Breaking all of the rules [MF] – [long, virginity]

Hey all, thanks so much for reading this story; this is my first time writing. This all happened a few years ago, and I’ve tweaked some of the details for anonymity.

Sex at the ***

——————

It started at the tournament. A nerd tournament that is – a debating tournament for high schoolers. I’d been involved in debating throughout University, and this year; nearing the end of my law degree, would be the last one I helped out at. Since I’d started Uni I’d been volunteering to help run these tournaments. Adjudicating the debate, booking the venues, and getting the awards sorted. And up till now I’d always been in a relationship. In my first year I’d been flirted with at the tournament by a senior student, but I’d done my best to diffuse the situation. But now, it was my final year, and I was single. I wasn’t seeking out to break the rules. But I wasn’t watching myself either.

Of course, it went against basically every rule in the book to become involved with the students. People had been kicked out in the past for such an offence, and I certainly wasn’t looking to tarnish my reputation. Plus, the half your age plus seven rule and all that.

A little about me: I’m 23, in my final year of a law degree; not in the American system. I’m 5’9, and around 70kg. I consider myself reasonably fit, and get to the gym quite regularly, although I haven’t quite got the six pack that I’m aiming for. I’ve been told that I’m attractive for a guy, and that I’ve got a nice smile. I certainly don’t have confidence issues.

I consider myself to be a man of integrity, but I also believe that everyone is corruptable. And for me, temptation came in the form of Alice. Alice was in her final year of high school, and had just turned 18. She was my height (5’9), but very slender. She had amazing long legs, a tight ass, and a slender body; except for what looked like surprisingly large breasts. She had long silky blond hair, and big glasses. She looked like the sort of person who would attend a debating tournament, but she definitely knew how to dress well too. This was her first year at the tournament, and on the second day, after her team narrowly lost in the semi-finals, we struck up a conversation at lunchtime. She was interested in my studies, and with why I helped out at these events. I explained that I hadn’t been much of a debater at school, but that I’d loved being part of a team, and helping up and coming debaters grow. I told her about my failed bid to become the President of my university’s debating society the year previously, but how I still enjoyed helping out these tournaments. We chatted about international affairs, and I mentioned that I listened to a few analytical podcasts from the BBC that gave some great insight into the issues the world was currently facing (pre-Brexit, and pre-Trump). She seemed interested. I asked about her school life, and she confided that she was ready to leave already, and couldn’t wait to leave home. She told how she was sneaking out to a party that evening, and how she was looking forward to doing more of that next year. When I finally checked the time, lunch was two minutes from over, so I bade my farewell, and hurried back to the room where I was adjudicating to help set up.

It struck me, as I listened to the debate that afternoon, that I’d engaged with Alice in a way that hadn’t happened to me before – at least not at these events. She’d seemed genuinely interested in what I was saying, and had some well developed views of the world. Not only was she incredibly physically attractive, but she was also intellectually attractive too. The event wrapped up, and the organising team headed into town for a few celebratory drinks. My phone buzzed halfway through. Facebook – one new friend request. It was from Alice.

I headed home from the drinks in a thoughtful mood. A friend request on Facebook meant nothing right? But then again, we’d gotten on so well! In the back of my mind though, I knew that accepting and chatting to her would violate just about every rule of this debating society. If I got caught, I’d be kicked out, and I would forever be a cautionary tale.

Then again, what was there to lose from just sending a message and seeing if a conversation happened?
“Hey, it was cool meeting you the other day! This was the podcast I was chatting to you about at the debating tournament. You should give it a listen!” Send. I was now back at home, two days after the event, and the nervous wait began. Would she reply? If so what would she say? Would she think I was being weird? I started to go over some study notes to distract myself, but barely 5 minutes later my laptop pinged. I had a new message – from Alice.
“Haha it sounds really interesting! I’m listening to one about an ex-drone pilot right now and it’s so engaging and thought-provoking. I can feel myself becoming more sophisticated already!”
My heart started to race a little. It was more than I’d hoped for. And I knew I really shouldn’t be doing this. But yet, here I was. “Anything to help you feel more sophisticated! Do you listen to podcasts much normally?”
She replied; “Not normally. Normally I’m more of a TV show binge-watcher or a reader”.
I then asked about her favourite books and TV shows, and the conversation progressed. The night wore on with us exchanging messages. I was beginning to think that my interest may have been reciprocated. Eventually it was time to head to bed for the night, but feeling bold, I thought I’d push the envelope.
“Hey, it’s been really cool chatting to you tonight! I don’t suppose you’d be interested in grabbing coffee or something sometime?”
I immediately regretted hitting send. That was far too forward. But a few moments later I got a reply.
“I don’t really drink coffee, but I’d love to meet up! There’s a really cool park up in the hills; we could go for a walk around there?”
Relief and excitement washing through me, I replied yes, and told her than I’d love to do that, and we made plans for the coming weekend.

