Where it happened: My Best Friend's Older Sister's Party and Wilson's Prom
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Haya. Here are two first time stories, the first time I shagged someone and the first ime I stole someones virginity. enjoy.
EMILY
Emily, the older woman. She was one of Stephan’s older sister’s friends and I mean older. She was 20 and to me a goddess. I had never met he till this particular evening and after it I never saw her again. Let’s just say it was a night of many firsts. At the time I was dating a girl named Shelly (who was also my best friend Brendan’s sister).
We where at a party Stephan’s sister was having in the September holidays of year 8. Stephan’s parents had gone home to Croatia for a bit and had left Soph in charge. The night was going well, Stephan and I getting relatively waisted along with all the 19 – 20 year olds. Later on Stephan disappeared somewhere (I later found out with a girl) leaving me alone to hang with the older crowd. I had a mega time being taught to mix shots and dancing with them. Eventually I got into a deep and meaningful with Emily which lead to us making out on the couch. People began to stop and notice. Emily said she was enjoying herself and suggested we grab another stubby and take it to one of the many bedrooms. At this point I was still too naive to anticipate what was to come.
We found a room, sat down and started talking again and about half way through my beer we began making out again. We fel onto the bed and I put my hand up her t – shirt, but instead of soft skin I’d hit lace. Fuck. A bra. I must have had a very surprised look on my face because she said, “You’ve never come up against one of these before have you?” I (naturally trying to stay cool) told her I came up against this sort of thing all the time, but I think she knew the whole time because after 10 minutes of fumbling around she told me to just look at her back as she showed me how to undo it with one hand. She then took of her bra and T to liberate the biggest pair of breasts I’d ever seen to date (OK… maybe I only think they where the biggest because I remember them through the eyes of a 14 year old. Either way they where surprisingly large). I then went around the front and started snogging her and feeling her up.
After a bit I ended up gathering the confidence to go further. Virtually lying on top of her, I undid her jeans and slipped my hand down the front of her panties, starting to finger her. Emily then started to move her hips back and forth. After a bit she must have thought I wasn’t a virgin because she asked me if I had a condom on me. When I said no she looked surprised saying that she thought all guys like me carried. But I think she got the idea pretty quickly, especially when she tossed me one and I asked her how to put it on so it doesn’t break ‘coz I didn’t know as I hadn’t used one before. Actually, she must have thought it was it was a bit funny because she laughed and called me cute. Emily told me to kneel on the end of the bed as she stood at the foot, undoing my jeans and sliding down my boxers to reveal my hard on. She then tore the condom rapper open with her teeth and pinched the end before sliding it over my entire length. She then ripped my shirt open, tearing it in the process, and pushed me backward onto the bed so I was lying on the flat of my back. She then stood up on the end of the bed and asked me if I was ready. She walked up the bed over the top of me, her legs split so that one was either side of me. She then squatted and eased me inside of her. I’ll never forget that exact moment. It was so painful for me, like slamming my hand in a door. I wonder if it was painful for her too. My face must have shown it or my body must have jerked because she leant over and kissed me and told me it’ll be alright and that she’d make it memorable for me. My heart was beating so fast my chest almost exploded; my veins surging with adrenaline.
She then grabbed me around my shoulders and started moving her hips up and down, still both of us making out. After a bit I naturally began to buck myself. A little after that I rolled us over so that I was on top. I started pushing up on her faster and faster. My lips had moved from her plump lips south to her supple breasts. At one point I even grabbed the bed head for support.
Emily began moaning. I stoped. She told me to keep going. Then I began to get this sensation all over my body. My flesh began to tingle, muscles contract uncontrollably. I started to cry out involuntarily in joy. Emily put her hand over my hand over my mouth to muffle me. I kept on pumping myself into her until I went completely numb. It was possibly the best orgasm I had had in my life to date; or maybe nothing ever compares to your first time. From the noises she was making it seemed she had a pretty good time too (or she was being really kind because she knew it was my first time.); but one thing’s for sure, she kept her promise… it was definitely memorable.
Afterward when we where just laying there Emily asked me what I thought. The only words I could muster where “good, very, very good”. I then asked her how she thought I was. She said to me that I could give some of the guys her age a run for their money. She then asked how I felt and we just laid there for a while whilst I talked and she just listened. It was nice. Before she left she kissed me and told me she’d see me around. I never found out if Stephan got as lucky as I did that night or not but something inside me hopes he did.
Emily taught me a lot of things that night (and I don’t just mean sexually), especially in regards to virgins. I’ve always tried to make every girl for who I’ve been their first feel as good and happy as I did that night; to listen to them, not expect anything of them, to be patient and ease into them because that’s going to be one of the most important moments of their life. To make it special for them because that moment is about them.
MELISSA
Melissa was the first person I slept with who wasn’t older than me. She was also he first virgin. We met in year nine and both took the surf lifesaving elective in the second semester; and we had Mr Muller, Mr Shake and Mrs Drum (the three dodgiest teachers in the school) taking us for it. God, the amount of times I saw her in a bikini when the boys and I where doing laps down at the pool and thought to myself ‘God I gotta have that piece of arse.’ My chance came up at the surf lifesaving camp at Wilson’s prom that year. Before we left for camp a group of us thought as seeing that half the class where boys and the other half girls, we’d pick one that we where interested in to work on so that there’d be no fights over the girls down at the prom. As you may have guessed by now I chose Melissa.
