Diary of a Horny Student Ch. 06

"What time is the limo picking us up?" I read again. My stomach dropped.

It had been multiple weeks since I had fucked things up with Steph, and in that time I had neither seen nor heard from her. She had agreed to be my prom date if I helped her pass her college placement test, but with the radio silence after what happened between us I had no reason to believe she would follow through on her end of the bet.

More importantly, I already had a replacement date! My best female friend Tara lost her date as well, so we decided to be each other's dates. No problem, everything worked out fine. We were two friends just having each others' backs. There was no way in hell I could in good conscience leave Tara high and dry.

Especially now, after what happened the other night.

Tara and I shared an extremely erotic moment. She and I masturbated to orgasm in full view of each other as we secretly watched Sarah, the girl next door and my longtime crush, get fucked in her bedroom by some mystery man. It was like nothing we had ever experienced together, and made the prospects of our upcoming prom date much, much more interesting. I definitely wanted to go to the prom with her.

But at the same time, I had recently discovered that I had some feelings for Steph, although I wasn't exactly sure what they meant. She had long been the older girl who teased and tormented me, but spending time with her, helping her study, had brought us closer together. I got to know her, and only after I fucked things up with her did I realize that I actually enjoyed her company. I definitely wanted to go to the prom with her, if only to patch things up.

But it was the night before the prom. If I backed out on Tara now, she'd have no chance to find a date, and that would be extremely unfair.

"I think we should talk," I finally typed back to her.

"We can talk tomorrow," she responded.

"I don't want you to feel like you have to go," I sent back, making no mention of my date with Tara. Why didn't I mention my date with Tara?

"I always hold up my side of the bargain," she replied, then followed up with "besides, I already have my dress," punctuated with a winking emoji.

A mirror selfie of Steph in her dress suddenly appeared on my phone.

My cock twitched.

"5 pm" I wrote back

What the fuck was I doing?

Arriving back home from picking up my tux, my step mom Kelly could instantly tell something was plaguing me. I told her the whole situation, conveniently leaving out my burgeoning feelings for Steph, as well as the fact that Tara and I had orgasmed together peeping on the girl next door. She agreed I was in quite the pickle.

"Have you told Tara yet?" She inquired.

"No, it all just happened. I have no idea what to even say to her," I bemoaned.

"Well," Kelly said, pausing to think, "I think you should be honest with her. You know, it's funny, something similar happened to me one time," she said, a slight giggle to her voice.

"Oh yeah?"

"Yeah, it was actually the night I met Sandy and Don. It was in college, and there was this big formal dance, and my boyfriend and I had just broken up that day, so I was totally stranded for the dance. Sandy was a girl who lived on my floor, and she had found me crying, and she said why not go to the dance with her and her boyfriend? I agreed, and that night Don got to stroll in with two women on his arm, and I gained two lifelong friends." she smiled as she reveled in the nostalgia. "Not a bad deal, if you ask me!"

Encouraged by this heartwarming story, I decided to tell Tara the truth, and then to just try and make it work. I hadn't totally considered that this was an entirely different situation with entirely different dynamics at play though; I was too busy telling myself everything was going to be fine. I was also distracted at the lingering wonder of what Sandy must have looked like in college. I would jerk off later that night thinking about her large, womanly breasts sitting even higher and more pert than they did today, and wonder if she was as big a freak in college as she was as a housewife.

The eventual phone call with Tara did not go as well as I hoped.

"So I'm going to the prom alone?" Tara said, incredulously.

"No, not at all, you're still going with me!" I said, obtusely.

"But you're going with Steph now, right?"

"I mean yeah, but--"

"So that means I'm going alone."

"No, no, I'm going with Steph, but I'm ALSO going with you!" I exclaimed.

There was a long silence on her end. She did not match my enthusiasm.

"Listen, Tara, I royally fucked up with Steph, and I really want to try and make things right. I'm sorry this puts you in a tough spot, but I don't see why it has to be anything other than a fun night for all three of us!" I said, selling harder than a used car dealer.

Another silence.

"Is this really what you want, Miller?" She finally said in a low, almost pained tone

"I think it's the best option, and a win for both of us." I said plainly.

Another silence.

"Tara?" I said, wondering if she was still on the line.

