Sarah's Diary - Entry 04-06

All parties involved in this story are 18 or over.

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Entry 4: First Orgasm

Thanks to all of the good suggestions and some amazing advice I decided to talk to him again the following morning. I let him know I was thinking about him potentially romantically and wanted to see if he felt the same as opposed to a pure physical attraction. He told me he definitely thought of me in a girlfriend type of way and he probably always would because of the fact we are best friends as well. We talked for a little about helping him to last longer than he did before and I let him know I wanted him to see me, but I was still not that self confident in my body.

He reassured me I was one of the sexiest girls he knew which made me really happy as I pulled him into my room and sat down in my bed. His eyes were staring at my top, it wasn't anything special just a white tank top with a normal light blue bra underneath. I took a deep breath and lifted my shirt over my head so I was just in the bra and my tummy was exposed. He reached out to touch me but stopped short and asked if he could feel my boobs. I said sure and he started rubbing along the cloth material. I'm not very endowed chest wise, a b cup, but he didn't seem to mind as he grabbed one and squeezed lightly.

The touch itself was an ok feeling but just the thought of him touching me like this was making me really wet, I'd been turned on before but this was one of the more intense times. I could feel my nipples getting harder as he kept going and he asked if I could take my bra off. It didn't take long for me to reach back and undo the clasp letting it fall on to my bed as I was on display. I instinctively moved my arms to cover myself, but managed to fight the urge and pulled them away, I wanted him to see.

My boobs aren't perfect, pretty small and the same pale color as the rest of my body aside from my nipples which are a bright pink shade with medium sized areolas around them. My nipples were standing straight up at this point as his hand went back to rubbing me, he was a bit rough and I had to guide him on how I liked to touch myself there but he eventually got it, lightly massaging my chest. After a little he started to lightly brush his finger tips across my nipples and I've always been pretty sensitive there so I couldn't help but let a soft moan escape my lips.

It must have triggered something in him because he leaned closer towards me and took my left nipple in his lips and starting playing with it on his tongue. It felt really good and my hand reached to brush my fingers through his hair. I loved the attention he was giving me and he did accidentally get his teeth caught a few times but I helped him get back to being careful each time. My body started getting hot as I got more into it and I wanted him to touch me more. I asked him to touch me and he started rubbing his free hand along my legs and my bare stomach. His fingers brushing along my tummy made me shake a little, it was so hot to feel him trace along my skin like that.

He asked if he could see me down there after pulling back a little and gesturing towards between my legs. My cheeks were definitely red at this point but I wanted him to see me completely. I undid the string on my sweatpants so they were loose and let him tug them off so I was sitting in just my underwear. I've never had any sexy undergarments but he didn't seem disappointed at all with what I was wearing , plus he didn't keep them on long before he pulled them down to see. I was trying pretty hard not to cover myself with my hand out of instinct but that went away when he lightly rubbed a finger across my pussy lips without much warning.

I was already wet and feeling him glide along like that made me shudder and his eyes were glued between my legs. I've never thought I looked amazing down there and I've looked at it quite a few times but it's also behind a rather thick amount of hair. He kept brushing along the lips , his mouth was wide open like he was in awe and I had to close my eyes in focus a couple times to stop from moaning too loudly. It felt good, really good, just thinking about him touching me like this was a huge turn on and the act itself was amazing. It was so hot, and so wet, I wondered what he'd think of me because I was definitely covering the tip of his finger in my juices from down there.

I asked him to try and rub my clit as I moved his finger towards my swollen bud so he'd understand and he was a little too hard at first and it wasn't very comfortable but after I told him to go a little softer and it felt wonderful. I'd touched my clit before but never like this and oh my god it was driving me crazy how good it felt. I had to grab the sides of my bed and grip the mattress to keep myself sitting up. He kept at it and he said his arm was getting a little tired but it felt so great and I could feel a buildup that made it feel like I was going to burst so I told him to please keep trying and after a few more minutes I felt something amazing.

