Third Date

Cyndi checked her light makeup in the mirror for the fourth time. She went to the living room and adjusted a chair for the third time. She moved some magazines that were a little untidy for the second time. Outside, the last of the summer light dipped below the horizon.

Tonight was her third date with Sam, and she intended to take full advantage of the "sex on the third date" tradition. She didn't think Sam would be a long-term thing, but she intended to enjoy him for a bit. On their first date, she had let him give her a kiss as they said goodbye on her doorstep. On their second, she let him kiss a bit longer and stopped when she felt his hands wandering. She didn't want him to think she was easy.

But tonight, she planned to go all the way. And she fully intended to have Sam frothing at the mouth before he finally pushed his cock between her legs.

She tidied up a bit more until the buzzer rang.

"Hello?" she said into the intercom.

"Hey, Cyndi, it's Sam."

"Oh, Sam, I lost track of time. I'm running a bit behind, but come on up." She stopped by the hallway mirror and paused. Brown hair wet with bangs arranged to swoop over her forehead and down to her jawline? Check. Towel pushing her 35B breasts together to make them look bigger? Check. A touch of lipstick and blush? Check.

She opened the door when she heard the knock. Sam was tall, had dark, curly hair, glasses, and a wry smile. He paused and looked at her. She was wearing nothing more than a towel, which she had arranged so that it barely came past her pussy.

"Sorry, Sam. I got super busy today at the office. I hope you don't mind?" Clearly he didn't. Who would? He shook his head, leaned forward, and kissed her on the cheek.

"Not a problem. We've got plenty of time before dinner."

"Oh good. Just have a seat here and I'll go get dressed." She sat him down in an armchair whose angle she had checked three times. She walked to her bedroom, with her arms up to hold up the towel, but also to give it a little tug up so that Sam, watching her walk away, would see just the beginning of her ass. She flung open the door to her room, walked in quickly, and then swung the door shut without looking back, the very model of a harried date.

The umbrella she had placed just so did its trick, the door swung into it, hit it, and popped open a tiny bit. The crack lined up perfectly with the angle of the armchair so that someone leaning to his right could see through it.

She had already moved into her closet, making it obvious that she didn't seem to have noticed the door situation. She dropped the towel and pulled two skirts off her hangers and brought them to her bed. As she stood, naked and pretending to contemplate the skirts, she stood right in line with the crack of the door. She paused there for about 15 seconds, grabbed one of the skirts and swung around, careful to turn away from the door so she would continue to not notice the open door.

When she walked by the door again a few minutes later, she had on a tight white scoop neck t-shirt and nothing else. She went to her dresser, pulled out a pair of sexy panties, and grabbed the skirt from the foot of the bed. Didn't want to spoil the fun for Sam by showing him the underwear too soon.

She walked to the door and opened it, seemingly unaware that it hadn't closed all the way. Sam had grabbed a magazine and seemed to be reading it, but the bulge in his pants suggested he had seen some of the show.

"How do I look?"

He looked up and smiled. "You look pretty." Her t-shirt came just to the waistband of her knee-length flowery skirt, showing the occasional flashes of skin as she moved.

"Oh, you're so sweet. Let's go to dinner."

During dinner, the two caught up on each other's weeks and got to know each other a bit better. Cyndi crossed her arms under her breasts a fair amount, pushing them up and out, especially when she leaned forward to ask him something in the noisy restaurant. She let herself get a bit tipsy. Hopefully Sam would try something.

She invited him up to her apartment for some post-dinner Scotch, and before long the two were making out on her couch. His hand stroked her back and slid down it to her ass. She lifted up a little bit to let him know it was okay, but as his hands moved to the front, she stopped him by pushing his hand down and pulling back.

"Do you want to play a game?"

He arched an eyebrow. "What kind of game?"

"An easy one. I ask you a question and if you guess the answer, you get a prize."

"What kind of prize?"

"Well, play the game to find out!"

"Okay," he said. He leaned back a bit. "Go ahead."

She stood up and faced him. "Tonight I did something unusual for me. What was it?"

He moved his mouth a bit. "Uhh. Ordered steak?"

"Ha. No. I love steak. Next guess."

"Wore a skirt?"

"Nope. Do you want a hint?"

"Please."

"Okay, but you don't get a hint for free. You have to give up your shirt for it."

He smiled. This was going the right direction. "Seems fair," he said and unbuttoned his shirt to reveal a smooth, muscular chest. She couldn't wait to caress it, but first the game.

She turned around and looked back over her shoulder at him. "Here's your hint. Unhook my bra."

He stood up quickly and put his hands on her back to no avail. "Hmm. Can't find the clasp? Maybe it's in front. She leaned back and he moved his hands over her ribs and over her breasts.

"Nothing there, either," he said, breating huskily into her ear.

"You sure? Feel around a bit more."

He cupped her breasts and squeezed them. He slid his hands over them and rubbed her nipples until they poked firmly against the smooth fabric of her shirt.

