First Date

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David learns a lot about life on his first date with Charlen
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TryAnything
TryAnything
9,323 Followers

*Author's Note: This is erotic fantasy. It involves sexual situations between consenting adults, all of whom are over 18 years of age. Since it is fantasy and it's my fantasy, I presume a world free of STDs. I hope you enjoy the story; if not, such is life. Comments are always appreciated.

FIRST DATE

"Hi, Charlene," David said upon meeting her by chance at the local mall.

"Hi, David," Charlene replied, smiling up at the handsome young man, her grey eyes sparkling above a pert nose and a generous mouth. "Shopping or people watching?" she asked.

"I was shopping until I saw you, then I started people watching," David replied, his easy smile creasing his face, his hazel eyes beneath a mop of curly brown hair making her knees weak.

"Aren't you the gallant one," Charlene said, blushing slightly.

David hesitated, thinking of all the times he had imagined being in this situation, desperately wanting to ask Charlene out, but afraid of being rejected. In his mind, she was one of the most beautiful girls he had ever seen in his 25 years. They had grown up together, gone to school together, and now they were back in their hometown after finishing college, hoping to find and start their lives. He liked the fact that she was tall, 5'8". She had a full figure with larger breasts and her blonde hair hung straight down between her shoulder blades.

For her part, Charlene had always thought of David as one of the sexiest guys she had ever met, exuding a languid, relaxed vibe that was contagious, always putting anyone at ease. She liked tall men and David certainly filled that bill, being 6'5". He wasn't particularly muscular, more lanky, matching his personality. She knew that he had always been popular with the girls he went out with, all of them saying the same thing, that he was an incredible gentleman, never pushing them until they made it quite clear that they wanted more attention.

It was the comments about how he was at that point that had interested her the most. To date, she had never yet met a guy who was more interested in how she was feeling or enjoying herself than he was his own pleasure. Oh, there were nice ones, even polite ones, but in the end, when they realized that they were going to get what they really wanted, then it became all about them. But David, according to the stories that she'd hear from time to time, was just the opposite. She had heard from more than one girl that he actually kissed them after having his cock sucked. No guy had ever kissed her after she had sucked his cock. Even more shocking, though, was the story that he would actually eat a girl's pussy after fucking her, even if he had cum in her. The guys she had known wouldn't even touch her pussy after fucking her, especially if they had happened to cum in her, much less eat her pussy after fucking her.

"You know," David said, finally forcing himself to euphemistically jump from the 10m board at the pool like he had had to do when he was trying to be a diver, "I've always wanted to ask you out."

"Is that so?" Charlene replied, looking at him in mock astonishment. "What stopped you?"

"The fear that you'd say no," David replied.

"Are you so afraid of failure?" Charlene asked.

"I never thought of it in those terms," David admitted. "It was more rather enjoying the fantasy in my mind than possibly ruining it with rejection."

"Fantasy!?" Charlene exclaimed. "What kind of fantasy?"

"All kinds," David replied, smiling.

"Are these fantasies the kind that you could tell your mother about?" Charlene asked.

"Most of them," David replied.

"But not all of them?" Charlene asked.

"No, not all of them," David conceded.

"How interesting," Charlene said, smiling.

"Don't girls, or you, ever have fantasies?" David asked.

"Of course," Charlene laughed.

"Could you tell your mother about them?" David asked.

"Some of them," Charlene replied, smiling up at him.

"Maybe we should compare fantasies," David suggested. "Perhaps we have some in common."

"Are you asking me out, David?" Charlene asked.

"Only if you're saying yes," David replied.

"Then it would seem that we're going to go out," Charlene said.

"That...that's great!" David said, his eyes lighting up. "How about tonight?" he asked.

"Maybe for a drink or something," Charlene agreed. "Let's see how that goes first."

"Okay," David agreed. "Where would you like to go?"

"How about Jonesie's, 9:00?" Charlene suggested.

"Jonesie's! That's a pretty rough part of town, isn't it?" David asked.

"I suppose it could be," Charlene replied. "I like to go there because they only play blues music. I've never had any problems and I go there by myself from time to time."

"That sounds good to me, then," David said.

"Well, I need to do my shopping," Charlene said. "It was nice running into you like this."

"I'll say," David replied, grinning like a kid in a candy store. "Uh, see you tonight, then."

