“A deal’s a deal” [MF]

Throwaway account for obvious reasons.

This story takes place pre-covid, I was 18 at the time, in a relationship, enjoying life. My bf and I decided to go on a vacation with my sister and her husband along with her brother and his friend. Confusing, I know, 6 people in total, 2 couples. Me, my bf, my sister, her husband, BIL, BIL’s friend.

As for my build, I’m an average woman, 5’4″, ample boobs and ass, decently fit. As for the man in this story that matters, my brother in law, he’s about 6′, also decently fit for someone who doesn’t really try, at the time he was 24. Not sure if more details are needed but that should give you a good enough picture.

Now onto the story, we all decided to go cancun one winter. This is a much different climate from what we’re used to in the northeastern US, so to escape the cold we decided to go to the always tropical cancun. We arrived, checked into our hotel, each pair had their own room with our room connected to BIL and his friend. Convenient, I know. Our first night in was tame however things got interesting on the second day.

During the second day, we all happened to be drinking a little bit too much at lunch. Inhibitions were low and filters were gone. We set up a ghetto beer pong table in our room after lunch and as drunk people we wagered sexual favors. However, I think that at the time we mostly believed that we were joking around but I had other plans.

I ended up going against BIL and while it was a close game I ended up losing (barely). He looked up at me and said, “A deal’s a deal!”. We made eye contact as everyone there laughed but moved on.

After we all finished up, us two couples decided to go down to the beach, leaving the other two in the hotel. We got down to the beach and I looked at my boyfriend and said “Hey I think I might be starting my period, I’m gonna go run up to the room, don’t wait for me”. Totally natural.

I got back up to the room and texted my BIL “A deal’s a deal, get over here”. Soon enough, the door connecting our two rooms opened up, he was still drunk but sobering up. He seemed timid, questioning the situation, but I insisted. I sat him down on the bed and got him to pull his pants down and out popped his dick. About 5″ in length, not a mile long like some stories on here but holy cow was it girthy, dude was packing some heat with his freaking soda can hanging out in his pants.

“Holy shit dude, I don’t know how long my jaw is gonna last”

“A deal’s a deal, my friend”

With my task ahead of me, I pushed onward, bringing my mouth closer to his penis. I closed my lips around the tip of his cut member. I used my tongue to play with the shape of his dick as he lightly moaned, tensions were high. My bf could walk in at any moment if he decided to come back and we could not use his room as his friend was in there. My eyes darted to the door every second it felt like.

I finally looked up at him and made eye contact as I was stroking him, he grabbed the back of my head and pulled my head up about halfway to his stomach. Unsatisfied with my ability to deepthroat him entirely, he started to stand up to fuck my face. Thrusting in and out, his dick started to really hurt my jaw. I pulled back and suggested we reposition.

He sat all the onto the back of the bed with me resting my head on his stomach. I started to suck his cock again, playing with the first two inches mostly to let my jaw rest for a second. After a few minutes I attempted to deepthroat him again, slowly making my way down his shaft using my tongue to massage him on the way. Although I did make it farther this time, I wasn’t able to get all the way down to the bottom. I started stroking him again while I gave some attention to his balls when he got a little impatient.

BIL got up from the bed, stroking his cock. I asked him what he was doing before he grabbed me and moved me closer to the center of the bed, getting me in position for missionary. I was still wearing my bikini at the time so he started to tug at my bottoms.

“Oh fuck I wasn’t expecting this” I said.

He threw my bottoms to the side and lined up his dick to my opening and inserted himself slowly.

“Dude, FUCK man” I wasn’t warmed up for this at all so it definitely hurt with him having such a girthy dick.

He kept fucking me on the bed for a few minutes, not seeming to care at all that there was a possibility that we could get caught.

Not going to lie though, while it hurt at first, his dick felt GOOD after a while. What he lacked in length he more than made up for with girth. He knew his way around my body. We changed positions a few times until we were back in missionary and he announced that he was going to cum soon. As much as I wanted it inside of me, I wasn’t wanting to take any chances. I told him to pull out but he made the best of that situation, he brought his dick right up to my face and came all over my face and tits. I sucked any cum off his dick to clean him off and shooed him away back to his room so I could clean up.

As for the rest of the trip, everything went by as normal without anyone finding out. My boyfriend came back to the room to find me resting and watching tv not suspecting anything.

Questions appreciated. DMs are open ;)

Source: reddit.com/r/gonewildstories/comments/n7jgvv/a_deals_a_deal_mf