Sarah's Diary - Entry 07-09

All parties involved are over 18

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Entry 7: Our First Time

After debating all the possible results that could happen and sharing with my brother all the advice about using protection during our first time having sex we decided we still wanted to go with our original idea of not using it the first time. I was a little worried after hearing all the possible negatives but I'm sure nothing like that will happen to us. So anyway I finally had my first time together with my brother and it was really special, not quite what I was expecting at all with all the horror stories I'd heard from my friends pain wise or blood wise but it was quite amazing. I posted to my Reddit forum, letting them know every step I was taking, getting closer than I ever thought possible to him.

About an hour after our parents left that day I went to wake him up and told him to get cleaned up and ready to which he excitedly did and I asked him to wait in his room and close the door. I showered and changed into my new black lace thong and bra so I could look as sexy as possible for him then I went to my parents bathroom and got my moms bathrobe and put it over me. I put the lube bottle I got on my moms side table then went to his room and went in with the bathrobe and took his hand , leading him to my parents bed where I sat down and slowly took off the robe as slow as I could and tossed it on the floor so I was in just my thong and bra. I was trying my best to try and tease a little now and I asked if he thought I was sexy as I sort of swayed in front of his eyes, letting him enjoy my body.

He responded by tackling me down quickly and kissing me as I started laughing. He said I was the sexiest girl he'd ever met and that made me so happy as his lips kept pressing into mine. His hand went behind my hair , running his fingers through it as I felt his tongue slip into my mouth and I went to return my own. As our lips were locked like that with our tongues massaging each other I moved my hands along his back, scratching lightly against him and pulling him in tight. After pulling away I was looking at him for a few moments in his tight white t shirt and boxers, admiring every faint outline of muscle as my want for him grew before I reached out and pulled his shirt off over his head. He's been going to the gym more recently but he's still mainly just a skinny guy but it did get pretty hot seeing a faint outline of abs and running my hands over his bare muscular back. It wasn't long before he started trying to get my bra off wanting to see my chest but I had to help him with that , undoing my own clasp and then I tugging his boxers off as he slipped my thong down my leg and lifted it off my foot.

I told him to lay down so I could show him how dirty I was as a tease and we rolled over and switched positions so I was sitting on top of his legs and we sat there for a minute, just looking at each almost naked. His chest was moving heavily with each breath and his face was flush, I can only imagine how much I was blushing being on full display right in front of him like that , my breasts were perked up and both my small nipples were hard as ever, I was so excited. I reached a hand up to gently start massaging my boob before I bent down to kiss him and reached down to grab his erection, he was really hard and I wrapped what I could of my fingers around his shaft as I started rubbing gently up and down in his boxers.

After stroking him for a little I slid my body down a bit gathering a bit of saliva in my mouth, tore down his underwear and placed him gently inside so his cockhead was resting on my tongue as I moved it around a bit to try and make him feel good. I started licking up into the crevice underneath his swelling head hearing him moan my name which only made me more turned on. I could tell he'd probably finish soon from his panting short breaths and how swollen he felt in my mouth and him not lasting too long the previous times, but he pulled me off and said to wait because he wanted to make me orgasm before he did as he flipped us over so I was laying on the bed looking up at him as he lowered himself and kissed my neck slowly moving his lips down to my boobs staying there for a while rubbing them in his hands and taking turns switching his lips between each nipple, a little awkwardly but it felt really good so I didn't correct him.

I let a soft moan escape every time he'd suck on one and I'd feel my body tingle and shake. He started going further down kissing along my stomach in small circles then to my legs getting me really excited. He started along he outside of my thighs and working his way in, then started licking just outside my pussy, never near it though no matter how bad I wanted it. To all those who recommended me showing him oral videos on Reddit, thank you so much because his tease was so freaking hot and I was ridiculously horny from it. He went gently further and further in, slow and steady, making me eventually beg for him to lick my clit and with that he touched just over it before slipping his tongue inside my wet lips as he pressed his head forward a bit.

