The High School Reunion

Prologue

One act of teenage gay sex haunted Will Clark for all of his adult life. It affected his efforts at forming long-term relationships with women. Then he attended his ten-year high school reunion, and his life changed again.

All characters are at least 18 years old. Also, there is NO heterosexual sex in this story.

Chapter 01

I sat at my desk in my office reading an invitation to my 10-year high school class reunion. Initially, I elected not to go. I was the founder and CEO of a wildly successful small computer services company. I had taken my teenage obsession with computers and turned it into a business.

I had arrived; why should I want a reminder of the worst time in my life?

High school was a terrible time in my life, filled with struggles and ridicule. I was a skinny, pimply-faced computer geek sporting oversized eyeglasses with lenses akin to Coke bottle bottoms. The target of seemingly endless pranks and practical jokes, I felt the weight of humiliation even from my teachers.

I had zero success getting laid. It wasn't until my second year in college that I finally had my first sexual experience, and she was drunk!

Over time, the acne disappeared, and I filled out and started a successful career in IT. I had Lasik surgery and ditched the glasses.

I would never be the male version of a runway model, and though unmarried, I was reasonably successful in my sex life. I finally figured, what the hell, why not go?

The dinner/dance was held in the gym and cafeteria, with the attendees able to tour the school and see their old classrooms.

My first revelation was that my other graduating class members, while reasonably successful, weren't seven-tall supermen with trophy wives. The star quarterback of the football team who took great pleasure in ridiculing my physique was an overweight, potbellied CPA. His wife looked like a dumpy version of Morticia from the Adams Family.

The captain of the cheerleader squad, the girlfriend of the star quarterback, attended with her fourth husband. Rumor had it in high school that she was a party favor for the entire football team. Her quarterback boyfriend used her as a reward for outstanding players. Discreet inquiries at the reunion revealed that she was still vacuous and promiscuous with enough kids to start her baseball team.

I was smugly surveying my former classmates with a red Dixie cup of overly sweet punch in my hand. Time was the equalizer; I was at least on a par with my former classmates.

Chapter 02

I saw a leggy vision in a micro leather miniskirt working the room. She had the proverbial ass to die for, legs that went on forever, and an ample bosom. She spied me watching her and made her way toward me with a big smile covering her face.

She wore sheer nylons and a semi-translucent chiffon blouse that barely concealed a black bra desperately trying to contain breasts that were at least a large C-cup.

"Will Clark," she asked in a throaty contralto, "is that you?"

Her name tag said her name was Calista. I instantly reverted to my high school persona, stuttering as I answered.

"Y..yes...uh...Calista. How are you?"

I wracked my brain but couldn't think of any girl in high school who looked like this and who would remember my name.

"You don't remember me, do you?" Again, the throaty laugh as she daintily covered her mouth with her hand.

" I'm sorry," I admitted, "but no, I don't."

" My name is Calista. You knew me as Mike.".

I stared blankly for a minute, and then the light went on in my head.

"Mike Jones? "The guy I used to play video games with?"

"The same," she said with a slight bow that caused her tits to jiggle disturbingly.

I was surprised to see "Calista." The last time I saw her, she was a he, and he was giving me a blowjob, my first!

The back story is that Mike and I gravitated toward each other in high school because we were both geeks and outcasts. We spent hours together doing homework, playing video games, and watching Internet porn.

Over time, we began masturbating while we watched porn. That graduated to mutual masturbation and to "Mike" sucking my cock.

We were watching porn videos on my laptop while jacking each other off. Mike was particularly good at jerking me off. He knew how to apply the right pressure, and his thumb stroked the nerve-packed area under my glans.

Mike's eyes flicked from a scene on my laptop where a mother was sucking off her son to watching his hand stroking. He told me later that he had thought about sucking my cock for a long time but was frightened to ask me.

I had similar thoughts but was also afraid. I was confused about my sexuality. I looked forward to Mike and my jerk off sessions but I worried that others might find out and call me gay.

Usually, I licked his cum from my hands after I jerked him off. The taste was intoxicating! The more I ate his cum the more concerned II became that I was gay.

This evening I was close to cumming. I had stopped stroking Mike's cock and was pumping my hips, ready to explode.

