"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.
