πŸ“š prissy rissy Part 14 of 14
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Prissy Rissy

Prissy Rissy

by Spector_dugan
19 min read
4.64 (37600 views)
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"Do you have your old uniform?" I asked. I did my best to make it sound like an idle question, rather than something I'd been building up to for a while.

Krissy and I were in her bedroom. Weirdly for us, we were still clothed. I was lying back in her pink bed, surrounded by stuffies, and staring up at the ceiling. Krissy lazed across from me in the other direction, her adorable, lime-green-nailed feet up on the pillow by my head.

It had been a strange day already. I'd spent a distracted morning at work, my brain so focused on the night before that I could barely pay attention to what I was doing. Obsessing over what my parents had said (Jewish guilt is a thing, donchaknow). Then I'd raced home to intercept Krissy at the front door of my house.

My parents hadn't forbidden me from having her over. They hadn't explicitly mentioned anything about Krissy at all. Frankly, I was 20 years old, there wasn't much they could forbid, anyway.

And even if they had expressly said I couldn't have Krissy over, they were both at work all day. The only way they'd know was if my sister, Jessica, told them. And I knew that wasn't a concern. Jessica wasn't the tattling type. There was nothing to stop me from staying on the same track as before and railing my girlfriend in my bedroom.

But something (the aforementioned Jewish guilt, probably) kept me from doing it. Whether I was actually breaking a rule or not, it seemed like a bad idea to have Krissy over the very next day. So, I told Krissy that my house was going to be out of bounds. At least for a little bit. I kept things simple and told her I was having problems with my parents. That was a thing she understood quite easily.

But it left us with a dilemma. If I'd learned anything from the day before, it was that the backseat of my sedan was not a viable solution. I knew Krissy wasn't going to do it in a park or a movie theater. And we weren't going to stop having sex -- don't be ridiculous.

That left us with one option, returning to the scene of our original sin: Krissy's house. Admittedly, this was like jumping out of the thornbush to land in the poison ivy, but, in the moment, it felt like the best choice.

We'd tiptoed through Krissy's front door. Distant, we heard the screams of a vacuum strangling itself on the carpet. Her mom was nowhere to be seen. So, we raced up the stairs to Krissy's room. We closed the door behind us, one last transgression, and settled onto the bed. But though we'd escaped to sanctuary (sort of) it still felt dangerous to simply get down to it.

So, we lazed around, fully clothed, and had awkward conversations. That led to my eyes wandering around the pink bedroom, past the Care Bears and the NKOTB poster. To where Krissy's closet was cracked slightly open. And the thought bloomed in my brain.

Did Krissy still have her uniform?

"You know your cheerleading outfit," I said, "Do you have it?

It had been a bit of a trick question. I was pretty positive I saw it in there -- the green-and-gold striped skirt and sleeveless top was stuffed next to a frilly, pink prom dress and a bunch of other random, dusty outfits.

Krissy cocked her eyebrow at me. I smiled back at her.

"It's probably in there somewhere," she said, dismissively. The fact that she was confused, rather than concerned, was cute. And telling.

"You maybe want to try it on?" I asked.

"What for?" Krissy asked.

"You know what for," I said, waggling my eyebrows.

Finally, Krissy understood. Her eyes narrowed.

Boys

. Somehow, I could always tell when she was thinking it. I knew further thoughts were building, as well. Excuses. Rationalizations. But Krissy was a realist, thankfully, and she wasn't going to deny her own urges. It was something I'd learned to rely on. She'd suffer through quite a bit if it meant she'd reach her own ends. It was kind of admirable, if you think about it.

"Turn around so I can get changed," Krissy said.

I almost argued with her, but I let it go. If that's how Krissy made peace with this, I was more than willing to sign the treaty. But I did set one stipulation.

"No underwear," I said.

"Duh," Krissy retorted. I didn't need to look to know she was sticking her sexy tongue out at me.

I lay back, eyes closed. I heard the rustling of clothing. Krissy's cute little grunts as she stuffed herself back into her high school outfit. A moment later, she let out a deep sigh.

"OK," Krissy said.

I blinked my eyes open. I'm not sure what I was expecting. A cute girl in a cheerleading uniform, obviously. But this was so much more than that.

Yes, the colors weren't flattering for Krissy (she'd have done better if our school colors were ruby instead of emerald). And the material of the costume was heavy and stiff, more the sort of thing they were sewing in the 1950s.

