First Timers Series: The Collection

by Cummings, Cici

I couldn’t believe all of it was turning me on. I wanted more, despite how much it hurt. I wanted to be his bad girl, the toy that he had no choice but to punish.

  Right as I expected another lashing, he ran his fingers up my leg and onto my sore ass cheek. It burned when he grabbed it.

  Then, I felt him grab my sides with both hands. He ran his hands up, feeling each rib and then slowly moved them forward to cup my breasts.

  I could only let out a slight moan.

  He whispered in my ear, sending chills down my spine.

  “See? Wasn’t so bad.”

  I shook my head in agreement.

  His hand moved down from my breast, caressing my stomach before coming to rest on my area below. My pussy warmed up.

  I watched him walk back to his other toys and grab a ball gag. I could feel my body get warmer.

  “Open your mouth.”

  I did as told, and he placed the straps around my head, positioning the gag in my mouth perfectly so that I couldn’t talk.

  “What do you think?”

  He smiled when I tried to talk.

  You sly bastard. I couldn’t respond.

  “Watch me,” he said softly.

  He placed two fingers in his mouth and I watched as he slowly sucked on them. I could feel the euphoria begin in between my legs, knowing what he was about to do.

  I continued watching as his hand went down to my legs and he rubbed my lips with both fingers. I gasped at his touch. It felt so good.

  “Oh, Dylan!” I tried to say, but it came out as a muffled moan. My pussy was fully wet.

  “I can feel you Rachel. You love this don’t you?”

  I shook my head. I was not so much breathing as I was whimpering when he slid both fingers in me. Reflexively, I squeezed him tight inside.

  He pushed his fingers in and out, gradually building speed. I was encouraged by the power he had over me, it made our situation more intimate and interesting, knowing I could do nothing but take whatever he doled out. I had to stand there and let him finger me.

  “This is closer to what you want, isn’t it?”

  I couldn’t do anything but let him continue. It felt so good.

  As he pushed in and out, I could feel myself draw closer to climaxing. And right when I thought I could take no more, he stopped.

  I groaned, longing for more. Dylan looked at me directly, and even his gaze seemed to have control over me. I stared back at him, wanting his next move, whatever it would be.

  He dropped the towel he had been wearing. My eyes looked down on his member, standing tall and erect. He was ready to fuck me, and knowing that sent a chill down my neck. I squirmed, wanting him to make me feel great again.

  Standing behind me, Dylan moved his cock around on my pussy, taunting me. He slid it along my lips, and I heard him groan.

  My hands still tied above my head, I was ready to let him have his way with me.

  I moaned loudly as he slid into me, at first just the tip. I accepted him gracefully, feeling my juices drip all over him. Slowly he penetrated me, pushing me to new heights of pleasure. Once he was fully inside, he began thrusting slowly but deliberately.

  My breathing was half moaning, half panting. Dylan slid in and out, building up the euphoria and sending tsunamis of energy up my body. Everything was sensitive.

  “Let’s switch gears,” he said. I could not respond, only moan louder.

  Behind me, he gripped my sides with his hands and began to pound me hard. Each thrust was a collision, his abdomen hitting my ass cheeks and his cock poking deep against my insides. Each time I wailed, unable to contain the pleasure.

  He pushed himself against me, driving deeper and harder and faster. His hands moved from my sides, up to my shoulders, and then finally settled on my breasts. He grabbed them hard, the palms of his hands rubbing my nipples. He massaged them with every thrust, propelling me higher and higher. Unable to speak, I could only let him continue, my legs growing weaker with every second that he had me under his control.

  He continued to rail me, his thrusts increasing in force and speed until I was too far to turn back. I felt myself come harder than I had ever before. Dylan moaned as my walls squeezed him tight with each convulsion. I twitched uncontrollably, my whole body spasming in rhythmic waves.

  The ball gag did nothing to conceal my loud cries as I orgasmed with unstoppable force. My legs collapsed and I felt Dylan hold me, supporting me while I came. Time seemed to stop.

  As Dylan supported me, I felt something hot shoot deep within me. I could feel him throb inside me, each pulse sending more hot waves up into me.

