Buzz... buzz...
I glanced over at my phone on the bedside table. It was him again. It was late enough, he must be finally drunk and away from his girlfriend.
This had kind of become a routine for us.
Mark was a guy I worked with over the summer at the local country club. It was the second summer we were working together, though we hadn't spoken much until the end of last season, and even that didn't include too much. One time he basically thought I was a girl from behind, then for the final three weeks of the season, he'd made discreet comments to me along those lines. He was the first person to call me pretty, even though he used to only do it in a 'joking' sort of way.
I was always too shy to do anything but blush or laugh along with him. Plus, I was always just so excited he was talking to me. He was older than me, starting his third year of college, he smoked cigarettes and weed, partied, and drove an awesome suped-up Jeep Wrangler. He was the coolest person I knew. He also had a girlfriend, who was super hot, and a bitch. They had been dating for three years, and I had seen her lots of times, but never spoken to her.
I definitely did not have a girlfriend and I had never done anything sexual, even a kiss, with anyone. I was in high school and had never touched alcohol, weed or cigarettes before. And I knew Mark was right: I did look like a girl from behind. I kept my hair long, it was past my shoulders at that time, a light brown that could occasionally curl up a bit. Being 5'4 didn’t help either. The women of the world were not all over me, but I had started to notice glances from men. And having explored many internet chat rooms, well... I wasn’t as naive as I seemed.
Buzz... buzz...
I reached for my phone and read his message. This part was always so exciting.
“Aaww, man. I can’t believe Jackie!” He texted, referring to his girlfriend.
“Oh, now! What happened?” I asked him.
“She bailed on me again!!!” And went on to explain how she had left him hard again.
He normally complained about this to me, normally after he's been drinking, that is. He had fingered her to an orgasm in his Jeep, but she had stopped mid blowjob because she had to get home. He had pleaded with her, his cock out, hard and wavering.
“She hadn't realized it was so late! She, of course, promised to make it up to me again,” he texted.
Which she always did, and it always meant they'd have missionary sex sometime soon.
He “loved her pussy,” he went on, but the “blue balls are killing me.”
“I can’t believe she left you like that again. That is incredible,” I texted back.
“I was close too. Five more minutes and I would've been cumming. She did save me having to clean up a mess in my Jeep at least.”
“How did she save you that?” I asked.
“I would’ve cummed all over my steering wheel and seats. She hates cum.”
Just reading him mention himself cumming had me heating up a bit.
“Oh wow... sorry,” I texted again. “Wish I could help”.
I didn’t realize what I had sent until after. Wish I could help? Oh god, what did I mean? What did he think I meant?
He replied right away, “Oh, really?”
I blushed, alone in my room, reading the text on the phone screen, blushing with a hard on. What should I say?
“Hmm... Yes...” seemed the right thing to say.
I took a deep breath. What did I even mean? What did he think I meant? …Ah, he’s going to think I’m so weird!
“Well, you’re gonna have to prove it,” he wrote.
I could feel my heart pounding in my chest. This was so exciting. I wasn’t sure what he wanted, but I knew I would be willing.
“Ah well... and how?”
“You know you really are very pretty. How about I give you a ride home from work tomorrow?”
I blushed to myself, and excitedly told him I'd love that. He told me there was one thing: if I still wished I could help, then tomorrow after work, before I got to his Jeep, I was to change into a plain white shirt. Then he would know I was still willing. I agreed.
“Sounds good, cutie. I’ll see you tomorrow at work. Sweet dreams,” he texted eventually.
“Yes,” I replied. “Good night.”
My cock was throbbing; it was the first time he called me 'cutie.' I tried to fall asleep, and finally did after a wonderful and very quick jerk off session.
I was so excited that I slept very little. In the morning I packed a backpack with my lunch and a plain white shirt to change into after work. Work was normal but went by painfully slowly. Mark didn't say a word to me all day, and every time I saw him looking at me, I’d blush and quickly look away. Then finally it was after work, and I was standing outside his jeep in a white shirt and my black work pants.
"Hey, hop on it," he said opening the door from the inside.
I stepped up and climbed into his Jeep.
"Thanks," I quietly said.
"Cute shirt." He smiled at me and looked me up and down quickly, leaving me beet red.
"Thank you," I replied as he pulled out of the parking lot. He turned the music on and lit a cigarette without saying anything. I just sat there incredibly nervous and silent.
After about five minutes of driving, he broke the silence. "I know a great spot, it’s right up here."
"Oh, okay..." I stammered, still looking down. He lit another cigarette.
He turned into a dirt road, and after a couple minutes, we came upon a little dock area for dropping boats in the water. He parked the jeep beside a small shack.
"Don't worry,” he told me. “No one comes down around here this time of day."
"Um cool... yes, it’s a good spot," I said, not entirely sure what it was a good spot for.
He reached into the glovebox and pulled out a joint.
"So, what did you mean by wish you could help?" he asked leaning back and looking at me while lighting the joint.
"Oh, ehm... I don’t know. I mean, I’ll do whatever I can to help."
"I had a feeling you'd say that." He smiled at me. “You know my girlfriend hates giving head..." he said, sliding a hand down to his crotch.
My eyes immediately followed his hand and I didn’t respond.
"So…” he went on, “that’s what I really need help with; I can’t handle all the blue balls..." He looked at me, but I couldn’t look up from his crotch where he was rubbing his hand slowly over an increasing bulge.
I didn’t move.