Note: This story was dynamically reformatted for online reading convenience. ï>¿Dear Diary byDUCKLYNNÂ(C) Dear Diary: Mom's Boss Dear Diary, I know I don't need to tell you again how mad I was mom took me with on her business trip over my birthday weekend. I may not totally hate the trip anymore, but mom is on my shit list. She claimed it was because she did not want to miss my 18th birthday but I don't believe her as she was nowhere to be found after breakfast when one of her co-workers came to collect her for a meeting. I went to the pool. I was the only person there, no surprise as it was 10am on a Thursday. Thankfully mom wasn't with me or I would have had to listen to her bitch about my swimwear. Oh I did get that bikini I wrote about before, the bright pink one that was almost a string bikini except it didn't tie around my chest or neck, and I may have got the top a size or two small so my tits were almost spilling out of it. The bottoms were the high cut ones almost a thong but a teeny bit more coverage. I was laying on a lounge chair, listening to music on my phone, when a guy probably in his late 40s chose to sit beside me. I know it is probably bad of me but I decided to tease him. I arched my back a bit like I was stretching, knowing my breasts were already pumped up by the small cups. Slowly I lowered my leg nearest him to the side of the chair and sat up. I made sure my legs were spread enough he could see the tight fabric caressing my pussy. Standing I went over to the stairs into the pool. After making a quick lap I floated on my back where I knew he could see me. The guy quickly got up and left the pool area. I laughed out loud when he was out of sight. From one of the pool side terraces I heard a deep voice chide me about teasing horny old men. I swam to the side of the pool the voice came from to see who it was. My jaw just about hit the floor, it was mom's boss. He was standing just inside his room, in black boxer briefs, the sliding glass door open. I asked him how he knew I was teasing horny old men. I watched as he reached down and ran his hand over his boxer clad cock. I know, Diary, I have told you before mom's boss was hot, but seeing him in just his underwear stroking himself was amazing. I knew he had muscles from seeing him in a t-shirt that one time but holy hell, he had more than a 6 pack and those super hot stomach muscles pointing towards his cock, yummy. If I had to guess he is probably in his late 30s but so fucking hot. I climbed out of the pool, without drying off at all, I walked to his terrace. I asked him if it was wrong to tease a girl on her 18th birthday. He growled "legal" as he grabbed my shoulders pulling me against him into his room. His hand moved down my back to my ass. He pulled me tight against his cock, and damn did it feel big and hard. One hand left my ass pulling my hair making my head arch back. He practically attacked my neck but fuck did it feel good. As he sucked on my neck I knew he was going to mark me but I really didn't care. I moaned a bit. His hand on my ass moved to pull on my bottoms. I stepped back and asked him if we should be doing this. He slapped me across the face, but not hard, more in a way to let me know who was in charge and it was not me. Grabbing my hair once more he pulled me to the bed. With a shove I landed on my back. He wasted no time grabbing my bottoms and pulling the wet fabric from my body. They made an odd plopping sound as they landed on the floor. He crawled up onto the bed forcing my legs apart. Rubbing his cock against my pussy. Only a layer of fabric from his boxers separated us. I am so happy I decided to shave my down there, he was able to slide smoothly up and down as he bucked against me. He pulled one of the cups of the bikini top to the side. He squeezed my breast hard, but it felt so good. As he lowered his head and bit my nipple I cried out in pleasure. He covered my mouth with his other hand. I could feel my pussy getting wetter and wetter, he was still rubbing his covered cock against me and had started sucking on my nipple. I don't know why I did it but I grabbed the headboard holding the bars leaving my body exposed to him. The other bikini cup was ripped, literally, from over my breast. He moved to start nipping and sucking that one and was squeezing the other. I felt my back arc as I started to cum against his boxers. "Yes cum like the dirty whore I know you want to be." As he said those words a second wave of pleasure rippled through me. He stood up and looked down on me, hand still on the headboard, tits exposed from my bikini top, knees bent, legs spread showing my wet pussy. Moving backwards he shut and locked the terrace door, but left the curtains open. As he came back to the bed he pushed his boxers off. His cock was huge, like the cock on the guys in porn. I could not take my eyes off it. "Are you a virgin?" I nodded and I think his cock grew even bigger. He moved about the room. Coming back to the bed he used a couple of ties and secured my hands to the headboard where I was still holding on. He used another as a sort of blindfold. I felt his fingers run over my pussy spreading the wetness around my skin. Then he slid his fingers deeper circling my clit. I gasped. "Yes my innocent slut, let me hear those sounds now that no one else can hear you." His words turned