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25 episodes

episode Cabin of Temptation: Part 2 artwork

Cabin of Temptation: Part 2

CABIN OF TEMPTATION: PART 2 SMOKING WITH EMMA. Based on a post by a f winter [https://www.sexstories.com/profile1686626/afwinter] . Listen to the Podcast at Steamy Stories [https://feeds.feedburner.com/steamy-stories]. Based on a post by a f winter [https://www.sexstories.com/profile1686626/afwinter] . Listen to the Podcast [https://archive.org/download/fall-2025/CabinOfTemptation2.mp3] at Steamy Stories [https://feeds.feedburner.com/steamy-stories]. [https://archive.org/download/fall-2025/CabinOfTemptation.jpg] Introduction: Cabin of Temptation is an ongoing story told over four parts. In this chapter, the rest of the girls arrive at the cabin where some tensions immediately rise. Emma and Sam share some weed, but that's not all Emma wants in her mouth. Alexis went about making sure everything was up and running while I got settled and explored. Her father had been up two weeks ago to make sure everything was ready, and lock all the liquor away, but things like the Wi-Fi needed to be turned on. I was given the master bedroom for the trip and my eyes nearly bulged out of my head when I saw it. The king sized bed seemed tiny in the huge space. There was a couch and a couple of chairs around a coffee table in front of a fireplace with a large TV above it. All the furniture here, as with most of the furniture in the house, was dark wood with a real rustic feel. It was all handmade and I figured the dresser alone cost more than all my bedroom furniture combined back home. The master bedroom was only accessible via the bedroom, and that too was impressive. A huge tub with jets, glass shower stall, and his and hers sinks. The floor and countertops were both white marble. Large windows in both rooms overlooked the forest outside with a view of a far off mountain top peaking above them. The bedroom led out to a hallway that had two other rooms, Mr. McCarthy s office and a pool den. The office was one of the few rooms without large windows letting in copious amounts of light. The hallway overlooked the large family room in the center of the second floor. The main staircase in the foyer led up to it and had a huge table surrounded on both sides with L-shaped couches. It also had a small table with four chairs around it for more intimate playing and a fireplace of its own. Two hallways branched off from there to the north and south where a majority of the bedrooms were. These weren t as large as the master bedroom, but they were still spacious and well furnished. There was also a nook at the end of one of the halls with a bay window overlooking nature and a smoking den. Some of the rooms had more than one bed and I quickly lost count of how many there were. When I later asked Alexis how many people could sleep here; she said 20. The deck connected on the second floor with a doorway in the family room leading out. It had a hot tub made for a crowd and several lounge chairs, as well as a couple of outdoor tables and chairs. The deck was the latest addition and below it was a grill station that you d expect to find in a restaurant. The first floor housed the large kitchen that featured more of the marble from the bathroom upstairs. Like the furniture, the appliances were all handmade and appeared complicated to operate. The dining room housed a table with ten seats along its sides and one at each end. The table itself was beautiful, a dark cherry wood and glossy. There was a smaller family room on the first floor as well that resembled a library, and a small movie theater that could seat 10. The basement below seemed almost out of place. It was practical with no decoration, housing instead some supplies, a backup generator, and linens. I knew Alexis s family had money, but this was far beyond being comfortable. She expected the line of questioning and met it with a shrug. I didn t know we had this kind of money either, she had said. My dad is always griping about money even though I know it s never been an issue. We were all shocked when he showed us the plans. In the kitchen, I discovered a neatly handwritten list labeled Mr. McCarthy s Rules of Conduct . It was a list of rules the younger ones were expected to follow and I was expected to enforce. They were as follows: 1, No alcohol. 2, No drugs. 3, No sex. 4, No strangers. 5, Boys and girls are to sleep on opposite ends of the house. 6, No boys in girls rooms, or vice versa. 7, No going in to my office. Rule three was already broken and would continue to be it seemed. I knew rule one would be broken as well. Despite her father taking all the liquor, I knew one of Alexis s bags was full of alcohol. I told her I d look the other way if they all agreed to only drink in the cabin and not break anything. Rule two I was unsure of. I myself had some weed stashed in my bag upstairs that I planned to enjoy in private. McKayla was fairly straight laced for fear of not being able to play volleyball, and Sydney had a fear of getting in trouble. I had no idea about Alexis, Natalie, or Emma, but as long as they weren t doing anything stronger than weed I was likely to ignore it. Rules 4, 5, and 6 didn t seem to be an issue, and I didn t think his office would hold much interest for the girls. Just as I finished reading the list, I heard another car crunching up the gravel drive. I walked towards the front door only to see it burst open a moment later. McKayla looked at me, her blue eyes wide in panic. Bathroom? She blurted out. I pointed towards the nearest one and the tall blonde disappeared in an instant. The other three girls walked through the door a moment later, all of them greeting me with bright smiles. Natalie walked over and hugged me, the tiny Japanese dancer pulling me to her with surprising force. We re so glad you re here, she said. Yeah Mr. H, Emma added. I saw in her eyes a similar look that Alexis had in the car and I grinned in return. Sydney nodded her agreement with her friends. McKayla emerged looking far more relieved. So you didn t piss yourself? Emma teased. McKayla grew red and glared at her friend. Sydney and Natalie broke into laughter, which made McKayla crack a smile. I helped the four of them get their things from the car and up the stairs with Alexis appearing just as we dropped the last bag. About damn time, Natalie teased the red head. At least we had a big strong man to help us. It took me a little longer than expected to get the remote camera feed off, she said. We don t want my dad tuning in and seeing Emma getting stoned. That answered that question. All eyes went to me when Alexis said that, but I showed no change in my expression. I did look at Emma with a cocked eyebrow. Get stoned on what? I asked. She shrugged, Just weed. JUST weed, Sydney spoke up sarcastically. The other four girls sighed without words. It was clear that this was a topic that came up a lot. It's no surprise, Sydney s father is a rather prominent figure at their church and she grew up with a conservative view. I had often seen the conflicts that emerged with the other girls over stuff like this in the past, especially between Emma and Sydney. They were polar opposites in their upbringing. I remember when Emma first got her nose ring, Sydney was amazed that her parents would let her do such a thing. Oh come on Syd, Emma huffed. The rest of us have done it. McKayla doesn t have practice for another month, so she said she s gonna do it. You ve seen us all high and how much fun we have. This is the perfect environment to try it. Sydney turned bright red and turned up her nose, It's still illegal in lots of places. So? Emma countered, It s getting legalized everywhere, and you drink when we hang out. It s illegal to do that. Get that stick out of your ass already. That s enough, I said, my voice making all of them pause. For a moment they were all students again, their teacher taking authority. If Sydney doesn t want to do it, then she won t. At the same time, you re all adults now. Sydney, Emma can smoke if she wants. My eyes went to her again, As long as she at least blows the smoke outside. Emma nodded. And Emma, don t pressure her. She ll try it if she feels comfortable and we both know she won t enjoy it if she s doing it for someone else. Emma looked at the ground and then gave a small nod. Sydney looked at me with a bit of thanks in her eyes and smiled, tucking some of her brown hair behind her ear. The crisis appeared to be averted. Natalie broke the silence, I don t know about you bitches, but I m getting hungry. I m gonna get started on dinner. Need a hand? Alexis and I asked at once. Natalie grabbed Alexis by the hand and began to pull her along, I heard her first. You all relax and we ll call you when it's ready. Alexis and Natalie went to work on dinner, McKayla wanted to explore the house, Sydney went to the deck to practice guitar, and I didn t know where Emma went. I went to my room and got unpacking. I decided to not live out of a suitcase if we had a whole week here, so I unloaded my things into the dresser. I also grabbed a couple of hangers from the walk-in closet and used them to hang a couple of my nicer shirts somewhere more accessible. I had been told we might do a couple of nice dinners, so I should have some nicer clothes. Now all settled, I made my way down to the second level. At the end of one of the hallways, I spotted Emma sitting in the window seat of the nook. The window next to her was cracked and it wasn t hard to guess what she was up to. As I got closer, I saw her pull out a vape pen, take a pull, and blow the smoke out the window. She turned her head in my direction and spotted me, making her jump. I wondered if I just surprised her or if it was a reflex to being caught with weed by a teacher. Either way, she relaxed and melted into a smile. I saw she had headphones in that she popped out as I got closer. Hey Mr. H, she said. You can just call me Sam now, I told her. She nodded and said, Funny thing is, if you d caught me doing this just a couple of weeks