Prom Night Pegging

*This story contains themes of pegging, female domination, bisexual sex talk, and sexual role reversal. If you're seeking something more vanilla in nature, well, don't say I didn't warn you*

Her name was Bridget Ramirez and she was the hottest fucking thing to ever walk the walls of Cheyanne Mountain High School, in Colorado Springs, Colorado.

She was an 18-year-old Senior, reigning Junior Year Prom Queen, ASB vice-president, and standout all-state varsity soccer star, four years running.

She had also come into this Camilla Cabello-esque body, but with somehow an even rounder ass. The sporty hourglass of her body was absolutely perfect, and even her clothing seemed to cling to her body with jealousy. Her mother was Spanish and her father was anglo-saxon, buzzcut, military white.

Students, teachers, janitors, principals, curious girls on her soccer team-they would all stop to gawk when she walked by. She was delicious to her core and she knew it. All it took was a pair of jeans and a button-up blouse and she could fell kingdoms.

For most though, she was also a total enigma. In the four years she had been in high school, she'd only ever casually dated a few guys for a couple weeks at a time. She had never taken a boyfriend. She had never been dragged through the high school dating drama or become gooey-eyed over an older guy. Guys that dated her were cagey afterwards. No one knew why. But many of them wanted her badly still.

And it wasn't for lack of trying. No one could lock her down, even though so many attempted to keep her attention. The guys she had slept with, she had completely ruined. There were rumors about how good she was. Even teachers had heard them.

She was fun and outgoing and super sexy. She was easy to talk to and the sex was always mind-blowing-but then she'd typically lose interest very fast. She wasn't finding what she was looking for. Not exactly. Not yet.

And that was when I transferred in to Cheyanne. I'm Jackson Detwiler and my family had just moved into town midway through the school year as my father was given a prestigious position at the Air Force Academy.

We'd been in Southern California before that but my Dad had been offered a prestigious teaching position at the Air Force Academy and it was too good an offer for the family to pass up.

I was very unhappy to be leaving friends behind so close to graduation, but what was I going to say? This was my Dad's livelihood. Stiff upper lip and such. My very last weekend in socal, my friends took me out for my eighteenth birthday. They used a fake idea to get me into a club and we partied for one final time. It was bittersweet to be leaving once again, but I was happy for my Dad's success.

I saw Bridget on my very first day of school. She was walking out of one of the college counselor's office's and into the main school office area where I was checking in for my first day of classes. She was wearing this cute, brown-and-white blouse that clung to her tan curves like a condom. She tossed her medium length brown curls as she walked down the hall and had just turned to say hi to someone as she rounded the corner, completely running into me as I gathered up a rather large stack of new-student paperwork. Her very pert breasts crashed right into my hands, as I grasped for my things.

We both went tumbling down awkwardly and the papers went flying all over the floor. It was an honest mistake. She felt immediately terrible and began to help me.

"Ohhhh My Goddd! I am soooo sorry," she said, kneeling down impressively low on the floor (considering she was wearing a low-cut cotton skirt and tank top) to help me gather up the spilled papers. I saw a flash of a white thong, as she spread her sexy legs briefly to awkwardly grab one of my folders.

I looked up to see her concerned face, right above her gorgeous line of cleavage and her beautiful green eyes with their long eyelashes waving at me like palm fans. She was mysteriously beautiful.

"No, it's not a big deal, you didn't mean to," I assured her. I was more than happy that she had bumped into me. She was the kind of girl you wanted to bump into you. She looked up to see me staring at her, and gave me a cute, yet sheepish grin.

"Uhh, wait...I don't know you, I'm Bridget. Bridget Ramirez." she offered me her hand quite officially.

"I'm Jackson. Jackson Detwiler." I echoed her introductory tone. "New student. This is my first day, actually," we shook hands. Her hand felt incredibly soft in mine. It felt nice, and a little cooler than my own.

"Oooh, well, sorry, from this point forward I think I'm supposed to bully you. Ya know...new student rules and all," her eyes watched for how quick my reply would be.

"Oh, completely. I wouldn't have it any other way. In fact...I wore my most threadbare shirt because I expect I'll be getting quite a few swirlies today and I like to dry fast. Would you like to be my first?" I asked her, as I bowed my head to her, and she was quite pleased that I was up to the challenge of her banter.

