Back in my high school days, I had a huge crush on Tyler Peters. He was super popular and dated the hottest girls, especially if they had a reputation for being "fast" - everybody knew who they were.

I was a plain Jane wallflower, though far from ugly. A plain Becky, if you want to use my own name.

Tyler was in most of my AP classes and was super smart. He was always nice to me, but that didn't include asking me out. It didn't help that I had a fixation on virginity. Word got around.

Not that my sex life was exactly zero. I discovered masturbation on my own. And on dates, things did move along to a point. But alone, more and more, I imagined Tyler's hands brushing across my chest over my nightie. I would pull up the bed covers to hide my bare tits after I eased the straps over my shoulders. My palms stood in for his as I brushed my nipples ‘til they stood up.

Then I would simulate Tyler pushing my nightie between my legs and rubbing until the cloth got wet. My knees would go wide, drawing the hem of my nightie up to my thighs. I imagined him seeing I had no panties and putting his hand on my bare pussy. My own fingers played in the folds. Somehow, he would already be naked as he drew close with his cock. My fingers went in as his imagined cock did likewise, and with my thumb, brought on a rocking orgasm.

Alex was the first boy to touch my boobs, through my top and then under it. It felt so good. We were in the front seat of his father's car. I guess I was 17 by then. I didn't let his hands wander elsewhere for months.

But eventually, my solo nights with Tyler pushed me forward. I didn't stop Alex when he tried to rub my shorts between my legs. On our next date, I wore a skirt. I knew what I wanted. He found my wet panties and pushed them into my crack.

"You can see my pussy if I can see your dick," I said. "I've never seen one." I slid my panties off as he opened his shorts and pulled out his cock. I grabbed it and held his hand between my legs.

We started masturbating each other. "There," I said, directing him to my clit, though I didn't know its name yet. He really liked it. "Put your finger in," I begged breathlessly.

My hips were rocking, and his cock pulsed in my hand by the time he warned, "It's gonna squirt," which it did a half second later. It landed on the console between our seats, on my uplifted skirt, on my leg and even on my pussy. I only learned later how risky that place was.

Alone that night in bed, it was Tyler's cock that I pretended to stroke—I stroked my leg—and Tyler's fingers in my vagina.

Alex and I enjoyed playing together for several weeks, usually in my basement rec room. On the other hand, I wouldn't let him climb over me to mount me. I wanted to stay a virgin.

In the end, I paid a price for my reluctance. Alex stopped asking me out and coming by after school. I found out he was hooking up with Abigail, a known slut.

I set the same limits with Nick, the next boy I started dating. He seemed to appreciate what we were doing, if we could masturbate each other to completion. Somewhere along the way, I learned about oral sex. He was delighted when I took his cock in my mouth and bobbed up and down on it 'til he came. He didn't want to lick my pussy, so I did what other girls told me to try. The next time, I refused to suck his dick until he ate my cunt. Of course, that was amazing. Alone in bed that night, fantasy Tyler licked between my folds.

And so, a couple of days before the prom, I told Nick to buy some condoms. My friend Sarah's parents had let her use their house for an after-prom party. Nick and I found a bedroom. Everyone heard him exclaim, "Becky, Becky, Becky."

We left a bloodstain on the sheet.

All summer long, we romped every chance we could, 'til we went to separate colleges. My obsession with Tyler, whom I no longer saw every day in class, dissolved, though I did take his ghost to bed with me after Nick on prom night. What if it had been him?

I could write about the wild sex life I had in college. Parties, boyfriends, groups, a couple times with other girls. But this story is about my crush on Tyler. So I'll move on to my married life.

When gonorrhea ripped through my college crowd, I also needed a shot. I became choosier. I was a different girl by the time I met Brandon, my future husband, in grad school. Still, we had a great time in bed and used almost every form of heterosexual pleasure available to two faithful people. That continued to our marriage bed, - not just bed, LOL.

I had forgotten about Tyler for years. Then I heard we had a new hire. I gasped when I saw who it was. Tyler! And they parked him into the cubicle next to mine. This was before the pandemic and everybody still went to work every day. We exchanged the usual "So good to see you again" greetings and got down to work. But he needed a lot of help with our systems and just chit chat about who's who.

