A Compassionate Courtesan story

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.”

“Uh, yes...”

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.”

“Little?”

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.”

“Really?”

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. He wasn’t paying the slightest attention.

I broke off my story and smiled at Lisa.

“Well,” I said, “you can imagine what happened next.”

“Tell me.”

I sighed. “Pretty much what you’d expect. Mike fingered Tracey to an orgasm while Carl did the same with Megan. I sat there, listening and watching out of the corner of my eyes as both cheerleaders had orgasms. But I kept watching Coach like I was supposed to.”

“He didn’t catch on?”

“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. Anyway ... back to the story.”

I didn’t masturbate to the memories for almost a day.

The next away game was much like the first. With a nod, Mike invited me to join them. He said my presence kept Coach from getting suspicious. We again took the last seats, with me on the aisle. This time the seats directly in front of us filled up with other couples. Kids further up the bus glanced back from time to time, envy filling their faces. Apparently, word of the opportunity had gotten around.

Tracey and Mike picked up where they’d left off. Kisses. Caresses. Hands under clothes. Tracey came twice, both times with her head buried in Mike’s shoulder.

Megan was bolder. She took her panties off and straddled Carl’s lap. It was pretty clear they were doing more than using their hands. No one seemed to notice but me.

Or maybe it was just that no one cared. The nearby couples were engaged in their own surreptitious pursuits. Coach remained lost in his own world at the front of the bus, perhaps dreaming of a better job or a win.

We actually did win one of the next two games, both of which were at home. I even caught a pass in the second and made a first down before being tackled. Tracey gave me a congratulatory hug after. None of them invited me to the party at Megan’s later that night.

Yet there was a knowing smile on Tracey’s face when I showed up at her class to carry her books. Mike’s eyes twinkled at me when we ran laps at the beginning of practice. As a freshman, I could never be part of their crowd, but with the unspoken looks, I knew I was in.

Our final game required a two hour trip through fields of corn and wheat. To everyone’s shock, we won. I even scored a touchdown on a blown coverage by their defense. I’d like to say it was the winning touchdown, but the score wasn’t that close. Just before we started home, Coach had the bus stop at Tastee Freeze and he bought us all ice cream.

It seemed only natural to sit with Tracey and Mike and Megan and Carl. We licked our cones and huddled close together on the worn wooden picnic table, while the cold November breeze burrowed through open buttons and raised goose bumps on the girls’ exposed legs.

Mike noticed the fervent way I ate my ice cream. “You seem pretty happy to have that cone,” he said, “even in this cold.”

I shrugged and licked around the edge. “It’s the only reward I’m going to get tonight,” I said. “Not like the rest of you.”

Tracey’s face pinkened, but Mike and Carl just guffawed.

“It’s true,” I said, looking at Mike. “You’re lucky. You’re with the most beautiful girl in school.” I turned to Carl and nodded at Megan. “And you’re with the most exciting.” I took a long lick of my cone. “I’m just a freshman.”

“You caught a touchdown today,” Tracey said.

“Yeah. But who didn’t? I’d trade places with any of you in a heartbeat.”

Before anyone could reply, Coach called out that it was time to get back on the bus. We grabbed our coats and trundled toward our usual seats.

Coach didn’t even hide his bottle this time. I’d heard a rumor that he had a job lined up in Wichita in the spring, and maybe he didn’t care. He joked and laughed with Kyle, our quarterback. The couples in the next-to-last seats turned to their own make-out sessions. I savored the cold creaminess on my tongue as my friends on either side nestled in close and exchanged quite murmurs of affection I couldn’t quite hear.

Once again, I interrupted my own story to smile at Lisa.

“Megan blew Carl this time,” I said. “I couldn’t see his dick, but her head was in his lap until he came. Tracey got off too. I wish I could describe it in detail, but this isn’t the place.”

Lisa glanced around, while we were private, we weren’t that private and you never knew if a busybody would complain about a conversation about teenagers having sex.

“Anyway,” I said. “That was normal and I was getting used to it.”

I continued my story.

No one else in the bus looked back.

I slumped in my seat and stared at the ceiling of the bus while my friends cleaned up and talked low together.

“Hey, Terry.” Mike elbowed me. “Do you want to switch?”

“Huh?”

“C’mon,” he said, “switch seats.”

I didn’t understand, but I stood. He slid behind me and I plopped back down between him and Tracey.

“I’ll watch Coach,” he said.

I stared at him blankly, and he motioned toward his girlfriend. When I looked at her, she smiled.

“I won’t kiss you,” she said, “but you can touch.”

My brain failed to process what she’d said.

She took my hand and placed it on her bare thigh. “It’s okay,” she said. She spread her legs slightly.

My eyes went wide in surprise. I looked questioningly at her. She nodded. I turned to Mike and he nodded too.

I once again paused my story. I knew somewhere, someone would cause problems if I actually described how I got Tracey off, in all the glorious detail, and then how Megan sat on my other side and gave me a handjob, which Tracey then assisted.

I tasted my first pussy juice that night, licking my fingers. In fact, I’d tasted both women’s juices by the time we finished, as well as having the dual handjob.

Megan had said I was only the third guy to taste them both. That blew my mind.

The after I’d come, they cleaned me up, we shifted back to our original seats, and that was the end of it.

None of us spoke for the rest of the trip. When we arrived back at our school, Tracey, Megan, and their boyfriends headed off together in Mike’s car.

Tracey blew me a kiss before they left.

