She Dated a Bad Boy in High School
Many years ago, back when I was in high school, before I started dating Jason, everyone told me to avoid him. They told me he was a bad boy and would corrupt me.
Well, that didn't stop me, even though it should have.
Maybe he just needs the right girl to set him straight, yet two weeks after our first date, he was popping my cherry in the back of his Beamer.
Sure, I had fooled around with other guys, giving them hand jobs and such, but he was so much bigger, I just had to find out what it would feel like, and he was so confident that I let him.
That first thrust fucking hurt, but then, after I got used to it, I liked it. A lot. He made me cum instead of just wanting to get off, and so I found myself on my back all the time with him, until he wanted to change things up.
Then I found myself on my hands and knees, bent over, sitting on him, lying on my belly, and on my back again with my legs up in the air… and any other way he wanted to position me.
I was down to get fucked every which way. Each day brought a new position, and a new way to enjoy the excitement of being in lust with someone.
We did it multiple times a day and used each time to experiment a little more. Of course, I knew he had done most, if not all, of those positions with other girls. He had a lot of experience if his reputation was correct, but why shouldn't I also have that experience.
After a couple of months, he told me he could get any girl, but he chose to be with me because I was so much fun.
In my mind, I thought he might love me. But part of me was thinking he just loved fucking someone who turned out to be easy. But then another part wanted to see if he could.
"I bet you couldn't get my friends to fuck you."
"I bet I could get them all…"
"Well, I know what you get if you're right. But what do I get?"
He thought about it. Valentine's Day had passed, but prom was coming up. He promised to pick out the nicest dress for me and get a fancy hotel room for us to enjoy. That wasn't much of a stretch. Jason had money… like real money. He was a trust fund kid before that meant anything.
He told me what to do, and so I talked him up to my friends. They knew I was dating him and knew I was screwing him every chance I got.
Now I was giving even more details, not just how he felt good, but how he made me cum multiple times on Thursday when we skipped class. Or how big his dick was. Or… well, you get the idea.
Jason didn't say anything to me for a week or two. I guessed he was striking out, which made me happy. Seeing how prom was only about three weeks away, I thought I had it in the bag and started looking for dresses I'd never be able to afford on my own.
He called me in a whispered tone on my house phone… back then it was just a phone. We didn't have cell phones, at least not like you think of them now.
"Listen and be quiet. I'm at Amy's house," he said, then I heard the phone drop on the floor.
"You look nice like that," I heard him say.
"I thought you might like," it was Amy.
I heard him flirt, but not too hard. I knew how convincing he could be when he wanted to be. He was just being nice.
"I don't know if we should," he said.
"She doesn't have to find out. Besides, don't you want to be with someone with bigger tits?"
Amy had bigger tits… bigger than most girls in my school. In high school she was already a solid D cup, and loved showing off her cleavage in plunging tops, or how big they were with tight shirts.
"Oh, wow, I can't believe you took your shirt off… and you've got nothing underneath… I thought you would wear shorts… or at least panties…" Jason said.
"I have to say I do. I love a smooth pussy…"
"I know, your girlfriend told me, and how she loves shaving it for you. So I thought I'd show you mine. And since I've been doing things longer than she has, I thought you should be with someone who can show you a few things."
"Well, that's nice…I should…"
Over the phone, I heard the wrestling of sheets, or something.
"Wow, you really want to…"
"Yes… now pull it out…. Oh, fuck… she wasn't lying… your thing is fucking huge…"
At that point, I knew what was happening. He had pulled his cock out, and she was looking at it while already naked. Or maybe she had pulled it out for him.
Amy was the first of my friends to lose her virginity, and she loved fucking. She'd been with a dozen guys already, and now she was about to fuck my boyfriend.
I kept hoping he would run away. Instead, I heard the bed squeaking. With each squeak, I could hear her moan. Each moan was getting louder and louder.
"Oh, yes. Oh, you feel so good. I want it… give it to me… give it to me…"
She cried out in pleasure as my boyfriend fucked her. While she had told us of her exploits before, I had never heard her actually having sex. I even heard him grunt as he emptied himself into her.
I cried a little, being betrayed by the two of them, and listening in on every detail.
"We… we can't do that again," Jason said.
"But I want to. I'll do you every day, and let you empty your balls inside me, anywhere you want."
"Anywhere?" I could tell he was being tempted. "No, this had to be a one-time thing."
"I'm going to need it more than just this once," I heard her say.
I could hear kissing sounds, and I heard him moan a little, just like when I sucked on his dick.
"See, you like it, and I bet you'll be fully hard again… think about it. You can fuck me, and then you can cum on these."
I couldn't see, but I could imagine her holding up her breasts. She loved having guys cum on them, and would brag about it to other girls about how guys loved to titty fuck her, since she actually had tits.
I could hear the bed squeaking again and knew he was fucking her a second time.
This time I wasn't as upset. I heard him using her, fucking her, and her responding to his enormous cock. As she came, I realized I was a little turned on by listening to them.
"I've got to get cleaned up… you made quite a mess," I heard after he came. I assumed he emptied himself on her tits.
"I told you I could," I heard him whisper into the phone. "That's one down, I'll be over soon."
He hung up the phone before I could say anything.
When he got to my place, I wanted to slap him, but as he kissed me, I couldn't help but melt into his arms. He quickly took me to the bathroom where he bent me over the counter and fucked me from behind.
"Were you at least thinking about me?"
"Of course," he said as he fucked me.
He lasted a decent amount of time, but that still means I missed out on two times to fuck him.
