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Date Night M/F (my first story)

WriteNow22

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Apr 1, 2022
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Hi gang! Longtime lurker, first time poster. I want to preface this entry with some warnings:

1. This is very sexually explicit. If that's not your thing, I get it. This is also a romantic story. Some people don't enjoy that, so you've been warned.

2. This is a fairly intense fantasy.

3. Sorry for any typos or rushed sentences. I wrote this at work (don't tell my boss) so I worked fast. This is also my first ever story, so have mercy please.

Now on with the show...




“Come on, sit still.”

In the back of his old Ford, Charlie Rogers had the brunette beauty Diana Daley in his lap, her infamous curls bouncing over her shoulders and grazing her ribs. He really didn’t want her to sit still at all. Every move of Diana’s bare hips against the lap of his jeans sent shock-waves through his core and into his cock.

“Sorry, sorry!” Diana huffed. She was trying to be a good sport. But the second Charlie had stripped her light sundress off and tied her hands to the grab-bar above his window, she had felt the familiar butterflies in her stomach, the ones that set flight every time Charlie had her alone in his truck.

This wasn’t the first time. In fact, every weekend of their ten-month relationship had been book-ended by trysts like this. Diana even knew what to wear; her flimsiest summer dress, no bra, no panties. They would just get in the way.

This Saturday, it took only six minutes for Charlie to get Diana from her front door to his lap, stripped and tied. At least they got out of the driveway today. Charlie had managed to park his truck amongst the brush on their favorite country road, where the night would provide perfect cover for the couple. Even if a stray farmer happened to drive down the pitch-black lane, they’d never spot the college students among the foliage.

Diana’s current position was easily Charlie’s favorite. He had tried everything on Diana – hogtied in the back seat, feet looped through the seat rests, even handcuffed and gagged in the truck bed. But the best by far was Diana stripped naked on his lap, her slender arms bound high above her head and her long, sleek legs wrapped tight around his waist. He could view everything from here; her full, bouncing tits, her tight tummy, the gentle curve of her tiny waist into her womanly hips. His eyes traveled up and down her body eagerly, taking in every inch with ferocity.

Diana certainly didn’t mind. Something about the hunger in Charlie’s gaze set her heart on fire with desire. Charlie was a looker, a stocky guy with thick hair and muscular, strong arms. A tight hug from Charlie was enough to calm even her worst nerves, and the soft touch of his fingers against her skin was almost addictingly pleasurable.

Charlie’s eyes had settled on his lover’s large breasts, and it took nearly all of his willpower to drag them away and look into her eyes. When he did, he grinned at her lustfully. “Ready, naughty girl?”

Diana bit her lip. She could feel her pussy growing wetter. Shyly, she nodded yes, and Charlie settled his strong hands into her sides and squeezed.

Instinctively, Diana squealed and jerked upward. The ticklishness of her sides was nearly unbearable, but the feeling sent waves of pleasure almost instantly through her body. Charlie smiled wide as the naked nymph in his lap giggled uncontrollably, twisting and grinding against him.

“What a ticklish little girl,” he teased, and an audible moan escaped Diana’s lips between her laughs. Charlie let his tickling hands linger in that sweet curve of her sides, feeling her sensitive spots twitch from his teasing. Then he dug his fingers in and crawled them upward, into the petite girl’s ribs.

“No! No!” Diana pleaded before the laughter overcame her. Charlie, of course, paid no heed. The two had an agreement. He knew that Diana’s desperate “no” indicated her helpless desire for more.

Charlie let his strong fingers torment Diana’s exposed ribs. He counted each one, playing among them like a boy playing with toys. He could easily lose track of time tickling her like this, watching her body writhe and react to every touch.

On their own, his fingers traveled upward, into the soft hollows of Diana’s smooth armpits. He knew his girlfriend waxed instead of shaved these days, making sure her skin was perfectly supple for their date nights. He also knew that poor Diana was cruelly ticklish on her armpits, and so he exploited her weakness, tickling deeply and purposefully.

With joy, Charlie watched Diana’s face gape with ticklish torment. Her eyes widened and then shut quickly. She tossed her head, her gorgeous curls flailing. Her mouth opened fully as the screams of tickle torture erupted from deep inside her chest. Still, Charlie could feel Diana’s legs tighten around his hips, holding him even closer while he punished her armpits.

For Diana, the tickling was far too intense to bear. That was part of the pleasure. The intensity, the sheer hopelessness she felt as her body was wrecked by the tickles made her pussy drip with lust. The ticklishness overwhelmed her mind and she could feel herself nearing the brink already, pushed almost to her edge from the torture.

“Oh, please! Please! AHHHAHA!” She begged. Charlie simply laughed at her; his licentious chuckles drowned by Diana’s fierce screams. He settled his fingers in for more torture, tickling even longer than he had planned simply because of Diana’s frantic reaction.

