When the blonde walked into the bar, she took my breath away. Elegantly dressed in deep blue, she looked like someone stopping by on her way to a dinner date. Which perhaps she was, if I wanted to and was willing to pay. She looked around and broadly smiled when I waved. It didn’t take her long to make her way to my back corner table, with its overstuffed chairs and cozy feel.
I stood. As she approached, I couldn’t help compare her to Tracey. This woman was much older, but she’d aged well. I guessed she was in her forties but could pass for early thirties. They were both about the same height and build, though Tracey had been bustier. Her hair was straighter, but close enough to the same shade to pass.
She stopped about a foot away. “You must be Terry,” she said, her voice confident and strong above the low din from the scattered drinkers.
“And you’re Lisa?”
She nodded. I gestured toward the chair opposite the small table from me. Her eyes sparkled as she sat.
“I have a card for you,” I said, and pushed the envelope across the table. The one with the five crisp one hundred dollar bills between the cheap Hallmark phrases.
She looked at it and raised an eyebrow. When I nodded, she gathered it up and slid it into her purse without a second glance. I was impressed that she didn’t feel the need to check.
“So,” she said, “you’re a friend of Ethan’s.”
I nodded. “Long time friends.”
Ethan had been the one to recommend the very private agency that Lisa worked for. I had my ear to the DC rumor mill as well as anyone and I’d never heard a whisper about it. If he hadn’t invited me to that Redskins game...
She raised an eyebrow pointedly and waited.
“Um, okay. We’re mostly business associates. I’m not sure he’d call us friends, but I certainly think of him as one.”
“He did call you a friend,” she said, “but that he’s only known you three years. Is that ‘a long time’?”
I snorted. “In my world, it is. Most of my colleagues can’t see past the next election. Besides, Ethan and I’ve gotten close since Bush was re-elected.” Many long nights drinking our sorrows after that...
She read the disgust in my face and the corners of her mouth turned up. “You must be high enough up to care.”
“I’m not that high up,” I said. “I mean, I know people who are high up, at least on the Democratic side, but, you know, Ethan and I worked hard ... for nothing.”
“Maybe for nothing,” she said. “Maybe not. Anyway, I understand you have something specific you’re looking for.”
The waiter showed up. Lisa ordered a Long Island Ice Tea and then turned back to me with a smile. I asked for another scotch. She waited patiently.
“Well,” I said, “what did Ethan tell you?”
“Only that you had a specific request.”
I let out a deep breath. I’d been worried for a while that Ethan might gab about my secret obsession. But then, given some of his comments, I was sure he had his own. He’d just been the first person to notice I was watching the sidelines more than the game...”
I looked around quickly to make sure no one could hear. “I want you to dress as a cheerleader,” I said.
Her eyes danced in amusement. “I can do that. But is that all you want?”
I looked at her, confused.
“Many women can do that, for much less money,” she said. “Our agency ... well, we do more than costumes. We try to fulfill the client’s real needs.”
“I don’t get it.”
She shrugged in acknowledgement but didn’t explain. “Why a cheerleader?”
“It’s, um, a little unfulfilled fantasy of mine.”
The waiter returned with our drinks. I took a sip to soothe my nerves and collect my thoughts. I recalled what I’d told Ethan. You told him, why not tell her?
“Well, big really,” I said. “Closer to a fetish. I’ve been obsessed with cheerleaders since high school.”
She grinned. “Now we’re getting somewhere. What happened in high school?”
“It’s a long story.”
She leaned back in her chair. “I’ve got time.”
I nodded. “Back in high school, well, um, I went to a small school, you see, and all the cheerleaders were really hot.”
“They often are.”
“Yeah, well, I played football. Not because I was any good, but because any kid who tried out made the team, you know? Like I said, small school. I was the wide receiver nobody threw to.”
I snorted at my own sorry memories of Homecoming my freshman year. My first target, my first dropped pass. My subsequent benching for Big Alex, of all people. In front of everyone.
