Good Grief Ch. 05

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The Date has arrived.
2.7k words
4.72
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Part 5 of the 11 part series

Updated 10/30/2022
Created 06/05/2012
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Hello everyone,

Thanks again for taking the time and reading this story. I am overwhelmed with the positive feedback I've been getting. I hope to continue to entertain and engage you with the characters and their story. I have to give a special shout out to Honeybree for her editing, thank you girl! I'd also like to thank Alauman for reading my story early on and giving me the courage to post it.


They arrived at the small Italian restaurant and parked. Sienna noticed it was dead for a Saturday night. That's strange she thought.

"Isn't it weird that nobody is here? Maybe they're closed." Sienna remarked.

"No, I just rented it out for today."

"You what? But how, I was just with you this morning!"

"I'm good friends with the owner. He actually lives close to my mom's place in Brooklyn. So he agreed to let us use it for tonight." Jason said.

"Wow, this is amazing." She said.

They approached the restaurant and there were little white lights and candles everywhere. There was a quartet playing the violin, viola and cello in the corner.

A short portly man with gray hair and kind eyes in a chef's uniform came out with a big smile.

"Jason, my boy!" He said as he grabbed Jason and gave him a hug.

"It's good to see you Antonio, thanks for doing this for us." Jason said.

"My pleasure! And welcome to my restaurant. And who is this delectable creature with you?" Antonio asked.

"This is Sienna Johnson, Sienna this is Antonio Bianchi." Jason said as he introduced them.

Antonio kissed the back of Sienna's hand and said, "You are exquisite madam. If I were 20 years younger..."

Sienna smiled and said, "Thank you."

When Antonio wouldn't let go of her hand, Jason said, "Alright, alright enough with the touching, old man. She's spoken for."

"And you better make sure of it! Don't let this one go Jason." Antonio said. "Now...I've prepared some excellent dishes for you this evening so let's get you to your seat and we'll start you off with wine."

Jason led Sienna to their seat by placing his large protective hand on the small of her back. Jason's hand itched to go lower and he could tell from her curvy figure that she had much to grab onto. He had to focus and have control. He didn't want to pressure Sienna into anything she wasn't ready for but wanted her to set the pace.

But God help him, she was killing him in that dress.

The next couple of hours Sienna and Jason talked and ate the best Italian food they ever had. Antonio brought dishes upon dishes of superb food. He brought everything from seafood to specialty meats to different handmade pastas and sauces.

Sienna laughed and Jason loved to make her laugh. They teased each other and flirted. They finished two bottles of wine and were working on a third. Jason told Sienna that after dinner there was another little surprise around the corner.

Sienna thought that this was the best date she could ever remember having. They thanked Antonio and said their goodbyes. Antonio whispered something to Jason and Jason nodded. Sienna noticed but didn't say anything.

They walked down the block and Jason wrapped his arm protectively around her as she snuggled into his side. They were 'happy' from the wine but not quite tipsy, just relaxed.

When they got around the corner Sienna saw a white horse-drawn carriage waiting for their arrival. She couldn't think of anything more romantic. Sienna beamed at Jason and gave him a kiss. They got on and the driver gave them a blanket to keep their legs warm.

Jason pulled her in and kissed her fervently. Sienna moaned in his mouth and pulled his head closer to hers. Jason hands rubbed her shoulders and moved down towards her breast. Jason found her nipple and rubbed in small circles. Sienna moaned louder and encouraged him to continue his administrations.

Jason pulled the blanket up to their shoulders to cover them so they would have a little privacy to the naughty things Jason's hand was doing. All the while, Jason and Sienna's mouths didn't separate.

Sienna felt her pussy get wetter. She dreamed of this moment for so long. She felt Jason's hand go to her leg and slowly pull up her dress.

She shivered in anticipation.

Jason ran his hand up Sienna's thigh. When Jason found her bare pussy through the side of her panties, he groaned in her mouth. He slipped his fingers in her folds and pumped in and out. She was so wet and tight, Jason couldn't wait to taste her.

He withdrew his hand and broke free from the kiss.

"You're really wet for me baby." He pulled his wet fingers up and slipped them in Sienna mouth.

"You're a dirty girl aren't you baby?" Sienna moaned at the taste of her own juices. She couldn't believe the effect Jason had on her. She would've never done anything like that before.

Jason slipped his fingers in her pussy again and then sucked his fingers wanting to taste some too. She tasted so good; he planned on having fun tasting straight from the source.

Sienna's arousal was enhanced as she realized they were out in public, with only a thin blanket to cover them up and she let him have his way with her.

For some strange reason, Sienna didn't feel guilty about it. She trusted Jason, she somehow knew he wouldn't do anything to hurt her or cause her shame. So Sienna relaxed and gave herself freely to the moment.