ago, you d be busting me probably. She held her vape pen up and took a drag, blowing the smoke out the window. She suppressed a slight cough and held it towards me, Now I m seeing if you want any. I shrugged and took it from her, taking a seat next to her. She shifted her legs closer to herself as I got situated and took a hit. I blew the smoke out and looked her over. Emma was the shortest of the group at just over 5 even. A pair of jean shorts and a faded green V-neck adorned her body. She had the curviest figure of all the girls, and the largest tits. They looked to be at least D s to me. She had sandy blonde hair that might be a different color depending on the week and a pair of light blue eyes. Numerous freckles highlighted her nose and cheeks. I took another small puff right as Emma asked, So, did you and Alexis fuck? I coughed violently in surprise, which made Emma laugh. She took the vape pen back and hit me playfully on the back. I m sorry, I coughed, what? You and Alexis, she said before taking a hit. It s cool, we all talked about it beforehand. You re free game this week. I say in surprised silence for a moment before asking, You all talked about this? Emma nodded and handed me back the pen. Everyone s agreed that, as long as you re up for it, any of us can fuck you at any time. Sydney mostly remained silent, but she didn t disagree. I couldn t think of what else to say, so I took a silent hit and looked out the window. In the silence, I could hear Sydney s guitar music wafting through the air. You know Mr. H, I thought it was really hot when you put on your teacher voice earlier. I couldn t help but smirk. It s what made me attracted to you in the first place, she added. Her hand went to the v part of her neckline and gently ran along it while she made her lips pouty, A girl like me needs a little authority. Is that so? I asked. She nodded and shifted onto her knees next to me. She stuck her chest out, I m a rebel and a free spirit, but sometimes I just need a man who will take control. I took another hit. Already I was feeling it and, mixed with her words, the feeling was one of power. I felt authoritative in a whole different way. I ve been surrounded by just boys for four years, she bit her lip and trailed off. But you need a man, I declared. She nodded and cast her eyes down again. Her hands were folded in her lap and I knew what she was waiting for. The next move was mine to make, and she was offering herself to me. I reached out and placed my hand on her cheek and she nuzzled herself into it. Let s go to my room, I said as I began to stand. She grabbed my hand and said, No. Here. Please, sir? I looked around. But the others. We all agreed no jealousy, she planted a kiss on my hand, and no secrets. I like that someone might see. I thought for a moment and then nodded. If they were all okay with it, then why should I not be? I d always been a bit of an exhibitionist. I nodded my approval to her and her face lit up. Take off your shirt and bra, I ordered. She wasted no time, both off her body in a flash. She sat before me, exposed, her eyes still down. I admired her large tits and pale nipples, first with my eyes and then with my hands. Thanks to her kneeling on the window seat, I had easy access to them. Touch me wherever you want, sir, she encouraged. However you want. Get on your hands and knees, and take off your shorts. She obeyed, getting naked and then in position. Her back curved alluringly, her thick ass in the air. I ran my hand along the curve of her back, feeling the warmth of her body, until it came to rest on her ass. She looked at me expectantly, her bottom lip tucked behind her teeth. I gave it a light smack as I didn t want to make too much noise and she moaned. I undid my shorts for the third time today to fish my cock out. Emma s wanting eyes watched every one of my movements with anticipation. When she saw my thick cock at attention before her, she gasped. I told her to open her mouth and then navigated my cock to it. She wrapped her mouth around it as soon as she could and ran her tongue along the bottom. Thank you for this cock, sir, she said before plunging down on it again. I grabbed a handful of her hair and pushed her further down my cock. She gave no resistance, more than half of my length disappearing in an instant. She paused when my head hit the back of her throat, but she continued on as soon as she relaxed. Her mouth was so warm and inviting, her curious tongue exploring my shaft as she moved along it. I let her pull back a little before I pulled her further down again. You re going to take all of it, I told her. She looked at me with those big eyes of hers and nodded. I used my firm grip in her hair to pull her down further. She choked, she gagged, she sputtered on my cock, but she never let up. Between my coaxing and her will, we got her there. Her nose pressed right against my body and I felt the sensation of my whole cock swallowed by her. It was electric and I let her know with a lusty groan. Her eyes brimmed with tears while she worked her head back and forth to fuck my cock with her mouth. Good girl, I growled. Good cocksucker. She mewed, pleased with herself, and pulled her mouth off of my cock. I watched as my cock reappeared, the whole length now shimmery in the late afternoon soon. She came off the head with a gasp, her chest heaving as she desperately worked to catch her breath. Her chest and cheeks were red with effort, but I could see how hard her nipples were. A string of saliva kept my cock connected to her lips. Fuck, I love choking on your cock, sir. She went back for a second helping, driving herself down with my hand on her head still encouraging her. Every now and then I d push her over the halfway mark, making tears appear in her eyes again. My other hand found her ass again and ran along the curve of it. She wiggled it at my touch. I moved along her ass to her thighs, finding the space between them to explore her slit. Emma groaned around my cock as I found her already wet pussy and that some of her arousal had already run down her thighs. I guess she really did love choking on my cock. I probed her with my digit, prompting her to spread her legs a little to give me better access. I pressed my finger into her and felt her warmth around me. I worked it as if it were my cock and fucked her at an even pace. Occasionally, I would curl my finger against her walls and find the spot that made her moan hard around me. The vibrations of those moans sent extra jolts of pleasure along my cock. I needed her. Not just her sucking my cock, but the feeling of being inside of her. I pulled my cock from her mouth and grabbed her hips, pulling them towards me. She lowered her face down and shook her ass at me. I grabbed my cock and smacked it playfully against her thick ass. Do you want me to fuck you? I asked. Yes! She practically shouted. Please sir, fuck my little pussy. It's all yours. How could I say no? I looked up to see the trees, the far off mountaintop, the beautiful scenery present in the bay windows all set dressing for the ass in the air waiting for me. The head of my cock came against her pussy and I pushed myself in, the first few inches sinking in slowly. I could see the faint reflection of her reaction in the mirror, her mouth falling open and her eyes rolling back as if my cock had just shut off some part of her brain. She exclaimed, Oh God! I smacked her ass and pulled her head back by her hair. Be quieter, slut, or I ll pull out now and leave you here. Emma nodded and lowered her head back down. Her hands braced herself against the windows as I grabbed her hips and began to thrust. I didn t bother with buildup, we both needed this to be hard and desperate. She bit back moans and moved her hips just a little to meet my thrusts. I slammed myself into her, my length plunging deep. She raised herself up just a little, her tits bouncing with every thrust. She made small, desperate noises but managed to keep her volume low. I grabbed onto her hair again and pulled it back, giving me plenty of leverage to pound her. It was great sex, but the weed worked to enhance every little feeling beyond what it would normally be. I felt powerful as I fucked her. I let her hair go and her face fell back to the window seat. Her body tensed as an orgasm hit her. She began to call out, but immediately put a hand over her mouth to help quiet it. I watched as the tremor rocked her body, her pussy squeezing hard on my cock so that I almost had to stop fucking her. She looked up at me, breathing heavy, and grinned. Time slipped away from us. I don t know how long I stood there thrusting into her. Orgasm after orgasm rocked her body until she seemed to barely be conscious. Finally, I felt that familiar building in my pulsing cock. I m gonna cum, I told her. Wherever you want, she said through her haze. Inside you? She nodded with heavy breath. I gave the last bit of my energy into the final few thrusts. They weren t at the same rhythm as the others, but more drawn out as I felt every inch of her pussy around me. I slammed in one last time and released a torrent of cum, filling up her pussy. I almost collapsed against her, but I managed to pull out and slump next to her. She rearranged herself so that she was sitting again, her body resting against mine. We were both sweaty messes basking in the post orgasm glow. Both of us were facing down the hall, uncovered for anyone to see, but no one else ever appeared. As we regained our strength, I saw her reach between her legs and gather a little of my cum leaking from her onto her fingers. With her eyes on mine, she brought them to her mouth and licked them clean. Fuck, I breathed. She smiled. Thank you, sir, for all the cum. I really, really needed to be fucked. She leaned over and kissed me, a thankful thing that I readily returned. We basked in our post sex glow for a bit until Natalie's voice came over the intercom system to announce that dinner was ready. Emma sat up and stretched. I worked up quite the appetite, she said as she gathered her clothes. We went and got our