me on more, I must have got wetter he laughed and slid his fingers into my slit. He started fucking my pussy with his fingers, I think two fingers. He was moving fast, it felt so good. I could not stop myself from moaning and begging for more. The sensation just kept getting better and better until suddenly I came. My whole body was shaking from the orgasm. "Oh my god, you are a squirter. I think I want to see that again." I didn't really know what he meant by squirter but if he was going to make me feel that good again I was all for it. He started caressing my body again nuzzling my breasts as he stroked my pussy. It did not take much until I was rocking my hips wanting his fingers inside me again. He did not disappoint me either. He started fingering me hard. He was pushing his fingers deep then pulling them out over and over. The sound of my wet pussy filling the room. He stopped going in and out, with his fingers deep in me he started moving them rubbing something deep inside me. I don't know how he could move his fingers so fast but fuck yes it felt good. I think I screamed his name as I came again. I must have blacked out a bit because next thing I know the blindfold is off and arms are no longer restrained. The bed below me feels cold. "Did my little slut like covering the bed in her cum?" I nodded because I could not form words. "Does she want my cock inside her stretching her, wrecking her pussy?" I moaned. My legs falling apart without thinking about it. "Spread those legs wider. Show me that soaked pussy." He moved so fast to kneel between my legs. His cock standing hard against his stomach, a drop of liquid on the tip. Grabbing his cock with one fist he lined up on my pussy. I think I cried out as he broke through my hymen, driving his cock deep inside me. He started pounding into me. At first it hurt but then he reached down and rubbed my clit as he fucked me. I grabbed his shoulders pulling him closer to me as I wrapped my legs around his hips. He stopped playing with my clit and grabbed my tits as he helped me to sit up. I was riding his cock now. I got control. I moved slow, up and down, letting him go so deep inside me. He was pinching my nipples hard as I rolled my hips as his cock was firmly buried in my pussy. Letting go of my tits with a growl he grabbed my hips and started slamming into me again. I clung to him as he fucked my pussy hard. I heard him grunt a couple times as he bottomed out inside me, and then a hot warmth spread inside my pussy. It felt so good I came hard my pussy clenching against his cock, holding it deep in me. He collapsed on top of me on the bed. We both must have dozed a bit. We were woke up by his phone ringing. I could hear him talking to someone on the phone, something about a killer migrain to have my mom go to the meeting and take notes for him. I could feel something sticky between my legs. I ran my finger over my slit. "Are you on birth control?" At his words I realized the stickiness was his cum. Still playing in his cum I told him no. "Good I am going to fuck a baby into that pussy." We fucked the rest of the afternoon. He came in my pussy 4 more times. I can't wait to find out if he did fuck baby into me. I both want it and don't. If I do I would always have a piece of him near me. If I don't then maybe he will keep trying. Dear Diary: Detention Dear Diary, I was late for 5th period after lunch and Mrs. Brown gave me detention. Tomorrow I have to spend time after school with whichever teacher could not figure away out of supervising detention. I hate being considered an adult in the eyes of the law but still being a child to school and to my parents. I have been 18 for almost 8 months, let me grow up. Well I have a date with Jimmy tonight, maybe I will let him finger me again as I give him a hand job. Tootels Dear Diary, I went over to Jimmy's like we planned. His older brother (hot as fuck) answered the door. Apparently Jimmy left with skanky Sara and told his brother to tell me it was over because I would not fuck him. Well he can get crabs from skanky Sara. Goodnight. Dear Diary, You remember me mentioning Jimmy's brother. Turns out he is the newest baseball coach, and on days the team has later practice he is on detention duty. He was sitting at the front desk reading a novel. His black henley looked like it was sewn on him. The long sleeves molded to his arms and showed off his muscular chest. As he reads, a lock of dirty blonde hair falls forward onto his forehead. When the time for detention starts I am the only one in the room. "Georgina?" He asked in his smooth tenor. I told him to call me Gina. I asked if I could call him Aaron, since he had already broke-up with me. He chuckled and said I could. He went back to his book. I kept looking at him, imagining his strong fingers gripping my breasts and sliding down to my pussy. I would tread my fingers through his hair. We would kiss. I could feel my panties getting wet. I started to shift around in my seat. Aaron looked up and asked if I was ok. Deciding to be bold, something I never was, I told him I was not ok. I stood up and moved to his desk. I sat on the corner beside him. As he watched me I told him, last night his brother was supposed to make me cum, and ditched me, and now I am turned on and just want to feel something hard inside my pussy. Aaron licked his