My First Time Pt. 01

The following events are true stories, they happened while I was in high school. All characters in these stories are over 18 years of age.

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Chapter One -Caught in the shower

Recently, a friend asked me to tell him about my first experiences with sex. Until being prompted, I had not thought about my early experiences for a long time. Once I began, so many memories and feelings came flooding back, I quickly realised that I had much more than one story to tell. Writing these stories has shown me just how much of my sexuality today is a direct result of these experiences, and how much they have influenced my life.

My first story begins with my very first experience at 18, it happened one night when my oldest brother, who is six years older than me, had some friends over. They were taking advantage of my parents being away, having a little bit of a party. I was having a shower before going to bed, when one of my brother's friends came into the bathroom, I was mortified, too stunned to say anything. I just stood there staring at him. We had a shower with transparent doors; nothing was hidden from view. I was so surprised that I didn't even try to cover up.

It was Grant who had come into the bathroom. I'd had a huge crush on him for as long as I could remember. I was feeling embarrassed and vulnerable, but as I stood there naked and wet, I started to feel something else as well. I was tingling, excited. I'd fantasised about Grant for such a long time, that we would fall in love and get married, school girl fantasies. But here was a man in the room with me, and I was totally naked. At first I wasn't sure what the heat was in my pussy, but being here like this was really turning me on.

As I came out of my confused state I realised he was staring at me too. I was a late developer, and my form hadn't fully come to fruition yet, but that didn't seem to stop Grant staring at my breasts, with now very erect and pointy nipples. We stared at one another for what seemed like ages, but couldn't have been more than thirty seconds.

Finally, I managed to ask him, "What are you doing in here?"

A silly question, obviously, and he replied with embarrassment, "I need to pee."

I still wasn't thinking, and I said, "Hurry up and pee, and get out so I can finish my shower."

Talking seemed to break the spell, and while he turned toward the toilet, he said "OK, sorry for interrupting you."

The sound of Grant peeing snapped me back to reality, and I thought to myself, "What the hell am I doing? I should tell him to get out and use the other bathroom." I didn't though, somewhere inside I was enjoying having him in the bathroom with me, and I didn't want it to end. Now that I could hear him peeing I wanted to see his dick, but he had his back to me.

He finished, zipped up and started to leave. The spell was really broken for me now, and I'd realised what the feeling was in my pussy, I was horny, I was wet, I was tingling, and I was having trouble breathing. I think I was already on the verge of orgasm, just from letting him look at my naked body. I wasn't going to let him leave yet.

I told him, "It isn't fair that you've seen me naked. To make it even you should let me see you naked too."

"No way is that going to happen," Grant said, after seeming to consider it for a moment, leaving me disappointed.

"At least let me see your penis."

He surprised me by taking his dick out. It was the first time I'd seen one this close, and in real life! Now I was finding it even harder to breathe, and I could tell my pussy was totally wet and my lips were opening. As I watched his erection got bigger and bigger, harder and harder. It was incredible, I stood there naked, transfixed. I really wanted to touch it, to feel it. I'd heard about headjobs from the girls at school, but the idea of having that in my mouth freaked me out, and I knew there was no way it was going to fit inside me.

I was tingling all over. "Can I touch it?" I croaked out.

He almost stuttered when he responded, "Yes, if you let me touch you as well."

I was about to touch a man's dick for the first time in my life. The thought had my whole body quivering, or it might have been the orgasm that made me shudder. And I hadn't even touched him yet! I stepped out of the shower and took his cock in my hand. As soon as I touched it, it seemed to jump at me, surprising me, and I let go.

Grant took my hand and put it back on his shaft. I wrapped my fingers around it and realized it was still growing! It seemed huge, it didn't fit in my hand, and it was still getting bigger! I was dizzy, and I came again as I started stroking it, feeling it, squeezing it. I didn't realize I was actually giving him a hand job; I was just enjoying the feel of a penis in my hand. It was hot, and hard, and silky smooth, I don't know how I expected one to feel, but this was perfect.

