Part One
Will had just turned eighteen. He would graduate in the spring if he kept his grades up. Right now, he was on the verge of failing two classes and one, English Comp 101, was a requirement for his High School diploma. He’d be in Summer School, again, if he didn’t pass.
He had been through a lot in his young life, or so he thought and maybe it was true, living with his stepmom Ellen, his real mom having passed away when he was only three and his dad skipping out on Ellen when he was just starting eleventh grade. Now as a Senior, he was feeling sorry for himself. He had developed a rebellious attitude, you know, teenage boy, know-it-all, disrespecting teachers, and sometimes Ellen too. He really did love Ellen as a mother, but his attitude wouldn’t let him show it.
Ellen didn’t know what to do about him. She could see his attitude changing since his father had left and saw his grades at school slipping from Bs and Cs to Cs and Ds. It seemed his only interest was hanging out with his friends, Richie and Donny. He would push the limits of the rules. Instead of being home at ten, as Ellen asked, it would be fifteen or twenty minutes after. When she asked him to do things around the house, he would take his own sweet time, or simply ignore the chores.
“I don’t know what to do,” Ellen said.
She was in the kitchen having coffee with Jannette, one of her co-workers, who had become her best friend. Jannette’s ancestors came to America from South Africa. She was a big woman, though not overweight, just one of those women with a strong constitution. She was almost six feet tall and weighed in at 162 pounds. For her size, Jannette, was a good-looking woman. She was well proportioned, breasts and hips nicely shaped but not too large and a slim waist and smooth soft belly. Being as tall as she was, her best feature was her legs. Firm, long thighs descended from her round hips and her calves were well defined and muscular. Her skin was the color of milky chocolate, smooth and soft.
“What seems to be the trouble?” asked Jannette.
“It’s Will,” Ellen replied, “He’s becoming a handful. He’s gotten a bad attitude, he’s not doing well in school and he runs around all the time with those friends of his, Donny and Richie. I never know what he’s up to.”
“Sounds like he needs a good whoopin’. Have you given him any punishments?”
“Well, I’ve tried, but he’s too big for me to spank, and grounding him doesn’t work, he just disobeys and goes out with those two boys, anyway.”
“I still say,” Jannette replied, “he needs to be punished.”
“I think so too, but how?”
“I think we can come up with something. I remember a few things my Grammy told me, might be able to make something work.”
Will and his buddies went out Friday night, even though his Mom had asked him to clean up his room and take his dirty clothes to the laundry room. Instead, as he’d been doing lately, he told Ellen okay, then promptly ignored her and left with Richie and Donny as soon as they arrived.
Ellen, not knowing what to do to make Will stay and clean up his room, shouted at him as he headed out the door, “Hey, I want you to be home by ten, okay?”
Will just waved, nodded and was gone.
He didn’t get home until 11:50. Ellen smelled the beer on him as he passed her in the hall on the way to his room. She didn’t say anything to him, but before she went to bed she texted Jannette.
The next morning Will slept late. It was almost noon when he came out of the shower rubbing his wet, sandy-blonde hair with a towel. He was glad he had put on a pair of his sleeping shorts because Jannette was standing just inside his door, leaning against the doorframe, her long brown, bare legs crossed. Will stood gaping at her, a bit shocked that she was in his room and looking like she did.
Jannette was dressed plainly but she looked so sexy. Will couldn’t help staring at her bare legs exposed below the hem of the thin cotton dress that just covered the tops of her thighs. Above the swell of her hips the dress snugged about her waist and tummy. Then Will eyes alit on her breasts, seeing that she was braless. He saw her nipples making alluring points in the fabric of the dress. She smiled slyly and gave a little nod of her head as she noted the movement at the front of his shorts.
He saw her smile and nod and it broke his stare. At the same time, he noticed himself and quickly moved the towel in front of his waist to hide his growing erection. He shifted his weight from foot to foot and felt himself blushing, his cheeks reddening and his neck flushing with heat as he wondered, why was this gorgeous, sexy woman in his bedroom.
“Wha...” he started but Janette interrupted.
“Your Mom” she was practically purring, “says that you’re being a naughty boy.” She posed for him, shifting her hips, left hand on her hip and her shoulders pulled back pushing her breasts out. Will was practically drooling and he was fully hard now, his pulsing erection jerking at the fabric of his shorts.
Will was just gaping at her so, she continued, “I told her I thought you needed a whoopin’. What do you think, bad boy, do you deserve a whoopin? How about you just lay on the bed there and I spank your ass. I think you’d probably like that, wouldn’t you?”
