Five Masks of Sin

by Kelli Callahan

  He slid past the spot where my hymen once was and started stretching me even more. He had several inches inside me and he was able to get a little bit of a rhythm going. He kept pushing himself deeper with every few strokes, keeping me on the edge of pain and pleasure. His thumb on my clitoris had started to really get me going again though, and even with the pain, I was feeling the pressure building towards another orgasm. That seemed to be making me wetter as well, which made him able to slide into me a little easier. The fact that his cock was teasing the muscles inside my pussy while my clitoris was stimulated definitely added to the effect. After several minutes of taking half of his cock, I was on fire again, boiling with pleasure that demanded a release. My head rolled back against the mattress and I started to moan.

  “Oh god, I’m gonna cum again!” I squeezed my fists and then my hands opened fast when the feeling roared to life.

  “Yeah, cum for me, baby.” He smiled. “Show me how much you love my cock.”

  Hearing that sent my orgasm over the edge. It was filthy, commanding, and made me tingle. My orgasm sent the spasms through my body again and my pussy started to massage his length. He took that opportunity to go deeper, guided by the pleasure that he had created. He picked up the pace and the pain evaporated in my bliss. Before my orgasm started to subside, I felt his abdomen against my pelvis and realized he was all the way in. He started moving his hips, driving his cock from the entrance of my pussy to the deepest point it could go, and then I felt something I had never felt before. My eyes opened wide when he pushed against my g-spot for the first time. It instantly started building the pressure inside me again.

  “Keep doing that! Please!” I bit down on my lip and moaned louder.

  “I’m going to fuck you until we both explode now.” He shifted his weight and the thrusts got faster.

  It was an incredible feeling. His hips glided up and down my thighs so fast that the friction made them tingle. My pussy was no longer hurting. It was locked in the bliss of being really fucked for the first time. My g-spot was like a magnet for his cock, begging for it, and then screaming for more the instant he pulled away. Every thrust sent a pulse of absolute bliss through me. The pressure was uncontrollable like a wildfire raging inside me. I knew I was close again. He started thrusting into me so fast that his hips were like a jackhammer when he came crashing down into my body. I felt his cock get harder, pulsating with the same desire I felt. It started to throb and his moans turned into grunts. His head fell back against his shoulders and he gave me a thrust so hard that it shifted me on the bed.

  “I’m gonna explode!” He roared and his grunt shifted to a growl.

  “Oh god, me too!” I nodded quickly.

  His pleasure was unleashed inside me. He started to thrust again as I felt the condom ballooning with his seed. I could feel the cum surging through his shaft before it erupted inside me. It was enough to send me spiraling towards another orgasm and I felt my pussy massaging his dick, milking him as the volcanic geyser threatened to burst the condom. He kept thrusting, even after he was spent, until the last remnant of my orgasm had faded. I was in so much bliss that my body went weak. He pulled his cock free, dropped the condom in the trash can beside the bed, and then fell down beside me. I watched the intensity in his eyes start to fade as the high of our lovemaking started to wear off.

  “That was really good.” I let out a long exhale. “I’ve never smoked before, but I feel like I need a cigarette.”

  “I gave up that demon a long time ago and this is the only time I feel the need as well.” He chuckled and rolled over towards me. “Luckily, I usually just go for round two and kill the craving with something a lot healthier.”

  “Round two?” I looked at him with my eyes wide. “I don’t think I can take anymore right now.”

  “It’s okay.” He smiled and let his fingers trace my body. “We’ve got all night.”

  My initiation into the world of sex had begun. We made love several times over the course of the night, napping between our sessions. I wasn’t even sure how many times he was inside me before it was done, but I woke up with my pussy rather sore and my body aching. I had worked muscles I didn’t even know existed. He ordered room service shortly before noon and I realized I was famished once I bit down on a piece of fruit. We devoured everything in sight before we stopped. I couldn’t remember simply needing food as fuel before that moment, but I felt like I was refilling a gas tank that had been running on empty for a while.

  “So, was this just a one night stand for you?” I leaned against my chair and looked over at him.

  “Do you want it to be a one night stand?” He raised his eyebrows and tilted his head.

  “I’m not sure.” I swallowed hard and looked down at the table. “I have nothing to compare it to.”

  “I’ll admit, I came to the World Ball with the hopes of meeting someone like you. I was honored to be your first, but I don’t want you to feel obligated to stay with me just because I was.” He leaned against the table. “You’re very special, Lyric, but you are doing yourself a disservice if you don’t see what else is out there.”

  “I didn’t come here to sleep with random guys.” I lifted my head and exhaled sharply. “I hoped I would meet someone, but I didn’t expect to end up in bed with the first guy I met.”

  “What we had was magical.” He nodded and reached over to take my hand. “I just don’t think you fully know what you want yet.”

  “You’re right.” I looked down at his hand and nodded. “I would probably fall in love with you and never look at anyone else, just because it was the fantasy I created in my head, but I would always be curious.”

  “I want you to find another guy tonight and I want you to leave with them.” He traced my knuckles with his fingers.

  “Seriously?” My eyes opened wide in surprise.

