How I lost [m]y virginity. Xpost from /r/erotica [f] | 2016

Oops, title should be: m/f/f/f/f

This isn't really Erotica, it's a true story of how I lost my virginity. I didn't know where else to post it.

It's long and descriptive, with the perspective of a terrified virgin boy with hardly any experience beyond kissing - my perspective. My goal was to try and describe how I was feeling, what I was thinking, etc. Please don't judge me too bad though because I don't write erotica or anything like that.

I know it sounds crazy towards the end but I sometimes can't believe it happened either. Depending on how well people like it, I may continue the story, because there is more to it than where I left off.

I hope you enjoy. It's a long read. I had to split it up into two parts.

Names have been changed, but the story is real.

PART 1

I used to go visit my aunt alot when I was younger. She seemed to move all over the place, and one of the places she lived was about 2 hours away in a neighborhood where the houses were within just a few feet of each other.

She had several cats and a dog, a creek in the back yard, and dial up internet. But the house just next door lived a girl about the same age as me, and so every time I visited we would play together. Her name is Ashley.

We would play in the creek, catch crawdads, play with the cats and dog, you know just kids having fun. She was kind of a tomboy in that regard. She didn't mind getting dirty, playing in the creek or getting dirt on her from playing with the dogs. This went on for a few years, just two kids having fun, playing together. We got to be pretty good friends. We'd stay up late watching movies and playing on the internet. We would just talk about life from the perspective of young kids. It got to the point where, even when I wasn't there visiting, we'd talk to each other on the phone.

I remember one day, we were walking along the street and she told me she was depressed. I asked her why and she said that she really liked some guy but couldn’t be with him because he lived so far away, and her mom told her not to get attached. I was so oblivious I just kind of shrugged and told her I’m sorry.

"Was she talking about me? No, I doubt it. We're just friends" I told myself.

After that, every time I would visit she would do things or say things that, back then I had no idea what was going on but now, I knew exactly what she was up to. She would give me back massages and then want me to give them to her. She would wear really tight pants or shorts and lay on the couch up against me. After a while, she would even ask me if I liked her butt (she danced so she had nice legs and such a cute little butt). I would laugh and grab it and squeeze it, just sort of playing around. I guess I wasn't taking her too seriously. But every time something like that happened, she went from playful to kind of quiet and serious.

"Oh, did I make her mad?" I thought.

One day I got invited to her birthday party. I don’t think I knew what to expect and now that I think about it, I doubt our parents did either. I showed up at her party which was at this nice condo with a pool. I brought her a card with some money in it, which I had legitimately earned from doing chores at home. We had a cookout, hamburgers hotdogs, and after we ate, changed into our bathing suits and went swimming. When I walked outside and saw her in her little two piece pink bikini, my jaw hit the floor! I had never really seen her in such a little amount clothing. I just remember seeing those curves on her and thinking "WOW!"

She always had a nice butt, but her breasts had really developed alot more since the last time I saw her. Or maybe it was just the bikini she was wearing. All I know is, it was hard for me keep my eyes off her.

I just had to not pay so much attention because boys can have big problems if we let our gaze wonder too much, if you know what I mean. So we just swam, had fun, played games like Marko-Polo in the pool. There were just a few of us there, maybe 5-6 total. But I was the only boy there, and the rest were her girlfriends. I think some of them left later on.

Well it was getting dark now and so we went inside the condo. I remember just having a hard time not staring at her and she would look back at me and catch me looking at her, and she would just smile. I have no idea where her parents went but I just don’t remember them being anywhere around. She went into one of the rooms with a bunch of her girlfriends for a little while and wouldn’t let me come in. So I just stayed in the living area watching TV and I could hear them in there giggling and making lots of noise.

I guess she was reading her birthday cards because at one point she came out and jumped on top of me, still in her bikini, and gave me a hard time about what I said in her card. I wrote sort of a smart-ass remark about how I hope she enjoys my gift because I worked hard to earn it or something like that. So she jumped on top of me, her legs straddling over me, and I just about had a heart attack because her breasts were right in my face, and she was basically sitting in my lap. Wow. My heart started to race, and I don't know why but I instinctively placed my hands on her legs.

She gave me this sort of, playful-angry expression like she was upset but not really. She asked me something and I honestly had no idea what she said, because I was in such a daze, because she's in her bikini on top of me, so I just shrugged and said "Um, sorry?"

So she gave me a light slap, it wasn't hard at all, just a playful one, jumped off and ran back off into the bedroom again. I had to readjust myself.

A little while later, I found myself in the bedroom with her and her girlfriends. We were just kind of playing and having fun, until they put me and her into the closet and shut the door. I could hear them outside the door laughing and teasing about how we were going to have sex.

"Wait, what??" I thought. I started to get nervous.

They kept opening and closing the door, I guess they were hoping we'd start getting it on and were trying to catch us in the act or something. All I could do was sit there, heart racing, not sure what to do because I was still a virgin and I was deathly afraid to make a move, especially with other people – other GIRLS around!

I just remember how much I wanted to make a move on her in the closet because she was sitting there so sexy in her pink bikini, still sort of wet from the pool. I'm not sure what happened but all of a sudden, I really liked her.

Wait, what's going on? She's just a friend and I don't even know if she likes me back. So I sat there, too chicken to do anything, my heart pounding as the girls continue to fling the door open and close it back again, laughing and talking amongst each other.

