Cassie

Story Info
High school sweethearts finally risk it all for pleasure.
4.6k words
4.17
73.1k
46
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

Cassie and I have known each other since we were kids. I still remember the first time we met each other. I was being pummeled by the neighborhood bullies when suddenly I saw a brown flash. When I finally found my glasses off the floor I saw the bullies running away and Cassie looking at me. From then on we were inseparable. Cassie, though, had a very domineering personality. She would tell me what to do and I was okay with it. First off, the bullies were way too scared to mess with me when I was around her. Secondly, I don't like to make decisions and she was usually right anyways.

Even though Cassie is Latina and I'm Sri Lankan my mom took to Cassie instantly. I think my mom saw a lot of herself in Cassie. I never really had to make a decision in life because my mom or Cassie would make it for me. They became my life strategists.

While I went through life not really caring about anything, Cassie knew what she wanted from the beginning. A year after we met, at the tender age of six, she declared that we were going to get married in the future. Now I might not care about much but I knew enough that I didn't want to get married in the future. Cassie, though, had planned everything in advance and she knew my secret, candy.

"If you say that you'll marry me, I'll give you a Butterfinger."

"Butterfinger? Ok then." I stupidly replied.

Thus, at the age of six I was betrothed to marry.

Cassie and I did everything together. We walked to school together, hung out at recess and lunch and hung out after class. I don't think I spent any of my time awake away from her. Although, it was more that Cassie told me what to do and I did it. It wasn't all bad though. Cassie was the more social, interacting type. While I was quiet and just kept to myself. So I got a whole bunch of friends just through association. Although, it was more like they put up with me so that they could hang with Cassie because they knew we came in a package.

When we turned fourteen though things started to change. Cassie went through puberty first and damn god spent a lot of time on her. She developed a slamming body with a face and boobs that could put Victoria's Secret to shame. Add her hint of a Latin accent and she was every guy's dream. Whenever, we went out all the guys around us looked at her. I even saw some of the male and female teachers check her out!

I on the other hand must have been what god had to make in a rush. I was a scrawny kid with asthma, acne and braces. I bet a teenage Bill Gates didn't even look as geeky as me. Cassie, never left me alone though. Even when she became a cheerleader and I a mathlete she never left my side. One day we were walking to class, her in her cheerleading outfit for our high school pride day, when I heard a voice.

"Ayy, chica! Why are you with that loser? Come over here and I'll show a real good time. I'm a real man and I'll make sure that you'll be screaming my name tonight."

I looked over and saw Chet Anderson, star running back. I looked around and saw that everyone was looking at me to defend Cassie.

Cassie was having none of that though.

"Oh, so you think you're man enough for me?"

"Girl, I know that I'm man enough for you. And I ain't no wimp like that stick you got there."

"Yeah I heard about how man you are. Your ex-girlfriend told me all about that stub you call a penis. No wonder you're always angry. With a dick that small there's no way anyone can jack that thing off."

"What'd you say to me bitch?" he exclaimed.

"You heard me puto. Maybe you need some help, your dick is T-I-N-Y!" she replied.

"Bitch take that back before I beat you silly!"

"Come at me bro! I'm right here. You think I'm afraid of you?"

At this point, I think he knew that there was no way he was going to win this argument. If he did beat her up he'd be a woman abuser. If he got beat up by her though he'd be the laughingstock of the school. The star running back who got beat up by the freshman cheerleader. So he turned his attention to me.

"Not even going to try defending your girl? What a pussy." He said.

"Don't you dare call him a pussy! You're just mad because you're jealous of him." Cassie angrily said.

"Jealous of him? What would I be jealous of? He has so much acne he looks like a pepperoni pizza." He scoffed.

"You're jealous of him because you know he's going to make something of yourself, while you'd be lucky to be mopping up floors when you're 30. He's going to be a doctor and you're gonna be that creepy old guy who talks about his high school days. And while we're wearing out the springs in our bed, you'll be sleeping behind a dumpster." She yelled.

Once she said that everybody went silent and just looked at me while I had the biggest boner I ever had. I saw a lot of looks of jealousy. From then on no one hit on Cassie. Everybody knew she was taken and that wasn't going to change. Once we were walking home though, I asked her if what she said was all true.

