Five Masks of Sin

by Kelli Callahan

  “Before we go inside your room...” I paused at the door and turned to face him. “I’m open to trying new things, but if I ask you stop, you have to give me your word that you will.”

  “We can set up a safe word if it will make you feel better.” He took my hand.

  “My safe word is stop.” I pursed my lips and nodded. “I’m serious about that.”

  “That’s good enough for me.” He pushed his key card into the door.

  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.

  “Now you’re going to find out what it really feels like to be fucked.” He held onto me and started to stand.

  “What the hell?” My eyes opened wide and I dug my nails into his back.

  Simon put a forearm under the back of each knee and held my ass with his hands. They were so wide that they easily gripped my cheeks. I was suspended in the air, practically floating. I kept my nailed latched onto his shoulders and he started to lift me. He sent me in the air and then brought me crashing down. Each time, it felt like my pussy as being impaled on his enormous cock. I surrendered every ounce of control I had. I no longer wanted to be anywhere but in his arms. He bounced me on his cock until I was screaming, begging for the sweet release an orgasm would bring. I finally felt the pressure start to let go and then the most powerful orgasm of my life devoured my sanity.

  “Fuck! Oh god! Simon! I’m cumming!” My words came out between screams—not that I had to tell him I was orgasming, he clearly felt i
t.

  “This is so fucking good.” His cock throbbed harder than it had up to that point.

  He started to ejaculate into the condom as I was yanked up and down his shaft like a rag doll. One orgasm wasn’t enough. My body was boiling with desires that couldn’t be quenched with one trip to paradise. I orgasmed again and again, each one chaining onto the last like it was one continuous string of ecstasy. He filled the condom with every drop of his seed and I didn’t stop cumming until he was spent. I was so weak I couldn’t move. He could have done anything with me at that moment and I wouldn’t have been able to fight. He slowly withdrew his cock from my pussy and carried me to the bedroom. I was so tired that the bed felt like a cloud. He climbed in next to me and our sweat melded together as our heartbeats started to slow down. It took almost ten minutes for me to really catch my breath.

  “I’ll call you whatever you want after that.” I leaned closed and purred in his ear. “And if you want to spank me, just do it—anytime.”

  “Does that mean we might do this again?” He looked over at me.

  “The night is still young...” I forced a smile, even though it took more energy than I had to form it.

  IT WAS TOUGH TO LEAVE Simon when morning came. My heart felt like it was torn in two different directions. Maximo was still fresh on my mind and he was the one that told me to find another guy. My time with Simon was incredible. When I finally said goodbye, with no promise of what the future held, I felt hollow. I saw a certain sadness in Simon’s eyes. I was the one that came to the World Ball planning to find someone special, yet I had walked away from two very incredible men. I spent some time in my room and then decided to venture out for food. When I got to the lobby, I was surprised to see Maximo waiting near the area for Uber services. I wasn’t sure what I would say to him and I considered hiding, but he saw me before I had a chance.

  “Did you have fun last night?” Maximo walked over and smiled.

  “I—I guess I did.” I nodded and stared at the floor. “Simon was really nice.”

  “He seemed to be very interested in you.” Maximo nodded and put his hand on my shoulder. “You have nothing to be ashamed of. If you enjoyed your time with him, be proud of it.”

  “I thought time with another guy would just make me miss you after what we did. I did—but it wasn’t what I expected to feel.” I sighed and leaned against his hand. “I did what you asked and now I don’t know what I want.”

  “I thought you might feel that way.” He reached out with his other hand and brushed a strand of hair from my face. “I’m going to arrange something special for you tonight. Are you up for it?”

  “Maybe.” I looked at him with concern on my face. “What do you have in mind?”

  “It’s a surprise.” He smiled and exhaled sharply. “Just keep an open mind.”

  “I’ll try.” I twisted my lip into a half-smile.

  As long as you don’t tell me to leave with someone else. My sexual awakening is complicated enough as it is.

  Chapter 7: Lenny

  “What is this shit?” I looked at my computer and then turned towards my brother. “What the fuck is the World Ball?”

  “Oh.” He chuckled and nodded. “I signed up for that a while back, but that was before I met Nadia.”

  “So, three weeks ago?” I glared at him and shook my head. “How the hell can you marry someone you’ve known for less than a month?”

  “It’s true love, brother.” He shrugged and adjusted his tie. “You’ll know it when the snake bites you.”

  “Like hell.” I glared at him. “You’re marrying some stuck up city girl that gets splinters when she crawls out of bed in the morning! Do you really think she’s going to live her life in the fucking mountains?”

  “She says she’s willing to do anything as long as we are together. I believe her.” He walked over to the mirror. “You need to get your suit on. We’re going to be late.”

  “Yeah.” I grumbled as I stood and reached for my dress slacks.

  “Since I won’t be going to the World Ball, you should go. The invitation is transferable as long as you pass the background check. You might even meet someone special.” He turned towards me as I stumbled putting on my slacks.

