My boyfriend and I had been into swinging for awhile by this point. We’ve slept with a number of couples. If you aren’t a swinger, you wouldn’t know, but in the swinger community a lot of couples are biting off a bit more than they can chew. They like the idea of playing with others, but in practice it’s usually the guy pushing their girl because they want a FFM threesome or they just want to fuck a new pussy.
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In practice, many couples (ourselves included) adhere to strict reciprocity rules. They only play to the level the other couple plays too. The problem is that it doesn’t scratch the itch that the men in the lifestyle have. To be smothered in more pussy than they can handle.
My boyfriend is one such man. He just wants to fuck beautiful pussy. He’s also fairly well endowed. One night, while we were chatting, I jokingly told him that we should just make a bet with the other couple and whoever wins gets both pussies that night. It was like a lightbulb went off in his head.
The idea was simple, the men strip down and measure up next to one another. The ladies decide together which cock is larger, and that cock is the one who gets to fuck both of them that night. The other man watches from the corner. If either side cannot get hard, they lose the bet and sit in the corner. If the “winner” cannot stay hard, they go to the corner too. If the man in the corner cums before the other man is done, he has to wait outside until the end.
Excited, we went about finding another couple interested in playing. Lots of single men with nothing to lose responded. Finally, a couple responded while I was logged in. I looked at their profile but there was no way to know his size. They were decent looking. The guy was older and relatively plain, but took care of himself, and the lady was about 5 years older but fit. We were used to the age gap being young for the swinger community. They weee from out of town and had a room. It was perfect, and we make arrangements to meet at the hotel.
My boyfriend was very confident on the way there. He’s a solid 8 inches and thick. Not that I was too invested, because I got to play regardless, but he excitedly talked about how he was in the top 10% of cock size and that at the other guy’s age, there’s no way that he is able to stay hard.
Ever meet someone and they aren’t what you expected? That’s what it was like when we met this couple at their hotel. She was very tall, which gave the optical illusion in the photos that her husband was of average build. In reality he towered over the both of us at 6 foot 5 inches and clearly pumped iron. He was a massive man.
My boyfriend saw my eyes and clearly was less confident now. We all introduced ourselves and chatted for a few minutes. My boyfriend texted me that maybe we should back out. I texted him reminding him that penis size isn’t tied to body size, so he’s just as likely to win. Besides, she’s gorgeous and worth the risk. He calmed a little and I suggested that we get our men hard for the measuring, and both men stripped with their backs turned to prevent peaking.
After a short blowjob from both of us ladies, the men signaled they were ready. When they turned, it wasn’t immediately clear who the winner is, so we got out the tape measure. The other guy was About 7.5 inches but way thicker, and my boyfriend was 8 inches but thinner.
The other guy suggested we decide by volume, and calculate the volume of the cylinder. Unfortunately, for the volume of a cylinder, diameter is more important than length. My boyfriend is about 25 cubic cm and he was over 50 cubic cm. If you want to do the math yourself, my boyfriend was 8 inches long with 2 inches in diameter. And the other guy, Derek, was 7.5 inches long and 3 inches in diameter. That one additional inch in width meant he was more than double the size of my boyfriend.
My boyfriend was suddenly pale. I looked at him with my “a bet’s a bet” eyes. And told him to sit in the corner.
I looked up at Derek towering above me, and asked him what he wanted. He just put his hand on both of our heads and lightly pushed down till we got on our knees. Even on my knees I needed to sit straight up, but I was level with his cock. He then told us both to make him happy.
We both went to work on Derek’s cock, alternating between which of us would bob, and which of us would lick. He moaned, before stopping us. He put his wife in doggie and asked me to get on top of his wife in doggie too, so that both our pussies faced him, and both of us face my boyfriend.
I watched my boyfriends face as the Derek entered me. I couldn’t help but let out a deep moan as he stretched me. My boyfriend’s eyes were wide. Derek pulled out and I suddenly felt so empty as I heard a similar moan from the lady. I could feel him thrusting through her body underneath me.
I felt myself dripping, and then he must have pulled out of his wife because in one thrust he buried himself in me and I closed my eyes shut with a loud “ugh!” He started thrusting hard and I started moaning, feeling my pussy be completely used up.
When I opened my eyes. I saw my boyfriends face was masturbating in the corner. We locked eyes, and I knew he knew from the embarrassment on his face. Our relationship wouldn’t ever be the same. His masculinity would never recover from this.
Here was his perfect hot little girlfriend, and because his manhood was too small another man was using her up. More embarrassing was that he was enjoying it.
Derek had his wife switch positions into a 69 underneath me, and then continued. He fucked me hard and I was moaning and gruntin loudly as he bottomed out, cumming over and over. He asked me how it felt, “full” I answered only able to make out single word answers.
His wife began licking my clit and Derek praised her for licking his balls too. “Fuck me Derek!” I yelled. I started moaning his name.
Derek looked over to my boyfriend and asked him “where should I cum.” But my boyfriend’s eyes betrayed him. He didn’t answer. Derek asked again, but this time he said “if you don’t answer I’m taking the condom off and giving her a creampie.” He started counting down from five, but didn’t receive a response.
I began to protest as he pulled out of me, but his wife wrapped her legs around my head and burried my face in her pussy. I felt him enter me again, and I knew there was nothing between us anymore, because it just felt right. I moaned into her pussy, as I felt Derek pump his hot load into me. I orgasmed right there.
I just collapsed on his wife and felt his cum leaking out of me. His wife began to lick me pussy before I stopped her by rolling off. She looked at me strangely before I spoke up.
“He’s the one who didn’t speak up. He wanted this, he needs to clean up his mess.” “You heard the lady, come over and lick her clean” Derek said motioning to my boyfriend.
My boyfriend meekly came over, kneeled between my legs, and began to lick me out. It felt amazing, and I felt so dirty it wasn’t long until I squirted all over his face.
By that time it was pretty late, so we decided to head home, my cum and Derek’s cum dripping down his face as he drove. I slept so well, dreaming of my next time with Derek.