She just looked at me and said.

"Of course, silly."

"So umm..., you know, when do you think we're going to have sex?" I said my face getting redder with every word.

Suddenly, she got close to me seductively and whispered in my ear.

"You want to have sex right now?"

"Y..Y...Yeah" I managed to stammer.

"Not yet tiger, when I have sex I don't want to have any birth control around. No pills, no condoms, no anything. Just me and you. But we can't risk having a kid right now, we're too young. Don't ya think?"

"Yeah, of course." I said just to please her. Honestly, at that point I didn't care what would happen after sex.

"Don't worry tiger, when we do have sex I'll make sure that all this waiting will be worth it."

I couldn't fucking wait.

High school went on and we ended up getting good grades, although mine were slightly better. We ended up going to university together, me on scholarship. Because of school policy though the dorms were unisex. Which means for the first time in my life, I was going to live apart from my mom or Cassie. Having freedom was weird. Without having a girl tell me what to do I was kinda lost for the first couple of weeks. I mean Cassie still did come over a lot and hang out but since I was a bio major and Cassie was a sociology major we had separate classes.

With college, came a fresh start, and I was determined not to mess it up. Luckily, my acne had gone away and I got my braces taken off a week before. My body filled out too so I was better looking, a little above average. Suddenly, a lot of girls were coming up to talk to me during class. This never happened before because in my hometown, girls knew that they'd have to go through Cassie to get to me, not that they were interested anyways. This one pretty blonde girl, named Jen, started sitting next to me in Chem class. We started talking and she seemed really cool.

"Hey you doing anything on tonight?" Jen asked one day in class.

"Probably studying for the midterm tomorrow, what's up?" I replied.

"My sorority is having a party tonight, and I was wondering if you wanted to come."

"Eh, sounds fun. I'll think about it."

"Ok, let me know."

When I got home that day, Cassie was waiting for me in my room.

"Hey sexy. How was class?" she asked.

"It was alright. I got invited to a party."

"Oh cool, when?"

"Tonight." I said.

"Tonight? I thought you had the midterm tomorrow."

"Yeah I do."

"You planning on going?"

"Maybe. I don't know I'll think about it."

"You're not going." She said.

Throughout my life I never really had any friends that I made myself. And god help that I might lose the first friend that I actually got myself.

"Why the hell not? Maybe for once in my life I just want to have fun."

Cassie looked at me in shock, I don't think I even disagreed with her once since we were six.

"You have a goddamn test tomorrow and did u forget you're on scholarship?" She finally said regaining her composure. "You need to have a good G.P.A to keep it and I talked to your mom and know that there isn't enough money to keep you in school without that scholarship."

"You know what, I'm going to do what I want. This is my life and I can make my own fucking decisions!" I exclaimed. And with that I walked out of the room, called Jen and told her that I can come.

By the time I got to the party it was in full swing. I had just walked through the door when I suddenly felt two big mounds on my back and heard "You made ittttt!!"

I turned around and saw Jen totally plastered with her boobs barely hanging in her bra. "Let's have some fun!" she said and took my hand.

After that my memory gets a bit cloudy, all I know is that I must have drank a whole lakes worth of alcohol. I woke up so hungover I'm surprised I could even walk to take my test.

From then on I partied with Jen any chance I got. Everything was good until one seemingly normal night. We were riding a five game winning streak in beer pong when we eventually lost. At this point Jen and I were totally plastered.

"Hey sexy, wanna have some more fun?" She said with a wink.

"Hell, ya!" I said not knowing what I was getting into.

She took me by the hand and let me to a dark corner in the party. And held me real close.

"You know, I can tell you're still a virgin." She said.

"How did you know?" I replied shamefully.

"You can just tell these things. I thought you had that girlfriend from high school?"

"Yeah, she doesn't want to have sex yet though."

"Ahh that's too bad. You know that all guys have needs. It's a girlfriend's job to make sure that they're met. They can't rely on porn all the time. And guessing from how red your face is turning that's exactly what you do." She said while laughing.

"You know, I can help you with that." she said suddenly cupping my crotch. "Damn, you sure do have a nice package, I'm surprised that you're still a virgin."

"Come with me and I'll make sure that that ends tonight." Jen said seductively in my ear.