14 Aug 2026 - 1 h 0 min
episode Cabin of Temptation: Part 1 artwork

Cabin of Temptation: Part 1

CABIN OF TEMPTATION: PART 1 DRIVING WITH ALEXIS Based on a post by a f winter [https://www.sexstories.com/profile1686626/afwinter] . Listen to the Podcast [https://archive.org/download/fall-2025/CabinOfTemptation1.mp3] at Steamy Stories [https://feeds.feedburner.com/steamy-stories]. [https://archive.org/download/fall-2025/CabinOfTemptation.jpg] Introduction: Cabin of Temptation is an ongoing story told over four parts. Each part will be made of several chapters. The first part is largely an introduction to the setting, the characters, and their relationships with some seeds planted for later growth. This first chapter introduces us to Sam Holloway, the teacher and point of view character, and Alexis, his former student and red headed wild child. The road seemed to stretch on endlessly before us, but Alexis assured me that our journey was near an end. We d turn before long into thick woods and travel through narrow, winding roads until we reached her family s cabin. I had no choice but to trust her as GPS had given out nearly 20 minutes ago. There s good Wi-Fi and okay reception at the cabin, she d told me, but you can t get there unless you know the way. So here I was, driving alone in the middle of god knows where with a girl who was my student just a couple of weeks ago. Her and her four best friends had been together from first grade all the way through high school and now they had graduated with very different futures ahead of them. They had decided to kick off the best summer ever with a week-long stay at Alexis s family cabin. Alexis and I were heading up before everyone else, the four other girls and four guys. All of their parents had had concerns, of course. None of them could take the time to chaperone such a trip and many feared what teenagers would get up to out there, even though they were all, legally, adults now. The plan seemed to be dead before it began until Emma brought up the idea of me accompanying them all. I d taught the girls US History their sophomore year and Government their senior year. The girls took to me easily and I came to enjoy their company. We got to know each other over the years, but I always remained a detached authority figure. They liked and respected me, and their parents trusted me, which is why all of them agreed as soon as my name was attached. Of course I wasn t told I would be doing this until after the parent s agreed. I was hesitant to do it, but I acquiesced in the end. Being out here now, I was glad I had agreed. The sky looked bluer than in the city, the world more open. A couple of wispy clouds floated lackadaisical over the rolling hills to our left, passing over the empty road to the tree covered mountains to our right. We had the windows halfway down and the air filling my lungs felt like it was renewing me from the inside out. Having a cabin out in a place like this must be amazing, I said. I m sure it was nice getting to come out here all the time growing up. Alexis chuckled as she gazed out the window, This isn t the original cabin. That one is just a little out of town and is like one of those cabins you see in a horror movie. Still nice, just a bit run down ya know? Right, I nodded. She went on, This one is pretty much brand new. My dad got the land from a client like five years ago for some legal work he did and he built this place and gave the old family cabin to my uncle. Oh, I said, is it nice? Now she laughed, Mr. Holloway, it's a mansion. I told you to call me Sam. Old habits, she shrugged, it s hard to not think of you as Mr. Holloway. I moved on and asked, When is everyone else arriving? McKayla is driving the rest of the girls and they re an hour or so behind us, she told me. What about Todd and Mike? I asked, looking across the car at her while she looked out the window. And McKayla s not riding up with Evan and his brother? McKayla and Evan broke up, she stated. Didn t really make sense for him and his brother to be there. Sure, I drew the syllable out. And Todd and Mike? Her gaze never left the window as she went on, Well, once we decided about Evan, we felt like we didn t need two other boys. So it's just me and you five girls? I felt my heart beginning to race. Alexis finally looked towards me, a smirk on her heart shaped face, Yep. My eyes narrowed and I shot her a glance. I didn t like that they had yet again pulled a fast one on me. Her smile only broadened. I couldn t see her emerald eyes behind her large round sunglasses, but I could feel the mischief burning there behind the tinted glass. Aren t I a boy? I objected. She giggled, Mr. Holloway, you re a man, not a boy. I skipped the name thing and asked, And do you parents know about this? She shook her head and tucked a loose strand of dark red hair behind her ear. Of course not. Why didn t you tell me? Because you wouldn t have agreed to come, she said very matter-of-fact. I sighed. She was right about that. No more tricks, okay? I said. I know you re all not my students anymore, but it would still be very frowned upon if anyone knew. She turned her body towards me now, the smile on her lips changing. It became a devious thing, as if she had been waiting for this moment. That wily look on her face also crept into her voice. You re right Mr. Holloway, she corrected herself, Sam, we aren t your students anymore. And as of three weeks ago, we re all eighteen now. A shiver ran down my spine. My mouth went dry. I foolishly asked myself why she would say that, but something deep down knew why. Alexis was a notorious flirt and I d seen many boys, and a number of my colleagues, become flustered by her with just a few words. Maybe it's because I ve been doing this for over a decade, but I had seemingly been immune to her charms. I d always been able to rebuff her advances or laugh them off, but being alone with her in the car changed the dynamic. To my chagrin, Alexis went on, You re going to be alone with five beautiful women all week, and all of them have massive crushes on you. We ve all talked about it. My heart felt like it was going to pound out of my chest. I tried to keep my eyes trained on the road, but I couldn t stop myself from glancing her way. The white tank top under her semitransparent yellow striped shirt seemed to be riding lower than before, her full tits barely contained. The tank top, like a tight second skin against her toned stomach, was tucked into her jean cut offs. How did I not notice how short they were? Her pale thighs were fully on display and if she moved them, I thought I might be able to spot whatever underwear it was she had on. If she had any on at all. The sunglasses still hid her eyes, but I could feel her gaze. Her lips were slightly parted, pouty and alluring, the edges pulled into a knowing smile. She reached her arm over her body and ran the tips of her fingers ever so lightly against my forearm. Not just little schoolgirl crushes either. They might have started that way, but they certainly didn t stay that way, she went on, her voice growing husky. I ve had so many fantasies about you Sam. About us together. She placed her hand fully on my forearm and ran it along it, We could make them a reality. I managed to speak despite my mouth being bone dry, You re, I m what? She cut me off. Willing? Ready? I m not your student anymore. I m not asking to date you, I m going away to college at the end of the summer and I want to make this the best summer it can be. Her hand moved from my forearm to my crotch, And that involves sucking this cock. My mouth fell open but no words came out. I let out a short gasp as she touched my crotch, but it morphed into something like a moan as her fingers brushed against my cock through my jeans. I didn t even realize I had become so hard. Have you ever gotten road head, Mr. Holloway? Her voice was teasing again, and sweet as a glass of lemonade. She took off her sunglasses to reveal those bright green eyes full of mischief. I ve always wanted to give it. Alexis, I groaned as her hand rubbed more fully against my cock. I thought I should resist, but the voice in my head asked why the hell I should. I, Yes. I want this. I slowed the car down a little as she began to undo my jeans. Her hands made quick work, her own eagerness causing her to fumble with my belt. She got it undone, along with my pants, and fished out my cock. She paused for a moment and wrapped her hand around the base. Jesus, she breathed. I fucking knew it. The simple touch of her hand around me caused me to groan. How long had it been since someone touched me like this? Even though there was nothing illegal about what we were doing, it was still wrong in a number of ways. As Alexis leaned forward, her mouth inching towards the head of my cock, I found myself holding my breath. Her lips parted, her pink tongue snaking out and touching the tip. I groaned and tightened my grip on the steering while. She looked up at me with wicked eyes as she swirled her tongue about the tip, her hand pumping a couple of times with just the slightest of pressure. As soon as precum appeared at the tip, she licked it up and giggled. I knew you had a big cock, she whispered hungrily, her hand continuing to work my cock. Alexis s lips wrapped around the head of my cock and I nearly swerved off the road. I heard her giggle at the reaction, the sound muffled. Her tongue began to massage my thick shaft while her head worked up and down at a steady pace. The hand wrapped around me worked in concert, providing additional pleasure to where her mouth did not yet reach. Though I wanted to grab onto her ruddy locks and push her down further, I knew I needed to keep a certain amount of control to drive the car. Alexis seemed to know this as well as she sucked me, her efforts concentrated on a slow and sensual blowjob. Her tongue dances about my head as if trying to find the spots to make me moan, which I did freely. She seemed to be enjoying giving me head just as much as I was enjoying receiving it based on the sounds she made. Oh fuck, I groaned when her tongue hit a sensitive spot on the underside of me head, you re