During my mid-20s, I lived on the island of Guam for a little more than a year. While there was a lot to enjoy about my time there, one of the biggest life changes I found there was how easy it was to hookup. I used to have a new partner every few months or so, but in Guam, I was fucking a new guy ever other week or so. This is one of those times.
After living on the island for a few months, I had managed to bag about 15-20 new guys, many of them tourists or military men. Most of my friends were in a similar boat, but they all had one up on me: they had all done anal. They encouraged me to lose my anal virginity, and I wasn’t opposed to trying it, but it never really came up in the moment.
One Saturday night, I was out drinking at my friend’s bar. I was shooting pool with some of my friends when an older guy brought over a beer and asked to play next. I won the game and started playing against him, and we got to talking. His name was Charles, he was in his mid-40s, and was on vacation from France. We hit it off and kept talking, even after I beat him, although seeing as I’m not very good, I wouldn’t be surprised if he let me win.
We kept chatting for a few more beers, and before we knew it, my friends were saying they wanted to head out to another bar. I told them that I wanted to hang out with Charles for a bit and would meet them all later, but we all knew that wasn’t actually my plan. Charles and I chatted for a bit more, and then he suggested we head back to his hotel bar on the beach in Tumon Bay. I agreed and called us a cab, and told my friend behind the bar that we were leaving. She winked at me and said “I guess I can close up now that you are sealing the deal!”
We got in the cab and sat silently. I was getting pretty horny and didn’t want to wait for us to drink another beer before the fun started, so I put my hand on his thigh and slowly slid it down towards his dick. I felt him beginning to get hard through his pants, so I just looked at him and smiled. We got to his hotel, and he took my hand and walked me straight towards the elevator, with no mention of the hotel bar.
Once we got to his room, he led me to his bed and I lay down. He got on top of me and we began making out. He was a pretty big guy, probably just over 6 feet, and had a bit of a dad bod. I was much shorter at 5’3″, and have a curvy figure with C-cups. He pulled my tank top off and struggled with my bra; I laughed and quickly undid it. With my tits out, he unbuttoned his shirt and began playing with my nipples, which really turned me on. I reached down and began rubbing his cock through his pants, and he was fully hard. He began moaning softly, and I used my free hand to unbutton my jean shorts and pull them down.
Charles stood up and pulled his pants down, revealing his fully hard cock. I motioned him over and put his dick in my mouth. He was average in size, which meant I could take almost all of him in my mouth. This went on for a few minutes before he pulled away and grabbed a condom from his suitcase. He rolled it onto his dick while I lay back, and he got on top of me and slid in. He fucked me pretty hard for a bit, causing my tits to flop around, which always makes me feel sexy. He was going pretty fast and breathing pretty heavily. I figured we would switch it up, but he started grunting and pushed himself all the way into me as he came. He collapsed on me and was breathing really hard. He leaned back and kissed me, and then stood up and took the condom off.
I got up to use the bathroom, and lay back down next to him. I was hoping we could have sex again as I didn’t get to cum, but he was clearly pretty tired and drifted off before too long. I closed my eyes and fell asleep quickly too.
When I woke up the next morning, Charles was still asleep. I played on my phone for a bit, but then decided I should surprise him. I pulled the blanket back and began giving him a handjob. He must have been only half-asleep, as he seemed to wake up pretty quickly. He reached down and began fingering me, and before too long he was fully hard and ready to go again. He grabbed another condom, and I got on my hands and knees on his bed.
He came up behind me and started fucking me doggy style. Not wanting a repeat of the night before, I reached down and started rubbing my clit immediately. He took his thumb and began rubbing my asshole; before too long he started fingering my ass. This really turned me on and pushed me over the edge, and I began cumming loudly.
Charles stopped suddenly, and said his line I won’t ever forget: “Can I fuck your bum?” I don’t know if his word choice was intentional or just the result of the language barrier, but it seemed so forward and sexy at the time. I just nodded and kept rubbing my clit, while Charles went to grab lube.
At this point, I definitely felt my nerves going crazy; anal was finally happening! Charles returned and lubed up his cock, and then rubbed lube on my asshole. He put the head of his dick at my back entrance and pushed. I think he got maybe an inch in before I yelped in pain; I just felt so full! He stayed there for a second, and reached down to rub my clit. He pulled out and started again, going about the same distance again. It felt better this time, and he pulled out again. He kept easing himself in a little more each time, and maybe 10 minutes after starting, he was all the way in!
He started fucking my ass slowly. My ass felt so full, and I was going crazy from all of the new sensations I was feeling. I reached back to replace his hand on my clit, and we rubbed it together for a few seconds before he pulled his hand back and grabbed my ass. I felt my ass crashing into his hips, and had another orgasm. He started picking up the pace as well, and started cumming in my ass. We both lay down, breathing heavily, and he had his arm around me.
We lay there and chatted for a bit, but I had to leave to go to brunch. I got dressed, got his phone number, and kissed him goodbye. When I got to brunch I told my friends what happened, and they all jokingly applauded. I wanted to see Charles again, but unfortunately he left a day or two later, and we never had a chance to fuck again.
Source: reddit.com/r/gonewildstories/comments/vnh0c9/losing_my_anal_virginity_to_a_tourist_in_guam_fm