Cute Cassandra Ch. 02

Story Info
College girl cuckold and party.
3.1k words
45.8k
8

Part 2 of the 2 part series

Updated 10/08/2022
Created 01/24/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This story is 100% true! Only the girls' names have been changed.

A year had passed since the last time I saw Cassandra. She had texted me relentlessly for a month after our first encounter, but her lackluster dick sucking skills left me unsatisfied. Basically, I didn't think she was worth my time.

Her name was almost completely erased from my mind until she wrote me on Facebook one chilly November night. The following message is copied and pasted directly from my Facebook account,

"Hey Todd, how ya been? I know we've not had the chance to talk in a while. Me and my boyfriend were looking for another guy for a threesome. I was told you get kinky. I remember your fun. Get ahold of me if you are interested! K bye!"

The thought of plowing her left me intrigued. I spent a good five minutes deciding whether she was worth the busted nut or not. The only reason I eventually agreed was because I knew my best friend would insult me constantly if I turned down a new number so easily.

She sent me her phone number on Facebook then I called her later that day.

"Hey Cassandra, how you been?" I asked as soon as she said hello.

"Busy with work and school," she said sighing; "how about you?"

"Same," I replied.

"Why didn't you ever call me back the last time we hung out?" Cassandra asked seriously.

"Sorry, I was really busy," I lied.

"That's what I figured. So are you interested in my message?"

"Very," I answered with a smile.

"I might have to get drunk for this to work," Cassandra giggled into the phone.

"Then I'll bring some drinks," I answered enthusiastically.

"Okay, I moved since the last time we talked. I'll text you my address. You can come over at 10 if you want," she said with a business tone.

"Okay, I'll call before I come over."

"Talk to you then," Cassandra said before hanging up.

Every thought I had for the rest of the day mixed with thoughts of her beautiful tits. Classes seemed to drag on, and every conversation seemed to be spoken through a haze. My mind always concentrates only what's important. That day, nothing was more important than Cassandra's pussy.

Each hour seemed like an eternity, even though each minute passed like a second. Time has a way of fucking with a horny man's head, right?

Anyways, classes finished at four and I spent several hours chugging beers with my fraternity brothers before calling her again.

"Hey, my boyfriend is getting off work soon if you want to come over," Cassandra said after we talked for a few minutes on the phone. "I need to put on some clothes first. I just finished a shower."

"Don't worry about clothes. It would be hot if you answered the door naked."

"We'll see," she replied with a giggle.

We hung up after a few more flirtatious remarks. My raging hard-on was begging for the action, and I was ready to please my penis by plowing her pussy. My intention was to fuck her so amazingly that she wanted to ditch her boyfriend for another night with me. What can I say, I'm a home wrecker!

I drove to the store and bought a case of beer and some beef jerky so I would have something to eat after I left her house. (Planning ahead is what tiggers do best, bitch!)

After getting the necessary ingredients for a good night, I drove to a house near campus. She had rented the top floor as a loft apartment. I was forced to park on the side of the narrow town road because there wasn't enough space in the drive-way. The neighborhood was nice so I didn't mind. Besides, my mind was elsewhere as I happily raced up the outside set of stairs. She answered the door in a tiny bathrobe and a smile after I had been knocking for a full minute.

"Hey, come in," Cassandra said opening the door for me.

I walked inside holding a case of cheap Natty Light while she closed the door behind me. Her beautiful body had only gotten better with time. Her tanned legs looked stronger, her butt looked even more toned, and her big tits looked as perky as before. What caught my eye this time though was how much her face had changed. Before she had light brunette hair, but now platinum blonde hair accented her facial features perfectly. Her soft brown eyes looked brighter, her eye lashes looked longer, and her ruby lips looked fuller. It was the first time I realized how much hair style can change everything you notice about a girl's face. She had kept the same girlish look as I studied her unhidden beauty.

"Am I different than you remember?" Cassandra asked as I tried to disguise my stunned expression.

"Yeah, your hair looks great," I said trying to recover my senses.

"Thanks, I just had it done last week," she said running her hand through it. "Do you really like it or are you just saying that?"

"I think it fits you perfectly," I said stepping closer to her.