And there it was. The old crush out-of-reach Tyler flamed up inside me. It was bad. "What's wrong with you, girl? You're not in high school anymore," I told myself. I would stare at him when he was looking the other way. I learned he was still single. Not so unapproachable, but now it was me, happily married and wanting to keep it that way.

I managed to stay under control for the rest of the day. But when I got home that evening, I knew what I needed before Brandon got home. I mixed a Manhattan and sat with it at the kitchen table. I opened my top and pulled my bra down. My imagined Tyler squeezing my nipples 'til they almost hurt. My Manhattan never tasted better. His hand pulled my skirt up under the table and pushed the damp crotch of my panties between my pussy lips.

"Oh yes, Tyler. Oh yes," I exclaimed to the empty house and took another sip. The strong liquor burned in my throat. Tyler crawled under the table and between my legs.

My hand wrapped my mound as if it was Tyler's mouth taking it into his mouth and gnawing. It was hard not to spill the drink as my body shook and I tried to sip it.

Tyler pulled off my panties. He sucked on my lips. The cherry sat alone in the bottom of the glass. My fingers were Tyler's tongue as he licked my clit. I dumped the cherry into my mouth and ate it as my belly convulsed.

"Fuck me, Tyler. Fuck me," I screamed.

My fingers, Tyler's dick, plunged deep into my vagina and started stroking. A burst of my juices squirted onto my hand, my skirt, and the floor. The fucking went on 'til I was spent. Long time since that happened.

Brandon was due home in fifteen minutes, so I rushed to get my clothes into the hamper and clean up the mess in the dining room. I used a washcloth to clean myself and changed into a plain blue house dress with nothing under.

When he opened the front door, I was in the dining room dribbling vermouth into a mixing glass of martinis that already included his favorite Ketel One vodka. I shook it while he came over a kissed me. I strained the mix into two martini glasses I took out of the freezer and added a lemon twist to each. The rest went into a glass pitcher that I put back into the fridge.

We wandered over to the living room, where we toasted each other formally. I nudged him gently onto the sofa. Brandon and my sex life included several scenarios that kept things interesting. He waited to see what I had in mind. I stood back out of reach and erotically ran my tongue around the rim of my glass, letting the twist fall into the martini. I took a long sip and set the glass on one a side table next to our easy chair. Then I massaged my dress over my tits and slowly moved one hand down the fabric. My body jerked slightly as I pushed the cloth between my legs and rubbed. Brandon had already figured out where this was headed and adjusted the emerging bulge in his pants. Our breathing got heavier as we played with our hidden prizes.

We stopped and took another sip of our drinks. Then I slipped the straps off my dress and brought my boobs out. Brandon removed his belt and unclipped is trousers. I twiddled my nipples until his cock came out. The dress fell to the floor leaving me naked as I stood across from him. He pulled his balls out and rolled them in his hand for me to see. I covered my mound with my hand and pushed it back and forth.

This was supposed to get my mind away from the fantasy I had just had, but instead I couldn't help but wonder how Tyler's dick compared with Brandon's. I pushed my finger through the folds covering my clit as Brandon held his shaft aloft. Knees weakening, I dropped into the easy chair with my legs apart. Brandon slipped his pants and jockeys off and got out of his shirts. I held my labia apart exposing my shiny wet pink insides to him. He started stroking.

I pulled out a dildo I had secreted beside the seat cushions and turned it on. I couldn't help but imagine Tyler licking my clit as I fired up with the toy. As I ran it down my slit toward my opening, I imagined Tyler standing in front of me his cock ready. I briefly took the vibrating toy into my mouth, wondering how his cock tasted. Then I held it between my legs and plunged it in.

Brandon's body thrust up, up, up as he pretended to fuck me.

Tyler's cock brought me to full orgasm.

"Ty...," I started to exclaim, then recovered, "Time now! Now. Now."

Brandon wasn't even trying to hold back. His jism shot onto his chest and onto the coffee table and his legs. My vagina flooded the seat with my love juice. We both collapsed for a few seconds before emptying our cocktails into our throats.

I got up, took both our glasses, and refilled them. I sat next to Brandon on the sofa and wiped off his body with a table napkin I had taken. I could only take a couple sips, but by the time his second drink was empty, we put our hands on each other’s genitals and began playing. His fingers and thumb brought back my rising climax; his body pushed his cock up into my grip. We were ready to make love the normal way.

Brandon had to help me stagger into the bedroom.