I found it hard to concentrate for the rest of the week. I’d met up with girls before – attractive ones at that, but this was different. The fear of getting caught, the breaking of the rules, and the age gap were all playing on my mind, but were exciting me more than anything else. Eventually, the weekend arrived, and at 2pm Saturday afternoon, I was up at the park on the hill. I parked my car, walked towards the entrance, and saw Alice sitting at a bench. Outside, in the sunlight, and in casual clothes, she looked gorgeous. She was wearing a pair of denim shorts, and a casual, loose white t-shirt. I could see her long, slender, smooth legs in all their glory, and appreciate her small, yet perky ass. Her t-shirt was slightly translucent, and my suspicions about her breasts were confirmed.
They were definitely big, but not out of proportion. Her skin was light, but not unhealthily pale, and her smooth, straight blond hair seemed to glow in the light. I was struck by the thought I was seriously punching above my weight. I walked over, and she hugged me in greeting. Feeling her slender body up against mine was a big turn on

We started walking around the park, up towards the observation platform at the top of the hill, and chatting along the way. She’d listened to most of the podcasts in the series I’d sent her, and we had an engaging conversation about some of the topics covered. I discovered that she was currently studying to get a pilots license, and wanted to study medicine when she finished high school.

Eventually we reached the top of the hill. For such a gorgeous day, surprisingly, we were the only ones there. We walked over to the railing and stared over at the view. Neither of us said anything for a moment; we just stared. I glanced across at Alice, and admired the lines of her face for a moment. She glanced over at me, and I quickly glanced away, guiltily. I snuck another look in a moment later, and I caught her looking at me again. We locked eyes for a second, but didn’t move. A second passed, then I decided to make a move. I leant in, and our lips met. Her tongue shot forward into my mouth, and I felt her hands on my back. We continued the kiss, and I put one hand on her hips, and one on the side of her chest. We heard footsteps, and quickly broke apart as an older couple reached the platform. Blushing a little, she suggested that we walk back down. Once we were out of earshot of anyone else she asked me if I’d done that before.
“Not for a while. Have you?”
“I’ve kissed two guys before. But nothing more than that.”
I paused. I’d never found anything particularly attractive about virginity, or inexperience, but I had a deep hunger for Alice now. I decided to change the subject, and we continued down the trail, chatting about less difficult topics. As we neared the carpark, I asked how she’d gotten to the park in the first place.
“Oh, one of my friends dropped me off. My parents and younger sister are away from the weekend, and they took the car with them,” she replied.
There was a certain tension in the air with this reply. “Do you need a lift home at all?” I asked.
She paused. “I’m sure my friend can probably pick me up, don’t worry,” she said, and laughed nervously.
“Are you sure? It’s no hassle for me. And it’s just a lift!” I said, laughing nervously myself.
She considered it for a moment. Then said; “Sure, why not.”

It turned out that she only lived a 7 minute drive away from the park anyway, so it really was no hassle, and 7 minutes later, I was pulling up in the driveway of the empty house. I put on the handbrake, and Alice turned to look at me.
“Well, thanks for giving me the lift,” she said, smiling slightly awkwardly.
“Don’t mention it,” I said, smiling.
She took off her seatbelt, and opened the door of the car, but didn’t seem quite ready to climb out. There was a pause, as if she seemed to be figuring out whether to say something. I saw an opportunity, and took it.
“Hey, would you mind if I came in grabbed a glass of water before I head home?” I asked.
“Yeah, that would be fine,” she said, again smiling.
We climbed out of the car, and headed into the house. She unlocked, and opened the door, and I stepped in after. She stepped back to close the door behind me, and as she did, I placed a hand on her waist. She turned, and came at m quickly, locking me in a furious kiss. Here in the house though, with no one to catch us, it was hot and lusty. I wasn’t bothering to be respectful with my hands anymore. They were all over her back, her ass, and her breasts, and in turn, her hands were under my shirt. Still kissing, one of her hands drifted to the front of my pants, where there was now an unmistakeable bulge. She froze, and broke away.
“I’m sorry,” I said; almost automatically. “I don’t want you to feel uncomfortable.”
“It’s ok,” she said. “I’ve just never done this before.”
“We dont have to do anything if you don’t feel comfortable,” I said. She didn’t reply immediately, so I added “If you like, we can just mess around, and stick to what you feel comfortable with?”
She smiled, and nodded, and took my hand and led me down the hallway to a medium sized bedroom with light blue walls, and Harry Potter posters in adornment. I presumed it was hers.

