Chaperoning Prom

*Authors Note* Thank you everyone for reading, rating, and commenting on my fiction stories that I have been writing, I really appreciate it. The story below is a true story that happened this past weekend between my girlfriend Stephanie (Ski Adventures 1 and 2) and myself. One of the downfalls of teaching at a year-round school is the fact that our prom is incredibly late compared to the usual Mother's Day weekend when most do it, but this story is centered around us chaperoning the school's prom. As always thanks for reading and I look forward to the ratings and constructive comments.

"Would you hurry up?" I yelled from my bedroom.

From the other side of the door, Steph giggled and replied, "You got cum everywhere, it's taking a bit to get it off me."

I chuckled and shook my head, heading back into the living room to wait for her to finish. As I sat down, I thought back to the last few months. Since the second ski trip, Stephanie and I had become a couple, at least in private. We hadn't really disclosed our relationship to anyone at work, although I think some people were starting to pick up on it. We made sure that we kept it professional at school, and we spent most of our "dates" at one another's places, or out of town for dinner or overnight trips. We had talked and decided that later in the summer, once school had ended, we would let things become a bit more public.

Tonight, was going to be the "biggest challenge yet," since we were both chaperoning the school's prom. We had already talked about how seeing the other in formal wear was going to be incredibly sexy, so to take the edge off, we had a quick romp that had led to me cumming all over her tits, rather than inside of her like she preferred, and now led to her taking another shower to clean up.

After turning my focus back to the TV for a few minutes to watch the golf match that I had been watching before our romp, I finally heard Steph yell, "I'm out!"

I returned to the bedroom and found her wearing one of my old button ups that she often wore when getting ready and nothing else; I remarked, "That's not very formal for prom."

She rolled her eyes, "Shut up and go shower, I'm going to get dressed and head out. I told Megan and Kelley I would be there to help take tickets." I pulled her close, kissing her, but no sooner than I had pressed my tongue to her lips did she push me away, "Don't you start, you already had your fun, and you're not going to mess up my make-up."

I smirked and let her go, "I didn't see you complaining earlier."

She rolled her eyes again, "You're right, now go shower, you smell like me and sex." I laughed and gave her ass a smack before heading into the bathroom.

When I finished up about 15 minutes later, I found the shirt hanging off the chair by my dresser and her dress bag hanging on the front of my closet door. As I pulled on my underwear and socks, I found myself wondering what dress Steph would be wearing. While she picked out my shirt and tie, I had not been allowed to see her dress, she told me it was a surprise. I pulled an undershirt on, checked the time, and headed downstairs to grab some leftovers before finishing getting dressed. After eating, I pulled on my light blue dress shirt, my gray suit pants, and the navy tie that Steph had laid out for me. After pulling on my shoes and grabbing my jacket, I made my way out to my truck, and made the 15-minute drive over to the hall where prom was being held.

When I got there, kids were already starting to line up, so I jumped in at the registration table, getting kids name's written down and the cards handed off to our assistant who was going to be announcing the names once walk in started. For the next hour I was busy and didn't have a chance to go inside and check out the decorations. When I finally did get inside, the music was already going, and the kids were on the dance floor.

I looked around and found our administrative staff behind the snack table filling plates and nodded to Steph who was filling glasses of punch. Due to the dim lighting, I could tell that Steph's dress dark, either a black or blue, and was an off the shoulder style that was definitely a bit tighter than her scrubs she wore at work. I smiled at her and winked, then raised my eyebrows to signal I liked, causing her to laugh. I walked behind her and leaned in, "You look hot."

She smiled, "Glad you like. Now go help with other things." I jumped in filling trays with more fruit, veggies, and Chick Fila nuggets. After refilling the refreshments, I spent most of the evening talking with the kids, taking pictures with my students, milling around to keep the dancing as appropriate as possible, and finally helping crown Prom King and Queen.

Like always, after the crowning, things died down a bit, but the dance floor remained full. As a slower song came on many of the chaperones moved to the dance floor with their spouses who were also helping. I approached Steph who was talking to a couple of teachers and said, "Nurse Stephanie, would you like to dance?"

