tagFirst TimeMy First Time Pt. 02

My First Time Pt. 02


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 Four - Flirting and Teasing

With each encounter I was learning more about my sexuality, more about the affect I had on people, and my libido seemed to be growing stronger. I was starting to feel sexier, more sexual, and my behaviour began to change as a result. I enjoyed wearing sexier clothes and I enjoyed flirting with boys, especially my brothers' friends.

I enjoyed the reactions I got from my brothers' friends, especially my oldest brother's, because they were men, not boys. For the most part I don't think they even noticed I was flirting with them, they just considered me their friend's younger sister; I wasn't really a girl to them. With some of them I did get a reaction, which always made me tingle and encouraged me to be even more flirtatious.

I began to hang around more when my oldest brother had friends over and I took to wearing more revealing clothes. In the evenings I would wear just my pyjamas, which were very open and loose, affording views down my top as well as the occasional glimpse up my shorts. Being pyjamas, I naturally didn't wear underwear, making the view that much more interesting I hoped. My pyjama shorts were made of a material which clung to my body despite being loose, showing off my curves.

I think all of my brothers' friends gained a very intimate knowledge of what my boobs looked like over the next couple of years, and some had an even more intimate knowledge of my body. Wearing sexy clothes around my brothers' friends made my pussy tingle, especially when I would lean over letting them see down my top.

One occasion particularly stands out in my memory. My oldest brother had some friends over and I came to hang out with them. I had a brand new Tamagotchi that I was playing with, and one of my brother's friends grabbed it from me and wouldn't give it back. This evolved into a game of piggy in the middle, with me as the piggy. I wanted my tamagotchi back, I was worried my pet might die, but I wasn't too upset as I was really enjoying the attention and I got to wrestle with my brother's friends. The attention and physical contact were really turning me on, I was enjoying grabbing the boys and pressing my body against them.

At some point the tamagotchi was passed to one of the boys, David, sitting in a chair. This was my chance and I grabbed it, I climbed up on him and reached for the tamagotchi, he had it in his hands above and behind his head. As I leaned over and reached past his head my top was completely open, giving him a perfect view of my boobs and very erect nipples. I knew what was happening and was completely shameless, I plunged my chest right into his face as I reached for my tamagotchi, I could feel his stubble on my breasts. This had the desired effect, distracting him from the Tamagotchi, and I triumphantly claimed it back.

Once I had my Tamagotchi back I stayed in David's lap and played with it for a while, hanging out with my brother and his friends, while they drank beer and got high. I know David enjoyed having my boobs in his face and having me in his lap, because when I sat in his lap he had an erection and while I was there I could feel it pressing against me and getting harder and harder.

While in his lap I found a lot of excuses to wriggle and squirm, moving my arse and pussy against his erection. I was sure he enjoyed my wriggling because if I was still too long he would tickle me, causing me to wriggle against him. I was enjoying the sensation of his erection pressing against me and enjoyed even more that he was encouraging me. I was very aroused, close to cumming; I could feel my pussy twitch again whenever I felt his dick press against me.

Eventually my brother told me to get lost because it was late, and as I got off David's lap I put my hand in his lap to keep my balance, right on his erection, and I had a good feel and squeezed. As I felt his dick I came very quietly, I hoped no one could see the wetness in my shorts. I rushed to my bedroom where I masturbated myself to several more orgasms.

While there were many occasions when I teased my brothers' friends, it never went any further than sitting in their laps or wrestling, but it wasn't just my brothers' friends that I could tease.

Stef, Anne and I would often spend the night at one another's homes, most often at Stef's because her dad was away a lot. We'd hang around in our underwear or pyjamas. Usually Stef would get rid of her brother for the night, which always disappointed me, I loved it when he was there and saw me in my underwear, in fact, I loved it when anyone saw me in my underwear. I'd taken to wearing very brief underwear, not g-strings but getting there, and brief singlet tops.