Then I felt his finger on my pussy. He slid one finger into me so easily, I was open and so wet after cumming twice, three times now, because I came again as his finger entered me. This one was even better than the previous two, because I had a cock in my hand and a finger in my pussy. I was almost delirious. Grant pushed a second finger into me, which didn't feel so nice in my virgin opening. He got a little rougher or clumsier as he thrust both fingers deeper into me, which hurt, and broke the spell for me.

I came back to my senses, and realized what we were doing, and where. I told him I had to go to bed, and that he should leave and let me dry. After he left, I noticed goo on my hand, and realized he'd cum in my hand! Ewwww, I thought, and cleaned up, brushed my teeth, and went to bed. Once in bed, I masturbated myself to several more orgasms, imagining it was Grant having me, and thinking about his cum in my hand. Now that I was horny again it wasn't gross anymore, I wanted to do it to him again, but this time I would watch and see when he came!

This was not only my first sexual contact with a man, but also where I learned that I enjoyed the reaction when people saw my naked body, that I had a strong exhibitionist streak. It was also my first experience with cum, and even though I was a little grossed out at first, it was only a matter of minutes before I realized that I actually liked having cum on me.

Chapter Two -Lessons in Sexuality

After my encounter with Grant in the shower, I was excited and confused. The more I thought about what had happened the more excited I became. It was exhilarating to remember holding Grant's dick in my hand, and almost overwhelming to think of what may happen next. But confusing as well, I didn't really understand what it meant, and I wondered what Grant was thinking about me.

The following day at school I told my closest friend, Stef, all about what had happened in the shower. She couldn't believe I'd held the dick of a man six years older than me in my hand, and made him cum!

With a mischievous grin, Stef said to me, "You should have given him a headjob."

I said, "I wouldn't know what to do, I'd do it wrong, and he'd laugh at me."

Stef told me, "I've never done it either." For all her boasting, she had never given a headjob either. "We should ask my friend Anne what to do, and then Grant won't laugh at you."

Somehow, it had become taken for granted that I would give Grant a headjob. I was nervous at the prospect, but becoming more enthusiastic with every passing moment.

Later we found Anne and convinced her to tell us her technique.

Anne said, "I can't really describe it well, you have to learn what to do by practicing. Basically, you have to take the head and as much of the shaft as possible in your mouth, don't take too much, because it will make you gag.

"Lick the head with your tongue, and suck, and move your head up and down, so it moves in and out of your mouth, pressing your lips and tongue against the shaft and head, but not touching it with your teeth.

"Make sure he tells you before he cums, it's really gross when they cum in your mouth.

"If you like you can watch next time I give my boyfriend a headjob."

This invitation astonished me, but Stef answered for both of us, simply saying, "OK".

As I thought about it I realized it would never happen. Anne would not have the courage to let us watch, and even if she did, Stef was all talk and would definitely chicken out.

After school, Anne invited us to her house, where we listened to music and talked about sex and headjobs. I learned the main reason Anne gave her boyfriend headjobs so frequently was because she was not yet ready to have sex. When she gave him headjobs he pressured her less about sex.

When we heard a knock at the door Anne said, "That will be my boyfriend, go behind the screen so he can't see you."

I was stunned, I hadn't expected this to really happen, and now it was. Stef and I just looked at one another; she looked just as shocked as me. It was too late to back out now and we both went behind the Venetian screen. We made ourselves comfortable on the floor while Anne left to let her boyfriend in.

When they returned and closed the bedroom door they started making out almost immediately. After a few moments of kissing they moved to the bed and their making out grew even hotter. They started by kissing while lying next to one another. He soon slid his hand up Anne's top, after a minute of feeling her breasts through her bra he reached behind her and unsnapped her bra. Then he slid his hand under Anne's top again, now feeling her naked boobs with his bare hands. They were both moaning and pressing their bodies together.

I'd made out a bit with a couple of boys, but nothing like this! At first I was uncomfortable watching, I don't know what I had expected, but I wasn't ready for anything this steamy! As I continued to watch I felt myself growing hotter, I was astonished at myself to realise the show on the bed was turning me on.

He took his hand out of Anne's top and slid it up under her skirt, not only did Anne let him do this, she moved her legs apart for him! I was wondering what his hands were doing to her under her skirt. Was he stroking her through her panties? Touching her bare pussy? Finger fucking her? Whatever it was, she was definitely enjoying it, and I was getting hotter watching and wondering.