But honestly? Who fucking cared. Because standing in front of me was an absolutely gorgeous, buxom blonde cheerleader who was down to fuck. It was every heterosexual high school boy's dream come true. When Krissy saw my jaw drop, I think that made it all worthwhile for her.

She grinned shyly, straightening her arms and twisting her shoulders in a way that was meant to be modest but only amped up her sexual energy.

"Does it look OK?" Krissy asked, already well aware of the answer. "It still fits, right?"

Fuck me

.

Krissy must have taken that as a command because she climbed onto the bed and shoved my pants to my knees. Ordinarily, we went right to the good stuff. But this time, Krissy must have been feeling the energy of it because she lowered her head and took my impossibly stiff member into her mouth.

Oh my God it was beyond perfect. Seeing her in that uniform, her innocent mouth contorted around my cock. Golden hair tucked behind her ear. Blue eyes big and supplicant, staring upwards.

It'd been a long time since I had such a hair trigger. Krissy's lips had barely slid up and down my shaft and already I hit my endpoint. The cute blonde coughed and sputtered as I sent my seed. Seeing the white fluid drip onto that pristine uniform only added to the picture.

"Sorry," I said, "Came so quick. Couldn't warn you."

Krissy, however, was smiling. Her cheeks pink. I think she realized the power she had over me in that costume. I know she enjoyed it.

"That's OK," Krissy said, licking my spend from her lips. She gulped, audibly. "I liked it. It was hot."

She looked down at my dick, slowly retreating against my thigh. She made a little pouty face.

"Don't worry, I can get him back," I said. And I knew just the way, too.

I quickly flipped Krissy over. She was so surprised, she cried out. But before she could react further I shot my hand under her pleated skirt and began stroking. My fingers in that most private place solved both my problems. Krissy stiffened as I stroked her, and my own dick began to bounce back, as well.

"Jacob," Krissy said my name like a little prayer. A wish for something more. And, fortunately, I was able to give it to her.

I teased my revitalized hardness at her entrance. Then I realized I wanted something different.

"Turn over," I told her.

Krissy nodded, compliant. I lay on my back and gestured for Krissy to climb aboard. She slipped my hard dick under that skirt (my GOD) and lowered herself down. Her face that intoxicating mix of pleasure and pain.

"Fuck that's big," she said. I figured she'd get used to it by now. But I still hadn't gotten over her saying it, so why should I expect any different?

Krissy began to slowly inch herself up and down on my dick. Her mouth quirked.

"Should I be, like, doing a cheer or something?" she asked. I could tell the whole setup had her feeling awkward again.

"I'm OK without," I said..

Krissy redoubled her efforts on me. She lost her sense of herself, finally, and began humping with abandon. Her thin thighs slapping against mine.

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Then, despite her earlier protestations, Krissy began chanting of her own accord.

"Cum!" she commanded. "Cum in me, you stud. Do it. Cum in your hot little cheerleader. Give it to me. Put it all insssIIDE!"

Krissy cried out as her orgasm overcame her. Her cheeks and chest flushed under the uniform. Her pussy squeezed down, and it was enough to put me over the top once again. I made myself focus, hold off, for one last instant. I forced myself to take in that gorgeous scene one last time.

Krissy in her cheerleader uniform, overcome by orgasm as I stuffed her full of my seed. To this day, I can close my eyes and bring it back to life. Never as instant or urgent as that moment. Yet still as captivating as anything I'd ever experienced.

I could have stayed in that second forever.

*

We stayed on Krissy's bed for a bit; spooned against each other. Krissy curled up in my arms and stared blankly at her pink bedroom walls. Both of us, I think, a little brain dead from what we'd just done.

For once, if Krissy's mom had come into her bedroom, she would have seen something relatively harmless: the two of us fully clothed and cuddling. Well, except for the fact that Krissy was in her cheerleader outfit and my cum was dripping onto her thigh.

Krissy's breathing evened out and for a moment, I thought that maybe she was letting herself feel calm for once. But I quickly recognized it as melancholy. Something was on her mind.

"What happened with your parents?" Krissy asked.

"School stuff," I said. "I told you before, I didn't do so well last year. They're pissed about that."

"Oh. OK," Krissy said, "That's good. I mean not good, but..."

"It's fine," I said, thinking to end it there. But Krissy kept pressing.

"It's only that? It's not me. Right?" I was surprised at how tremulous her voice sounded. "Cause I thought maybe, like, I came to see you and suddenly you're in trouble."

