Thank you so much to those of you who have been friendly and encouraging! It's nice to log in and see people taking an interest in what's been going on with me, Jen, and Brian.
To recap my last post, Brian was gonna be sleeping over at mine and Jen's apartment Thursday night and then all the way through the weekend. For those few days, Jen would have easy access to Brian several nights in a row and would be sleeping with Brian by her side in bed instead of me. Would she get bored of sex with Brian after having such easy access to him? Or would she decide that she liked Brian taking my place in bed for such an extended run? If Jen got bored of having Brian around, then I would be the winner of the bet. My prize would be getting laid more often. If Jen didn't bored and decided after the weekend was through that she wanted to be with Brian even more, then she and Brian would be the winners. Their prize would be Brian getting to stay over whenever he and Jen felt like it from now on: They wouldn't have to give me any advance notice whenever Brian was to take my place in bed; I'd simply take the couch with no complaints. As part of the prize, Brian would get some space in the closet for his clothes, some dresser space, and even a key to the apartment. It was a very big bet with lots at stake. I was already down to infrequent sex with my fiance, and even that was condom-only. If Jen and Brian won, I was looking at spending lots more time on the couch so Jen and Brian could be together regularly. I wondered what that would mean for mine and Jen's sex life if she and Brian won and Jen's sex life then revolved around Brian instead of me? To top it off, the odds were really against me. Jen had admitted that she thought Brian is a much better lay than me and that there's no comparison. Jen was going into the bet knowing that I was going to lose. I knew she wanted me to lose. On top of that, Brian had promised to fuck Jen so good that there was no way I'd win. So what chance did I really have? Probably no chance I figured. The thing is, even though part of me wanted for me to win the bet because I was so scared of everything that was happening, overall what I wanted was to lose the bet and to experience more of that feeling of helplessness of having Jen and Brian be a couple in our own home. As scary as it was, I figured I could deal with whatever anxiety the situation gave me because Jen and I would be married in a few months, at which point things would go back to normal. So, the bet was on!
To make the bet work, I had to give Brian a key to the apartment right away. If he was staying over several days in a row, he needed to be able to get in and out easily. Jen and I already had a spare key just in case, so I didn't have to run out to the hardware store to get a new one.
Thursday night was pretty non-eventful. Brian had picked Jen up from work that evening. The two of them got back late due to Jen's work schedule, so there really wasn't much time for me to hang out with them since I had to be up early Friday morning. We chatted a bit. All the while, the two of them were really affectionate with each other. Even though they were exchanging some pretty passionate kisses, I got a pretty basic kiss from Jen when she wished me goodnight. The highlight was when she whispered in my ear, "Enjoy the couch while Brian gets to work on making sure that he and I win the bet!" She smiled wickedly at me when she said it and I know that Brian overheard her. He was smiling too.
Anyhow, I could sort of overhear the two of them as they were in the bedroom talking, and giggling, and fucking while I was in the living room, on the couch. But, the volume wasn't unreasonable. The only thing keeping me up was my erection. I eventually got to sleep though and left to work Friday morning while Jen and Brian still slept in bed together.
Friday evening was nice. Although Jen and Brian were both still at work when I got home, Brian was done with his job before Jen and headed straight to the apartment. He and I had fun chatting and playing video games. We both went together to pick Jen up from work. I drove while Brian rode shotgun. He switched to the back seat and sat with Jen, while I drove us back to the apartment. They held hands, exchanged kisses, and totally acted like a couple. When we got back to the apartment, the three of us hung out, watched some TV, and talked. Jen eventually brought up the bet.
"So, are you curious how Brian did last night?" Jen asked me, smiling that wicked smile.
"Well, it was night number one, so I'm expecting that it was pretty great. But, the question is whether the two of you will get sick of being together several nights in a row?" I replied smugly, in a joking way.
At this point, Jen was laying down on the couch with her head in Brian's lap and her feet in mine. I was rubbing her feet while Brian was petting her. "I'm pretty sure you're going to lose, baby," Jen said smiling, in a very relaxed way. She continued, "It's like I'm sort of keeping score, right? I mean I'm not just deciding if I get sick of fucking Brian. Which, by the way, there's no chance of that happening. I'm also deciding if I'd rather have Brian with me in bed instead of you in on the regular. And it's not that I don't want you in bed with me. You're my fiance, so obviously I do. It's just when I think about how great sex with Brian is, I feel like I want to just have more of that instead. Does that make sense?"
I was so hard! I know that Jen was trying to explain everything to me, but all it did was just make me more hard hearing her tell me why I was doomed to lose this bet. I wanted more of her of her explanation. I wanted her to really drive home the point. So, I replied, "Well, you already told me that sex with Brian is apples and sex with me is oranges. Oranges are okay, but you love apples." I couldn't believe I was speaking like this in front of Brian. But, I was. I was letting him know what a much better lover my fiance thought he was.
"Exactly!" Jen exclaimed smiling. "Motherfucking apples! It's not that I don't want to be in bed with my fiance. But, if I'm keeping score, then the apples are just gonna keep winning out over the oranges! I fucking love apples!" Jen giggled.
Brian decided to chime in. Surprisingly he chimed in on my side. "It's good to have oranges too though. Vitamin C, right?"
Jen looked up at Brian and replied, "Actually Brian, apples have Vitamin C too! Just not as much as oranges. The solution is to have more apples!" Jen giggled.
"Oh shit, dude." Brian replied, speaking to me. "I really hope this couch is comfy enough for you to sleep on regularly! I think your fiance is gonna be busy getting at my apples these next few months!"
The three of us laughed. The whole thing was absurd. But, here we were. "The couch is fine, bro." I answered smiling. "But, lets wait for the bet to run it's course before the two of you start celebrating apple season."
"Apples!!!" Jen burst out giggling. Jen was massaging Brian's cock through his Jeans by this point. She continued talking while feeling at Brian. "I think the both of you need to take off your clothes."
I couldn't believe it! I thought it was going to be another sexless night for me! And maybe it still was. I didn't know for sure what Jen had in mind, but I was up for it. Brian and I got up and stripped, while Jen continued laying on the couch smiling and giggling occasionally.
"The two of you should wrestle," Jen said smiling.
So there Brian and I were again on the carpet, getting ready to wrestle like the last couple times this had happened. Jen got up and took off her clothes. She then watched Brian and I go at it. Brian won, of course, and had me pinned in that same position that he likes so much. Jen got down on the carpet and squeezed my balls tightly with both of her hands. I was so hard! Jen started to stroke my cock with one hand while she gripped my balls wit her other. "You already lost the bet, baby," she said to me in a seductive way. She let go of my balls with her one hand, but continued to grip my cock with the other as she started making out with Brian. We all got up and she led us to the bedroom, where she took turns making out with Brian and I and rolling around naked with us. At one point, Brian and Jen rolling around together turned into them fucking. It was beautiful! It seemed to me like Brian's cock belonged in Jen's pussy! When they were done, Jen put a condom on me and at first rode my cock a little while I lay on my back. She then put us into the missionary position and I fucked her until I came (into the condom). "Thanks for the oranges, baby," Jen said when I was done. Jen then turned to Brian and smiled and said, "And thank you for those amazing apples, boyfriend!"
Yep. Boyfriend. She'd already called Brian that before, but it was still weird to hear it. The three of us showered together before bed, which was nice. I mean it was bed for Jen and Brian and it was the couch for me.
That was Friday night. Things got really crazy Saturday night though. I'll try to get on here tomorrow to tell the rest of what happened over the weekend. Spoiler alert: I lost the bet.