The first day was basically spent on the bus on the way to the prom. I sat in the seat next to Melissa and we started talking and getting to know each other. By the time we got to the prom we’d become relatively close. That afternoon a group of us took a walk down to Norman Bay and tried to show off our surfing talents (or in some cases our lack there of) to the girls, after which we went back to where we where camped to set up our tents; some of which ‘surprisingly’ backed on to others. Eventually Wednesday came around. This was the day we all went on our solo night treks. Brendan, Stephan, Podger and I teamed up with Soph, Tanya, Cassy and Melissa.
We decided to take the track from Tidal River to Oberon Bay via Little Oberon Bay. The walk there and back should’ve in theory taken us about 3 hours, but as you may’ve guessed it took us a little bit longer. Actually if Melissa hadn’t slipped the whole thing may have only taken two and a half hours. On the way to Oberon bay the boys and I stayed in a group at the front whilst the girls followed. When we got to the beach we decided to build a bonfire from the dead wood that had accumulated on the beach. We all sat on the beach around the fire and started talking. After a bit Brendan and Podger decided to take Soph and Cassy for a walk down the beach. Stephan and I stayed back with Tanya and Melissa. Eventually Tanya and Stephan stoped talking, laid down on the beach and started making out. Melissa and I took the hint and decided to go for an evening swim. Eventually one thing led to another and we ended up pashing in the surf whilst I fondled her backside. I went hard and she must have noticed because she then told me she’d never felt an erect penis before. Me being me, I naturally obliged to teach her; so I took the hand and placed it down the front of my boardies. Brendan and Podger came back with the two girls and they yelled out for us to come back in because we needed to start heading back to Norman Bay. Damn those two, they always seemed to have bad timing (well bad as far as I was concerned anyway). We went back in and I put my shirt and sandals back on before we began to head back.
On the way back Melissa and I lagged back behind the main group and Stephan and Tanya lagged even further back behind us. My hand was firmly clutching her arse the whole way between Oberon and Little Oberon Bay. Then, as we where climbing down some rocks to get down to the bay Melissa slipped and sliced her leg open. All I remember thinking at the time was “fuck I better fix this.” Brendan, Podger and the two girls saw us stop and sit down on the beach so they turned around and began to head back towards us. I yelled out for them to turn around and keep going back to camp. Podger yelled back, “Yeh, whatever,” and the group turned back around and stormed off. Melissa just lay down on the beach, a long cut down the length of her left shin.
I took out my medikit and started cleaning up her leg. Blood was oozing out everywhere. I cleaned and bandaged up her leg and asked if she wanted Stephan and I to run and get help when he got here. She told me that she’ll be fine but her leg was sore. I kissed her shin and asked her if it now felt better. Melissa told me it did but the top of her leg was killing her. I made my way up the inside of her sarong and kissed the top of her thigh. I made my way further north and popped her right breast out of her tight bikini top and began to suck on it. I began to go hard again and Melissa told me she didn’t get a good feel in the surf; so, I undid the fly on my three quarter’s and put her hand inside my fly. I started kissing her and she started stroking me. I asked Melissa if she knew how far I wanted to go and she told me she did. I then asked her if she’d gone that far before and she told me she hadn’t but she wanted to.
It was the perfect setting for her; the beach was empty, the sky was clear except for the moon and stars and the waves where crashing on the rocks. I took out my towel, picked her up and laid her down on it. I then split her sarong to one side and gently eased off her bikini briefs. I then undid the delicate string at the back of her top and carefully removed it. I began by kissing her small. I then moved to her delicate, and perfectly found breasts again; her right leg moving up unto an arch. I then moved up and kissed her sweet cherry flavoured lips. I then asked Melissa if she was ready and she said yes. I then went in and kissed her and, when she was least expecting it, I entered her. I’ll never forget the look on her face. The shock. The pain. The look in her eyes. How they where opened wide as; the pupils totally dilated, her mouth wide open gasping from the pain.
I started to slowly push up and down on her, her right leg curling in around my buttocks. She began to pulsate and cry (possibly from the pain). I will never ever in my life forget the tears running down Melissa’s face. We both then came at the same time, not long after which I saw Stephan and Tanya appear on the path (God knows what they where doing). I did up my pants and Melissa put her top back on before the other two caught up. When they did I made out I was just waiting for them to catch up so Stephan could help me carry Melissa back to where we were camped.
Later on that night when Melissa and I where sitting on the beach at Norman Bay I asked her how she felt about what had happened, just as Emily had done to me; and, just like Emily I sat and just listened as Melissa talked. She told me how she felt quite different to how she did before and a lot more liberated and less scared of the world after what we did earlier that evening together. Then, just as I had done with Emily, Melissa asked me what I thought of her; and, just like Emily did with me, I reassured her that she was very good.
Later on that evening just before I was about to go to bed Melissa asked me if I could walk her to the showers. Every evening for the rest of the two weeks we where at the prom I walked Melissa to the showers. In the end it came in handy that there was a general store within walking distance at Tidal River. Once we got back to school I never went near her and I’m sure no one ever found out what happened between the two of us. Melissa and I both kept it quiet and dean (the guy she hooked up with a few weeks later) thought that he was her first, just as Shelly thought that she was mine.
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