“Ah... er... well... no I don’t think I would,” Will was finding it hard to concentrate on the words.
“Oh, come on, it won’t be so bad. You lay there and I’ll give you a few nice smacks on your plump tushy and I can tell your Mom you’ve been punished and will be a good boy from now on.”
“No, I won’t do it,” Will protested.
“You know you deserve it; you were almost an hour late coming home last night. Not to mention this pigsty room and the attitude you’ve been giving your Mom these past few months.”
“Er... so, Mom’s been telling you about me?”
“Well, yeah!” Jannette sensed Will’s resolve was weakening and all she had to do was press him a bit more and he would accept this punishment. “Yes, I know all the naughty things you’ve been up to. You and I both know you need this spanking so just hop on the bed and let’s get on with it.”
“No, I won’t let you spank me,” he resisted.
“Will, you wouldn’t want the authorities to find out you’ve been drinking beer? Would you? You could be in a lot of trouble, not to mention whoever gave it to you.”
“Aah... I guess not. Well, if I let you, how many will you give me?”
She knew she had him now. He was already accepting he was going to be punished and it was only a matter of how much. “I think six should do it, if they’re good ones and not too easy. Okay?”
Will thought, alright, six swats, that would be easy enough to take, if it kept him out of trouble with the cops, and then he could get on with his day and besides he was starting to wonder what it would be like to be spanked by this sexy woman. He shrugged and went to the bed and lay down on his stomach. He lay watching Jannette, waiting for her next move. He was still hard, his erection pressed between the firm mattress and his muscular abs. Without thinking, he shifted his hips, rubbing against the bed. He blushed hoping she hadn’t noticed.
But she had and she grinned slyly to herself. This was going to be so much fun. “Scoot over here to this side of the bed so I can reach you.” Jannette ordered. Will did what she asked without question or comment. He just wanted this to be over.
Jannette admired the smooth young skin of Will’s muscled back. The knobs of his spine curving down to his pelvis were just begging to be touched, but she resisted, that was for later. She appreciated his slender waist and then there was the cheeks of his ass. Tight, young buttocks, tautly muscled, she watched them flexing under the shiny nylon of his shorts. ‘Next time,’ she thought, ‘will be without the shorts.’
Whack!
“Arrrrhhh.” Will jumped and bounced on the bed, really more in surprise than pain. But instinctively his hands flew back to protect his butt.
“Will,” Jannette said, in rather a stern voice, “put your arms above your head and keep them there or we’ll have to start over again.”
Slowly, he obeyed moving his hands overhead. He watched her closely, waiting for the next spank. The first one was starting to tingle on his skin and he could feel the warmth beginning to spread across his buttocks.
She raised her hand and started to smack him. He reacted instantly, and without thought, shifted a hand back to cover his ass. “I guess we’ll have to do something with those hands since you don’t seem to be able to keep them out of the way.” Jannette went and rummaged around in his closet and found, amazingly, half a dozen neckties. She took them and grabbed Will’s wrists and bound them together with one, then used another to lash them to the bedpost.
Will tried to protest but she hushed him telling him it was the only way to get finished with all six of the spanks. Otherwise, the count would have to start over every time he put his hands over his butt and they’d never get done.
“Okay, we’ll start again,” She said, “you ready, Will?”
“Uh,” Will nodded.
Smack!
“Arrrhhh.” Will’s feet folded up over his behind.
“Will! Okay, now I’ve got to fix those feet, too!”
Jannette went to the foot of the bed and reached over and grabbed his ankles. She pulled his legs to the footboard, stretching him across the bed. She proceeded to use more of the neckties to lash his feet. She put them atop the footboard with his bare soles pointed up and tied them about eighteen inches apart.
She went back around to the side of the bed. Will looked up at her. “You didn’t have to tie my feet.”
“But you couldn’t hold still. Now I don’t have to worry about you kicking me. And, you know, we have to start over, again.”
“Ohhhh,” he groaned.
On a whim, Jannette reached out and put her index finger gently into Will’s bare, exposed armpit. Will yelped loudly and jerked his entire body away from her finger. After a short pause, she reached across and touched her finger in his other armpit.
“Aeeeieee,” Will screeched and jerked wildly, squirming and struggling against the neckties holding him fast to the bed. “Stop that!” he cried.
“Well...” purred Jannette, “ticklish aren’t we! I have just the thing for that. Don’t go away, I’ll be right back.”
“Hey, where are you going?” Will shouted after her as she scurried out of his bedroom.