Jason kept rubbing her pussy under the blanket when she was close; Jason whispered in ear, "I can't wait to pound your pussy with this dick baby."

Those words sent Sienna over the edge but Jason caught her scream with a deep kiss. Their lips and tongues dueled until Sienna came down from her orgasm. He thought he could detect a deep red flush on her skin. She was a vision to look at; with her half-lidded hazel eyes, cute nose, high cheek bones and swollen plump lips.

Maybe it was the whole day, the full moon or Jason but to Sienna it just felt right. "Take me home, babe." Sienna said. "I need you to finish what you started."

Immediately, Jason made the driver cut their ride short and he took them back to his car. By the time they got there, Jason was on high alert but Sienna was dizzy from desire. The thought of being with this beautiful woman had him all wound up.

As they drove to Sienna's apartment, they couldn't keep their hands off each other. When they got to the door, Sienna gasped at a large bouquet of three dozen red roses that lay by her door next to a medium sized white box. There was a note attached to the box that said "Enjoy!" Sienna figured that was what Antonio and Jason were whispering about in the restaurant. Sienna looked at Jason and gushed at him.

"Thank you, these are beautiful."

"Anything for my princess," Jason replied.

Sienna kissed Jason and he swooped down and picked her and the bouquet up smoothly. He didn't stop kissing her. And somehow managed to unlock the door with her keys, carry the bouquet, the box and Sienna all piled up together. Jason set the bouquet of flowers down on the table. They couldn't pay attention to anything but each other's mouths. He then walked towards the room.

"Bathroom." Sienna murmured on his lips.

"You have to go to the bathroom?" Jason asked confused.

Sienna giggled and said, "No, you're taking us to the bathroom."

"Oh ok. Where's your bedroom?" Jason asked.

Sienna motioned another door with her head which he acknowledged and resumed kissing her. He stepped through her bedroom door and set her down.

Sienna nervously looked up at him and smiled. "Where should I put this?" Sienna asked about the box she was carrying since she still didn't know what was in it.

Jason gave her a predatory grin and said, "That's for later."

He took the box from her and set it on her night stand.

"Take your hair down." Jason commanded as he backed up to lean against the wall watching her every move. Jason was now impossibly hard and wasn't shy about letting her see it.

Sienna shivered as she did what he asked. Her hair flew down past her shoulders in soft ringlets.

"Unzip your dress and let it fall to the ground." Jason continued.

Her unzipped dress slowly flowed off her body.

Jason groaned and started to unbuckle his pants. He kept staring at every inch of her as if memorizing each curve.

Because the dress had a plunging neckline Sienna wasn't wearing a bra. So there she stood in the center of her bedroom clad in only a tiny white lace thong.

She stood looking at him unbuckling his pants waiting for further instructions. Sienna licked her lips and felt herself get wet at the prospect.

He chucked his pants off and shoes off and started unbuttoning his shirt. Jason couldn't believe that this gorgeous creature was his. She was shyly clasping her hands in front looking at him with desire. Her full perky breasts were fascinating and inviting. Her large areolas and hard chocolate nipples looked ready to be sucked. She looked like a painting he wanted to sketch to forever remember her at this moment. Her small waist and tight stomach looked like he could eat off of it. Sienna's thick hips and thighs made him crazy with want and need.

"Turn around slowly." He whispered hoarsely.

As Sienna did this, she heard a gasp when he saw her ass in full view. Jason almost came in his boxer briefs when he saw those large round globes. Her tiny waist made it look even more appealing. He walked up behind her and let his shirt glide off.

Sienna felt Jason's hard muscles and dick on her back and let out a whimper. She felt her thong completely soaked. He bent down and kissed her shoulder and continued to kiss down her back. He hooked his fingers in her tiny thong and pulled them off. He could smell her arousal and was hungry to taste her.

Jason opened the box on the nightstand to reveal a Tiramisu dessert. It was Antonio's special recipe. Jason grabbed the plastic spoon that came in the box and scooped some up. He bent over and fed Sienna some on the spoon.

She moaned and said, "That's so good."

Jason turned her face to the side and tasted the dessert from her lips. "I agree. Have some more..."

While she was distracted with the dessert, Jason ran his hands down her soft mahogany skin as if memorizing every inch of her. She was so beautiful. How did he get this lucky?

Jason placed the spoon to the side and bent over so her hands where on the bed but she was still standing. He crouched down, planting soft kisses as he went. When he was face to face with her ass, he kissed it reverently.

His ass, his pussy he thought with pride.