His eyes flicked from the scene on my laptop to the look of ecstasy on my face to my cock leaking copious quantities of precum. Just as his stroking me got me close and I closed my eyes, he leaned down and took my cock in his mouth.

I was so far gone that it took a moment to realize he was sucking me. When I did realize it, there were no protests, no snatching my cock away. The feeling was incredible, and I gripped his face and fucked his mouth for all I was worth.

In retrospect, he was an amateurish and inept cocksucker. But I did cum hard and in quarts, and he could not swallow it all. He pulled away, coughing and spitting up cum as I continued cumming on his face. I still recall the startled look on his face, along with a facial of cum.

I collapsed on my back, gasping to catch my breath. Mike crawled over to me and took my still spurting, sem-hard cock back in his mouth. I was 18, young, dumb, and full of cum. Soon I was hard again.

Mike pushed his jeans down and lay head to toe with me like the couple on my laptop. Confused but still riding the intensity of my first blowjob, I took him in my mouth.

In the years afterward, I recalled the exquisite feel of his hard but pliant cock in my mouth. I remembered gripping his sweaty ass and squeezing it as we sucked each other. My finger inadvertently pressed against his anus as I was squeezing his behind.

Mike shrank away, then pushed back, and my finger slid into his anus. When he did my finger found the bump of his prostate. Not knowing what it was, I rubbed it.

He went crazy! Bucking against me and sucking my cock so deep it went down his throat. I twisted my fingers in his ass, massaging his prostate.

He came first, exploding in my mouth. Unlike him, I drank his gooey cum, sucking him as I swallowed. His cum didn't taste that bad. I like the taste and feel in my mouth.

I quickly followed. He squealed as my grip on his behind tightened, and I buried my finger past the second knuckle in his starfish when I came the second time.

Mike rolled on his belly, exhausted and like me, overwhelmed with what we had done. I lay on my side leaning on one elbow staring at his slim ass. In that moment, I wanted to fuck him and it scared me.

A wave of realization crashed over me as we lay next to each other, struggling to catch our breath. The weight of our actions, of what I had just done, bore down on me.

I had just sucked a cock and let him cum in my mouth. Did that make me gay? Did I want to be gay?

Mike whimpered when I caressed his sweaty ass and my finger probed his boy pussy.

"Are you going to...!"

He couldn't finish the sentence but we both knew what he was saying. Did we want to take the next step? Should we fuck?

I rolled on top of him and ground my hardening cock into his ass. Mike raised his ass and ground it against my dick.

"You can fuck me if you want to," he whispered, " I want you to."

An overwhelming sense of shame swept over me. It says a lot about my shallowness at that time in my life that I was more worried about what others would think of the pleasure I got from what Mike and I did.

He wanted me to fuck him and I wanted to in the worst possible way. The urge to fuck him frightened me so much that I urged him to dress and leave quickly. I ushered him out of my house and out of my life, cutting off all contact.

It wasn't the blowjob; I later admitted I enjoyed it. It was my lust to fuck him and consummate our relationship. I feared what others would say if they found out a guy blew me, we 69ed and fucked. We graduated a few weeks later, and I never saw him again until now.

Chapter 03

There was an old joke about what you say to a naked lady. I was experiencing the 21^st-century version of that joke. What do you say to a male friend who presents as female?

"Well, I see that ten years have changed you a bit," I said awkwardly.

Calista stood at 5'7" at 120-125lbs with long blond hair, nicely tanned skin, and the most beautiful set of blue eyes.

" I would hope so! I have spent enough money in doing so," she laughed.

From what I could see, it was worth every dime. We had an awkward conversation, catching up on the previous ten years. Finally, she broached the subject that hung heavily in the air.

"I guess you're wondering why I decided to transition?"

I nodded nervously, unable to form the words to ask.

"It's partially your fault. Do you recall that evening in your basement when I sucked your cock, and we 69ed?"

"Look, we were both young and inexperienced...I"

"Well," she said, interrupting me and probably saving me from making a complete ass of myself," Let me apologize for completely botching it. You're right. We were inexperienced. I'm a much better cocksucker now."

She paused, smiling devilishly, letting her words sink in.

I was sweating profusely while scanning the room to see who was watching us. What would they think? In a moment of prescience, I realized my high school class never thought much of me then, so why worry about what they thought now?