  “I’m fine here. I don’t really dance anyway.” I shook my head back and forth.

  “I’ll transfer the invitation to you, just in case.” He grinned and handed me my shirt.

  I had no intention of going to the World Ball, but a few days later I got the notification that the invitation had been transferred. When I clicked on the link, it said that based on my income level, I was selected to not only get a free room in New York, but they would also pay for a plane ticket. Apparently living off the land and keeping most of my money under my mattress had given them the idea I was as poor as the dirt my cabin was built on. I might not have had much interest in the World Ball, but I had always wanted to see New York. I had never even been outside the state of Kentucky, and the patriot in me wanted to see the Statue of Liberty at least once before I died.

  I guess I’m going to New York.

  “SIR, THIS IS A MASQUERADE. You’re supposed to wear a mask.” The man at the door tilted his head as he stared me down.

  “A mask?” I grunted. “I don’t have a mask.”

  “You went to the trouble of creating this... lumberjack look and you didn’t even get a mask?” He tilted is head in the other direction.

  “Ugh, fine.” I pulled up my flannel shirt and ripped off part of my white undershirt. “I’ll make a mask.”

  Lumberjack look? This is what I wear every day...

  I stabbed a couple of eye holes in the strip of fabric and tied it around my head. The man at the door looked a little flabbergasted, but he allowed me to enter the ballroom. The music was too loud, the people were absolutely hideous, and the only thing that drew my attention was the bar. I carved my way through the crowd until I had a stool and ripped the rag off my head. I asked the bartender for a beer and guzzled it once he brought one over. I turned on my stool and stared at the crowd, which seemed to be very involved in their dancing. I definitely wasn’t going to be joining them. I had managed to avoid the ballroom for two straight days, but after I found out the event was going to last a week, I figured I should at least see what they were paying for me to attend.

  “Quite a sight, isn’t it?” A man several seats over turned to me.

  “What are you supposed to be? A peacock?” I raised my eyebrows when I turned my head towards him.

  “Something like that.” He chuckled. “A bird of paradise.”

  “It looks like a peacock to me.” I chuckled and sipped my beer.

  “Your accent, you’re from the south?” The man lifted his eyebrows and scanned my attire with a quick look.

  “Kentucky.” I nodded. “What about you?”

  “Italy.” He smiled. “My name’s Maximo.”

  “Lenny.” I tipped the top of my beer in his direction. “Nice to meet you.”

  “Lenny? Is that short for Leonardo?” He sipped his drink and smirked.

  “No, it’s just Lenny.” I glared at him slightly. “My parents weren’t fancy enough to add an O.”

  “I see.” He nodded. “So, I haven’t seen you in here before tonight. Did you get here late?”

  “No.” I shook my head back and forth. “I was sightseeing. I ran out of shit I wanted to see, so I figured I’d check this place out.”

  “Interesting.” He tilted his head. “You came all the way here for the World Ball and haven’t even bothered to come?”

  “I didn’t come for the World Ball.” I snorted and took a sip of my beer. “My brother gave me his invitation. I just came because it was free.”

  I noticed Maximo’s eyes shift towards the dance floor and I followed his gaze. His eyes were locked on the most beautiful sight I had ever seen. A woman stepped to the edge of the crowd wearing a long black dress and a black feathered mask. I had no idea what she was supposed to be, bu
t she reminded me of a crow. I had never seen a woman like that back in Kentucky. She practically took my breath away. She stood out like a beacon in the crowd and when she walked, it was like the world froze on her and every spotlight was meant to cast a reflective glow on her gorgeous form.

  “That’s Lyric.” Maximo noticed my stare and pointed.

  “Lyric? She’s a whole fucking song.” I closed my mouth once I realized my jaw was literally drooping.

  “She’s that and a whole lot more.” Maximo nodded and smiled. “Would you like to dance with her?”

  “I—don’t really dance.” I shook my head back and forth. “But I don’t think a girl like that wants a guy like me. She looks like your type, though. Why don’t you go dance with her?”

  “I’ve already danced with her and did a little more than that.” He chuckled and smiled. “Maybe you’d like to just skip dancing and join the two of us in my suite.”

  “Hey, I’m not into that.” I shook my head quickly. “I don’t have a problem with guys that like other guys, but I’m not interested.”

  “That’s not what I meant. The only person you’ll have to worry about is her.” He motioned to Lyric.

  “Is this some sort of prostitution thing?” I tilted my head. “I’m not interested in that, either.”

  “It’s definitely not prostitution. I promised her something special and you look like the kind of guy that doesn’t hold anything back. In fact, I thought I wasn’t going to be able to make good on that promise until you walked up.” He moved one seat closer. “Come back to my room with us. It’ll be just the three of us and you can do anything to her that you want as long as you don’t hurt her.”

  “You’re fucking serious.” I blinked and quickly guzzled what was left on my beer.

  “I am.” He nodded quickly.

  “Fuck it. I’m never coming back to New York. I might as well see how you fuckers live at least once while I’m here.” I sat my empty beer bottle on the bar.