"What's your idea Ryan?" I asked, looking over at him.
I was supposed to be the responsible adult escort for Ryan and a friend to go to his school dance. But earlier that night I had been dressed up in a costume—by Ryan's older sister—as a lady bumblebee, complete with giant tits, a short dress, thigh-high stockings and heels. Ryan's had then essentially used me as a female mannequin to induce his sister into sucking his giant cock while I watched, touching myself, before making out with his sister for his viewing pleasure then making out with him. The day had already spiraled out of control. Now his date had cancelled and he was looking at me with a glimmer in his eye.
Ryan just smirked at me and looked towards the road, driving.
"Ryannn," my voice had a slightly high-pitch whiny sound to it, "what's your idea? What's going on?"
"Shhhhh girl, calm down. You'll see."
I swallowed but clammed up. I knew I wouldn't get anywhere if I just sat there sounding like a broken record.
We drove in silence. Ryan reached up his hand to the back of my head, where he began running his fingers through my now-long hair.
"Just relax, Janelle. It's going to be great." He rested his hand on the back of my neck and started kneading. I felt my tenseness loosen. My head tipped back into his strong hand as he continued his massage.
"You're so tense back here baby. Maybe it's because you're carrying all this weight around."
His hand left my neck and I felt him squeeze my left breast firmly. My eyes flew open and I swatted at his hand. He laughed and I couldn't help but grin, looking over at his young handsome face.
"Here we are baby" he said.
I looked out and saw we had arrived at Thompson High. Ryan's high school and my Alma Matter.
Ryan got out of the car and came over to my side to open the door. "Ryan, what...eeeek!" I was cut off as Ryan wrapped his strong arm around my waist and lifted me down beside him, effortlessly.
After I caught my breath I continued "...wha...what about your date?"
"YOU are going to be my date, Janelle."
I stared up at him, dumbfounded. What? He had to be kidding me. I was a man in his 30's, I couldn't go to a high school dance as a student's date! "Ryan, are you crazy!?"
"Not at all. I needed a date, and here you are, looking fucking sexy as hell."
I blushed, "Ryan...I...don't think this is appropriate..." I stammered. "We could get into a lot of trouble..." One of the reasons I had looked forward to tonight was the opportunity to speak to a few of my former teachers and school administrators from when I was a student, who I knew still worked at Thompson and would likely be working tonight. This was too dangerous of a scenario. They could recognize me!
"Oh...but don't you want to dance with me, Janelle?" Ryan wrapped his hands around me and rested them on my ass over my dress, squeezing hard and pulling me into him. My small body pressed up against his large strong one, I could feel his massive manhood pressing into me. My hands rested on his chest, feeling his huge muscles under the thin green lantern muscle shirt.
The fear drove my resistance on a little further. I said in a small voice, almost a whisper. "Of course I do..." Why did I say that? "But Ryan, don't you remember the conversation we had? About the appropriateness of our relationship."
Ryan ignored me and continued. "Besides, don't you know the halloween dance tradition, baby?" I blinked, staring up at him, feeling his hands kneading my ass. Oh my god. I remembered. For years and years the rumors had generally been that if she hadn't yet done so, a girl would give her boyfriend her first blow job the night of the halloween dance. I had never experienced it of course - I was in college by the time I had my first girlfriend.
He leaned in and whispered in my ear now. "C'mon, it'll be fun Janelle" He nibbled my ear and pressed his pelvis into me. I felt the length of his huge cock pressing into my stomach. I moaned, unthinking, and brought my hands down, sliding over the large contours of his abs. It had been so long since I'd touched him. My hands were just about to make contact with Ryan's cock when he abruptly stepped away.
I almost fell forward but Ryan had grabbed my hand and was holding on firmly. "Let's go." He said.
He started towards the door and I fell in behind him. My dress had ridden up a bit and I could feel the wind against the bare skin of the bottom half of my ass. I reached around trying to pull the dress down with my free hand. I got it over my ass but it would go no further. God this dress was short. What was I thinking coming outside in this costume?
As we walked in the front doors I felt a rush of nostalgia, but not the good kind. High school had been rough for me, full of awkwardness and social anxiety. I had always felt out of place and was always envious of the "cool" crowd. Now, my stomach dropped as we entered the hallways.
I immediately saw Principal Janice Winters standing off to the side, talking to a young pretty redhead I didn't know, likely around my age. Shit—Ms. Winters was principal when I had been at this school as well. She would recognize me!
I pulled at Ryan's arm. "Ryannnn" I whispered. But he continued forward, even walking towards the two women!
Ryan said "Hello ladies," and I felt my world crashing down on me.
They looked up. I watched their eyes and, almost in unison, they both quickly scaned Ryan up and down. I noticed the younger woman biting her lip as her eyes scanned Ryan's exposed arms, resting there. Principal Winters eyes then fell on me. She scanned up my legs, took in my large breasts, then rested momentarily on my face. I looked at Principal Winters, waiting for that flash of recognition. But instead she gave a slight disapproving frown then diverted their gaze back to Ryan.
"Oh, Ryan...Hi..." said the younger one, nervously. Principal Winters replied more sternly. "Please use our names Ryan. That is no way to speak to your principal and biology teacher."
"Oh, of course. Hello Ms. Winters...Hello Sarah..or rather, Ms. Daniels." Ryan said the second name with a grin and I saw him subtly wink at the redhead. Ms. Daniels flushed crimson and looked away. Huh?
