High School – 1st Anal


“Uh!” She rolled over, and sat back down on the couch.

“What?” She just shook her head, and gripped the rubber.

“Just come here.” She pulled it off, and started sucking the tip, feeling my balls in the other hand. So, I shrugged, and just enjoyed it, until I felt something rubbery in my crack.

“Uh!” I backed up, and my cock popped up to slap my belly.

She grinned, “Now you know how it feels.”

“It slipped!”

“Yeah, like every time you let it slip up,” she got up, and pushed it down so it bounced back up. Still hard as a rock. “Just enough to touch my butthole, but I had a boyfriend that liked that.”

“You let him do anal, but not me?”

“Yeah, because he knew how it felt. By which I mean he liked my fingers up his ass when he got off.”


“Huh! Now you’re going to mansplain how my boyfriend, who you never met was gay, because he had sex with me?”

“No? Come on, don’t leave me like this.”

“Well, I’ll make you a deal, I’ll show you how to do it, but you have to let me show you.” She held up the rubber, and wiggled her fingers inside it. “You might like it.”

“Yeah, well I’m not gay, so forget it. Why don’t you just suck me off, before dad gets back?”

“Forget it,” she pulled her top on, and picked up her bra. “I can get a boyfriend who’s not so prudish.”

“I’m not a prude, but if you want to break up with me, just because I don’t want it up the butt, then fine.” Waste of a perfectly good rubber.

“No, because you keep trying to sneak it in the back door, when you don’t know what you’re doing.” She turned around, and threw down her pants. “If we’re breaking up over this bullshit, then at least get it right. You’re the one with the problem.” She poked my chest, “And that’s the reason why I never trusted you to do it right. You can’t learn, because you assume that you already know everything there is to know about fucking, and you’re entitled to whatever you want just because you have a big dick. Well, let me tell you something, mister dickhead. That just means you have to be more careful, and do more foreplay before you just try to stick it in, if you had any idea what foreplay means.”

“I do foreplay,”

“Yeah, but you’re always in such a rush to get your rocks off, you don’t even pay attention to what we want. Then you get jealous, and accuse me of cheating on you, as if Stephanie,” she counted on her fingers, “Tracy, Stacy, and Tiffany B. didn’t tell me all about it, right after you cheated on me, and left them unsatisfied.”

“They did?”

“Ha,” she shook her head. “Yeah, stud. Everyone knows all about your big dick, because you’ll stick it in any hole that’ll hold still long enough, and what do you think we talk about when you’re not around?”

“Me? Behind my back.”

“Yeah, you selfish hypocrite. To think I was proud of myself for holding the record, and putting up with your bullshit for over a year. So, now you feel betrayed because we talk about it behind your back, but not guilty for sleeping with ALL of my friends after we started going out. Oops! It slipped. Yeah, they told me all about the times it slipped, and just happened to poke their assholes, because you’re obsessed with it, and you’re not willing to learn.”

“I can too learn! I’m willing to learn anything about sex, if you’d just stop yelling at me, and god damn it, I love you! That’s why I put up with you, you ever ask yourself that? Well, it’s true, I love you even now after you tried to drive me away with this bullshit I already know. Well, not the part about your friends banging me, and bragging about it, but the other stuff?”

“Like what?”

“I know the blood rushes out of my head, and I try to rush through foreplay, but I can’t help it. It’s got a mind of it’s own, you know that, and your girlfriends took advantage of it too. They tell you that I don’t even have their numbers? They call me, for booty calls, because they know that I can’t turn them down, after they broke up with me.”

“Yah! Well, they tell you where they got your number?”

“From each other? They all went out with me before, you know that.”

“No, because it’s on the door in the girl’s room.”


“Yeah, really. Somebody put it up there, but I have no idea who. It was already there when I started freshman year, but it says for the biggest dick you’ve ever seen, call Dave, and you still haven’t changed your number.”

“It really says that.”

“Well, it’s an exaggeration of course, but everyone knows you’ve got the biggest one in school. Well, maybe some of the black guys are bigger, but the biggest white guy.”

“Wow, no. I didn’t know about that.”

“Of course not, because you’ve never even been in there.”

“Wait, when you said the girl’s room, which one?”

“The locker room, in the gym?”

“Well, that explains all the freshmen, and sophomores.” I shook my head, “And the coach.” I grinned.

“Which one?”

“None of your business, but she called me, and I didn’t even ask her how she got my number. I thought maybe she got it from the office, but she just sexted me.”

“Really? Well, that does explain why she never had it painted over.”

“Yeah, she called me from her office, and said she heard the rumors, but she just wanted to see for herself if they were true. I could barely even get it up, looking at her wrinkled tits, but I just closed my eyes, and thought about you.”

“Huh!” She rolled her eyes, but smiled anyway, then went in the kitchen.

“Where you going?” She turned around, and pushed the drawer shut with her hip, but she pulled a yellow rubber glove out of a bag. With another one in it, but she just told me “Go back in the living room, I need to see if I can find some lube, or something.”