lip and asked how old I was. I told him I was 18. He reached over and flipped my skirt up so he could see my wet panties. "Have you fucked before?" I told him the truth once before and not his brother. Aaron had me unbutton my shirt. I also unclasped my bra since it was a front clasp. I know my breasts are not big but I like them. He pulled me in front of him and spread my legs so he could slide between them. Aaron started sucking my nipple and squeezing the other. It felt so good. With his free hand he pulled my panties to the side and ran his finger through my pussy lips. I could feel how wet I was as his finger glided through my folds and slid into my slit. He pushed it deep inside me. I was moaning as he fingered me. Abruptly he stopped fingering me and playing with my breasts. Standing he shoved his black dress pants and underwear down. Holding my panties to the side still he rammed his cock deep inside me. I had never felt anything so big in me. As I grabbed for his shoulders he pushed me flat on the desk. Aaron started pounding into me. My tits jiggling with each thrust. Aaron's hand covered my mouth, I didn't realize I was moaning until then. It felt so good. His cock was going so deep inside me. I hooked my legs on his hips. With a hard thrust I felt him come inside me. I was so close. I think he knew I hadn't found release yet and kept thrusting and used his free hand to rub my clit. The extra stimulation sent me over the edge. I screamed into his hand as I reached my orgasm. As I sat up I could feel his sperm on my thighs. "You on birth control?" I told him no. He sat back in his chair and pulled me onto his lap. I could feel his cock getting hard again. "Good" was all he said as he started rocking his semi against my pussy, wet with both our juices. Aaron started sucking on my neck and playing with my breasts. Was pinching and pulling my nipples, I never liked that until now. I felt his cock head push against my clit. I rocked harder against it loving the stimulation. I was about to cum when Aaron stopped me. Holding my hips he told me to stand up and turn around. He lowered me so I was on his cock, my back to his chest, my legs spread over his. He went in so deep. Aaron started thrusting his hips up slamming his cock into me. I could not believe how good it felt. I bit my lip to keep from crying out as he started rubbing my clit too. My body was shaking as I reached the peak. I felt that warm rush of him coming in me again. We sat like that a few minutes then Aaron started buttoning my shirt, and told me detention was over. But he didn't think I learned my lesson and would need me in detention again on Thursday. I am looking forward to detention now. Dear Diary: Chat Dear Diary, It's been a while since I wrote to you. So much has happened recently. So I finally worked up the courage to meet Stan. I have never physically met anyone from the internet before, and Stan is older than me, but I figured if I was going to meet anyone it would be him. We decided to meet at a local mom and pop diner. I was about 10 min early like normal, Stan was already there with a bouquet of daisies. He looked just like the photo he sent me. Dark hair starting to go silver at the temples, light grey eyes, tall, not chisled but not fat either, just nice. I walked to the booth and asked if the seat was taken. As he looked at me, he smiled and told me to sit. I know I am not your skinny mini barbie doll model type, I am more of the BBW type gal, but you already knew that. Stan's eyes kept bouncing from my face to my tits and back again. We talked for a couple hours, then Stan asked if I wanted to see his home. We went to his car, a super comfy SUV, and Stan drove us to his house. It was a nice house in a quiet neighborhood, a family type neighborhood. Well, on the drive Stan had let his hand meander up higher and higher on my leg until his fingers slipped under the hem of my skirt. He caressed my pussy through my panties as he drove. As we got to his house he pulled into his garage. He told me to wait, he would get my door. He came around the car, I could see he was hard through his pants. Opening my door he extended a hand to help me from the SUV. We did not make it far, as we got to the front of his car he backed me against the side of the hood, and started kissing me. If felt so good our tongues mingling and caressing as he pulled my skirt up to my waist. While we continued to kiss he grabbed my ass and lifted me onto the hood. I felt my leg getting caressed, then raised to pin it over his arm as he braced his hand behind me. Stan's other hand started pulling at my shirt. Without thought to where we were, I pulled my shirt over my head. I heard Stan growl as he pulled my bra cup to the side. He flicked my nipple a couple times then leaned in and bit the nub. It felt so good I could not have stopped my moans if I tried. As Stan sucked and licked my breasts (somehow my bra disappeared without me realizing it) his hand now unoccupied moved to my pussy. He moved the fabric of my panties to the side and slid his fingers straight inside me. He used his thumb to rub my clit as two fingers curled inside me fast. He was so good. I could feel him hitting what had to be my g-spot over and over again. I felt myself reach climax so much faster than I could make myself. When I finished orgasming I found