She turned and smiled, looked at the dance floor and said, "Aww Mr. Miller, that is nice of you, sure."

We walked out on the dance floor, finding an open spot towards the edge, I held out my arm and she stepped in, taking my hand while my other hand rested on the middle of her back. We maintained a bit of space to just appear as two friends. She smiled at me, "I wish that hand could be a little lower."

I smirked, "On the small of your back or your ass?"

She giggled, "Either. I would also like to be pressed up against you."

"That'd be nice."

We moved silently for a moment before she spoke again, "That suit looks really good on you."

"You picked it out."

"I know, but that combo just looks sophisticated and sexy as hell."

I nodded, glancing down at her dress and noticed a bit of cleavage peeking out the top that was only noticeable from looking down like I was, "Well thank you, I have to say, that dress is sexy too. Does my tie match?"

She looked up and grinned, "That it does, just something subtle for the two of us."

Her hand that was resting on my shoulder squeeze gently, I smiled and said, "I like that, a secret between the two of us."

"I have another secret for us."

I raised my eyebrows as the song began to end, "Oh really?"

"Yeah, my bra and panties match it too."

I inhaled quickly, causing her to smirk, "Nice."

The music stopped and we let go but before we parted, she said, "I can't wait for you to fuck me tonight."

I felt blood shift to my cock and managed to shake my head and say, "You're going to get us in trouble."

She laughed and shook her head playfully, "Nah, no one can hear us, nor do they know about us."

We headed our separate ways, me towards the refreshment table, then a table to sit down, and Steph heading towards the bathroom. I sat down at the table and propped my feet up, remembering why I teach in sneakers, rather than dress shoes. I played on my phone a bit, checking scores and social media, while talking with kids who stopped by. Just as I was getting up to use the restroom myself and get a refill of my Coke, I saw Steph walking towards me, I stepped out of the walkway against the draping decorations and looked around see it was just us, smiled and said "Hey there sexy."

She smiled back and looked around, confirming no one else was close before replying, "Hey yourself."

She got close to me and lifted her hand, handing me her cell phone. I took it from her and noticed there was something else with it. I turned into the light a bit and saw the other item was fabric. Before I could say anything, she took her phone back and smiled, "I'm going to go start helping clean up, Jeremy asked me to have you go out and do parking lot duty."

Still not registering what was in my hand, I just nodded and replied, "Alright, I'll see you in a bit."

As she walked away, she paused briefly, turned, and said, "You should probably stick those in your pocket Ryan."

She smirked and continued walking; I looked down and realized that I was holding a pair of Steph's panties, and like she had said while we were dancing, they were the same color of her dress and my tie. Luckily it was dark because I'm sure I turned a bit pink. I quickly wadded the panties up in my hand, shoving them into my pants pocket. I watched her walk away, the subtle shake of her ass a bit more pronounced in her figure-hugging dress. As she stepped into the lights around the refreshment table, she bumped into a student, and the shake was even more pronounced now that her panties weren't containing her ample ass.

I sighed, trying to calm myself, and hurried outside before my reaction got worse and got awkward. When I got to the parking lot, students hadn't started filing out yet, so I paused beside my truck and reached into my pocket that held her panties. They were soft and silky, clearly a thong because the fabric was minimal. After kneading them with my fingers, my middle finger found what must have been the crotch because it was clearly damp.

I felt my phone vibrate; pulling it out, I found a text waiting for me from Steph. I tapped the screen to open it, then read, "Feeling your hands on my body caused me to get a bit wet. I went into the bathroom and had to dip finger in. I thought that would take the edge off, but I think it made it worse. Figured I'd just give those to you to relieve the rubbing."

I reread the text multiple times, feeling myself get turned on more with each read. Luckily, before I was popping a tent in my suit, the kids began to stream out of the hall and for the next half hour, I was distracted, telling the kids to be careful, be safe, all the things you're supposed to do as a teacher. As the last kid was picked up, I started back towards the doors of the hall, but only made it about halfway across the lot before I saw Steph walking out with the rest of the administration. I paused and as they approached said, "All cleaned up?"

