Prom Night Pegging

"No," I was instantly relieved. Birth control. Phew.

"Good, then." Her smile was like molten lava.

We made out more as I took the broken condom shards off, hardly missing a beat.

"Lay down on your back," she told me with more of an insistent tone in her voice.

I did as she said. I was wrapped around her finger.

That's when she climbed up onto my chest and placed her pussy on my mouth, her skirt still bunched around her waist. Her knees slid forward so she was straddling my face now. A bunched up sweatshirt on the seat allowed me to meet her at the right angle.

I didn't hesitate. She had a look in her eye that said "Eat. My. Pussy." I began to slurp at the very wet folds as she rubbed her sweet sex on my mouth and nose. She was still drenched in all of our juices. I licked my cum out of her and I heard the way she moaned as she watched me clean up our mess.

"Mmmm, yessss. Fuckkkk, lick that juicy cum out of my pussy, baby. Taste your salty cum for me, Jackson." I couldn't believe how she was talking to me, but I loved it. I'd never heard her like this before. It was shockingly erotic. I tasted my own cum mixed with the sexy fragrance of her teen pussy juices and whatever lotion she used on her skin. I loved it.

I was moaning as I ate her. That's how intoxicating all the smells and flavors were.

"YES Jackson, lick that messy pussy. Eat your sticky cum out of me, baby." She held my hair and pushed my face against her vagina, as I breathed out of my mouth whenever I could manage.

After I'd thoroughly cleaned her up she surprised me again as she climbed off.

"Flip over on your stomach." She said to me. This was something new.

I flipped over and my hard cock pressed into the leather bench seat. One leg went around her back and the other hung down to the floor below the steering wheel.

She sat behind me and i felt her legs grab my upper thighs as she brought her lips down to my ass cheek and lightly nibbled my muscular ass.

"Jackson...have I ever told you you have an amazing ass?" She had moved her hands up to squeeze my naked buns. I looked back over my shoulder at her in the darkness of the car as her sexy face disappeared between my cheeks. Her body was bent over mine now.

Her lips teased barely past my hole, and I felt her place more kisses on my inner thighs and buns. I could feel her tongue slide out to massage all the way up my anus and my taint and then she fully sucked her mouth against my very sensitive perineum. She licked the bottom of my balls and sucked them into her mouth and then came back down.

I was practically holding my breath at this point. My nerves were going crazy, but it felt so fucking good.

The hottest 18-year-old girl in my high school was giving me my first ever rimjob on Prom night, and I was moaning into the worn leather of the seat, in gobsmacked wonder. Every single hair on my body stood like corn stalks, and she was simply whispering into my radicalized brain: "If you lick it...he will cum."

I felt her tongue drag into my crack and slide into my asshole finally. She broke past my sphincter as she slid further into my butt. I had a tongue inside my asshole for the first time and my eyes had completely rolled into the back of my head to search for some kind of new religion, as my cock oozed pre-cream.

"Bridgetttttttt," I moaned her name because I wanted her to know how turned on I was.

Then she was propping me up for more and I watched as she pulled my cock back towards her. this forced me to arch my lower back up as much as possible.

I imagined what a cop would see if he approached and shone a light into the car: my ass, popped and spread, as the high school's It-girl tongued my tightness like a tigress. What a fucking scene we made.

She had managed to get my cock back towards her now and I felt her moving around. She was taking her dress off and bunching it under my crotch to allow me to rest my cock backwards more comfortably towards her. She was still wearing her sexy heels. I had to really pop my ass up so she could bend my boner fully back behind me. She started to teasingly stroke me against the softness of her dress, with one or two fingers rubbing the tight skin of my shaft. I was so hard and she noticed that.

She pushed her mouth back to my ass while she rubbed me and even spit her saliva into my crack and the sheet dirtiness of it made me melt. She was immediately wilder than any girl I'd ever hooked up with.

As she jacked me her lips came off my wet hole and I felt her fingertip run between my buns as she began to stroke my sensitive ring. This was a new kind of sorcery.

I moaned loudly again. I'd never had a girl play with my ass before, much less a girl that this was feminine and this stupidly hot.

Her pointer rubbed spit over my hole—softly and seductively making its point. I felt her rubbing her own juices all over me. I moaned as she did it. I couldn't believe how amazing the sensations were from ass play.

