Introduction:
Once upon a time there was a woman named Caitlin. She was an intelligent, sweet, funny and sexy woman, but she was lonely. And, to be blunt, horny.
So the fair Caitlin put a personal ad on the Internet. The site is not important although it was not a “matched” or “harmonious” one. The ad read as follows:
“Funny, smart, cute, loving, playful, passionate, blond haired, gray/blue eyed (but they change color), chick. I am a smart ass. I am optimistic, independent, honest. I am a neat freak with “slob” tendencies. I am adventurous (in all things…wink, wink, nudge, nudge) with couch potato leanings. I like to think I am cool…but I know I am kind of a dork. Crafty, (because I knit, paint and make jewelry, etc…not in an evil villain kind of way). I am a movie freak and a book worm and a music addict. I love the beach (I collect shells and sand dollars) and the ocean and swimming pools and bath tubs, basically any kind of water. I really do love hockey and baseball (Go Cubs!). I have a brain full of useless (most of the time) trivia. Okay, that does not quite sum me up (but it comes close).
Looking for a nice, honest, guy to explore with or veg out with. I LOVE smart and funny guys. I LOVE smart asses (is that technically one or two words?). Looking for a guy who will laugh with me…and at me (I do have blond moments as my hair color is “real”). A guy who will share an ice cream cone or a piece of pie with me. A guy with a “lust” for life (and, ahem, other things). A guy who can love and/or laugh at my quirks (and there are many). A guy who is willing to try new things. A guy who challenges me, but is not afraid to be challenged by me. Must love to snuggle. Must be kind to animals and small children. Must have a desire to travel and explore. Must be SINGLE (there are a few Commandments I have no desire to break).”
Alas, the only men who seemed to respond spoke in “text speak”, could not spell or craft a sentence, were looking go a quick fuck or some dirty talk. There were even a few “married but looking” men who responded. Caitlin was dismayed.
But hark! One day a man put her on his “favorites” list! She read his profile. He was smart. He was funny. He was not bad looking. He could write a complete, grammatically correct sentence. And behold! He was over six feet tall (did she forget to mention she loved tall men?)!
“Huzzah!” she thought. But one day passed and he did not send her an e-mail. Another day passed and no e-mail. Day three: skunked again!! Day four was about to come to a close with nary an e-mail from this “Prince” so Caitlin decided to take matters into her own hands:
“Dear LustForLife: Why would you put me on your favorites list and then not contact me? Caitlin” She pushed send, turned off the lights and fell asleep.
Caitlin was very busy the next day and did not have time to check her ad until almost midnight. She turned on her computer and quickly got online to check her profile. Her eyes ran down the list of senders until, finally, they landed on a response from LustForLife!
“Dear Caitlin: I am sorry I did not send you an e-mail….”
She read the missive from LustForLife. He had meant to send her an e-mail but life interfered. He was starting a new business. His son was visiting from Illinois. He was glad she called him on it. He would like to know more about her. He signed it “xxoo, Chris”.
Caitlin smiled to herself and typed a response: “Chris: That was a very long answer to a simple question!! I would love to chat more. My phone number is 555-5050. Caitlin”. She pressed send, turned off her computer and turned off the light. Not 30 seconds later her phone rang. Caitlin looked at the number. She did not recognize it. Could it be?!?
“Hello?”
“Caitlin? Hi! It’s Chris!”
Two hours later Caitlin pressed “end call” on her phone. She was going to pay for the late night chat when she had to get up in five hours, but it was worth it. Chris had a lovely deep voice. They talked about everything. There were no awkward silences. It turned out that they lived less than a mile from each other. They made plans to rendevous in two days, on Thursday, at a Mexican restaurant down the street called Uno Mas.
The next two days seemed to drag. She talked to Chris briefly on Wednesday night. They were both kinda giddy about the planned meeting the next evening. Chris told her to be on the look out for a bald guy with a goatee.
Thursday arrived (finally). Caitlin arrived at Uno Mas fifteen minutes early. She looked around but did not see a bald guy with a goatee. She asked for a booth by the window. She ordered a blueberry margarita and waited.