Our principal Jeremy responded, "All the food and drinks are taken care of. Kelley and the Juniors will be in tomorrow to finish undecorating the place."

"Oh nice."

Our school cop, Eric said, "Well, I'm officially off duty now, anyone want to go get something to eat and a drink?"

A couple people in the group nodded that they would, I subtly glanced at Steph, and she said, "I think I'll pass, my feet are killing me from these heels."

I frowned and replied, "I think I'll pass too. I have to be up for an early tee time tomorrow."

Jeremy laughed, "You're missing out guys."

Steph smiled, "It's fine. After graduation?"

We all agreed that we would grab dinner and drinks after graduation, then as the rest of the staff headed towards a sports bar in the same plaza as the venue, Steph walked up to me, "Walk me to my car?"

Looking over her shoulder to see everyone else within earshot, I replied, "Of course."

We walked towards her Jeep and once we stepped between the rows of cars, I pushed her against the SUV, then pressed my body to hers. Our lips attacked each other, and we kissed passionately until my hand slid up her thigh and between us. As I did, Steph shuffled her feet, allowing me some access, and broke the kiss to moan as my fingers grazed her lips.

She was clearly wet and turned on because my finger was quickly coated, "Fuck you're wet."

"I've been wet since I gave you my panties."

I slipped a finger between her lips and into her wet hole, causing her to moan, I pressed my mouth to her ear, "I have half an urge to take you right here."

She moaned again and said, "At least for a moment?"

It was my turn to moan as her hands quickly forced their way between us as she fumbled with my belt, then button and zipper. With my pants open, she hurriedly pushed me underwear down, allowing my cock to pop free into the cool night air. I looked around and seeing no on, or any security cameras, my hand left her pussy and quickly pushed her dress up, exposing her slit to me and the air.

We both groaned as our pelvis met, I reached under her leg and hiked it up, giving me better access. Steph took my cock in her hand and pressed it against her warm opening, and with a slight push, I slipped into her with a moan. As I pushed against her, she buried her head in the crook of my neck and moaned, "Oh yes." With her pinned against the Jeep, me holding her leg, and her arms around my neck, I was able to rock my hips, thrusting subtly into her, causing her moans to continue, and my own grunts were soon added in.

After a minute or so, we were forced to stop when we heard a car door slam a few rows over. We jerked to a stop and made eye contact. Steph looked at me with pure lust and said, "We need to get to your place ASAP."

I nodded and let out another groan as she squeezed my cock; I pushed into her again and causing her to moan, then gently push me away. My cock slipped free, and the cool night air caused me to shiver a bit. As I let her leg down, she leaned against me and took my wet cock in her hand, stroking it briefly. She looked at me and said, "My pussy is so wet and coated your hard cock."

Hearing her talk so crudely always turned me on, and this time was no different. Through gritted teeth, I replied, "You're killing me babe."

She smiled and let go, allowing me to step back. She gripped the edges of her dress, pulling it back over her ass and pussy before saying, "Pull your pants up and let's go."

I quickly redid my pants; it was a bit of a challenge considering my cock was hard as a rock and doing its best to stick straight out from my body. With my pants back on, I looked around then pressed my lips to hers, kissing her hard and tangling my hand in her hair, pulling it slightly before breaking the kiss and saying, "Get going, you need to park first."

She bit her lip and quickly walked around the front of the Jeep with a pronounced sway in her hips. Once she started the car and put it in gear, I hustled a couple rows over to my truck, climbed in and quickly followed her out of the parking lot. It was a 15-minute drive back to my place and it may have been the longest 15 minutes of my life. I kept staring at Steph's taillights and willing every stop light to be green, luckily, I must have had some good karma stored up because we hit all of them green except the last one, but we were turning right anyways. Steph pulled into the driveway first, and I pulled in behind her. I didn't even have my truck in park before she was out of the Jeep, heels in hand fumbling with her keys and heading towards the front door.

