Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, Consensual, Reluctant, Fiction, Anal Sex, Cream Pie, Oral Sex, .
Desc: Romantic Sex Story: Chapter 1 - Rob's girlfriend Angie breaks up with him in a messy and public way. And that's a problem, because he needs to go to his BFF's wedding, and Angie will be there, which means he needs a date. Preferably one that will show Angie up. Then he wins a weekend with Ally, someone else's girlfriend, in a bet on a baseball series. Can he make this work? And will it lead to happiness for either Rob or Ally?
I’ve just returned home after spending the holidays with family. It was the best holiday season ever. Mostly, that was because over Christmas, I introduced my fiance to my family, and over New Years, she introduced me to hers.
All of my family, all of her family, and all of our friends asked the same question: how did you guys meet each other? And every time someone asked, I gave the same answer: I won her with a baseball bet.
Maybe I should start at the beginning.
My name’s Rob. I’m 26 years old, and for the past 5 years I’ve been dating and living with a girl that I met in university. Her name’s Angela. She broke up with me just over four months ago, on the Labour Day weekend. We were spending the weekend at a friend’s cottage, at the annual gathering of a group of us that had all been at school together. This year was special, because two of those friends, Ainsley and Ian, were getting married at the end of October, and the annual get-together had been turned into a kind of a buck and doe weekend for them.
I’d always had a soft spot for Ainsley. We’d never dated, and we’d never slept together. It was more like a sibling kind of relationship, I guess. She told me her troubles, and I told her mine. And I tried to look out for her when I could. I was so happy for her when she and Ian got together, and even happier when they announced their engagement last year at Christmas. The two of them were so wonderful together. They seemed to have been made for each other.
Angie and I, on the other hand, seemed to have hooked up out of convenience more than anything else, and I believe we stayed together because of inertia. I realize now that it was a doomed relationship from the beginning, but I didn’t see that then. So when Angie broke up with me, on the beach, on that sunny Sunday afternoon, in front of all of our closest friends, I was devastated. And heartbroken. And humiliated.
Humiliated? Well, one of the many things that Angie shouted at me, along with the fact that I was totally boring and I had a lousy deadend job, was that I was terrible in bed. She’d never said anything negative about my lovemaking skills before. But as I got in my car and drove back to Toronto, all I could hear was her ranting on and on about how small my dick was and how I always took too long to come and how bored she was with our sex life. I wanted to die.
Ainsley called me just after I left the cottage that day, and pleaded with me to come back. I said that there was no way I could do that. She cried. I assured her that I wasn’t upset with her. I just couldn’t be around Angie at that moment. Ian took the phone from Ainsley, and told me that he didn’t know what Angie was trying to do, but he was sure she’d soon realize what she’d thrown away and come crawling back to me. I laughed, and said she might as well save her breath, because I was done with her.
The month of September was pretty miserable. I hadn’t really realized how much control Angie had been exerting over how I spent my time. The upside was that I could spend my time any way I wanted to. The downside was that all I really wanted to do was be with Angie. I was so hurt, and I hated her. But at the same time, I missed her terribly.
So I started watching baseball again. Angie didn’t like sports, and she had gradually pulled me away from what had once been a pleasurable pastime. My evenings were free, so I could watch as many games as I wanted to. And my beloved Blue Jays were having a great season, and looking like they were real contenders for the World Series, for the first time since I was old enough to stay up and watch them play.
On the Saturday of the Thanksgiving weekend, I had lunch with Ainsley. She’d called earlier that week and asked if we could meet up. She was worried about me. And she had good reason to be, I guess. I’d lost some weight, and hadn’t been sleeping well. We talked about Angie, and the breakup, and how I was coping - or not coping. And then I told her that I didn’t think I could come to her wedding, which was only three weeks away. I hadn’t seen Angie since that fateful day when she humiliated me, and as much I wanted to see Ainsley and Rob tie the knot, I just didn’t see how I could face Angie, and I knew that she’d be there. She was one of Ainsley’s bridesmaids, after all. Ainsley had asked her, or so she told me, not because the two of them were particularly close, but because she and I were close. Ains couldn’t ask me to be a bridesmaid, but she could have me standing there beside her via proxy, so to speak, by asking my girlfriend to be a bridesmaid.