It was unlike when I touched myself a little during masturbation, that was always a good feeling but this was bliss. I could feel my body shaking as it felt warm and a tingling sensation of pleasure was coarsing through my skin. His touches were making me shake and my clit was so sensitive I had to ask him to stop for a minute. A few more shakes came through and my legs were shaking so hard I hit him in the face with my knee by accident.

His eyes were looking up into mine like he'd done something wrong but I assured him that it just felt so good, it was the best feeling I've ever had and I wanted him to do it again, it was only an accident. It was hard to breathe right and every breath felt heavy and hot, I was sweating a little and I didn't even want to go to school at that point, just have him do that again. I'm pretty sure he gave me my first real orgasm and oh what an amazing feeling.

We didn't have much time left after that before class was going to start but we did talk about a few things. We talked about preferences and what we liked in each other, I asked him about making sure to watch his fingers around my clitoris because it was really sensitive and if he was going to try oral to be careful of his teeth, I told him I'd try the same for doing it to him and I asked him to tell me what felt good with my mouth. We both agreed we'd rather shave our pubic areas to see what that's like because it's something we'd prefer and I asked if he'd look into lasting longer and oral sex because I wanted him to try it on me and I agreed to look up more blowjob advice so I could make him feel as good as I can.

He said he'd do both and he told me he definitely liked around his cock's head being touched so to do more with my tongue there but not so much because he doesn't want to finish so quickly. He's also taking me to a movie tonight, as far as our parents know we are just going like normal but it's going to be our first official date. I'm really excited about it and that we both feel the same way, I'm so happy I've heard from couples who started like we are that are still happy together and I feel like I want to dress nice for him, the only issue being I don't really have any sexy clothing or outfits but I'm going to see if I can convince my mom to come with me to get some underwear that I can feel sexier in.

I've always wanted to try the lace and the thongs on that I've seen because I've read it helps to feel like a sexier girl when you dress in something like that, plus I think he'd really like me in something like that. I've never felt like this about anyone and I really think we are enjoying something special so definitely thank you all for the advice on learning. We are having a great time so far and I can't wait for tonight. Every time I typed an update into the support forum for couples like us I felt like we were getting closer to becoming a real couple, and for the most part the resounding support was wonderful.

Entry 5: Movie Night

"Definitely a special thanks for the tips , I took a lot of them to heart like having him look into how to do oral on me and looking up more blowjob videos to help me, and especially about not wearing panties to the movies , it was a really sexy tease advice I'm glad I know how to do now. " I posted my response to all the advice I'd been given before sharing. Anyway, last night started out on a wonderful note, I managed to convince my mom to get me a couple of sexier things to wear after we got home in the afternoon but she said I had to promise not to let my dad know.

I know she has some too in her closest but whatever so I just shrugged about it, but promised. She got me some panties that are pretty revealing and a pretty lace bra and another matching set of a yellow bra and thong. I've always liked yellow and I was really glad she let me get something like that before we went back home and I put them away. I wasn't sure what I was going to wear yet so I tried on outfits for a little wanting something that would look nice for him but still be comfortable.

Unfortunately it started raining pretty hard before our date so I went with my comfort outfit, a sweatshirt and sweatpants, I definitely wasn't anything special to look at but I knew I could make it up to him later. I debated wearing my new underwear but decided not to wear any at all and try a suggestion I'd received for how to be seductive. I talked to my mom a bit about going out tonight and Mother's Day since they were close together. She told me our dad was taking her out all night tonight because he wouldn't be around tomorrow much. I had to stop myself from jumping for joy, we had hours with just me and him tonight and I was not able to contain my excitement long.

She said they were heading out pretty late and we were going to a pretty early movie so I figured we'd probably be back in time to have fun with more of our experimenting. She gave me money for an uber and dinner and told us to have fun as we headed out. I whispered to my brother in the backseat about the good news tonight and he started beaming. We talked for a little outside the theatre and decided not to do anything too suspicious until we were inside incase we saw anyone we knew before we went inside and grabbed some snacks and headed in.