He started to pump in and out like he was fucking me with his tongue as he started to rub my clit. Oh my god it felt so damn good having him in there and as he started feeling around with his tongue I could feel myself getting more and more turned on. I knew I was going to cum as I gripped his hair, but then he pulled his tongue out and sucked on his fingers and started running them across my clit a little too rough at first slightly ruining my buildup. I told him to go a little softer which felt much better as he was caressing it slowly then put his tongue back in.

With this new steady sensation building up and up inside me I came pretty quickly after his motion of rubbing my clit and his tongue exploring my insides for a time and had to grab the sheets as my legs and arms began shaking quite a bit and knew I wanted him inside me, I wanted to go and jump on him, I was so horny but I didn't want him to finish right away as soon as we started like I thought he might so I sat up a bit and started jerking him off just above my breasts looking up at him trying my best attempts at dirty talk , letting him know how much I loved his fat cock emptying it's cum all over my body. I want you to cum all over me, i heard myself weakly shout, a but unsure about how I was talking but he seemed to love it as he let out a moan as his cock swelled thick and dark red as he came pretty quickly, spraying a large amount on my chest and stomach as he started breathing pretty heavily and he actually stayed semi hard.

After several minutes of laying there and enjoying each other , just gazing at the other naked and touching, I was hornier than ever. I asked as sexually as I could if he was ready to try and fuck me or if he wanted a little time to wait. His smile was so genuine and watching his cock grow thick and hard touching my fingers I instinctively licked my lips. It looked so large in my fingers, but I had nothing to compare it to so my uncertainty of whether he'd hurt settled in more. He asked me about the condoms again and we had one more conversation before I eventually just told him it was ok and not to worry about it because I was on a safe day , I decided out first time I would try it bare. I opened the lube bottle on our mom's desk and put a decent amount in my hand and started rubbing along his cock to which he groaned a bit which I thought was super hot as I kept applying it he said it felt really warm and sensitive.

I kept rubbing along slowly and he gradually got hard as a rock again as I layed back on the bed and spread my legs a bit putting a small amount of the lube between my legs and told him to go slow but I was ready. I was expecting a lot of pain or blood the first time I had sex, but neither happened. I had to help guide him in to the right hole and oh wow it was intense at first. There was a slight bit of pressure as he slipped the head inside slowly and I was trying to get used to the size but as he sat there with just his swollen head in it still felt pretty good, like he was slowly pressing me open before he pushed on a bit further and all I felt was a rush of pressure and a heat building as his skin rubbed against mine inside. He was about half in and just sat there as I couldn't help letting some small moans out as I could feel my muscles clamp tightly around him, it was a real full feeling as he just sat there inside of me, I could feel the warmth and firmness of his cock just sitting there like we were connecting. All I could think was my brother's cock is going inside me as I told him to start moving. He slowly started going in more and out a bit, which felt really amazing. He was pushing my walls apart and I was watching the base and good bit of the shaft of his cock come out of me, there was a small amount of white liquid coming from me that was covering him, I think it was just my juices but god it felt good having him fuck me.

His length wasn't too bad but i didn't realize at the time how much he wasn't in, but the width of his cock felt wonderful. It was stretching me quite a bit but with the lube and how wet I was it wasn't a big problem. I put my hands on his stomach to control how quickly he was going so I didn't get overwhelmed and tried to tell him to slow down a few times when he started trying to go a bit faster so I could get used to the depth he was trying to go now. It did feel great letting him lead though and eventually I think he got a bit more confident because he grabbed my hips and started thrusting into me pretty quickly, the smacking wet sound of us together echoing in my parents room was really sexy to me , it was adding to the intense feeling my body had to hear his balls and waist crashing into my body.

