The Worst Date 18 min read

written by Unknown author
original source of the story was Unknown source

If you’re just an ordinary single guy going to a friend’s party on the weekend, the temptation to meet a female there may arise. Or maybe it won’t. It probably did for Jason Grant, too, when he went to Barry Ryder’s party on Friday night.

Oh, sorry, I’m rambling. Let’s take it slower. Jason Grant was a 25-year old single guy with a great life, something that’s rare for a single guy. He’s been divorced for 5 years, and he has no kids. His friend, Barry, threw a big party at his house on Friday and invited a bunch of his closest friends… not to mention many beautiful women!

The date was Friday, March 26, 1999. It was 7:10 p.m. and Jason was heading to his friend Barry’s house for the gathering. He pulled his beige BMW into the driveway, amongst the dozens of other cars in front of Barry’s house.

In the house, Barry and his friends were chatting, laughing, dancing to loud music, drinking, and playing games. The doorbell rang and Barry opened it to see one of his best buddies, Jason.

Barry greeted, “Heeeeey, it’s about time! C’mon in!”

Jason was amazed at all the people Barry had in his house. “I tell ya, Barry, you know how to party!” he commented.

“Well, tell your friends!” Barry joked. “Food and drinks are in the kitchen, you know where that is. Make yourself at home, you’ll have a great time! I’m sure you know many of these people.”

“Thanks!” Jason said. As he headed toward the kitchen, he was stopped by a few people he knew as well, and he greeted them also. After making a run to the kitchen for food, Jason made his way into the massive living room with a plate full of snacks and a can of pop – he wasn’t a heavy drinker. He was just a little uncomfortable here since most of the people were close friends of Barry’s but not Jason’s, but he found that he was able to converse well with them.

After about 15 minutes, Barry came up to Jason, saying, “Hey, Jason. That gal over there, in the red dress…”

“Yeah?”

“She’s hot for you.”

Jason replied, “Oh, give me a break!”

“I’m serious, man. She’s looking at you.”

“I hate to ruin your fun, but I didn’t come here looking for a date. Just to have fun! I’m not ready to burden myself with another woman,” Jason exclaimed.

Barry gave him a surprised look. “You’re lying, right? Don’t you remember her? That’s Cynthia Hart! I tried to get you two together a few times.”

“She does look familiar,” Jason admitted. “Alright, I’ll talk to her. Just don’t expect anything. I’m only here to mingle.”

“Yeah, you say that now. I’ll bet you $50 she’s going to -”
All of a sudden, Cynthia approached. “Are you talking about me again, Barry?”

“Of course I am!”

“Oh, How sweet. And who is this?” the woman said, pinching Jason’s rear.

Jason muttered, “What the -”

Barry said, “This is my pal, Jason. I think you met him once. I almost introduced you to him a few months ago. But you know, you were going out with someone at the time.”

“Oh, don’t worry about it,” Cynthia said. “I’m always up to meeting new people.”

“Well, I’ll leave you two alone for a while.” Barry walked back into the small crowd. Jason motioned him to get this lady off his back, but it was too late.

She held out her hand. “I’m Cynthia Hart.”

Jason took her hand and was mesmerized by her pretty face. She had long, flowing brunette hair and big brown eyes. Her perfect figure was complimented by the red dress and black high heels she wore. She was absolutely stunning!

“Very nice to meet you,” Jason said, taking her hand to his lips. “I’m Jason Grant.”

“What a charmer!”

Jason had to admit, he was a little shy. It’s been a long time since a woman showed so much admiration for him – or seemed to. “I just couldn’t help notice how beautiful you are.”

Cynthia blushed a bit. “I get told that all the time.” The two began walking.

“Is that bad?”

“Not at all. It makes me feel good about myself, being told that. It gives me a sense of power.”

“Power? What kind of power?”

Cynthia said, “Never mind. So how long have you known Barry?”
Jason paused for a second. “About 10 years. What about you? I mean, where’s your date?”

That’s when Cynthia’s smile slightly faded. “I’m…I’m here alone.”

“I’m sorry.”

“That’s alright. The guy was a jerk, I didn’t need him. There are so many obsessive men out there. You’d be surprised.” Cynthia said. “Hey, these people are getting loud! Wanna go somewhere private?” Cynthia offered.

Jason nodded. The two went to one of the guest bedrooms, peeked around, and went in, closing the door.

Jason flipped on the light switch, sitting on the bed. He stared off into space as Cynthia sat beside to him.

“You know, Jason,” Cynthia said, “I have a confession to make. I heard Barry talking to you about me, and…well, please don’t be alarmed by this, but he’s been trying to hook me up with you for a few weeks now.”

