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Alison Pill in Dear Wendy 2005

That shirt grab though 😍 paisleeeeee

I was about 21 when this happened, I know it’ll sound completely unreal and if I hadn’t been there myself I would’ve said the same thing… So i has just gotten out of a long and honestly rocky relationship. After several months of getting my shit together and healing myself up some I jumped out there on the dating wagon. I was not looking for a serious relationship then, just some great fucks. I’d sit down at the Starbucks and other small shops to have a frappe (fruity ones were my favorite) and I’d talk to a few quite women here and there and most were just fun conversations. Though it was late in June when I went to this small cafe downtown. No more than a week old it was new and crowded. I sat down with my book and to my surprise this beautiful young looking woman with long black hair and green eyes and D cup breasts (at minimum) walls up to me. “Is this seat taken?” She asked. “Absolutely not. It’s all yours.” I said. She sat down and sipped her chai latte and we just stared at each other for a good long time. “Is that a good book?” she asked. “Yeah it’s not too bad.” “What’s it about?” She asked. It was a book about one woman exploring her sexuality with five different guys. “It’s an erotic novel.” I said. She leaned in and smiled. “I love those.” This took me by surprise and we started talking deeper. She explained that she had two daughters both were in high school. She had just gotten out of a relationship that went bad. We talked for two hours straight and she got up and asked; “would you like to continue this conversation elsewhere?” So I followed her to her house which was a two level, four bedroom and two bathroom house. Make yourself comfortable she said and she disappeared into a hallway for a time and as I admired the pictures-(her oldest daughter Tanya was 17 and had short brown hair and green eyes, larger breasts, c-cup at best. Ella her second child 15, had light brown hair and blue green eyes, smaller breasts B-cup for sure.)-Chelsey walked out in a long silver silk and cotton lace robe that went down to her thighs. She took me by the hand and led me down the hall where she set me on the bed. She walked over to the closet and opened the walk in closet and to my excited surprise she had bins full of sex toys. Straps, dildos, plugs, flogs, whips and lots more. I was drooling puddles in my mind. “Do you think we can continue that conversation?” She said wittily and I stood up and grabbed her by the waist and threw her into the bed. We made out for a long time. Just making out had gotten me hard and she knew it. I pulled away and looked down at her and she knew what I was thinking. “Don’t hesitate. Don’t think. Don’t worry. I’m not your ex, and I’ll let you know if and when something is too far.” She said. Without a single word I went to the closet and rummaged around and found ankle straps and wrist straps and I tied Chelsey to the bed. Naked and sexy she was a sexual dream come true…but then… “Mom! We’re home!” I went into panic mode. I had her mother tied up naked and I was still clothed and the closet full of toys was open. I took a few deep breaths and looked to Chelsey nervously who smiled and arched an eyebrow. “Girls I’m in here.” Chelsey shouted. My eyes went wide and my heart sank to my stomach as Tanya and Ella walked in. “Oh. Hey mom.” Tanya said nonchalantly as if seeing her mom tied up was no big deal. “Can I join you?” Ella asked excitedly. Chelsey looked to me questioningly. “Do you care if she is part of this?” I had no idea what to think and I just shrugged. “Tanya?” Chelsey asked. “I’ll pass. I’ve got too much homework to do. Maybe next time.” She said and walked out. Ella dropped her backpack. Took off her dress and shirt and sat on the cushioned chair next to the bed. I was still frozen in place. “Don’t be worried. I give you full permission to do whatever you want to my daughter.” This was really happening I thought to myself and I snapped out of it and grabbed another pair of straps and tied Ella to the chair. My lips met hers and they were so soft and so sweet. Oozing with young hormones that I could taste. I noticed Chelsey was breathing heavily as she watched me kiss her daughter. I started to make out harder with her daughter and rubbed her 15 year old pussy which was wet and unfurling. I pulled off my pants and shirt and boxers and stood naked. With an full seven inches and a fit body I was feeling confident and sadist like. I went down between Chelsey’s legs and started eating out her pussy. My tongue slipped in and out and up against her clitoris and she moaned. Ella was moving in her chair anxiously. With fingers and tongue I worked Chelsey through the first orgasm of the day. I moved to Ella and leaning her hips down I slowly and tenderly ate her pink pussy. She moaned loudly as my tongue and fingers massaged her pussy and clitoris and within half the time of her mother Ella came in my mouth. A sweet smooth cum that I licked up. I was really starting to feel this and they were too and my sadist side came out. I moved Chelsey onto her stomach and with the black flogger started flogging her ass and back. Chelsey whines louder and louder as I flogged harder and harder leaving thick red marks. Chelsey pushed her ass into the air revealing the strings of cum dripping down from her pussy. I moved to Ella and positioned her and started flogging her ass too. Ella moaned with each stroke of the flogger. “Please…fuck me.” Ella begged and at that moment I really wanted too. I went to the closet and grabbed the green vibrator and Chelsey was quick to react as the vibrator slammed into her clitoris and she arched up and screamed as I turned the vibrations up and she came again. Cum dripping down the vibrator. “Oh god your such a tease!” Chelsey moaned. I moved to Ella and turned the vibrator down and Ella was even quicker to react and as I turned the vibration up she came. I turned the chair around so that she faced her mother and without hesitation I slid my cock into Ella’s pussy. So tight and young and wet. I pushed my cock halfway in and enjoyed Her moans. I pulled back and took her small nipples in my fingers and squeezed hard as I pushed in again. It was tighter the deeper I got. My cock reached the tip of her cervix and she screamed and came a river onto my cock. Her pussy tightened around my cock so hard I thought it might lose circulation. I watched Chelsey the whole time as she enjoyed seeing her daughter cum. I flipped Chelsey over and sank my cock deep into her pussy sparing no time to adjust to my size. I couldn’t help it. My cock pounded her pussy. She moaned and screamed with pleasure as she tried to pull against the cuffs. Using the vibrator against her clitoris while pounding her pussy she came. “Oh god! I’m cumming! Oh fuck!” She screamed and convulsed. I looked at Ella who was ready to climax just by watching us fuck. My cock was ready to explode. Chelsey knew it too. “I want you to unload in my daughter. Don’t hold any back.” She said and I went to Ella and took off the cuff and as I made out with Ella I lead her to the bed and repositioned her so that she was on her knees face to face with her mother. My cock slammed into her pussy and I held nothing back as I pushed all the way into her. She screamed in a mix of pain and pleasure. I could see Chelsey was enjoying it. I pounded harder and harder and Ella came on my cock her pussy so tight it made me thrust harder and faster and deeper and in no time at all she came again and i felt my cock harden and at that moment I had an idea. I turned Ella around with Chelsey beneath my balls she watched as my cock fucked her daughter’s pussy hard. Strings of her daughter’s cum dropped down into her face. My cock slipped into her cervix and I couldn’t hold it back any longer and I unloaded. My cum came out in heavy large loads filling up her pussy and oozing out the sides. I pulled out and with my cock covered in cum I slid it into Ella’s mouth. “Push my cum out baby. Let your mom eat my cum from your pussy.” I said. Ella pushed as she drank the last of my cum from my cock. Chelsey took in my white thick cum as it fell from her daughter’s pussy. An amazing experience!

