[MF] Lost My Virginity on the Rail Trail

*names have been changed to protect the guilty. This is my first time writing anything really erotic, so let me know if I should keep doing it!

The year was 2012, eight years ago to the day. Her name was Katie, and mine is Mark. This was the summer before we all went off to college, We were both 18, both young and horny and dumb, and had a little too much free time.

I had worked at the local boxing gym a couple days a week, teaching little kids classes, really more of a babysitting job than anything that will help them one day in a fight. Usually, the parents would sit on benches off to the side of the room, to watch their kids and maybe intervene if someone was a little punchy. It was there when I saw her for the first time.

Katie – not really tall but not really short, 5’7″, blonde, not her real hair color but not badly done, and blessed with what I would later learn were 34Ds, enormous on her tight body. She was wearing a tight, navy, short sleeve shirt with a few buttons undone. It only did her favors, and try as I might, I kept finding my eyes drifting in her direction throughout the class.

Maybe on the fourth or fifth once over did my eyes move upward. I found two lovely blue eyes starting back at me. “Uh oh” I thought, ready to slide into a hole in the ground. It was only when I saw her continue to meet my gaze and smile at me did I suspect I could actually talk to a hot girl, something which, even at 18, was pretty new to me.

It wasn’t that I was unattractive, I have an appeal, to be frank. I had no concerns about my below the belt situation (feel welcome to check out my other posts), but I found that I was a bit tongue tied around hot girls in that era of my life.

At the end of the class, I worked up what I believed then was a titanic amount of courage, took initiative and walked over to introduce myself.

Her first words to me: “I’m Katie, and I liked that you were looking at me.”

At this point, my brain completely shorted out. I learned that she was the older cousin of a kid in the class, here from Nevada and staying with her aunt and uncle over the summer. I just kept smiling and nodding not saying very much other than “your cousin is pretty good at this” and praying that she didn’t notice my growing bulge in my sweatpants (why I didn’t want her to notice this still confuses me now).

We continued to flirt, or rather she continued to flirt and I tried to keep my head above water, and then I had to start the next class, so I wished her goodbye and she said, “I’d like to see you again soon.”

That night, I logged into 2012 era Facebook and saw a friend request. Katie. Yes. If I didn’t have to actually speak, I could do this.

“Hi Katie, I can’t believe you friended me! I wanted to do that to you.”

“Mark, of course. It was great to meet you today. When are you teaching next?”

“Not until Monday, but let’s get lunch before?”

“I’m down, but to be honest I’m not sure if we should date. I’m leaving at the end of the summer and don’t want anything long term.”

This was a setback, but in a moment of inspiration and desperation and horniness, I wrote.

“This is just a moment in our lives. Let’s go on a date and enjoy each other for as long as we can and as long as we’re willing.” I still cringe thinking about it today.

“Wow. What’s your number?”

This kind of chatter continued, on Facebook messages and texting on our own flip phones over the next few days. In my 18 year old glory, I thought I was falling in love. In reality, we just both needed to get laid. Things escalated in the night before our date.

I pulled out my old flip phone, on its last legs even in 2012, and I read:

“Can I send you a picture of me topless?”

“Um yes.”

I was surprised with what I received. Even in my 1.5 inch square screen, those two beautiful tits, nipples just a little larger than I expected, about half dollar size, looking back at me.

“Fuck”, the only thought that came to mind.

“What’s your favorite color, Mark?”

“Purple.”