I was wishing it was me on the bed with him, or with her for that matter. Which was a shocking realisation for me, I was so turned on by the sex show unfolding in front of me, I realised that I found both boys and girls sexy! As I was thinking about this, he pushed her top up, and she helped and slipped her top and her bra off over her head.

I found I enjoyed looking at her boobs, and I enjoyed watching him squeeze them. Then he moved his hand back up her skirt and she opened her legs even further this time, she looked like such a slut, lying there on the bed and it really made me hot. I was sure he was finger fucking her now, or playing with her clit, she'd rolled on to her back, with her legs spread wide, and I was hoping he would push her skirt up so we could get a view of what was happening. Instead, he started biting and licking Anne's nipples, and mine immediately reacted by becoming rock hard.

I looked at Stef next to me, and her eyes were glazed, no doubt just like mine, and I could see her nipples pressing through her top. Another shocking realisation hit me, not only was I attracted to girls, but I was attracted to Stef, my best friend! My attention was pulled back to the bed by Anne's moaning. God, she was cumming, Anne was having an orgasm right there on the bed in front of us. I was so jealous, I wanted it to be me, I wanted her boyfriend to be giving me orgasms, or I wanted to be the one sucking Anne's nipples and finger fucking her, I wanted it to be me causing her to arch her back up off the bed.

I was close to cumming too, and I reached out to Stef and put my hand on her thigh, and she put her hand over mine. Her thigh was hot, burning up, and she moved my hand, had me stroking her thigh. I looked at her and I could see in her eyes that the show on the bed was having exactly the same effect on her, she was totally aroused and discovering that her sexuality was not limited to boys either. Again we were drawn back to the bed as Anne had another orgasm, and this time she stopped her boyfriend from continuing, she was totally sated, and I was jealous again, my pussy was burning, and I couldn't stop myself any longer, I started rubbing myself through my shorts, my clit was terribly swollen, and it only took moments for me to have a shuddering, but totally silent orgasm.

Stef must have felt my orgasm when I clenched my hand, because she was looking at me and smiling, and then she started rubbing herself under her skirt as well, she looked at me as she masturbated. Within moments she had her own shuddering but silent orgasm. I watched as she came, and a look of complete bliss came over her face, and she squeezed my hand on her thigh convulsively, as her expression changed to a dreamy smile. Our eyes had been locked together as she came, and even though I hadn't touched her anywhere but her thigh, it felt as though I had given her the orgasm, as though I had shared it, and I knew she felt the same.

We heard Anne's boyfriend say something quietly, and Anne agreeing. He lay back on the bed, and Anne got on her hands and knees between his legs, giving us a perfect view from the side, as she unzipped and unbuttoned his pants and drew out his erection. She couldn't get it out at first, and had to pull his pants and undies down a little, and then it came out easily. It was big and hard, and it stuck straight up in the air. Anne kissed the tip, then let go and reached over and grabbed some tissues. Then she seemed to engulf his shaft, in one go she took half of the length of it in her mouth.

Behind the partition Stef and I moved closer together, so our thighs were pressing together, we were still holding hands. We each had our other hand on our respective crotch, Stef under her skirt, which had lifted, or she had lifted, so I could see her hand working her clit through her panties, and I was also working my clit through my shorts. I seemed to be in an almost constant state of orgasm, my best friend, and now that I noticed it, a beautiful girl, beside me masturbating, both of us watching an intense sex show involving another beautiful girl that I was sure would become a good friend after this experience.

Stef and I watched as Anne moved her head up and down on her boyfriend's cock. His shaft was wet and shiny where her mouth had been, and once she had it well lubricated she moved her hand up and down on the length of shaft that she couldn't fit in her mouth.

From the time Anne first took his dick in her mouth he was moaning, and telling her how good it felt, and how much he liked her sucking his cock. It seemed like only moments before he grunted out that he was about to cum, and Anne moved her mouth off his shaft and started stroking the entire length of it with her hand, positioning the tissues with her other hand, only just in time to catch squirt after squirt of cum shooting out of his dick.