Jannette was back ten minutes later. Will had spent the entire time trying to loosen the ties imprisoning his wrists to the post of his bed. No luck, Jannette was good with the knots and he couldn’t reach them. She’d brought back a small tin container with her. The tin was a light blue color and had a swirly design around its middle. She unscrewed the silver lid and set it on Will’s night table. A sweet, slightly citrus aroma wafted from the tin.
“I have just the thing for you, Will,” Jannette said. “Right here in this tin I have a little creamy ointment. It’s a special concoction, mixture if you didn’t catch that word. It’s been passed down in my family from my great-great-granny. She’s from the indigenous people of South Africa, you know, they call themselves Khomani San. They lived mainly in the Kalahari region; you can look it up. Anyway, I think you’ll enjoy this cream.”
She dipped her finger in the tin and put a dollop in the palm of her hand. She rubbed her hands together and placed one palm on each side of his exposed rib cage. Carefully, making an effort to not tickle him, she massaged the ointment into his young skin. He still wiggled and squirmed, giggling and gasping, while she worked the ointment. Dunking her finger in the tin again, she used it to paint the ointment down the center of his back, following the crease and the knobs of his spine as a guide. More squirming and a little bit of giggling. She scooped enough of the ointment to coat the entire length of his spine. And finally, she used a small amount and worked it into the upturned soles of both his feet.
“Now, Will, we can continue with your punishment,” Jannette said. “But we have to start over so you still have six swats to go.”
Whack!
“Eeeeeaoooowww.”
“Oh, don’t be such a cry baby. You can take a few spanks, can’t you?”
Will glared up at her but didn’t respond to her taunt. He turned his head away to await the next spank, determined to keep stoically silent.
But the swat didn’t come. He waited, fidgeting, wondering why she didn’t get on with it, but not wanting to look at her or show his nervousness.
Jannette watched him. She watched the muscles twitch and ripple across his shoulders as he tried to anticipate the next spank. She watched the tensing of his buttocks under the silky nylon shorts. She watched his arms and his legs when he heaved against the neckties holding him fast to the bed. She began to imagine what it would be like to take him to her bed and screw his brains out. But he was her best friend’s step-son, screwing him might ruin their friendship.
Whack.
“Uuuooohhhh.” Will managed to only groan, smothering a yell in the sheets, while at the same time he felt his dick pulse between his stomach and the mattress. Geez, he thought, am I getting turned on by getting my ass spanked?
She climbed onto the bed and straddled him, kneeling, and sat on his butt. She reached over and got the tin of ointment from the night table. She got a dab on her palms and began rubbing it onto his ribs, again. He struggled, giggled and squirmed but the tickling sensations were, mostly, bearable. Until... she began poking him with her finger tips. Then she began tickling, slowly. Will went berserk.
He bellowed with laughter. He jerked and twitched. He roared and gasped for air. He yanked his arms and legs. The bed rattled and shook and bounced as he panted, laughed, giggled, he bucked and heaved trying to throw her off. It seemed to go on and on forever.
“Oh...” gasp. “Stop... please,” gasp. “No... pleeasssseee, stop,” gasp.
“Isn’t my Grammy’s ointment great?” Jannette teased. “What do you think?”
She twisted around and reached back and scraped her fingertips across his feet. She prodded between his toes and tickled from his heels to the balls of his feet.
“Hee haaaawww, please... stop.” Gasp, pant, gasp. “No more,” gasp. “Yoooowwwwwieeee... quit-it... aaaaaiiiieeee, paahleeeezzeee... stop... gasp.”
She went back to his ribs and armpits.
“Haa eeeehhhhh, no, pleasssseee... gasp-pant. “Stop... pant... pleessee... gasp... stop... gasp. Noooooo... gasp, no more, please, no... pant, pant, STOP... gasp.”
“Oh, alright.” She stopped tickling and got off the bed and stood with her hands on her waist, watching admiringly, while he panted and gasped, struggling to regain his breath. His chest heaved, ribs swelled and contracted, as he gulped air into his lungs. It was almost a full minute before Will’s breathing was getting close to being normal again.
“Wasn’t that fun, Will?” she asked, “You seemed to enjoy it.”
“No,” his voice still weak from lack of air. He sighed then spoke, “I don’t like being tickled.”
“Oh, but it’s so much fun,” she replied. “I figured you might get off on it. Let’s see.” Jannette rolled him onto his side and eyed the front of his shorts. “Hmm, well, looks like you’re right. You’re not so hard now, are you?”
Will flushed red, his face burning as he realized she was looking at his crotch, inspecting him for a hard-on. And she was right, he’d gone limp while she tickled him.
