Fingering my high school crush after she told me to find out whether she shaves her pussy [MF]

***Everyone in this story is 18. Skip to the ——- if you’re not interested in the buildup (there’s a lot of buildup).

I was on the last man on the bench of my high school basketball team.

You may know the type: shortest guy on the team (5’10), wiry build, inordinate hustle, no skill, convinced that any day the coach would realize he’s had it wrong this whole season and would make me the focal point of the offense.

My crush happened to be my mirror image on the ladies team. Lynzi was 5’1, super athletic, small tits, and a great ass. Her other star feature was the cutest face I’ve seen to this day. We were good friends and had a flirty relationship, but nothing had ever happened between us.

She had been dating the same guy since 8th grade until they broke-up at the beginning of the semester. I don’t know how far they went, but I personally hadn’t even reached first base at the time.

One Friday night in early December, the girls and guys teams shared a bus home from an away game, a half hour’s drive from our school. Both teams’ coaches sat in the first 2 rows, then the girls team, and the boys team took up the back of the bus. Both teams must have won that night, because I remember a lively mood the whole drive.

I was sitting near the middle of the bus, alone and turned backward in my seat, shooting the shit with the guys behind me. Ten minutes into the ride, I felt a weight plop into the seat next to me, accompanied by an upbeat “Tom B!” (She always called me that, with my last initial–never simply Tom like the rest of the world.) I turned around and saw Lynzi beaming at me, her adorable face accentuated by prominent cheekbones and ever-present dimples. Her blonde hair was up in a ponytail, and she was wearing a black v-neck sweater with yellow sweatpants, our school color.

“Lynzi!” I replied, genuinely happy to see her so close.

“So, we had a question…” she said. I noticed that two other girls I was friendly with, Mindy and Violet, had followed Lynzi to my row, seated across the aisle and leaning toward us.

“Why yes,” I replied, “I *am* considered the coolest person on the guys team.” Goddamn, was I suave.

Lynzi punched my arm playfully and laughed. “Stop it! That’s not the question!”

“Ok, what’s the question?”

“So, we noticed all the guys shave their legs now.”

(Side note: This may have been a universal fad among adolescent males at the time, but I have a feeling it was just a weird quirk of culture at my high school: the guys had, in fact, started shaving their legs. I think it started with some of the meathead football players who heard that competitive bodybuilders shaved their legs to accentuate the appearance of muscles and decided to try it. Then the rest of us lemmings noticed and followed suit, even if we had no muscles to accentuate.)

“Yeah…?” I shrugged.

“Well, we were wondering if that’s, you know, all you guys shave.”

I blushed a thousand blushes.

My crush wanted to know about the condition of my genitals. Well, ok, she wanted to know about all the guys’ genitals, but mine were going to feature prominently in this conversation.

The next thought in my mind was indicative of my social standing: surely this was not a genuine question. Was my crush messing with me? Was the whole basketball team–BOTH basketball teams–messing with me?

I looked around. Everyone else on the bus was deep in their own conversations. Some raucous, some quiet, but all seemed real. No one knew this was going on except for the three ladies in my row.

“Umm,” I stammered, recollecting what I had seen among the guys in the locker room, and trying to decide how detailed and truthful I should be. “Well, some do. Some trim. But yeah, some go all the way.”

“What about you?” she asked.

“Uhhhhh…” Oh, man. What would the cool answer be? No idea. “I mean, I’ve done it, but not, like, always.”

“Hmm, ok! That’s all we wanted! Thanks, Tom B!”

“Wait,” I grabbed her arm as she started to scoot off the seat. “What about you?”

Now Lynzi blushed. She quickly glanced toward the other girls, then back to me. “We’re not going to tell you that.”

“But wait,” I protested, “I told you.”

“I know! But it’s a secret. Thanks, Tom B!”

And with that, the three girls giggled and moved back toward the front of the bus. I was left there, head spinning, trying to make heads or tails of what had just happened.