"Okay," Charlene said, turning and walking away, not looking back to see David watching her, knowing that he'd be watching, taking extra pains to sashay her ass back and forth.

David was beside himself with excitement as he finished his shopping errand and returned home. Ever since he had been aware of girls, Charlene had captivated him. In his mind, she was the ultimate woman, tall, beautiful, and sexy. He was determined to make a good impression, carefully shaving, twice, and making sure that his fingernails were cleaned and nicely trimmed. He wore clean, snug-fitting Levi's with black Nike tennis shoes and a sky-blue Pierre Cardin polo shirt.

Charlene had also been excited at the prospect of finally finding out for herself if everything that she had heard about David was true. She took special pains to make sure that her legs, underarms, and pussy were all shaved as smooth as a baby's. Thinking about David, she realized that one thing bothered her. He had seemed almost unmanly with his fear of rejection. She didn't like weak men, though she enjoyed having control over men, a bit of a dichotomy of logic, she realized.

After thinking about it, Charlene decided to test David, to see how much of a man he really was. She pulled on a bare wisp of a G-string panty, then her shortest miniskirt, a deep purple in color that barely came down past her ass. She knew that if she bent over at all, her ass and pussy would be exposed. She then pulled on a wife-beater T-shirt that was two sizes too small that left her midriff exposed, as well as generous portions of her breasts from the sides, her small pale nipples pressing hard against the snug-fitting T-shirt and very obvious.

Pulling into the parking lot of Jonesie's at 9:15 in her fire-engine red 1967 Karman Ghia convertible, Charlene smiled when she saw David sitting on a sofa in the back of his powder-blue 1970 Ford Ranchero. As she parked next to his car, David jumped over the side of the pickup bed to open her door for her, his eyes widening when he saw how she was dressed, his mouth dropping open when she swung her legs out of the car to stand up and he could see her G-string clad pussy as her miniskirt hiked up.

"Hello," Charlene said after standing up, not missing the bulge in his jeans as she reached up with one hand and gently pulled his head down to softly kiss him on the lips, letting her tongue trail across them for a moment.

"Hello!" David replied, his eyes bright as he took her in. "You look..."

"What?" Charlene asked, holding her arms out to the sides, her palms facing up.

"Delicious," David replied softly.

"Does that mean that you're going to eat me?" Charlene asked, a big smile on her face.

"I should be so lucky," David replied as she slid an arm around his waist.

"When I wish upon a star," Charlene sang softly.

"And if dreams could make wishes come true," David replied as they walked towards the entrance of the club.

Inside, Jonesie's was very dimly lit and very smoky, as much from cigars and cigarettes as from marijuana. There was a trio playing blues on a raised platform at the back, a piano, a saxophone, and a guitar, while a waif-like black woman wearing a sequined dress that showed the tops of her modest breasts and came down to her upper thighs sang along, her smoky, sultry voice belying her appearance. At least half of the people in the club appeared to be black.

Making their way to the bar, Charlene ordered white wine and David asked for a glass of tonic water with a lime.

"Don't you drink?" Charlene asked, a feeling of dismay in her stomach.

"No," David replied. "Alcohol doesn't agree with me."

"Does it bother you that other people drink?" Charlene asked as their drinks were delivered.

"Not in the least," David replied. "I only abstain because I've learned to listen to my body. It doesn't like alcohol."

"What happens when you drink alcohol?" Charlene asked.

"Well, the first thing is a headache," David replied.

"Oh, I hate headaches," Charlene declared.

"There's nothing I dislike more," David agreed.

"What else?" Charlene asked.

"Now it gets a bit more embarrassing," David replied.

"Really!?" Charlene replied. "Now I definitely want to know," she said with a laugh.

"It's a...sexual thing," David replied, feeling a bit defensive.

"Oh, please, details," Charlene laughed. "One of my weaknesses is horny talk."

"Well, I find it difficult to get an erection," David replied, blushing. "And if I do get one, it's hard to make it last very long."

"Then you definitely shouldn't drink," Charlene said, "at least not with me. You don't have those problems when you don't drink?" she asked.

"I never have," David replied.

"What do you think of this place?" Charlene asked.

"I like it," David replied. "It's very different. I didn't realize that there were clubs that were so well...balanced with respect to the patrons."