"I'm glad you like it," she replied putting her hands onto my chest. "You really should have called me."

She bit her lip looking up at me like I should apologize for being a dick. Too bad I never apologize to sluts.

"What are you wearing under this?" I asked untying the belt to her robe. She leaned back as I pulled the knot loose. Her satin cloth fell open as the knot gave way. Her breasts came into view while she continued to bite her lip. The look in her eyes was one desperately seeking approval.

"You are so beautiful," I whispered before kissing her softly.

Cassandra's moan against my lips was enough of a response for me to know she wanted more. We wrapped our arms around each other as we fell playfully onto her couch. Our tongues caressed as my hands slipped across her toned teen body. Her legs wrapped around my hips pulling us closer together. Her right breast heaved in my hand as my finger tips slid across her pink nipple. Another minute passed before we stopped long enough to breathe.

"Oh boy, I think I need a drink after that," Cassandra said pushing lightly against my chest so I would get off of her.

"I have beer if you want one," I said glancing at the case lying on the hardwood floor.

"I hate beer," she said brushing her hair back with manicured fingers nails. "I think I have some tequila in my kitchen."

Cassandra gave me another quick kiss then led the way across her tiny loft apartment to a small kitchen. My eyes left her beautiful body long enough to take in the tiny college apartment. The walls were bare except for an occasion poster or picture. The hardwood floors showed the true age of the house, but the remodeled kitchenette made it obvious the top floor hadn't been rented out for long. I gave up at looking at anymore of the apartment as soon as she grabbed a bottle of tequila from her counter and poured two party-sized shots.

"What time will your boyfriend be here?" I asked taking the full shot glass from her outstretched hand.

She shrugged; "he should be here soon."

I took the shot and handed her back the glass. She turned her back to me and took the shot. It was a few seconds before I could see her face again.

"Why did you turn away?" I asked with a smirk.

"I make silly faces when I drink hard stuff," she replied with a pouty face.

I laughed; "that's cute."

"No it's not," she said stomping her foot like a little girl. Her tits jiggled in response and left my eyes following them hypnotically. She noticed my eyes and swayed her hips a little so her tits would keep moving.

"You like them don't you?" Cassandra asked grabbing them playfully.

"Yes," I answered watching her pinch her nipples.

A sudden knock on the door brought me back to reality.

"He's here!" Cassandra exclaimed as she rushed to the door.

I poured myself another shot of tequila in preparation to meet the bitch who was going to let me fuck his girlfriend.

Cassandra walked back into the kitchen followed by a shorter extremely average-looking guy. He wasn't fat, didn't have muscles, and didn't even have nice clothes. He was normal in every way. I tried to figure out how he landed Cassandra, but I saved myself the thought by taking the tequila shot instead.

"Hi, nice to meet you, I'm Seth."

I shook his hand, "Nice to meet you too. Want a shot?"

I purposely didn't tell him my name as I offered Cassandra's alcohol to the stranger.

"Yeah, let's all take shots!" Cassandra cheered grabbing her glass and another for Seth.

We took two more shots while keeping the small talk going. He mentioned where he worked and she talked about school. I wasn't listening because I was too busy staring at her tits which were still openly on display. He barely looked at her. He seemed to concentrate on the tequila pouring more. Finally, I grew tired of the small talk and asked what her bedroom looked like.

"Oh, I can show you!" Cassandra said pulling my hand towards a closed door on the other side of her tiny loft apartment.

She opened the sturdy wooden door and flicked the light switch instantly illuminating her tiny bedroom.

"Don't mind the mess," she said kicking some dirty clothes away from her queen sized bed. I looked past her dirty clothes and messy bed to a cage next to her open closet.

"What's that?" I asked pointing.

"That's my pet weasel," Cassandra squealed as happily bouncing to the cage like a little girl on Christmas. She opened the cage door and pulled out a live weasel.

"Why the fuck do you have a pet weasel?" I asked.

Seth chuckled behind me. Apparently he agreed with my question.

She gave us a dirty look as she answered; "I love Monopoly." She hugged the weasel to emphasize her feelings.

"You have a pet weasel named Monopoly?"

"Yes, don't make fun of him," she said holding him closer.

"Whatever," I said shaking my head. "Put him away and come over here."