We sat in the very back and the theatre was almost completely empty aside a couple of older ladies pretty far below us so I decided I wanted to try and tease him a little. I was half watching the movie anyway because I couldn't stop thinking about later tonight being alone in the house. I wanted to do something but It was getting pretty close to being over and I was fighting my nerves to try something as I was fidgeting in my seat a little feeling pretty wet while rubbing against my sweatpants before I finally leaned close to his ear and nervously whispered I wasn't wearing any underwear.

He looked a bit sheepish at first and I tried to give him more of a hint opening my legs apart a little and rocking my hips slightly forward. I was so turned on and I just wanted him to touch me a little bit. He reached his hand between my thighs and slowly inched it up to rub the outline of my lips though the cloth before he lifted the top of my pants and slipped down inside. He kept sliding his finger through them and they were so wet it helped him slide back and forth causing me to lean into him and whimper quietly as I could.

I loved the way he was slowly letting his finger just move up and down between my lips but not pushing inside but I wanted him to try a little. I put my lips close to his ear and whispered I wanted him to put it inside, he didn't wait before pushing it deep in, something I wasn't really ready for as I let out a soft moan, feeling myself close around him as he pushed in and out I hugged him towards me, oh my god I wanted him so bad. I told him I wanted to have sex, I wanted to know what it felt like but I'm not quite ready yet and he said he definitely wanted to as well and he'd wanted to have sex with me for a while but he'd wait until I was ready, so we both agreed to wait a little.

My light grey pants had a small damp spot on them now between the legs I could see as the movie ended and the lights came back on as I pulled his hand out quickly. We got up to head over to a nearby Italian place next to our theatre, trying to make sure our parents would be gone when we got back. As we waited for food and I made sure no one we know was there I told him I wanted him to try oral on me, I'd been interested in it a lot and wanted him to try it on me tonight. He looked really happy and I knew tonight would be a good time after he said he'd looked up a lot about it. After dinner we couldn't wait to get out of there, we got another uber to head back home and rushed inside. We had a great time even for something so small as our first real date and it was only getting better.

I wanted to surprise him with my new underwear mom let me get, but knew I wasn't quite prepared for sex yet so I decided the next best things would have to do, I wanted him to give me oral and last through a blowjob. Our parents were still there when we got back so I shaved clean for the first time. It wasn't painful like I thought it could be and I was making sure everything looked ok. I never thought I had a sexy pussy but I liked the look better now as I fixated on it freshly shaven and it looked kind of cute. I've always wanted to have the bigger lips that I think guys find sexy but mines just a slight slit that looks much like the rest of my skin with very tiny light pink lips inside. I'd never explored myself much and I was getting curious about what I looked like in more intimate detail. I'd always thought it looked too young but I'm ok with it now , I got ready and showered because I wanted to make sure I tasted ok for him to lick me the first time and as soon as our parents left to go out to their dinner I slipped on my new yellow lace bra and thong set then went to my room and laid a bit sexy on the bed and called my brother in.

He came in and started to ask me something then stopped and stared at me in my underwear, I loved the look he was giving like his eyes couldn't leave and his mouth wouldn't quite close so I gently slid over and pulled him into the bed and asked him if he liked what he saw. I felt so sexy and naughty as I took him closer but he was wearing basketball shorts so I could tell he did by the large bump pressing out of them, I sat up on the bed and asked him to take his clothes off so I could see him and he slipped his shirt off and pulled his pants and underwear down really quick.

I loved his body, so thin but faintly muscled, and tall and strong, I probably stared for a little while at his hard on, he shaved just like he said he would and it made it look bigger even though it was the same it's always been since I've seen it, but seeing him standing there at the edge of my bed got me super excited so I rolled onto my stomach and had him stand at the foot of the bed and slowly put it in my mouth , licking around and behind his cockhead lightly and not too rough because now I know he loves that and one hand rubbed his now smooth balls and the other pulled him towards me a bit by grabbing his butt gently.