"Sucking your cock was intensely satisfying, particularly when you accidentally gave me my first prostate massage. If you hadn't panicked and shooed me out, you would have been my first in all things."

Calista stepped close enough that her perfume filled my nostrils, making me lightheaded. "You would have discovered I'm a Bottom and loved getting ass fucked."

I was aroused as never before. In my limited number of sexual encounters in the intervening ten years, I discovered anal sex and the fact that I loved the feel of my cock in someone's ass. Until now, the someones were female.

"Look, I...!" I began lamely.

Calista placed one manicured hand on my chest, stopping my stumbling rejoinder.

"I was hurt when you shut me off. I guess in my teenage way, I loved you. It took me years to get over it. Thankfully my family moved to another town; else, I would have made a complete fool of myself over you.

"I got into the gay lifestyle and found that I was more trans than cis. I met an older guy who helped me realize who I was. I've never been happier. By the way, Are you going to tour the school?"

"I was thinking about it."

"Why don't we take that trip down memory lane together?"

Amy took my hand, and we left the gym and walked down the once-familiar halls.

We stopped at our old locker. She and I reminisced about the times we shared the locker. We were close, very close, as only two outcasts could be.

"Why do they have a rope across the stairs?"

"The invitation said the tours were only for the first floor."

"My first hour English class was on the second floor, Mrs. Allen's class. Let's go see!"

She unhooked the rope, handed the end to me, and bounded up the stairs. I stood looking up the stairs and under her skirt.

"Calista, no! We'll get in trouble."

She stood at the top of the stairs, grinning with her hands on her hips. I caught myself again trying to peer under her skirt.

"Come on, chicken! Or would you rather stand there and look up my skirt."

There is no red bright enough to match the color my face turned. I replaced the rope and ran up the stairs. My heart was in my throat, not from fear of getting caught but fear of being seen with a transexual. I had grown older but not more mature.

It was dark in the hallway. The only light came from the parking lot's halogen lights shining through the windows that lined the hallway opposite the classrooms. I watched Calista's ass sway as she took my hand and led me down the hall.

"Oh, look! The girl's washroom. I recall in school always wanting to see what it looked like."

She pushed the swinging door open, stepped in, and held her manicured hand out to me. "Come on in."

With my heart in my mouth, I followed her in, and the door swung shut behind us. I walked in slowly, expecting a hall monitor to yell and ask where I thought I was going.

"And this is the other thing I always wanted to do!"

Before I could react, she wrapped her arms around my neck and kissed me. I was surprised by two things. The first was that I didn't resist; the second was how soft her lips were.

Caught up in the moment, I cupped her ass as she pushed me back against the sink and moaned into my mouth. Her hand dropped between us, and she grabbed my cock.

"Calista, I...!"

"Are you going to shut me out again?"

She squatted in front of me, unzipped my pants, and pulled out my cock.

"I...! Oh fuck!"

She inhaled my dick. In one gulp, I filled her mouth and slid down her throat. It was incredible feeling her lips on my shaft, her tongue caressing it. She expertly hiccuped, causing her throat to flex.

I gripped her head as I fucked her mouth. The faint sound of music wafted up from downstairs. It was surreal, getting a blowjob from a transexual in the girls' high school bathroom.

Calista stopped sucking me and stood. She again wrapped her arms around my neck and looked at me quizzically.

"Well," she asked, "Am I a better cocksucker than our first time?"

"Much better," I admitted, looking around nervously, "But we had better get out of here before we get caught."

She ignored my comment, took my cock in her hand, and stroked it. "You know what else I learned besides sucking cock?"

I shook my head. I was caught up in the moment but still scared.

"I learned how to take a cock up my ass! Do you want to fuck me?"

I was shocked at her forwardness. Mike was too shy to look someone in the eye; Calista wanted me to ass fuck her.

"Look, I'm not...!"

"...gay," Calista finished. "And you still won't be gay after you fuck me."

I watched in stunned silence as she unzipped and stepped out of her skirt.

"We had better get out of here before we get caught."

"So you're going to reject me again," she said sadly. "it's like in high school. I finally got the nerve to show you how much I cared for you, and you rejected me. "

She started to cry, and I embraced her, comforting her. She turned in my arms, pulled away, and leaned on the face bowl with her legs spread. Her slim ass, with her cock hanging between her legs looked positively delicious. I ran my hand over her behind, relishing the feel.