"Oh, yes, that sounds great. Go ahead and meet me in the cafeteria bathroom at, let's say 11:15?" She added on. We were standing again now.

"Certainly. But...there's a problem there," I figured I'd keep this going as long as I could. This was not too shabby a first person to meet on my very first day at a new high school. I wasn't nervous to begin with, but Bridget had been a marvelous surprise.

"What's that?" She countered.

"I don't know where the cafeteria is...or...well, anything for that matter. Cuz, you know..."

"First day, " she concluded.

"First day," I confirmed.

"Well, I'll be honest...I was probably just gonna go hang out in the ASB room for the next hour to avoid government, and then go tease my math teacher into giving me more extra credit work but, what the hell, I can give you the grand tour if you'd prefer." She offered in the most immediately helpful way. Bridget was fun. She radiated kindness and quickness and fierceness. Also she was the hottest fucking thing. I couldn't believe how normal she seemed. It almost didn't compute.

"I would very much appreciate that Ms. Ramirez," I deferred to her directions.

"Well then Mr. Detwiler, let us be off," and she walked in front of me out the back double doors and into the campus quad.

I immediately hit it off with Bridget that first day. We ended up having two different classes together and, between my ASB and various sports interests, she and I developed a fast friendship as we headed towards graduation. We simply saw each other a lot. It was a kind of kismet. I think a lot of people were jealous of me. They didn't know who I was or why their popularity queen was suddenly so buddy-buddy with the new guy.

I think Bridget liked having someone from out of town. Someone that no one knew. Someone that she could sort've claim as her own. Our friendship was genuine and she was by far my favorite part of that last half of my senior year.

Clearly I was insanely attracted to her. But I also wasn't going to screw up this killer friendship I'd begun.

As Senior Prom rolled around, she was between guys again, and didn't really have anyone she was flirting with or even kind of seeing. Neither did I. I hadn't really been looking that hard. She asked me to go with her. I immediately said yes. We were going as friends and we were totally okay with that. We had way too much fun together.

"Honestly Jackson...I think I'd have more fun with you anyway. You've kind of become my best friend this year. It's like, the most genuine thing I've had in a while." She said to me in the sweetest way. I truly adored this girl in every way.

The night of Prom I arrived to pick her up from her place, and almost had a heart attack when she opened the front door to greet me. she was wearing the tiniest lavender mini dress covered in sparkles that showed off her full rack under thinly clung spaghetti straps. Her hair was down and done with streaks of glitter. Her face also had streaks of glitter and dark, shadowed makeup. She was fiercely beautiful. She was a force of nature.

"You look..." my mouth was hanging open flabbergasted at how hot she looked. This did not look like a going-with-a-friend kind of dress. This dress felt much more like a blowjob-on-the-way-there type of affair.

"Sexy as fuck?" She gleamed at me with the most flirtatious smile, "I know." She put a friendly hand on my tailored blazer.

We both had a laugh and gave each other a huge hug as her suspended breasts pushed forward into my body and i secretly died a thousand deaths. She squeezed my arms and I smiled at her warmly.

"You fill out this jacket well, Mr. Detwiler." She said to me, and I gave her a theatrical body building routine which she pretended to be my photographer for. I gave her the purple corsage and she pinned on my boutonniére.

After pictures and goodbyes we were back in my refurbished Bronco and off on our way to dinner.

Bridget was in an amazing mood. We both were. There was something to be said about a friendship this close. We were eating at this Italian spot that Bridget had recommended.

It was the type of restaurant that fills only one room of space with fifteen or so spread out tables. Bridget and I were led to one of the window seats that fit against the front corner on an L shaped cushion bench. We sat adjacent to each other, our legs barely grazing in the below the the tablecloth.

Dinner was amazing. We were thick as thieves. Cracking up all night long. I noticed that she seemed to be getting closer to me throughout the night.

Her leg pressed up against mine under the table and I was trying to keep my cool. Bridget was the type of girl that always seemed like she could be flirting because we were just becoming so close, and she was so friendly in that way. I had to be careful to remember who we were, and to make no assumptions based on the generally frivolous mood the night.

And then something very unexpected happened.