really good at this. Alexis lips departed my cock and I felt disappointment. Her face stayed close to mine, her wide smile plastered on her face again. Her hand never stopped its slow motions. I ve had plenty of practice, she smirked. And I ve been wanting to do this to you for a long time now. She leaned forward and planted a kiss on my cheek. Her eyes looked out to the road, We ve still got a little bit before the turn off. Now where was I. Her words trailed off while she leaned forward, her warm breath splashing against the now shining head of my cock. It twitched powerfully as her mouth enveloped it again, her tongue finding that spot again with ease. At the pace she was going, I felt like I could last for hours under her expert manipulations. I was nowhere near cumming, though every once in a while she could concentrate her efforts on one spot or take me just a little deeper and send a jolt of electricity through me. We passed another car and I wondered if they could spot the bobbing mop of red hair. After another ten minutes of this, she sat back up and let my cock go. I let out a disappointed sigh, the air of the car a poor replacement for her expert mouth. I heard that devilish giggle of hers again as soon as she read the disappointment on my face. We re almost at the turnoff, she told me, I want to make sure we don t get lost. There s plenty of time to finish this later. When she said this , she gave my cock a firm squeeze. Sure, I said in my best nonchalant voice. There was no way my cock was going back into my pants in its current state and I worried that I would be stuck driving with a raging hard on. After Alexis told me to turn on a narrow road between some trees however, my focus shifted entirely to carefully navigating it and that caused enough distraction for me to calm down. I was assured that no one uses the road, but there were enough blind turns to make me cautious all the same. You must be pretty excited about Stanford, I said in an attempt to provide further distraction. She shrugged and gave a non-committal, Yeah. That s not the response I d expect from an excited person. She sighed, I am excited. It s exciting. It s just She weakly smiled and turned her eyes towards the passing trees, Everything s changing, you know? I m going west, Emma is going east. Natalie s gonna stick around for a bit, but she ll probably head off when her commitments with her dance academy are done. McKayla got a scholarship to CSU, so she s staying here. So is Sydney. We ll be all apart for the first time since we were 6. It s just a big change. I nodded, It is, but just because you re all apart doesn t mean you can t stay close. Alexis shot me a look bordering on an eye roll, Are you still close with all your childhood friends? Well, no, I admitted. But I wasn t close with anyone the way you all are. And technology is different now, it s easier to stay in touch. Yeah, we have texting now and you just had carrier pigeons, she teased. I felt a flush creep up my neck, but still I chuckled, That and you don t have to sit for a painting if you want to send a friend a picture of yourself these days. She chuckled dryly. We ll still be apart though. We ve already changed so much in the last few years. If we didn t have such a history, I m not sure we d be friends. I reached across the console between us and placed my hand on her thigh, giving it a squeeze. That s why we re doing this cabin trip, she went on. It s supposed to kick off the best summer ever, but I know we re all gonna be really busy and Emma s living early July. No matter what, we ll have this week together. Yeah. The five of you together and your former teacher. Alexis giggled and put her hand on mine, leading it up her thigh until my pinky was brushing against her jean shorts. I pushed my hand a little further until it pushed beneath the hem of the cutoff. As I came in contact with the place where her thigh and crotch met, I discovered she wasn t wearing anything under them at all. You being here is why it ll be the best, she purred. My hand remained where it was, another finger slipping into her cutoffs. She adjusted her hips to give me more access until my fingers touched against the edge of her slit. Now it was her turn to gasp, the noise turning into a sound of satisfaction. I found her slit, wetness already present upon her lips. You really liked sucking my cock didn t you? I asked her with a sideways grin. I really did, she hummed happily. The barrier of her shorts was slightly frustrating, keeping me from fully exploring her pussy, but the limited reach added a touch of teasing excitement as well. As I probed at her, she moved her hips and let me know she was enjoying it without words. I briefly dipped a finger inside of her, though I couldn t get far due partially to the angle and partially how tight she was. The smell of her sex began to fill the car and I hoped we weren t too far from the cabin. My question was answered not even two minutes later as we turned and it came into view. Cabin was too small a word. That evoked the image of something tucked into a mountainside with little more than four walls and a roof. This was, as Alexis had said earlier, a mansion. The tree lined path led right up to the circle drive of the three story building. Its huge red front door faced us, a splash of color on the mostly light wooden facade. The logs of the roof were a darker color, sitting on it like a hat. The windows were large and numerous to allow plenty of natural light to spill inside. It just got larger as we got closer and my mouth fell open in awe. It has that effect on people, Alexis laughed when she saw my reaction. She fished around her bag at her feet and pulled out a set of keys. She told me that the walk from the garage to the bedrooms was a pain and we could move the car later. I put the car in park and the two of us got out. It felt good to stretch my legs after the long drive. Doesn t your dad have cameras watching this place? I asked. Of course, she said. But they re dormant unless something sets off the alarm. So he has no way of seeing us right now? She nodded as she pulled her bag from the trunk. Good. I m not waiting longer. She began to smirk as I came upon her, pushing her back against the car. I kissed her with all the lust and desire that was boiling inside of me. She met my lips with as much eagerness and wrapped her arms around me. Our tongues met like old lovers long kept apart finally reuniting. Our bodies were pressed together and it felt like the heat of our need might burn our clothes off. Mr. Holloway, she breathlessly said when we parted, her hands falling to my belt again. I didn t correct her on the name this time. There was something about her calling me that that gave an extra bit of lewdness. I did away with her shirt and tank top as fast as I could, her bra disappearing just as quick. My hands cupped her full tits, perky pink nipples already at attention. She let out an Oh God as I brushed my thumbs over them. She had my cock out again, her grip on it tighter now that we didn t have to worry about the road. I growled as she jerked me off, my lips finding her neck. My teeth grazed her skin playfully before I bit where her shoulder and neck met. One of her hands left my cock and gripped onto the back of my head as I did so, her cry of pleasure joining the forest sounds around us. My hands moved to her ass so I could lift her up. She let out a squeal of delight as I easily lifted her, walking us over to the hood of the car. She wrapped her arms and legs around me while I moved us, her lips planting small kisses along my neck. We paused for just a moment after I set her down in order to shed the rest of our clothes. I looked over her now exposed body, taking in the full view of her finally. She bit her lip as she looked me over in return. Fuck, I breathed, you re so sexy. Right back at ya, stud, she said as her hands passed over my broad shoulders. I kissed her again as I gripped my cock and led it to her pussy. Her legs spread for me and we both inhaled sharply when my head touched her. I ran the head along her slit to spread her ample wetness and lube my cock. My head split her entrance, the first inch of me disappearing inside of her. Shit, she said as her eyes went wide, you re so big. Are you okay? I asked, my tip resting inside of her. She nodded. More than okay. I ve just never had anything this big inside before. She rocked her hips down to push more of me in. At just shy of 8 inches, I know I m longer than average, but not big enough to scare most girls off on sight. My girth is what sets me apart from most other dicks I ve seen in porn or otherwise. I ve been told I make girls feel full in a very satisfying way. Based on the look on Alexis s face as I pushed deeper inside of her, the rumors were true. I moved my hips to work myself deeper, her own body moving to help it get there. Her hands rested on the hood of the car to keep herself upright and her fact level with mine. We alternated between hungry kisses and watching my cock inside of her. It was amazing to watch her small pussy adjust to me, take me deep. She draped an arm onto my shoulder and dug her nails in as I finally buried myself fully into her. Fuck me, she said as she stared into my eyes. I readily obliged. I pulled out a few inches and pushed them back in, falling into a steady rhythm. She moaned louder, letting go of my shoulder and falling back on the hood of the car. I grabbed onto her hips to better drive myself in and out. She made sounds somewhere between words and moans, her hips lifting off the hood of the car. Her legs wrapped around me, her feet pressing into the small of my back to keep me in place. As if I was going anywhere. The warmth of the day on top of the activity made me begin to sweat. A sheen appeared on her body as well, her form appearing almost angelic now as her pale body glowed in the sun. She began to mumble something. Like that? I asked. She nodded, Gonna cum I reached a hand between her legs and pressed my thumb against her clit. I worked it in small circles while my cock continued to pump into her. The added pleasure made her mouth fall