“That just isn’t right, I’ll have to think about that. Anyway, I guess we’ll have to finish the spanking, then.” She let Will roll back onto his stomach. “Hmm, you know I think I have something in my car we might be able to use.” Jannette patted Will on the butt and turned to the door. “Hang in there, I’ll be back in a sec.”
Will heard a smacking sound. He lifted his head and looked toward it and saw Jannette was back. She was slapping something into the palm of her hand. It looked like a... it was a paddle, covered with black leather that was sewn over something stiff and rigid and about two feet long. Jannette held it by the handle and was eyeing him with a leer.
“Four swats to go, get ready.”
Will instinctively tensed his cheek muscles and pressed his hips down into the mattress, attempting to get as far away from the wicked looking paddle as Jannette walked to the bed. She stood next to him looking down on his body and tapping the paddle against her palm. Amazingly, Will felt his loins stir. Oh, no, it couldn’t be!
Whack!
“Iieeeeeoooowwwww!” He yelped, and bounced on the bed, rattling it and struggling and lurching against the neckties holding him stretched. The pain was sharp but short as it turned into a tingling sting and then heat crept through his buttocks. He felt himself twitch and stiffen. Oh, God, was it true? Maybe so.
Whack!
“Oooooooeeeeewwww.” He yelled. His entire body locked in muscle spasms, rigid and taut, his ass quivering as the pain slowly melted into prickly heat that began to radiate through to his now stony stiffness. He was fully erect and couldn’t believe how turned on he was by the pain and heat of being spanked.
“Two more to go. I think we’ll have a little pause here. I can’t seem to keep my eyes off those beautiful feet of yours and I do so enjoy tickling young boys.”
“Oh, no, please Jannette, please no more tickling, please, please,” Will begged.
“But I have so much fun tickling you. Well, I’ll tell you what, I’ll let you choose. You have two more swats coming. If you don’t want me to tickle those lovely feet, then you’ll have to ask me, nicely, to keep spanking you and to start the count over again. What’ll it be? Tickling or spanking?”
Will peered up at her with pleading eyes. He made his decision quickly, “Please miss, no more tickling, please spank me, spank me six more, please,” Will begged.
“Alright, six more swats. Ready?”
Will nodded and buried his head between his outstretched arms.
Whack!
“Ooooooommmmh,” Will gritted his teeth to muffle the scream.
Whack!
“Aaarrrrrrrgggg,” Will groaned, wriggled and squirmed, heaving against the neckties restraining him to the bed. The pain of the spank flowed into him and he surged. He felt his ass beginning to burn and he was hard again. He unconsciously pressed himself against the mattress.
“I think you should be counting for me, Will. That was two, so, next time let me hear you shout it out, okay?”
Will nodded.
Whack!
“Aaaaarrrr, THREEEEE.”
Whack!
“Fooouuuurrr, aaaahhhh.” The bed rattled, the headboard banging against the wall. Will’s body shook and jerked, he pulled with his arms and legs but the neckties held fast. He caught himself bouncing against the mattress.
Smack!
“Ooooooohhhhh, F-FIIVE” Will figured his ass should be bright red by now. And it hurt, too, but the heat was building and he was as hard as he’d ever been. Not only was he hard but he thought he felt larger than ever. It was pushing up against the waistband of his shorts.
Whack!
“S-Siiiiixxxx, aaahhhhh.” Will bounced against the bed. His ass was afire. He was pulsing and throbbing and swelling. He was so close. He turned to Jannette, he eyed her lustily.
She caught his look, “That was all six, Will, it’s over, we’re done.” she said sweetly.
“Er, ah, but...” Will's voice was raspy and whiny, “I’m so close, Miss.” He began to beg, “P-please, please let me finish. Please, Miss, more, I need more, please.”
“WHAT?... Ooh, my word!” And then she understood.
Whack... Whack... Whack!
“YYYEEEEEEAAAH,” Will's climax erupted on the second swat, he panted, gasped and humped as his swollen, surging hardness pumped sticky cum into his shorts.
Jannette watched, she couldn’t believe what had happened. Then she knew it was true and smiled silently to herself, understanding it would wreck the moment, and him, if she laughed and so, kept quiet. She watched fascinated and silent as he climaxed, while he jerked and gasped, slowly, slowly settling back to normal, till his entire body drained of energy and he was completely spent. For a moment she thought he had passed out, but no, he was simply lying limply with his eyes closed.
Silently, she left his room. Not wanting to disturb him she left him tied to the bed, after making sure the neckties were not too tight. Jannette had triggered Will’s sexual fetish. Will had discovered it, too. She could exploit that secret, if she wanted, but wondered what it would do to him if she did. She would have to talk to Ellen and they would decide what to do next.