He didn’t say anything. He just smiled a bit and listened intently.
She continued, “I know we’re total strangers, but he was just telling me how great of a guy you are. And he was right.” Cynthia squeezed Jason’s arm and snuggled up to him. “I like you.”
Jason was flattered, “Wow. How do you mean?”

“Well, you’re very good-looking, and you seem like a great person. I’m serious, I’m not kidding. And don’t go thinking I’m drunk or something, and I hit on every guy I meet. I don’t. I’m very serious about my decisions and my taste in men. I’m not flirting.” There was a pause. “Am I making you uncomfortable?”

“No,” Jason replied. “It’s just been a while since I dated anyone. My wife left me 5 years ago. It’s so hard now.”

The two strangers’ eyes met again. “I’m sorry,” she whispered. “You look like such…an honest guy. How could she?”
Cynthia wanted to kiss him, but she didn’t want to drive him away. She gave Jason a few light pecks on the cheek, then whispered, “Are you okay?”

“Uh-huh,” Jason muttered, closing his eyes. “You are so nice.” Cynthia’s kisses made Jason feel so at ease, he just wanted to lie down on the bed and pretend he was sleeping with her.

“I just didn’t want to scare you or anything,” she said.

He smiled, “I know. I admit that maybe I’m overwhelmed, but overall, this is very nice.”

Cynthia leaned on Jason’s shoulder as he lay on the bed, saying softly, “I was hoping that you know, maybe if you were up to it, you’d go out with me once.”

Jason opened his eyes and stared into hers. “I’d like to. You wanna leave here?” The two smiled as they stood up and left the bedroom.

Jason caught up with Barry in the living room, who was in conversation with Doug. “Hey, Barry, I’m going to hit the road. I’m a bit tired, and I really don’t know anyone here.”

“Hey – no problem. You take care! Oh, wait a minute…” Barry pulled Jason aside. “Take your time with her. She looks really good on you.”

“Take my time? She’s already making moves on me!”

“Hey – I told you she was crazy for you!” Barry said. “See ya later! Have a great one.”

“You too!” Jason said. Just then, Cynthia took him aside as well to talk to him.

“Hey, listen, I’m going to stay here for a few more hours. Are you busy tomorrow night?”

Jason replied, “Tomorrow? No, not at all. Why don’t we meet at around 7 or 8?”

Cynthia agreed. “That’s fine. You have a good night. It was nice meeting you!” The two shook hands as if they had just met all over again.

Ten minutes later, Jason arrived at home. All he could think about was the beautiful girl he met at the party, and he looked forward to the next night when he would finally be alone with her. It just seemed so strange that the two may have met a few times, but Jason couldn’t recognize her. It seemed even more peculiar that she was so attracted to him. Jason believed he made the right decision to follow up on this new friendship.

The next night 5:15 p.m., Cynthia called. She mentioned to Jason that she got his number from Barry and that she’d be stopping by in a few hours. Jason showered, got dressed, and cleaned the house as well. He wanted to make a perfect impression on her. No mistakes, no fumbles. This was his first real date – maybe – in 5 years!

Jason put a bowl of strawberries out on the living room table just for a night snack. He lit a few candles, tidied up some more here and there, and sat on the couch. Surely enough, when 7:03 rolled along, the doorbell rang. Jason calmly walked over and opened the door. In front of him was the lovely Cynthia Hart, dressed in a black leather jacket, red blouse, black skirt and stockings, glossy black high heels, and her hair flowing freely as usual.

“Wow!” Jason stepped back a bit and looked at her. “You are so gorgeous!”

Cynthia made her way in, flinging her jacket on the couch, “I thought you’d say so!”

“How was traffic?”

“Not bad,” she answered. “What’ve you been up to all day?”
The couple sat down on the couch. Jason answered, “Well, I’ve been bored. Looking forward to seeing you.”

“Well, now that we’re all alone,” she said, popping a strawberry into her mouth, “I have you all to myself. Nobody’s around to watch.”

Jason almost moved away, “Let’s just go slow, alright? I’m kind of nervous. I know you like me, but you have to realize, it’s been a while since I -”

Cynthia cupped his mouth, “Dear, relax! I won’t pressure you into anything.”

Jason looked down and smiled.

“What’s wrong?” she asked.

“I’m sorry, Cynthia,” Jason said. “I just want you to respect me. I mean, before you make any moves on me, I just want you to be sure about yourself.”

She asked, “You don’t trust me?”

“No, it’s not that,” Jason said. He began to touch her face, but he pulled his hand back.

“Why did you stop? I liked that,” Cynthia said. “You don’t have to hide your feelings.”

Cynthia snuggled up to Jason, rubbing his chest. “I can make you fall for me…literally.”

