush on him, and in typical girl fashion didn’t know the best way to express it.
“Last time I helped you with your bucket list – Now I’m going to ask that you help me with mine.” Jack eyed Samantha more. She had a similar shape to her mother, short and curvy, and had inherited her biggest and best assets. Mrs Walker glanced over to Samantha. “And hers. I don’t think you got her a birthday present yet, did you?” Samantha looked away with a shy rosy colour flushing her face.
Mrs Walker grinned with an almost malicious glint to her eye as she spied beneath the bubbling water. “Take them off, Jack.” She instructed with no falter to her voice – it was a crisp and clear command. He wasn’t sure what he should do, but unable to think of anything else, he slowly slid off his shorts and placed them at the side of the tub. She grabbed them and tossed them into the garden without even looking away from him. “Can’t have you cheating, dear.”
The two females approached the hot tub and derobed to reveal skimpy bikinis that accented the sloping curves of their bodies and highlighted their plump rears and full breasts that squeezed out of the top of the fabric.
Jack’s cock rose with haste, swelling and filling, pulsing and tensing with an immediate desperation as they stepped up to the side of the hot tub, slipping their legs in and adjusting to the temperature. He couldn’t help himself but stare at their breasts bobbing up and down in the bubbling water, glistening in the sunlight as water glistened across them. Staring so hard, his nudity slipped to the back of his mind even if the embarrassment had not.
“I want you to do that thing again for me. You know, like last time.” Mrs Walker smiled, making herself comfortable and stretching out her legs in the tub. Sam’s eyes lit up – it seemed her mother had told her all about it. He’d really hoped she was going to keep it all a secret. If Paul’s sister knew, chances are he did too…
Turning an almost purple shade of red he gripped his cock and started rubbing his thumb against the ridge of his glans, unable to maintain eye contact as they stared with unblinking eyes.
“No, no. Stand up, do it properly.” Mrs Walker demanded. “This is like my CFNM videos!” Sam giggled as her eyes drew their way down his body as he stood until she stared right at his aching dick and thick fingers curled around it. She’d wanted this for a long time, but never had anywhere near the right amount of confidence to even imagine it to come to fruition. “Those are my favourite too!” Mrs Walker answered her daughter. It seems they had a very open, honest relationship.
Jack nervously stroked himself before them, every so often checking the fence to the neighbour’s house to make sure he wasn’t being watched by somebody else unintentionally. He could have sworn he saw Sam’s hand steadily slip down beneath the surface of the hot tub’s water and slide beneath her legs. He focused on her huge floating tits, hoping he could catch a glimpse of her hand from between the bubbles.
Running through his mind was an encounter with the two of them in a more intimate setting, though Paul might have a little something to say about that. His mind wandered to a threesome involving both of them as he squeezed and brushed his rod with an increasing voracity, faster and faster until he knees began to shake under his weight. Both the girls looked on with smiles permanently etched on their faces and insatiably hungry eyes as they devoured his body in their heads.
Jack noticed Sam’s nipples growing erect and pushing against the fabric of her top, every so often releasing little moans as her shoulder shifted and jerked. Her bottom lip pinned itself between her teeth as she looked on and Jack got fully into the swing of it at her enjoyment, pointing himself in her direction as his prostate seized up and cum shot from him in her direction.
For a few more moments she still rubbed at herself until her head dropped back briefly, her eyes closing and a look of satisfaction covered her face. He couldn’t help feel like the typical gender roles had been reversed here, that he was being objectified and scrutinised as men typically would a woman, that he was just a piece of meat for them to enjoy and savour until they were done with him. As his cum floated in the bubbles atop the water, he expected now was about the time they were going to be done with him.
Mrs Walker clapped. “Good show. Now go and fetch your trunks, go on.”
The realisation of what he’d done came to him in a wave and he turned bright pink as he attempted to cover what they’d already seen, stepping out and running across the lawn to collect his decency. They both watched as everything flopped around and his butt cheeks jiggled with each jogging step.
“Let’s invite him around again.” Sam giggled.