I had better things to worry about instead of a stupid pet with a lame name. Cassandra closed the door with the weasel safely inside then crawled up onto the bed. Her satin robe hung open as her tits swayed back and forth.

"Why don't you two start," said Seth retreating back to the bedroom door.

"Good idea," Cassandra added letting the robe fall off of her shoulders seductively.

I took off my black tee shirt and shoes while she continued to crawl across the bed to where I was standing. I stopped moving as she undid my belt and unzipped my blue jeans. Her ass wiggled behind her as her lips kissed my lower abs. The rest of my clothes ended up on the floor as her right hand cupped my balls. She pulled my hips hard making me fall onto the bed. I almost fell on her but I was able to shift my weight at the last second.

Cassandra giggled, "I think I'm a little tipsy."

"You're strong when you drink," I said moving fully onto the bed.

She giggled again as she kissed my cock. Her manicured nails scratched lightly down my chest and abs while she kept kissing and licking my hard shaft. She stopped once to wiggle her ass in Seth's direction, but his nervous look betrayed his reasons for staying close to the door. She turned back to me and smiled.

"Guess it's just us for a few minutes."

Cassandra punctuated her sentence by taking me all the way into her mouth. The steady sliding motion of her tongue and mouth made my eyes roll back into her head. This definitely wasn't the same blowjob as before. Her hand slipped up and down following the motions of her mouth. Her tongue pressed against me while her hand twisted to match the intense sensations. My mind screamed in ecstasy as her amazing new found abilities.

"Do you want to fuck me?" Cassandra asked looking up into my eyes a few minutes later.

"Yes," I said breathlessly.

"Seth will you get us a few condoms," she ordered without looking away from me.

I glanced at him long enough to see him do as he was ordered. She sat up and took one when he held them out for her.

"You should take off your clothes too," she said looking at him.

He took off his clothes but stayed a ways back from the bed. He kept grabbing at his limp dick while Cassandra looked at him sympathetically.

"I'm a little nervous," he said shyly.

Cassandra shook her head and opened the condom wrapper. I laid back and let her put it on. She giggled and laughed as she rolled the tight rubber down. I'm not hung but the tiny condoms made my dick feel like it was being shrink wrapped. I could barely feel her pussy when she lowered her hips onto my waiting dick.

She grinded back and forth while I tried to regain feeling; "is something wrong?" She asked after seeing the pained look on my face.

"These condoms suck. They are too small," I replied.

"Sorry," Seth said sadly.

Cassandra continued to work her hips like a porn star. I grabbed her breasts trying to take my mind off of the pain blossoming on my cock. Finally, I pushed her off of me and stood up.

"Seth, you should take a turn bro," I said angry at the condom.

Cassandra rubbed her pussy while looking at me. "What's wrong?"

"This condom is killing me," I replied.

Seth sat on the bed next to her and rubbed her pussy while his other hand frantically groped his limp man meat. I left the room tearing off the pathetic rubber. It was the first time I had ever been too big for a condom. It should have made me feel manly, but it left me annoyed instead. I wandered into the kitchen and threw the condom into the kitchen sink with a smile then poured myself another shot. I figured she could clean up after me if she wasn't going to get me off. I could hear hushed whispers coming from the bedroom, but I didn't care what they were saying.

"Pour me one too," Cassandra said leaving the bedroom a few minutes later.

"Why aren't you in there having sex with Seth? I was coming back," I said refilling her shot glass.

"He can't stay hard," she said with a sigh.

"Well it happens."

"It hasn't happened with you," she said turning away from me to drink the liquor.

"Yeah, well, you're hot," I added watching her butt while she took the shot. She turned back around a few seconds later with a smile.

"You're sweet," Cassandra purred setting the glass on the counter then dropping to her knees in front of me.

She took my dick back into her mouth with renewed energy. I leaned back against the counter and closed my eyes while she worked. Seth came out of the bedroom and sat on the couch looking defeated while his girlfriend sucked my growing dick enthusiastically.

"Let's go back to the bedroom," I said with a hungry look in my eyes.