On one of these nights we were in the living room watching movies, we'd changed into our night clothes and we were all just wearing brief panties and little singlet tops. Stef and Anne weren't show offs like me, and would wear more clothes when the boys were around, but when we were alone we would all just get comfortable in our underwear.

Tonight was different though, because the boys were home, as we found out when they came into the living room. My pussy was immediately tingling and moistening, my nipples erect.

Stef's brother said, "Give me the remote stupid, we aren't going to watch any of your pathetic chick flicks."

I was proud of Stef when she answered, "Fuck off, we were here first." Then she asked, pointing at his friend, "What are you even doing here? You're supposed to be at his place."

He grabbed the remote and wouldn't let us have it back. Stef and Anne tackled Stef's brother as he threw the remote to his friend, which prompted me to grab his friend. He held the remote away from me and I tried to grab it, but I couldn't reach and he was stronger than me, being a year older and a boy. But I tried my hardest, managing to rub myself all over him in the process. It was fantastically erotic, Stef and Anne half naked and on top of one boy, with arms and body parts everywhere, and me rubbing my whole body all over this boy. I could feel his hands on my breasts, which just made me more excited, I was trying to get my top to lift up so he could feel my boobs without the shirt between us, but I could not make it happen without it being obvious.

Eventually I jumped on him, wrapping my legs around his hips, pressing my crotch against his crotch. I couldn't be sure but I thought he had an erection, which made me think I was having the same effect on him as he was having on me. He fell over on his back, and I landed on him, straddling him, with our crotches pressing against one another. I was in a total daze, and now I knew for sure he was hard, I could feel his erection pressing against my wet pussy.

Stef and Anne were telling me to get the remote before either of the boys broke free, which made mine start struggling. He tried to get me off by thrusting his hips up, as a result pressing his erection into my by now sopping pussy. I knew he was enjoying it as much as me, because neither of us was concerned with the remote for the time being. I was practically riding this boy cowgirl with three other people in the room, this thought combined with his thrusts pushed me over the edge and I came while riding him.

After I came I could think a little more clearly, and knew I had to get the remote back. I got my knees on the ground and crawled up him till I was sitting on his chest with my wet pussy practically in his face, the closeness and the possibility that he could smell my mustiness just making me wetter. The remote was in his hand above his head, I could reach it, and as I started to reach out for it, he moved it back down behind me where I couldn't see it. I reached back to get it and felt around, and found my hand on his dick, which made him grunt. He was totally hard. I was shocked and reflexively pulled my hand away.

I looked at the others, and they were in the midst of a huge struggle to hold onto Stef's brother, and weren't paying any attention to us at all. I put my hand back on his cock and wrapped my hand around it through his shorts. It was very hard, but not as big as Grant's. I stroked his shaft through his pants and watched his face as I did it. He struggled at first, then moaned and relaxed as he realised what I was doing, he closed his eyes, and I watched him. His expression was completely blissful, as I stroked he began to thrust his hips off the ground, not to push me off this time, but to increase the pressure of my hand against his cock. At the same time I was grinding my pussy against his chest, I was on the verge of cumming again as well. I watched his face as he came, and seeing the expressions passing over his face brought me to orgasm as well.

We sat there for a while, dazed, until I remembered the remote. He had dropped it and I grabbed it and got off him. As I got off I noticed a damp patch on his shirt where my pussy had been, as well as a wet spot in his shorts. Once I was off him he got up quickly and left the room in a hurry. Stef told her brother to get lost and keep out unless they wanted to get beaten up again.

"What's up? You look like you're stoned," Stef asked.

"I just gave your brother's friend a hand job while we wrestled for the remote."

Anne was incredulous, just saying, "No way!"

"You couldn't have, we would have seen!" Stef said. Then she laughed and said, "You are such a tart, they'll be back to get another beating now."

Then I told them the whole story, which seemed to excite them both.

After that happened there were rumours about me at school and I realised I had to be more careful. The rumours didn't bother me and were easy enough to stop by telling a slightly different version of the truth. Still, I didn't want everyone knowing my business. Since then I have been a lot more discrete in my adventures.