He massaged her cheeks and pulled them open while Sienna was moaning and whimpering. He saw her glistening pussy lips and ass bud. He kept kissing and licking her from behind until his face was buried in her.

First he attacked her pussy with his mouth and moaned at the taste. His baby tasted so good. He twirled and laved her pink slit. He gave her clit a hard suck and she screamed and convulsed on his face.

He gathered her juices on his tongue and pushed it back towards her ass bud. He twirled his tongue around the tight anus bud and it caused her to jump. Jason stepped back and grabbed frosting from the dessert and put some on his tongue. He resumed sucking and drilling his tongue in her bud that soon she was pushing herself on his face. He smirked and pulled away.

She whimpered and let out a frustrated sigh. "I need you baby, please." Sienna protested.

Jason pushed two fingers in her pussy and started stroking in and out, strumming her clit at the same time. He continued to suck her ass until Sienna started vibrating and shaking. She was saying incoherent sentences. Jason pushed her over by clamping his fingers on her puffy clit and Sienna screamed his name when she came. She slumped over on the bed and was breathing heavily. She turned over, her back now to the bed as she saw him lower his boxer briefs.

Her eyes widened when his dick sprang out. It was thick and long, she guessed it was at least 9 inches long. He was so hard it was jutting up towards his stomach. She watched in fascination as he rolled on a condom and licked her lips.

"You taste better than I thought you would baby." Jason said. He crawled towards her and ran his hand up her thighs as he went. He opened her legs wider and stared at her pussy lips while he rubbed her clit with his thumb. He then locked eyes on her and ran his long dick down her pussy entrance gathering some more of her juices. He grabbed some more dessert and spread some over Sienna's nipples, under her breasts and her belly button.

Jason took his time licking and sucking the dessert off of Sienna's body with his warm meaty tongue. The sensations of the cold whipped cream and Jason's hot tongue were too much for Sienna, she closed her eyes as she was the verge of cumming again.

"Sienna, open your eyes. I want you to stare at my dick pounding your pretty pussy." Jason demanded.

Sienna opened her eyes and looked down at the joining of his dick and her pussy. It was mesmerizing to see her mocha colored skin adorned with pink lips and his tanned hands and purplish dick.

Sienna screamed as Jason inched his dick inside her for the first time. Her pussy felt so much better than in his fantasy. Jason and Sienna groaned together as her pussy suctioned his dick in, finally sliding it home.

"Fuck!" Jason huffed, as he was trying to remain in control.

Sienna tensed since she felt like she was being split open because he was so thick and large. When his dick finally bottomed out, Jason lowered himself and kissed Sienna passionately.

She moaned and relaxed into him. She felt herself get wet from his kisses. He massaged her breasts and teased her nipples. She gasped in his mouth and started moving against his buried dick. It felt so good to her now. Jason started to pick up the pace and was pumping his dick in her faster and harder.

It had been a while since he'd been with a woman so he wasn't sure how long he was going to last. He increased his pace and started panting loud breaths.

The sight of Jason's muscles flexing as he pumped in and out of her like a ferocious animal had Sienna wailing and meeting his every thrust. Keeping the pace, Jason bent over and latched his lips on her nipple and sucked hard.

Sienna lost control and yelled as she came on his dick. Jason pumped three more times and spurted his cum in her eagerly awaiting pussy. They were both panting and Jason slowly slipped out of Sienna.

He went to the bathroom and disposed of the condom. He wet a washcloth with a little bit of soap and warm water. When he returned, he lovingly cleaned Sienna's pussy and ass up while she closed her eyes in approval and drifted off to sleep.

He grabbed the box with the rest of the Tiramisu and put it in the fridge. He also found a vase for the flowers and placed them in with water.

Then he climbed back to bed with Sienna and spooned her. He kissed her neck and shoulder and ran his hand down the S-curve of her side. He loved holding her soft back on his chest and he loved feeling her plump cotton ass.

Like a truck that slowly parallel parks into a perfect spot, Jason happily tucked his dick between her ass cheeks and fell asleep as well.

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  • COMMENTS
25 Comments
AnonymousAnonymousover 10 years ago
good god

I'm a writer an the only thing I struggle with are sex scenes anytime struggle getting a good mental picture girlllllll. I come back to this story lol

D3stin2L0v3D3stin2L0v3over 10 years ago
Sheeeeeeeeeeeeeeeeeettttt!!!

I almost thought I was there!!!!

AnonymousAnonymousover 10 years ago
Amaze-Balls!

Girlfriend,

The imagery you weave........It's amazing!!!!!!

Nauti-Nymph

KittyOh48KittyOh48over 11 years ago
lovin it!

Oh please, let them have the fairy tale, they both deserve it! I LOVE THIS STORY!

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