It felt so heavy holding him and full as I let a hand rub up and down along the shaft as I could feel him thickening in my fingers, I love how hot he felt, so warm and harder and harder. I looked up at him as I moved my tongue around the head of his cock while my legs kicking up behind me out of excitement. I kept my gaze looking up at him, I loved seeing his eyes staring into my own while his mouth was open wide breathing hard and I could feel him pulsing in my mouth. I kept going like that until he let me know he was going to cum which he's definitely getting better at telling me now and lasted a little longer as I slipped him out and jerked him really quickly just over my mouth and he exploded quite a bit like last time across my lips and some shot across to my forehead.

I smiled beaming at him and how excited he looked then he took me really quick in his strong grip, flipped me onto my back so my body was face up torwards him now giggling with excitement, my gaze looking down at my body and up to him excited as my legs hung over the edge of the bed and he slowly slipped off my thong and he tried taking off the bra but he couldn't really figure it out so I helped him out and tossed it on the floor.

His eyes were fixated between my legs and he kept looking up towards my chest before he moved his body up and started kissing down my neck to my breasts then my stomach and eventually my inner thighs, he was getting really good at teasing me as he kept kissing around but not quite touching my pussy. Eventually he let me have what I needed and slipped his tongue in and slowly massaged the inside of my lips. I couldn't help but let a moan come out, it felt amazing feeling him taste me like that, it was so warm and strong , eventually he pushed it deep inside and licked up and down. His hands reached up to start rubbing my nipples as I let another small series of whimpers escape.

It felt really good and I could feel my body getting hotter with each press of his tongue inside me. He pulled away a little and he licked his fingers and gently rubbed them over my clit that was so hard and throbbing at his touch I couldn't believe I didn't burst. He was much better at the amount of pressure to use. He kept his finger rubbing my clit as his tongue went back inside me and at this he pulled up and started whispering in my ear how he couldn't wait to fuck me and take me when our parents were gone before putting his tongue back inside and that tiny whisper and the thought of taking his cock inside me pushed me over the edge and I came hard enough the muscle spasms made my legs squeeze his face by before he grabbed my shaking legs.

He sat and watched me for a bit coming down from my orgasm , his tongue still writhing inside me and then tracing his finger from my soaking lips along my stomach making me shake again up to my lips making me taste myself then kissed me for a long time on the lips and said he really loved me and his surprise of my underwear then we decided to call it a night to be safe. I'm so happy it went well, and he's only getting better each time which is amazing. I can't help but get soaking wet thinking about him now late at night.

Cumming on his tongue felt so good , I felt so naughty and hot and I want to fuck him so bad now. I've looked into getting condoms but I've also read if you have sex close to your period there is a very low chance of getting pregnant so I'm thinking of maybe just being how it should be the first time, but is this really risky? I just want to feel it how it was meant to feel once and I don't think anything bad could happen after one time. Would it still feel as good for him with a condom? I asked my forum for advice and let my thoughts drift off to him.

Entry 6: Sleeping Sound

Just a quick little update to share about last night after our time together and this morning before church. Well after having fallen asleep about an hour after the date I woke to my brother coming in to my room at around 2 am and shaking me a few times, one eventually woke me for good up but I pretended it didn't briefly, curious to see what he'd do and just rolled so I was face up towards him. I told him before in our talks it was ok to come in my room and tease me as long as our parents weren't there and I was getting to experience it firsthand now.

He said my name a couple times and then moved my t shirt I wear to bed up past my chest and started rubbing my boobs softly for a little and started kissing around my stomach slowly, whispering my name every few kisses or so until he kissed his way down to just above my thighs and pulled my underwear down a bit and stuck his tongue in a little making me laugh and I sat up a bit , him backing up a little surprised as I said something like don't stop now, you're on fire and he smiled and went back down , his hands sliding gently across my stomach and holding my hips tightly while massaging them a bit as his tongue found its way up to my clit that he quickly wrapped his mouth around and started sucking lightly.