  “Yes.” He nodded again. “I want you to embrace what you have discovered. I’m not a jealous man, nor am I complicated. What we did doesn’t have to be complicated. Where it goes from here doesn’t have to be complicated.”

  “Thank you.” I sighed and nodded. “I really appreciate that.”

  I felt like I had definitely chosen the right guy to be my first, but what he said was right. I had been awakened in a way I didn’t completely understand. The years of sexual repression were blossoming into something that I had to explore. I returned to my room and put on my second dress. It wasn’t as lavish as what I wore the first night, but it transformed me into the masquerade version of a red fox, complete with a tail that was stitched into the back. I had no idea what I was going to do if I stayed the full seven days, because I was only able to afford three dresses. I had more confidence when I ventured out onto the dance floor the second night. I saw Maximo at the bar drinking, and it seemed like he was watching me. I looked around for someone to dance with and then I felt someone take my hand.

  “Care to join me?” The man smiled and took a step back, pulling me towards the dance floor. “Foxes should stick together.”

  The man that had taken my hand was older than Maximo. He had a silver beard underneath a mask similar to mine, except the fur along the top had a gray hue. It blended into his hair, which was a similar shade. Even though he was older, he was stout and once I stepped towards him, he twirled me with ease. I wasn’t sure exactly how old he was, but he looked like he had at least twenty years on me. He wasn’t someone I would have normally danced with, but his moves were impressive. I took one glance towards the bar and saw Maximo giving me a thumbs up.

  Chapter 5: Simon

  “Yeah, call me Daddy, you naughty little girl.” I raised my hand and brought it down on the exposed ass across my knee.

  “I’m sorry, Daddy! Please don’t spank me!” She pouted and looked over her shoulder.

  “Oh, you’re getting a spanking, all right.” I lifted my hand and brought it down again. “Then you’re going to show me how sorry you really are.”

  The girl across my knee was a
young submissive that I met online. She had asked for the fantasy we were in the middle of and it was one I was enjoying—at least the spanking part. She was the perfect example of what my sex life had become once I hit thirty-five and started going gray. Most of the women my age were married with kids, and those that weren’t seemed intent on reliving their youth with younger men. I had pretty much given up on finding a serious relationship and after five years of meeting women online, I had learned that there were a lot of women looking for someone like me. The only problem was that they weren’t looking for anything serious. They were just looking for someone that could help them embrace their fantasy.

  “Don’t put in there, Daddy.” She looked up at me as I mounted her once the spanking was done.

  “Oh, it’s going in there. You better believe it.” I lifted her legs and growled.

  This is the part I don’t like.

  I loved sex. Sex was glorious. It was the sole reason I looked for beautiful young women that needed their Daddy issues addressed by someone like me. It was fine when the foreplay was in full swing. It was fine when they were over my knee for a spanking—that part I liked a lot. I just didn’t like having them call me Daddy while I was inside them. It just didn’t push any of my buttons. I liked to hear them scream my name while they looked in my eyes. I wanted them to be with me because they liked me, not the fantasy they craved. A woman that liked both sides would have been perfect. I would have even skipped the spanking to have sex that wasn’t grounded in fantasy.

  And we’re done.

  AFTER MY ENTERTAINMENT was over for the evening, I sat alone in my living room, sipping a glass of whiskey and enjoying a fine cigar. I liked having the freedom to do what I wanted inside my house, although I would have been fine huddling outside in the cold to smoke if it meant there was someone warm waiting inside. My divorce had been a brutal blow to my self-confidence and it took several years for me to find it again. I wasn’t ready to give up on life quite yet, but it didn’t seem like I was ever going to find someone that wanted more than a fantasy. I could have probably lived with that if my bed wasn’t a revolving door. It was funny in a way. There were lots of married guys my age that would killed for my life, and I would have killed to trade places with them.

  “Hmm. The World Ball.” I tapped my tablet and loaded up the email notice I had received about the annual event.

  I passed on this last year, but I wonder if I should actually consider going.

  I knew a few people that had attended. One of my best friends met his wife at the World Ball. Of course, that was when he was a young man. I decided that it couldn’t hurt to sign up. I wasn’t even sure if they would accept me. As far as I knew, they catered to the younger crowd rather than someone my age. I put my information in the form, uploaded my most recent picture from work, and leaned back in my chair. I was still horny, despite getting off inside the girl that had kept me entertained, so I loaded up some porn and started stroking my cock. Some guys went online to find the filthiest porn imaginable, and a lot of the stuff they searched for happened in my bedroom. I just wanted something normal. I finally found something that would keep my interest and started stroking a little faster.

  This is the kind of woman I need to find—someone that doesn’t mind a little roughness, but still wants the man they’re fucking.

  THE FIRST NIGHT OF the World Ball was a bust. I had a few offers from young girls, but of course they called me Daddy before asking if I was going to give them my pin. As tempting as it was, I just didn’t want that. I could have that anytime. The girl that really got my attention was dancing with someone else. She was drop-dead gorgeous and dressed like a mermaid. It would have complimented my Poseidon outfit nicely, but she was already dancing with a rather attractive man, who was much younger than me and dressed as a phoenix. It pained me to go back to my room alone, and pained me even more when I saw her leave with him. The second night was shaping up like the first, and I was almost ready to call it quits when I saw her walk close to the dance floor wearing another outfit that complimented mine—a red fox.