"Blues comes from the blacks," Charlene said. "From the days of slavery. Same with jazz. I feel the blues and jazz in a visceral way. It's hard to explain."

"It definitely touches you differently than regular music," David said.

"Shall we try to find a table?" Charlene asked. "These stools are a bit awkward."

"Uh, sure," David replied, glancing down and seeing that Charlene's panty-covered pussy was visible, due to the way her miniskirt pulled up in order for her to be able to perch on the bar stool.

Smiling when Charlene slipped her hand into his, their fingers intertwining, David led her through the crowd of people, finally spotting a table in the corner behind a pillar which blocked their view of the musicians, which helped explain why it wasn't occupied. The padded bench running the length of the wall was the only seating, so they sat next to each other, Charlene snuggling up against David, one hand resting on his upper thigh, smiling when he slid an arm across her shoulders and held her against him, one breast pressing into his side.

"This is nice," Charlene said, giving his thigh a gentle squeeze.

"It is," David agreed.

"Do you dance?" Charlene asked.

"A bit," David replied, "but I'm definitely not going to win any talent shows."

"This kind of music, the dancing is more of an excuse to hold each other and move to the music," Charlene said. "I'm not looking for Fred Astaire."

"That sounds good to me," David said.

"Are you asking me to dance?" Charlene asked, trying to hide her exasperation at his lack of initiative.

"Yes," David replied, oblivious.

Charlene led the way towards the small dance floor in front of the musicians, melting into David's body, one arm around his waist, the other up around his neck, while his arms were around her body, his hands on her back. David was very aware of Charlene's full breasts pressing into him as she slowly and sensuously gyrated against him to the music, the hand behind his neck gently stroking him as she'd grind her crotch against his thigh.

David knew that there was no possible way that Charlene didn't realize that his cock was rock-hard in his Levi's when she pressed her body against him, pulling his head down to softly kiss him, her other arm pulling him close as the kiss deepened, her tongue pressing between his lips to find his as they gyrated against each other, sucking tongues and sharing breath until Charlene released him to come up for some air.

"Mmm, you're a good kisser," she said, both hands around him now, holding him close as she pressed herself against him, his hands remaining in the middle of her back.

"So are you," David replied, smiling.

"Shall we do it again?" Charlene asked, now really struggling to hide her disappointment in his total lack of initiative.

"Yeah, I'd like that," David said, bending down and kissing her.

While David's hands stayed firmly on Charlene's lower back, one of hers drifted down to his ass, holding him close, feeling his hard cock pressing against her belly as they continued to move to the music.

"I think I could use some more wine," Charlene said when the song ended, leading the way back to their table, sighing as she realized that she was wasting her time. If she had to tell him what to do about everything...

"Would you mind if I danced with your lady?" a well-dressed black man asked when he approached their table, a friendly smile on his face.

"I'd love to," Charlene said, pleased to finally meet someone who was willing to take the initiative.

David was a bit nonplussed at the abruptness with which Charlene left to go dance, but shrugged and decided that she must really enjoy dancing. As he watched them dancing, he saw Charlene pull the man's head down for a kiss, just as she had done with him, a long deep kiss. He also noticed that the guy had one hand on Charlene's ass, holding her close, and that she didn't seem to mind. What shocked him, though, was when the guy slipped his hand beneath Charlene's miniskirt to directly hold her ass, Charlene breaking the kiss and staring at him with astonishment, then pulling his head back down and feverishly kissing him. When the song ended, Charlene returned to the table with the guy in tow.

"Oh, David, Jimmy's a really good dancer," Charlene enthused, sitting between them, a hand on each of their thighs.

"So I noticed," David said, a bit disgruntled. He finally had a date with her and she was dancing with a stranger and making out with him on the dancefloor.

"I just love to dance," Charlene said, flagging down a server and asking for another glass of wine.

"You're a great dancer," Jimmy said.

"You make it so easy," Charlene replied.

"You're lucky to have such a hot woman," Jimmy said, leaning forward so that he could look at David.

"Uh, I sure am," David replied, much to Charlene's disappointment.

"Would you like to dance again?" Jimmy asked as Charlene's wine appeared.

"Well, sure," Charlene replied, gulping down half of the glass. "You don't mind, do you?" she asked David, leaning down to kiss him lightly after she stood up, wishing he would say that he wanted to dance with her.

