Vacation with my bf and his best friend [MF]

A little backstory. I am a 23 year blonde who is very outgoing and loves to make new experience. My boyfriend and I have been together 5 years and this is the story of how I ended up fucking his best friend on vacation.

Earlier in the year I went to Cuba with my boyfriend Adam and his best friend James. The three of us have always been very close. We would hang out all the time and James would often crash in the bed with us after smoking or drinking. So one day we were all on Adams bed talking about how we should go somewhere hot before the holidays. We googled around, found a cheap flight and hotel so we booked a 6 day long trip. We were so excited we started packing the next day.

Now to be honest I have always been attracted to my boyfriend more than anyone but his best friend has always been hot to me. I was excited to pack all my skimpy bikinis and shorts.Low cut shirts, my boyfriend liked to show me off anyway.

The day finally came and we shipped off. It felt like a long flight but we made it just as the sun was setting in Cuba. We passed customs, flagged a cab and headed to our hotel. We booked two rooms that were connected on the inside. We got up and settled in. It was a beautiful hotel. I instantly stripped my sweatpants off right in front of the boys. James was trying not to look but I caught him looking at my ass. My bf never minded when I was a little slutty sometimes which makes me horny lol. I went to the bathroom and changed into my bathing suit.

We all headed down and went for a dip while drinking some beer. My boyfriend was not feeling the greatest but James and I were splashing and laughing. James kept touching me at times and holding a stare it made me pretty hot but I thought nothing of it. We headed back up to rest up for the night. I was so hot from the pool that I was all over my boyfriend when we got into bed. We fell asleep after fucking.

I awoke in the morning to James shaking me asking to come down with him to breakfast. I rolled out of bed not realizing I only had a small tshirt on and my
pussy was right in plain sight. I giggled and covered my self quick telling him to give me a minute. I tried waking my boyfriend but he was still snoring. So I put some shorts on and headed down.

Fast forward a couple days. My boyfriend was very ill. Not sure from what but it was a bummer for the both of us. I had been hanging with James most times. But it was our last night now and I wanted to go out with Adam. He wasn’t able to pull it together and I was upset I couldn’t go out dancing and having a good time. He told me to have a good time with James and winked at me. I asked him what the wink was for and he said he could be your boyfriend for the night and laughed. I asked him if he was serious and he said if that’s what I want to go ahead but no fucking he said.

I was very intrigued and surprised after him saying that because he is usually wet protective of me. None the less it made me wet. I changed into a short jean skirt with my nicest thong, a low cut shirt with a matching bra. James walked in as I was finishing my makeup and told me I looked hot right in front of Adam.

James and I left for dinner and drinks. It was a great time. Good food and music. We both got a little tipsy. We were walking back when we walked by a club. James wanted to go in so we did for a little. We started to dance and after a little James came up behind and put his hands on my waist. I started grinding with him, my skirt riding up dangerously high as I was grinding on his dick. He was rubbing me up and down I could tell we were both horny af. He turned me around and just lunged in for a kiss. We made out hard while he had his hand up my shirt. I reached for his bulge and was surprised how big he was! We made out for a while before he asked if we should head back. We were walking and he apologized for kissing me and was nervous about my boyfriend finding out. I told him not to worry he said you could be his replacement. He laughed and said he needs to give the full experience jokingly.

We got back and my bf was snoring. I didn’t want to disturb him so I went to James room to watch tv. I changed into one of my bfs t shirts with just my underwear. I sat on the end of the bed before climbing in beside James. He turned to me and said jokingly if I wanted the full boyfriend experience. I told him he would have to work hard to beat out my boyfriend. He started to kiss me and before I knew it he had his hand in my panties rubbing my pussy. I started to moan as I reached down his shorts. I wrapped my hand around his dick and was shocked at how hard and big it was. He shifted down my body while taking my panties off exposing my tight pussy. He started to lick me and it felt so good. My boyfriend never does it and it honestly had been 5 years so it felt so amazing
I was trying not to scream in pleasure.

After a while of that I was so in the moment I just told him to bring his dick to my mouth and started giving him head. He moaned as I deep throated his big cock. I don’t think I ever had bigger. After a couple minutes he pulled out and started to rub his dick along my pussy. He asked me if it was okay to go in. I was so horny I didn’t even think and nodded my head. He thrusted hard into me making me moan. It felt so good, honestly the best I have ever had. My boyfriend was my first and now James was my second. His dick was so big it was stretching me out but it felt so good. He turned over and I hopped on top and road his dick for a while. He was all over my body playing with my nipples and squeezing my ass. It was so hot. He threw me off and turned me over. He slammed into me and started going fast. I asked if he was going to cum and he nodded. I never had someone cum inside me before but before I could say anything I felt warm cum shooting into me. It felt so good I couldn’t even talk. He pulled out and we kinda just lied there out of breath.

We promised to never speak of it again and that I would tell my boyfriend the truth. I headed back to my room and fell asleep. The next morning I told Adam about what happened but I left out the sex part. I told him we did oral and that’s it. He asked a bunch of questions but was not too mad about it. He said never again lol. We all still hangout and it’s not weird. Anyways that my story that I wanted to share the whole truth about!

Source: reddit.com/r/gonewildstories/comments/egb1s1/vacation_with_my_bf_and_his_best_friend_mf