She stopped stroking my cock and reached her fingers into her very wet pussy to collect a sloppy, wet collection of our juices. Then she painted my asshole with all that slop like a brush to canvas.

"You have such a fucking sexy ass, Jackson," And as she said this, I felt her pushing a finger into me for the first time," I groaned out loud and tensed my body as I felt her enter me and my ring tensed to hold onto her intrusion.

"Holyyy fuckkkkk, Briddgget," I oozed out sensual sounds.

"Yessss, Jackson...just relax your body and enjoy the way it feels to be fingered by a girl that's obsessed with your ass." I could tell how turned on she was by the way she moved with me. Her own body was grinding up against me from behind as she worked me slowly open.

Her finger traveled all the way into my very tight hole and I took deep breaths in and out. When I'd started to breathe easier and get more comfortable she began to push in and out. And then I gasped again when I felt her shove a second digit inside of me.

"MMmmmm, such a gooood boy," she cooed at me and I kept my eyes clothed as my teeth lightly gritted in pleasurable depravity. It hurt...but I also was beginning to like it. Her fingers were curling inside of me with a small hooking motion, and she flicked at my prostate before I even knew it was a thing.

"MMMmmmmfuckkkkk," I moaned longingly. Bridget was starting to finger me with a little more consistency now. In and out, as her free hand gently jacked the very base of my shaft with only her thumb and pointer.

"Bridgetttt ummm gonnnnna cummm soooonnn..." I confessed to her in a muffled garble.

"No you're not," she said without missing a beat, and her hand grabbed my balls around their base and squeezed hard.

"Ahhhh!" Escaped from lips, as I again arched my ass up, which further gave her permission to increase the pace she was fingering me. She completely squeezed off my orgasm, denying me what I so badly needed. My ass was on fire. Everything in my loins felt connected and I desperately needed to cum; but only a dribble of sperm drizzled out the tip of my dick.

She rubbed the cum into my hole and kept going.

"Oh my goooodd you're fucking incredible," I moaned back to her.

"I know baby," she fluttered with all the confidence of a sexual butterfly, wildly comfortable and graceful in the power of her demeanor.

She fingered me longer and harder and I moaned louder. We were getting sweaty. She rolled the windows down and continued. Little did I know, but there was a blonde slut in the car right next to ours that was being pounded up against the window, and because they had a taller SUV, they could see my ass through the half-open window, and could see Bridget fingering me, though thankfully in the dark we were only shadows. Bridget would tell me this story much later on. About how she and the blonde traded very sexual gazes while they got their fill. I wondered if it might've been a schoolmate. What would they have thought?

Anytime I'd start to get close, she slow down her grip on my cock and squeezed my balls hard. All while continuing to spit juice into my hole as she pushed her fingers into me harder and harder.

"You like that Jackson?" She asked me, as her hand began to jack me off very hard, and her fingers continued to thrust inside my buns.

"Fuckkkkk yessss Bridget...I wanna cum so badddd."

"Oh yeah? You wanna cum while I finger your ass baby?" She asked me with this insanely sexy tone in her voice.

"Yessssss!" I was drunk for her.

"Cum for me baby," she demanded, and her pussy ground on my leg as she finger-fucked me like one of those automatic fucking arms from the deeper reaches of a porn website. Her hand felt stellar on my cock, and soon I was cumming all over her dress and the seat. It was so much cum. I drained buckets as she flicked her fingers across my titillated prostate with every caress of her hooking fingers. She'd done this before, that much was clear.

I cursed into the car door as the sensitivity became too much and I pushed her fingers out of my sensitive hole. I was shuddering against the seat and felt like I could honestly cry.

She pulled me to her and we made out, messy and without boundaries.

"Shhhh, it's okay...it's okay, Jackson," she comforted me as her beads of sweat lit up her gorgeous body in the moonlight.

"Fuckkkk. Ohhhh my Godddd. Bridget. Fuck." I couldn't form sensible sentences. I was merely words and emotions.

"I know, trust me, I know," she said with a very big smile as she stroked a bit of hair from my forehead, caked in sweat.

"I've never...ever...cum so hard," I was being honest. That was an orgasm for Hall of Fame consideration.

"Most guys don't ever get to see just how fucking good playing with their asses can feel, so yeah, you're not the first guy that's told me that..." she was staring at me in such a sexy way. She was into me. She wanted me. I loved it.

