Sex Bet Between Friends, part 2

The month-long bet between two buddies began heating up in the third week. Rick and Charlie were best friends since grade school. Always competing, as adults their most recent challenge morphed into something quite raw and chauvinistic…Over 30 days, who could have sex with a woman in more locations

After the second week, Charlie was ahead four to two. A single, GQ looking bodybuilder he did tend to win most of their physical competitions. Rick was also good looking and very bright. This bet made their individual competitive natures shine.

Luckily for Rick, a man with a steady girlfriend, the tables were about to turn. Without knowing about the existence of the bet, Sarah was back up for sexual adventures. Her menstrual cycle had ended and she was feeling extremely horny. After work one evening, Rick invited her up to his office after work. His co-workers thought he had too much work to leave early. When in actuality he was plotting a special encounter with Sarah. She showed up thinking they were going to grab a quick bite to eat on their way home. When she got off the elevator to his office he greeted her naked with a flower tucked between his already erect cock and his right ball! To his delight, Sarah was happily surprised and ready for action. They began by having sex on the lunch room table and then again on Rick’s bosses desk. That was twice in just an hour!

They considered a third go at it in the ladies room but just as they got finished on the desk, the janitorial service showed up to clean the office. They did wonder if the three-man cleaning crew were at all aware of what they’d been doing. But, Rick and Sarah didn’t wait to find out. Giggling and only partly dressed they scurried down the elevator and onto the street.

Then, on Thursday evening, Sarah called Rick and asked him to come help her carry some boxes home from work. Little did he know the plans she had made. When he arrived the last of Sarah’s work friends were leaving. They were invited to join them for drinks. Sarah quickly declined the invitation. Before the elevator door shut, she jumped his bones. Three times in one week. Sure he was going to win with these 3 additional sex locations, he could almost taste his steak dinner winnings. But, he wouldn’t know for sure until coffee on Sunday.

Rick always marveled at the way the feminine gender reacted to Charlie. It didn’t matter if they were young or as old as his grandmother… He was a ladies magnet. Girls would practically fall over each other to get into bed with him. Actually, after some thought, Rick realized he might have been crazy to have accepted this particular challenge…

A Sex Bet

Rick arrived early for coffee that Sunday morning. Charlie walked in looking a bit haggard. Initially, Rick was worried it meant that Charlie had been working to win the bet every night that week. But that wasn’t the case at all. Charlie was sick. He quietly explained he had spent one night with two roommates having a sex party in their apartment. Rick argued that having sex with them both in the same place did not fit the parameters of the bet. Watching his coffee get cold, Charlie couldn’t argue and accepted defeat that week. At the end of the third week, Rick was ahead 5 to Charlie’s 4. Wanting to win, neither liked the taste of defeat. They had one week to go and ego was the name of this game.

The last week of Rick and Charlie’s sex bet turned out to be strange as well as telling with regards to their relationship. In their minds, this bet directly challenged their sexual prowess…something very important to them both.  The prize of the steak dinner and bottle of Glenfiddich, 18-year-old Malt Scotch Whiskey became secondary.

On Tuesday evening, Sarah along with her two sisters held a 30^th birthday party for a High School classmate. The party took place at their favorite local bar and would include a male stripper. Little did Sarah know that Charlie was the hired stripper! At first, she felt awkward. After all, she had grown up with him and he was Rick’s best friend. Seeing him strip could be strange… But after giving it more thought, she secretly wondered what Charlie looked like naked…

It seemed that everyone had a secret about Charlie because Sarah’s sisters were elated to hear he was their stripper. Each had a tremendous crush on him. And, since both of them were single, they decided to make their own wager: Who would bed him at the end of the night. This was just too much information for Sarah. So much so that she called Rick from the party and told him what was happening and how uncomfortable this was making her.

Finally, after hearing about the strange set of circumstances surrounding Charlie, Rick decided to tell Sarah about the bet. When she first heard about it, she got angry and felt a bit used. But after chatting further with Rick she realized that Charlie might actually win the bet by bedding her very sisters!

All of a sudden Sarah’s competitive nature kicked in. She came up with a brilliant idea that would help Rick win the bet even if both of her sisters had sex with Charlie. She wanted to make sure he didn’t win. Not just for Rick, but also because she didn’t want her sisters to be unknown pawns in this ridiculous competition.

The party and Charlie’s striptease were very entertaining from that point forward. Not only did Sarah enjoy watching Charlie take off his clothes, but he was actually quite good at it! After his performance, she secretly took her sisters aside and told them about the bet between the boys. Both listened carefully and decided that they had grown to like Rick so well, they wanted him to win the bet. Deciding to still go for their own bedding challenge with Charlie, both sisters vowed to only have sex with him in his bed. That way he wouldn’t get any points towards winning the bet. A hip and very clever solution that gave everyone a win… except Charlie.  All he knew was that he had Sarah’s sisters fighting to go to bed with him. He thought he was sure to win by bedding them both. Little did he know there were more people in on his bet than he realized.

That evening Sarah’s attention shifted gears. Now she wanted to know where and how often she and Rick were going to have sex. Rushing back home to him they plotted how they were going to win that steak dinner and share the Glen Fiddich, Malt Whiskey with her sisters.

Public Sex for Rick & Sarah

Wednesday morning they woke up with a plan to meet for that day’s sexual encounter. Excited and determined, they couldn’t wait to meet for lunch at the local market. While there, they did it in the public bathroom! It wasn’t the cleanest choice but had the added excitement of someone knocking on the door before they were finished. That same night after work, they took a stroll through the town square and decided to crawl under the bandstand where they used to make out years earlier. With three days left in the competition, Rick’s score had increased by two. They both wondered how Charlie was doing…with or without Sarah’s sister’s involvement…

Mornings that week, Rick was responsible for feeding his neighbor’s cat…sex in that apartment was a no brainer.

Thursday night Sarah checked in with one of her sisters… Giggling while telling her, Charlie had desperately tried to get her to have car sex. But she insisted on going to his place instead. It was obvious to her that he was disappointed as to the location of their encounter.

By Friday morning, Rick’s score had increased by three, totaling 8 locations. He and Sarah knew that Charlie’s time had been spent with no additional locations. That morning the second sister called to say that Charlie had tried to entice her to meet in the park during lunch. She told him she was the traditional type and would only have their “special encounter” in his bed… Without a date set, he got off the phone sounding disinterested and preoccupied. Unless Charlie went to an orgy in a mansion with a woman who would do it in every room, he was going to lose this bet.

Sarah and Rick decided to add three more locations before the final Sunday morning tally. In the back seat of Sarah’s workmate’s car, in the pool at the apartment complex and at the back of their empty gym just before closing. Adding insult to injury, Sarah had Rick take photos at each location for proof. Rick’s final total was eleven.

Puffed up with stories and pictures ready, Rick was sitting with his coffee before Charlie even walked in the door that last Sunday morning. When he did arrive, Charlie suspected that Rick was the winner. He took the loss better than Rick would have expected. Surprisingly, actually felt empathy for his longtime friend, he decided not to show the pictures.

After having their first cup of coffee, both men decided this was the last ridiculous bet they would engage in… It was time to grow up. And they did. Laughing together, they almost didn’t recognize themselves…

That evening Charlie showed up at Rick and Sarah’s place with the winning bottle of Glen Fiddich 12-malt whiskey. They each enjoyed a shot while reminiscing their past friendship and discussing their plans for their future. It was good.