I swallowed, and nodded, but if this is what it takes to make it work, I’m down. I don’t even care about doing her ass, I’m just happy watching her tense up when I touch it, but I know it’ll never fit. Probably, I man. All right, I know I have a problem, but she doesn’t understand how much I got teased about it, when I was a freshman. It’s like my first few growth spurts went right to my pants, and it was a couple years before I even started growing into it, and yeah they’re just jealous, but that doesn’t mean they get to say talk all that shit about me, but they’re right. They’re all right, I kept trying to put it where it won’t go, because it’s too big, and all the guys that wish they had a 9 incher don’t know what they’re talking about. Honestly, it’s caused more trouble than anything, and it wasn’t until last year that I even found a girl that wasn’t scared off by it.

“Just bend over, and relax.” I lost my hard-on, but she tugged me hard again from behind, and rubbed the greasy fingertip on a lot, before she even started to try to push it in. “Huh, how does that feel?”

“Okay, but not like. Good or anything, can you just hurry it up, and get it over with?”

“You know your dad won’t be back for hours.”

“Yeah, but I still want to do you, and we have to clean up the house before he does.” I thought I would hate it, how much she talks, especially in bed. Rick told me all about it, and bitched about it more than anything, but she’s right. Communication makes it better, and even when we fight, we end up fuck fighting, so it’s like makeup sex without the breakup, but I squirmed when it finally opened up. She wiggled it in. “Uh, it’s supposed to feel good, isn’t it?”

“Not right away, first you have to loosen up,” She wiggled it in deeper, and twisted it around, with her fingertip curled, so it rubbed around the inside.

“Uh!” I felt a little drool in the corner of my mouth, and I licked it, but then my ears burned, when I realized that I was starting to like it. “Do that again?”

“What?” She pulled out, and poked it again. “This?” Wiggling it.

“Uh, when you got it in, and rubbed around the inside.” She twisted it. “Uh!”

“You like that?”

Now, I’m really drooling, so I reached back. “Can you hand me my shirt?”

“Here,” she grinned, and held up her panties.

“Huh!” She stuffed them in my hand, and curled up my fingers, but then she rubbed it again.

“Snh!” I just piped my mouth, but I could smell her pussy, even more in them, because we did a lot of foreplay before she bent opver. With her ass in the air, and her pink pucker stretching out when I started fucking her, but I couldn;t resist slipping it out, and painting it with her juice on the tip of the rubber.

“AWH!” I stuffed them in my mouth, when she pried me open, and her nail caught me on the side, but through the greasy rubber glove, it didn’t scracth me. It just surprised me, and I remembered the way she jumped. They all do, and tense up so they’re nice an tight when you hit that button. “MPH!” She crossed her fingers, so the one inside me covered the nail of the other one when she stretched me out around it, then twisted to screw them in like a drill, and now the panties are so soaked, it’s starting to leak out on the back of the couch, but all I can do is bite it, and try to breath through my nose, but it’s so intense, and my balls are bouncing on her wrists from her relentless tugging.”SNH! Ngh snh! Ngh Snh!” She let go, so my dick swung, and spurted up between my legs. It made me clench up, so tight around her fingers, and now I know what she was talking about. She said her boyfriend loved her fingers up his ass when he got off?

“Huh!” I pulled her panties out, just so I could breathe, then gulped, and wiped the drool off on the back of the couch when she let her fingers slip out, and my asshole pucker shut. “Huh!” I sat down, and felt the wet cushion stik to my leg, but I didn’t care. I didn’t care that I’m sitting in my own wad, or she was going back into the kitchen. I didn’t even care that I was going to have to do something about the greasy mess that was starting to leak out, but I was a little scared that it might be shit. “Holy fuck, I’ve never been so satisfied in my life!”

“You think you could do that?”

“In a minute, I don’t even know if I want to move.”

Then, dad came home when we’re cuddling naked on the couch, and I had the other glove greased up so I could wiggle my longest finger up her back door, with my thumb all the way in her cunt, but she tensed up when she heard the key in the lock. That squeezed my finger out, and she hunched when my thumb popped out, but there was no way we could grab our clothes, the can of butt butter from his bedside stand, or turn the cushion over before he came in.

“Ah shit.” He put his hand up, and looked away. “I’m sorry, I’m just going to go to bed.” He kicked the door, and practically ran for the hallway.

“Ub!” Tiffany had whatever clothes she could grab over her body, but she laughed, and shook her head. “Well, that was cool.”

“You think so?” I just let my fists relax.

“Yeah, he wasn’t even mad, let alone kick me out.”

“Well, it’s not like the first time I had a girl over, and he walked in on us.”

“Oh, they never told me about that, but it must run in the family.”


“You know,” she pointed at my dick.

“Yeah, of course I got it from him. What did you think, I got it from my mom?”

“Well, I never saw it before!”

“Huh!” I didn’t even think to check if he popped a bone when he caught us.

“So, what happened to her, anyways?”

“She wasn’t as cool about everything as you are, so finally she got fed up, and stopped trying to change him.”

“Yeah, most girls can’t stand womanizers. My mom did the same thing and left my dad when she caught him.”

“So, he cheated on her too?”

“Yeah, but not my step-dad. He’s boring, and faithful.”