In all the time that we’d been friends, I’d never seen Ainsley cry like she did that day over lunch when I told her I was planning on skipping her big day. At one point she came and knelt beside my chair and threw her arms around me and held me like she’d never let me go. She begged me to change my mind, and come. She told me I could bring a guest, if I wanted to. I laughed, and asked her who she thought I could get to go with me. She said I could bring anyone I wanted, even one of my sisters, or one of the guys I worked with. That made me laugh again, though there wasn’t any humour in it. I could just see Angie telling everyone I was gay if I showed up at the wedding with a male friend in tow.
Finally, I gave in, and said I’d do my best to be there, because deep down, I knew that Ains was right. I needed to be her at wedding. And it would be a lot nicer to be there if I had a date with me, instead of just being there on my own, so I told her I’d bring a plus one. But who could I possibly take?
I thought about it all week, and no answer came.
On Friday afternoon, just as I was wrapping up work for the day, one of my coworkers came by. Jeff’s an ok guy - a bit rough around the edges, but his heart is in the right place. He shares my love of baseball in general and of the Jays in particular. The Jays had indeed done well. They hadn’t been able to pry the AL East away from the Red Sox, but they’d won the wildcard, and in the first round of the playoffs they’d beaten the Sox three games to none. That night, they were in Cleveland, for the first game of the American League Championship series against the Indians.
“Hey, man,” he said, as approached my desk. “You gonna watch the game tonight?”
“Of course,” I replied. “Nothing else to do.”
“Then why don’t you come watch it with me and my buddies? Baseball’s more fun when you watch it in a group.”
I didn’t have a good excuse to say no, so I agreed to join him. He was going to his friend Phil’s place. We stopped and got some beer on the way, and arrived just as the game got underway. Now, like I said, Jeff’s an ok guy. But his friend Phil was an ass. And Phil’s friend Mike, who was there too, was an even bigger ass. But I’ll get to that later.
We settled in down in Phil’s man cave, where he had one of the biggest TVs I have ever seen in a private home. Phil’s girlfriend, a cute but shy looking thing named Ally, about 5’3” or so, with blue eyes, shoulder-length dirty-blonde hair, and curves that deserved to have a warning sign, came in and brought us some chips and beer, then disappeared again.
The game - well, let’s just say that it wasn’t what I had hoped it would be. Cleveland wanted it more than we did. They scored twice in the 6th, and kept us from scoring at all. We actually got more hits than they did, but we just couldn’t convert them into runs. I love my Jays, and wanted them to win, but I could see that the season was over. Cleveland was going to take the series from us.
And like the total idiot that I so often am, I voiced that opinion.
Three pairs of eyes swivelled away from the post-game rehash on the TV to glare angrily at me.
“I thought you were a fan,” Jeff said, sounding hurt.
“Hey, I am. I want them to win. But there’s a difference between what I want to happen and what I know is going to happen. Cleveland is going to take the series.”
“No fucking way,” Phil sputtered.
“Sorry,” I said. “But I just don’t think the Jays are going to pull it off. They’ve had a good season, and they whacked the Sox. But the Indians are going to take this one.”
They all laughed, and Mike took another big gulp of his beer. It was his fifth, I think.
“You willing to put some money behind that big talk of yours?” he asked.
I’m not usually a betting kind of guy. But I was getting mad. Angie had taken a lot of shots at me. She’d criticized my job, criticized my life, and criticized my manhood. And now these three assholes were criticizing my ability to read a baseball game. I stood my ground.
“I’ve got a thousand bucks that says the Jays will win,” Mike continued.
I held out my hand.
“Wait!” Jeff said. “I want in, too. I’m good for a grand on the Jays.”
Phil was squirming.
“I want in,” he whined. “But I don’t have a grand. I’m behind on a lot of payments right now, and fucking Ally just got laid off a couple of weeks ago.” He thought for a minute. “Hey, you’ve seen her. She’s ok, right? How about I put a weekend with Ally up against your grand?”
I began to feel a bit sick to my stomach.
“What do you mean, a weekend with Ally?” I asked, even though I was pretty sure I knew.
Phil grinned. It wasn’t a good look for him.
“I mean a weekend with Ally. Anything you want to do. You pick her up Friday night, drop her off again Monday morning. I know, she’s not the best looking girl in the world, but hey, pussy is pussy. Right?”