We were back in my Bronco on the way to the dance. It was around 9:00 PM. She had sidled over next to me on the bench seat of my old SUV. I blasted our favorite playlist and rolled down the windows. It was an unseasonably warm night out for March in a mountain town.

"Ya know what Jackson? I know we're only going to Prom as friends, but I feel like we deserve to indulge in all the traditions...don't you?" Her hand slid over the top of my right leg to massage the inside of my thigh. I gulped and looked down at her on my shoulder as her fingers traced the inner seem of my slacks.

All I could do was smile at her with a confused eyebrow. Was this really happening?

"Eyes on the road, Mr. Detwiler," and she slowly worked her hand up to my belt and zipper to undo them. My cock was harder than jail time. She fished out my absolutely bulging seven inches of glory and began to give me the most teasing blowjob of my life.

We were 20 minutes away from the dance, which was being held at a ski resort. I drove slower than I needed to. She knew that. We were both quite focused on our tasks now.

"MMmmmmm, I always wondered how big you were. What a sexy fucking cock this is," and like that she had disappeared down my body, and the hot, wet breath of her mouth was soon licking up the side of my tool, as she jacked me softly against her lips.

She engulfed my cock as I drove, trying my best to maintain my speed in the slow lane.

I wasn't going to last long. Her perfect lips bobbing on my sensitive glans. Her soft hair bouncing in my lap. Bridget sucked cock better than any girl I'd ever had suck my cock. She bobbed on me and I never felt a single bit of teeth. She also suctioned tighter to me than I'd ever had before. Everything felt so soft and so good and it was only about five minutes in that I told her I was going to cum.

She never stopped. Her head continued it's torturously good up and down motion, as her tongue swirled my head like an ice cream cone on each pass.

"I'm cummmming fuckkkk, Bridgettttt!!" I moaned. And she gulped and licked and gulped and licked. She stayed on my cock, long after the shudders had slowed down, as she slowly came up with a satisfied pop of her lips.

I watched her push a drop of cum on her lips into the corner of her mouth and smile at me.

"Mmmm, that is a delicious cock," she mewed, and I died all over again.

"Holy shit! Where did that come from? I mean I'm not complaining but...wow!" I was smitten. She had completely drained me. She looked so sexy there next to me, her face covered in my juices and sweat. She'd already started to readjust her makeup in the car. I was wondering why she'd brought such a large makeup bag. Wow. She'd known she was going to do that probably.

"Welll...if I'm being verrrry honest with you...I think I've kinda had a small crush on you ever since we first met." She said, and my heart grew a couple of sizes when she said that. She was applying fresh lipstick and had her face pressed forward into the passenger side visor mirror as she steadied herself.

"Damn...I had no clue. Obviously you've probably already figured out that I feel the same way," I said back, in a slightly less smooth way.

"I know Jackson. You've been an amazing friend these last few months...but your eyes also undress me every time you see me," she stopped to look at me with a little sass.

"Guilty. Yeah...I'm sorry...you're like the hottest girl I've ever been close with. I just figured you wanted to keep it as friends," I said, feeling a little silly at how obvious I'd probably been.

"I don't think I knew quite what to do with you...I think the moment I put on this dress...I knew I was going to be fucking you on prom night," she said, and my heartbeat started going even faster.

"Oh yeah?" I said with the dumbest smile.

"Yeah silly, but first let's go dance our asses off and make the popular crowd jealous."

We had so much fun that night. We did all the things. Pictures. Talking to friends. Sneaking a flask into a dark corner. Saying hello to teacher's working as dance proctors.

We didn't rush it, even though we both knew where the night was headed. When we did finally walk out into the crisp night air, the sweat started to dry on our bodies. We had truly gone all out. We weren't worried about how we looked. The night was all about us and one else.

She hung onto my arm as we walked. My teenage heart was bursting out of my chest.

We got in the car and drove to a lookout point that everyone in the town knew. There were seven cars parked in a line with all the city shining back. I never thought I'd ever be sitting in my car next to Bridget-fucking-Ramirez in a dress that made my cock hard from a mile away. She was breathtaking.

When we pulled up to the spot, she turned up the radio and jumped onto my lap. We began to make out immediately. She wanted me bad. I could feel her urgency. I turned the engine off and the lights went out other than the radio, which was set at just the right volume for car fun as her Spotify playlist set the downbeat.