I was out of my truck as soon as I had hit the button, following close behind. By the time I reached the door, Steph was already inside, and by the time I shut and locked it, she had dropped her heals and purse on the couch and was almost down the hall to the bedroom. I kicked my own shoes off and shed my jacket on top of her purse before heading after her, untying my tie in the process.

When I got to the bedroom, Steph was standing at the foot of the bed smirking, "About time you got here."

I rolled my eyes and quickly closed the gap, pulling her against me as our lips attacked each other. As we made out, Steph frantically unbuttoned my shirt, pulling it from my shoulders before working on my pants. All of which was made difficult because my hands which started on her ass had quickly moved to the hem and was working it over her round ass. When she pushed my pants and boxers down, I stepped from them and pulled away for a moment, I smirked at her as she panted from the hurried undressing and said, "I think you're overdressed."

She reached up and slipped her arm through the single strap, then reached to the bottom of her dress which was now at the top of her hips, exposing her clean shaven and clearly wet pussy. Gripping it, she quickly began to work it off her body, exposing more of her body with each passing second, when she finally pulled it free of her body, it joined the rest of my clothes on the floor, leaving her in nothing but a blue bra that matched her panties that were in my suit jacket in the living room.

"New bra?"

She smiled, "Yeah, you like?"

I took her in for a moment, the bra was a strapless and clearly a push-up giving her ample cleavage. My eyes were drawn to the little bow between her breasts and the gap between the cups and the rigid band that was providing her support. "I love it, is it a little small?" noticing that she was spilling out of the top a bit.

"One size smaller to make the girls look better."

I closed the gap and pulled her against me, we kissed again, and I quickly undid the two hooks in the back, then pulled it from between us, feeling the firm poke of her nipples against my bare chest. She moaned into the kiss as she pressed her naked body against mine; when we finally broke the kiss, I finally answered, "They look great no matter what."

She smiled, "I'm glad you like it."

She reached down and grasped my cock, causing me to moan, but I pulled away as she pouted. I shook my head and said, "None of that, I already got a great blow job."

She smirked, "And you made a mess."

I laughed, "You told me to make you a glaze donut."

She burst out laughing and we laughed for a moment, just holding each other until I said, "It's funny now, but at the time it made me cum so hard."

"I know, and it felt good. Now why can't I feel you?" she added with a pout.

I moved around her and lay on the bed, "Because I want to taste you, sit on my face."

She groaned, then straddled me after we both got on the bed. As she lowered her pussy to my face, I took a deep breath, savoring her arousal and as I stuck my tongue out, I heard her say, "Eat up baby."

I let out a laugh, but it was soon stifled by her pressing her wet lips to mine. I gripped her thighs and dipped my tongue into her folds, savoring the wetness that coated it. I began to lick around her lips, sucking them into my mouth and even with her thighs on either side of my head, I could hear her moans. As I teased her clit with the tip of my tongue, she began to grind her hips into my face, causing my nose to slip between her lips, engulfing my senses in her wetness. I took a short breath and tongued her clit, causing her to moan louder and begin to shake and squeeze with her thighs for stability.

Guys always talk about if there was a way to go, it would be with a beautiful woman on top, and I don't disagree, but as I sucked her clit into my mouth, and her orgasm began to coat my face, Steph fell forward with a loud moan and allowed me to take a full breath for the first time in a few moments. As she continued to shake in orgasm, she went from sitting on my face to basically laying on top of me. As I greedily lapped up her wetness, I had to pause and let out my own moan as I felt her mouth wrap around my cock.

For the next few moments, I tried my best to continue eating her pussy, but was struggling due to her attempting to suck my soul out through my cock. Her moans from my eating caused a vibration to run through my cock, intensifying the sucking. To get her to stop, I nipped her clit slightly, causing her to break the suction and let out a long moan. I pulled my lips free and said, "Okay, you've gotta stop."

I heard her giggle, then felt her swirl her head around my head before saying, "Why?"

"Because I'd really like to make you a cream filled donut tonight."

