The Contest

The Friend

Well, look who showed up again, thought Katie. She was looking at the 'friend request' from Paul. She had not seen Paul for several years. He had had so much potential. They had had so much fun. For some reason, Paul had backed away, and she wondered if she had pushed him too far, too fast. Katie had a need to push. No reason why, other than life was too short to not have the chance to see everything she could, share it all, and mostly have that lovers' bond that came from a 'no secrets' outlook. She had to push to make sure she was investing her heart and soul, not to mention her body, with those she could continue to grow with for a long, long time.

Katie accepted the friend request.

Paul found Katie again. They had moved a couple of times since they split up. Well, since he ran away. Paul had a girlfriend, the latest of several since Katie. The sex was good. Good, satisfying fucking. But there was not much play. Any suggestion of play seemed to lead to the safety of some oral, lots of kissing, and the fucking. He missed Katie and her wild ideas. With Katie, there was plenty of time for fucking, but there was also plenty of time to use play to bond together. He often thought he had been stupid to pull away from Katie. Had he been embarrassed? Maybe a little, but Katie was so much fun, and she would never judge another's kinks, nor condone any judgement of hers. Nobody like her, he thought.

He sent her a message and she replied. They chatted online here and there, spoke on the phone. Sometimes he let it slip that he missed the fun. She said she did too.

"I have business in your town this weekend," he announced one day.

"We'll have to get together! It will be so much fun!" offered Katie.

"Fun," he thought. That had a really broad definition with this woman.

"I'll have a surprise for you when you get here. I won't tell you now, who, I mean what it is."

Paul wondered about that slip. Could it be? Katie had been very open about sex, and he knew she was attracted to other women. Her profile pictures showed her with a particularly stunning lady, going everywhere together. He wondered if she had ended up with a girlfriend. His mind raced at the thought of finally getting that three-way with two hot women, both of them worshipping his cock. He was not sure, but was really looking forward to their reunion.

Katie opened the door for Paul with a big smile. "Paul! It's been so long!" She gave him a hug that had her practically melting in his arms, then he looked past her to see...

"Paul, I want you to meet James," Katie said. James rose and shook hands with Paul. Large hand, strong grip.

Not what Paul had planned, nor fantasized about (what a dummy I am, he thought) but the company was good, relaxing, and Katie knew how to put them at ease. The micro-brew beer was very good too. Here they all were in the big hot tub out back. They'd undressed in darkness and were in the water now, Katie between them, but there was no real contact between anyone.

"Time for refills?" she asked. What a great hostess. She got out of the tub and walked across the deck to the house to fetch them. The moon was bright now so Paul and James both appreciated a fine view of Katie's pretty bottom as she walked away from them.

Now it was just the two of them, two naked men in a hot tub. A little uncomfortable. Of course, they caught each other's wistful looks at Katie's unashamed nude body.

"She's really something," offered Paul after a long silence.

"She's absolutely amazing," countered James.

"I guess she was what I would call 'scary-amazing'," said Paul.

"She is all of that!" laughed James. "Imaginative. She is big into play, and sometimes big into toys, or I should say into big toys."

Paul realized then how certain it was that James too, had submitted to being taken by Katie's strap on. Maybe the same one she had used on Paul. 'In that way, we're like brothers,' thought Paul to himself.

"Ha, I knew things would get very interesting whenever she said, "Let's play!"

"Yeah, but you really have to watch out when she says 'I have an idea', said James.

The both smiled and would have clinked their beers together in a toast, but they were empty.

Just in time, Katie was back. She walked slowly towards them in the soft moonlight. She held a beer in each hand, and she gave them ample opportunity to admire her body, her barley-there breasts and her shaved pussy. She gave them a long look to set the mood for what she had in mind.

"Let's play!" said Katie. "I have an idea!"

The Idea

She took their hands and led them out of the tub, into the house. Two gorgeous men, nude, soaking wet. She handed them towels and said, "Don't drip on the floor, dry each other. Here is what we will do. We need a contest. It's a contest with a winner and a loser, but the loser still wins a mind-blowing journey past any barriers he might have had. In our contest, it will be 'winner take all'."

"What does the winner get?" asked Paul.

