Game Night

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Best friends become lovers.
2.2k words
4.15
169.3k
25

Part 1 of the 2 part series

Updated 09/29/2022
Created 09/15/2006
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David rolled the dice and snake-eyes came up. He moved his race car token to St. James Place and put $180 into the bank for the deed. He and his best friend, Samantha, hadn't had a game night with just the two of them in over a year. In high school, it had been a weekly tradition, either on Friday or Saturday night. Ever since college started, though they saw each other quite often, they'd been too busy for game night, either with school, work, or dates. Now, here they were, having their first game night in her new apartment, which her parents paid for because of her excellent grades and for being on the Dean's list.

David reached for the dice. "Doubles," he said with a smile.

Sam rolled her eyes. "Oh, just roll again."

This time David turned up double twos. He put his car on Free Parking. Since they were Monopoly purists, he gained no money for the spot from any specialty rules. They grudgingly put up with other people insisting on putting money in the middle of the board for Free Parking stops, but when they played, it didn't happen.

"Roll again," Sam said. "And remember, one more double and you go to jail."

David chuckled. "Like Chet." Chet was Sam's current boyfriend, and David didn't think much of him. Not that he was a hoodlum or anything, but he'd told a few stories of how he and his buddies had been trouble makers in high school, so David liked to tease Sam about Chet being a bad-boy. He actually was a pretty nice guy, and he treated Sam very well. There was just something about him that David didn't like. He couldn't put his finger on it, but it lingered. He felt that about all the guys Sam had dated.

She smacked him on the shoulder. "Shut up. Chet's not a criminal. He's a nice guy." She paused and smiled. "At least he has a personality."

David groaned. "Cheap shot." Sam had always called his last girlfriend, Brenda, boring. Though he hadn't admitted it to anyone, including Sam, he'd thought so, too. He had continued to date her because, though she hadn't let him have sex with her, he did get free reign of her breasts when they made out. She'd dumped him about a month ago, presumably for another guy, though he never did get the full story. He'd yet to jump back on the dating horse.

"Oh, just go," Sam said.

David rolled for this third time on this turn, and though he didn't get doubles, he did roll a ten--a six and a four. "Crap," he said. A ten meant he had landed on the Go to Jail square. That was sometimes a good move late in the game when there were too many unfriendly pieces of property out there, but this early he wanted to buy as many as he could. He picked up his token and moved it directly to jail.

"You're not going to give me the satisfaction of watching you move to jail square by square?" Sam said in a mock pout.

"No satisfaction for you," he said, sticking his tongue out at her.

Samantha giggled and picked up the dice. Her dog marker sat on Vermont Avenue. "Maybe I'll get snake eyes and come visit you."

David smirked. "I wouldn't say no to a conjugal visit."

Sam blushed and rolled the dice. David wondered what that was about. They'd been friends since Kindergarten, and they often made sexual jokes. She usually gave as good as he got, and he'd never seen her blush when they were alone.

Her roll was a nine, and she landed on Community Chest. She drew the card and won second place in a beauty contest. "Here you are, going to jail, while I'm winning second place in beauty pageants." She gave a big mock sigh. "Where did we go wrong?"

"Sounds like your future life with Chet," he said with a smile.

"Shut up," she said. He could tell she wanted to continue the thought, that there was something she wasn't telling him, but she wasn't ready. He knew her well enough that if he just waited, he'd learn what it was.

"Well," he said after she collected her ten dollar prize, "since you won the beauty contest, you should do your little runway twirl."

"But I only won second place." She stood up and giggled while she said it, though.

God, she was beautiful. He'd thought so since they were nine years old. By the time they'd been of dating age, he hadn't had the self-confidence to change their relationship. She stood before him now with a shy smile she never wore around him. Before he worried about that, though, he drank her in. She stood 5'3" and couldn't weigh more than 110 pounds. He guessed her breasts were B-cups, since that's what Brenda had been, and Sam's were about the same size. Her wavy brown hair, usually done up in a pony tail, hung loose and down past her shoulders. Tonight she had on a tight blue sweater (his favorite color) and a long, pale-blue skirt, which was a bit unusual. He couldn't remember when she hadn't dressed in jeans or jeans-shorts and a loose, comfortable t-shirt when it was just the two of them. He wasn't going to complain, though. He loved when women wore long, flowing skirts. Had he ever told her that? If he didn't know better, he'd think she was dressed to seduce him. He hoped it didn't mean Chet was coming over later.

"So," she said, "did I deserve the second place finish?"

He shook his head. "The judges were nuts. You should have taken home that $20 prize for first place." They laughed, and then he added, "I hope Chet realizes how lucky he is."

"I broke up with him earlier today," she blurted out, and then her face flashed bright red.

"What? Why? I didn't like him, but I thought you did."

She chuckled. "You don't like any of my boyfriends. It's just . . . I'm in love with someone else."

"Don't tell me. You and some girlfriends went out after work one night to a male strip club and you fell for Renaldo. I can read it in your face." David grinned, but it quickly disappeared when she didn't laugh at the joke. "What is it, Sam? Do I know the guy?"

Tears came to her eyes. He saw right away, though, that they weren't bad tears, so he relaxed as much as the current situation allowed. That was another thing he loved about her; her emotions could be so close to the surface.

"God, David, you're so dense," she said. "You always have been." She wiped a few tears away, walked over to him, and sat on his lap. He opened his mouth to say something and was greeted with a kiss. It started slow and tentatively, but before long bloomed into a full-blown make-out session. Finally, she lifted her mouth from his and they just sat there, holding each other.

