[FMF] Sex Coach Sits in on my First Anal Session

I know a few people requested it so I’ll give a description of everyone in the stories!

Michelle is 5’4”, with longer dirty blonde hair, blue eyes, some freckles, on the curvy side, 34D tits, nice ass, and a shaved pussy.

My bf is 6’1”, curly brown hair, green eyes, tan, lean athletic build, and a 7 inch cock.

I’m 5’5”, longer brown hair, brown eyes, tan, more petite side, super perky 34C tits, a round ass (probably my best feature), and a shaved pussy.

So my boyfriend always had an obsession with my asshole. He would always ask me if he could eat my ass and I just never really wanted it so I would decline. He would fairly frequently talk about anal but I just really wasn’t feeling it. One day we were in my basement fucking and while I was in doggy he kept asking me if he could slip a finger in my ass. Eventually I succumbed and out of sheer curiosity, agreed.

I felt him drool onto my asshole and slip his middle finger all the way knuckle deep into my ass. I winced at the feeling of it and he kept fucking me before excitedly telling me he could feel my dick with his finger. He asked me if it felt good and I said it didn’t feel bad. But in all honesty it did a little bit. After a little while he pulled it out and that was kinda it for anal for a while.

Then one day we gave Michelle a ride home from school. As she was walking with us to the car she starts talking about how she finally had anal and it was amazing. After a lengthy conversation we stopped outside her house and she had managed to convince me to try anal. The kicker of course was that she would be there to make sure everything went smoothly.

It also just so happened my family was heading out of town that Friday and wouldn’t be back until Sunday. So we all agreed to do it that Friday night and started planning. Friday rolled around and we were all excited to see how the night was going to go. Once school let out my bf drove me home with Michelle before he went back to his place to meet us later. First thing was first, Michelle and I got in my car and drove to the closest CVS to get wine before, knowing the whole night would go easier with a few drinks in our system.

Next, we set up in my bathroom with a razor. I had never really been able to shave perfectly around my ass and so after a quick shower I laid a towel on the ground, went face down ass up, and spread my cheeks. Rachel went at it with the razor and after a few minutes my ass was smooth and clean shaven. Next was time for me to clean, I’ll spare the details but she helped me with an enema kit she had got for me. After finishing that up I hopped back in the shower and once I was done, started to get ready for the night that laid ahead of us.

After lotioning up and putting on makeup, I slipped into some black lingerie that Michelle had lent me for the night. My bf arrived shortly after and I opened the door to him holding nothing but a bottle of lube and before he instantly lit up seeing how I looked. He came in and we all went straight to the kitchen, grabbed our wine, and went downstairs. We went back to our usual spot and just chatted casually as we drank until we all got hornier and hornier. Eventually my bf and I started making out as Michelle just watched from the sidelines. My bf pulled the lingerie off of me instantly and slipped out of all of his clothes at the same time.

He got behind me and started eating my pussy from the back as he groped me and felt me up. After a few minutes of him sucking and licking my clit I came hard and felt him slide up to my asshole where he started sliding his tongue around and pressing it as hard as he could against my asshole. It felt way better than I imagined and after a little while he stuck his fingers into my pussy and started going at it as he ate my ass.

After cumming for the second time and actually squirting he pulled back and grabbed the lube. First he put some against my asshole and then his finger. He massaged it in before sliding his pointer finger all the way in. I moaned and after a minute or two of him slowly going in and out he added his middle finger. He kept this process up until he had three fingers in and then I told him I wanted to suck him. I jumped onto my back on the bed and draped my head over the side before my bf just started thrusting in and out as fast as he could. I felt my throat pop open and then couldn’t stop him as saliva started oozing out of my mouth all over my face.

Michelle finally cut in and said he should fuck my ass and we all agreed. We all drank a little more and I went facedown ass up as my bf applied lube to his cock and my ass. He slipped into my pussy and have a few pumps before slipping out and just jumping balls deep into my ass in one fluid motion. I let out a gasp but it didn’t even hurt. He started to pump in and out slowly and it honestly felt amazing. Like I was more full than usual. As he started picking up a little more speed Michelle went our if the room to use the bathroom. We both looked up when we heard her enter and saw her completely naked, holding her mostly empty bottle of wine. We were both looking at her and she asked us if her being naked was fine with us. We pointed out the fact that my bf was now balls deep in my ass and that should show we really didn’t care.

We got back to it and my bf was really picking up the pace now, grabbing my shoulders and slamming me onto his cock. At this point I was just gripping his arms trying to hold on for my life. I looked over at Michelle and she’s sitting on the couch with her legs spread, up next to her as she rubbed her pussy softly and groped herself with her free hand. I looked over and told her she wasn’t doing enough coaching and she responded saying she was too horny and it was too hot to coach us. So we told her to just direct us to do what she wanted to see. She continued to play with herself and just started to tell us different positions she wanted us in. So she had my bf lay down on his back across on the bed right in front of her and had me get on top and start riding. I looked over my shoulder and saw her biting her lip as she watched my bf slide in and out of my asshole as my ass bounced around. At this point she was fingering herself and was obviously getting into it.

After a few minutes I turned back to Michelle again and asked her what she wanted to cum to. She said some hard doggy would be perfect. So my bf and I assumed the position and after lubing up a little more, started going at it. It didn’t take long until we heard moaning from Michelle as she came to an orgasm. My bf continued pounding me and at this point was going all out. He grabbed me by both biceps and held me suspended in the air as I arched my back and he pounded. As he was going at it I started feeling it build up and so I moaned for him to keep going harder and faster. At that point I couldn’t imagine him going any harder and I was practically screaming that I was cumming. After I finally finished my bf dropped me onto the bed, put his hands on either side of my head and continued to ram himself in.

I kept moaning and felt the warmth of him pumping a load into my asshole. He finally stopped, pulled out, spun me around on the bed, and shoved himself into my mouth. Being drunk and dick-drunk I just started swirling my tongue around his cock and sucking it clean of his cum before he pulled out and laid down next to me on the bed. We all went to the bathroom and chatted as my bf and I cleaned each other up in the shower while Michelle watched. As we were talking we decided to have another lesson as soon as possible and that we would all drink for that one too.

Source: reddit.com/r/gonewildstories/comments/cvddcy/fmf_sex_coach_sits_in_on_my_first_anal_session