“What?”

She continued, “I’ve been known to possess a certain power over men, that makes them drool over my beauty and beg for me. Many guys can’t hide the fact that they think I’m so beautiful. I feel so supreme having a man at my feet, worshipping me, wanting to do anything for me. That’s the kind of guy I want, Jason.”

He started to tremble. “Well, you are beautiful, Cynthia.” He didn’t have the guts to remind her of her boasting.

“Don’t be afraid, love…”

Cynthia sat on Jason’s lap, snuggling her knee into his groin, causing him to moan just a bit. She put another strawberry into her mouth and held Jason’s face in her hands while she chewed her strawberry slowly and sensuously.

Jason exclaimed, “Uh, Cynthia -”

“Shhhhh…” she interrupted. Cynthia put her mouth onto his and caught him in a kiss. She tilted his head back and slowly let the chewed strawberry pieces slide from her mouth to his, letting all of the juice cover his tongue, along with the taste of her kiss. She passionately covered his lips with hers, trying to seduce him. Jason choked a little, and Cynthia finally let go, as Jason swallowed the strawberry. Cynthia smiled.

“Cynthia, that was just a bit too much for me…”

“Oh, Jason, come on! I bet I can make you all mine. Maybe I can even make you my slave,” Cynthia imagined.

Jason asked, “Wh – what do you mean?”

As Cynthia continued to rub her knee roughly into Jason’s groin, she explained, “You know what I mean. Imagine. Every morning I would wake up and you would begin the day by washing my feet. You would make me breakfast, lunch, and dinner. When I come in from the snowy weather, you would lick my boots clean, from ankle to toe to delicious sole. You would serve me all day, like a dog at my heels. Would you do all this for me…please?”

Jason hastily escaped Cynthia’s grasp, saying, “I gotta go!”

“Hey!” Cynthia jumped over to him as he got up from the couch, tackling him to the ground! He tried once again to get up, but Cynthia followed with a quick kick to the groin!

“Aaaah!” Jason fell to the carpeted floor, holding his groinal area. Cynthia covered him immediately with a shoe on his chest. Obviously, a quiet night alone was not what Cynthia had in mind…she was up to something.

She said, “What are you going to do, leave your own apartment?”

“J – just go, okay? Just -”

“I don’t think so, honey. You wanted me, and now you’re stuck with me.” Cynthia released the foot and sat on his chest, knees pinning his shoulders. She leaned down and kissed him again. This time, more passionately, more seductively, her lips all over his, making him want her more. After the kiss was over, Jason lay still, licking his lips.

Cynthia, rubbing Jason’s chest, softly explained, “Now, listen to me, darling. You can’t resist me now. I have you in my control, and you will obey my every word. You are my slave, and there’s nothing you can do.”

“Yes…yes, Cynthia…”

Cynthia stood up again, looking down at her new boyfriend. “I’ve never been able to defeat a man so easily. Now it’s time to play,” she said. “You will kneel for me, Jason, and put your lips to my shoes. Fulfill my fantasy!”

Jason complied and slowly turned onto his stomach at her feet. As he began to kiss the toe of her shoe, she stepped on the back of his head with her other foot. She kept the foot there as Jason kissed her shoe all over.

Cynthia smiled. “You’re not showing true devotion to me, Jason. I want you worshipping that shoe! Lick it!”

Jason quickly began licking the instep of her shoe. With one long stroke, Jason brought his tongue from toe to heel…over and
over, cleaning the leather.

“I’m still not satisfied, honey.” Cynthia pushed the toe of her shoe into his shoulder, rolling him back onto his back. She climbed on top of Jason’s body and stood on his chest, resting her weight on one foot. Jason was hurting under her high heels but got used to it quickly. He was totally entranced by her now…he couldn’t possibly feel any pain.

Jason muttered, “I’m beginning…to fall in love with you, Cynthia.”

“Liar,” she snickered. There was a slight pause. “Prove your love for me…” Still standing on his chest in her high heels, Cynthia began to push one shoed foot into Jason’s mouth as far as it could go. He was helpless.

“You like that, huh?” she asked. “Start sucking. I want to see that mouth moving.” Jason’s tongue roughly lapped her sole as if it were an ice cream cone.

She was proud of what she had done. “You worship me, don’t you?” Jason tried to nod, but couldn’t, with her foot in his mouth. She pushed her foot in deeper, and Jason moaned a little. Once her shoe was in his mouth as far as the main joint in her big toe, it could not go in any further. Jason almost gagged on the shoe.
She said softly, “How does this taste, Jason? What is the taste of expensive black leather?”

