Hello everyone, hope you’re having a great start to the week. I’ve been exploring anal a bit more lately, really starting to get into it now and it reminds me of the first time that I tried double penetration so I thought I would share!
I was 19 at the time and dating a mediocre guy, Chris (same guy I cheated on with my first real sex with another girl, check my profile!) and was starting to wonder about really being filled, both holes at the same time. We had already had another girl join us and I wanted to see if we could have a guy join us next. He thought it was very hot and agreed that if I could find a guy, he would be up for it.
I had a bunch of guy friends at the time so it wasn’t a struggle but I chose Justin, an attractive, blond guy that I knew was into me. When hanging out one night, I pulled him to the side and nervously asked if he would be interested. He seemed very surprised but was up for it.
He came over a few nights later and it started so awkwardly, like a first date. We were talking but we all knew why he was here and the tension was building. I didn’t feel like continuing the small talk and looked at my boyfriend to see if he was still game. He seemed to know what I wanted to do, so I went over, straddled Justin and started kissing him.
Chris sat and watched while Justin groped me, dry humping on the couch as we made out. I could feel his dick, hard as rock in his shorts and being watched by Chris while grinding against him was really doing it for me.
Chris came up behind me and when I finally released from Justin and opened my eyes, his hard dick was right at eye level, waiting for me. Immediately, I started sucking on it while Justin unveiled his member, much larger than I thought he would be. He hiked up my skirt, pushed my panties to the side and entered me.
Now I was nervous. I hadn’t anticipated him being so big and I was still relatively new at anal so I knew I couldn’t handle him. It was in the back of my mind as I was being fucked by him that he may not have been the best pick.
I think he sensed my trepidation because when he picked me up and took me into the bedroom, he never pulled out. Instead, he sat down with me still on top of him and laid back, his length still inside my pussy. Chris had already begun to lube up and had a devilish look on his face, while I mentally prepared for the main event.
Chris was the smaller of the 2 but my ass was still an amateur so he took his time. First the head then slowly entering me completely. I was stuck between them, full of cock and it was indescribable. I had made sure to have a several drinks beforehand to make it easier for me and through the drunken haze, it was all so much.
Both their bodies against me, both fucking me, both of them here for just me, it was all so hot and I was thoroughly enjoying myself. I felt so sexy, so desired while they were both inside me.
Chris came first, spraying cum on my back while Justin kept going at me. Once Chris had backed off, Justin really had at me, showing Chris how it was done. He had me by the neck while I was on top of him, cum dripping down my back still until finally he came inside me.
I felt used, very dirty but very satisfied. I somewhat limped into the bathroom and immediately got into the shower. When I came out, both of them were back on the couch, watching tv as if they hadn’t just had their way with me. Justin gave me a kiss goodnight and left, thanking me for picking him to join in.
He never said anything to our other friends (a lot of which I eventually had sex with one by one but that’s a story for another time) but every time we hung out, he was always more attentive to me and would sneak small touches when he could. Grabbing my waist, a hand on my ass, a finger or two between my thighs while no one was looking. It definitely kept me wanting more.
Source: reddit.com/r/gonewildstories/comments/przybf/my_first_double_penetration_loved_feeling_so_full
That’s super wild