My first fucking [MM]

I would usually get naked when giving James head. I mentioned before it turned me on when he would talk dirty to me when I gave him head, but even more so when I would be naked and going down on his cock and he would reach down and spank my bare ass or begin to play with my ass. Eventually, he began to play with my asshole, fingering me and making me shiver as he pushed into me up to his first knuckle and pressing into my prostate.

The fact that James was playing with my ass as I gave him head made me wonder if he wanted to fuck me, but he never brought it up. Still, I was fascinated with the idea and wanted to give him the opportunity. I wanted to see if I could take it. So I went to the local sex shop to see if I could find a toy I could use on my ass. I found it in a black, vibrating butt plug that was about 1.5″ wide at its base. I wasn’t sure if I could take it, but it seemed like a good start. While I was at the store, I also noticed a super cute, skimpy, leopard print bikini that I was so drawn to that I had to buy it as well.

I was excited to try out my new toy when I got home. I locked myself in my bedroom, stripped naked, and lubed up my new plug to begin playing with it in my ass. It took a little bit to push it all the way into my ass, but when I did get it all the way in past the 1.5″ width at its base, it was exquisite. I turned on the vibration and couldn’t believe how good it felt having my ass filled. As I played with it more, I found what I liked best was either being on my back and pushing the plug into myself or squatting down on it and having it push into my ass. The thing that surprised me the most was how when I pushed the plug against my prostate, it would make my cock get so hard from being filled like that.

I also found I loved my little skimpy leopard print bikini. I’d never dressed up as a girl before and it was thrilling to try. I began looking up videos online about how to do makeup and soon bought my own makeup at the local drugstore so I could try wearing it myself. I found I could make myself look pretty cute as a girl soon enough.

I had an upcoming weekend where my roommate was going to be out of town and James and I were going to hang out, so I felt like I had an opportunity. I never had a lot of body hair, but I shaved off what hair I had to make myself nice and smooth. I tied my long, curly, brown hair into a pony tail. I did my makeup nice and effeminate. I lubed up my butt plug and slid it into my ass, nice and snug, before finally slipping into my leopard print bikini. I was ready!

When James knocked at my apartment door, I opened it standing behind the door, saying, “I have a surprise for you.” When I stepped out from behind the door, he was initially startled at my appearance, but quickly smiled broadly.

“Look at you,” he said. “I think someone wants to play.”

“Of course, I want to play,” I replied. “Do you like how I look for you?”

“I do,” he said. “Come here,” he pulled me toward him and began to push me to my knees. He undid his pants and pulled his hard cock out for me and pushed it toward my face, I took his cock into my mouth and began to suck it as he pushed my head down on it. “I want you to suck my balls with no hands,” he told me.

I ducked my head underneath his cock and began to lick and suck on his balls, his cock resting on my head as he reached down to play with my ass. As he did, he saw my butt plug deep in my ass and exclaimed, “Well, look at this. Aren’t you the dirty little slut?”

He pulled me up from sucking his balls and led me back into my bedroom, pushing me down on to my bed. “Lay back,” he told me and as I laid on to my back, he lifted my legs up and pulled the bottom of my panties down. I closed my eyes as I felt him begin to slowly work the plug out of my ass, knowing this was happening now. I had left a tube of lubricant on my night stand and I could hear him begin to use it on his cock before he pressed his hard cock against my ass, my legs up over his shoulders. I gasped as his fat cock pushed into my ass, entering me, not believing he was inside me now and how good it felt. He pushed his body against my uplifted legs, pushing his cock further and further inside me until he was fully penetrating my ass and it felt so unbelievably good, I was seeing fireworks in my closed eyes. I think I heard myself yelp! He leaned down nest to my ear as he began to fuck me and said, “I love that I can fuck a slut like you without worrying about you getting pregnant.” I knew then that he was fucking me bareback and couldn’t wait to be filled with his cum.

He was fucking me good and deep now in a nice rhythm, my legs up over his shoulders and I couldn’t believe how good it felt having his cock sliding in and out of my ass. I heard my own voice asking him, “Oh yes, fuck me harder!” Was that really me? I couldn’t believe what I was saying, but I couldn’t control myself. “Yes, fuck my ass! Fuck me harder!” I was begging him. Plus I realized my own cock was rock hard as he was fucking me.

Before I knew it, he was driving deep in my ass and began to stiffen up. “I’m cumming,” he told me, slapping my ass as he did and I could feel him as he drove deep and emptied his load deep into my ass. It was amazing as I felt it, then felt his cock begin to soften inside me as he slowly withdrew. He went to the bathroom to clean up and as he did, I reached down to touch my own hard cock. I came into my hand almost immediately when I did, I was so turned on. I quickly licked the cum out of my palm, realizing now I had cum in my belly and my ass at the same time. I felt like a little fuck toy and I loved it.

Source: reddit.com/r/gonewildstories/comments/c63tev/my_first_fucking_mm