"Please, just this one time! I've had other men fuck me, but I always thought about you doing it. Fuck my ass this one time, and I promise I won't tell or bother you anymore."

"Look, Calista, you're still Mike in my mind. I don't know if I could!"

She slipped her skirt back on, turned and walked toward the bathroom door. I was confused about what was happening. Mike and I sucking each other's cock back in the day set off years of confusion about my sexuality.

I enjoyed it, really enjoyed it! I desperately wanted to reciprocate. If Mike hadn't moved, I would have gotten over my reluctance and sought him out. But At least that was the lie I told myself. I was too frightened about what others might say. When we were in high school, just being called gay could destroy your life.

I grabbed her hand and pulled her back into the bathroom. I grasped her waist and lifted her onto the sink. I was scared to death but determined not to reject my best friend again.

I pushed her skirt up, grasped her panties and pulled them down. A weird object came with her panties. I looked at her questioningly.

"The panties are called a gaff, and the object is called a tuck. They hold my dick in place, so I don't have a bulge, especially in a minidress like this."

I sat them on the adjacent sink and took his cock in my hand. It was sizeable, easily as big as mine, and he wasn't circumcised like I was. I pushed the foreskin back as I knelt before her stroking her cock. Precum streamed from her slit like water from a faucet.

Calista was gasping, her eyes closed and her head thrown back. I leaned forward and tentatively licked the liquid from his slit. I don't know what I was expecting, but it didn't taste bad. I kissed his cockhead and ran my tongue around it.

"Like that," I asked, looking up at her.

She nodded, her face gleaming with sweat in anticipation and her hips slowly pumping.

I took his balls in my hand, rolling them like the guy in the Caine Mutiny did with the steel balls. I took his cock in my mouth and gently sucked on the head. I looked up at Calista, who nodded at me.

"You're doing fine," she panted.

I swallowed her cock while simultaneously stoking her shaft and caressing her balls.

"Yes," she moaned, "yes!"

Her moans of pleasure encouraged me to continue. I began bobbing my head on her dick. The more I sucked, the more pleasurable it was. I was obsessed with the taste and the feel.

His gyrations sitting on the sink caused his cock to enter my throat, gagging me. I pulled back, coughing up saliva and precum."

"Taking a cock down your throat takes practice," Calista said, "We'll work on it, okay?'

I was like a junky. The more I sucked, the more I wanted to suck. Calista's precum filled my mouth; his cock swelled in my mouth.

"I'm going to cum!"

I redoubled my efforts. I wanted to taste him again, to feel him squirt in my mouth. She rested her hand on my head, her hips frantically thrusting.

Then I felt it, the first squirt as she began cumming. I swallowed instinctively, feeling her juice slide down my throat and into my belly. It was a fantastic feeling, an exquisite feeling. It was a feeling I had denied myself in my anxiety about what others thought.

Calista grasped my head, holding it as she frantically came in my mouth. "FUCK! FUCK!"

The flow slowed, as did her thrusting. I pulled back, taking her cock from my mouth but still stroking her shaft. A few drops bubbled out of the slit, and I licked them up.

"How did I do," I asked, looking up at her.

"Fantastic!"

She pulled me to my feet, and we kissed long and passionately.

"I love tasting my cum in your mouth," she whispered.

I grasped her slim behind, inched her skirt up and squeezed it while separating her ass cheeks. I pushed her panties to the side, applied light pressure to her anus, and gradually increased the pressure until my index finger's first joint slipped into her asshole.

"Oh my God, that feels good!"

I felt a small lump in her bowels and massaged it. This time I knew what it was and what it did.

"Do you like that?"

"Yes, you idiot," Calista giggled, "You're massaging my prostate. Keep that up, and I'm going to make a mess."

"Take off your skirt. I'm going to fuck you," I said, my voice hoarse with lust.

"Here," she said incredulously, "in the girls' bathroom?"

"Yes! I regret not doing it that day ten years ago at my home."

Calista balanced herself with one hand on my arm while she took off her skirt.

"I don't have any lube," she said, "but if you go slow, my anus will lubricate enough for you to fuck me."