The high-heeled shoe plugged Jason’s mouth rather well. Cynthia, still standing on Jason’s chest, slowly pumped her foot up and down in his mouth, as if on a gas pedal. She would still occasionally wiggle the foot harder into his mouth, literally trying to force her shoe down his throat. Jason moaned louder, practically eating her shoe.

“Like it, honey?” Cynthia continued to pump the foot up and down while still standing on his chest. Tears of pain filled Jason’s eyes as he diligently sucked on Cynthia’s shoe-covered foot, licking her sole hard at the same time.

While Jason sucked on the shoe, he lifted his hand and held the heel of the shoe steady.

Cynthia was angry. “Did I say you could touch my shoes!? No touching!” She then shoved her foot down hard and heard his muffled scream as his body jerked in pain. Could she have knocked some teeth out? Who cares? She knew she hurt him somehow, but she wouldn’t let go.

After 30 more seconds, Cynthia finally stepped off Jason’s body and pulled the shoe out of Jason’s mouth, slowly. He gasped loudly for air and caught his breath. There was also a dark red heel mark on his upper chest.

Jason grabbed Cynthia’s ankle tight, begging, “Please, Cynthia… don’t stop. I need more… please give me more!”
“I love hearing my men beg for mercy.” Cynthia slipped off one shoe and rested a stockinged foot on his face. “You will begin sucking my toes, and you will suck them hard!”

Jason was weary, and he was beginning to pass out from the sweat of Cynthia’s foot.

“Hey! Wake up,” Cynthia shouted. She tapped his cheeks repeatedly with her sole. “You will be awake when you worship me! I want you to enjoy this.”

Cynthia didn’t give him a chance to speak as she vigorously shoved her foot into his mouth. “Continue sucking!”

Jason gagged but obeyed. Cynthia forced her foot as far as she could into his mouth, although the foot didn’t go in as smoothly as the shoe did. Jason sucked her toes like a baby sucking his thumb, trying not to slurp, enjoying every bit.

Cynthia said, “Oooooh, Jason, I never knew this would be so much fun! You make such a good slave for me. This is what I need, every day of my life. You would be perfect. Besides, Jason…I am a woman. Your job is to worship me!”

She was obviously proposing marriage. But even if she hadn’t seduced Jason the way she did, he would have rejected her. He just wasn’t ready. Either way, he had no choice in the matter, since Cynthia has had him at her mercy for 20 minutes now, forcing him to worship her. Jason continued sucking her whole stockinged foot obediently.

“You will remember this taste,” Cynthia said. “You’ve never known anyone as sexy, as erotic as me, my love. I’ve completely dominated you and forced you to worship me. Oooooh, what a rush!”

Cynthia moved her foot around in his mouth, jerking and shoving, trying to gag him, trying to shove the foot even further into his mouth, although it couldn’t be done! Jason’s body jerked under the pain of her foot, and his mouth expanding. His muffled screams only caused Cynthia to try even harder and harder – until Jason kicked hard, causing Cynthia to lose her balance and fall over!

“How dare you!” she yelled. She put her other shoe back on and stood up.

Jason bowed, “Cynthia, I’m sorry! You hurt me…”

Cynthia kicked Jason in the head, knocking him over. Jason must’ve still been under her spell because instead of calling the cops, he continued to beg for mercy. Cynthia had done well.
She put her foot out in front of him. “You will apologize to me and kiss my shoe. Now!”

Jason clumsily threw himself at her feet and opened his mouth onto her shoe, kissing the shiny black leather.

“That’s right, precious!” Cynthia encouraged. Jason grew tired and rolled onto his back to catch his breath from all of the excitement.

Cynthia knelt onto his chest again. She leaned toward his face once again. Cynthia slowly forced Jason into another passionate kiss, her lips locked onto his. When she finally let go and stood back up, Jason came to his senses. He was no longer under the “spell” she had put him in.

She touched Jason’s chin, whispering, “I had a lovely night, honey.” She then gave him a sudden kick to the groin, sending him down at her feet.

“Aaaaah! You witch…aaaahhh…” he groaned.

“I guess you can’t just trust anyone, can you?” Cynthia said, smiling down at him. She then blew Jason a kiss and casually walked out the door of his apartment. Jason was left there in the living room, kneeling on the floor from the pain. He had no idea what just happened between the times she had kissed him.

Jason didn’t know what to think about what happened tonight. He didn’t know whether he really loved her or hated her. But it didn’t matter. Nobody ever found out what happened between Cynthia and Jason that night, and how she seduced him, beat him, and forced herself on him. In the end, Cynthia Hart was just laughing behind Jason’s back. The only thing he could remember about her was that she was the worst date he ever had.

Leave a Reply

Your email address will not be published. Required fields are marked *