myself clinging to Stan' shoulders, his fingers still idly rubbing my pussy softly. I looked up at Stan before I could say anything he hiked my leg over his arm higher and slammed his cock into me. I screamed as he filled my pussy. His cock was so much bigger than I had ever felt before. Not only was his cock thick but it was long too. His cock was stretching me as wide as I could go. Stan was pistoning in and out of me. With a soft thud I fell back on the hood. It felt so good having his big cock moving inside me. I could feel my tits bouncing on my chest. I swear they almost hit me in the face he was pounding me so hard. I cried out as I orgasmed. Stan grunted then slammed his cock deep inside me and held it there as he came inside me. As Stan braced himself above me we heard the rumble of a delivery truck going by, we had forgotten the garage door was open! Laughing we grabbed as much of our clothing as possible and headed to the house. Well Diary, I won't go into detail but we did make it into his house. We went straight to the bedroom and fucked again. Then slept a few hours and fucked some more. Xoxo Diary. Dear Diary, It is about 6 weeks since I met up with Stan. He won't respond to my messages and blocked my number. I went by his house only to learn it is an AIRBNB you can rent the full house.. The worst part, I am about 3 weeks late. Dear Diary: Honky Tonk Dear Diary, I think I may be a slut, and I like it. I went out on Friday night with Marcia and Olivia to the new bar. It was full so we ended up at some dive of a honky tonk. The beer was cheap and there were a lot of hot guys. I was standing by a table with the girls when a few cowboy looking guys approached. The one beside me started pulling my skirt up in the front. I don't know why I let him other than I was a bit scared and a few more bits turned on. He fingered me right there standing at the table. I think the other guys knew, as I was getting close, the two guys took Mar and Liv to the dance floor. Nothing more happened that night. Saturday I wanted to go back, hoping my cowboy would be there. Liv and Mar didn't want to go out. So I went by myself. I decided to forget to wear panties under my skirt this time and paired the short skirt with a crop top. I finished the look with high red heels. As I entered the bar I heard my name called. There was my cowboy with a few different friends at a table by the pool tables. I went over and joined them. The beer was flowing freely. I mentioned I had never played pool before. The guys offered to teach me. One of them showed me how to stand with the stick thingy. As he had his arms around me showing me I could feel his hard cock against my ass. The guys rotated showing me how to shoot different shots and grinding their cocks against my ass. As I leaned in to take my shot someone slapped my ass causing my ball to go askew and sink the black ball. "Do you know what happens when you sink the 8 ball?" I was asked. I asked if that meant I lost. "No it means we all win." My skirt was flipped up showing my bare ass to everyone. I heard a moan from behind me. Looking back it was the cowboy from last night, with his cock out. I only had seconds before he slammed deep inside me. It was a good thing I had got just as turned on by the cocks grinding against my ass. As he was fucking me, another guy was climbing onto the table before me to suck his cock. Someone else guided my hand to their cock, I started jerking him. It was surreal having a cock in my pussy, mouth and hand. Cowboy pulled out and told me to climb on the guy before me, who had moved to his back. As I lowered myself on his cock I felt a hand pushing my chest down. Then suddenly he was sliding his cock head on my ass, the tip slid in. Before I could do anything Cowboy was fucking hard making me fuck the guy below me. I glanced up and saw guys in the main area of the bar watching us. Seeing me looking some came over and joined the guys. Before long I was held spread eagle on the table. I was sucking one guy, being fucked, having my tits played with and giving hand jobs all at the same time. I felt someone cum inside me. As he finished, he asked if I was on birth control. When I said no he started to harden in me again. It didn't take him as long to cum the second time. Another guy took his place, rubbing my clit as he pounded my pussy. I screamed as I came. I felt someone lift me and start fucking my pussy from below me. Suddenly he held still and a second cock was pushed into my pussy. I rocked my hips stimulating both cocks. I could not believe how stretched I was. It was so amazing. I have ever felt anything like it. The two cocks stretched me to the point it hurt a little, but in the best way possible. Both guys came inside me almost at the same time. One of the guys sucking my tits went down to take up the spot at my newly vacated pussy, and fucked me hard and fast, making me cum so much I am sure the pool table was wet. I don't know how many guys fucked me, made me suck them, got jacked off, or just played with my body over the following 2 hours until last call was called. By the time the night was over I must have had dozens of loads of cum filling my pussy. The bartender promised me free drinks for life after I let him cum inside me. I was invited back next Saturday for lesson two on stick handling. I can't wait.