I heard a long intake of breath. "Ok, I guess I'll see you tomorrow at five. Goodnight, Tim." she said, a slight crack in her voice. The line went dead before I could say goodnight myself.

"Crisis averted" I thought to myself, feeling like the smartest guy in the world.

But unfortunately, it has been proven time and time again, that horned up teenagers can be pretty fucking dumb sometimes.

The others had already begun to arrive as I finished up getting ready. My tie was a brilliant shade of blue that I thought really made the whole look come together. I straightened it, and after a final once over in the mirror, I headed outside to wait for the limo, prepared for the onslaught of pictures about to be taken.

Meeting me outside were Mike and his girlfriend Kerri, Matt and his girlfriend Luisa, Anthony and his date Kristin, Ross and his date Julia. They were all good friends of mine, but I had been seeing them less and less as they had been exploring the exclusivity of romantic relationships, something I had yet to experience.

I looked over at Sarah's house, wondering if she had left yet. Even with two very real women to accompany me tonight, I still looked forward to seeing her. Seeing her at her most raw the week before had only strengthened my crush on her. She was a fully-formed sexual being now, not just a flicker of a fantasy. Her freckled face, scrunched up in the throws of orgasm flashed across my mind.

My cock twitched.

"So what's the deal, big guy," Mike inquired, snapping me back to reality, "too much longer and Mr. 'I've got two dates for the prom' is gonna be Mr. 'all by himself' at the prom."

He was right. Neither girl had arrived yet, and for the first time I considered that there was a solid chance neither one would. Steph was a legendary tease when it came to me, and Tara...well Tara didn't exactly seem thrilled with the arrangement. My stomach fluttered a bit.

"You've got two dates? Ross exclaimed, joining the conversation.

"Yeah, Tara, and Steph from upstairs," I said. "Long story."

"Do they know about this, or is it going to be a sitcom scenario tonight?" Ross teased.

"Yeah of course they kno--" I started, catching myself as I realized something crucial: I hadn't ever actually told Steph this was happening. After my call with Tara, I had been so preoccupied with stroking my cock to the image Sandy on her knees in a dorm room titfucking Don's thick cock that I completely forgot to tell Steph the deal.

My stomach dropped again.

At that moment, I heard the front door swing open, followed by a short, sharp "oh wow" from Mike. I turned toward the commotion, and there, at the top of the short stairway stood Steph.

I thought back to when she and I had made our bet. She agreed, accompanied by a singular boast that she would "wear something so hot there wouldn't be a soft cock in the entire class." I next thought back to what she texted me last night: that she always holds up her side of the bargain. Looking at Steph now, I could see she told the truth.

Descending the stairs was no less than a goddess. Blonde hair done up to perfection, eye makeup dark and smokey, lips painted a muted red, she wore a black, backless dress that hugged every curve and held on for dear life. Connecting at a point on the back of her neck, the front draped tastefully tight down over her full breasts, split in a deep, alluring V that ran down almost to her navel. Her long neck and the swooping curve of her collarbone were on display. The cut and style of her dress made it absolutely clear she was not wearing a bra. The long gown flowed down loose to the ground from her waist. Each step produced a glimpse of her long, shining, athlete's legs, as the side featured a slit that ran almost all the way up to her hip. On her feet she wore black stiletto heels with intertwining straps that grasped their way across her feet and around her ankles. Completing the look were long, black gloves that ran up past her elbow.

Steph glided past a line of slack jaws, male and female, stopping just in front of me. She looked at me hard, her big, blue eyes accented by the exquisite eye makeup. I don't know if I had realized her eyes were blue before.

"You look, uh...you look..." I stammered.

She cocked an eyebrow and just said "I told you so," followed by a knowing smirk.

"Now, don't you have a corsage for your prom date, Timmy?" she said, holding up her bare wrist.

"Listen, Steph, I..." I started, mouth losing all moisture, but that was all I could get out before a car pulled up in front of the house. The passenger side door opened revealing an ankle-high boot at the bottom of a leg clad in fishnet stockings. A long dress made of big, red ruffles shuffled around it as Tara stepped out of the car.

Short black hair newly cut and styled, brown eyes framed by sharp mascara. A choker around her neck led the eye to her exposed shoulders, and down to the tight corset top with ruffles that hoisted her perfect breasts into drool-worthy cleavage.