Now it was all fun and games hanging out with Jen so far. But now she was actually offering me sex. To be honest, I was ready to take it. But then a picture of Cassie popped into my head. How she saved me from all those bullies, took care of me when I was sick and never left my side in high school even though I was the biggest loser in school. I knew what I had to do.

I ripped myself from Jen's grasp.

"I'm sorry, you're a great girl but I can't do this." I finally said.

"Are you serious? You're denying me?" She said confused.

"You rather stay a virgin? Than be with me?" she exclaimed "You're a fucking idiot! I can't believe I spent so much time with you! I could have had any guy I wanted! The only reason I even chose you is because I wanted to take you away from that bitch. She always gets the looks from guys, even when I'm around her. I wanted to get back at her, hitting her where it hurts, you. And now you're denying me?"

"Don't you dare call her a bitch!" I said my balls finally dropping. "She's the best girl a guy could ask for. And it ain't my fault you're so ugly that guys don't notice you. No wonder you always dress like a tramp, the only way you can get guys is by being the town bicycle. Everybody gets a free ride huh?"

With that I turned around and left the party with Jen shocked, mouth gaping behind me.

After that I had to go on a walk to clear my head. So by the time I got back to my dorm room I was pretty much sober.

When I walked in, I saw Cassie inside.

"So how was the party?" she asked.

"Eh, it was okay." I replied, not wanting her to know anything.

"Well all these parties must have been fun, your grades have been slipping you know. Do you even check your mail?" She asked.

"What?" I said dumbfounded.

"Look." She said while showing me a letter from the university. "This is a warning letter saying that, they're going to take away your scholarship if your grades don't improve."

I just stared at the letter watching my life fall apart.

Finally, I said "well don't worry about it, I don't think I'm going to be invited to a party anytime in the future."

"Why is that?" she asked.

"Don't worry about it, it just won't happen again."

"I was at the party tonight you know." She said softly.

"You were?" I said my eyes getting wide. "What did you hear?"

"Everything she said."

"So are you here to break up with me?" I asked, not wanting to really know the answer.

"No, tiger. I saw you push her away. She was a bitch, but she was right. I don't take care of your needs. I think it's time to change that."

And with that she got grabbed me by the wrists and threw me on the bed.

"In my family, the woman is always the boss. That's because guys will let you do anything as long as you make sure their needs are met. Unfortunately, I haven't been keeping my side of the bargain. No wonder you started hanging out with that girl. She would have done anything to be with you. I'm going to make sure that that won't happen again. Plus, if you stop going to those parties I know that your grades are going to go up." She said.

"Now just relax and enjoy." She whispered into my ear as she started to take off my clothes.

"Hmmm, look at this huge cock" she said while holding my penis. "I can't believe that I never had this before." And with that she started to go up and down on my cock with her hand. Then she licked the tip and took the entire 6 inches of my dick in her mouth.

Even though it was my first time, it felt like heaven. I looked down to see the most beautiful girl I knew going up and down on my dick. She then took it out and started liking it like a lollipop. That almost made me cum right there.

"Oh look at that, some pre-cum shot out." she said giggling "I wonder how it tastes?" She then took her tongue and licked my head. "Mhmmm, this tastes good, I need to do this more often. I bet the real thing tastes even better." Then she went back to sucking my cock.

"You know I've been practicing with my dildo for this moment." She said after coming back up. "I hope you appreciate it. Just let me know when you're about to cum."

Since this was the first time I actually had a girl on my dick after about a minute of head, I was close to cumming. "I'm about to cum!"

She immediately took her mouth off my cock.

"Sorry, I'm not going to let you cum yet. I got plans for your cum."

She then pushed me off the bed. And started taking off all her clothes seductively. She took off every piece so slowly that I just wanted to rip it off her and get it over with. I thought I was just going to cum just looking at her. But I wanted to know what her plan was so I somehow stopped the urge. She then laid down on her back.

"Come on tiger, fuck me."

I wasted no time in getting on top of her and putting my dick in her wet, lightly shaven pussy. At first it was hard but I kept going till I got most of it in.

"Oh my god, you're so big." She said. "This is as good as I thought it'd be."