Yesterday - 1 h 0 min
episode Seducing the Shy Guy: Part 3 artwork

Seducing the Shy Guy: Part 3

SEDUCING THE SHY GUY: PART 3. OLIVIA AND A MORE CONFIDENT COREY GET TOGETHER AGAIN. BASED ON A POST BY LEADER12 [https://www.literotica.com/authors/Leader12/works/stories], LISTEN TO THE ► PODCAST [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy3.mp3] AT STEAMY STORIES [https://feeds.feedburner.com/steamy-stories]. [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy3.jpg] Around 5:00 pm on Tuesday, Olivia sent Corey a text message. Olivia: Still interested in getting together tomorrow? Olivia started laughing when the reply came back almost before she hit the send key. Corey: Yes! Olivia: Meet me at the Starbucks by the high school at 10:00, okay? Corey: OK. Looking Very forward to seeing you! Olivia smiled as she tagged his text with a heart. At 9:59 Wednesday morning, Corey walked into Starbucks. He scanned the area and quickly saw Olivia sitting in the corner. As he walked toward her, she looked up, and they both smiled at each other. Olivia was wearing a white halter top that hugged her small breasts. Corey's smile got even bigger when he got closer. "Hi, my name's Corey. Would it be okay if I sat here?" Olivia smiled, but before she even answered, Corey continued. "Don't worry, it's okay if you say no. I'm not a weirdo, and I won't create a scene if you prefer I not sit here." Olivia was almost laughing by this point. "So, tell me.; Was it Cary?" she started. "Corey," he corrected her. "So, tell me, Corey, why did you want to sit here?" "Would you like me to make up some answer about this being my favorite table, or should I just tell you the truth; that I wanted to meet the prettiest girl in the place." Olivia tapped her fingernails on the table as she looked up at Corey. "Well, I think you're full of shit, but I like your style." As she tipped her hand toward the available chair, she continued, "have a seat." Corey sat down. "So," Olivia continued, "you seem to be pretty smooth. Are you always this self-confident when meeting new women?" Corey couldn't take it anymore and started laughing hysterically. Olivia followed right behind. Other people in the store turned their heads toward the two of them. When they finally calmed down, Olivia looked at Corey. "You know, it wouldn't be unreasonable for you to do that with a girl you didn't know." "Olivia, you've done wonders to make me feel like I could be a little more comfortable with a woman I just met at a party or in some other group environment, but I don't think I'm quite ready to walk up to someone out of the blue and say anything like that." "You Could do that, Corey. You're cute, and I liked the qualifier that you're not a weirdo. But for now, go order your drink." Corey got his drink and came back to the table. "I wanted to talk to you before we went back to my house," Olivia said. "What I did the other day with you; I'm not even sure why I did it. I mean, when Melissa said something about you being shy, it just hit me hard because it reminded me so much of me when I graduated high school. Now, I don't go around looking for shy guys;" Olivia looked around to see how close people were sitting next to them, and she leaned forward as she lowered her voice to almost a whisper before continuing, "just to be their first fuck." Sitting back and returning to a normal voice, she went on. "But, of course, I know you. I've known you for a long time. And you've always been nice to me. So, I wanted to help you out." She paused and took a sip of her drink. "And truthfully, I wasn't sure if I could really go through with it. But I'm really glad I did." "Me, too!" Corey added, causing both of them to smile. "I just wanted to get that off my chest," Olivia continued, again in a soft voice. "And I didn't want to just have you come to my house, fuck me, and leave. That's why I wanted to meet here. I hope that's okay." Corey chuckled. "Jesus, Olivia, you think I'd complain about spending time with you just talking? I mean, I'd be lying if I said I hadn't been thinking about stuff I hope we'll do. But even being here with you is really nice." Then, after a short pause, he continued, "But don't worry. I know I'm not your boyfriend, and you're not my girlfriend. But we can just be friends, right?" Olivia reached across the table and took Corey's hand in hers. "Yes, Corey, we can just be friends." Again lowering her voice, she said, "Friends who sometimes fuck!" They both smiled at each other. "Come on", Olivia said. "Let's go for a walk." They grabbed their drinks and walked out the door. Olivia took Corey's hand in hers and turned toward the high school. They walked the short distance in silence, but as they crossed the final street and arrived at the actual campus, Olivia stopped. "I walk around here sometimes. For some reason, I find it peaceful and calming. But I actually have very conflicting feelings about my days here. On the one hand, I loved high school. I had a bunch of girlfriends; mostly because your sister brought me into her group. Even in the group, I wasn't one of the popular kids at school." Corey looked surprised. "Really? But you were a cheerleader? All the cheerleaders were popular." Olivia laughed. "I was only a cheerleader because your sister forced me to try out. I was always a little embarrassed when I was wearing my cheerleading outfit or we were performing." "Huh? Half the girls were jealous they weren't cheerleaders, and all the guys loved watching the cheerleaders. Why were you uncomfortable?" "The guys weren't looking at me when we performed. The were looking at the other girls. The ones with big boobs and bouncy hair." Then she laughed. "And bouncy boobs." Corey turned Olivia toward him, grabbing each of her hands in his. "This guy was watching you. Every. Single. Time." Olivia smiled and gave Corey a big hug, being careful not to spill her coffee. "I'd call you a liar and say you were just saying that to get in my pants, except you already did," she said laughing. "Thank you, Corey. Good to know there was at least one guy watching me." She continued holding one of Corey's hands as the continued walking. "But as much as I enjoyed spending time with my girlfriends, I was always depressed about not having a boyfriend. Or not really even dating. It was hard." They continued walking in silence. She led them over to the football field, where a couple of guys were running on the asphalt track that circled the field. They both tossed their empty cups in a garbage can. "I spent a lot of time here performing our routines and watching games," she said. "Me, too," Corey said. "Really? I don't remember you in your cheerleading outfit. I bet you looked hot," Olivia said, laughing. "Uh, yeah, I meant watching the games." "Yeah, I know," she said, again laughing. They walked past the stands and then continued walking behind them. "Do you think all the rumors were true?" Olivia asked. "What rumors?" Still holding his hand, Olivia led them behind the stands. "You know; that after practice, some of the cheerleaders gave guys blowjobs here." Corey laughed. "I really don't know. I can assure it never happened to me." "Yeah, I was never involved in that either." Still holding Corey's hand, Olivia started walking under the stands, weaving between the metal structure until they were 15 or 20 feet in. "I can't believe anyone would really do that here. It's not exactly romantic," she said. "But I guess there's the thrill of being out in public; especially under the bleachers." She looked around and said, "Let's find out!" Suddenly she knelt down and unhooked Corey's belt. "What are you doing?" Corey almost yelled in shock. Olivia looked up at him and smiled. "What do you think I'm doing?" she answered while unbuttoning his pants and unzipping them. "There are people on the track!" Corey cried. "And anyone could walk by", he protested but extended the last word as Olivia started rubbing his dick through his underwear. She ignored him as she pulled down his pants and underwear. She grabbed his dick and gave it a lick from base to tip. "So do you want me to stop?" she asked before sticking the tip of his dick in her mouth and tickling his balls. "No; no; no; please don't stop." "Are you sure?" she asked immediately before sliding her lips down his dick a few inches, stopping before it hit her throat. "Yeah, I'm sure." After fifteen seconds of sliding his dick in and out of her mouth while stroking the part beyond her mouth, she pulled her mouth away. "You sure you're not afraid of us getting caught?" Then she went right back to sucking and stroking. "I don't care about that. Please don't stop." Olivia smiled to herself as she continued sucking on his dick, paying special attention to the part just behind the head. She knew she couldn't take his dick very deep, as she always gagged. And truth be told, she hadn't given a lot of blowjobs. But today, she was really turned on by the thought of doing it outside, under the stands, where they really could get caught. And she liked doing it to Corey. As she continued, Corey started moaning. Corey wanted to touch Olivia somewhere; anywhere; just to make a physical connection while she had his dick in her mouth. But he didn't want to put his hands on her head, as he didn't want her to think he was going to start forcing mouth her further down his dick, like he'd seen in porn videos. So, he just used three fingers of his right hand to run his fingers through her hair on the side of her head. Olivia closed her eyes for a second when she felt him stroke her head. After a couple of minutes, Olivia pulled away for just a second, stroking his entire dick with her hand, as she whispered, "tell me before you cum." Corey grunted acknowledgment and moaned again when his dick went back in her mouth. After another few minutes, Olivia slowly strummed Corey's balls. "Oh, God!" he cried out. After just another minute, Corey desperately, but quietly, roared, "I'm gonna cum!" Olivia pulled his dick out of her mouth and continued stroking his full length, pointing his dick away from her, and continuing to tickle his balls. After five seconds, Corey grunted, and he shot a burst of cum. Olivia could feel the hot liquid move through his dick, and she smiled. As she continued stroking him, he shot four more times, his dick twitching each time. After one more twitch, where nothing came out, Corey let out a long sigh. Corey put his hands around Olivia's shoulders and lifted her up, immediately putting his lips on hers and giving her a passionate kiss. Eventually, he pulled away. "Jesus, Olivia, that was unbelievable!" Suddenly, a light bulb went off, and he remembered he was still standing outside with his pants and underwear around his ankles. "Uh, I'd better get dressed before I get arrested for flashing the world," he said, as Olivia laughed. Once he finished buckling his belt, he looked at Olivia, who was still smiling. "I can't believe you did that," he said. "Oh, sorry," she said. "If you prefer, I'll never do it again." "No, no, no," Corey quickly replied, "I'd Love for you to do it again. I was just kinda surprised you did it here. Out in the open. Where people could have seen us." "Made it exciting, huh?" she asked with a smile. Corey laughed. "It would have been exciting no matter Where you did that! But, yeah, I guess it did add a little extra; something." With a broad smile, Olivia grabbed Corey's left hand with her right hand, intertwining her fingers with his. "Come on. Let's go to my house and see if we can do something exciting there, too." When they got to Olivia's, she led him upstairs to her bedroom. There was a desk with a laptop on it and shelves above filled with books. There was a dresser with a TV and a few pictures. Two large windows faced the front of the house, and the sunlight coming in was bright. When Olivia closed the door, Corey noticed a full-length mirror on the back of the door. And, of course, there was a bed; a queen-size bed with lots of stuffed animals on it. As soon as Olivia closed the door, Corey walked up to her, wrapped his arms around her, and pulled her against him. "Let's see," he said, looking up as if he was thinking. "She's invited me to her room and she's standing. I wonder if she wants to do more than talk," he said, repeating the instructions Olivia had given him two days ago. "Of course I'm standing," she said, laughing. "You didn't give me a chance to move more than two inches from the door." "Ah, you've discovered my secret plan to prevent you from sitting." He placed his lips on hers and started to slowly kiss her. He teased his tongue into her mouth just a bit, and then pulled back. She then repeated the move as they kissed like lovers who had known each other for years. The kiss was passionate, but not rushed or desperate, and each of them let out occasional moans. Corey slipped both hands down to Olivia's butt, squeezing each cheek as he pulled her body against his hard dick. They ground their bodies against each other, and both were incredibly excited. They continued kissing for quite a while, letting the desire build. Then, without breaking the kiss, Corey moved one hand from Olivia's butt to her breast, first squeezing her entire breast and then gently pinching her hard nipple that poked through her top. "Hmm," Olivia moaned as waves of pleasure shot from her nipples through breasts to her entire body. Corey finally broke the kiss and turned Olivia around, so her back was to him, and they were both facing the mirror on the back of the door. Corey watched in the mirror as he ran both hands up Olivia's body and onto her breasts, again squeezing them and then pinching her nipples as he pushed his hard dick against her back. She sighed and closed her eyes. He continued massaging her breasts for a minute before moving his hands behind her neck and untying the bow of her halter top. He pulled the upper portion down until her breasts came into view. Looking into the mirror, Corey got incredibly excited. Olivia's dark red areolas looked incredible against her lighter skin. "Jesus, Olivia, you are so fucking beautiful. I could look at your body all day long." Olivia smiled. She liked the way Corey looked at her and the way he appreciated her less-than-giant breasts. As Corey gently thrust his pelvis into Olivia's butt, he slid his hands up her body and onto those bare breasts he loved so much. He squeezed them both, and they both moaned. He kept his eyes on the mirror as he lowered his head to kiss the side of Olivia's neck while he continued pumping her breasts. Olivia closed her eyes as she moaned. He continued caressing her breasts, occasionally pinching her nipples between his middle finger and his thumb, as he slowly kissed the back of neck, then the other side, then softly sucked on her