Mike spoke up again.
“Fuck, man. I almost want to bet for Cleveland just for a shot at that. I’ve been wanting a turn with Ally since the day you started seeing her.”
“What’s she like in bed?” Jeff wondered. “Is she any good?”
“Shit, she’s not bad. She doesn’t respond very much. But a weekend of any kind of fucking you want to do has to be worth a grand, no matter what the bitch is like. Right?”
Jeff nodded. I was silent. I couldn’t believe we were talking about someone like this. But Mike wanted details.
“So, anything we want to do? Oral? Anal? Can we tie her up? Come inside her?”
“Anything you want. I’ll tell her she has to make you happy. I always wear a rubber with her, because I’m never sure who she might be doing on the side. But you can bareback her if you want to live on the edge.”
Mike looked like he might come in his pants at the thought.
“I want in. So how about if we make it a pool? Whoever picks the winning team and if it’s the Jays, the right number of games, gets the pot? Three grand and a weekend with Ally?”
Jeff nodded. Phil shook his head.
“Nope. That gives dickwad over there four chances to win and each of us only gets one shot. If he wants in he has to name the number of games too.”
I was mad now.
“I’m in. I say Cleveland wins it in ... five games. The Jays will take one, but that’s it.”
“Ok, I’m going for the exact opposite. I say the Jays win the next four straight and take the series 4 games to 1. Phil?”
“I think the Jays will do it, but they need more time. I say that they’ll take the series 4 games to 3.”
Jeff nodded. “I say the Jays do it in 6.”
“What happens if Cleveland wins it in 4, 6, or 7?” Mike asked.
“Then the bets are off,” Jeff answered.
We stood and shook on it. I tried to act like it was normal, but the whole thing repulsed me. Still, I was sure that Cleveland was going to win. Whether they did it in five games or not didn’t really matter to me. I didn’t care about the silly bet. But I was going to prove to these asshats that I knew a thing or two about baseball.
And, seriously, what kind of guy bets away a weekend of sex with his girlfriend?
Game two was played in Cleveland the next afternoon. I wanted to just stay at home and watch it there, but Jeff persuaded me to join him and the other two at Mike’s place. Mike had a much smaller TV, and he was disappointed that afternoon, because the Indians won 2-1. That meant he was out of the bet, and he wasn’t going to get into Ally’s pants.
Game three was Monday, here in Toronto. We met at Jeff’s place after work. Cleveland took the lead in the top of the first, and the Jays tied it up in the bottom of the second. But they couldn’t keep it up, and they lost the game 4-2. Phil and I were now the only two players in the wager.
Game four gave Phil some hope. The Jays won it 5-1. It was a 1:00 game, so we didn’t watch it together, but after it was over Phil texted me a picture of him giving me the finger. I threw my phone across the office. I didn’t care about losing the bet or losing a thousand dollars. But it sucked to think I might lose to him.
I needn’t have worried. Game 5 was also a 1:00 game, but along with most of the city we took an early afternoon and met up at a bar near where Jeff and I work. The atmosphere was pretty subdued. To win the series, Toronto had to win every single game. And that didn’t happen. Cleveland won, 3-0, and took the series 4 games to 1.
Phil was speechless. I think not winning the cash upset him more than trading his girlfriend away for a weekend. He’d likely already spent the three grand that he was so sure he was going to make. I went and bought us another round, and when I came back Jeff and Mike both passed envelopes across the table to me. Then Phil asked me if I wanted Ally that weekend.
I’d been trying to figure out what to do about that. At first, I had decided that if I won, I would pick Ally up, take her to a hotel downtown, pay for a room for a couple of nights, and tell her to call a girlfriend or two to come over. But then I had thought about Ainsley’s wedding. I needed a date. And Ally would be perfect, if she would do it.
“No, not this weekend. Next weekend?”
“Done,” he said, reaching across to shake my hand.
“Fuck,” Mike muttered. “I was really hoping to spend some time messing around with Ally.”
“Give me a grand sometime and I’ll make it happen,” Phil said, laughing. Mike reached over and clinked his glass against Phil’s. I didn’t like the look he had in his eyes. I drained my beer, stood up, took my money, and left.