We both burst out laughing again at the absurd comment and she rolled off me, rolling side to side as she laughed. When we both finally calmed down, we sat up and she climbed into my lap. We began to kiss, which quickly turned into her grinding into me, causing my cock to run between her lips, coating it in her wetness. When we broke our kiss, she scooted back, reached between us, and grabbed my cock; with quick aim, she guided herself onto my cock, sinking it into her in one smooth motion as we groaned in unison.

With me fully inside of her, she adjusted her legs, locking them around me and began to rock, more grinding her clit against my pubic bone than allowing me to thrust. As she did, I ran my hands up and down her back, before settling them on her ass, squeezing as she rode. Steph tossed her head back in a moan, pulling her torso from mine and exposing her breasts. I began to pepper the tops of them with kisses and little bites, that only increased her moans. She began to speed up slightly and I began to knead her ass; she paused for a moment and took a deep breath before saying, "I need you to suck on my tits."

"Gladly." She moved her hand from my neck, and lifted her left tit, allowing me to greedily suck the nipple into my mouth.

She groaned, "Yes," and began to move again. I sucked and nibbled on the tight nub while continuing my groping of her ass. As she sped up her movements, my hands gripped tighter, and I began to pull her into me. By doing so, my fingers slipped between her cheeks, and one grazed her asshole, causing her to moan loudly. We had talked about ass play, but never actually done it, so as her moans increased in consistency and volume, I continued sucking her nipple while running my finger around her asshole. With a groan and a final "OH FUCK!" Steph pressed against me, causing her nipple to fall from my mouth and began to orgasm.

Her grip around my neck tightened, pulling my face to between her tits; I tightened my grip on her as she began to moan and shake, her pussy contracting around me as her orgasm rolled through her body. As it began to taper off, her moans were replaced by shallow breaths until she lifted her head and said, "Fuck that's good."

I grinned, "Glad I can be a living dildo for you.:

She laughed and nodded, "You know you're more than that, plus we both know my dildo can't suck on my tits and finger my asshole at the same time."

I chuckled at the thought of her dildo. We had used it a few times, me pumping it into her pussy while she sucked me off, I had wondered if she ever wanted to have a threesome, but she had put that to rest, saying she only wanted me. I was pulled back from my thoughts with a groan as she laughed and squeezed my cock that was still buried inside of her.

We both laughed and I asked, "Touching your ass was okay?"

"It was more than okay, maybe sometime you can stick a finger in."

I nodded and replied, "You just tell me when."

She nodded and replied, "Not tonight, tonight I need you to fuck me hard."

I flexed my cock, making her moan before saying, "Well, you're going to have to move for that to happen."

She bit her lip, nodded, and climbed off me. As she sat beside of me, she looked down at my cock and said, "Fuck I am wet."

We both looked down and my cock was glistening in the light of the lamp on the nightstand, and around the bottom was the thick cream of her orgasm. I groaned as she took my cock in her hand, lightly stroking it with no friction due to her wetness. She reached over and cupped my balls, rolling them in her hands before saying, "Are these nice and full for me?"

I groaned and nodded, "Maybe fuller than earlier from being turned on all night."

Steph groaned and squeezed my cock before letting go, "Good, I can't wait for you to fill me up."

I inhaled sharply, trying to put a sentence together and finally said, "How do you want me to fuck you hard babe?"

She smirked, "You know there is only one answer to that..."

"From behind?"

"Of course."

She leaned over and kissed me, then turned around so her ass was facing me, and she faced the end of the bed. I rose to my knees, the crawled behind her into position between her legs. As I've said in earlier stories, Steph isn't a twiggy, Instagram type of girl, she's got curves, and a little bit of extra weight, but she's still stunning, and she's confident in herself, making her even sexier. Seeing her on all fours in front of me, with her ass up and pussy slightly gaping, waiting for me made my breath hitch a little.

I pressed the head of my cock to her waiting pussy, pausing to relish the warmth before pushing into her. I pushed into her firmly, causing her to grunt. I put my hands on her hips, pulling her to me until I bottomed out, and we both groaned. I slid out about halfway and then pressed back into her, pulling her ass up and against me; with this motion, Steph lifted her head, arched her back and let out a long moan. With her body in the new position, I shifted my focus from her ass that jiggled slightly when I thrusted into her, to over her head and smiled.