I started slow because I wanted to make this last forever. I just put my weight on my arms while I looked at the goddess below me with her face in the middle of mesmerizing pleasure and her boobs bouncing up and down while I fucked her. She looked so beautiful, she looked like an angel.

I pumped in her for about five more times before I had to cum. Knowing she wasn't on birth control though and I knew better than to cum in her unprotected pussy. As I started to pull out to cum on her stomach, she wrapped her legs around me and pulled my dick back in.

"What the hell do you think you're doing?!" She exclaimed.

"I don't want to get you pregnant." I replied. "I thought we were too young. So I was going to pull out."

"The hell you are. Listen here, you are mine. From now on you're never gonna pull out. From now till one of us dies your gonna cum in my unprotected pussy. The only way I can make sure that your needs are met is to have sex with you. And there is no way I'm going to use protection, so it looks like you're going to be the father of my child." She said while moaning.

"Don't worry about it. I'll take of our kid while you keep going to school." She said noting my worry. "This way I know that your grades will go up because I can keep an eye on you. And I'll make sure in return for all that studying that you'll get the best sex you ever had. Because I want a lot of kids and I don't want us to ever stop making them, even when you're in school."

This made me horny as hell, knowing that this beauty wanted me to have a baby with her. Me, some normal shmuck, cumming inside this goddess anytime I want. Mating with her. It was too much.

"I'M CUMMING!" I exclaimed.

She just pulled me into her more with her legs, letting me do deeper. "CUM BABY, CUM. FILL ME UP WITH YOUR BABY JUICE. MAKE ME YOUR BITCH. I CANT WAIT TILL YOU GET ME PREGNANT OVER AND OVER AND OVER AGAIN! OHHHH! I WANT TO BE ON MY BACK ALL THE TIME! I WANT TO BE YOUR BABY FACTORY!" she said while I was pumping my baby juice into her waiting cervix and eggs.

Finally, I pumped everything inside of her and fell on top of her. When I looked up, Cassie was smiling at me.

"How'd you like that tiger? Are you mine now?" she asked.

All I could do was nod.

"You going to go to any more parties?"

I shook my head while still sweating like crazy.

"You know I wasn't kidding about having kids. I really do want a lot of children. And I want to start having them now. Are you ok with that?"

I nodded furiously.

"Good, that's what I like to hear. You know we're not done yet. I want to make sure that I'm pregnant. " She said with a wink. "I heard that the hornier a guy is the more semen he gives out during sex."

"I don't think you can get me hornier than this." I said.

"Oh, really? Is that a challenge? Close your eyes and give me five minutes then." She said.

I closed my eyes not knowing how can she could be more sexy than she was right now with her slamming body and my sperm dripping out of her pussy along her leg.

After what seemed like an hour I finally heard "You can open your eyes now."

I looked up and saw her in a tight strapless red dress that seemed to be bursting out with the curves she had. But I felt like I remember that dress from somewhere. I remember someone wearing it to a cocktail party once. It was my mom's!

"So you do recognize it? Does this turn you on?" she asked in her sexy voice.

"How did you know?" I asked.

Laughing, she said "You know that you never delete your internet history. I've known for a while that you like incest stories with mom and sons in them. Don't worry about it, I think it's hot."

"You do?" I asked cautiously.

"Oh yeah, I mean it's so forbidden it's hot. So I stole your mom's dress, panties and bra. Your mom and I are close so it wasn't that hard. Everything I'm wearing now is your mom's. Unfortunately everything is so tight on me, I need relief tiger." She said "Do you want to role play with me as your mom?"

"YES!" I exclaimed in one of the easiest decisions in my life.

"Good that's what I like to hear." She replied. "Oooh, son you look so hot there lying naked. Would you like your mom to relieve you?"

"Yes mom please." I said following along.

"Ok then honey. Just lay down and mommy will take care of everything. But you have to promise me one thing. Don't cum in me ok? I'm not on birth control and we don't want to have a baby, right hon?"

I nodded, ready to play along.

She took off her panties while keeping on my mom's bra and dress. I have masturbated to that bra and panties so many times while my mom was away. I always wondered if my mom ever saw the cum stains when she came back from work. Cassie started kissing me on my mouth and then started kissing down in a straight line towards my dick. Once she got there she put it back in her mouth. But this time she only went down a few times before she came back up.

12