Nathan & Cass Ch. 02

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Nate and Cass decide to go all the way.
4.3k words
4.64
15.1k
3

Part 2 of the 2 part series

Updated 11/01/2022
Created 07/03/2013
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(This is part 2 of Cass and Nathan's story. Though this story will make sense and stands alone without part 1, I think that it would be better enjoyed after reading part 1 Whatever you decide, I hope you enjoy!)

May I, Please?

I have lived in Seattle for 2 years now. I'm a third year college student, trying to get my bachelor's degree in physics. My life had always been pretty simple, but that was before I met Cass. We met in the apartment building I still live in, the summer before my freshman year. She and I became friends after a chance meeting in the laundry room.

But to truly understand our story, we'll have to go back a couple of years, to a night in the Fall of my freshman year..

It was the second week of classes and life was a bit hectic. I didn't have many friends yet, aside from the hot, insatiable 18 year old girl that used to live upstairs. We'd had one hot steamy night a month and a half ago, in which she masturbated in front of me, and had her very first orgasm. If that wasn't enough to keep a guy interested, I don't know what was.

It was a cold, rainy, Friday night – in other words a typical Seattle night. Anyway, I was coming home from studying in the library, drenched in rain and completely exhausted. I walked over to the elevator and punched the button to go upstairs. I heard the familiar ding, and waited, somewhat impatiently. I clambered into the elevator and punched the number 9 for my floor. "Finally," I thought. "Warmth and comfort and a bed."

The elevator stopped at my floor, and I exited and walked to my door.

The room was a bit chilly when I entered, but still as comfortable as I'd left it 15 hours ago. I stripped down to my boxers and climbed into my bed. Thoughts of my gorgeous neighbor flooded my mind. She was unbelievable. She had the darkest hair I'd ever seen naturally on a girl that pale. She wore it long and curly, and it always smelled of fresh flowers. Her name was Cassidy, or Cass, as she preferred to be called.

She'd moved out of her apartment 2 days before classes started to live in a dorm. I hadn't seen much of her in the past three weeks because between packing and moving and adjusting to campus life, she'd been busy. I'd called her a few times, but had gotten the feeling she was avoiding me.

I lay staring up at my ceiling, suddenly unable to sleep. Cass and I had developed a "friends with benefits" relationship over the summer but we hadn't gone farther than mutual masturbation and making out. The closest I had got to touching her during one of our sessions was the first night when I told her to get on all fours and spread her ass so that I could blow my load all over her asshole. My dick stirred in my pants at the memory.

I leaned over the bed and onto the floor and dragged the pants I'd just removed closer to the bed, so I could grab my cell phone. I debated texting Cass, to see if she wanted to come over, but that sounded cheap. Maybe I could see if she wanted to hang out tomorrow. "Blah." I said aloud.

Giving up, I tossed my phone onto the pillow next to me and tried to sleep.

I awoke at 3:00AM, to the sound of my doorbell. I pulled a shirt over my head and stumbled to the door. I opened it to the sight of a short, petite, black haired girl. Cass. She was dressed in tight pajama pants and a white thin strap tank top, and she was completely drenched. I could see her perfect nipples through the thin fabric of the shirt. I felt a jerk in my boxers and tried to stand in a different position, to mask it.

She smiled as I yawned and said "Sorry to wake you.. I couldn't sleep.. You wouldn't believe the sound the rain makes on those old dorm roofs."

I waved her in and closed the door. "Don't you own an umbrella, Cass? You're completely soaked. Let me get you some warm clothes."

I walked into my room and grabbed a white undershirt and a pair of my basketball shorts. I stepped out of my room to find Cass shivering in the middle of my living room. I handed her the clothes and she put them on. They swallowed her whole, of course.

"Do you want to come lay in my bed? I'm kind of beat."

She smiled and said "Sure."

I stripped off the shirt I'd put on to answer the door and flopped down on the bed, and she lay beside me. I didn't know what the protocol was here. Did I hold her? Did we make out? I decided to let her call the shots. A minute or so later, Cass had scooted over and laid her head on my chest and had begun to lazily trace her fingers over the hair on my stomach.

She kissed my chest and slowly inched her hand lower, until she found the waistband of my boxers. She tugged them gently, and I lifted my hips and obliged. Her hand found my cock almost immediately, and started massaging it, slowly. By now, I was almost completely hard, which is how I usually responded to a few moments like this with Cass.