At about 6:55 Caitlin watched as a beat-up, POS (piece of shit), red Camry entered the parking lot. She hoped that was not Chris. The driver parked, got out of the car, reached back inside for something on the passenger seat. He was wearing white pants, sandals and the ugliest green, yellow and red Hawaiian shirt she had ever seen. He turned around. He had was bald with a brown and gray goatee. Caitlin’s heart sank a little.
Chris entered the restaurant and looked around. Caitlin waved at him. Chris was carried a pink and purple (Caitlin’s two favorite colors) gift bag. Chris bent down to give Caitlin a peck on the cheek. He sat down on the other side of the booth and smiled at her.
Caitlin smiled back at Chris. He reminded her of someone. She could not quite put her finger on it. Who did he look like?
“This is a little something for you,” Chris said, sliding the bag across the table towards Caitlin.
“That is so sweet!” She peered in the bag. Chris had bought her several kinds of scented bubble bath.
“You said you loved bubble baths. I hope you like the scents I picked out.”
Caitlin did like the scents he picked: lavender, rose and honeysuckle. She stood up and leaned over the table to plant a kiss on Chris’s cheek. Chris smiled at her and pulled her face towards him so he could kiss her lips.
They spent the next hour and a half eating and talking. They shared their food and drinks with each other. Caitlin still could not think of who Chris looked like. Chris paid the bill. Caitlin noticed that he tipped the waitress more than 20%.
“I thought we could get some ice cream. Do you like Baskin Robbins?” Chris asked.
“I do! Why don’t you follow me to my place so I can drop off my car. It is on the way.”
Chris followed Caitlin to her apartment. She got in Chris’s POS Camry and they headed to Baskin Robbins. Caitlin ordered a double scoop of chocolate and peanut butter. Chris had a double scoop of mint chocolate chip. They sat outside and licked their cones. Caitlin could not help but notice Chris’s tongue. It sent a shiver down her spine, straight to her pussy.
They finished their cones and drove back to Caitlin’s apartment. She invited Chris inside. They sat on the couch and talked for a bit. Caitlin excused herself and went to he bathroom. She removed her underwear after she flushed the toilet. Her pussy was moist. She fingered herself for a few seconds. This was only the first date. She had not shave her legs so she would not be tempted to have sex with Chris. She washed her hands and returned to the living room.
Chris had turned on the televison. He was watching “Despicable Me”. Caitlin sat down next to him, careful to shift her skirt in such a way that Chris could not tell she had removed her undies.
“I know I am 40 years old, but I love this movie,” he said.
“Me too!” Caitlin snuggled up next to Chris. He put his arm around her. They watched the rest of the movie together.
Chris kissed Caitlin on the head. “It is late. I think I should go.” He got up and turned around to pull Caitlin off the couch. She walked him to the door.
“Bye. I had a great time,” she said. Chris bent down and kissed her again, this time on the lips. He lingered there, but only for a second.
“I had a great time too. I will call you tomorrow.” Chris walked down the stairs to his car. He turned and waved at Caitlin before he got in and drove off.
Caitlin walked back inside, closed the door and locked it. She peeled off her skirt and shirt as she walked to her bedroom. The cuddling and the kissing made her even wetter. She found her vibrator in her bedside table. She pulled the covers down, hopped in bed and slid the vibrator in her leaking cunt. She closed her eyes and imagined Chris kissing her lips, her nipples and her stomach. She slid the vibe in and out slowly, imagining Chris’s tongue inside her mouth. She moaned softly….
The phone rang. And rang again. And again. Caitlin lifted her head to see who was calling. It was him! She answered the phone with one hand. She continued the slow assault on her pussy with her vibe with the other.
“Hey, Caitlin. I could not wait until tomorrow to call. I really wanted to give you a longer, deeper kiss, but I did not want to push it on the first date.”
“I really wanted you to kiss me longer and deeper too, but I was trying to be good. I gotta admit that I did not shave my legs so I would not be tempted to jump your bones on the first date,” she said.
“Like unshaved legs would have stopped me!” Chris chuckled. “So, what are you doing Saturday night?”