Now it was time to get ready for bed (or so I thought) and we took showers and changed into our sleeping clothes. I wore shorts and a white T-shirt. She wore these super short shorts that just showed off her cute butt so good, and a spaghetti-strap top that also showed off her breasts incredibly well. Again, I was just like "WOW".

We all slept in sleeping bags in the main living area. I got into my sleeping bag, ashamed, annoyed, still kind of nervous from what happened earlier. The lights went out and I could hear the girls whispering. I laid there for a little while just thinking to myself.

"What am I supposed to do?" I thought, feeling kind of hopeless now.

All of a sudden I hear someone getting out of their sleeping bag and walk over to mine. It was Ashley. She got down on the floor and started whispering something to me. She was telling me some kind of “plan”. It went something like this – “My friend thinks we like each other so let’s pretend kiss so we can fool her!”

Me being the oblivious idiot that I was, I said "Ok", fully intending on pretending to kiss her. She got into the sleeping bag with me and we both went under a little further so no one could see. Before I could even try to pretend kiss her, she put her arms around my neck and pressed her lips against mine.

WOW!! Where the heck did this come from??

Her lips were on mine and nothing in the entire universe could have mattered at that moment. We kissed, and it was like electricity was coursing through my entire body, and it immediately made me quiver. I mean, I had kissed a few girls before but not like this. It was passionate, heated, and so damn hot.

So there we were, making out inside of a sleeping bag, with a bunch of her girlfriends in the same room, probably watching and listening. My heart was racing a mile a minute.

“Ok” I thought, “I am kissing her! Wow. Ok, now what? Should I just keep kissing her? Should I touch her? Oh my god this is so great, I like her so much, I can’t believe I’m kissing her!”

I could smell her hair, freshly washed from the shower. I don’t know if it was just shampoo or if she put on some kind of perfume but she smelled soo good, it made my mouth water. I finally mustered up the courage to put a shaky, nervous hand on her hip. We’re still kissing! She must be ok with it. So I slowly moved my hand to her belly. Mmm such a nice firm tummy. She has a great body from all that dancing.

I move my hand up a little more, and I can feel her heart beating almost as fast as mine. I inch my hand up ever so slowly, as if moving slower would make her not notice my intentions to move up her shirt or something. Ok here goes nothing. I close the distance with my hand and move it up her shirt.

Yes! My first boob! Wow it's so soft! I gave her breast a little squeeze and her nipple hardened under my hand. We were both panting now and things were heating up. I kept my hand there for a while as we continued to make out, reveling in the excitement and actually being pretty content with just making out and getting my first boob. Then she grabbed my hand. Wait, is something wrong? Did I go too far? She took my hand and moved it away. Yep, I blew it! DAMNIT!

Wait, she’s moving it further down. She moved my hand into her shorts and – OH MY GOD!

Another shock of incredible electricity coursed through me as my fingers touched something else! It was wet – incredibly wet, and really soft. I just about exploded, and it felt like my heart was literally in my throat! As my fingers touched her incredibly wet pussy, she moaned again and we began kissing ever so passionately, our tongues going crazy inside one another’s mouth.

I didn’t really know what I was supposed to do, so I just kept rubbing her with my fingers, kissing her, wondering what will happen next. The excitement was incredible. Wow I couldn’t believe I was fingering her! Oh my God I want to explore her!

My finger slowly entered inside of her and she moaned again. GOD! It’s so warm inside! I began to finger-fuck her and it was starting to drive her crazy. Then she stopped, put my hand aside, and took off her shorts. I watched wide-eyed, as I saw her naked exposed body reveal itself to me. Wow, it’s so amazing. I’ve never seen a girl naked before. I mean, I’ve watched porn before, but I’ve never experienced the real thing! I couldn’t stop staring at her.

She looked at me with a smile and told me to take mine off. I had an incredible erection that I had sort of forgotten about until just now.

“Oh my God I can’t believe this is really about to happen” is all I could think to myself as my shaky hands somehow worked my shorts and underwear off. She smiled, laid back down and pulled me on top of her. I was so nervous, I was shaking all over. She moved her body while guiding mine until I felt that soft and incredibly wet pussy press up against my insanely hard cock. I felt it rub on the underside of my shaft, but it felt different than when my fingers were touching it. It felt so much better against my cock.

“Mmm, put it inside me now” she said. She grabbed it as I looked down, and with her help I watched my head slowly disappear inside her pussy. OH MY GOD!!

She moaned, and that urged me to push in all the way. "Oh my god I'm inside her!" kept racing through my head along with “This feels so amazing!” We started to fuck slowly, but it wasn’t long until I was already about to cum. NO! Not now! I can’t or she’ll laugh at me and this whole experience will be just a funny story at my expense. She’ll tell her friends, they’ll laugh and make fun of me and I’ll lose my chance with her. I Can’t give in!

But then I snap back to what’s happening, I’m looking at her sexy naked body, her legs spread to ME, and the sight of my cock deep inside her pussy – which looks so cute and amazing.

I know that feeling when I’m about to cum. And I would just feel like such a failure if I came now. But I can’t help it, this feels a million times better than anything I have ever felt before! Now I have stopped, I'm still inside her, not moving, and I have now stalled for longer than I should.

“What’s wrong?” she says.

What do I do?! I’m screwed.