"The winner," said Katie, then she paused... "The winner gets to do anything he wants to do."

The unsaid part of what Katie said was, "to anyone".

"Game on? My rules?" asked Katie.

Paul considered. He hated that he had been afraid to keep Katie. He would not let that happen again. James thought about it. He was enjoying being the man in Katie's life, but this new guy, he might be a challenge. They both nodded their assent.

Katie, still nude and pretty, disappeared for a minute and returned with a toy, It was a double-ended dildo, at least 12" from tip to tip, with a red line painted around the midpoint.

She pointed the the red line. "This will show who wins".

"You'll both lie on your backs, your head this way (to Paul, she pointed right) and yours this way (to James, she pointed left). Your balls and cocks will be close to each other and close to me in the middle. I will position this toy so that one end is barely penetrating each of you anally. When I say 'go', you will attempt to push the other end into your adversary. The loser is the one who has the red line inside when you are balls-to-balls, and not before."

"Um, is that thing going to be lubricated?" asked James.

'Wow, that's his only question?' thought Paul to himself.

"I will lubricate it, and you are each responsible for lubricating yourself," said Katie. Think about it, because some or most of this will go inside you. Do you want it in there with a lot of lube or not enough?"

Katie handed them each a tube of KY and said "Don't be embarrassed. Lube up. You will be thankful soon."

Quite humiliating, in a way, each man standing nude in front of another man, applying lube to his own anus. What we do for the love of a woman.

Katie had no idea how this would turn out. She had enjoyed taking each man anally before, but who would win?

They got into position and Katie lined up the dildo, having them move a little closer to make sure each tip was properly started in its target. She would have to hold the dildo at the start, to ensure no cheating. It could not be allowed to slip out of either man, giving him the chance to use a leg or other surface to push it right into his opponent. She considered that the quickest way to lose would be to naively try to win by pushing out. Everyone must know that the quickest way to have something slip up your ass is to push out on it.

They began slowly, carefully, and moved a little closer together. She was running out of space for her hand on the dildo, and she let go, as the dildo seemed to be well planted at each end now. Instead, Katie took a cock in each hand as she watched. They continued to struggle under her and she imagined that holding the two cocks was like holding the horns of a small beast as it struggled, or holding the twin controls of a powerful machine that rocked and moved beneath her. She knew these cocks well, but to see them together, both the same size, one circumcised, one not. She would relish close inspection and comparison of that.

The Winner.

At last, their balls were firmly pressed together, and the two cocks were back-to-back. Katie used her fingers to gently pry apart their balls and peek below. Right there, in the very small space between the two stretched openings, was the red line!

'Unbelievable,' Katie thought. She looked at their faces. There was no look of triumph for either man. She was sure that they both felt so penetrated, so violated, that they surely had lost. There could be no 'draw' however, so Katie would decide, and tell one of them he had ingested past the line. They'd never know.

Paul is the one with the most to prove, she thought. He wanted to be back in her life. She'd make him the slut today.

"Good work, James!" she said.

They boys slowly separated, letting the toy slip out. James looked triumphant now, Paul looked crushed.

"Let's get started, boy," crowed James. "I'm called 'Sir'".

James guided Paul to his knees on the floor and stood before him, 'Cocky' in every way.

"Can you see okay, Katie?" asked James.

"Wonderfully," she answered.

"Okay boy, your job tonight is to keep this hard for the lady, and for me. Get to work."

"Yes Sir".

Paul closed his eyes and opened his mouth. James' cock was really not bad. It tasted fine and the texture was pleasant. Of course, the fact that Katie had set this up and was watching so lovingly inspired him on. He sucked on it, licked, then sucked some more. Katie just beamed with pride.

Paul's mouth and tongue were well used for the rest of the night. While Katie and James were passionate lovers, Paul was an always ready, always eager helper. Katie got to enjoy the feeling of his tongue on her clit or on her anus while she was being fucked, and a few times 'Sir' also enjoyed the boy's tongue on his sensitive ass and balls while he took Katie.

At last, Katie held James' cock and stroked it slowly into Paul's open mouth. The semen was hot on Paul's tongue. He swallowed.

"You did a great job, Paul" said Katie "You are such a good sport. I have an idea!"