“Sadly, I have plans. How about Sunday?”
“Sunday would be great! How about you come to my place around 6:00? I will make dinner,” Chris replied.
“You cook too? Be still my heart! Sunday at 6:00 it is. I will bring dessert!”
Sunday night at 5:30 Caitlin walked into Cupcake to purchase the promised dessert for her date with Chris. She bought four cupcakes, each a different flavor. She pulled out her phone to double check the directions Chris sent her. He really did live right around the corner from her.
Caitlin parked her car, grabbed the cupcakes and her purse and walked to the door of the “castle” belonging to her “Prince”. He opened it before she could knock.
“Caitlin! Welcome to Chez Chris!”
He was wearing an apron that said “Kiss the Cook” so she stood on her tiptoes and planted a kiss on his lips. He smiled down at her and led her inside. They walked back to the kitchen. Chris pulled out a chair for Caitlin. She sat down. Chris bent over and kissed her again. Caitlin was a bit shocked when he slid his tongue inside her mouth. They kissed, their tongues softly touching. Caitlin moaned.
“I am glad I shaved my legs this afternoon,” she said, breaking their kiss.
Chris chuckled and took the cupcakes and Caitlin’s purse, placing them on the counter. Caitlin noticed that there was a salad bowl, silverware, napkins and two half full wine glasses on the table before her.
“I hope you like steak. I also made a salad and baked potatoes.” Chris pulled two potatoes out of the oven. He removed the foil, sliced each of them open, added butter and salt and placed one on each of the plates on the counter. He returned to the table and kissed Caitlin again. “I gotta get the steaks off the grill. Medium rare, right?”
“Right! I am amazed at all the stuff you remember from our conversations,” she said.
Chris smiled and stepped out the back door. Caitlin noticed the very fancy grill he had on his porch. He lifted the lid, grabbed some tongs and placed each steak on a plate. He came back inside and placed a steak on each of their plates on the counter. He took off his apron and grabbed the plates off the counter. He set a plate in front of Caitlin and sat down in the chair next to her.
“Ming the Merciless!” Caitlin exclaimed.
“What?”
“I just figured out who you look like! Ming the Merciless from the cheesy 80’s movie ‘Flash Gordon’. That is who you remind me of!”
“I am not sure if that is a compliment or not,” Chris chuckled.
Caitlin leaned over and kissed him on the lips.
“Okay, compliment,” he said.
Chris and Caitlin ate their steak, baked potato and salad as they talked. Chris would occasionally run his hand up her thigh and under her skirt. Caitlin’s underwear was soaked before the end of the meal. They both cleared the table. Chris took Caitlin’s hand and led her to the couch. They sat down and just looked at each other.
Caitlin leaned over and pulled Chris’s face towards hers. She kissed him, hers fingers gliding over his head. His moustache tickled her nose. Chris pulled her body closer to him, his hands on her ass. He pulled her up a bit so she could move her legs to straddle him. She could feel his cock under her. It was hard.
They kissed passionately. Caitlin moved her hands down Chris’s body. She fumbled briefly with the button and zipper on his pants. Chris tilted his pelvis so Caitlin could slide his pants down to the floor. He kicked them off as he pulled down Caitlin’s underwear. Chris moved his hands along her ass and thighs. Caitlin had freed his cock and was sliding her hand up and down the shaft.
Caitlin moaned into Chris’s mouth. Chris broke their kiss and smiled at her. She smiled at him. Caitlin lifted her arms as Chris pulled off her shirt. He unhooked her bra and let it fall on the floor. He bent his head and kissed her right nipple. It hardened under his lips. He sucked it into his mouth, his fingers pinched her left nipple. Caitlin sighed. She continued to stroke his cock. She moved her dripping mound up and down his leg.
She felt moisture on the tip of Chris’s cock. She pushed his mouth off her breast and slide off the couch. She spread his legs, looked up at him and winked. Chris smiled down at her. She licked the tip of his dick. She licked the underside of the shaft, her eyes still on his face. Chris moved her hair to the side. Caitlin put the tip in her mouth and swirled her tongue around it. Slowly she gobbled up more and more of his shaft. Her head moved up and down. Chris moved his pelvis slowly in time with her mouth. They stared at each other.