I kissed her again and then she stopped me.

"My dress is a total disaster," she held it up between us in the air, and there was a huge pool of cum on her skirt.

"Look at all of this dirty cum, Jackson. I can't walk around covered in cum," it was like she was challenging me. Like she wanted to see what I would do. I wasn't going to back down from this girl. Not when I was so entranced.

She flicked her tongue out at the dress and some of it fell into her mouth. It was the hottest show I'd ever seen. I brought my lips up to the hem of the dress she was holding. I stuck my tongue out and gathered my own salty cream into my mouth, watching her the whole time. Her eyebrows raised and she smiled. We started to kiss now. Our mouths sucked the rest of the cum off her dress and shared it between us. And then she really surprised me. I felt her grab my head and she pushed me down to the leather seat. There was more cum. I licked the cum off of the seat as I allowed my tongue to taste every single drop. She smacked my ass behind me as she kept my hair firmly pulled and held to the seat.

"Eat your cum for me, Jackson. Show me you love it," and she smacked my bottom again. I groaned wantonly.

When I was done cleaning my mess up she pulled me back up and we made out even more. She was VERY horny now.

"Holy fuck, Jackson...you are so much fucking fun and so sexy and I LOVE how dirty you're being with me," she moaned rapid fire confessions.

"I can't believe how amazing it feels to be so naughty with you." I was so into this girl.

"Take me back to the hotel. I've got a big surprise for you." She said, as she pushed me over to the steering wheel and took the middle seat next to me.

I gave her a big eyebrow as we both hastily threw on our clothes. We clearly looked like we'd been fucking. She smiled at me with so much lust and adoration.

I raced the five minutes down the road to the ski resort-esque spot I'd managed to snag us for the end of our Prom night and we checked in as quickly as we could, fully aware that we looked like a sweaty mess to the hotel check-in desk. We grabbed our bags and keycards and headed up to the top-floor room that looked over the illuminated city below. Her parents were told she'd be staying with friends. They trusted their little angel and had no idea she was a little devil. We were handsy with each other all the way up the elevator and down every hall. She stroked my cock through my pants as I struggled to the get the door open. I pushed her into the room and we started to make out ravenously again.

She was on the bed and she flipped her dress up and I fucked her doggy style for an amazing ten minutes. The sounds this girl made would've had Ophelia Rain blushing. She came on my cock and I loved hearing her orgasm for me.

She pushed me off and went over to her bag. I watched her pull out some toys. A vibrator. A plug. A strapon. Lube.

Holy fuck.

She took her dress off, but once again, left her sexy heels on. Now she was only wearing the lingerie set and her heels. She also put on this lace choker from her bag that I hadn't expected. Her entire look began to become that of something more controlling.

She pushed me back onto the bed before I could overanalyze anything, and then folded my ass up. I felt her drizzle the water-based lube onto my hole and soon she was pushing the medium-sized, silver plug into my hole. I moaned and clutched at the sheets as the fat, glass head squeezed past my sphincter and tightly fastened to my inside, as the base attached to my ring. It really did plug me. The name made sense. It was a crazy full feeling.

Once the plug was inside of me, she sat me up on my knees to make out with her again. She knew what she wanted and she didn't wait for it. I loved this. She was a complete package of certainty and the sexiness of it was almost unnerving.

"Do you like that?" She asked, as she broke our kiss. She brought her hands down to squeeze my cheeks behind me.

"Yesss, I really do, Bridge..." it hurt, but I loved the kind of hurt it was. Not painful...so much as...a necessary pain. The pain you want.

"Good, cuz I've been thinking about your ass all week," She admitted, and I watched as she pulled on the dark red, leather harness over her panties. A thick, six inch dildo swung firmly through the front ring, and soon she was cinching up the straps to tighten everything to her body. She turned on a small vibrating egg that pushed against her clitoris from behind the silicone cock.

She pushed me backwards on the bed and I gulped as her smaller frame seemed to instantly take over. She sucked on my very hard cock as she pushed my legs up and smacked my ass a few times. Anytime she would spank me the plug inside of me would cause my entire crotch to pulse with pleasure. It was such a totally new feeling to have. I looked up at this gloriously hot girl with her dark brown hair brushing her neck. She was a goddess above me. She was Cleopatra reincarnated.