It had the vibe of a high-class old western show girl, and Goddamn she looked fantastic, but it was her lipstick that gave me pause. A brilliant shade of blue painted across full lips. It matched my tie.

Her lipstick matched my tie.

I looked at Steph. The hard stare was back, this time directed at Tara.

"After what happened between us," I began, "I just assumed you didn't' want anything to do with me, and Tara had just lost her date, so we decided to go together."

Her stare remained on Tara, who was greeting some of the others on the lawn.

"Once I heard from you I didn't know what to do, so Tara and I decided you would BOTH be my date, and I just totally forgot to tell you," I fumbled out again, leaving out the part that I was too busy busting a nut to the thought of her mom, in college, swallowing her dad's cum.

Steph paused, a deep breath rising her smooth chest, straining her full breasts against the dress fabric.

"And Tara's ok with this?" She finally said, looking back at me now.

"I am," came Tara's voice dryly from beside us. We both turned toward her.

"You look great, Tara," I managed to ooze out.

"Thanks," she said, cracking a brief smile, "but let's get one thing straight--we are NOT both YOUR dates, YOU are both OUR date."

Turning back to me, Steph let an amused smile curl onto her lips. She paused, squinted at me like she was studying a science experiment, then finally said "Like I said, I always fulfill my part of the bargain, so works for me if it works for you."

I exhaled, feeling as though I had been holding my breath for hours.

"Great, great, that's just great," I said as I looked over to see the arriving limo, "let's get going, huh?"

After the requisite photos were finished up, we all started to pile into the limo. I was about to duck in when I felt a hand on my wrist, stopping me.

"You and I have things to talk about later," Steph said in a tone just short of menacing. She then slipped past me and ducked her way into the limo before me. I took one last look back at Kelly for some sort of moral support, but she was too busy laughing and talking with Sandy, Don, and a newly-arrived Brian. Kelly hadn't said anything about going out tonight...I wondered if Brian was there to see her, or to see Sandy and Don.

The ride to the prom was fun. All of us joked around like the friends we were, passing around a smuggled flask of hard alcohol. Tara lightened up once the laughing started, and more than one time grabbed my leg and leaned into me as she giggled. I couldn't help but take in the sight of her perfect breasts bouncing as she laughed. Steph didn't try to force herself into any of the conversations, but she was pleasant, and maintained a sexy aloofness, definitely playing into her role of the "hot older girl."

Leaning over to me, she whispered into my ear, "Mike and Kerri, are they going out?" I looked over at the big, burly Mike, sat next to the much more diminutive Kerri. Her hand never left his leg the whole ride.

"Yeah," I whispered back

"Mmm," Steph sighed, before adding "I wonder what it looks like when they fuck."

I stiffened up. I had known from Mike that they hadn't yet made it past "hand stuff," but that didn't prevent my mind from conjuring up the lewd image of the bigger Mike thrusting into Kerri from behind, his hands gripping her generous ass tight.

"They um...haven't yet," I managed to squeak out.

"I see," she said. Sensing my discomfort, Steph softly chuckled. She was going to make this a long night, I knew it.

I looked over at Tara. Her lips grew tight and she bounced her eyebrows as she met my gaze, and then directed her attention back to the conversation at hand.

We arrived at our venue, which, unimaginatively, was our high school gymnasium. Don't get me wrong, it looked great, and was impeccably decorated, but it was still the same gym we had frequented for the past four years. The parking lot of the school was a sea of limos, and ours joined them after dropping us off at the door.

Lining up for pictures, Steph chose to opt out, saying it'd be better if I took my photo with Tara. Tara thanked her, and there seemed to be a legitimate moment of kindness between them. Steph stood over by the entryway while we waited our turn at the photo stand.

"I can't believe you didn't tell her what was going on," Tara said as we waited.

"I know, I'm a moron, I just straight up forgot," I said. My eyes watched Steph as she lounged by the entryway. One of the chaperones, Mr. Ridley the gym teacher, made his way over to her and began chatting her up. He was a younger guy, and had a bit of a reputation, and clearly wasn't going to pass up the chance to address a gorgeous, lonely mystery girl like Steph.

