My first Time_(100)
Introduction:
The first time I had sex
I was standing in front of a mirror in my room in my suit. I was slender with a flat stomach. I looked at my ass and noticed it too had begun to fill out. I had a little bubble butt. My boobs looked a little out of place with the rest of my body. In this top they were spilling out the sides some and I had a pronounced cleavage. I knew I would probably have to get at least a 34C. I was going over to a friends house today to swim. I had been over there recently and had noticed how her father was a little nervous around me and when he was outside with us I would catch him staring at me.
I went to the kitchen to find my mom or dad to take me over to my friends house. My brother was in there getting a drink. He was 4 years older then me. He didn’t say a word as I walked in the room. I saw his eyes go up and down my body. He looked at my boobs the most. He had been doing this a lot lately. He had been giving me quite a few hugs lately and I knew it was so he could feel my boobs. My dad walked into the room and took one look at me and just shook his head. I asked him if he could drive me, but before he could answer my brother said he could. My dad made me put a tshirt on before we left and he told my mom to please take me shopping to get a swimsuit that fits.
As we drove to my friend’s house I saw that my brother was stealing little looks at me. He made the comment that I had grown a lot in the past year and I knew he didn’t mean my height. He asked me if boys in school were trying to get me to hook up and stuff. I just smiled and said some. I told him that the boys were always trying to hug me and I knew all they wanted was to feel my boobs. He swallowed hard at that. I said some were even bold enough to fake like they bumped into me and would grab them. He didn’t say much after that and dropped me off. I told him I would call him later to come pick me up.
I had fun at my friends house as we enjoyed the pool. Her boobs were much smaller then mine and she was on the skinny side. Her dad sat in a lounge chair on the patio with sunglasses on reading a magazine. I was pretty sure he was trying not to be too obvious about staring at my boobs. Once I noticed the magazine was upside down and I was about to say something to him when he quickly got up and went inside. That happened right after I had jumped off the diving board and when I came up to the surface one of my boobs had popped out of my top. My friend noticed and pointed and laughed. I giggled and tucked it back in my barely there top.
It was getting late and I called my brother to come pick me up. I thanked my friend for inviting me and on purpose I gave her dad a hug so he could feel how big my 13 yr old boobs were. I hopped in the car and my brother drove us home. I hadn’t put the tshirt back on. He kept looking at my cleavage and the side swell of my boob that wasn’t cover by the top. I stretched a couple of time making sure he got a good show. I was teasing him of course. It did make me a little excited knowing that my friend’s dad and now my brother were looking at me in that way.
I took a shower and mom had fixed dinner. We watched some movie then I went to bed. It was always warm in my room so I didn’t wear much to bed. I had a little tank top on and panties, that’s it. All I had on my bed was a sheet and that was thrown back most of the night. I had just started to drift off to sleep when I heard something. My brothers room and mine were connected by a bathroom. Someone had come into my room from there. They stood next to my bed for a moment then laid down next to me. It was my brother.
I turned my head and asked him what the hell he was doing. He told me to be quiet, that he just couldn’t help it anymore. He whispered to me that after this afternoon seeing me in that swimsuit he had made a decision. He said he just had to feel my boobs for himself first hand. He said he would be gentle and asked me if he could touch them just for a minute. My heart was pounding and I had to swallow before I could talk. I was very nervous and told him it was OK and he could touch them but just for a minute. We were in a spooning position on my bed and I felt his left arm reach over me and he took my left breast in his hand. I felt the heat of his hand through the thin fabric of my top. He gently squeezed my soft breast and I closed my eyes.
He whispered to me that he couldn’t believe how big they had gotten. He said I was bigger then most of the girls in his class. Having my breast in his hand felt great but then he let go of it. I thought he might be done and I was a little disappointed, but he wasn’t. He moved his hand down and slipped it under my top. His hand moved back to my naked breast and he grabbed it again. This was a lot better then before. Feeling his skin on my skin was electric. Soon his fingers found my nipple. It was rock hard and he pinched and pulled on it. I think I might have even moaned a little at that. He made sure that both my left and right boob got attention, squeezing the round fleshy globes and pulling on my big nipples. I had told him for only a minute but now I didn’t want him to stop, but he did. He kissed me on the cheek and said thanks and then left my room going back to his.