She fished my cock out of my pants and I went to grab a condom from my wallet. She grabbed it from me and ripped it open with her teeth as her hand was jacking me off. She quickly worked it down my cock with experienced ease. Neither of us were virgins, though I hadn't really gotten much out of her about her sex life, or kinks for that matter. We'd only been friends for a few months. Some things, naturally, came later on.

When she'd gotten the condom rolled onto my boner, she pulled to ensure the little space at the tip, she jacked me in her hand for a few seconds longer and admired the throbbing size in her grip. The thin condom was barely noticeable as she touched me. She kept biting her bottom lip and arching her neck.

"Take my panties off," she said, as she leaned back on my steering wheel, spreading her legs up towards me. Her red-bottomed, all-black heels were pressed against my seat, holding my chest in place. Her entire outfit was a sexual mood. I pushed the seat all the way back which gave us enough room for our current position. (Yes...I have a sliding, front bench seat. My Dad and I were car fanatics and had decked out this car together over the last four years in the garage.) She mewled when I did that.

I pulled the short skirt up her legs and could already see her ridiculously sexy lingerie panties. She'd clearly known she was going to be doing all of this tonight. They were crotchless, and had four strings running down which attached the waist and small triangle at the bottom, as the string disappeared between her cheeks. Her pussy was perfect, and of course she shaved. She even had one of those little tanning hearts that girls often got. She just looked like sex.

I pulled the strings open, and just like that she was sitting forward on my cock. She impaled me inside of her as her own gushy wetness made her very ready. She groaned loudly at my impressive length and I enjoyed every second of my best friend's crazy hot pussy for the very first time.

"Jacccckkksoonnnnnnn, fuckkkkkkkk!" She loved my cock. She squeezed me with her vaginal muscles and shook on top of me with a zing of all-over pleasure.

We steamed up that car like the hyper-horny 18-year-olds we were, for the next twenty minutes. I was impressed with how long I lasted. She really had emptied me with her mouth earlier that night from the surprise road head.

"Bridge...I'm close..." I told her, as she ground herself in delicious up-and-down circles on me. She was wetter than any girl I'd ever been with, not that I was any sort of sexual poet laureate as of yet.

Her skilled pussy seemed to be milking me through those final bounces on my cock. She undid the straps of her dress to reveal a sheer, frilled black bra, barely holding her erect nipples and C breasts. Her dark brown hair falling over her gorgeous chest looked like an avalanche of pin-up candy. I could see her hard nipples peaking through the sexy design.

She pulled her boobs out and squeezed my hands against them as I moaned into her.

"I'mmmm cummminggggg!" My cock blew up inside the condom and she rode me hard through my second ejaculation, squeezing my tool with her pussy.

"Fuckkk I'm gonna cummm too baby, don't stoppp!" She achingly moaned, and I felt her body shudder all over as she bucked like a bronco on my hips with immaculate passion. I did my best to ram my hips upward to fill her fully through her orgasm. She came with a gigantic intensity that sucked me into its heat.

My hands loosened their grip on her perfectly perky breasts. She was so damned hot and I had just cum harder than I could remember ever cumming.

She kissed me and we made out softly for about five minutes, just enjoying the feel of being connected like that. My cock was still hard inside of her. She felt so good. She felt like young pussy that would be tight for years.

"Mmmm I am SOOO glad you have a good cock," she had her hands around my neck playing with the tufts of my hair. "I was SO hoping you would."

"MMMhmmm. Well you're very welcome," I said, in my own cocky way.

"We're not done," she countered, as a sultry tone returned to her voice. I was so obsessed with this girl.

She pulled her pussy off of my cock and I looked down with a sudden gasp. My still rock hard penis was sticking nakedly through the obliterated condom, cum coating just about everything.

"OHHH!" Bridget noticed now, and she paused and then started to laugh. I was mortified. I'd never had a condom break, and I had cum a ton. "That's pretty funny," she said, biting a finger. I didn't quite see the humor that she did. I cocked my head.

"It is??" I asked, confused.

"Yes. Babe. We're totally fine. I'm on birth control. I don't have any STD's. Do you?" she was so damned cute and unstressed by the world.