[MF] Losing My Virginity On a Post-Graduation Vacation

It was a sunny day in late November. I’d not long since graduated high school, and full of youthful energy, and a naivety and enthusiasm that only a lack of exposure to the real world can bring, I embarked on a week long holiday with four of my closest friends at the time to a sleepy little town in coastal Australia to celebrate our achievements by abusing substances, and attempting to sleep with complete strangers. I wasn’t much of a “party hard” kind of guy in high school. I’m still not, but I wasn’t then either. With a little bit of soul searching and pressure from my friends, two guys (Declan and Lewis), and two girls (Jess and Sasha), I realised this was a literal once in a lifetime opportunity, and I should seize it with both hands.

We were staying in a resort type place, renowned for being the place to be if you came to party, and almost exclusively occupied by recent graduates like ourselves. It was a pretty sweet place, real open plan with lots of apartments, and a central courtyard full of spas, hot tubs, a couple of massive pools, as well as a sauna, gym, and games room. I knew we were in for a good week. We spent the first night hovering around the courtyard, drinking, hanging out in the spas, playing pool, and getting to know some of the other people staying in the place. My friends fell in with one group of guys from a school near ours, though, as I was on the hunt for companionship of the female variety I excused myself to continue exploring and meeting people. I eventually found a group of 5 girls sitting and drinking in one of the larger spas, and, propelled by liquid courage, I ventured over, asked if I could join them, and slotted myself in between the most attractive two of the group.

I introduced myself, playing up my accent more than usual because, let’s be real, girls love that shit, and thanks to all the drinking, I was actually being somewhat funny, charming, and confident. I wasn’t socially hopeless, by any means, I was pretty popular and likeable, but just not so stellar at flirting, but that night it was second nature. I soon found out that the girl to my right had a boyfriend back at home, which meant all of my attention was focused on the girl to my left. Amy. I could lie, and say she was the most beautiful girl I’d ever had the privilege to lay eyes upon, but I won’t. That being said however, Amy was quite attractive, and French, her slight accent made everything she said sound so much sexier than intended, so I could only imagine how amazing it’d sound to hear her talk dirty. She sat next to me, wearing a fairly plain red bikini, which showed off her slim, petite frame and tanned skin, she had dark hair and eyes, and a cute smile to boot. When you’ve been stuck with the same handful of girls in your small town and high school, the unknown quantity of someone new is very enticing and alluring. We chatted for a while, about what I don’t remember, but it was hardly anything Earth shattering; in saying that though, it was hard to ignore the instantaneous chemistry, as well as the not so subtle, and in hindsight, awkward and hilarious flirting you’d expect from two inexperienced teenagers. It was nice though, and I spoke with Amy for what must have been hours. Eventually midnight rolled around and our first night was over, Amy and her friends called it a night and we parted ways as I went to find my friends, and then find my bed. I’d had a lot to drink and felt like I hadn’t stopped all day; I’m fairly sure I was asleep before my head touched the pillow that night.

The second day came around, my friends and I cooked breakfast, watched a movie or two, wandered around the shops in the town and visited the beaches, and found ourselves back at the apartments around the time the sun began to set and the place really began to come to life. All day I’d been trying my best to remember the girl from the night before, but being drunker than I’d ever been at that time, I could only remember she was gorgeous. No name, no apartment number, nothing. We made some dinner, and then my friends brought in this group of guys they were hanging out with the night before to party at our place. Eventually we made our way to their apartment where the rest of their group was; the door opened to a group of people sat around a dining table drinking and playing poker, a few guys, and one girl. My girl. The gorgeous girl from the first night. She was tall, slender, tanned skin and dark hair, with piercingly beautiful brown eyes, wearing some sort of dress made of a thin material over her bikini. Our eyes locked and she practically jumped up from the table shouting my name excitedly. Evidently I made quite the impression, as I tried desperately to remember hers. I later learnt her excitement was partly through seeing me again, and partly because one of the guys was trying to hit on her and she was not remotely interested, and wanted to get away from him. He hated me for that week.

My friends, and their new friends piled into the apartment, as the stunning girl whose name I remembered to be Amy rushed over to me. We chatted for a while, about what we’d been up to that day, and how much we hit it off that night. I commented on how much nicer the apartment we were in was than ours, at which point she mention that her group’s place was just down the hall, and offered to show me. I was naïve, but I wasn’t stupid, and accepted the offer excitedly. She took my hand and led me there, going in slowly as to not wake her friends who, for some reason, were already asleep. She showed me around quietly, and the tour ended in her room. We sat on her bed chatting more, and getting gradually more and more flirtatious with our touching and conversation. A light flicked on outside and Amy dragged me quickly into the room’s ensuite bathroom, explaining she didn’t want her friends to catch her with a guy. I never asked why. We sat on the bathroom floor, silent as could be, giggling to ourselves, our hearts racing from the thrill, the excitement, and the rising tension between the two of us. She looked at me, our faces were so close, and I just kissed her, and she kissed me back. It was the sloppy kissing of drunken and inexperienced teenagers, but it was incredible, and our hands began to explore one another before she pulled away and looked me in the eye.
“Not here. Your place.” She whispered.
I felt on the verge of bursting through my shorts, and my apartment was on the other side of the complex. I groaned, but knew what I had to do; I took Amy’s hand and led her stealthily out of her apartment and back to where my friends were. I went inside, navigating my way through the mass of dancing, sweaty bodies to find my friend Jess while Amy waited outside.
“Give me the fucking key.” I said urgently.
“What?” She asked confusedly.
“The key.” I replied, my patience wearing thin.
“Oh. Are you fucking serious!?” She responded incredulously, realising what was happening and why I needed our key.
“Yes. Key. Now.” I practically growled back. She handed me the key which I snatched from her hand, racing back out of the apartment. We practically sprinted back to where I was staying, unable to keep the thought of getting our hands all over one another and ripping one another’s clothes off out of our minds.