"Hmm. I think you went out without a bra on."

"Really? I always wear a bra. That would be unusual." She pulled forward and turned around. "Only one way to test the theory," she said. She crossed her arms, put her hands on the edge of her shirt, and lifted it up. The tight shirt caught on her tits, and when she lifted it past them, she could feel them bounce as they emerged into the cool air.

"Good guess! You should really make sure I'm not wearing a bra, though." He stepped forward and ran his hands along her naked breasts, cupping them and squeezing them. He bent down and sucked first her right nipple into his mouth and then her left one. She moaned and ran her hands up and down his chest.

"Do you want to know your prize?" He pulled back from her, leaving his hands on her chest.

"These are a prize, baby."

"Those are just side effects. Your prize for guessing that I didn't wear a bra tonight is that when we fuck later, you'll get to choose the position. Any position you want."

He smiled at her. "I like this game, but it's going to be hard to choose."

"Well, maybe we can manage a couple."

The two kissed some more, standing in her living room. He worked over her tits, and she leaned into him. Her nipples were rock-hard. When he moved his hand down her back and onto her ass, she pulled out of the kiss.

"Ready for the next question?"

"Sure, baby."

"Okay, sit down again." He stepped back and sat on the couch, leaning forward.

She looked down at him and said, "Describe my panties."

"I think I'm going to need a hint," he said.

"You have to try."

"Black lace hot pants," he said.

"Hmm, no. But maybe next time. Guess again."

"White g-string."

"I'm getting all sorts of ideas for our next couple of dates," she said. "But no, that wasn't it, either. Ready for your hint?"

"Yes, definitely!"

"Okay, but this is a big hint so you're going to have to pay up. You need to pay with your slacks, your shoes, and your socks."

He quickly disrobed, leaving him in nothing but blue striped boxer shorts with a huge bulge in them. He sat down again.

"I'm going to flash you my panties, but I'm going to do it for a very short period of time. So you'll have to pay attention. Ready?"

He nodded and licked his lips. He leaned forward to get a good look. She lifted her skirt until she could grab the hemline, and then lifted that until it was just covering her panties from his angle.

"You ready for the flash?"

"Yep."

She bunched up her hemline and pulled it high up to her breasts. And then stopped. A quick flash. Ha. She was holding up her skirt until he described them.

"Very nice. Red panties with lace on the legs decorated with little white hearts and one big pink heart over your pussy."

She dropped the skirt and said, "God. You totally nailed it. I guess there's no reason to keep them secret anymore." And with that, she reached around behind her and undid the skirt, pushing it down and wiggling a little until it slid down to her feet. She stepped out of the heap and crooked her finger to tell him to come over to her.

He moved his hands freely over her body as he kissed her, and she let him. Then he pulled out of the kiss.

"And my prize for this question?" he asked. It sent a little shiver of happiness along her spine.

"Well, that was a pretty amazing display of powers of observation," she said, "so I think it gets a big prize." She knelt down in front of him and pulled at his boxers. "And I think I get a big prize too," she said, just as she pushed her mouth onto his hard cock.

He moaned as she worked him over, circling his tip with her tongue and sliding her mouth up and down his shaft.

She stopped and looked up at him. "One last question," she said.

"Okay," he said with a grunt. His cock was sticking straight out, and it was bright red from all the blood flowing into it.

"Did you watch me through the crack I left for you in the door earlier?"

He looked down and blinked. His eyes shifted left and right. Then he sighed.

"I did."

"I'm so glad to hear you fess up to it," she said. "Since you got that answer right, here's your prize: swallow only or facial and then swallow?"

He groaned again and leaned his head back. "Swallow it all honey. Let me pump cum right down your throat."

She began to work over his dick a bit more until she heard him say, "What if I had said no?" She pulled back off his cock and let the head go with a pop.

"I would have called you a gentlemen and given you the same choice."

She went back to his eight-inch dick and licked it up and down. She caressed his balls gently and then moved her mouth down quickly to cup first one and then the other nut in it. He was moaning and quivering as he stood.

"I'm going to cum," he said, panting heavily. She looked up at him, smiled, and then engulfed the head of his cock in her mouth. One more up-and-down pump of her head, and he was shooting his load, just as he had wished, into her mouth. She swallowed the first squirt and then held the rest in her mouth. Three squirts later, she leaned back, tilted her head back and opened her mouth for him to see. He looked down, moaned again, and she closed her mouth to swallow the creamy, sticky mass she had shown him.

"Oh, baby, that was hot," he said. He was shaking as her tongue cleaned him up. "I hope I have another one in me."

"The night is young," she said. She stood up, turned around, hooked her thumbs into her panties, and pulled them down. She bent at the waist to show off her round ass and her wet pussy. She stayed there, bent over, for just a moment as he put both hands on her cheeks.

"Oh, yeah," he said. "You have such a hot ass." She stood up and turned around again.

"Doggystyle," he said. And they went to her room.