"So what's this going to look like tonight?" Tara asked, "am I going to get to dance with you, or are you going to be lappdogging Steph all night?"

"Huh? What're you talking about?" I asked, not taking my eyes off Steph. She looked over and caught my eye. Smiling, she became much more animated while talking to Mr. Ridley, dare I say flirtatious. My blood started to rise as I thought about her going home with a hound like Ridley.

Tara saw where my focus was placed, and just laughed. "Nothing, nothing at all," she said, "let's take some pictures.

Finishing up with the formalities, the prom was in full swing now. I knew Steph didn't know anyone here, and I remembered how I felt at Rachel's prom, so I did my best to make sure she had a good time. Tara was a social butterfly who knew everyone there, so I figured she could take care of herself.

Looking around, I found Christine, and we greeted each other in a big hug. I introduced her to Steph, who was very cordial in return.

Christine had on a gorgeous, but modest, yellow dress that left her well-covered, showing very little skin. Pairing up with the ultra religious Bobby Dorf had seemingly suppressed her inner carnal conflict, at least for now. They danced very chastely, swaying and shimmying to a respectable degree on the fast songs, and making sure to save some room for the Lord on the slow ones. I noticed a time or two where Christine tried to pull in close for a more romantic dance, but Bobby was quick to create distance every time. In those moments I could sense the sexual frustration she had inside, and my mind wandered as I thought about what she might do to relieve it.

Getting Steph onto the dance floor, she continued to hold up her end of the bargain by dancing in the most erotic way possible. Running her hands up and down her tight body, swerving her hips back and forth like a sexy snake, backing her ass into me and grinding it on my poor, defenseless cock. I knew it was all for show, but the cavalcade of high fives and thumbs up I got through the evening made it all worth it.

After a particularly energetic number, as the next song slowed down to a more intimate tempo, Steph leaned close to my ear and said "after this song, meet me in the limo--it's time to talk."

I watched as she glided away towards the exit, her ass swaying seductively as she moved. More than one head turned to watch her as she went.

I felt a tap on my shoulder.

Turning around, I looked down at Tara's smiling face.

"Wanna dance?" She said, brushing a long strand of spiky black hair off her forehead.

I held out my hand, she took it, and we pulled each other close for a slow dance.

"She's Putting on a real show, huh? We should find her a pole."" Tara said with a timid chuckle as we rocked.

"Yeah she definitely went all out," I chuckled back.

"So did you guys talk yet?"

"No, she wants me to meet her in the limo after this song. I'm sure she's gonna read me the riot act."

I felt Tara draw me closer. The bones of her corset pressed against my stomach, and her lovely cleavage pushed up even further against my chest. We swayed there in silence for a moment.

"What if I asked you not to go?" Tara finally said.

"I have to," I said, shaking my head, "I have to apologize to her and try to make things right."

"Well what if I want to talk to you too..." she said, trying to drive home a point with her eyes that I was completely ignorant of, "...about the other night?"

"Yeah...we should talk about that," I said softly, my mind thinking back to our voyeuristic, tandem eruption, "but we can talk about that later once I cool things off with Steph, I promise."

The song started to fade out, and I began to get antsy.

"Well then who am I going to dance with, tonight?" She said, not letting go.

My nerves were rising now, anticipating my talk with Steph. I was anxious to head out to the limo, and let me tell you, friends, my anxiety did not express itself in the most positive manner.

"I mean pick whoever you want!" I exclaimed, "You know everyone here wants to fuck you, and you've probably fucked half of them already anyway, so the world's your oyster--no need to wait for me!"

As stupid as it sounds, I'm being totally honest when I said I meant that as a compliment, but judging by the speed at which Tara's hands dropped off my shoulders and a distance appeared between us, my own personal intention was completely irrelevant.

After something that idiotic being said to her, you would expect her head to be on fire, ready to murder me with a stare, but the eyes I looked into after such a colossal blunder weren't angry...they were disappointed.

"So that's what you think of me, huh." she intoned flatly.

I was at a loss for words. I searched my mind for something smart or even honest to say, but nothing came out.

"Tara, I..." I began, but she raised her hand, stopping me instantly.

"Don't even try, Miller," She said as she backed away from me, "don't even try."