The first time seemed to last much longer than it actually did , eventually I felt him get hotter inside me, it was an odd sensation then I felt him pulse in a sort of waves and another warm sensation as he shook a bit like he wasn't controlling his body shaking and he said he was cumming as I felt his cock expand in small bursts , my own walls squeezing around it which felt amazing. I didn't cum from the penetration itself but it did feel really good just having sex and the emotional rush of him cumming inside drove me pretty crazy , it was like he was so into me his body had to give in to his urge and bond with me like he did. He had me really close and I was ready to go again but he said he needed to rest a bit as we turned over into a sort of cuddle, him still inside me and he hugged me from behind so we were laying sideways.

He kissed me on the back and said he loved me and thank you. I held his arm around me tightly and blushed sort of awkwardly. He played with my hair for a bit as we layed there. We lay there for a bit in my parents bed just cuddling and I felt really loved and taken care of even though he was my younger brother, it was a really special feeling. Thinking back on it now if he had angled a bit upwards so he was pressing down more instead of forward his pelvis would have been hitting my clit each time he thrust and I probably would have easily cum so that's something for next time.

We changed the sheets and replaced them, luckily my parents have multiple identical pairs so they won't recognize anything happened this morning and then we headed to school about an hour later. I'm so enthralled with him, but I'm going to be safer from now on and take a test as soon as I can get one just to make sure, but I'm sure nothing happened. I'm wondering now how I can convince my mom to get me birth control because I know my dad never will.

Entry 8: 69?

My brother suggested something later yesterday after school called a 69 position and he seemed pretty excited to try it so despite really wanting to have sex again I went along with what he was saying after he explained to me what it was. The idea itself sounded pretty hot so we headed to my room this time. Knowing we had a decent amount of time alone we jumped in bed pretty quickly. He slipped off the school uniform pants he was wearing and pulled off his shirt and undershirt so he was laying in his boxers. I took off my school uniform and tossed my underwear i had on with it and climbed towards him grabbing his legs playfully and taking his boxers off giving a few playful kisses around his shaft.

I asked him how we should set up and he explained it to me so I turned around so my butt was over his face and leaned forward a little so I could bend down. I bent my neck down a bit and took him partially in my mouth as far as I could get feeling him swell up as I felt my saliva start to cover him. I went to lick around his cock head , letting my saliva coat his shaft as I traced my tongue along his thickness, feeling his veins pulse getting me really into it when I felt his tongue slip into me in a sort of shock, it was an odd sensation having him lick me while I was taking him in my mouth but it felt pretty damn good for a while.

It felt really hot taking him in my mouth while his tongue was exploring me, going further in at a different angle. At a point however it became pretty sore on my neck as it went on, but lucky for me he came pretty soon after, shooting up his load into my mouth as I swallowed some and the rest dripped slowly out of my mouth down onto his cock and waist. He was licking me pretty awkwardly from the backwards position and I had to instruct him several times from the new angle where to go that felt good so I didn't end up cumming from that but was left really turned on so I went to my drawer to get a condom and the lube and put them both on him as he moaned a little while I rubbed him slowly hard again and I went to sit on top of him but time he asked me to turn around and sit up during sex with me on top so he could watch my butt. I gave my best tease asking him how bad he wanted to watch my ass bounce on his cock like that? He answered with a so bad whisper and pulled me over, so I turned around so I was hovering over his dick and my butt was facing him as I lowered myself on to him slowly and got him a good ways in and started grinding slowly back and forth.

I loved this new feeling of his cock spreading me open, even semi-hard as I controlled how deep he went. I have to admit being able to angle him myself and being in control like that was incredibly hot, and looking back at his face while I was grinding against him while I was just feeling the thickness rub against my insides while I started massaging my clit made me cum moderately quickly from how horny I was but not as hard as my previous times from oral. I sat on him for a bit just letting him go slowly deeper in to me , just a little practice stretching me out more, keeping my gaze looking back at him noticing him watching my ass intensely as I kept slowly rocking my hips on him.