  After what seemed to be a few very long minutes, Dylan reached up and undid my bindings, carefully easing me back onto the floor. I was finished, unable to think coherently and unable to stand without shaky legs.

  “What did you think?” he asked after he removed the ball gag from my mouth. Dylan was sitting behind me, his legs spread. I was sitting in between his legs, leaning back on his chest, naked and drained. My mind was a mess.

  “I…” It took everything I had to think straight. He waited for me to continue.

  “I - I loved it,” I said softly. There was weariness in my voice.

  “You’re no longer a first-timer,” he said quietly in my ear. I managed to nod in response.

  I leaned my head back on him, wanting only to be held after our rough play. He must have sensed the same thing, because he wrapped his arms around me and kissed the top of my head.

  I smiled inside, knowing that I was no longer a virgin to bondage sex. Not only had I tried it, but I loved it.

  “It was great getting to know you today,” he said. I laughed lazily and thought about how we had only first met in person a few hours before. It was a lot to think about.

  “I liked this a lot Dylan.”

  “I’m glad. Maybe someday we can do it again.” I wanted nothing more than that.

  “Dylan?” I tilted my head back and looked up at him. He looked down and met my eyes.

  “Yes?”

  “Thanks…”

  He had introduced me to something new, something fun and hot. He walked me through my first experience with bondage sex and it couldn’t have gone better.

  Our eyes still connected, he smiled and said, “There’s a first time for everything.”

  Book 3: Ménage à trois

  I was laying on my stomach, lounging on the bed with my laptop. I rolled over and stretched, tired of reading internet blogs and endlessly browsing the depths of the internet.

  You should really get to sleep, I thought. I just didn’t feel tired, even with all my bedroom lights off. It was beginning to get frustrating.

  I had gone through the day with barely any sleep. The night before, Tyson and I had gone out dancing. Tyson was my gloriously gay roommate, a tall, handsome, blonde-haired beauty of a man. Just the right amount of feminine and masculine traits. Not afraid to make decisions, but also in touch with his feelings. I’d be all over him if he were straight. Actually, we had kissed a few drunken times, and he always mentioned how hot I was. Maybe one of these days I’d win him over.

  The more adventurous one of us, he was always dragging me out somewhere, regardless of whether it was a Friday or Monday night. Last night it was a gay club, tomorrow it could be anywhere.

  And where is he tonight? I wondered. He had texted me earlier to let me know he would be home late tonight. I wondered how late. What time was it again?

  I glanced at the clock on my night table. 11:00pm. Not too late. If I was persistent enough, I might be able to doze off before midnight.

  I closed my eyes and imagined Tyson’s gorgeous face moving in to kiss me. Oh come on, Chelsea. Tyson’s gay. At least make it realistic.

  I tried to conjure another dreamy man. This time it was Cliff, my co-worker. I imagined us kissing in his office. God, he was stunning too.

  Cliff and I worked at the same advertising agency together. Actually, Tyson, Cliff and I had all gone to college
together. Tyson and I had been friends through college, sharing the same classes and now the same degree. Cliff, on the other hand, I knew only vaguely. It wasn’t until I landed my current job that I remembered we went to college together. I think he was in a different graduating class than I was. Maybe not, who knows.

  One thing I knew for sure was that Cliff was hot. We worked together on various projects, and the more I was around him, the larger my crush on him grew. There had been plenty of awkward elevator rides together, usually with me trying not to think about sexual scenarios, and him politely trying to say hello.

  The sound of Tyson’s voice brought me back to reality. I heard him open the door to our apartment, the jangle of keys against the door and the lock turning. Was he with someone else? He certainly wasn’t talking to himself.

  I sat upright in my bed, listening hard to what he was saying.

  “...I’m so glad this is finally happening...”

  Was Tyson luring another guy into his domain? He was fond of doing that.

  “C’mon. Let’s have a drink and relax.” Tyson’s voice sounded muffled behind a few walls and doors.

  I heard him go into the kitchen and open a cabinet. It was kind of exciting eavesdropping on Tyson’s night. Maybe I’d get to overhear a bunch of hot sex. I suppose that was another gift of living with him: I’d often get to hear him go at it late at night.