Chapter Five - My First Blowjob

After watching Anne give her boyfriend a headjob I was determined to give Grant a headjob at the next possible opportunity, and I knew that I wanted him inside me as well. While Anne gave her boyfriend headjobs to stop him pressuring her for sex, I was excited at the possibility of giving Grant a headjob, the thought of having him in my mouth was very arousing and I often fantasised about it when I masturbated.

I hadn't seen Grant in months and when I asked my brother about him I just got a stony silence. I never found out why but I never saw Grant again. I suspect that my brother found out something about what happened in the shower that night and had cut him as a friend. I was crushed, after what happened I had come to think of Grant almost as my boyfriend, and I wasn't sure whether I would ever give a headjob if Grant didn't come back. But there's nothing like replacing one crush with another.

While my oldest brother was on holiday from university, he had a friend, Rob, come up for a while. They were going on a trip together for the holidays and Rob was staying with us until they left. Rob had moved away from Sydney to go to university a couple of years ago. I hadn't seen Rob in ages, and when he'd left I had a devastating school girl crush on him.

I noticed Rob had changed when I first saw him, he was really big now, he played football for the university team and he'd really filled out. I was so excited he was back and the timing was perfect for me, I decided I would give him a headjob if I got the opportunity. I could have been with lots of boys my age, but I was spoiled by having a brother six years older than me, I knew men and boys simply didn't interest me any more.

For the first couple of days when Rob arrived I followed him around like a lost puppy. I overheard my mum telling someone how cute it was that I had a crush on him. I'm glad she thought it was cute, when actually it was anything but! When Rob had first arrived he didn't pay much attention to me at all, but I had softened him up or maybe hardened him up!

I used all of my well practiced tricks, sitting in his lap a lot, wriggling my arse against his dick, and letting him look down my top and up my skirt every time I could get away with it. I wore my briefest underwear, wishing for something sexy and lacy, but I wasn't comfortable buying sexy lingerie. And, of course, I brushed my boobs and nipples against him without a bra at every opportunity.

Despite all this, Rob continued to show very little reaction to me; no doubt he thought it was cute that I had a crush on him as well. It changed one night when I was wriggling my arse against him, I felt him become uncomfortable, I could feel his dick getting hard under me, and it turned me on totally.

Mum called me for something and I didn't want to rush things, knowing he was uncomfortable, so I answered her and rushed off. It took about half an hour to take care of the chores for mum, and when I came back I sat in Rob's lap again. He wasn't hard when I sat down, but after wriggling a little, and leaning over so he could see down my top a few times, I felt him get hard again.

This time he didn't get uncomfortable or push me off! I stopped wriggling and just moved around a little, enough so we could both feel his erection pressing against me, but not so much that people might realise what I was doing. I knew Rob was enjoying it because his dick was really hard now, and pushing against my arse.

As always, my brother kicked me out and I went and showered. I was hoping Rob would find me just like Grant had, but no such luck tonight. I went to bed and fantasised about Rob, remembering how his hard cock had felt pressed against me, and masturbated until I came and could finally sleep, exhausted.

In the morning I waited until Rob went into the shower and went in after him, since he wasn't going to come to me I went to him.

He cried out in surprise, "Hey, I'm having a shower, get out!"

He had soap all over him, with a lot of soap on his erect dick, which was standing straight up in the air. I think I had caught him masturbating, and wondered whether he fantasised about me the way I had about him last night!

"Sorry, I hadn't realised you were in here." Trying to distract him I asked, "How did you get so muscular?"

"Working out for football," he said. "You have to leave. How would you feel if I came in for a chat while you were in the shower?"

That was exactly what I wanted, but I couldn't tell him that, instead I said, "Well, I guess it would be OK, it would make us even now that I have seen you naked."

Surprised, he asked, "What?"

I repeated myself, "I've seen you naked and it would make us even if you saw me naked."

