"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?
Ms. Winters had missed the wink because she was looking at me again, suspiciously. My heart began beating rapidly, Shit, my life was about to be over!
She spoke. "This young lady does not attend school here, Ryan."
Young lady?? What was she talking about?
"Yes, Ms. Winters. This is Janelle. She doesn't go here now but she's a recent grad." Fuck -
Ms. Winters took another look at me. "Hmmm...She does look a little familiar... How long ago did you graduate young lady?"
"Oh...just a few years ago?" I said quietly, and in a high-pitched feminine voice—not wanting to ruin the facade. Why was I answering in the form of a question!?
"Hmmm..." Continued Principal Winters, still looking at me disapprovingly. "Very well. You two behave."
I nodded my head vigorously, incredibly relieved to be free from her scrutiny. "Yes, of course, Ms. Winters. Say thank you, Janelle." Ryan said to me like I was a toddler.
"Thank you." I practically whispered.
Ryan tugged on my left arm and as we passed the teachers to the right of us, I saw him reach back and pinch the ass of the biology teacher! Holy shit, I thought.
Ms. Daniels jerked and stifled a yelp. I turned around then, not wanting to have any more interactions with the Principal. I was flooded with relief having made it through that interaction and I clung hard to Ryan's large arm.
We stepped through a door and my senses were immediately assaulted by the party. The gym was full of high school students - some dancing but mostly standing around. Boys mostly stood with boys and girls with girls, with some exceptions.
We walked over to a punch table. As I scanned the room, I took in all the young boys and girls - the girls mostly wearing slutty costumes and the boys mostly wearing geeky ones. I quickly concluded that Ryan was the biggest stud here - and he was with me! I thought in wonder.
Ryan held a drink to my lips "Try this babe." I opened my mouth and gulped it down in one motion, nervous. "Wow" Ryan said. "Impressive swallowing."
I grinned at him, then my gaze fell on two girls standing across the room, looking at us. Shit! They were sisters who lived a couple doors down from me. Why were they looking at us?
"Ryan!" I whispered urgently. "I think those girls might recognized me! They're my neighbors."