“Anyway,” I said, “we had these long bus rides to games. Coach didn’t care what we did in the back on the way back as long as we were quiet. If we lost, which was most of the time, he was in front sneaking drinks from his ‘special’ water bottle.”
“The cheerleaders were on the same bus?”
“Yeah. Small school, remember?”
“So you had sex on the bus?” Her voice sparkled with amusement.
“I didn’t. At least not full sex. But some of the other kids did. And I got to watch.”
I nodded. “Short skirts, sitting on her boyfriend’s lap. If she’s quiet, a cheerleader can get away with it.”
“Ah. Go on...”
I took another drink and began my story.
Everyone loved Tracey Wisenhunt. Besides being pretty and friendly, she was kind, and her kindness infected the other cheerleaders. When I was sitting forlorn on the end of the bench after having dropped that pass at Homecoming, she came over and said it was okay, and that I’d get the next one. Her boyfriend Mike, our running back, came over and echoed her words. Later, Megan, one of the other cheerleaders, did too. It took some of the sting out of the day.
I don’t know what made me do it, but the next Monday I saw her struggling with her books and I offered to carry some for her. We got halfway to her English class before Mike appeared.
He smiled good naturedly. “I’ll take it from here, champ.”
Tracey thanked me with a twinkle in her eyes, and then gave me a kiss on the cheek.
I was hooked.
For the next several days, I ran into Tracey whenever I could. Mike seemed amused at the way I puppy-dogged her, but he just ruffled my hair and joked that it was nice that someone else thought his girlfriend was wonderful. I blushed, but that didn’t stop me from eagerly waiting outside her classes all week.
I knew she had a boyfriend. I knew that as a freshman, I couldn’t possibly compete with a senior for her affection. I didn’t want to—I just wanted to be near her. I wanted her and Mike to like me.
And apparently they did. As we boarded the bus after our next away game—another loss—Mike motioned to me.
“Hey Terry, Come sit with us.”
I blinked, but hastened to the back of the bus with them. We squeezed three into a seat, with me on the aisle, Mike in the middle.
“Look,” Mike said once the bus started to move, his voice pitched low, “Tracey and I want to fool around, and we don’t want Coach to know. Can you keep an eye on him and warn us if he starts coming back?”
I nodded vigorously. As the ride home started, I kept my eyes flicking back and forth from Coach, who never moved, to Tracey and Mike, who passionately made out.
To my surprise, I wasn’t jealous as I watched them kiss. More fascinated, by the way she sighed and fluttered her eyelids, by the way she brushed locks of her hair out of the way. Once, she looked straight at me, but her eyes were so glazed with passion that I was sure she didn’t actually see me.
“Mmmm,” Megan said from across the aisle, about halfway home. When I turned, she grinned at me and waggled her eyebrows. “You’re watching Coach?”
I nodded. She slipped inside her boyfriend Carl’s arms. Moments later, I got to listen to soft whimpers of pleasure in stereo just underneath the chatter from the kids up front.
The bus bumped along the dark state highway, and my eyes adjusted to the gloom. Coach had his bottle in hand; his head sagged against his chest. Slowly, a tangy scent built until it could cut through the pervasive grimy sweat odors.
I looked down. Mike’s hand moved under Tracey’s short cheerleader skirt. She rolled her hips in response, her thighs slightly parted, surrounding his wrist. It dawned on me what I was smelling, even though at fifteen, it was a completely new sensation.
My cock stiffened in my pants.
Megan’s soft mewls on my other side only made my blood race harder. I became lightheaded in the adrenaline, but I remembered my charge—watch Coach. He glanced back only once. Like a good soldier, I waved and kept my mouth shut. He grimaced, but shrugged and returned to his drink. All my attention returned to memorizing every sound that entered my ears.
About a half mile from home, Tracey’s whimpers turned to muffled cries. I couldn’t help but turn and watch as she shuddered and shook, her face buried in Mike’s shoulder. When she looked up, she met my eyes. Hers were glazed in pleasure. Mine were filled with awe.
I didn’t masturbate to the memories for almost a day.
.... There is more of this story ...