I was breathing hard and now I would have a heck of a time going to sleep. One of my hands made its way down to my panties and went in them. I was very wet and my fingers found my swollen clit. I had been masturbating more often lately and it didn’t take long for me to make myself cum. I shook with my orgasm thinking about my brothers hands on my breasts. Relaxed now I rolled over and went to sleep. I wondered if that was a one time encounter or if he would do it again.
The next day I was a little nervous. I wasn’t feeling guilty, but brothers weren’t supposed to feel their sisters naked boobs, were they? I smiled at him and he smiled at me when I saw him in the kitchen. My mom and dad were in there and I knew my dad would kill my brother if he knew our little secret. If we were going to continue our play we would have to be careful not to get caught. Later that night I tried to stay calm and not look like I was excited about going to bed. As I lay there I slowed my breathing and waited. I thought he wasn’t going to visit me when finally the door to the bathroom opened and he walked in my room. He crawled into bed with me again. He whispered that he had to make sure mom and dad were asleep before coming in here. I just nodded and then I took off my sleep top. I was on my back and he had full access to my boobs. He started to squeeze them and pulled on the nipples. Then he did something I didn’t expect. He leaned down and he took one of my 13 yr old nipples into his mouth.
His mouth was hot and wet and he flicked his tongue on my nipple. He slurped and sucked on it then did the same to the other one. He played with my boobs like this for maybe 30 min then gave me a kiss and left. Having him suck on my nipples felt so good. I pulled on them myself with one hand while the other played with my pussy and clit. I came again like the night before. I was so happy my brother had decided to continue our nightly play. And continue it he did, almost every night for the rest of the summer.
After a few weeks of boob play one night while he was sucking on a nipple I felt his hand on my stomach. It slowly moved lowered until it reached the edge of my panties. He hesitated just for a moment then slowly slid his hand under the waistband continued down until his fingers touched the lips of my pussy. I wanted him to touch me the same way I touched myself. This was a big step beyond just playing with his sister’s boobies. He let go of my nipple just long enough to ask me if I wanted him to go further. I just nodded my head. His fingers parted my lips and he could tell how wet I was. He used his middle finger to trace my tight opening. He slowly pushed it inside me but stopped when he felt an obstruction. I was still very much a virgin. He pulled his finger out and moved it up to my clit. Like my boobs it was big for my age. It was sticking out of it’s little hood and he played with it as he rubbed my pussy. That sent me over the edge and for the first time I came from another person’s efforts. My brother’s efforts.
After I finished and relaxed he kissed me and left. Knowing that he had actually touched my pussy and had given me an orgasm raised our game to a higher level. It felt much more taboo now and that much bigger of a secret. I kept praying that our parents didn’t have a clue about our nightly activity. I wanted it to continue and though I didn’t think about it I probably knew where it was heading.
It had been a couple of weeks since he had started playing with my pussy. I had started going to bed naked because it gave him easier access to me. I was waiting for him in bed like usual one night. He came into my room and climbed in with me. I rolled toward him to give him a hug. I liked him to hold my naked body close. We had started french kissing as well. He told me I was getting very good at that. Our tongues would dance in each others mouths and it just added to the passion. As he pulled me close I immediately knew he was nude as well. Up to this point he usually wore a tshirt and/or at least his boxers. Tonight my brother was as naked as I was.
I felt the warmth of his naked body press against mine. He had something in mind and I wasn’t sure what. Summer was almost over and school would be starting soon. I would also be 14 soon. I knew his cock got hard when he played with me. I had never seen it and of course never touched it. Now it was between us and I could feel it swelling. He had his hands on my ass pulling me close and I did the same to him. We were kissing and my boobs were pressed into his chest. I could feel his fingers go between my ass cheeks seeking out my pussy. His cock was super hard now and from what I could tell it was huge. I had never touched a cock and had only seen a couple of them by accident. Some of my friends had played with boys and from what they had told me about how big they were my brother’s dwarfed all of them.