11 Aug 2026 - 1 h 0 min
episode Seducing the Shy Guy: Part 2 artwork

Seducing the Shy Guy: Part 2

SEDUCING THE SHY GUY: PART 2. ANOTHER OF HIS SISTER'S FRIENDS WANTS TO "HELP" COREY. BASED ON A POST BY LEADER12 [https://www.literotica.com/authors/Leader12/works/stories], LISTEN TO THE ► PODCAST [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy2.mp3] AT STEAMY STORIES [https://feeds.feedburner.com/steamy-stories]. [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy2.jpg] GINA/ Neither of them moved for five minutes. Finally, Olivia lifted her head and smiled at a smiling Corey. "Hold the end of the condom so it doesn't slip off when I get off of you," Olivia said. After Corey squeezed his hand between them and grabbed the condom, Olivia lifted her body and rolled to the side. "Wrap it in tissue and throw it out; not in the toilet," she said. He got out of bed and followed her instructions. When he came back, Olivia already had her panties and bra on. "Olivia...," he started, but she cut him off. "Don't say anything, Corey. Just listen to me. That was fantastic. You made me feel wonderful. I really liked that. But just because a girl has sex with you, it doesn't mean she's your girlfriend. It doesn't mean anything has changed. It doesn't mean she wants to fuck you again, okay?" Corey nodded, but he was really disappointed. He understood Olivia was telling him this was a one and done. As Olivia continued getting dressed, Corey just watched. When she was done, he had to say something. "Olivia?" She looked at him. "I understood what you said. I won't bug you or get weird with you, okay? I just wanted to say thank you. Not only do I appreciate that you did that, but it was also so much better than I possibly dreamed it would be. And most of that is because it was you. I've always thought you were hottest of Melissa's friends, and I never could have imagined this. So, thank you." Then after a short pause, he said, "Okay, I'm done. I won't bother you anymore." Olivia, who had been staring at him the whole time, broke into a huge smile. She walked over to him and gave him a short kiss on the lips. "You're welcome, Corey. And thank you for saying that. I hope you'll feel a little more comfortable with other girls. Soon, you'll be sleeping with every girl at college." Corey laughed. "Yeah, I don't think so. But a guy can dream." When Olivia got to the door, she opened it and then stopped. She turned back toward Corey. "Corey?" "Yeah?" he said, obviously sorry that this was over. "It's good that you understand this doesn't mean we're going to do it again. But; it doesn't mean we CAN'T do it again. So, if you want to, you can come over to my house Wednesday morning, and we can fuck some more. But it's okay if you don't want to; I won't keep bugging you." She forced herself to feign a sad look as if she was worried Corey would say no. Corey's eyes popped open. He couldn't believe what Olivia just said. "Really?" he asked. "Uh huh," she said with a big smile. "Oh, yeah! Thanks, Olivia! I'd like that." Olivia flashed him a big smile. "Okay. See you Wednesday. Bye." Just as Olivia was about to walk out the front door of the house, she started laughing when, from the other end of the house, she heard Corey yell, "Holy Mother fuck!" For ten minutes after Olivia left, Corey just lay on his bed with a shit-eating grin, staring at the ceiling. He couldn't believe he had just had sex with her. OLIVIA! A girl he fantasized about. And he couldn't believe she had invited him to come to her house in two days to continue the fun. The rest of the afternoon, he spent a lot of time on the internet. He wanted to be ready for Olivia on Wednesday. He wanted to do whatever he could to make her feel really good. He knew what he wanted to do, and he wanted to make sure he was doing it right. He wanted to make sure he knew how to give her an orgasm when he went down on her. Of course, the internet can be a wonderful source of information; especially when half the information contradicts the other half. When Corey was reading articles with titles like, "How to Eat Pussy" or "What Women Want When You Go Down on Them", he found some information that seemed to be consistent; but not always. One article said, "Draw the letters of the alphabet with your tongue on her clit." Another said, "Whatever you do, don't draw the letters of the alphabet with your tongue on her clit." But Corey looked for those techniques that seemed to pop up consistently on multiple pages, and he had a good idea; at least in his head; of what he wanted to do when he got the chance. That night, his dad grilled chicken breasts, his mom made a salad and some side dishes, and they all sat around the kitchen table eating, laughing, and teasing each other. On his first long break after his first semester at college, this family time made him happy. That night, Melissa came into his room again. As usual, she sat on his bed. "You seemed really happy tonight. Something happen today?" she asked. For half a second, Corey wondered if Melissa knew. But her facial expression made him believe it was a legitimate question, with Melissa just being herself and caring about Corey. "Nah, I'm just happy to have the stress of finals in the rear-view mirror. It's nice to have family meals again." "Yeah, I know what you mean," Melissa said. "As much fun as it can be at college, I sometimes miss the four of us just laughing with each other. It reminds me of when we were kids." Corey smiled. He felt the same way. And for some reason, thinking about this made him get a little choked up. "You know, I love you, Melissa." Melissa seemed surprised by the statement. She wasn't surprised he loved her; she was surprised he said it. But then she flashed back to dinner with everyone tonight and thought about when they were younger, and she got a little emotional, too. She got on her knees and leaned into Corey to hug him. "I love you too, Corey," she said as she squeezed him tight. Corey held her as tight as she held him. For a couple of seconds, he only thought about his love for his sister. But then, he thought about the feeling of her breasts smashing against his chest. And it felt good. Corey never thought about Melissa in a sexual way. Of course, he thought she was beautiful, and he thought she had a great body. EVERYONE thought that. But feeling her bra-less breasts push against him was different. Maybe it was because of what happened today. But whatever it was, he realized he shouldn't be thinking about her that way. He quickly released her and looked at her. "Stop that or you're going to make me cry," he said, causing Melissa to laugh. Melissa got up and walked toward the door. "Goodnight," she said. "Goodnight," he replied. After he finished a little browsing on his phone, Corey set it down and turned off the light. He grabbed some Kleenex and pulled his pajamas down. He closed his eyes and pictured Olivia's naked body as he stroked his dick. He re-lived the activity from earlier in the day. He imagined he was touching Olivia's breasts and pinching her nipples. He remembered when Olivia stroked his dick. He started stroking faster as he pictured the moment when he slipped his dick into her. He had fantasized about Olivia in the past, but now he didn't have to imagine what her naked body looked like. Now, he pictured the real thing as he imagined his dick sliding in and out of her faster and faster as he stroked himself faster and faster, until he exploded into the Kleenex, grunting with each spurt. When he finished, he threw the Kleenex toward the waste basket, not sure where it landed but not caring. He pulled up his pajamas and quickly fell asleep; with a smile on his face. The next morning, Corey was sitting on the couch streaming a video when Melissa walked past. "I'm heading out to help Olivia find a dress for her cousin's wedding, and then we're going to lunch. I'll see you later." "Okay. Bye." Half