Later, back in school, I continued to carry Tracey’s books for a few weeks. She and the rest of them remained friendly, though with football over, conversations and interests turned to other things. My neighbor Tommy got an Atari for Christmas, and I started hanging out more with him. Tracey only wore her cheerleader outfit to school a couple of times for basketball games, but since I didn’t play, all I saw of it was what she wore in the halls. That was enough to keep the fantasies going.

I went to graduation that year. Tracey and Mike were both happy to see me, though Megan gave me the biggest, longest hug. She and Carl had broken up a month earlier when college acceptances had come in. He hadn’t gotten into Nebraska and she had. They fought about their future together and he made some vicious comments that ended up simplifying her decisions.

“Should’ve invited you to our parties,” Megan murmured in my ear during our clench. When we pulled apart, my eyes went wide. Hers darted to Tracey and Mike. “Maybe at Christmas,” she said, low enough to not be heard by the others. “I’ll talk to them.”

When December rolled around, I waited and waited, but the phone never rang. Later, I learned that Tracey and Mike had eloped when she got pregnant. Megan had gotten an internship in Lincoln. None of them every came back to our little town.

But that didn’t stop me from fantasizing about them, nearly every day, for years to come.

“That was your first sexual encounter?” Lisa asked. Her eyes sparkled with amusement.

I nodded. “I didn’t lose my actual virginity until I was 18, with my girlfriend at Prom. We started dating about halfway through my senior year. She wasn’t a cheerleader, though. We broke up after we went to college.

“Because she wasn’t a cheerleader?”

I shook my head. “Other reasons. But my ex-wife ... yeah, that was part of the problem.”

She cocked her head to the side and waited.

“We’d been married for twenty years when I finally told her about my, um, fetish so to speak,” I explained. “She got upset.”

“It seems pretty harmless.”

I grimaced. “Yeah, well, when I said I wanted her to dress like a high school cheerleader, what she heard was high school, not cheerleader. And when she found the pictures on my computer...”

Lisa’s eyebrows went up. “Underage?”

“Ambiguous. I’ve since deleted them, but...” I gave a defeated shrug.

She smiled. “I think we can work with this. Though obviously not tonight, since I’m not dressed for it.”

I chuckled. Only I could make an elegantly dressed woman in a high end bar be out of place!

“Do you have a specific timeframe in mind?”

I shook my head.

“Then let’s talk about other things,” she said as she took a sip of her drink, “and I’ll let you know when I have things set up.”

I relaxed at the implied acceptance of my proposal.

She raised her glass. “To good cheer.”

“Hear, hear.” We clinked glasses and I settled back in my chair, already looking forward to sex with this woman.

To my surprise, Lisa contacted me the next morning. From her tone, and the way she’d mentioned something about ‘finding a uniform that fit,’ I hadn’t expected to hear from her for a few days. When I returned the call, she put me on speaker and introduced her boss, Sherri.

“Hello,” a smooth alto voice said. “Lisa told me quite a story about you. She was impressed.”

I blushed. “Well, um, I’m not sure what to say.”

I could hear the amusement in her voice. “It’s okay. What we were wondering is ... do you want something more fulfilling than what you asked for?”

I furrowed my brow in confusion.

“If you just want an evening like you originally requested, we’ll understand,” she went on, “but hearing your story about the bus, we thought, well, you might like something that addressed the heart of your interest.”

“Which is?”

“Your ongoing, ah, interest in certain forms of dress. I think we could arrange something that would help bring that interest back down to normal levels.”

I sucked in my breath in frustration. “I’m still confused.”

“Can we speak freely, or would you prefer to discuss this in person instead of on the phone?”

Ah. She’s being discreet. “You can talk freely,” I said. “I’m at home and no one can overhear.”

“Oh, good. Well, you have a minor fetish for cheerleaders. Lisa would be happy to play that role, but we thought you might like a more involved scenario—an enjoyable one—that could possibly lessen the attraction of that fetish.”

“Uh, enjoyable? Not painful?”

Both women gently laughed.

“We don’t do aversion therapy,” Lisa said. “I promise it will be very enjoyable. Everything you’ve ever wanted.”

I blinked in surprise. Ethan had hinted at something like that when he’d passed on the agency’s number. Everything you could possibly want, he’d said.

“Sure ... but what’s the catch?”

“It’ll be much more expensive, for one,” Sherri said. “It’ll also take a few weeks to set up. However, we’ll be willing to guarantee your enjoyment.”

“Guarantee? How?”

“You give the money to your friend Ethan. If you’re not satisfied, you get it back. If you do enjoy yourself, he passes it on.”

“How much?”

“Thirty thousand dollars.”

My eyes bugged out and I sputtered.

“Or nothing, if you don’t enjoy it,” Sherri said. She let three heartbeats of silence past. “But you will,” she said. “We are the best, after all.”

I snorted. “For that price, you damn well better be.”

“So do we have a deal?”

I thought about it. I could come up with the money—it’d be painful, but not impossible. The guarantee helped. I could back out at any time. Which reminded me...

“So what exactly is this scenario?” I asked.

“Mmmm, I think it would be better if it was a bit of a surprise. It will, however, include what you were asking for earlier, with Lisa. It will include also include a lot more.”

“Hmmm ... I don’t know.”

“It’s up to you,” Sherri said.

I sat silently, thinking.

“You’ll love my uniform,” Lisa said after a bit. “Sherri’s too, though I fill mine out better.”

My eyebrows went up. Two cheerleaders?