I didn't know what she was playing at. We'd never actually been like this, together in a bed. Most of our encounters had been on the couch in my living room, and even then, we'd just masturbate together, or simply make out.

She got out of bed and slid her shorts down, revealing a black and white polka dot thong. She slid into bed next to me, but instead of lying back down on her side, she slid her thigh over my crotch and sat down on my lap. What was she doing? We had never gone this far. I tried to remain calm.

"Cass..." I started, but she put her hand to her mouth and said "shhhh," and smiled.

She started grinding her pelvis on my cock and I could feel that she was already wet through her thong. God, that felt good. I wanted to rip that small piece of fabric off her perfect little ass and take her right here. It took everything I had in my body to just lay perfectly still and see what her endgame was. She pulled the shirt over her head and her perky naked breasts bounced in my face.

I slid my hands to her hips, with my fingertips grasping her ass, and she leaned forward to kiss me. Her tongue tasted like warm cherries. It was intoxicating. She put her hands on my chest and grinned malevolently, then brought her mouth down to my stomach and began kissing, leaving a trail from my abdomen to my chest. She traced the tip of her tongue up to my neck, and I could barely contain myself. My grip on her ass tightened, and she let out a soft giggle. She stopped and I felt her breath, quick and hectic, close to my ear.

"Do you want me, Nathan?"

She moaned her familiar moan, while I grunted and tightened my grip on her tight little ass. The only syllables I was able to form were guttural, but I somehow managed to choke out "yes."

She shook her head and bit my earlobe. She plopped herself down beside me, pulled the comforter over us both, turned her ass towards me and fell asleep.

As much as I liked this girl, all that was running through my head right now was "fucking cock tease." I went to my bathroom to finish myself off, then came back to bed and fell asleep.

***

The next morning, Cass played coy and innocent, and said she had to go to the library to do homework, and she'd be back over that afternoon.

I busied myself all day with cleaning around the apartment, taking a shower, and catching up on reading for my intro to ethics class. At 5:30, I heard a knock at my door. I answered it to find Cass, standing in tight white shorts that barely covered her ass, a tight black thin strapped tank top, knee high multicolored striped socks, and black sneakers. Her hair was misty and frizzy from the weather out. She was holding a pizza and two restaurant cups of soda. She grinned when she saw me practically ogling her cleavage.

"Are you going to invite me in?" she asked, playfully.

I moved to one side and allowed her in.

"Aren't you cold in that?" I asked.

"Not really, I'm used to Rhode Island winters, and this doesn't even compare."

She plopped down on the couch, kicked off her shoes, and took a slice of pizza. "Want one?" She held out one for me.

I took the pizza from her and chewed slowly, wondering how this night was going to go. I sat down beside her and this seemed to be an invitation for her to climb into my lap. God, I hoped she didn't get me hot and bothered and then just stop and go to sleep.

We started making out few minutes later and she tossed her top behind my couch. I smoothed my hands across her naked breasts and cupped them firmly in my palms. I could hear her breath quicken and her kisses became slightly more urgent, but I didn't reciprocate; tonight I wanted to call the shots. I gently pinched her left nipple between my thumb and forefinger and she pulled her mouth away from mine and moaned. I bent my head down and pulled the other nipple into my mouth and sucked on it and felt her hand reach up to my head and grab a handful of my hair.

I licked a trail from her tits to her throat and felt her grinding against my cock. It was rock solid by now. I knew Cass's weaknesses. She liked to be controlled 99% of the time, and I knew just how to do it.

I slid my fingertips gently up and down her back, while kissing and sucking and tugging on her breasts with my mouth. She moaned loudly and leaned closer into me. It took all I had in me to be patient and take it slow, because I was still unsure of how far she wanted to take this, and I wanted to make sure I teased and tortured her properly for what she'd done last night.

She whimpered into my ear and pulled her body closer to me, her crotch pressing against my abdomen. I placed my hand on her hip and firmly but slowly moved her back to where she'd been sitting a few moments ago, and heard her whimper as her pussy came in contact with my cock. She stood from my lap, pushed down her shorts and white thong, and disappeared into my room. I quickly discarded all of my clothing and followed her.