Caitlin reached between her legs to spread the lips of her pussy. She rubbed her clit and slid a finger inside her snatch. She continued to lick, nibble and deep throat Chris’s cock.
“Stand up, Princess,” Chris whispered.
Reluctantly, Caitlin pulled her mouth off Chris and stood up. Chris stood and bent down to kiss her. He took her hand and they walked up the stairs. Chris lead her to his bedroom, to the foot of his bed. Caitlin noticed that the bed was unmade and there were at least a dozen pillows of different sizes on it.
Caitlin turned to face Chris, but he laughed. He turned her back around and made her bend over. He lifted her skirt up and spread her legs. Caitlin shivered in anticipation. Chris grabbed his manhood with one hand and spread her cheeks with the other. He slid his cock from her snatch to her ass, slowly. Caitlin moaned.
Suddenly, Chris thrust inside Caitlin’s cunt. Caitlin gasped. Chris held her on his cock and then slowly pulled it back. He was careful never to pull all the way out as he slowly moved inside her. He continued to slowly fuck Caitlin. She moaned under him and moved her hips back and forth. in time with his thrusts.
The pace of their fucking gradually quickened. Chris slammed into Caitlin harder and harder. Caitlin begged him to fuck her, her knees began to shake. Chris pounded her cunt. He slammed her onto his cock faster and faster. Caitlin felt the orgasm building inside her.
“Oh God Chris! I’m cumming,” Caitlin yelled as her pussy clenched Chris’s cock. She screamed as her orgasm took over every fiber of her body. Chris slammed into her and yelled as his own orgasm hit. He ground his cock into her.
Caitlin collapsed on the bed. Chris collapsed on top of her. Their breathing was ragged. Caitlin laughed as her pussy continued to spasm around Chris’s spent member. They laid there for several minutes.
Chris pulled out of Caitlin and rolled off her. Caitlin crawled up the bed and laid on her back, p-lacing her head on one of the pillows. Chris followed her. He stopped over her mound, pulled up her skirt again and spread her legs. He licked her slit, his tongue slid inside her. He lifted his head and crawled the rest of the way up Caitlin’s body. Chris kissed her, slowly. Caitlin tasted his cum mixed with hers. She licked his lips. There was more cum in his goatee. Caitlin sucked it out of his whiskers.
Chris laid down next to Caitlin and grabbed his own pillow for his head. They turned their bodies to look at each other. Chris played with one of Caitlin’s breasts. Caitlin sighed at his touch.
“Cupcake?” Chris asked. Caitlin laughed. She nodded. Chris kissed her forehead before he jumped off the bed. He stopped and pulled his shirt over his head before he walked down the stairs. Caitlin removed her skirt and pulled the sheet up to her chin. She heard Chris’s footsteps coming up the stairs.
“I could not decide which flavor, so I brought the whole box up. Which flavor would Milady like?” Chris hopped back on the bed next to her. Caitlin peered into the box.
“I think the salted caramel,” she said. He handed her the cupcake she picked. Chris chose the red velvet cupcake.
Caitlin licked at the frosting of her cupcake. Chris took all the frosting off his cupcake, looked at Caitlin and then spread the frosting on her left breast, then her right. Caitlin giggled as he licked each breast clean. She bent her head to lick the frosting off his lips and out of his beard.
Chris took the wrapper off the cake part of his cupcake and threw it off the bed. He broke the cake in half and fed part of it to Caitlin’s mouth. He kissed her lightly and shoved the other half inside her pussy. Caitlin yelped. Chris buried his head between her legs and licked the crumbs on her thighs. His tongue lapped at the cake at the entrance of her snatch. He licked and nibbled her and the cake inside her.
When he finished cleaning her pussy he looked up at Caitlin and winked. She dropped her own cupcake on the bedside table and grabbed his head and pulled it up to her mouth. She wanted him inside her again. She needed him inside her again.
“What would you like now, Princess?”

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