"No, that's not it at all," I said. I turned so I could straight into Krissy's gorgeous blue eyes. Always so judging and sharp. I knew I needed to sacrifice my own ego to satisfy hers. I was oddly fine with that. "It's the grades, like I said. There was all this drama with my roommates and my girlfriend."

"Girlfriend?" Krissy asked. Had I truly never mentioned this? The look on her face was legitimately jealous. It was cute.

"Yeah, I told you about Stacey," I said, "She was wild in, well, all the ways. It wasn't good for me."

"I'm sorry," Krissy said, clearly not at all sorry. In fact, I'd have to say she looked pretty pleased. "So, it's really just school?"

"Yes, that's it. I don't know what I'm doing with my life. I'm trying to figure it out, but- It's not like there's an instruction manual. I'm finding my way through and, honestly, I fucked it up a bit. But it's fixable. It should be fixable."

Krissy nodded, solemnly.

"I guess I thought... Well, maybe your parent didn't want you dating me. Or something."

I did feel bad about lying to Krissy. I comforted myself with the thought that my parents had never truly come out and said it. But we all knew, and here I was telling Krissy her instincts were off. I guess we'd call that gaslighting nowadays. At the time, I thought that I was doing Krissy a favor. She already had that problem with her own family, did she need mine piling on, as well?

"Nope, my parents like you plenty" I said, "The only thing you need to be concerned about is that you have a lazy idiot for a boyfriend."

Krissy gave me an odd look, one I couldn't read. It definitely wasn't the disdain that I expected. It was more... Searching?

Honestly, I couldn't read her at all.

*

We were running out of options. Our safe spaces for sex were quickly dwindling. We tried it in the car again, on Tuesday, but we gave up halfway through. It wasn't working for either of us. Krissy wouldn't agree to sex in the park (not that that was a reliable choice anyway). We couldn't use hotel rooms all the time. So, while our houses were a terrible choice, they were still the best of the worst choices.

And so, despite knowing it was a mistake, we ended up back at my house. So much for staying away for a bit. Fortunately, it was empty, as always. We tumbled into my bedroom. The fact that it was so familiar was both the best and worst thing about it.

Stripped naked, kissing, Krissy again got onto all fours. I knew exactly what she wanted, and I was excited to take her. But as I lined myself up to enter her from behind, she held me back.

"I want to try it the other way," Krissy said.

What other way was there, exactly?

"You know, like, higher."

Now I really was confused. Krissy shimmied her backside.

No.

There was no way.

"I want to try it there," Krissy said, "You know. In my bum."

Holy fuck. Well, that was something I never thought I'd hear her say. Fortunately, logic overcame my urges. For once.

"No," I said, firmly.

"What?" Krissy glanced back at me, a look of genuine confusion on her face. "Why not? I thought all boys love doing that."

"Who told you that?" I asked

"One of the girls from camp," Krissy said.

Man, I really

have

to meet these camp friends!

"Well, I can tell you that's not true," I said, "And regardless, I won't do it."

"Have you done it before?" Krissy asked.

I had to admit I had, a couple times with (again) the crazy ex. And it wasn't bad? I mean, I enjoyed it, mostly because it was something different and she was willing to let me rather than anything about anal that particularly appealed.

But mentioning my ex again was a mistake. I could see it only strengthened Krissy's resolve. So, I repeated my conviction: I wouldn't do it with her.

"Why not?" Krissy asked, little girl whiny.

"For one thing, we need lube to make it work and we don't have any."

"I'm sure we can find something," Krissy said, "In the kitchen or whatever. Like, canola oil or something."

"More importantly, you won't like it," I said, "And then you'll get mad at me for doing it to you."

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"I won't Jacob, I promise," Krissy said, "I want to try this. So bad."

Krissy was a terrible liar. But once she got a hold of something, I knew she wouldn't let it go. Finally, I surrendered. I let out a deep sigh and pulled on my boxers before heading downstairs to see what made sense.

Ten minutes later, my dick dripping yellow with lubricant, I aimed myself right at Krissy's tight back hole. Still on all fours, her head buried in her arms like she couldn't bear to watch. Her whole body was tight.

"Just relax," I said.

"Uh huh," Krissy said, not easing for even a moment.

I closed my eyes and let out a deep sigh. The things I did for my girlfriend, I swear. Using my hand to hold myself in place, I gradually pushed forward. I felt her sphincter start to give, then push back.

"

Relax

Krissy," I repeated.