I found her lying in the middle of my bed, quickly stroking her clit. I immediately removed her hand and said "you know better than that, Cass.."

She looked at me challengingly and said

"What are you going to do? Punish me?" and smiled. I spread her legs and began rubbing her clit with my index finger.

She arched her back and moaned, "Please, Nathan, don't stop." I stopped and pulled my hand away and closed her thighs, grinning. She wasn't going to get away with showing up at dawn and teasing me like she did.

She moved her hand to her clit and I pulled it away, above her head, and moved my body so it was positioned directly above her. I could feel my cock poking the top of her clit. She looked me in the eye; apparently she hadn't been expecting this. I stayed still, in case I'd gone too far, and let her make the next move. She bent her head up to kiss me, and positioned her thighs so they were around my hips. My cock slid further down her pussy, and I angled my hips backward to keep from entering her.

I moved my hand between her thighs and found her clit and started stroking it in soft circles. Her breath quickened and then caught in her throat. I removed my hand and heard her sigh, exasperatedly. I chuckled. I rolled off of her and plopped down onto the bed beside her.

She raised her head and said "what? Is that it?" looking harassed.

I crossed the room over to my dresser, opened the top drawer, pulled a condom from between some socks, and tossed it on the bed.

Cass looked up at me, innocently. I crossed my arms, leaning against my door and said,

"Do I need that?"

I was prepared to give Cass whatever she wanted, even if she only wanted to masturbate while I watched. Apparently the only time she was ever able to get off was when I took control and told her how to please herself. I desperately wanted to be buried inside of her, and though she loved to be ordered around, I knew that this was a time to let her be in charge. At least until she decided what she wanted.

She picked up the condom and toyed with it between her fingers, contemplating what I had just asked her. She shifted on my bed and said,

"I don't know, do you need it?" Grinning.

I resisted the urge to groan. "This isn't a decision I get to make, Cassidy. We can fool around in my bed with you flicking with your clit or fucking yourself with whatever dildo we have on hand, but this.. this is different. I can't force you do anything.. Not if I'm actually going to be a part of it. " I said.

She met my eyes and I can tell there was a burning desire deep within her. The grin left her face and she tossed the condom to her right and slid directly in the middle of the bed into a sitting position. I held my breath, wondering where we went from here.

She looked up at me, her aquamarine eyes full of desire and simply said, "You need it."

It took all I had in me not to dive into my bed and ravage her right then. I slowly walked to the bed and sat to her right, leaning in to kiss her full on the mouth. I dragged my hand gradually across her abdomen and rested my hand on her left hipbone. She shifted impatiently in my bed and I could tell that she wanted me to dive right in, as it were.

I didn't want to rush this. I wanted to savor every moment because the opportunity might not come around ever again.

I slid my hand deliberately down her thigh, this time resting it gently on her pussy. Her breath caught and she raised her hips, wanting more. I used my index finger to trace her outer lips gently as she writhed, clearly getting even more impatient with my chosen pace. I let my finger slip into her folds and found her clit. She moaned loudly this time and her hand made contact with my back.

I traced soft circles on her clit until her thighs became rigid and she arched her back, then I stopped. I knew that she was close to cumming but I wanted to drag it out a bit longer. She looked up at me, clearly disappointed, but didn't speak. I fumbled around for the condom and tore it open, rolling it onto my aching cock. I slid in between Cass's thighs and rested the head of my cock just above her clit.

Taking one nipple into her mouth I massaged the other with my fingers, alternating between pinching, pulling, and gently tracing its outline. Cass moaned and wrapped her thighs around my hips. I trailed kisses from her breastbone to her left ear, nibbling on her earlobe. I pressed my lips against her ear and breathed, "Do you want it?"

Her grip on my hips tightened and she moaned, "Yes."

I leaned forward and rested my hands on either side of her head preparing to shove my cock deep into her pussy but realized that something didn't feel right. I rolled to the side of the bed and stood up, trying to shake the feeling. Before Cass recognized what happened I quickly said, "This bed is uncomfortable. Let's move to our usual spot on the couch."