And then she started to pull the plug out of me, even as her lips deep-throated my tool. Once it had plopped fully out, she threw it aside and squeezed more lube from the bottle out onto the toy cock and down my hole. She spread my legs around her and scooted into my crotch, centering her cock at my anal ring.

"Jackson...breathe deep for me baby" I did as she said as I felt her pushing the plastic cock into my body. It was one of those life-like dicks that had all the real ridges and helmet head. It burned when the tip was cresting me, and then it plopped in much like the plug had, but it hurt much less due to how big the plug had been, and also from all the lube, and also because I was so transfixed by her cute face as she smiled at my strain. I wish that wasn't a run-on sentence. But that's how everything felt, like a run-on sentence of nerves and excitement.

"OOommmmfffffff," I moaned loudly, and she brought her body down on top of mine as I wrapped my legs behind her. This was so insanely intimate.

She gave me a moment to adjust to the fullness and then began pushing her cock further inside of me. I was breathing very fast. I was actually going to be fucked by a strapon cock. I couldn't believe it.

"You like that, Jackson?" She asked me in the sexiest alto, as the cock burrowed further into my virginity.

"Yusss," I moaned up at her. She kissed me, and then she fully impaled me, shoving the final two inches in with the squelch of the generous lube in my crack. I clung to her back like a scared cat at first, and she kissed me over and over again, as her strong thighs pushed my legs open.

"Just relax baby, let me have you. I want you so bad," and I did as she told me to do. I relaxed my body, breathing deeply in and out, and soon she was pulling out and pushing back in. "You're so fucking sexy, Jackson. Give me your ass, baby."

Bridget Ramirez, recently crowned senior year Prom Queen, and mysterious object of everyone's affection, was taking my anal v-card on the top floor of a luxury hotel. I noticed how her playlist had changed. It had gotten sexier, and more dangerous. My Body is a Cage bellowed as I panted for her.

She began to grind into me in amazing ovals, and my body slowly got used to the feel of being so stretched. Her movements pushed the cock into my G-spot over and over, and my stupidly hard cock pressed against her soft navel and left trails of my sperm all over her stomach. The cock entered me repeatedly, and forced high pitched moans from my mouth.

"Mmmm, look at how hard you are Jackson...you really like this, baby...give me your ass baby, give it to me." Every word she said made me harder. I wanted to give her my ass. I love how she phrased that. I love how she wanted me. I moaned louder and arched my body up to her. She sat up and began to fuck me harder. Every thrust was timed with her hand on my cock. She jacked me and fucked me and totally took me on this wild ride with her.

Then she was picking my legs up to rest on her shoulders. I watched her lean her upper body back and thrust into me with her own whorish moans of delight, as she listened for every submissive sound suddenly spewing from my mouth to know what I liked the most. She knew what she was doing at every turn.

"Fuckkkkk, Bridgettt...yesssss fuckkkk meeeee fuckkkk meeee fuckkkk meeee I fuckinggg love yourrr cockkkkk!" I honestly had never felt so powerfully turned on by another human being before. She was unlocking me and I said dirty things on cue for her.

"Yesss Jackson...take my hard cock up your slutty ass. Take this big, hard dick baby and tell me you fucking love it," She was bouncing into me, each thrust wanting to go deeper, wanting to fill me more.

"I loveeee it...I loveeee your cockkkk sooooo muchhhh," and before I could even warn her I was cumming.

"MMmmm BABBBBBYYYYY!" She squealed and folded me upwards as she filled my deepest depth with her athletic pegging pounds of pleasure. My cock geysered cum all over my tummy and chest and I kept my eyes closed as I was racked with shaking tremor after shaking tremor. I couldn't remember ever cumming so much in the span of just a few hours. My balls were absolutely emptied.

She slowly let my legs down and fell back on top of me, refusing to take the cock out of my very stretched hole. I loved her hot tits pressed up against my own pecs through the sexy bra, as she held me to her.

"That was everything I've wanted with you for so long," she said, and her lips kissed my chin and nose and eyes and cheeks. I could feel how tightly she was holding the cock inside of me, keeping me full. She wanted me to be at my most submissive.

"How did I not know any of this about you?" I was smiling as I recovered still from the all-over pleasure of my orgasm. I couldn't believe what a dominant dynamo Bridget had been hiding. I don't know what I thought she would be like in bed. In my fantasies she had always been a silly little slut, and yet there I was...spread and taken.