My Lifelong Friend Became My Fuck Buddy [MF]

This happened a couple months ago. My friend Hailey and I have known each other for 20 years. We have always been extremely close. People always thought we were dating in high school and college because of how close we were. The reality was we’ve never done anything. She is insanely hot. 5’6″, about 130 lbs, blonde with D cups and a smaller but nice ass and great legs. I always thought she was hot but I knew I never had a chance so my mind never let me get true feelings for her. We were platonic and I was very fine with it.

Anyway, she had won a contest through work and received a free week long cruise for her and a guest. 7 days through the Caribbean, balcony room, all inclusive food and drinks/booze. She was planning on going with her boyfriend but they broke up about a month before the trip. She asked if I wanted to go and I obviously agreed.

The first 2 days were normal, we had a blast hanging out and doing things on the ship. The 3rd day was a travel day so we were lounging by the pool having drinks. Eventually I was tired of the sun so I told her I was going to head up to the room and lay down. She said she was going to keep tanning and would meet me up there in a couple hours.

When I got back to the room, I was feeling a little horny from seeing her and other women looking hot in their bathing suits + the few drinks I had. I laid down on the bed and grabbed my laptop and pulled up an old sex tape I had made with a previous hook up to watch.

I was about 10 minutes into the session when I heard the door shut. I must’ve been too focused to hear it unlock and open. But by the time I realized Hailey had walked in she had already gotten to the bed area and saw my whole cock at 100%.

“Oh my god!” She shouted and turned around. “Holy shit oh my god! I thought you said you weren’t gonna be back for a couple hours!” I said as I pulled the blanket over me. “I got bored down there without you so I came up to shower and take a nap.” she said. “I’m just gonna go shower. Just uh, go ahead and finish up or whatever you want to do.” She said.

I didn’t even cum, I just put it away and laid down, the awkwardness I anticipated was too much to handle. About 10 minutes later she comes in and lays down, it’s completely silent. She finally lets out, “sooo, uh, did you end up cumming?” “No” I said with a half laugh. “Well, uh, if you want to keep going I won’t stop you. I feel bad I cut you off.” I was stunned. She wanted me to jerk off next to her? “Plus, I uh, kind of enjoyed the couple seconds I got to watch.” “Uhh, are you sure?” I said. “Yes, I mean I already saw it so what does it matter now”

I pulled my pants down and opened the laptop again. I was underneath the covers until she grabbed them and threw them off. I was now in bed with my cock fully out with this incredibly sexy girl next to me. “What’re you watching?” she asked as she took her eyes off my cock and on to the laptop. “Uh just a sex tape I made with a hook up one time. She was intrigued and kept watching the video.

“I don’t know how she handles that” she said during a part where she was giving me head. “I mean, I’ve never sucked one that big before I don’t think my mouth could open that much!” She said laughing. I know you all probably hate to hear people hype up their dicks, but it’s true. It’s not quite Johnny Sins big but it’s pretty darn close. Measured above 8″ before.

The alcohol and my hornyness took over. “Well, you could try and find out if you wanted.” I can’t believe I said that. But before I knew it, her head was between my legs. She tried her best but she was right, she struggled to suck it but she did her best. It still felt incredible and years of desire came fulfilled. She took her clothes off and laid on her back and told me to fuck her. I obviously complied and got on top of her, slow at first so she could get used to it and then harder and faster the wetter she got. I turned her over and began going doggy style. I probably fucked her for 5 minutes before I couldn’t hold out any longer.

“Where do you want me to cum” I asked. She flipped over and began jerking me off on to her face. I blew one of the biggest loads of my life and watched her get covered in it. We hopped in the shower after and laid back down.

We kind of laughed about it until she broke the ice. “Yanno, wouldn’t be the worst thing if that were to happen again.” she said. “I would definitely agree” I said laughing. “What if we just considered the rest of the week a pause in our friendship? Just do whatever while we’re here and back to normal after?” “Sign me up!” I said quickly.

“So, me and Nate (her ex) actually made a list of all the things we wanted to do on the trip” “Oh ya?” I said, and she showed me the list.

On the balcony. With another girl. With another guy. With another couple. On the beach. In the hot tub. With a crew member. With someone 50+. The list went on and on. “Well, we already lost 2 days, better start cranking these out!” I said. We laughed and made our way to the balcony to begin crossing that one off.

I can share some of the stories of the other ones if wanted…

Source: reddit.com/r/gonewildstories/comments/xfx469/my_lifelong_friend_became_my_fuck_buddy_mf