I helped my friend try anal for the first time [Group]

Well it finally happened. I have been wondering when I was finally gonna get to see her have her first time. Ever since I showed her how enjoyable anal can actually be after letting her boyfriend fuck my asshole, I have been thinking about how we should set up a time for her to try it for the first time. If you don't remember from the story about it I posted a few weeks ago, let me briefly explain.

Basically I have this friend Josie who is dating this guy Josh. I met them while traveling and we ended up all moving in together for the rest of our trip. We have all been hooking up ever since we first met, and over the past few weeks we have spoken quite a bit about our different kinks and fantasies. During one of our talks Josh confessed that he has always wanted to try anal, but that Josie was too afraid to try it.

That is what led me to suggesting that I show them both how it is done. Anal is something that takes a bit of preparation and patience to actually have an enjoyable experience so I think that is something they both appreciated. When we finally did it I showed them how to get me warmed up with their tongue, fingers, and butt plug. And then when he finally put his cock in I was super turned on and ready for it.

It was super enjoyable for me and I came several times during the experience, and i'm pretty sure Josie was convinced that this could actually be something really fun for us to do. This all happened almost two weeks ago and we haven't revisited the topic since then. Until today. It was one of those rainy days where you don't really wanna go outside so the four of us were just sitting around trying to figure out what to do.

Josh and Josie were on the couch making out and at one point she pulled his cock out of his shorts and he was jerking him off right in front of Max and I. Totally normal as far as we are concerned. I was just thinking of different ideas for what we could do in my head when I remembered that we all agreed we were gonna try this at some point. "Hey Josie! Wanna try anal today?" I asked her.

Her hand froze on Josh's cock for a brief moment before she went back to stroking him, more slowly than before this time. She was clearly lost in thought. Josh was looking at her expectedly and after a few moments of silence she nodded. "Yay! I'm so excited" I said. And I really was. I wanted to make this as perfect as possible for her since it was her first time so I ran over to her and pulled her to her feet. "Come shower with me" I told her.

I dragged her behind me towards the bathroom and just as we were going in I told the guys "Meet us in the bedroom in twenty minutes". Then we went inside. I turned on the shower and we both stripped off our clothes. Personally I think showering before anal is a must, makes everything so much better. We got into the shower together and we switched off getting each other all soaped up and cleaned off. Not gonna lie we also snuck in a few kisses as well.

Once we were all sparkling clean we got dried off and went into the bedroom to meet Max and Josh. They were waiting for us exactly as we had told them to and they were both naked as well. It was honestly kinda funny they were laying next to each other in bed with their hard cocks in their hands. It was kinda hot to me. I had Josie get into the bed and bend over so that I could have easy access from behind. I was gonna warm her up just like she had done for me.

I started off on her pussy, just to get her horny and relaxed. Using my fingers at first but then my tongue I started to gently tease her clit from behind. As the minutes passed I started sliding my fingers into her and I could feel she was soaking wet. Perfect. I continued to finger her pussy and I let my tongue wander until it found her cute virgin butt. I got a little spit on my tongue and used it to lube her up slightly as I tongued her.

Eventually she was ready for my fingers and I told Max to grab my butt plug and lube from my bag. He went to grab it and I used just my spit to get one finger into her. "Just remember. Try to stay relaxed" I told her as I slid my finger in. She was doing great so far. Once Max came back with the lube and toy I ever so gently pressed the plug against her butt and after just about a minute I managed to get it fully inside. She looked so cute all plugged up like that.

I pushed it in and out gently to get her used to the feeling before telling Josh that he should fuck her pussy for a little while to get her really in the mood. He took position behind her and started fucking her while Max and I watched. When I thought she looked ready I reached over and I pulled out the plug. "Time for her other hole" I giggled to Josh and I watched closely as he ever so carefully slid into her. It took a few minutes but eventually his entire cock was inside her asshole and when I looked back at her face she had a satisfied smile on her face. This was going perfectly.

I laid down next to her and gave her a kiss as Josh started sliding in and out of her and Max decided that he would fuck me. I had my legs spread and Max slid into my pussy while Josie and I made out. I could hear and feel every moan she was making as her asshole got fucked and I was honestly having so much fun watching it. I grabbed her hand and she gave me a squeeze.

Eventually Josh really started fucking her hard and I wanted to make sure that she came so I reached down and started rubbing her clit and sliding my fingers into her pussy while he fucked her ass. Almost instantly her orgasm hit her and I could feel her pussy cover my fingers in her juices. It was so fucking hot.

Josh kept pounding her until a few minutes later he moaned and started to cum. He filled up her asshole with his cum and even after he was done cumming he still kept rocking back and forth. I could tell from the look on his face that he was euphoric from finally fucking his girlfriends butt for the first time in his life. Max started fucking me harder at this point and a few minutes later he ended up filling my pussy up too.

We pretty much wrapped things up after that even though I hadn't cum yet but its okay I was content. We did this for Josie anyways. She smiled at me and thanked me for making that amazing and I was honestly happy that she enjoyed it as much as I knew she would. I think every girl should make all her holes available to her boyfriends, and now Josie finally could.