He broke our kiss as he played with my pussy. He was breathing hard and asked me to do something for him. I said OK and he asked me if I would hold his cock in my hands. He said only if I wanted too but he sure would like it if I did. I nodded and asked him to show me how. He rolled over on his back and I sat up some. Even though the room was dark I could still see some and for the first time I got a good look at his now fully erect cock. It was laying on his stomach and almost reached his belly button. It was as big around as my arm. I was just staring at it in awe when he took my hand and placed it on it. It was hot and it throbbed. The skin was so soft yet hard beneath the surface. It felt alive and not like anything I had felt before. I slowly ran my hand up the length of it until I reached the head. That part was very swollen and big. I touched the tip of it where he peed and felt a hot slick discharge coming out of it.
His cock was much too big for just one of my hands so I used both of them to play with it. He showed me how he liked it to be stroked. As I did what I was told he continued to play with my pussy. I played with his cock for maybe 30 min and I heard him groan. He said that he was going to cum soon. I knew what that meant and though I had never seen it my friends had told me about it. His cock would shoot his cum out of the end of it. Now that he was this close to actually doing that I wanted to see it. I stroked it a little faster and he closed his eyes. I had both of my hands wrapped around it going up and down when I felt it jerk. I wasn’t sure what would happen, maybe a few drops. A huge rope of cum shot out the end of it into my hair. I didn’t let go of it as another large blast hit the headboard. There was so much of it I was in shock. I wasn’t sure if it would ever end as his poured out his load. It was all over both of us.
I was speechless and just sat there. He was breathing hard and then opened his eyes and looked at us. He laughed and took me by the hand and led me to the bathroom. We got some wet washcloths and cleaned up. Even when soft his cock was amazing. It hung down like an elephants trunk. So every night after that was playtime. I would get my boobs and pussy attended to and he would get his cock worshiped. He taught me how to kiss it and the suck it. He warned me when he was about to cum. I tried my best to take it in my mouth but there was a lot of it. I liked the taste and swallowed his thick load. He tasted my pussy and I loved it. His tongue drove me wild. I would cum hard and he licked up my juice. He said I tasted so sweet and yummy.
It was October by now and I had turned 14. My brother was 18 and a senior in High School. I was in 8th grade and as I walked down the halls I smiled knowing what I was doing and the fact that nobody had a clue about it or who I was doing it with. My parents were clueless though my mom had asked me about the state of my sheets a couple of times. My brother and I always tried to clean up but I guess sometimes we missed a spot. She didn’t press the issue though and we figured she didn’t suspect anything.
We had become very familiar with each others bodies. I enjoyed our secret affair and loved giving my brother pleasure and of course getting pleasure from him. This had all started a few months ago with him just wanting to feel my boobs. We were in my bed once again and I had his hard cock in my hand. He was kissing me while he played with my nipples. He took his cock out of my hand and began to rub the head across my pussy lips. We had been doing this for a couple of days. It felt really good. He broke our kiss and told me he needed to ask me something. He asked me if I felt weird about doing any of this with my brother. I told him at first I might have felt some guilt but now I loved doing this with my brother. He smiled and said that even though I was his little sister that he loved being with me and always made sure I was comfortable doing any of this. I kissed him ad smiled at that. Then he asked me to do something that made my heart skip. He said he loved me stroking and sucking his cock, but he needed something else. He wanted to try and just put the head of it inside my pussy.
I bit my lower lip thinking about that big thing going in me. I told him I would try it but I wasn’t sure if it would work because of its size. He said all we could do is try and it would make him so happy. I wanted to know that if just the head went in would I still be a virgin? He said yes that as long as my maidenhead wasn’t broken I would be. I had just told him we could try that so I guess I was committed to the idea. I knew of different positions but I wasn’t sure how to go about this. He said that probably the best was was for me to get on top of him and straddle his cock. That way I could go at my own pace and stop if it hurt. He would hold his shaft at the right angle. I looked at it and shook my head and laughed. How on earth was this going in?