"I

am

relaxed," Krissy said through gritted teeth. Oh yes, the romance was real. "Shove it in me, dammit."

Again, I steered my dick and pushed forward. This time, her anal ring started to give way. I'd underestimated the slipperiness of my dick and as soon as I had purchase *squip!* I was sliding in.

"OH!" Krissy gasped.

"Ahhhhh," I groaned, feeling her body flex around my shaft. Holy fuck she was tight. Something about my dick spreading Krissy's ass -- the innocent girl so fully debauched -- it started to break my brain.

I drew back a little bit, then started to press forward.

"Oh God," Krissy cried out, "Is it over?"

"I barely even started," I said.

"Fuh-fuck. OK. Keep going," Krissy said.

"We don't have to do this," I said.

"Keep. Going," Krissy growled.

"Is this about my ex-girlfriend?" I asked, "Are you trying to, like, compete with her? Because you need to know, Krissy, you're better than her in every way. It's not even close. Like comparing Mount Everest to a pebble."

"I'm the mountain in this metaphor?" Krissy asked, not kindly. Her ass flexed around my cock, like it was choking on it.

"Yes, Krissy," I said, "There's no competition."

"OK," Krissy said, "Keep going, though."

"You're sure?"

"Yes," Krissy said, "I want to do this."

I thought about telling her to rub her clit, but I decided I'd already pushed things further (both metaphorically and in actuality) than I ought. So I drew back slightly and penetrated forward.

Krissy yowled, like a cat being gutted alive. She arched her back, her butt clamped down, desperately trying to expel this new invader. She screamed. "Take it out! Take it out!"

I pulled out of her immediately, with a wet pop. Krissy fell forward, immediately falling into the fetal position. Face buried.

"I told you," I said, my dripping yellow cock pointing accusingly.

"Fine," Krissy said, "Whatever. Don't ever fucking do that to me again." She curled her legs under her peachy butt, protectively.

I shook my head and went to take a shower and wash myself off.

*

"Do you believe in God?"

It was after midnight, and I was lying back in bed. My bedroom was dark, except for the flyingtoaster screensaver on my computer monitor. The big cordless phone was sweaty sticky against my ear.

Krissy and I had been talking for over an hour, which was mostly just extended silences broken by banal, meaningless conversation. Then she asked that question, which told me where her mind was really at that evening.

"Which God?" I asked, warily thinking she must mean Jesus. I gave an involuntary shiver. Good Jewish boys (and even lousy ones like me) were intrinsically predisposed to dislike that guy.

"God God," Krissy said, "There's only one, Jacob." As if this were obvious on its face.

I was about to snap respond 'no,' but I stopped myself. Krissy had asked the question in good faith, literally. The least I could do was answer her.

Do I believe in God?

I remembered back to a time, a few years before, when I'd gone to Israel with a bunch of other teens my age. Our respective temples had sponsored us all to go for a month. We'd traveled all around the country -- through the hills of the Golan and down the urban streets of Tel Aviv. Slept in Bedouin tents and at kibbutzim.

I had a vivid memory of our visit to Jerusalem and the Wailing Wall. I remembered touching my hand to the warm, ancient stone. I'd felt it then. The old bricks thrumming with something more. The presence of something beyond me.

I'd stopped going to temple services as soon as my parents gave up on dragging me there. I didn't pray. As to the idea of God, I didn't believe in the character from the Bible. Or the old man in the sky. But did I believe in some all-powerful being beyond my comprehension? In something greater than myself? Yes. I know that might seem weird. But I did.

Krissy 'hmmed' when I told her. I thought she'd be pleased with my answer, to know I wasn't a complete heathen. But instead she made that noise. Like she'd eaten a piece of sour fruit.

"Do you?" I asked, "Believe in God?"

"Of course," Krissy said, reflexive. Then a pause. A sigh. "At least I used to. I'm not sure."

"What happened?"

"I don't know," Krissy said, "I grew up thinking I was supposed to act a certain way for God. Be a good girl. That God would punish me if I didn't. But here I am and there's nothing."

"Are you saying you think God should smite you for being in a relationship with me?"

"No, Jacob," Krissy said, dismissively, "You're not listening to me. It's like you said before. There's no path. No instruction booklet. We just do a thing, and we live with it. It's terrifying. And wonderful. Like finally being free."

"I'm not sure I understand what you're saying."

"I don't know what to believe anymore," Krissy said, her voice oddly distant.

And for a moment, I thought I heard something that sounded kind of like a sob.

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