Afterward, Anne and her boyfriend lay on the bed cuddling, and Stef and I lay back in each others arms behind the partition.

I was thinking about the things I had seen and felt. I'd discovered the voyeur in me, I'd enjoyed watching, and keeping it secret and hiding had just made it all the more exciting. More importantly, I had learnt that I was attracted to women as well as men, and in particular I was attracted to my best friend.

Chapter Three -Stef and I

After watching Anne and her boyfriend I had a very active fantasy life, all revolving around my friends. I fantasised about being with Anne's boyfriend, doing to him what Anne had done, and having him do to me what he had done to Anne. I fantasised about being with Anne in the same way, doing to her what he had done to her, and having her do it to me as well. But most of all I fantasised about Stef.

Stef and I had been right there together watching it. We'd shared the experience, and shared the discovery that our sexuality wasn't limited to boys. I'd looked into her eyes as she had cum, and that was a connection that was not easily dismissed. After that day, I often masturbated while fantasising about Stef, I imagined us being together and masturbating again, and I imagined kissing her, and being with her.

Over the next few weeks I would occasionally brush on the topic with Stef, but she was never very responsive. I began to believe that she had been caught in the heat of the moment; that the things we had done and what I had seen in her eyes were due to the passion created by watching Anne and her boyfriend. I was disappointed that she did not feel the same way I did, until one night while watching a love scene in a video; I saw her feelings for me surface again.

I wasn't going to let this chance pass. I asked her, "Do you ever think of the day we watched Anne and her boyfriend? Do you ever think of us holding hands?"

"I do", she said, filling me with relief that it wasn't just me.

"I think about it a lot when I'm alone, when I masturbate," I said.

"So do I," she said. "I enjoy remembering the two of us and the way we touched even more than I enjoy remembering Anne and her boyfriend."

I had butterflies. I didn't know what to do next, even though I now knew for sure that Stef felt exactly the same way as I did. There were so many things I wanted to do, so many things I wanted to say, but I couldn't do or say anything. My heart was beating so loudly that I could barely hear anything. I think I managed to tell her that I felt the same; that I thought about her a lot, about the two of us together.

I'm not sure how it happened, whether Stef started it or I did, but our lips were together, we were kissing. It was a tentative kiss, our lips gently touching one another. I could feel the warmth of her lips on mine, the wetness, I could taste her lip gloss, sweet, strawberry. I was suddenly on fire, my whole body tingling and burning; my heart even louder in my ears. I was kissing a girl, but more importantly I was kissing my best friend.

I had no idea where this might go, or what it might mean. All that I knew was that I was kissing my best friend, that it felt right, and that I didn't want it to end. Slowly the kiss became more energetic, more passionate. Our lips opened, our tongues met, gently touching one another. I could feel her tongue on my lips, and it sent tingles down my spine. The feelings spinning through my head were nothing like I had felt for boys, this was the ultimate expression of our friendship, that we could kiss one another, taste one another, experience everything of one another.

Our mouths parted more, our lips joined, our tongues seeking gently deeper, our breath intermingled and I could almost taste Stef as I breathed her in. Neither of us initiating the next step, it was instinctive and natural, both of us progressing together. Sensing what we each wanted, our hands were on one another's bodies now, touching, where her hand passed over my body it left tingles. I moved my hand under her top, the heat of her skin on my hand sent fire racing through my body.

I could feel an urgency growing in me, I wasn't sure at first what it was, but all of the sensations of our bodies touching, our tongues exploring, were ending between my legs, the urgency was sexual, but there was another aspect as well, touching Stef like this was incredibly erotic, it was turning me on, making me wet and opening my lips, but she was lighting up my heart as well.

I moved my hand over her body, finding her boob, squeezing her nipple, eliciting a moan from her, the first sound either of us had made. Touching her breasts was completely different to touching my own, it was so much more exciting to feel the firmness of Stef's boobs, and they were so much larger than my own, filling my hand. I squeezed them gently, feeling them move against my hand. Stef found my nipple and squeezed, sending electricity straight to my pussy, I let out an involuntary moan, and understood why she moaned.