I grunted, "Open your eyes." Steph did because I could now see them, my dresser was located at the foot of the bed against the wall and mounted to it was a mirror.

She groaned, at the sight of us, "Fuck that is hot."

I nodded in agreement, with her back arched and head back, I had a great view of her round ass, and her tits, hanging down. I again slid out partially before thrusting back in, causing her to close her eyes and open her mouth in a moan. Now, not only did her ass jiggle, but her tits swayed too. I began to thrust, slowly at first but then began to speed up, eliciting amore moans from Steph and grunts from me.

Watching myself fuck her in the mirror was one of the hottest things I've ever experienced, and I am still not sure why we had never done it before. As I thrusted harder and faster, Steph's eyes shot open, and she let out a "FUCK!" and then her eyes slammed shut and her body began to shake as another orgasm began to wash over her. I didn't slow down, instead kept thrusting, prolonging her pleasure, and loving the pleasure that was flowing through my body. Her orgasm seemed to last longer than normal and was very intense because she dropped her head and shoulders to the bed, shaking in pleasure.

The new angle caused even more pleasure to ripple through my body, causing me to speed up and press down into her. As the shaking of her body began to slow, Stepp continued to make small noises, but those were soon drowned out by a long, almost animalistic moan from me. With her orgasm subsiding, Steph reached her hand back and cupped my balls in her hand. As I continued to thrust, she fondled them in her hand, and soon she turned her head and said, "Come on baby, fill me up."

I grunted and thrust a few more times and with a loud moan, I pressed my cock deep into her and my own orgasm hit me. I felt the first shot leave my cock, then the second, and as I began to see little spots, Steph began to moan with me. I now realize that as I began to cum, she let go of my cock and began to rub her clit, sending her over the edge of her 5th orgasm of the day.

We moaned in unison for a few moments, then both our orgasms began to wane. As her body stopped shaking, I bent over, resting against her ass, and resting my forehead against her back, trying to catch my breath. Our moans were replaced with the heavy breathing of us catching our breath, Steph was the first to speak, "Damn that's good." She added a shake of her hips and ass, causing us both to groan.

I nodded my head and added, "You're telling me. That thing with my balls..."

She laughed, then raised up, looked over her shoulder and said, "You liked that?"

"I loved that, made things so intense."

She smiled, "I'm glad, I'll keep that in mind."

My cock was beginning to soften, so I gave her ass one more squeeze, then slowly scooted back, causing us both to groan as I slipped from her. With us no longer connected, Steph collapsed and fell onto the bed, landing on her side. I chuckled at the sight of her upside down, she opened her eyes and looked at me, "What?"

I shook my head and lay down with my head on my pillow, then said, "Just you upside down."

She exhaled a big breath on my feet causing me to twitch, and her to giggle, "What, don't you think we should sleep upside down?"

I shook my head, "No, you would lose you pillow, then you would steal mine."

She stuck her tongue out then rotated, dropping into what had become her side of my bed. She smiled, "There, is that better?"

I smiled back, "Yes, do you want a towel?"

She shook her head, "Naw, I'll wash sheets after you leave in the morning."

"Alright. You going home before work Monday?"

"Not unless you want me too. I have scrubs in the drawer."

"Only if I come home to you dressed scantily holding a cold beer."

She shoved me gently and shook her head, "We just had sex, and you're already thinking about more?"

I leaned over and kissed her, then pulled away and said, "Well, when your girlfriend is as hot as mine, it's easy to think about."

"You're a loser." She said with a shake of her head. She leaned back over and kissed me again, then said, "Alright, I'm double wore out, I'm going to sleep."

I smiled and gave her another pick and said, "Alright, I'll be quiet in the morning."

"Good, because if you want scant dressed me, I need my beauty rest."

I laughed and she rolled over, scooting against me and I rested my hand on her bare hip a squeeze, then said "Goodnight baby."

"Good night."