He seemed a little confused by my logic, so I took the opportunity to chat for a few minutes about other things, asking him about life in Canberra, and trying not to stare too obviously at his erection. I wasn't going to leave until he knew that I liked seeing him naked, hoping this would encourage him to come in while I was in the shower. He stayed hard the whole time, and he never once tried to cover himself from me, so I knew he liked me being there as much as I did.

A little later I had a shower, I was hoping Rob would come in, but I was disappointed.

That night, I couldn't wait until the usual time for my evening shower; I was too excited at the possibility of Rob seeing me naked. Tonight I was determined that Rob should come in, and I searched the house for him and my brother.

When I found them, I told them, "I'm going to have a shower."

My brother gave me a weird look and said, "Why would we care if you are going to have a shower?"

I hoped Rob cared and left for my shower. While I was in the shower the door opened and Rob came in. I tried to act casual, and went on showering. I was sure he could hear my heart beating; I was so excited to have him in the room with me while I was naked.

"Hi," I said, and continued to wash. I washed my breasts with soap again, because I wanted him to see me touching myself. I washed my bum as well, but didn't have the courage to wash my pussy while he was watching.

He looked like he was about to leave, so I said, "You have to stay for as long as I did or we won't be even." I was surprised, but this worked, and he stayed, and we chatted as if nothing unusual was happening. Something was happening though, I was tingling all over, my pussy was on fire, it was completely wet and I could see an erection pressing against his pants.

I rinsed off and stepped out of the shower. I was too scared to say anything now in case my voice quavered, I was standing right in front of a man, completely naked, he had an erection and my pussy was burning, it was torture, I wanted him to grab me and have me right there! Instead, I asked him to pass me my towel, which he did and then he left. My God! My whole body was quivering, I was right on the brink of orgasm and masturbated right there in the bathroom, I didn't have time to go to my bedroom.

I went to my room and put my pyjamas on, and hung around hoping Rob would have a shower. Eventually, he did and I waited as long as I could and went in. I caught him masturbating again, and this time he still had his hand on his dick, which immediately set my pussy on fire all over again!

I asked him, "Do you think about anything when you masturbate?"

"Yes," he answered. "Sometimes I think about you naked in the shower, and sometimes I think about you sitting on my lap."

I couldn't believe it, he really was fantasising about me!

"Can I watch you do it?" I asked.

He started masturbating again, I was ready to cum again, it was intense watching a man masturbate, knowing it was turning him on that I was there and that I was watching. I opened the glass door so I could see better, and went on watching.

After a few moments, I asked, "Do you mind if I do it?"

"OK," he answered, and moved his hand away from his dick.

I reached in and put my hand around his shaft, it was so hot when I touched it, and God I was so wet. I knew that everything was going to happen soon, that the cock in my hand would soon be in my mouth and soon be in my pussy. Knowing that, and feeling his erection in my hand I came.

I think he mistook my orgasm for hesitation and he took my hand in his and started me stroking my hand up and down the length of his shaft. He took his hand away and I was wanking him on my own, this was the first time I had had a naked dick in my hand, my first real hand job. I was hot; I was cumming constantly, wanking a man in the shower. He started to breathe hard, and let his head fall back, and let out a long low moan.

He opened his eyes and took my other hand, and put the palm over the head of his penis and moved it around in a circular motion. He moaned again and let my hand go, closing his eyes, letting his head fall back again. His expression was rapturous; it made me cum again seeing the effect I was having on him, seeing that he enjoyed my hand job so much.

Then he let out what was almost a growl and shot his hot load on my hand, it seemed he would never stop cumming. When finally he did stop I pulled my hand back and wiped his cum on my pants, I wanted his cum near my pussy. I kept rubbing the head of his dick with my other hand, and it twitched with each stroke, a twitch that seemed to run through his whole body and cause a little grunt each time.

Later, Rob found me, and said, "We can't see each other in the bathroom anymore, we'll get caught. And you can't sit on my lap anymore either, people will know something is going on with us."

I was devastated but managed to say, "Mum already thinks I have a cute little crush on you. No one will notice anything except that."

Rob replied, "It's different now, people will notice because we both like it so much."

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