My (Taylor, 20M) GF (Becca, 19F) and I have been getting into cuckolding over the past couple months (see previous stories on my profile) but last week we decided to head out to the beach for a few days. Some old friends of Becca’s were renting a beach house for the week and we decided to book a hotel just a block away. While we planned to hang out with her friends while we were there, we also planned to have some alone time and I was happy to get her all to myself for once. I will have to split this into multiple parts so it doesn’t get too long.
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We arrived at the hotel and started getting dressed and I admired Becca’s athletic physique as she tried on different swim suits. Her toned body was going to be on display for plenty of guys at the beach but I was going to be the only one fucking her that week. I got up and put my hand on her ass and pulled her in for a kiss while telling her how beautiful she looked. “You don’t look so bad yourself!” She shot back as she rubbed her hand down my chest, over my stomach and finally resting it over my shorts massaging my dick for a minute before letting go and getting dressed. “Easy now you horny boy, we have all week and I told my friend Kayla that we’d head over there once we dropped our stuff off.
With that, we started waking over to the beach out. On the walk, Becca was telling me who would be there. Kayla was her best friend from high school and would be there with her boyfriend Jack. Steph would be there with her FWB Nate. Becca made it a point to say that they weren’t together but were just friends. Finally, Jack and Nate had invited a few of their friends so there might be a couple other guys from their friends group there.
We walked into the house and were greeted by Kayla and Steph who were drinking some wine. I thanked them for having us over and Kayla said they were so happy we could make it and she was glad they finally got to meet me. Steph handed me a beer saying “Becca, you didn’t tell us how cute he was” as she winked at me. “Taylor, the guys are outside on the deck if you wanted to go meet them.” Becca told me to go on and that she’d see me in a bit. I walked out back and and the group of guys paused their conversation and looked at me. Jack finally spoke up “You must be Taylor, Becca’s boyfriend right?”. “That’s me, nice you meet you all” I responded. As I grabbed a seat, Jack introduced Nate who said he was there with Steph. Jack laughed “are you two finally together?” He asked. “It’s complicated” Nate replied. Then George who was one of their friends and finally Jason. As I met Jason, I immediately knew who he was from the videos Becca showed me. This was her ex. “Great, her big dicked ex is here” I thought with a bit of jealousy.
I immediately noticed how good looking they all were and my first thought was that I needed to hit the gym more. Jack, Nate and Jason were all about 6 feet, white and in great shape and George was a tad taller, black and also looked liked he worked out. They were all nice but I could tell Jason was sizing me up at first but then seemed to warm up. I quickly forgot about Jason fucking Becca as we were all drinking and joking. The girls came out and Becca said hi to all the guys until her eyes locked on Jason who said “Hey Becca, it’s been a while. You look great!” She responded “oh hey Jason, it’s good to see you” but she then gave Kayla a look that said “why didn’t you tell me he’d be here”. Becca then gave me a tight lipped smile and shrugged suggesting she didn’t know he’d be here and I smiled back tilting my head as to say it’s fine.
Kayla said we should all head down to the beach and go swimming and we spent the next couple hours swimming, playing volleyball and relaxing. I noticed Kayla and Steph were both very fit, just like Becca, and I assumed they probably played sports together in school. Kayla was a cute freckled redhead and Steph had brunette hair but both had toned bodies, great asses and nice boobs. It was just an observation and I made it a point to not check them out since I was here with my girlfriend. However, I couldn’t help but notice that Becca kept glancing in Jason’s direction and then looking away. While I was jealous, Becca said she’d be mine for the trip.
Later we all went back up to the house for some pizza and drinks. We kept drinking and chatting with some music going and I noticed Jason and Becca had slipped outside and were talking on the deck. They were only out there for a few minutes before coming back in. Becca sat down next to me and started kissing me which prompted George to tell us to get a room. With that, Becca said that we were going to get going since we were all meeting up for breakfast tomorrow. We said goodnight to everyone and walked back to the hotel. On the walk back, I asked her what she talked to Jason about and she said he had asked how serious we were and if she was happy. She told him that she was and that was it.