an hour later, the doorbell rang. When Corey opened it, he was surprised to see Gina, another of Melissa's friends. "Hi, Corey," she said with a big smile. "Hi, Gina. Melissa's not here." "I know," she replied. "She's dress shopping with Olivia. I left my sunglasses in her room yesterday. Okay if I get them?" "Yeah, sure," he replied, as he went back to the couch to watch the video. As Gina walked by, Corey couldn't help but notice how good her ass looked. She was wearing light gray yoga pants, and each round cheek was separately staring at him, with her crack clearly defined. He smiled as she disappeared around the corner, and he returned to his video. Gina went to Melissa's room, sat on the bed, and smiled to herself as she started browsing her phone. She didn't need to look for her sunglasses; she had worn them as she drove to Corey's house and left them in the car. The lost sunglasses was just the excuse for coming over. She was there because of Corey. After what Melissa said yesterday, Gina thought it would be fun to be Corey's first. After five minutes, Corey heard Gina call. "Hey, Corey, can you come here, please?" Corey turned off the video and walked upstairs. Gina was standing in the hallway outside his bedroom. "Can I talk to you?" she asked. "Uh, sure," he said, a little confused. He was even more confused when Gina walked into his room. He followed her in, and then she went back to close the door. She walked over to where Corey was standing. "Can I ask you a question?" she said. "Sure," he replied, almost making his reply sound like a question. He was still very confused. Gina put her hands on his waist, confusing him even more. "Melissa said you're still kinda' shy when you're around girls." As much as he loved Melissa, Corey was again pissed at her for mentioning this to her girlfriends. "You know," she continued, "you really shouldn't be. You're smart, you're interesting, and I hope you know you're a good-looking guy. Any girl would probably want to kiss you." Corey was still thinking about being mad at Melissa, and it took him a second to process what Gina said. All of a sudden, he stopped thinking about Melissa and was thinking about what Olivia said yesterday. "If she invites you to her room and she remains standing instead of sitting, it probably means she wants to kiss you," Olivia had said. And did Gina really say, "any girl would want to kiss you"? Corey quickly analyzed the situation. "Yeah?" Corey said. "You think Any girl would like to kiss me?" "Oh, yeah," Gina said with a grin, "I'm sure they would." Corey hesitated for just a second, thinking it was possible he was about to get slapped. But then he moved his head toward Gina's, tilting it so that it was obvious what he was about to do. Instead of getting slapped, Corey was happy to see Gina tilt her head in the opposite direction and place her lips on his. After a short few seconds, Gina opened her mouth. Corey followed suit and gently moved his tongue toward Gina's mouth, where it was met halfway by her own tongue. They slowly, but passionately kissed for quite a few minutes, and Corey was very excited. He tried to remember everything Olivia had said, as he wanted to see how far Gina wanted to go. "Gently touch the side of her breast," he said to himself. But just as he started to move his hand, he mentally slapped it down. "No, goddammit, not yet!" he mentally berated himself. "First her ass." He slid both of his hands down onto Gina's butt, and it felt incredible. Her yoga pants were so thin, he felt like he was almost touching her bare ass. When he squeezed it, it felt soft on the outside but was clearly firm deeper down. Gina continued kissing him with no objection, so Corey pulled her butt against him, pressing her body against his hard dick. "Hmm," Gina groaned without breaking the kiss. Corey took this as a good sign, and he continued squeezing her ass and grinding against her as their kissing got even more heated. Gina started grinding on her own power. After five or more minutes, Corey was ready for the next step. He thought this was dangerous, as it was a big step from kissing and touching her butt. But he was very excited and figured he had to try. So, he took one hand off her butt and moved it back to the side of her waist. Then he slowly moved it up the side of her torso. Gina's breasts were bigger than Olivia's, so even with his hand just on the side, his entire hand was clearly touching the side of her breast. Not only did Gina not object, but she let out another soft moan. Arguing with himself for a couple of seconds, trying to decide if he could really do what he was thinking, he finally slid his hand totally onto the front of her breast and gave a gentle squeeze. He couldn't believe he really had his hand on Gina's breast, and he was waiting for Gina to push him away and ask him what the hell he was doing. But without breaking the kiss, Gina let out another soft "Hmm". They continued kissing while Corey squeezed Gina's breast over and over. Her breasts were much bigger than Olivia's, and Corey realized that his hand didn't come anywhere close to covering the whole thing. He was still rubbing his dick against her and thought everything was going really well until, he thought, Gina finally came to her senses, breaking the kiss and stepping away from him. Corey was ready to apologize for everything he did when Gina suddenly pulled her top off and threw it toward a chair. Then she reached behind her back and unhooked her bra, taking it off and throwing it toward the same chair. Corey stared in shock. Although fairly large, her breasts had no sag whatsoever. The were perfectly round with fairly large, pink areola Her nipples were thick and very hard. "Oh God!" Corey sighed as he saw her breasts. Gina smiled. "You like these, Corey?" she asked, cupping the bottom of each one. "Who wouldn't? They're incredible!" Corey Did think Gina's breasts were incredible, and he loved looking at them, but he actually thought Olivia's small breasts were even sexier. But he cleverly decided not to mention that to Gina. After another two seconds of staring, Corey put one hand on her left breast and put his mouth on her right nipple, flicking his tongue over it quickly. "Oh, yeah, Corey, that's good," Gina said, as she put her hands on the back of Corey's head. As he continued flicking his tongue, his hand gently pinched her nipple. "Hmm. Pinch it harder! I like that." Corey complied, pinching her nipple even harder. Her moans let him know it wasn't too hard. Without releasing his hand, he moved his mouth to her lips, and they kissed passionately. They were grinding against each other, and both were breathing quickly. Gina slipped a hand between them and rubbed up and down Corey's hard dick. "I want this in me," she whispered as she pulled her head away from Corey. She grabbed the bottom of his T-shirt, and they both pulled it off. Gina unbuckled Corey's belt, unhooked his pants, and pulled down his zipper. She slipped her hand inside and rubbed his dick over his boxer-briefs, causing him to moan. He stepped back and pushed his shorts to the floor, kicking off his shoes and his shorts. Then he took off his socks. Gina was watching him and then started to peel off her yoga pants. Corey put his hands on hers to stop her. "Can I do it, please?" he asked. Gina smiled and nodded. He gave a quick kiss and suck on each nipple before he knelt on the floor. He kissed Gina's mound through her pants. Then he put one hand in the waistband on each side and slowly pulled them down. When her thong came into view, Corey again kissed her mound. He finally got the pants all the way down. Gina held on to Corey's head as she lifted each foot and Corey removed her sandals and pants. He slowly kissed her inner thigh higher and higher until he ran out of room. He put his fingers in her panties and slowly pulled them down. When her bald mound came into view, Core