Determination to make her scream guided my thoughts as she stood up and took my hand leading me back to the bedroom. Seth followed us like a sad puppy. Cassandra crawled onto the bed and wiggled her ass while Seth handed me another condom. I put it on angrily and entered her from behind. Her immediate intake of breath was enough to tell me she loves doggy style.

Another moan escaped her lips before she bit the pillow to hide the sounds. I pulled her hair thrusting into her again. Her face lifted from the pillow as I pulled harder and another loud moan echoed in the bedroom. Each thrust was met by another moan, and they started to come faster and louder as I sped up. My dick hurt from the rubber, but I didn't care. The moans felt like encouragement and my instincts responded. I pushed deeper and faster and the condom stretched further and further. I pushed in hard enough to start bunching the rubber at the bottom of my dick. The condom kept stretching while I kept fucking her. Her pussy grew wetter and my dick slipped deeper and deeper. Her moans became more animalistic and she claimed she was about to cum. I thrust in again and felt the condom snap under our furious movements. Instantly, wave after wave of pleasure assaulted my senses. Her wet tight pussy gripped my bare cock. It was amazing! She must have felt it break too because she grinded her hips back against mine.

"Don't stop," she screamed. "I'm cumming!"

She tried to bury her face into the pillow, but my hand held her hair too tightly. The moans echoed loudly enough to wake up people within a block of her upstairs apartment. After the first orgasm, she rolled over and begged for another. I answered her by shoving my bare cock into her and continuing my forceful pace. I stopped only long enough to take the ruined rubber off. She watched me and smiled. Seth probably wanted to say something but he was too much of a bitch to make a sound while I fucked his girlfriend. Finally, after a full hour of rugged sex and several heart stopping orgasms, she suggested we take a break.

"I'm going to be sore tomorrow," Cassandra said trying to catch her breath.

We collapsed onto the bed in a sweaty heap of sex and spent energy. Seth sat on the floor naked and forgotten. After a few minutes of relaxing, I checked the time on my phone and started to get dressed.

"Call me if you want to do this again," I said zipping up my jeans.

"You're leaving? You haven't cummed yet," she said sadly.

"That's okay, you can just make me cum tomorrow," I replied putting on my shirt.

"Okay, I'll call you after class," she said pulling a blanket over her naked body.

I stepped over Seth's legs and left the apartment without even saying good-bye to him. Once I climbed into my car, I opened the bag of beef jerky and turned on my car. It was definitely a fun night for Cassandra and me. It was probably a horrible night for Seth, but he's a little bitch and no one cares what he thinks.

The funniest part of the story is that I think those two ended up getting married.

  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousabout 7 years ago
Todd is a dick

Cassandra deserved better. Told ego masterbation story. I'm sorry Cassendra had such a shitty cuckholding experience. Never does he consider what Cassendra wants. Or what Seth wants. Boo.

AnonymousAnonymousover 7 years ago
Todd is a jerk

Todd thinks he is better than everyone else, male and female. He thinks negative thoughts of other people. I hope Todd’s girlfriend is having sex with other guys; it is not fair for one partner to be with others unless the other partner is also. Todd should’ve brought his own condoms. I hope Seth turns into a stud, the way Cassandra improved her skills. I hope I never meet Todd.

adrenaline61938adrenaline61938about 10 years agoAuthor
sorry

There is a gay section. Maybe you'll like the stories there more. I'm straight and all of my stories are as well. Enjoy!

AnonymousAnonymousabout 10 years ago

I was hoping there was a potion in the condom and it caused your mighty cock to turn into a little sissy clit and the wimpy boyfriend would end up fucking you like the sissy fag you turned into needed. Then he fucked his girl and you beged to eat his cum from her much fucked pussy.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

My Roommate Takes My Girlfriend His girlfriend seduces his roommate.in Exhibitionist & Voyeur
Amanda, My Sweetheart Amanda goes to college to have some fun.in Exhibitionist & Voyeur
My GF Becomes our Roommate Didn’t know GF was a nudist till after she moved in with us.in Exhibitionist & Voyeur
Fresh Pt. 01 His hot white freshman girlfriend encounters black dick.in Interracial Love
Just One of the Guys Ch. 01 Brian's girlfriend warms to his buddies quicker than he hopes.in Exhibitionist & Voyeur
More Stories