I fumbled the key into the lock, my hands shaking from excitement and nerves, eventually getting the door open and rushing into the apartment. We raced into the bedroom with the only double bed, slammed the door shut behind us, and closed the curtains. I looked at Amy, a mixture of emotions running through me, and I could tell she felt the same way. We came together, kissing, our hands all over one another, moving over to the bed gradually and lying down, her on her back and me over the top of her. The clothes began to come off; taking off her dress I was greeted with the tight, tanned body I saw on the first night, and eventually I worked off her bikni. Her tits were smaller than a handful, but perky and beautifully shaped, with the most amazing little brown nipples which were nice and hard. I gave them a suck and played with her breasts which she liked. She seemed pleasantly surprised when it came time for me to get undressed, grabbing my hard cock and giving it a few strokes. “It’s huge” she said in amazement. It was almost certainly a lie to stroke my ego, but I didn’t care, it made me feel incredible. This was the first time either of us had done anything like this, so our inexperience made for an awkward and not overly sexy encounter, but we made the most of it anyway. I inserted my middle finger into her wet pussy, with its sexy little bush of brown hair, and started to curl it back and forth slowly while my other hand rubbed her clit. She moaned, squealed, and practically screamed with excitement and pleasure. You could tell no one had done this for before. I’m sure it wasn’t all that good, but I tried my best. She was so tight, and shallow too. I couldn’t get more than a single finger in, and even that wouldn’t go the whole way in. I focused on her and her pussy for what must’ve been 20 or 30 minutes, doing my best to get it warmed up because I knew there was no way I’d be getting my cock in her like that.

She may have come in that time, I’m not entirely sure, but eventually when Amy was feeling thoroughly warmed up, and her wetness dripped down her thighs and her ass, I asked if she was ready. She nodded, hesitantly. There was so much anticipation and nervousness in that nod. I took out a condom, which she kindly slid onto my hard dick. I positioned myself between her legs, and slowly entered her. As the head of my cock pushed apart the lips of her pussy she tensed up and let out a gasp. I went as slow as I could go, and was as gentle and understanding as one could be as a drunken teenager losing their virginity, but it was no use. She was still too tight, still too shallow, and was in pain. We tried her bent over and from behind, we tried her on top, and we tried with a pillow under her hips, but had no luck. I was devastated, disappointed, and embarrassed, and so was she. I pulled her up to me, and we lay under the sheets feeling one another close, me playing with her amazing perky tits and ass, while we made out some more, our tongues intertwining, my lips on her neck, while she nibbled my ear. Being a trooper, she had me lay on my back and stroked me until I was hard again, and for the first time, sucked a cock. My cock. It wasn’t great, there was a lot of teeth and it was as clumsy as you’d expect, but I’d never gotten a blowjob before, so I enjoyed it, eventually telling her to just use her hands. I was struggling to finish, probably a result of the drinking and the nerves which hadn’t gone away. I told her I’d take care of it myself, and so she clambered onto the floor and waited patiently on her knees, it was unbelievably sexy to see her like that, her naked body waiting for me and my cock. I stood in front of her and began to stroke myself as Amy opened her mouth and asked me to cum all over her face and tits; for a girl with very little experience, this was a welcome surprise. I let out a moan, along with one of the biggest loads of my life which painted her pretty face and chest, at which point I just about collapsed onto the bed, a sweaty, exhausted, and very tired mess.

I suggested we shower, so she could clean herself up, and we could both feel a bit better, and so together we went into the ensuite with its small shower, crammed ourselves in there and cleaned up, along with a little bit more fondling and making out. We got out dried ourselves off, and lay back in bed, cuddling up close together still naked, while we talked about what happened, ourselves, and what would happen for the rest of the trip. It was strange for both of us, especially given that I don’t think Amy or I expected to be the kind of people to lose their virginity to a stranger on holiday, and for a young me, it was hard to not feel some sort of emotional connection. Eventually be both fell asleep, still with the light on, wrapped up in each other. I only found out the next morning I’d locked the apartment door, and left my friends out all night. Good times.

Source: reddit.com/r/gonewildstories/comments/5xl0nu/mf_losing_my_virginity_on_a_postgraduation