Diana couldn’t prevent herself from bouncing desperately on Charlie’s hips, her tits heaving and entertaining her torturer, her wet pussy drenching Charlie’s tightening jeans. She could feel her boyfriend’s erection between her legs, barely contained by his pants. The feeling of Charlie’s arousal only intensified her own pleasure, as well as her sensitivity. Diana could feel tears beginning to sting her eyes as the ticklishness racked her body.

“Wow, what a ticklish slut.” Charlie grinned at Diana, his eyes traveling between her bouncing breasts and her desperate face. “I’m never going to stop tickling you. You really need this, don’t you?”

“Please! Fuck! Please!” Diana begged. Charlie’s teasing went straight to her clit, igniting desire like she had never felt before. A chain of moans escaped her lips as Charlie continued his tickle assault, and she bucked her hips wildly against his, now more desperate than ever for the feeling of his cock.

Charlie allowed his hands to torment her bare armpits for a few minutes longer, before finally guiding them down Diana’s sexy body. His fingers settled around her midsection, one hand tickling her tiny tummy while the other crawled around her sides and hips, teasing and squeezing every delicious inch.

Diana’s screams transformed into girlish giggles and moans. Her tummy was a pleasure spot, both desperately ticklish as well as deeply erotic. On one of their first dates, Charlie had bound Diana and tickled her tummy for nearly six hours, watching with joy as she begged for more. He had only stopped when his bound tickle slave had been wrecked so deeply that she could no longer speak. Diana had chastised him after, pleading with him for even more tickling. Her next tummy tickling session had lasted nearly nine hours.

Charlie watched as his helpless girlfriend surrendered herself to the tickle torture. She bit her lip hard with pleasure until the giggles forced her to open her mouth wide again. She squeezed her eyes shut, grinding her hips hard against Charlie’s lap as his expert hands tormented every inch of her adorable tummy.

“Ooohh please…please…” Diana gasped and giggled loudly, her speech slurred by the sheer pleasure she was feeling from the tickling. “Oh fuck please…more please…”

Charlie couldn’t have stopped if he wanted to. Something about Diana’s ticklish skin was addicting to him. His fingers felt so at home on her sweet tummy, exploring the womanly curves of her hips and waist. One finger dipped into her belly button and Diana squealed. Charlie only wished he had twenty hands, so every sensitive nerve ending on Diana’s helpless tummy could be tickled at once.

The couple quickly lost track of time. As Diana rocked her bound body against Charlie’s throbbing cock, the two could feel themselves on the edge of orgasm. Charlie was hypnotized by Diana’s body, his desire to tickle becoming a need. He simply could not stop tickling, and Diana could not quench her desperation for more. Every minute Charlie spent on her ticklish body made her want an hour more.

Charlie finally allowed one hand to drift back up to his victim’s helpless armpits, then down her sexy back. Diana did not protest. In fact, she wanted it to tickle more. As tears dripped down Diana’s face and into her thick hair, she could only laugh and beg, “More…More…”

An hour ticked by. Then two. The tickling only grew more intense, and Diana felt her body submitting fully. She was breaking, and it was ecstasy. She wished Charlie would sentence her to a lifetime of this tickling, locking her in permanent bondage or maybe in a tickle machine, never letting the punishment end.

“You need this,” Charlie reminded her as he tickled, his tired hands unable to stop despite his exhaustion. “You deserve every second of this. What a ticklish slut. What a naughty girl you are.”

“I am…I am…” Diana barely choked through her laughter. Her pussy was impossibly wet, quivering with the desperate need to be fucked hard until the end of time.

“I need to punish you. I need to tickle more. Let’s add an hour. No, two. At least two more hours of punishment on your body.” Charlie was losing himself to the tickling, his mind melting with lust.

“More…More…” was all Diana could beg. Two hours would never be enough. She wanted a century of this, and more.

Charlie could not take his eyes off Diana’s bouncing tits. As much as his ticklish lover adored her tummy tickling, he knew those breasts were being neglected. Diana’s nipples were by far her most ticklish spot, so unbearably erotic for the poor girl that Charlie knew he could push her to insanity with just a touch. But nipple tickling would not be enough punishment for this desperate girl. Charlie had to make it tickle even more.

Without stopping the tickling on Diana’s tummy, Charlie reached down to his floorboards and felt around for his Home Depot bag. He finally found it shoved under the seat, nearly lost during the couple’s desperate romp. He fished it out and then felt it through the darkness, his fingers pushing past the rope and duct tape until they found the large, squared painters brush.

Charlie tickled Diana’s belly button as he repositioned himself, sliding his girlfriend down just slightly so that her pussy rested on his thighs. Then he slid the handle of the paintbrush between his legs, the long bristles facing upward, right into Diana’s dripping pussy.

As Diana desperately shifted her hips, the soft paintbrush dragged endlessly across her clit, flooding her body with a ticklishness more intense than she had ever felt before.