"Wow, I can honestly say I wasn't expecting that," David said.

She fluttered a few kisses onto his neck. "That's because you're a man and didn't pay attention to any of the little things and signs I was flashing your way all night."

"Well, where did it come from?" he asked.

"I've been waiting to do that for ten years," she said. "You just weren't ready for it. I didn't think you were emotionally stable enough for it until now. Call me greedy, but I want a best friend and a lover."

He smiled at her. She was right. He hoped he could prove ready now, but wasn't worried. He loved her with all his heart. "This is seriously happening? You really broke up with Chet?"

"You didn't like him anyway," she said as she lifted her hand to stroke his cheek. "I always found it cute that you were so jealous of all my boyfriends. But it paid off. I'm finally yours, now and forever."

He kissed her on the forehead and then the lips. "Okay, one more question." His head was spinning, but this popped into his head, and it proved to him that they were still best friends, not just a couple. "Are we going to finish our Monopoly game or what? Because when I get out of jail, you're in serious trouble."

She laughed and leaped off his lap. "Well, let's see. It's Tuesday night. Neither of us has to work until Saturday. Would your academic future go down the tubes if you blew off the rest of the week of classes?"

He smiled and shook his head. "But would a student on the Dean's list really ditch class?" he teased.

"That's the best part," she said with a sly grin. "My teachers will believe me without a doubt if I say I got sick. Anyway, why don't we leave the board set up. By Thursday, I'm sure we'll need a break from the bedroom." She flashed him a wicked grin and dragged him towards her bedroom door.

David felt a lump grow in his throat. She was so confident, and he didn't want to disappoint her. "Um, Samantha, I have to admit, I'm still a virgin."

They'd reached the door, and she pushed him up against the frame and gave him a big kiss. "Boring Brenda wouldn't put out, eh?" she said when she broke the kiss.

He shook his head. "But, to be fair, I never really pressed her." Which was true. He'd enjoyed sucking and playing with her breasts too much to upset the situation. "Hell, she could have been a roaring slut for all I know, just not around me."

She laughed and kissed him again. "It's okay, David. I am, too."

He gave her a mock look of surprise. "A virgin or a roaring slut?" he said and was rewarded with a smack to his shoulder.

"I was saving myself for you," she said. "Pissed off all my boyfriends, Chet included."

"Good," he said. "They were all jerks."

She kissed him again. "No they weren't. You were just jealous." She then untangled herself from his arms and backed into her room. "Now, since we didn't get to finish Monopoly tonight, why don't we play a new game? Guess what color my underwear is." She whipped off her tight sweater and stood before him in a slinky white bra. "And I'll give you a hint. It's not the same color as my bra." She cupped her breasts through her bra, and he almost exploded in his pants.

He said a few colors, but each guess was met with a shake of her head. Finally, he said, "You stumped me."

She flashed him another wicked grin. "Actually, it was a trick question." She lifted up her skirt and he was greeted by the sight of her bare pussy. Though, like most red-blooded teens, he'd seen plenty of pornography, he'd never actually seen a fully naked lady in person. Samantha's pussy looked ten times better than any porno actress. She'd shaved it almost completely smooth, except for a little tuft of hair above her beautiful lips, which themselves looked to be soaking wet. He knew enough to know that was a great sign.

"God, you're beautiful," he managed to croak out as he stepped towards her. He embraced her and they fell onto the bed. As they kissed with all the ferocity that they'd been storing up for years, her hands worked on getting his pants off, while he tried to unhook her bra. She succeeded quickly, and his seven inch cock sprang into view, while he began to wonder if there was a padlock on the back of her bra. Finally, she pushed his hands away, rolled him to his back, and sat on top of him. Before he fully comprehended the situation, his dick slid inside of her. He wished he could see it, but her skirt lay in the way. They both groaned and she popped her bra off. The sight of her two perfectly perky breasts almost caused him to lose control again, but he managed to catch himself.

Between bounces and moans, Samantha managed to say, "Don't pull away, baby. I'm on the pill for you."

That did it. He wanted their first time to be perfect, to last more than thirty seconds, but her vaginal walls were too tight, too hot, too wet, and this situation was just too surreal. He exploded deep inside of her, and she continued to ride him, milking every last drop from his cock. Seconds later, her already ragged breathing stopped, then she squealed, convulsed, and collapsed on top of him.

They laid in each others arms for a few minutes, just regaining their breath. David couldn't get his head around these turn of events. Not that he minded, of course. After all, what could be finer than finally realizing your love for your best friend? When Samantha looked up at him with a contented smile, he could tell she felt the same way.

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4 Comments
AnonymousAnonymousalmost 14 years ago
Wow.

That was so perfect. I'd have loved for that to have been my first time. Beautifully written. Great job.

AnonymousAnonymousalmost 16 years ago
Like the first time... great, but over too soon

This story was expertly crafted, but it didn't last long enough. It could've used more tension.

AnonymousAnonymousover 17 years ago
I want a sequel!

I definitely thought this story had good potential, and I thought maybe they would use the Monopoly game in some sort of dirty fashion. Please write a sequel!!!

AnonymousAnonymousover 17 years ago
Abrupt

There was a fair bit of development, and then they screwed and it was all over.

I think you could have expanded that last scene a bit.

Otherwise, well-written.

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