"Uh-huh," I half moaned as I was so close to cumming, knowing he was fucking me with his dirty cock after fucking my big titted friend.
"She was. I liked it. But I came back to you."
Two days later, I heard Samantha getting railed by my boyfriend. I was turned on hearing her filthy mouth as he made her cum multiple times. It was really dirty, and I was super wet when he got back to my place.
He tossed me onto the sofa, and we fucked right in the living room where my mom would catch us if she came home early.
I was scared and excited.
The next day, I was masturbating as I heard him fucking Emily, my oldest friend. Her little "uhs" repeating over and over again did it for me. I had to cover my mouth as I came, for fear of her finding out I was listening to her.
When he came over, I told him I played with myself while he fucked my friend. "Really?"
I was sitting on his lap, riding his cock. He picked me up and told me to show him. I was embarrassed, but I lay back on my bed, spreading my legs, showing off my smooth pussy. I rubbed my pussy with two fingers, before pushing them both in.
He made me keep playing with myself until I orgasmed, just as I did listening to him fucking my friend.
As my orgasm faded, he climbed on top of me and fucked me hard and fast. We both quickly orgasmed.
I heard my mom at the front door, and he had to sneak out, but it was worth the risk of getting caught. If anything, it made it even sexier.
The next day, he just came over to my house, no friends for him. I think he wanted to see me masturbate again… either way, he got me naked really quickly, like he always does.
After we fucked the first time that afternoon, we lay next to each other. We had talked about my friends, who he's fucked, what he liked, and what they were like. I found it interesting to learn about my friends.
"I think you want to keep fucking them," I teased.
"I want to keep fucking you," he said.
"Well, I'm here and naked," I shot back.
"And soon, really soon…" His dick was showing signs of lift again.
"Look, there's something else I want. I thought this whole thing was a joke, until you started pulling it off… So instead of our bet, I want something different."
"You're fucking your way through my friends… I want you to set me up with yours."
I reached into my drawer and pulled out one of my dad's dirty magazines. I had already opened the article I wanted. "Getting your girlfriend to say yes to a threesome!"
"Yep. And I want you to set it up. Look, here are steps we can practice. And I say we do each step with a different friend."
It started with two guys taking turns. Then a spit roast, then some other positions… and finally a double penetration.
"That would be like five of my friends… you want to fuck five different guys?"
I climbed onto his lap. He was already hard thinking about it.
"How many girls did you fuck before me? And how many of my friends have you already fucked? And are going to fuck to get through the whole list… You think you deserve a harem… well so do I."
"You think I want a harem?"
"What, you'd say no to having me and three or four of my friends constantly pleasing you?"
"Well, no," he said as I rocked back and forth on him.
"And I want to try a gang bang once we get through the list. I want to experience as many cocks as you've experienced pussies… is that so wrong?"
"I… I didn't think girls…"
"Bullshit. You know we both like sex… that's why you're banging your way through my friends. I just want my turn… and I want you to bring them to me. Not just talk me up like I did, but bring them ready and willing to fuck me… and you're going to watch and help."
"And why should I make it so easy for you," he said, as I continued to rock back and forth on his cock.
"Because if you don't, I know how to hurt you, trust fund kid… you think you're invincible, but I know better. And I know you want it too."
"Then, if I like it, we keep fucking each other, and maybe our friends… I want a lot of cocks, and I bet I could convince some of my friends to come and help me serve you. Are you telling me you wouldn't want a threesome, or more, where you're the only guy?"
He shot his load deep in my pussy at that thought. He really liked it, and I don't blame him.
He continued to bang his way through my friends. Only Nicki shot him down. While he went through my so-called "friends," it let me know who I could trust and who I wouldn't feel bad about using.
And Emily, well, she couldn't look at me for over a week. She finally confessed everything to me, even though I already knew it all. I held her as she cried, saying it was all her idea, and she felt so bad.
I hugged and forgave her… of course I did. But I had a plan. Emily's boyfriend was kind of cute, and so I told her I wanted to spend some time with him. But so he didn't think that she cheated on him, we'd have to do him together, but he has to fuck me.
She reluctantly agreed… Her boyfriend wasn't nearly as big or good as Jason, but it was fun getting a second dick in me… and Emily's boyfriend never needed to know why he was getting so lucky with his girlfriend and me.
As for Jason's friends, well, he came through. I just might not have told him I had a FMF threesome first… But I had lots of MFM threesomes with him and his friends.
Since Jason couldn't get everyone, he also fulfilled his end of the bet. He bought me a cute dress and got me a fancy hotel room.
In the hotel room, all of his friends were waiting, and I got my gang bang. Well, the first of many gang bangs I'd have in the future.
I knew I loved this crazy life, and so did he.
So we kept dating and fucking, and inviting others to fuck with us. We did this through the rest of our senior year in high school and all of college. College-aged kids are willing and wanting to try new things, and we were very happy to help them experiment.
We got married soon after college and had a wild honeymoon where we invited a lot of our friends to come over and help us celebrate.
Turns out Jason didn't need a good girl to turn him right. He needed the right girl to let him live his best life, and I was just that girl.
To this day, we both let each other play with others and let each other listen in while we can. I still play with myself every time I hear him fucking some other chick if I'm not there with him, and he jacks off listening to me cum from another man.
It may seem weird to some, but it's perfect for us.
romaincrisis
s-u-f-j-a-n-s-t-e-v-e-n-s
theartofmadeline
blakekathryn
ellievsbear
tangentwithtanner