I was interrupted by a “Yo, TB!” from the back of the bus and got pulled back into whatever inane conversation was going on with the rest of my team.

The remainder of the drive passed in a blur. We got back to our school, and the team dropped our equipment in the locker room and flocked toward the parking lot. The girls team came out of their locker room at the same time, and the two groups merged, chatting as we walked. I nodded in Lynzi’s direction and we approached one another. I had no idea how to deal with our conversation from the bus, but fortunately, she spoke first.

“Need a ride?”

We lived on the same side of town, and she knew I didn’t have a car.

“Sure!”

Lynzi and I veered in the direction of her car, cast in the orange glow of the parking lot lights.

She spoke first again. “Sorry if we made you uncomfortable back there. I know it was a weird question, and you were cool for going along with it, but I wasn’t prepared for it to come back in my direction. Especially with Mindy and Violet there. You know the girls aren’t as, um, free in the locker room as the guys are.”

“It’s cool,” I said, “I mean, you caught me very off guard. But it’s cool.”

We had reached her car. I threw my gym bag in the back seat, then lowered myself into the passenger seat. Lynzi started the car and pulled out of the parking lot, the radio blasting Top 40.

Lynzi came to a stop at the first traffic light. I turned toward her.

“You gave a bullshit answer though,” I said.

Her face turned red, and she broke into a playful smile. Those dimples. “I’m not going to tell you,” she smirked as she turned toward me, “but maybe you’ll find out.”

The light turned green and she accelerated as I grasped for a response.

“H-How will I find out?”

“I don’t know,” she smirked again.

The radio played on.

Lynzi slowed the car as we approached another red light, less than a mile from our neighborhood.

“Do you want to come over for a bit?”

I looked at the clock on her car radio. 10:44. My curfew was midnight.

“Yeah, sure,” I said, trying to play it cool, though I was sure she could hear my heart beating through my shirt. Hell, I was sure the people in the car next to us could hear it.

We got to her house, got out of the car, and walked toward the front door. I could see lights on in the windows upstairs, but just a faint glow coming through the frosted glass of the door before she opened it.

“My parents are upstairs, but they won’t come down,” she whispered as we kicked off our shoes and she flicked on some lights.

She walked toward the living room in the rear of the house, and I followed.

“Let’s sit on the couch,” she said. She eased herself into one end of the couch, facing toward the middle. Her left leg was curled in front of herself on the couch, her right dangling down with the foot on the floor.

I sat in the middle of the couch, mirroring her position, close enough to touch her, but not doing so.

————————–

She broke the silence. “Well, are you going to find out?”

I looked at her leg in front of me. A couple inches of pale skin peaked back at me between her ankle sock and her sweatpants.

I reached out with my right hand, softly touching the exposed skin and moving my hand up to her lower skin beneath the baggy sweatpants.

I looked up at Lynzi’s face for approval. She looked back with an expression full of anticipation.

“It’s so smooth,” I said, “you’re clearly a more experienced shaver than me.”

She laughed, and I inched my hand up the outside of her shin, beginning to rub softly up and down as I progressed.

“That feels good,” she purred.

I treasured every sinew of muscle, every ridge of bone I passed as I made my way to her knee.

When I reached her knee, Lynzi laid back into a pillow and straightened her leg to improve my access. I slid to my knees on the floor. I was now situated between her legs, half my right forearm lost beneath her sweatpants. I reached my left arm around her opposing leg and brought my hand to rest on top of her thigh.

I continued snaking my right arm up her pant leg along the top of her thigh, caressing the outer thigh with my fingers. She gave an ever-so-slight but ever-so-meaningful wiggle of approval.

I pivoted my hand at the wrist to turn my fingers to her inner thigh, and she wiggled again. My eyes had been fixed on her leg, and I now glanced up at her face. Her eyes were locked on her leg as well, until she met my gaze and spoke: “you can keep going.”

