An unsuccessful DP leads to back-to-back anal [MFM]

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 a story from that time.

One weekend night, the guy I had been hooking up with, Zack, invited me over to his hotel bar where a bunch of people were hanging out. He was on the island for a few weeks for work, and we matched on Tinder soon after he got here. He was maybe about 6’1″, had red hair, and was in pretty good shape. As for me, I’m about 5’3″ and 135 lbs or so, with C-cups and some curves.

I got to the bar and found Zack pretty quickly. It was super crowded, and it took a little while for us to get a drink. At some point his friend Mike came over and started hanging out with us. Mike was super hot, about 5’9″ and really muscular. I felt like he started flirting with me from the get go, and when Zack when to get some more drinks, Mike got closer to me and put his hand on my waist when we were talking. After a few more drinks, the bar was really crowded, and Mike suggested we go hang out in his room. I wasn’t sure where this night was going, but I was pretty turned on by Mike.

We get up to his room and he pours us some drinks. We were all sitting on his couch, and I felt myself getting closer to Mike as he was talking. He put his hand on my leg while Zack was telling a story, I remember thinking that I should ask Zack if he was okay with this, but I figured “why not” and leaned in and began kissing Mike. He immediately began running his hands lightly down my back, and I heard Zack stop telling his story. Not wanting him to be left out, I reached out with my left hand and began rubbing Zack’s cock over his pants. This continued for a few seconds before I leaned over and began making out with Zack while still rubbing his hardening cock. He reached down to undo his belt, and I pulled his hard cock out and took him in my mouth.

Out of the corner of my eye, I could see Mike had stood up and walked over to me, and I could hear him undoing his belt. I reach my hand out, and he took it and guided it to his cock. As soon as I felt it, I had to stop and look; it was enormous. Zack had a nice average sized cock, but Mike’s had to have been 2-3 inches longer and was super fat. I keep blowing Zack for a bit, until Mike pulled on my hand and led me to his bed. I pulled my dress off, followed quickly by my underwear and bra. Mike got undressed and lay back, and I crawled on the bed to him and started blowing. I was proud of myself for how much of him I could take, and it really made my mouth sore being open that wide.

Zack climbed on the bed behind me, and I could feel him running his cock along my pussy. He rubbed my clit for a few seconds, and then slid his cock into me. He fucked me slowly as I got in the rhythm of blowing Mike while fucking Zack, I’ve had a few threesomes before this, but it was definitely hard to stay focused with my mouth opened so wide. My jaw started getting sore, so I turned around to begin blowing Zack again. Mike rolled a condom on, and slowly slid in. It was really intense, and I had to stop with Zack until he was all the way in. I resumed for a few seconds, but was really uncomfortable with how deep Mike was going, so I suggested riding him instead. I slowly slid down his cock, but wasn’t sure how to involve Zack.

At that point, I got the idea to suggest a DP. I had never done one before, and was always turned on by the idea of two guys fucking me at once. Zack and I had done anal a few times, so I suggested he should fuck my ass. Everyone stopped for a second, and I think they weren’t sure what I was asking. They both said they had never done a DP, and asked me if I had. I’m guessing the alcohol made me think “how hard could it be?” They decided to give it a try.

I motioned to Zack to grab lube out of my purse, and I lay still on top of Mike while Zack lubed up my ass. He rubbed some on his cock, and then climbed up behind me. He slowly slid in to my ass, and I felt so full. It was a sensory overload!

They started going for a few seconds; I was really turned on as they both fucked me. Unfortunately, it didn’t last long, and Zack pulled out and said he was weirded out by their balls touching. I’m guessing he also felt Mike’s cock through the walls of my ass. I didn’t want to make Zack feel embarrassed, so I told him that I would fuck him after Mike.

My pussy started getting really sore; Mike had been in there the entire time. I suggested that he tries anal, which he readily agreed to. Zack handed him the lube and went to sit down on the couch. I turned around and slid down Mike’s cock in reverse cowgirl. I’m glad my ass was already warmed up from Zack. I rubbed my pussy, and felt an orgasm building. Mike also seemed really turned on, as he started breathing hard. I started cumming, and it seemed like Mike came right after. It took me a second to climb off, and then I lay down next to Mike while we both caught our breath. He got up, rolled the condom off, and walked over to the bathroom.

Zack took this as his cue, and walked over to the bed. He was clearly turned on from watching me get fucked, as his cock was really hard. He grabbed my legs and pulled me to the edge of the bed. He lined his cock up with my asshole, and started pushing in. It was really uncomfortable, and I asked him to reapply lube to make it smoother. He lubed up and slid back into my ass; I felt myself wincing as my ass was pretty sore after Mike. He put my legs on his shoulders, and pushed really deep into my ass. Before long, he was shooting him cum in my ass. He took a second to get the last of his cum out, but unfortunately his cock caused an embarrassing noise when he pulled it out of my ass. I lay there for a second to catch my breath.

It was getting pretty late, and I didn’t feel like getting dressed. Zack put his clothes back on and asked if I was coming, but I said that I would stay in Mike’s bed. We agreed to all me the next morning for breakfast. I spooned with Mike for a bit, and quickly fell asleep.

The next morning, we both slept in, and I hopped in the showed before breakfast. Mike joined me in there, and it wasn’t too long until I was on my knees getting him hard. He opened the shower door to grab a condom, and I told him he didn’t need one. I know this wasn’t the smartest decision, since I did’t know him at all. But at the time, I was really turned on and just wanted to fuck him. I put my hands on the shower wall and leaned forward, and he slid in cock in me. I was still pretty sore, but I didn’t want to leave the shower. This kept going for a few minutes, and I realized we might be late for breakfast. I started bouncing my ass on his cock, and it wasn’t long until he came inside me.

We cleaned up and got dressed, and went downstairs to meet Zack for breakfast.

Source: reddit.com/r/gonewildstories/comments/x1wcg2/an_unsuccessful_dp_leads_to_backtoback_anal_mfm

3 comments

  1. Okay first, fucking hot. Wish I could of given you a DP. It’s literally a dream of mine to give a girl one. Second, were you in the military by any chance

  2. I’ve only had one threesome and DP was so much trickier than I expected! We weren’t able to make it work. But it’s a huge fantasy of mine still

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