“FUCK! AHHH! YES FUCK!” Diana screamed as the soft paintbrush tormented her clit. She realized the hopelessness of her position. She could not prevent herself from rocking as her boyfriend tickled her body, but when she did, she inadvertently would tickle her own sensitive clit against the stiff bristles of the brush. This was evil, a truly cruel invention from the depraved mind of her lover. She loved it more than she could say.

Once Charlie was sure that Diana’s pussy could not escape the tickling bristles, he moved his skilled hands up from her tummy and onto her perky nipples. They were so firm, her full breasts putting them perfectly on display for him. Charlie let his thumbs graze those sensitive nubs for just a moment before he began to tickle intensely.

Behind her shut eyes, Diana saw sparks as the erotic ticklishness of Charlie’s touch overwhelmed her. She screamed, but the sound transformed into a deep groan in her throat. Her pussy practically gushed onto the tortuous paintbrush, pleasure and punishment arresting all her senses and driving her deep into all-consuming erotic torment.

Charlie grinned at her reaction. He had realized early on that the only pleasure his tickle-slut girlfriend deserved was forced ticklegasms. The Ler was more than happy to provide them, usually with his own tickling fingers but occasionally with toys and devices designed to abuse.

Diana’s ticklish nipples could not escape the strong hands of her boyfriend. No matter how much she bounced her large tits, she only provided a glorious visual for her tormentor. Charlie had been making Diana his tickle toy for nearly a year, and he knew how to contain her, trapping her in a state of constant torture.

Diana had no hope for escape. She didn’t want mercy, anyway. As she screamed with desperate laughter, Diana wished she could find the words to beg for more, but she had lost the ability to speak.

“Will you cum from this, tickle slut?” Charlie teased, his fingers gliding over those ticklish nipples hungrily. “Will this tickling make you cum for me?”

Not the teasing. Diana was so helpless to the low, growling sound of Charlie’s voice. She moaned at his words, eyes rolling back in her head. Her pussy grinded harder against the infernal paintbrush, intensifying the tickling even more.

“If you cum,” Charlie taunted. “I’ll tickle even more. If you cum, I’ll punish you all night.”

“Yes…oh yes!” Diana cried through her laughter. She humped the paintbrush harder, begging the bristles for more punishment.

“If you cum, I’ll never stop tickling you. If you cum, I’ll make it tickle so much more.” Charlie knew just how to tease her. His words slipped into Diana’s mind and made her heart pound against her ribs, melting her with desire.

“If you cum, I’ll tickle forever. If you cum, I will never stop. Cum for me, tickle slut. Cum for daddy. Cum from the tickle torture.”

With reckless abandon, Diana fucked the paintbrush with all her remaining the strength, the bristles absolutely torturing her ticklish clit. Charlie tickled her nipples as cruelly as he could, intensifying the punishment as much as humanly possible.

Then, with a loud and desperate scream, Diana’s body quaked as a ticklegasm was forced from her pussy, pleasure cascading through her bound figure as her mind disintegrated into ticklish ecstasy.

Charlie did not stop tickling Diana’s helpless nipples until every wave of her orgasm had fully crested. Then he finally had mercy, his ticklish assault stopping and his hands settling back on her hips. Charlie held Diana firmly, stopping her from rocking her pussy against the brush. Knowing Diana, she likely desired post-orgasm tickle torture on her clit. Charlie would give it to her soon enough.

The two caught their breath together. Diana’s desperate screams had finally ceased. Now the truck was full of their labored breathing and Diana’s last moans of pleasure.

Without untying her, Charlie held Diana and hugged her snugly. Diana melted into the familiar safety of her lover’s arms. Her head nestled against his chest, and Charlie’s face plunged into her neck, breathing the sweet scent of her perfume mixed with sweat. He kissed her gently, first on her neck and then on her sweet, full lips.

“Thank you,” Diana breathed into his kiss. Her eyes were still closed in ecstasy. “Thank you so much.”

“I’m not done with you yet, beautiful girl,” Charlie promised. He planted three more firm kisses on Diana’s delicious lips before he took her chin in his fingers and pulled her face upward. “I love you so much,” he whispered.

“I love you, Charlie,” Diana answered. “I love you.”

Charlie returned his lips to hers, and the two kissed passionately. Diana’s arms were still comfortably bound above her head where they belonged, but the rest of her was wrapped tightly around Charlie, clinging to him with passion.

As he kissed her, Charlie knew there was still so much he wanted to do to Diana. His cock was aching in his jeans, desperate to be inside her. And her beautiful feet, wrapped tightly around his waist, had not yet been punished. Thankfully it was still early; they had the entire night to play, and Charlie knew he had enough rope and duct tape to keep Diana captive forever.

Not that she would have ever tried to escape.
 
Well God damn, WriteNow22. That was an intense, powerfully-written story. Great job! You’ve got a talent for writing for sure. Looking forward to seeing what else you post in the future.
 
What an incredible story that centers around the Lee's tortuous pleasure! I'm with Primal, it's exceptionally written and I felt glued from the first on paragraph.
Thank you for sharing your gift.
 
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