10 Aug 2026 - 1 h 0 min
episode Seducing the Shy Guy: Part 1 artwork

Seducing the Shy Guy: Part 1

SEDUCING THE SHY GUY: PART 1. HIS SISTER'S FRIEND OLIVIA; TRIES TO TEACH THE ROPES TO SHY COREY. BASED ON A POST BY LEADER12 [https://www.literotica.com/authors/Leader12/works/stories], LISTEN TO THE ► PODCAST [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy1.mp3] AT STEAMY STORIES [https://feeds.feedburner.com/steamy-stories]. [https://archive.org/download/spring-erotic-stories/SeducingTheShyGuy1.jpg] Corey was happy the semester was finally over. His first term at college was fun, but it was challenging. He found high school to be pretty easy, even though he took honors classes; and then AP classes; in math and science. But when he got to college; where lots of people were as smart as he was; he had to work a lot harder to keep up with the pace. He was also taking advanced classes as a freshman because he had received some college credit from his AP classes. The funny thing about it was that he Liked the challenge. He especially liked the advanced Physics class he was taking, since it gave a scientific explanation of things everyone experiences in the world every day. And he liked the challenge of proving he could do the work. He always loved JF Kays speech about going to the moon, when he said, "we choose to go to the moon not because it is easy but because it is hard." Whenever Corey repeated the line, he always dropped the 'R' on the last word and did a terrible job of trying to replicate JF Kays Boston accent, pronouncing the last word "h a h d". But now he could relax for a few weeks during Christmas break. He lived less than two hours away, and his parents texted to say they'd be at the dorm in fifteen minutes. When their car pulled up, Corey walked outside, rolling one suitcase with some clothes. He was surprised when the back door opened, and his sister, Melissa, stepped out. Suddenly he had a huge smile on his face. "Melissa!" he yelled. "I didn't think you were back yet." Melissa was two years older than Corey and went to a different college. She had told him she'd be home the day after him. "I wanted to surprise you," she said, just before the two embraced. "Good to see you, Corey!" The two siblings were always very close even though they were, in some respects, very different. Corey was generally quiet, shy, and uncomfortable in groups of people who weren't his friends. Melissa, on the other hand, could show up on another planet at a party with aliens, and within ten minutes, she'd know all the aliens' names, and they'd all love her. She was very popular in high school; he was not. She dated a lot in high school; he did not. Corey looked up to his sister in many ways. Even though she was beautiful and very popular, she was very down-to-earth. Some of the other pretty, popular girls in high school were real snobs. They wouldn't even consider talking to a nerd like Corey. But Melissa was friends with everyone. She had some friends from the Pom Squad, some friends from her honor classes (some of whom were a little nerdy, like Corey), and random friends she had just made over the years. When some of her "popular" friends made bitchy comments about someone; especially about "nerdy guys"; Melissa would call them out. Corey wasn't sure if she was explicitly trying to defend him or just not tolerating someone being a jerk. But it always made him respect her even more when she'd go against the crowd and defend people. As they drove home, everyone asked Corey about finals. Corey caught up with Melissa, since they didn't talk a lot the prior week when they were both studying for finals. On the way home, they stopped for lunch. Corey smiled when they were all piled into a booth, with Melissa next to him and his parents on the other side. It reminded him of his childhood, when they'd go out as a family and laugh and make fun of each other. He had friends who had older sisters, but none of them got along like he and Melissa did. He always appreciated Melissa; probably more than she realized. That night, after everyone got ready for bed, Corey was sitting up in his bed surfing the web on his phone when he heard a knock on his door. "Come in," he yelled. Melissa walked in wearing a t-shirt and shorts, her standard sleeping outfit. She sat on Corey's bed and started asking more questions about his first semester. Once again, Corey smiled to himself as this was another event that reminded him of his childhood. Melissa would often plop on his bed to talk to him about everything and anything. When he started middle school, and then high school, she also tried to give him pep talks about girls. He was obviously very shy and didn't date in high school, and Melissa always tried to convince him that girls would like him if he just tried. So, he wasn't surprised when Melissa finally got around to asking if he had gone out with any girls. When he said he hadn't, Melissa again turned into his personal life coach and biggest cheer leader, telling him he didn't realize that he's a good-looking guy and that any girl would like him if he just talked to them. While he appreciated Melissa's concern and confidence in him, this was not one of the conversations he enjoyed. Like when he was in high school, Melissa left a little frustrated and definitely feeling sad for her brother. ON the following Monday, Melissa had a few of her high school friends over. They were sitting outside, just catching up on everyone's last semester. One of the girls asked about Corey and how he liked college. Melissa let them know he was doing well, but she briefly mentioned that he's still as shy as he ever was. She told them she felt bad he didn't have the confidence to talk to girls. As soon as she heard that, Olivia smiled to herself. Back in high school, she was Exactly like Corey. She was shy around boys and didn't think they were interested in her. It didn't help that some of her friends; including Melissa; were absolutely beautiful. Some of the cheerleaders had big, curly blond hair, big boobs, and big personalities. They knew how to do their hair and apply makeup; a little too much, in Olivia's opinion; to look like movie stars. Olivia had a thinner body, full B-cup breasts, and stick-straight, pitch-black hair that went halfway down her back. She had big, brown eyes which many would find to be alluring. But she just didn't understand how attractive she was. She was still uncomfortable around boys when she left for college, but her freshman year roommate fixed that. She was a year older, and she told Olivia she was making it "her personal project" to help Olivia come out of her shell. She was fine around girls; she only got nervous around guys. So, her roommate dragged her to every party she went to and forced her into situations where she had to talk to guys. It was a very painful couple of months before she finally found a guy whom she found easy to talk to. She also thought he was hot, and he ended up being the one to take her virginity. Once she got "over the hump", the damn broke. She suddenly realized she Could talk to guys, that some guys thought she was hot, and sex was fun! She felt bad for Corey; she remembered how miserable she was before her "awakening". She was jolted out of her thoughts when she heard, "Hello! Earth to Olivia. Are you there?" "Huh?" she asked, realizing the other girls were looking at her. "I said we were going to go out for lunch and then go to the mall," Melissa said. "Are you good with that?" "Actually, I'm not feeling great. I think I'm going to head home. I'll catch up with you guys later." "You sure?" Melissa asked. "Are you okay?" "Yeah, I just didn't sleep well last night, and I'm kinda' tired," Olivia responded. "Okay," Melissa said, we're going to head out. "Okay. I'm gonna go say hi to Corey and then leave," Olivia said. As the other girls headed out, Olivia went inside and up the stairs. She had been in Melissa's house a million times, so she felt quite comfortable being there without her. When she got to Corey's room, she knocked. "Come in," she heard. She opened the door, and Corey was sitting at his desk where he had been looking through email. He turned when the door opened, and he smiled. He always liked Olivia. "Hi, Corey," she said with a smile. "Hey, Olivia. How ya' doing?" "I'm good," she said. "How about you?" "No complaints," Corey said. They chatted for a little while before Olivia said, "Melissa said you haven't done much dating at school." Corey looked embarrassed and was a little pissed at his sister. "Why would she tell you that?" he asked. "It just came out when someone asked how you were doing. Nothing to be upset about," she said. "It's just not easy;" he said, with his voice trailing off. "You know," Olivia said, "I used to be the same way. You know how shy I was." "Yeah, I suppose." "But my roommate really forced me into situations where I'd Have to talk to guys, and eventually it wasn't so hard. Hey, I've got an idea. Come here." "What?" he asked, given they were already in the same room. "I said stand up. Now!" she said with a laugh. Corey got up and walked toward her. She walked into the hallway, outside his room, and then stopped. He followed her. "Okay, let's pretend we're at a party and there's some music playing." Corey laughed. "Seriously? Pretend we're at a party?" "Shut up and listen to me. Yes, pretend we're at a party." "Oh, okay," Corey said in the most sarcastic voice possible. "I'm at a party." "Okay," Olivia continued, "now pretend you see me, and you think I'm hot." "Well, that doesn't take any pretending," he said. Olivia pulled her head back with a shocked look. "You think I'm hot?" Now Corey was embarrassed and looked down. "Well, of course I think you're hot. Who wouldn't?" Olivia was still surprised, but she ignored the comment for now. "Okay, so;" Then she moved a few feet down the hallway. "So, you decide to come talk to me." Corey looked at her. "Let's go Corey. Remember? You think I'm hot, so you come over to talk to me. Come here." Corey walked the few feet to where Olivia was leaning against the wall. "Hi, I'm Olivia," she says. Corey looks at her as if she's crazy, but when Olivia raises her eyebrows and holds her arms up with her palms up in a "your turn" gesture, Corey finally goes, "Oh, hi. I'm Corey." "Hey, look at that," Olivia says, "you're talking to a girl." "So, do you like this music?" Olivia asks. Corey finally decides to play the game. "Yeah, they're not too bad." "Have you seen many bands on campus," she asks. Without thinking too much, Corey replies, talking about some bands he's seen. "See," Olivia said. "Once you get going, it's not so bad. Now, if the girl is smiling at you a lot or maybe putting her hand on your arms when she's talking, like this;" and she places her hands on Corey's upper arm, "then it means she's into you and wants to keep talking. But after a while, maybe she says, 'It's kind of loud here. You wanna go talk in my room?' That's a good sign." Olivia puts her hand on Corey's arm and leans into him as she says, "It's kind of loud here. You wanna go talk in my room?" Corey chuckles and says, "Yeah, sure." Olivia grabs his hand in hers and walks the three feet to Corey's room and pulls him inside. She closes the door and locks it. "So, if she invites you to her room, it probably means she likes you and wants to get to know you better. Maybe she wants to make out. If she doesn't immediately go and sit down but is standing, walk up to her and put your hands on her waist, like this." Olivia put her hands on his waist, but Corey left his hanging down. "Hey," she said, "are you listening?" she said with a little chuckle. "We just came to my room, and I didn't sit down. Put your hands on my waist like this." Corey smiled. He didn't know why Olivia wanted to play this game, but he didn't want her to get mad at him. So, he put his hands on her waist. "So, if you get this far, she definitely wants to at least kiss you," Olivia said. "You should lean in and give her your best kiss." Corey nodded, as if he understood. After a couple of seconds, Olivia said, "I'm waiting." "Huh?" "I said, you should lean in and give this hot girl a kiss." Suddenly Corey realized Olivia really expected him to do this. Now. Here. With her. He wasn't sure why, but he thought he'd better do something. He leaned his head forward about an inch. Olivia smiled to herself but was happy he moved at all. She figured she'd better show him. She leaned forward, closed her eyes, and placed her lips on his. Corey didn't move at first, but, finally, he realized she was serious. So, he started kissing her. He couldn't believe this was happening. He had kissed a few girls, but nobody as hot as Olivia. His sister's friend. When Olivia opened her mouth, Corey did the same. When he felt her tongue enter his mouth, he moved his hands behind Olivia's waist and pulled her against him just a bit as they enjoyed a passionate kiss. Olivia was surprised he pulled her against him, and she could tell he was getting hard. She liked the feeling. A lot. And she started getting excited, herself. After five minutes of wonderful kissing, Olivia pulled her head back and smiled. "That was nice, Corey. Real nice." Corey just looked at her quietly with a smile on his face. "So obviously she likes making out, but now you have to figure out if she's interested in something more. You're in her room; by the way," she said, looking around as if to take in the whole room, "do you like the way I decorated my room?" Corey looked around and smiled. "Yes, I do. It's very nice. We seem to have similar tastes." "So, now it gets even more fun. If you're in her room and she's been kissing you, she might want more. But you've got to go slowly, because you can't assume anything. If you do something and she stops you or says no, that's okay. That just means she's not ready for it yet. So go back to kissing her. From my long-term experience kissing you, she'll like more of that." They both smiled. "So, something you can do that lets her know you're interested in a little more without freaking her out is when you're kissing her, move one of your hands onto her ass and give it some gentle squeezes. If she doesn't object, keep your hand there and pull her against you. If she says 'uh-uh' or moves your hand off her butt, that's fine. Just move your hand back to her waist and keep kissing. Let's try that." Corey tried to process what he heard. Did she really say, "let's try that"? When Olivia started moving her head forward, Corey leaned forward, and they started kissing again. Not believing he was really doing this, he slid one hand down onto Olivia's ass and gave it a little squeeze. It felt incredible. Olivia softly moaned and Corey pulled her against him. She started rubbing her pelvis a little bit against Corey's hard dick, and he let out his own groan. They continued kissing and Corey continued squeezing Olivia's ass, and they were both very excited. After another ten minutes, Olivia again pulled her head away from him, but he left his hand on her ass. "Hmm," she said, "you're very good at this. You must be very experienced." This made Corey laugh. "You should be feeling pretty good about how it's going with your hot friend by now," she said, smiling at calling herself a 'hot friend'. "So now you need to take the next step, again being subtle to let her bow out gracefully if she wants to. So, keeping the one hand on her butt, slide your other hand up her side." Corey did as instructed. His hand was getting dangerously close to Olivia's breast.

9 Aug 2026 - 1 h 0 min
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