My heart raced, and I silently gulped. I timidly caressed as I inched up her inner thigh. I was now mere inches from the promised land. I could feel the heat building inside her sweatpants.

“Keep going,” she rasped.

I inched up again, and extended my fingertips to gently touch her crotch through her damp panties.

I withdrew my hand back toward her leg, then reached under her panties as I slid my fingers and palm through the leg hole and across her mound while my thumb rested on her labia. There was no hair to be found.

“So smooth,” I marvelled.

“Now you know,” she said, her cute nose scrunching up as she broke into a smile ripe with passion.

I shifted the angle of my hand to explore her pussy with my fingers, and for the first time felt that wonderful wetness between her folds. So warm. So slick.

Lynzi reached her right hand into the sweatpants and pulled her panties to the side.

I ran my middle finger gently around the full length and breadth of her vulva, sensing every contour and feature before fingering her entrance.

I looked up at her face again. She had closed her eyes and was leaning back into the pillow.

Delicately, slowly, preciously, I inserted the tip of my finger into her. She inhaled and licked her lips, eyes still closed. From the position I was in, my arm now all the way up to the shoulder in her sweatpants, I wasn’t able to get deeper than my first knuckle. I stroked the walls of her vagina for a few seconds before withdrawing my finger in search of more pleasure for her.

I drew my finger upward along her pussy and discovered what must be the clit, at once stiff and pliable beneath my fingertip. I massaged it in a few tight circles as it emerged from beneath its hood.

I moved my finger back down to her opening once more to reload on her juices, then ran it back up to her clit.

As I massaged it in soft circles, her hips began gently rocking, and I watched that adorable face undergo waves of pleasure, her breathing getting stronger, tongue and lips working against each other as she emitted soft moans.

After just a minute or so of this pattern, she suddenly reached down with her left hand and grabbed my arm through her pants. She held her breath as her whole body tensed.

With a breathy “oh my GOD,” she came hard, her body now releasing into complete relaxation, her chest heaving, and she melted into the couch.

With her right hand she re-positioned her panties back into place, nudging my hand aside. I withdrew it back to her thigh as she opened her eyes and looked down at me.

“Oh my god,” she repeated. “Fuck. That was intense.”

“That was incredible,” I replied.

“You’re incredible.”

I noticed the clock behind the couch. Fuck. I had to get home.

Ignoring my throbbing dick, I said “It’s almost twelve. Can you give me a ride home?”

“Of course.”

We unwound ourselves from one another and stood up. I saw her notice the bulge in my pants, but she said nothing. We silently walked to the front door, put on our shoes, and headed out to her car.

It was only a 90-second ride to my house. I still remember Train’s “Drops of Jupiter” playing as we drove.

She pulled into my driveway and shifted into park. We looked at each other and I said, “Lynzi, that was amazing.”

She reached over, squeezed my hand, and said, “Yeah it was. But I need to find out a little more about you next time, Tom B.”

I got out of the car, grabbed my gym bag from the backseat, and walked to the front door. I heard her reversing out of the driveway behind me.

Once inside, I dropped my bag and sighed. I almost couldn’t believe what had just happened. I raised my hand to my nose and took a sniff. Her sweet juices permeated my nostrils, and I said to myself, “Oh yeah, it happened.”

Source: reddit.com/r/gonewildstories/comments/tglqaz/fingering_my_high_school_crush_after_she_told_me

63 comments

  1. I love the wholesome and innocent days where every new step in exploration was the most intense experience ever

  2. Drops of Jupiter is ingrained in my memory too!! Not for the first time I slid my finger into a girl’s promised land but for another time. Great story!

  3. That was a great narration, i hope she returned favour . Would love to hear more from you

  4. Great story – really well written and, besides being sexy, also romantic. I’d upvote more than once if it was possible.

  5. Ngl I lost it when you included the detail y’all were listening to Drops of Jupiter lmao

  6. If this is true, what happened with you guys? Did you ever get together? What happened?

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