Five Masks of Sin (Haremworld)

I was aware that some people used a safe word for kinky sex and hidden fantasies, but I wasn’t ready to try anything like that. I felt like I would need a lot more experience with sex before I was comfortable relying on that sort of cushion. I needed someone that would respect my boundaries and I was glad that Simon was agreeable. I knew that part of the process of getting invited to the World Ball required extensive background checks, so I didn’t fear for my safety, but I was in a new world that made me extremely cautious. We walked into his room and he immediately started kissing my neck from behind. I gasped when I felt his lips, moving against my flesh. They were rougher than Maximo’s were and there was more intensity behind them.

“I can’t wait to get you out of this dress.” He pulled at the straps along the top of my shoulders.

“Don’t rip it. I might have to wear it again.” I sighed as my body succumbed to desire once he started kissing my neck.

“I was serious about buying you more tomorrow.” He slid his finger onto the zipper on the back and started pulling it down.

“I’m not taking your charity. Save that for the girls that like that sort of thing.” I shook my head back and forth.

“Fine, I’ll be gentle with your dress.” He chuckled and started slowly sliding it off of my shoulders.

I wasn’t sure what Simon would look like when his shirt came off. I could tell he was muscular, even more so than Maximo, but I still didn’t know what age would have done to his skin. I was pleasantly surprised to find that while he had silver up top, there were guys my age that would have killed for a body like his. I was also a bit terrified when I saw how large his cock was. It was about the same length as Maximo’s, but it had more girth, especially when it started to get hard. I reached down and stroked it with my hand, feeling it pulsate from my touch. I was afraid of what it would do to me, especially since I wasn’t completely healed from losing my virginity and spending the night when Maximo.

“I wanna be on top.” I leaned forward and kissed his ear.

“Whatever you want.” He walked to the couch and sat down. “You can spend as much time on it as you’d like.”

I unwrapped a condom and unrolled it on his length before I stepped over his legs and put my knees on each side of his hips. He pulled me close for a kiss as I started to descend towards his enormous dick. I felt a little better knowing I could control things. If he wasn’t as gentle as Maximo, he would have definitely hurt me. He reached behind my ass and rubbed my pussy as I got near the glans. I was so wet that I didn’t think I would need much assistance in that department, but when I felt soreness from only a finger sliding inside my pussy, I realized I might need a little stimulation before I tried to take his cock.

“That feels good.” I moaned when his finger went deep and brushed against my g-spot.

“You’re ridiculously tight.” He shook his head as he continued pushing a finger inside me. “This is the tightest pussy I’ve ever felt.”

“Yeah, well—I lost my virginity last night.” I moaned again when his finger went deep inside me.

“Seriously?” He blinked in surprise.

“Yeah.” I nodded. “But don’t worry, I learned to enjoy it quick.”

“You’re sure you want to do this?” He tilted his head and pushed his finger deep again.

“I do.” I nodded quickly. “I’m definitely sure.”

“Okay then.” He pulled his finger away and held his cock as began to lower myself until my wetness was touching his glans.

I felt my pussy stretching as I sank down on his cock. I was so turned on that it didn’t really hurt until a couple of inches went in and the slightly healed skin where my hymen was stretched out to accommodate his girth. It burned for a moment, but I knew from my time with Maximo that it wouldn’t hurt for long. I rose up and sank down again, going further thanks to the lubrication that was already on his dick. Once I had a few more inches inside me, I bounced on it a few times and heard a gasp rush from his lips. I continued sliding on him, slowly, moving up and down when a little more flesh was stretched, until I finally felt him against my g-spot. He wasn’t all the way in, but the friction was enough to heighten my pleasure. I kept moving until I finally had every inch buried inside my pussy. I stayed there for a few seconds to adjust and then started to move up and down his shaft.

“Now, let me show you how it feels to get spanked.” He leaned forward and gave me a hard smack on my ass.

“Oh!” I squirmed when I felt his hand and then bounced on his cock. “Okay, that wasn’t bad.”

“See, I told you you might like it.” He gave me a second on the other side.

“Oh god!” I felt the vibration and with his cock inside me, it heightened the pleasure.

“That’s one name I like to hear.” He spanked me a little harder.

“Yeah, Simon. That feels good!” I gasped when the vibrations made my g-spot hum.

The spanking itself didn’t turn me on, but the way it made me vibrate when his hand landed was enough to make me squirm. Instead of the steady motions I had as I rode his cock, the squirming threw off my rhythm. I thought I would be in control if I was on top, but I quickly realized that he was the one with the real control. All he had to do was give me a stinging smack on my ass and I started bouncing like crazy. Even when my skin started to burn, I didn’t want him to stop. I could feel his cock getting harder and throbbing as he landed the flat side of his palm across my cheeks. I was willing to endure it if it brought that much pleasure to us both. It definitely wasn’t anything like the spankings my friends described—which was a good thing.

“Ride that cock, baby.” He squeezed my hips and gave my ass a break. “You know you love the way it feels inside that tight pussy.”

“You don’t even know!” I threw my head back and started panting.

“But now it’s my turn.” He growled and wrapped an arm around my back.

Simon pulled me against his chest and lifted me slightly. He held me against his body and started thrusting upwards into my pussy. I thought I was going to erupt when I felt his furious thrusts. They were against my g-spot every time he went deep and my body was on fire. I might have had some hesitations in the beginning, but I didn’t have any at all when he really took control. I gave in completely to him. All I wanted was for his hips to keep moving until the pressure that was inside me gave way to bliss. I held onto him, just whispering his name and purring in his ear. I wanted every inch of his cock each time he delivered a powerful thrust. My body started to quiver and shake. I was close—so very close.