“Great, I’ll see you for lunch tomorrow.”

~~~

Driving downtown for our date, I took a detour to the condom section of CVS. Trying not to turn red, I handed over a three-pack of magnums and a ten dollar bill, and walked away. I had never bought condoms before and was so nervous, in fact, that I forgot to get the change and had to walk back in, face now purple, to collect the money.

The date itself went really nicely. I was comfortable with Katie at this point, so we talked about all kinds of things. Her life in Nevada was difficult on her. She chafed against her parents, as she didn’t share their faith and their outlook on life. Looking straight at me over her sandwich, she said, “yeah, you should have seen how mad they were when they found me with this guy I used to date in the back of my car.”

We took a walk after lunch, on a historic path that weaves around the downtown that used to be the train line, the “Rail Trail.”

We came to a part of the trail, thickly forested, and she looked at me again. I noticed her shirt (this time, a red, loose tank), had pulled a little lower, exposing the tops of those two beautiful breasts. “Hey,” she said. “We can’t go to my aunt and uncles house, and I’m sure we can’t go to your parents house. Is there somewhere we can be alone?”

She stepped forward, closer to me.

“Um” I said.

She stepped closer, now just an inch away.

“I guess we’re alone here” and our lips touched. We kissed, passionately, for what felt like hours but was probably only a few minutes. I had only kissed a little, and this was not like anything I had experienced before. She took charge, sucking my tongue into her mouth, kissing me in ways I couldn’t dream because I had not yet conceived them.

She broke off, “let’s go into the woods.” We walked, practically ran, through the trees until we found a clearing. Getting on her knees, she ripped off her red tank top and red bra, showing me, in person, her amazing tits.

“Help me with your pants,” she said. As I slid off my pants and my boxer briefs in one motion, I saw her eyes widen.

“Are you fucking kidding me?” she asked, impressed.

“Wha-AH,” I started, having to stop when I felt her immediately take half of my cock in her mouth. I was astonished. I had no experience in blowjobs, but I immediately knew that she knew what she was doing. Taking me nearly three quarters of the way down, massaging my immediately tightening balls, taking her tongue under the remnant of my frenulum, I could barely stand from the pleasure.

“Open your eyes, Mark, you’re missing the show,” said Katie, detaching herself from my cock.

“Oh shit.” Somehow, as she was blowing me, Katie had gotten her pants off, wearing only a tiny, purple thong.

“How did you do that?” I asked.

“I have two hands, stud.” She returned to blowing me.

This time, not wanting to miss a moment, I kept my eyes open, and found her eyes looking back as she took my dick nearly all the way down, her beautiful nipples brushing the sides of my thighs as she bobbed in and out.

“This is unfair,” I said, “I don’t want to bust yet. Get down.”

“On what?” she asked.

I laid out my clothes on the ground. “Lay on this? I should have brought a blanket.”

She laid down and opened her legs for me. I gingerly getting down on top of her, began kissing her neck, lower, lower, to swirling her nipples with my tongue. She moaned out, so I assumed she liked that, and I kept doing it for a few minutes, pinching, licking, sucking those beautiful globes. She grabbed my hand and pulled it down to the purple thong.

Taking the hint, I moved my hands under the thin material, touching heaven for the first time. Hot and wet, I immediately found my way in, and got acquainted with my first pussy.

“What should I do?” I asked.

“Curl your finger upward,” she purred. She really liked that. Breathing harder and harder. I kept my mouth on her tits and my finger inside her. Taking my thumb, I rubbed on what I hoped was her clit. She immediately tensed up and shook, finding her orgasm. “FUCK,” she screamed.

I immediately clammed up “Katie, you can’t yell, someone might hear!”

She pulled my head up to hers and buried herself in my chest, her voice raspy. “I don’t fucking care. Get inside me.”

She lifted up her ass, starting to pull her thong down.

In a moment of now what is clear was incredible stupidity, I said. “I brought condoms but I don’t need to use them if you don’t want.”

“No, just put it in me. If you want you can put one on right before you cum. My parents made me go on birth control and you can be careful if you want. I think you should know what it really feels like your first time.”

18 and feeling supremely irresponsible, that was all I needed. With her help, I lined myself up at her tight, shaved pussy.

“Ready to lose your virginity,” said Katie, nearly giggling.

“uh, yes please.”

I slowly slid into her, “be careful Mark,” she said “you’re so big.”

I was overwhelmed. As many of us know and I was coming to learn, there’s nothing quite like that first thrust. Pushing, sliding your way inside, moaning, nails digging in, the head of my penis challenging and stretching the walls of her impossibly tight pussy. When it’s right, there’s nothing better, and it was right.

Eventually, I was able to push all the way in. Gentle moving back and forth, getting used to the motions that come with this critical part of life. We continued like this for a while. Gently fucking, me because I didn’t want to bust quickly, her so she could get used to me.

“Mark. Yes, yes, yes,” she said. “Harder,” she asked, so I went harder, my face getting red from the physical exertion.

I continue to thrust, like a machine, our bodies growing more and more sweaty in the summer air, the smacking of our skin growing louder and louder as we fucked harder and harder. This is what I was missing out on, and it was fucking incredible.

“Let me ride you” she said.

Now it was my turn to get down on the forest floor, my back on the clothes that I wore there, covered in her sweat and her other wetness.

She sank down on me, taking me more easily now. Leaning back as she did.

“Oh!” I said, surprised and uncomfortable. “Come forward.”

She leaned in, tits handling low, nipples nearly touching my chest. As she rode me like this, I began to lose control. Her blonde hair formed a curtain around my head as she bounced up and down on my cock. I could only see her eyes in the soft blonde glow of the sun through her hair. I reached out to touch her clit, and she moaned and fucked me faster. I didn’t stand a chance.

“Katie, I have to cum,” I announced. “Slow down so I can let you finish again.”

“No, I need you to cum,” she moaned. “Don’t pull out if you don’t want to.”

And so, in another act of ecstatic stupidity, I thrust harder and faster until my balls tightened fully and I swelled.

“FUCK YES!” I yelled as my cock exploded inside her, releasing what I thought had to be a gallon of cum.

“Mmmmmmmmmmmm” she moaned, lowering herself down on my deflating cock, trying to catch the last vestige of my hard erection.

Breathing heavy, still thrusting just a little due to habit, my brain functioning slowly returned.

“Wow,” was all I could say.

“Very nice Mark, you lasted a while.” She came down low and kissed me on the cheek. “Maybe I’ll have to come back next summer.”

~~~

As it turned out, Katie didn’t come back next summer, nor has she in the eight years since we fucked on that summer afternoon. She started seeing some lucky guy in Nevada and then broke up with him. I started seeing someone and broke up with her. We both started college and got lives.

Sometimes we reconnect, an occasional birthday text or the old Facebook DMs. Maybe one day soon she’ll come back and we’ll go get railed on the Rail Trail again. Maybe it won’t happen.

Regardless, it will always be a lovely memory.

Source: reddit.com/r/gonewildstories/comments/ht1kt3/mf_lost_my_virginity_on_the_rail_trail