I had gotten super wet talking about this. I told him to go check on mom and dad to make sure they were asleep. He got out of bed and opened my door to the hall. He disappeared for a moment and then came back. He said he heard them snoring. He climbed back in bed and onto his back. I climbed on top of him and looked down between my breasts at his hard cock.. I guess the time was now to try this. I got up on my knees as he picked up his heavy fat cock and lined it up. I rocked back a little and felt it touch my pussy. I stopped then to get some courage. He rubbed it back and forth getting the head wet from my juice. He told me it was OK just to go slow.
I could feel the big head right at my entrance. If we actually got that in that was all of his cock that could fit with out tearing me. I held my breath as I pressed down. Here I was just 14 and I was trying to get my 18 yr old brothers cock head in me. The big spongy head started to stretch me. I felt some progress and now there was nothing more that I wanted but to get that thing in me. I had to stop for a minute then press again. I was carefully using my weight to help. He told me I was doing great and there was just a little more to go. My stomach muscles tightened as I pressed one more time. I felt the big ridge move past my tight entrance and it was in. I couldn’t believe it. I had gotten my brothers big cock head inside my pussy. I just held still feeling very full. I could tell it was pressed tightly against my cherry. Technically I was still a virgin.
We both were breathing hard and looking at each other. We were connected now even if it was just the head of his cock in me. He asked me if I loved him and trusted him. I said of course I do. He said he loved me too and didn’t want to hurt me but he wasn’t able to keep from doing this. I wasn’t quite sure what he meant. His hands were on my hips. I was poised above him with just his big cock head inside me. It was pressed up against my cherry. Suddenly I knew what he meant. I was about to say no when he pushed down on my hips. The head of his cock pressed into my maidenhead and it tore. The force of that drove half his shaft up inside me. I opened my mouth but no sound came out.
I was no longer a virgin. I started to cry but not because of that. It was because it really hurt. I was sobbing as he held me close his cock still firmly inserted in me. He said he was sorry, but that he promised it would feel so much better soon. My brother had taken my virginity and I was OK with that. I hoped he was right about the feeling good part but right now it was till stinging. He rolled me over still inside me so he was on top. He started taking slow easy strokes. I gritted my teeth as his cock reached farther inside me. He was trying to be as gentle as he could given the state of my pussy. He said it was super tight and hot in there. I could feel the heat building from the friction between us.
He pushed a little harder and I felt him hit bottom in me. He had reached my end but there was still more cock to go. This was my first fuck and my brother was right, it was feeling better. I was till sore but it was a good soreness. He said he wasn’t going to last much longer. I thought about what that meant and where he was going to cum. Was he going to cum inside my pussy? That was something I had not thought about up to right now. This was my first time and I decided that’s were I wanted it. He was stroking a little faster now and I put my hands on his ass pushing him into me, telling him I wanted it. Without saying a word he drove in deep and hard and I felt his cock erupt inside me. It was like we both lost control. He was cumming in me and I was 14 and not using any protection. I started cumming as well as he finished dumping his load in me.
Slowly my brother withdrew his semi soft cock from my abused pussy. I winced a little as it popped out. I knew my sheets must be a mess but I didn’t care. We held each other close and fell asleep. We were two lovers and also brother and sister. Everything had changed with that act. When I woke up he had gone back to his bed sometime during the night. I stripped my sheets off and got them in the washer before my mom could see them. We had a secret before but now we had the ultimate secret between a brother and a sister. He had taken my virginity. We had sexual intercourse and nothing could change that.
For the next 2 years we fucked all the time. Somehow I didn’t get pregnant even though I was not on the pill and he never used a condom. I had learned about my cycle in health class and I always knew when it was risky. He graduated from high school and went to a technical college. When he graduated from there after 2 years he got a job offer from a company in another state. It was about 200 miles away. We talked about it and I told him he need to accept the offer. It was something he had worked hard for and he needed to try it. I was still in high school and living at home. He could come and visit and I would visit him there. I was going to miss him and the sex but we would still get together. He knew I was right and he moved away.