  How long has it been for you now? Oh boy. What had it been, six or seven months since I had even been on a date? That has to change.

  No shit.

  Great, now I’m having an argument with myself. Fortunately, it didn’t last long…

  “Chelsea, are you home?”

  I froze, heart nervously racing. What should I say?

  Nothing, Chelsea. Say nothing, and see what happens. The voice in my head was a compelling argument. Perhaps I’d stay silent and Tyson would forget about me. Plus, my bedroom lights were off, so if Tyson had been drinking, he might be easily fooled.

  “Chelsea?”

  Are you going to say something? Something in me kept my mouth shut. Then, out of nowhere: If Tyson doesn’t know I’m home, maybe I can watch him and his friend.

  The thought surprised me. I sometimes enjoyed watching gay porn, but never considered witnessing it in real life, let alone with my own roommate Tyson.

  Don’t even think about it, a voice inside said. But a stronger voice won - It’d be so hot.

  The possibility of eavesdropping was too enticing to give up. Call me a weirdo, but the thought of seeing Tyson and another guy get it on was a complete turn on.

  My heart was racing and I smiled to myself like a kid who sneaks past his parents late at night to steal candy.

  Would Tyson call my name again? Would he check to see if I was here? I heard more shuffling in the kitchen, and then eventually some more conversation.

  “Let’s go to my bedroom.”

  I breathed a sigh of relief. Tyson was done with me.

  “Sure, why don’t you lead the way?” That had to be the mystery lover man’s voice, but I wondered who it was. His voice sounded familiar, but I just couldn’t place it.

  I stalled a few more minutes, hoping that it would be just long enough for them to escape back into Tyson’s bedroom. Carefully standing up, I eased my bedroom door open ever so slowly, peeking out of the crack to make sure they left the kitchen.

  My heart was beating up in my throat, I felt like I was on an espionage mission. With the door open just wide enough, I tip-toed my way out into the hallway.

  No sign of my roommate. So far, so good. The kitchen was at the end of the hall, the living room adjacent to the kitchen, and Tyson’s room on the far end of that.

  I made my way to the kitchen as quietly as I could. My curiosity was getting the best of me, as it usually did. My thoughts kept drifting back to who Tyson might be with tonight. As I crept through the kitchen, I heard a door open.

  Shitshitshitshitshit. Don’t see me. Please don’t see me.

  I stopped like a deer in headlights and ducked behind the counter as soon as I heard voices.

  “I’ve got Magnums, is that alright?” asked Tyson.

  “Yeah, that’s great.”

  I heard Tyson exit his bedroom and walk to the bathroom. Still behind the counter, I forced myself to breathe slowly in an attempt to calm my nerves. A part of me questioned my choice to spy on Tyson, but a warmness between my legs told me to keep going.

  Noticing my palms were sweaty, I wiped them off on my leggings as I heard the medicine cabinet open.

  So that’s where Tyson keeps his condoms. I always wondered the location, but never would have guessed such an obvious spot.

  “Got ‘em. Now let’s have some fun…”

  I sighed again, knowing I just successfully avoided awkwardness. I waited a little while before moving again.

  Once outside Tyson’s room, I could hear more casual chatter.

  Who on Earth is he with? I wondered. The unknown voice sounded so familiar.

  I stood with my back to the wall, just outside Tyson’s bedroom. Taking a deep breath, I hesitated to continue. Should I really watch Tyson and his friend?

  Go to bed, Chelsea. You’re tired anyway. The voice of reason was strong.

  To hell with reason. Don’t be a wimp, just watch them for a little bit.

  There was no real harm in watching them, right? I crouched right outside Tyson’s bedroom door, fully prepared to see two hot guys make love.

  **

  I didn’t have to do much because Tyson’s door was already ajar. Hesitant at first, I peered through the opening. The first thing I saw was Tyson’s gorgeous, naked body. I had never seen Tyson completely naked before. What a pleasant sight. A bubble of anxious excitement rose up my chest.

