My Girlfriend and My Best Friend

Note: True story shared with me with a request to post it as a first time cuckold experience for the requester.

My girlfriend (let’s call her Emma) first mentioned a while back about a wet dream she had about my best friend. When she first told me, I was immediately aroused. I kept cool about it and very slowly, I started to encourage her to explore that desire a little more. As her desire progressed and got stronger we started fantasizing about it, talking specific scenarios in the bedroom. It started to become more and more frequently. At first she was hesitant but eventually she started to relish in the idea of me jerking off to her fucking my best friend.

One day we found out that he had broken up with his then gf. We saw this as a chance. Emma was happy to start texting him to cheer him up. Then she started to cross the threshold of the cuckold world. She messaged me asking if she can start hitting on him and I obviously tell her to go ahead. They were talking on snapchat and she starts sending me the snaps she had sent him. Soon enough, she's teasing him and then full on sending him nudes and close ups of her cute little pussy. He eventually started to respond with snap videos of him jerking off. According to her he is considerably bigger than me and this really excited her. She told me in detail about the girth and told me how much she would want to feel his size. She had never felt someone as big as him inside her. They continue doing so once or twice a week for about a month.

Finally the perfect opportunity to take the next step comes up, her birthday. Her parents and sister left her the house to enjoy herself for the occasion. She decided to invite a few friends for a party. Amongst the invited guests was me, 6 friends and my best friend. I was the first one there and the conversation I was hoping for came up. I had already got her a really nice present but she said what she really wanted was ti fuck my best friend for her birthday (We’ll call him Dean).

Everyone came over and we were all having a great time together however throughout the evening I could see the sexual tension was ramping up especially with each drink they took. They kept giving each other looks, fucking each other with their eyes, I even saw him grab her ass when no-one was looking. For about 10 minutes Dean got up and went to the kitchen where Emma went to grab some snacks. When she came back a couple minutes before him her face was red and she was smiling. She texted me immediately and said “Dean pressed his dick against my ass while I was in the pantry!! I turned around and grabbed it and holy shit! That thing is a python. I can’t wait to feel him inside me later baby ” That message made me rock hard and made it hard to focus over the next couple hours.

We had a great evening, play some drinking games, shared many laughs, all the while though I saw Emma and Dean texting back and forth. Dean probably had to adjust his pants a dozen times or so. At some point, everybody was getting tired so we decided to call it a night. We had planned for everyone to stay the night so we start setting up the inflatable mattresses and couches for everyone downstairs while my Emma and I went to go sleep in her room upstairs.

As we finish getting ready for bed, Emma grabs my hard cock, pushes me against the door and tells me to go to her sister’s bedroom and to wait there untill she tells me I can come back. I knew exactly what that meant and got very excited. I go and wait, I'm already naked and jerking off in her sister's bed thinking about what's gonna happen. I am just hoping our friends don’t realize what's going on. The anticipation is killing me and then I finally I hear it, someone opening her door and closing it again. I listen attentively, and soon enough, I hear them start moaning softly. It gets louder and louder, she's absolutely loving it. I can hear her begging for it, moaning, and getting spanked hard.. As they get more passionate they get louder and the bed starts squeaking loudly as the head board hits the wall. I am so horny but also worried, at this point because they are so loud that I confident that all our friends downstairs are hearing her. Since they were all sleeping in the same room, there's no way they wouldn't realize his bed was empty.

They keep going at it literally for hours, I don't know how he kept going but he did. I could hear her begging for him to cum inside her and from her moans I knew he did. This whole time, I'm just laying in her sister's bed, jerking and cumming repeatedly while listening to them and imagining what it would be like to be in the room.

She had told me that she would just fuck him for a bit and then send him back downstairs and that I would be able to go back and sleep with her so I kept waiting for a message telling me I could come back. After hours, the noises started to fade, I could hear an occasional moan but then it stopped. I could tell she decided she wanted to cuddle him and sleep with him. That meant they would end up joining everyone downstairs together in the morning, removing any doubt of what might've happened. I end up falling asleep while hoping for a message to come back to bed, or a video of some sort.

I wake up in the morning, still naked in her sisters bed, dried cum on me and the sheets. I check my phone but no message, then I hear a knock on the door, Emma opens the door and enters She smiles at me and I see fresh cum dripping down her chin, she obviously game him morning head and came to see me right after. Before I say anything she kisses me while she takes my hand and brings in into her pants to touch her pussy. I feel the dry cum all around her pussy but then I feel how wet she is. As she wiggles her tongue all around my mouth I can taste his cum. We then go downstairs, he was already there, apparently he went down first and told our friends he went up to take a shower. However, from the stares we got that morning, I think they knew what really happened.