  This has to mean something right? What are the odds?

  I had seriously considered dying my hair and shaving off my gray beard before the second night, just to see if I could dance with someone that wasn’t into that sort of thing. I decided against it since I already had a silver fox outfit for the second night, and it really wouldn’t look right if I did. I also didn’t want to give up what I had back home. It would take a while to get my look back and I really didn’t think I would have the kind of success I had been having if I gave up the one asset that was getting me laid. I had tried it once and the drought lasted for several months. I was planning to stay all seven days and I would be ready to take anyone home that I could find, even if it was just a fantasy for them after a few days of shunning the ones that showed interest.

  “I saw you last night.” I smiled and twirled the red fox in my arms. “You left with someone else before I could introduce myself.”

  “I’m Lyric.” She spun back towards me and I dipped her towards the floor.

  “Simon.” I pulled her back to her feet. “I didn’t expect to see another fox here tonight, especially one as beautiful as you.”

  “I figured my outfit was dorky enough that I would be the only one.” She laughed and stepped back with the beat of the music.

  “I don’t think it’s dorky at all.” I put my hands on her hips. “I don’t think anything would look dorky around those curves.”

  “I might have to wear it again if I stay longer than three nights. I don’t have enough outfits to get through the entire dance.” She smiled and inhaled sharply when I brought her close to my chest.

  “There are plenty of stores around here that you can buy what you need. Maybe I can take you tomorrow?” I leaned forward and whispered into her ear. “I’ll even pay for it if you’ll model them for me.”

  “I’m not looking for a sugar daddy.” She leaned back and shook her head. “I’m just here to have some fun.”

  Wow, that is actually a promising start.

  “You’re not dancing with me because you have repressed daddy issues that need to be addressed?” I tilted my head and looked down at her.

  “I’m dancing with you because you took me by the hand and pulled me out onto the dance floor.” She laughed and pushed away. “No repressed issues here. My father is a very nice man.”

  Okay, very promising.

  “Don’t leave.” I reached out for her again. “I didn’t mean to offend you.”

  “I’m not offended, I’m just not looking for an older man that wants me to call him Daddy.” She shrugged her shoulders. “I’m sure there are plenty of women here that are into that sort of thing.”

  “Which is precisely why I’m dancing with you instead of the ones that approached me.” I took a step closer. “Come on, keep dancing with me. I like you.”

  I like you a lot.

  I knew Lyric was too young for me. There was no way she was going to settle down with someone like me. It was the opposite of what I was after, but I felt drawn to her. I looked over her shoulder as she stepped back into my embrace and saw the guy she was with the night before. He had taken off his mask, so I couldn’t tell what his costume was supposed to be, but he was watching us. He made eye contact and nodded to me, but he didn’t appear to mind that I was holding the woman he left with the night before. Lyric danced with me for almost an hour before we finally had to sit down from pure exhaustion—at least on my end. My stamina on the dance floor wasn’t what it once was.

  “You’re going to offer me your pin, aren’t you?” She grabbed a glass of water and started drinking it.

  “I’m seriously considering it.” I nodded in confirmation.

  “None of the stuff you mentioned, right?” She tilted her head and narrowed her eyes. “I’m interested, but not in some weird fantasy.”

  “I might spank you, but the only name I want to hear is Simon—or maybe oh
god. That works too.” I smiled and reached for her hand.

  “I don’t know.” Her lips twisted with a look of concern. “I’ve never been spanked before.”

  “You might like it. It’s excellent foreplay.” I grinned and squeezed her hand.

  “Then maybe I should spank you.” She tilted her head in the opposite direction and bit down on her lip.

  “Take my pin and you can do whatever you want.” I pulled my hand away and reached for my lapel.

  “Okay.” She nodded and removed her pin. “Let’s go.”

  Oh you’re definitely getting spanked, you little fox. There’s nothing better than a woman that has never submitted learning to enjoy it.

  Lyric was exactly what I needed after the run I had with women I met online. I wasn’t dominant enough to call myself a true Dom. I enjoyed having a woman submit and spanking their ass was fun, but I didn’t take it far enough for those that were really submissive. I had tried it a few times and it just wasn’t my cup of tea. I asked a couple of women into real bondage to send me videos of the stuff they wanted before we agreed to meet and that sent me retreating back to the young ones who wanted to call me Daddy. Lyric and I held hands until we got to the elevators and then I turned her towards me for a kiss.

  Chapter 6: Lyric

  I never imagined that the second guy to take me to bed would be a sexy older man with silver hair. He wasn’t even the kind of guy I fantasized about. I was fairly certain a lot of girls would love to call him Daddy, even if that wasn’t a fantasy I had. What drew me to him most was the fact I knew he was experienced. After being with Maximo, I was scared to leave with someone else, even though I did want to explore my budding sexuality. Simon just seemed so trustworthy and authentic. The fact he wasn’t looking for someone younger for some weird fantasy eased my concerns and made me forget the age difference between us.