Eventually I pulled off and rubbed him a little with my fingers. I watched his sensitve cock grow and throb until he was still semi-hard again as he told me how sexy I was and couldn't wait for a second date at the next city over so no one would recognize us. A few moments later a sex scene came on the tv that was on in the background to cover our noise just in case. I just giggled a bit but he asked me if I'd ever watched porn while my fingers kept stroking his cock back to hard. I honestly answered yes and we started having a conversation about what we had seen, what we liked and didn't like but ultimately lead to him asking me something.

He said I had always looked extremely sexy in my glasses asked me if he could cum on my face while I was wearing them. I thought this was a bit odd because I didn't feel hot or even pretty in my glasses, it's why I originally got my contacts even though I didn't like that look either but I was feeling really playful so I agreed on the condition I got to pick the next thing he had to do for me. I told him id go get ready letting go of his cock and quickly hopped up and took my contacts out and put on my glasses and headed back towards him, it felt liberating to walk around the house naked without our parents here.

As I made my way back to him, I slipped my hand down his chest on the bed to his stomach to rub my fingers around his rapidly re-hardening cock and got down on my knees on top of a pillow I put down because of my hardwood floor. I took the condom off letting the cum leak down on him and he guided his dick to the edge of my lips and pressed against them. I opened slowly, taking in just a bit then as much as I could and started bobbing my head back and forth very slowly as he started groaning slightly. His hands reached out to grab some curls of my hair and hold my head still starting to push a little more into my mouth.

In the heat of the moment I decided to try something I'd heard my best friend talk about doing for her boy toys and slipped him out of my mouth and put a little lube on my hands rubbing it in before I placed both hands around what I could of his cock's shaft and started twisting them gently in opposite directions and jerking up and down, stopping just below his head. I asked him if it felt alright and he responded with a groan and started bucking his hips so I assumed it was a yes and kept twisting then licked the head of his cock gently in quick motions, letting my tongue tease the small crevice below his cockhead. He exclaimed he was going to cum so I let go as he asked me to and let him finish rubbing himself above my face.

His orgasm was hard and only three of his strands hit my glasses the rest shot in my hair and cheeks but enough got on them I couldn't see and he was saying thank you and how sexy that felt and how hot I looked with his cum on me. He begged me to keep a picture of me covered like that , which maybe I shouldn't have let him, but I was helpless at that point and let him get one. After he pulled me up and asked me to sit with him, we laid in my bed or a while after that just cuddling and being together and listening to music while I was thinking of what I would like in return. I thought about the 69 we had tried and decided I'd probably like it better if I didn't have to focus on him so much so I explained to him that I wanted him to eat me out until I came and he laid face up on my bed ready for me to get on him. I started trying to flirt with him with the best dirty talk I could think of.

He had asked me to try more vocal stuff because he liked it, so I said he was going to have to make his big sister orgasm all over his face and have his tongue deep inside me or I wouldn't get up and sat on his chest , facing away from him , moving my ass towards him as I was kissing along his legs leaning forward then moving my pussy slowly up towards him and moving so my butt was over his face and sat down a bit instructing him to use whatever he wanted. He didn't take long to react and reached one hand out to gently massage my hips and pull open my butt a little , which felt really good then he pressed his tongue gently to my pussy lips and ran it across the outside, softly letting a long lick go from the bottom to the top and repeating causing a shudder to go through me.

He teased me for a little running his mouth gently along the outside as I grabbed his legs and held them down and sat a little lower to his mouth as he slipped his tongue inside at a sort of upward angle making it more solid. It felt really good as I could focus on relaxing and what he was doing to me, after a bit of darting his tongue inside he found a spot that I told him felt really good and to keep going around there. That continued for a bit until he reached his other hand up to massage my clit gently like I asked him to before the past few times and he was much better at it this time but still got a little rough when he pinched it slightly.