Hello everyone. I'm back with our most recent sexual experience. For background, in the 10+ years we have been married, we have attempted anal sex once... and it was on our wedding night. It was obviously extremely unsuccuessful due to being young, stupid and not careful/prepared. I hadn't really ever pushed to try again because I knew how terrible of an experience it was both of us but mostly her.
Fast forward to the weekend. Trip all to ourselves, no children, no real schedule. We spent the day hiking and enjoying time to ourselves. We ate an amazing meal for dinner and return to the hotel for hot tub and hotel room sex.
We start furiously making out in the shower after rushing in from the hot tub. We have some foreplay including some clit rubbing and gentle tugging and eventually migrate to the bed in fancy robes. We sit on the bed and watch an episode of The Office on TV while playing with each others' bodies. We start disrobing in the middle of the weigh ins during Dunder Mifflin's weight loss challenge and during Jim and Pam's proposal. (Such a great episode btw). We go into 69 and while turning around, I reach over to the nightstand and grab our 7 inch vibrating dildo and start slowly fucking her with it. I continued to slowly insert the head of the dildo while licking and flicking her clit with my tongue.
Meanwhile, she's enthusiastically sucking my cock while still on her back. I increased the intensity of the dildo pulling in and out slowly as she moaned in pleasure. She started to get closer to orgasming and I pulled the dildo out and rubbed the tip along her asshole. She shivered and said that the vibration actually felt good along her asshole. We ended up fucking in missionary and in various positions before going into doggy positioning.
I start railing her while she is on her hands and knees and slowly, her head gets closer and closer to the bed until she is face down and ass up. I start rubbing my thumb along her asshole asking her if she wants me to continue, she nods. I end up grabbing the lube on the counter and lube her tight, pink asshole up as I ever so slowly insert my thumb while slowly fucking her. She starts groaning from the pressure but doesn't stop me. I pull my thumb out and attempt to slide the dildo in but stop and set it back on the nightstand. I pull my cock out and lube up her ass again and slowly start sliding my dick into her ass. After about 2 or 3 minutes of slowly sliding my cock in, she backs her ass up on me and engulfs my dick. Tightest feeling in the world. I just held my dick in her and kept saying "oh my God babe. I'm in your ass." Over and over. I still can't believe it happened. I slowly slid my cock halfway in and out for about 3 or 4 minutes until it became a little too uncomfortable for her.
I pulled out and cleaned up my dick and helped clean her asshole. After soaping and cleaning my cock, we resumed PIV sex and ended up eating her out again later. We both had intense orgasms and agreed that was one of the craziest sex sessions in years.
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from Gonewild Stories https://www.reddit.com/r/gonewildstories/comments/ltbzbl/anal_for_the_first_time_mf/
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