Losing My Virginity At The Beach
When I was 14 I convinced my parents to let me and a few of my best friends go to the beach as long as my sister chaperoned. My sister got a free beach trip out of it, so she was happy about it, but in hindsight leaving a 19 year old in charge of a bunch of 14 and 15 year olds was probably not the best idea.
Well, things happened pretty quick. Our first night there she ditched us at the restaurant where we had dinner and I caught her flirting with some older boy, and saw them kissing. This wouldn't be a problem except that my sister had a boyfriend back home. Well, I didn't care that she was cheating, but I was jealous that she had someone to kiss. See I had just recently discovered sex, sort of - my best guy friend and I made out one night and that turned into him putting his hands on my boobs and me putting my hand on his dick, but just over clothes. We wanted to know what kissing was like but didn't really know what we were doing. I tried giving him head but I did a pretty bad job and he couldn't cum. I didn't know better at the time though. But I loved the way he touched me, it made me feel good and feel sexy. More happened with him later but that's not the point of the story.
So when I saw my sister kissing this boy, and he grabbed her ass, I got very turned on. I wanted a boy to do that to me. I didn't tell her I was watching but that night when we all went to the beach house, I went straight to the bathroom and masturbated furiously and orgasmed hard thinking about meeting a guy at the beach and us touching each other.
One other aspect of this trip is that my friends and I all had to share rooms, but my sister, being the chaperone and the older one, declares she got a room to herself. So my friend Danielle and I slept in a bed together, and the other three girls were in a bunk room together. This made it really difficult to have "me time" as I called it back then, so I had to go to the bathroom to cum when I was horny. Which was often.
So that first night, after everyone has gone to bed, I sneak off to the bathroom to have some me time, and I see my sister and that same guy sitting on the couch making out!!! That total slut. I didn't know what to do, I froze, and thankfully was in the shadows in the hallway or they would have seen me. And I watched for what felt like forever. I watched her head disappear below the back of the couch and could kinda see her bobbing up and down. He groaned and she sat up and shushed him.. And I couldn't believe what I saw next.
My sister climbed on top of him, sat in his lap facing him, and lowered herself down.. Let out a gasp.. And started slowly moving up and down. I knew he was inside her. They were fucking. I'd never been fucked, but I wanted it bad. I reached down between my legs and was soaked. I wanted to finger myself but I was so scared of getting caught, and I knew if I went to the bathroom they would hear me and freak out, so I just watched. She rode him for a long time and eventually got off and gave him a blowjob again. I guess he came because after they stood up and kissed and he said "see you tomorrow" and left. I snuck back to my room, waited til I heard my sister's door close, and bolted to the bathroom for the best me time I'd ever had.
Okay so, I obviously could not get it out of my mind. Being at the beach didn't matter anymore. I wanted to be in a guy's lap like that. I wanted a guy's hands on me like his were. But I was so scared to bring a guy over or even try to talk to a guy and my sister tell our mom. I didn't think I could make it work. I thought - what could I do that would make her keep her mouth shut?
This is probably really bad. I'm not proud of it. But the next morning I got her alone in the kitchen and said "I saw you two last night." She froze and looked as pale as a ghost and all she could say was "what? When?" so I said "when you were in his lap. When he was fucking you."
She said "what can I do to keep your mouth shut?" and I knew I had done it. I didn't really know what I was supposed to do next, because, how was I gonna even find a boy? But I said "I want what you got. I want to get fucked." she said "no way, you're way too young for that" so I said "well you're way too in a relationship for that" and she groaned before saying "fine."
I thought it was gonna work, but still had no idea how to find a guy. She was texting in her phone and it didn't click what was happening until she said "he said he'll fuck you tonight." She looked so unexcited and walked out of the kitchen and to her room.
I'll admit I was really nervous, the most I'd ever done was suck a dick and have a couple of fingers in me. I didn't know what to expect. Later that night, my sister told me "it might hurt, you might hate this" and all I could say was maybe.
When he got there he kissed my sister and said "is this her?" pointing at me. She said "that's her." now I know I was way too young to have sex with this guy, who I later found out was 27. I don't regret it though. And I wasn't very developed but I was tall for my age, so I am sure I looked older to him. Anyways, he kissed me a bit, grabbed my tits and my ass and I was so wet already. and he sat me down on the couch while he took his dick out and I just gasped. He wasn't aggressive but he wasn't shy either. He put it right in front of my mouth and I just took it in. I loved the feel of it, it was a little longer than my best friend's but not by much, so I couldn't fit it all in and he forced my head down. I gagged a little but not bad.
After a minute of that he stood me up and turned me around and pulled my pants down. I got on my knees on the couch with my arms propping me up on the back and felt him push his dick into my hole. I was so wet it slipped right in but was certainly tight. I'd been fingered enough and masturbated with my toothbrush holder a few times, so no cherry to pop thank God.
It went quick. He held my hips and fucked me hard from behind. I still remember how good it felt when his hips would slam into me. And after a minute, he stopped and jerked off til he came on my butt. I wasn't sure what to think of that but he wiped me off with some paper towels and we were done.
And that's the story of how I lost my virginity at the beach. My sister watched, and it was with a guy nearly twice my age, but it's still one of the best experiences I've had with sex. I fucked him a few more times that week, as did my sister, and her boyfriend never found out as far as I know.