  His body was wonderfully toned, his abs contracted as he leaned over a pair of legs. He was sucking his friend’s cock, but who it was I still couldn’t see, as the door hid his upper half.

  My jaw dropped at the sight of such a raw act. It was both dominant and submissive, and I could feel my body warm up. I couldn’t believe I was actually watching my roommate blow a guy. Slowly, Tyson’s head moved up and down, taking his friend’s cock fully.

  I remained crouched in silence, just watching my roommate. His mouth opened wide as he consumed his friend. I held my breath as I watched him lower his head all the way until his lips kissed the other man’s abdomen. God, he was probably better at deep-throating than I was. Masterfully, he moved up and down, in synch with his friend’s moans.

  I could feel my pussy warming up, and all I wanted to do was join in. God, to have such a hot man to play with.

  If only they knew I was right outside.

  Doubts came back for a second. Should I just go to sleep? Would Tyson get angry?

  He’ll get over it, I thought as I decisively shrugged away my concerns.

  I snapped back to the present moment upon hearing the sound of moaning. I peeked in again, and saw Tyson looking up at his friend, mouth still wrapped around his cock.

  “Cliff, your cock is so good,” said Tyson.

  Wait. What?

  “It’s so big too,” Tyson continued.

  If there was a record playing, it would have just screeched to a stop. My heart skipped a beat and the blood rushed from my head, leaving me dizzy.

  “Oh my God,” I said, forgetting to be quiet.

  Tyson heard me, quickly turned his head around in my direction, and our eyes awkwardly met for the tiniest fraction of a second through the sliver of opening between the door and doorway.

  “Chelsea?” Tyson questioned. His voice was more bewildered and puzzled than frustrated or embarrassed. What little of his face I could see conveyed a similar expression.

  Fuck. Fuckfuckfuck.

  I stood up quickly, taking a step back from the door. My whole body became rigid. I had no idea what to do. I supposed this was the fight or flight response in nature, only I was paralyzed with fright, unable to flee.
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br />   “Who is it?” I heard the other voice ask. Was it the same Cliff that I knew? My coworker at the ad agency? It sure sounded like it.

  Tyson opened the door and, true to my awkward nature, I did nothing except stare back at him, heart beating a million beats per minute and my throat completely dry. He had wrapped a robe around himself, but that didn’t hide his erection. I looked down at my feet as if they held the answer. It was my last resort, the decision that cemented my failure for the night.

  “What are you doing?” Tyson’s tone wasn’t as angry as I expected it to be. In fact, it sounded more like curiosity mixed with mild frustration.

  “Umm…” Despite my efforts, my nerves clouded my ability to think clearly. I was a dead girl walking.

  I looked up to face Tyson directly, but was distracted along the way. With the door now wide open, the whole room was visible. Behind Tyson, I could see Cliff sit up on the bed, still firm and erect. It was indeed the same Cliff I knew from work. The air rushed out of me and I felt winded.

  Tyson cleared his throat, waiting for my answer. I looked back at him, his fiery eyes looking into mine, and I tried once more.

  “I uhh…” Come on Chelsea, you have to say something. “It - It’s hot watching.” It was all I could manage to say, but at least it was the truth. I looked past Tyson at Cliff, hoping he would somehow back me up.

  Tyson turned to look at Cliff, then back to me once more, as if he didn’t believe what he heard. “You think it’s hot?”

  “Hey, what if she joined?” Cliff asked. I couldn’t believe my ears. I didn’t know Cliff that well, why would he suggest that?

  Tyson turned to around to face Cliff. Adrenaline shot through me like a jolt of electricity. I had no idea what was about to happen, but it seemed like everything was about to be turned upside down.

  “What? Seriously?” Tyson asked. It was over. There was no way Tyson would be into such a proposition. He wasn’t even attracted to women.

  And was Cliff? I swore he occasionally flirted with me, but maybe I just wished he did. Was Cliff gay? I never once considered it, always assuming he liked women.

  “Hear me out.” I was anxious to hear what Cliff had to say. “Men are new to me, but I’m familiar with women.” He paused, as if waiting for Tyson’s acknowledgement.