slut-problems: “How about tonight?” he asked me with hope in…

slut-problems:

“How about tonight?” he asked me with hope in his eyes and I wanted to give him what he wanted, but I was scared. I’d never done anal before and he knew it, but he had begged me for months and I had promised that I would do it eventually, it’s just that I’d never given in. 

“Please?” he added and his puppy dog eyes stared up at me. I couldn’t resist him forever. I knew it.

“Okay. Tonight,” I heard myself say and as soon as I’d said it I wanted to take it back, but I knew I couldn’t fuck with him like that. He’d been waiting three years now, since we had first started dating and I wanted to give it to him. My virgin ass wasn’t going to be virgin for much longer. 

“YES!” he said and he did a fist pump into the air and smiled widely. 

That night, in the privacy of our bedroom we made out on the bed, naked. I loved him so much and I was both excited and scared about having anal sex with him for the first time. There was a feeling of excitement and fear in the air as we kissed, our bodies tangled together in passion. 

“Don’t be scared. I’ll be gentle I promise,” he told me. 

“I know,” I told him. “Just start by fucking me in the pussy first,” I said, buying myself some more time. His cock entered me slowly and it felt great. The feelings of pleasure built up inside of me and he kissed me deeply as I began to cum, my first orgasm of the night. 

“It’s time,” he said, reaching down and putting a finger in my ass. It felt good, but I wasn’t so sure a cock would even fit down there! As if sensing my fear my boyfriend whispered in my ear, “Don’t worry, it’ll fit.” He slid off of me and turned me onto my side as he lubed up his cock and even added a bit of lube to my asshole. His cock looked extremely hard as he anticipated shoving it into my asshole. He worked a finger in and out of my ass, getting it ready. To my surprise my asshole seemed to loosen up and he added another finger. It felt pretty good, and I was surprised that I’d never tried any of this before. I was twenty-four years old and just trying anal. 

“Here,” he said to me and he pushed the head of his cock into my asshole. 

“OW! OW! OW!” I screamed. “Take it out! TAKE IT OUT!” I screamed, but he didn’t take it out. Instead he held it in my ass. 

“Relax, honey. Unclench your ass and it won’t hurt so badly!” he coached me. 

“Okay,” I said, a lone tear falling down my cheek. I wasn’t sure I could handle this anal sex shit. It hurt a lot more than I thought it would but as he slowly pushed his cock deeper inside of me and I continued to relax my butt I could tell that there was pleasure to be had as well as pain. My fingers moved to my clit, and I rubbed my pussy as he moved in and out of my asshole with his thick cock. 

“I’m doing it!” I exclaimed with a smile. I looked back at him and our eyes met conspiratorially, like we were doing something naughty together and getting away with it. I was actually trying anal for the fist time and I was having fun! 

“So how does it feel?” he asked me, genuinely curious about my experience. 

“It feels good, but also weird. I feel like I have to shit out your cock or something,” I tried to explain. “But it feels good, too. I think I can cum like this if I rub my pussy!” 

“Maybe you should add this to your pussy,” he said grabbing my pink dildo and handing it to me. “Try it and see what you think!” I figured it couldn’t hurt and so I lubed up the dildo and worked it into my pussy. Now his cock was fucking my asshole and I was working the dildo in and out of my pussy with my hand. Now it was feeling really good and I came hard, screaming loudly as I did. I could feel the cold chills from my asshole working all the way up my back and to the nape of my neck. I was cumming, and I could feel the orgasm in my asshole and my pussy at the same time! I loved the way it felt and I knew that I had waited way too long to try anal. Yes, it hurt a bit, but after a while, after I relaxed it felt amazing, and after adding the dildo I realized there was limitless potential! 

“Damn,” he said. “I’m going to cum! It feels so good. So fucking tight. I love anal,” he told me as then I listened to him moan as his cock came hard inside of my asshole. I worked the dildo in my pussy and had another small orgasm on his cock before he pulled it out of my ass. 

“I did it!” I said excitedly. 

“You sure did! Now come on, let’s go clean up in the shower,” he winked at me. 

“Okay!” I said, pulling the pink dildo from my pussy. We got up and headed to the bathroom. He turned the water on and as it was getting hot he embraced me and kissed me deeply. 

“I’m proud of you. Thank you for giving anal a chance. Did you like it?” he asked. 

“I loved it!” I exclaimed. “I’m sorry it took me so long to try. I was just scared.” 

“It’s okay. At least you tried it now. Now maybe we can do anal every once in a while.” 

“Can we try it again in the shower? Should I grab my dildo?” I asked him. 

“We can if you want! It looks like I’ve created an anal monster,” he said, laughing. 

“Maybe you did!” I screamed over my shoulder as I ran to the bed to collect the lube and my pink dildo for round two.