Once we got back to the room, I started kissing Becca’s neck while removing her top and rubbing her nipples. She then started rubbing the front of my pants and asked “were you jealous seeing me talking to Jason?” I said I was and she started pulling my shorts down and took my dick in her hand and began stroking me. “Tell me what you were jealous of.” She said. “Well, you two used to date and, uh, you know” I responded. She came back with “no, I don’t know. Tell me.” I then said “that he has a huge cock and used to fuck the shit out of you.” She kept stroking me and finally took me in her mouth and started moaning, which felt amazing on my dick before pulling my dick out of her mouth and telling me that she loved fucking his huge cock.
Becca then got up and walked over to grab her phone. She turned on the tv and started screen mirroring her phone to the tv and went searching for the video of her blowing Jason. Once it was playing, she came back over to me and got back to sucking my dick while I watched her sucking his cock on the tv. “Watch how I suck his big fucking cock” she teased me. I watched as she used two hands on him, which barely wrapped around it, while sucking the head and when I looked down at my own dick she only needed one hand and it easily wrapped around my whole dick. She kept talking about how much bigger his cock was and how he fucked her so much better than I could. Finally the video was at the point where he was cumming in her mouth. “Look at how much Jason cums! I want you to cum now watching him fill my mouth.” I immediately started cumming and Becca took my cum in her mouth and got up and put my dick inside of her and started riding me while sharing my cum with me. “Imagine if this was his cum I spit in your mouth. Would you like that?” She asked. “Yea, I’d love for you to share his cum with me” I told her.
She rode me for a few more minutes while talking about his big cock before I flipped her over and started fucking her from behind. I kept fucking her as hard as I could as she told me to fuck her like Jason would. She then told me to get her dildo from her bag and when I brought it to her, she started rubbing the tip of it against her lips and sliding it in. “Fuck me in the ass while this big dick fucks my pussy” she told me. I lubed up my dick and started sliding it in her ass. As I fucked her, I could feel the dildo sliding in and out of her pussy while she kept moaning about Jason’s big cock. Soon she was cumming and I could feel her clenching on my cock which caused me to start cumming in her ass. We laid there for a minute before going to the bathroom to cleanup and take a shower.
After our shower, we were lying on the bed watching a movie on the tv and I leaned over and started kissing her neck. I then asked if she wanted to fuck Jason again and Becca looked me in the eyes and told me that while she would like to, she wasn’t planning on it this week. She then said that if she was going to fuck anyone besides me this weekend that it would probably be George because she had heard back in school that he had a huge black cock. I was getting hard again and started rubbing her pussy. I went down and began eating her out and asked her to tell me what she’d do to him. She described how she’d 69 him and suck his big black cock while he licked her pussy. As I got up and started having sex with her, she started telling me how much bigger he probably was and how much better his BBC would feel inside of her instead of my little white dick. I couldn’t take it much longer and pulled out and shot my third load of the night all over her stomach and tits. I began licking my cum off of her and leaned in and kissed her before we drifted off to sleep.
They next morning, Becca and I got ready and as we were leaving the room to head to breakfast with everyone, I looked over and saw Jason walking out of the room next to us. Becca’s eyes went wide and she asked “what’re you doing here?” He said that there wasn’t any room at the beach house so he had to get a hotel room because George had taken the last bedroom in the house. She laughed nervously and said we’d better get to breakfast. At breakfast, we were all chatting about what to do that day when Jason yawned. “You tired man?” Jack asked before stating “you went back to your hotel pretty early, like right after Becca and Taylor left.” Jason said “I’m fine, it’s just there’s a couple next door who kept having sex and I could hear everything they were doing and saying. It was some pretty kinky stuff too.” He said with a smile.
I looked at Becca and she turned bright red but she was thankful no one was looking at her. I looked at my food and didn’t say a word but just kept trying to remember everything we talked about last night and what he could have heard. “Great” I thought “now her ex boyfriend, who is bigger and better in bed than I am knows that we get off on her fucking bigger cocks than mine.” He didn’t go into detail about what he heard but Kayla said he probably enjoyed it too much and called him a pervert in a joking manner. They all laughed and I saw Jason look at Becca. She met his gaze and then immediately looked away. We finished our breakfast and left the restaurant to head back to the beach house and enjoy the day swimming and hanging out.
I’ll post part 2 tomorrow!