***I took off my shoes, and sat on the bed, where she joined me. We started to make out again, though this time I was keeping my hands more G-rated. Soon though, her hands were under my shirt again. A few moments later, it was off, and her hands were all over my chest. I decided that this was fair game, so I slipped my hands under her shirt, and when there were no objections, I pulled it off.

Her body was a lot more trim and lean than I’d thought it would be, which just turned me on even more. Her breasts were amazing too, filling out her simple black bra easily. I ran my hands all over her torso, and then reached up and grabbed her breasts. She didn’t seem to mind, so I undid the bra quickly, and admired what fell out. Her breasts must easily have been a D cup at least, but they didn’t sag at all. The areolae were large, and light, and her nipples were puffy rather than erect. I kissed each one, and rolled her onto her back, so that I was on top now. We started kissing again, and slowly, yet deliberately, I ran a hand down her neck, down her chest, across her tummy, and onto the crotch of her denim shorts. She seemed to tense up slightly, but said nothing, so I began to move my finger in circles, until I could just feel her clit through the fabric. She started breathing heavily. Success. I kept fingering, and her fingers drifted down towards my waist, and began rubbing my cock through my pants. This sent me over the edge. I unbuttoned her pants, and pulled them down aggressively. A few shot moments later she was completely naked, and I gazed in wonder at her tight shaved pussy. I started fingering her clit again, and, still moaning, she undid my pants, and my 8 inch cock leapt out. She looked surprised at the size, but started stroking it anyway. She was seriously wet by now, so I tried to take things further.
“Should I grab a condom?”
She paused and blushed, and slowed her stroking down. “I’m not sure. I’m still a virgin”.
I was surprised, and I felt my heart sink a little. Nevertheless, I said, “That’s cool, how about we just stick to hands at the moment then, and I’ll go easy on you.”
She smiled, still nervously, and said “Ok, that sounds good.”
I kissed her on the lips, then kissed her neck, her breasts, and made my way down to her beautiful pussy. I started licking at her clit, flicking it up and down, and then side to side. She started moaning more heavily than before, and so I brought up a hand, and gently slid a finger inside. She started to moan more heavily, and her breathing got quicker and quicker. Her hands went down to my head, and she ran her fingers through my here, telling me not to stop. I picked up the pace, and her moaning got louder still. She suddenly jerked my head away from her pussy.
“Is something wrong?”
“I want you inside me.”
“Are you sure?”
“Definitely”
I practically leapt back at my pants, found my wallet, grabbed the condom I kept there, and tore it open. Alice leant back, and spread her legs, and started playing with her clit. I moved between her legs, positioned my cock at the opening of her wet slit, and slowly slid in. She was tight, but she was so wet that it wasn’t difficult to get the whole way in. Then, slowly, and gently, we started to fuck. I slid out slowly, and back in gently, and she began to moan again. I slowly began to pick up the pace, and established a steady rhythm. I leant forwards, and kissed her heavily on the lips.
“Faster,” she whispered, so I picked up the pace, and she began to moan more.
I began to fuck her harder, and deeper, and the moaning got more intense.
“Oh yes,” she moaned into my ear, “That feels so good! Don’t stop please!”
I kept going, but I could feel my cock starting to tingle. I was about to cum.
“Hold on a moment,” I said, and slowed down. I sat up so that I was kneeling between her legs now, and I began to finger her clit, as I gently slid in and out. I felt the tingling in my cock slowly go away.
“Can we try another position?” I asked.
She nodded, so I pulled out, and rolled her onto her front, but so that she was still lying down. I slid into her again, and began to fuck again. She started moaning again, and I wrapped my arms around her, and slid a hand to her clit, and began to finger her. The moaning intensified, and I moved another hand to her breast. I began to furiously kiss her neck, and she turned her head so we could kiss properly, as I fucked her harder, and deeper. I could feel the tingling in my cock begin again, but I didn’t care now as I could feel Alice tensing up too.
“Oh god, oh god, please don’t stop,” she gasped. I sped up my fingering, and my fucking again, and then felt her begin to tremble. She gasped again, and began to shudder and moan, as she came.
It was too much for me now. I let out a similar moan, and felt myself cum, and cum hard. I wished for a second that I wasn’t wearing a condom, so that I’d be able to see it drip out of her, but you can’t have everything can you?
I slid out gently, took off the condom, and threw it into the bin, and lay down next to her. I was panting for breath, and she was too. She shifted over to cuddle me, but looked up at me mischievously.
“What would happen if I told anyone about this?” she asked, grinning.
I laughed, and replied “I’d definitely get kicked out of the debating society.” I paused, then added, “If I was lucky.”
She laughed, and said “Well, you better keep me happy then.”
I laughed, and kissed her. “Whatever you need, you will get.”

Source: reddit.com/r/gonewildstories/comments/6skeq7/breaking_all_of_the_rules_mf_long_virginity