"No, make yourself happy," David replied. "I enjoy watching you."

"You do!?" Charlene asked, her eyes opening in surprise, then gasping when she felt Jimmy's hand on her ass beneath her skirt.

"You're pretty hot," David said.

"That's one of my fantasies," Charlene whispered, quickly kissing him, then standing up and taking Jimmy's hand and going to the dancefloor.

This time Jimmy wasted no time, both of his hands disappearing beneath Charlene's miniskirt, her arms around his neck as they kissed, barely moving, just grinding against each other in time to the music. When they broke their kiss, David saw Charlene talking to Jimmy, his hands still beneath her miniskirt playing with her ass. He wondered what she was saying when she saw Jimmy turn his head to look at him, only to have Charlene place a finger on his chin and turn his head back to her, still taking. He saw Jimmy shrug and Charlene's face light up, then they left the dancefloor, Jimmy going through the door to the toilets as Charlene returned to the table, snuggling up against him, her hand high on his thigh.

"David, will you share a fantasy with me?" Charlene asked.

"What do you mean?" David asked.

"Well, you've got fantasies, about me, too, you said," Charlene replied. "And I've got fantasies. Maybe we can share our fantasies together at the same time."

"Really?" David asked, his face lighting up. "But you don't know what my fantasies are," he reminded her.

"And you don't know what mine are," Charlene responded. "Shall we both take a chance and agree to live each other's fantasies without even knowing what they are?"

"You mean, not just tell each other, actually do it?" David asked, astonished beyond belief at his good fortune, not yet having figured out how to see if Charlene was interested in some more intimate fun.

"We might as well," Charlene replied, "unless you'd rather not."

"No," David said. "Not at all. I think that would be fun. Are you sure?"

"You're not going to hurt me, are you?" Charlene asked, wide-eyed innocence writ large on her face as she leaned close, flicking her tongue out across his lips.

"Never," David replied firmly.

"And I promise the same," Charlene said. "In fact, I promise not to do anything that you don't do. How's that?"

"That...that's fantastic!" David replied, stunned.

"There you are," Charlene said when Jimmy appeared. "We're going to go down to the lake. Would you like to join us?"

"Sure," Jimmy replied, David feeling the bottom of his stomach dropping out.

"Ready?" Charlene asked as she turned to smile at David.

"Uh, yeah, sure," David replied, getting to his feet.

"You can ride with me, Jimmy," Charlene said.

The only consolation David had as he followed Charlene's Karmen Ghia to the lake was that Jimmy stayed on his side of the car. He just couldn't understand why she had invited him. There was no moon and the Milky Way was blazing overhead as they parked next to each other right at the lake's water's edge, no other cars in sight.

"This is a perfect night," Charlene said as she exited her car with Jimmy.

"Nice wheels," Jimmy said, admiring David's Ranchero.

"We can sit on the sofa," Charlene said.

"Sure," David agreed, lowering the tailgate and giving Charlene a hand so that she could step up, her miniskirt rising high enough to totally expose her G-string covered pussy.

"I explained to Jimmy that you and I were going to live out our respective fantasies together," Charlene explained as they sat down with her in the middle, a hand on each of their thighs. "He's agreed to help."

"Help?" David asked.

"Part of my fantasy is that there are two guys," Charlene explained, letting her hand slide from his thigh onto his rock-hard cock. "You did say that you liked watching me."

"I-I didn't...I didn't mean..." David stammered.

"You liked watching us on the dancefloor, didn't you?" Charlene asked, firmly gripping his cock through his Levi's.

"Yes," David admitted, turning to look at her, his eyes widening when he saw that she also had a hand on Jimmy's cock through his pants.

"Do you still want to share our fantasies?" Charlene asked.

"Okay," David replied, swallowing, his mouth suddenly dry.

"Do you want me to start?" Charlene asked, sighing inwardly, ruing the fact that David was so insubstantial, but also smiling as she pictured things evolving.

"Sure," David replied, the feeling of her hand squeezing his cock almost unbearable and not sure how he would go about starting anything, not with Jimmy right there.

"And you give me your word that you'll go along?" Charlene asked.

"Yes," David replied, wondering how far she was going to take things.

"My fantasy revolves around having two men at the same time, each one having me while the other watches," Charlene said, squeezing both of their cocks.

TryAnything
TryAnything
9,323 Followers
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