I grabbed lube from my dresser and she obliged by following me into the living room. I sat down in the middle of the couch and spread my legs wide. Without instruction she sat in my lap facing me, her huge tits on either side of my face. She roughly thrust against me and my cock was dangerously close to sliding inside her but I was beyond caring about making it last at this point. She leaned forward placing my cock onto her clit. A moan escaped my lips as I squeezed her ass with my left hand. Quickly and deliberately Cass thrust toward my hips and my cock slid deep into her pussy at last. Her tight pussy felt amazing as it began sliding up and down the shaft of my pulsating cock. I squeezed her ass tighter as her pace quickened. Her tits bounced furiously in my face and I knew I wouldn't last long at this pace but I was far too deep into pleasure to tell her to slow down. I used my right hand to locate her clit and began flicking my thumbnail quickly over it. I heard "Oh god," from above my head and knew I had found the right spot.

Her pace had slowed slightly but I knew that I wouldn't last five more minutes, if that. Her pussy was so wet and soft. My thumbnail flicked faster and Cass moaned, "Ohh, please. Don't stop."

I slapped her ass with my left hand while continuing to pleasure her with my thumb. She arched her back, thrusting harder onto my cock and making her swollen clit more visible. I could tell that in a few seconds more she'd reach her orgasm. I slapped her ass again and slowed my pace on her clit practically to a halt. She half panted half moaned, "No! Don't stop!"

I slapped her ass much harder this time and said, "Don't tell me what to do. I'll decide when you get to cum and if you argue I will drag it out much longer."

She looked angry and thrust harder against me. Taking control of her orgasm had effectively calmed me and I knew I would last a bit longer. I ignored her clit for several minutes and instead focused on slapping her ass. Each slap caused Cass to arch her back and moan loudly. God she turned me on so fucking much. I popped open the lid to the lube with my right hand and recklessly squeezed a bit into my fingers. I felt around to her ass and rubbed the lube there. I spanked her a few more times before stroking my fingers at the top of her crack. I traced down and slowly began petting between her cheeks. I rubbed her asshole in the same soft circles as I'd rubbed her clit in before as I watched her squirm. She arched her back farther this time and reached up to squeeze her right tit. I dragged my finger up and down slowly between her cheeks with my right hand and slapped her ass again with my left. I reached again for the lube and squeezed more out onto my fingers. Cass bucked harder against my hips and said, "That feels so good."

I slid one finger into her asshole and said, "Do you want to cum?"

"Yes." She moaned and thrust furiously onto my cock.

I slapped her ass again with my finger resting firmly inside her ass. "I'll bet you do. I don't think I should let you, though.. You haven't even said please.."

She put both hands on either of my shoulders and yelled, "Please, oh god, please!"

I slapped her ass 3 times quickly and said, "Suck up," While shoving another lube soaked finger into her asshole. I began slowly thrusting my fingers in and out of her asshole while maintaining a firm grip on her right hip. She moaned louder the deeper my fingers went in. By the time her asshole had swallowed my fingers whole I could feel her pussy dripping on my thighs. I slapped her ass cheeks again with my left hand then used it to spread her ass apart.

Cass was riding my cock frantically at this point. She lowered her head and barely formed the words, "Can I cum? Please?"

I laughed maliciously and said, "I don't know, can you?"

I shoved a third finger completely into her asshole. She moaned deeply this time and I felt her nails dig into the flesh on my shoulders.

"M-may I cum?" She asked, timidly.

I thrust my fingers quickly in and out of her asshole. This time her moan was barely audible and I felt her pussy gush onto my thighs. I smiled, knowing that she had just squirted and slapped her ass harder this time. I was now pounding her asshole with three fingers and she was so lost in pleasure that all she could do was rock quickly back and forward while soft moans escaped her lips.

I slid my left hand around and found her clit and flicked it for five seconds. She whimpered and her thighs trembled so badly I thought she was going to collapse.

I laughed and asked her, "Does that feel good?"

She somehow managed to respond with, "God, yes."

I slid my hand back around to her ass and slapped her hard. "I expect better manners from you, Cass."

She whimpered again as another hard blow came in contact with her ass. "I-I'll try to be more polite." She whispered.

I slapped her ass cheek again and growled, "Trying is not enough! When I ask you if you want something, I expect you to say 'may I, please?' and when I ask you if something feels good you better respond with 'yes, sir.' If I allow your clit to be touched you better fucking say 'Thank you, sir.' Do you understand me?"

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