Chanshy

We still had two nights before our parents came home, and I looked forward being as rough and loud as we could until they got back.

During college, my sister and I shared a dorm room. As twins it wasn’t anything special, we were best friends and had shared everything. That we weren’t the same gender had never stopped us in any way. One particular night we were bored and decided to hit up a party we had heard about downtown. We didn’t know anyone else going there, but it didn’t matter; we had each other. The party was great! Some rich kid owned the place, and everyone got free booze. We had more than our share and had loads of fun dancing to the music. Almost out of breath from all the dancing we swooped down into the last empty space in the sofa, my sister on my lap to also rest. We were both pretty drunk, but at least still sober enough to keep control of ourselves. “You make such a lovely couple!” a girl complimented us, the smiles of the other guests hinting they agreed. “We’re not a couple!” I answered, laughing at the notion. “You should be!” She laughed, and everyone joined her in the suggestion. I saw my sister blush and was about to tell everyone the truth when I saw the smile on her face. She enjoyed their words, savoring the compliments showered at us, and I felt her grab my hand as she held it in her lap. This went on for quite a while, joined by drink after drink, and soon it almost felt like we had our own personal cheering squad. “You should kiss!” The girl said, suddenly. “Come on! At least just once? Just to try it!” I was about to open my mouth, but soon anything I would have tried to say would have been drown by the crowd’s repeating chant: “Kiss! Kiss! Kiss!” My sister got up. I figured she finally got tired of their nagging as she stood up in front of me, facing me. Her right knee landed right beside me, quickly followed by the left on my other side as she straddled me in the sofa. Pushing against me, her eyes pierced straight into mine as the crowd cheered on, a look in her eyes I had never seen before. Lust. Pure, feral lust emanated from the expression on her face and I knew her well enough to realize the sparkle in her eyes told me her goal was set. The thing about my sister is that she always gets what she wants, I had learned to not even try to win over her in an argument, but as her lips touched mine and I felt her tongue in my mouth it reached a whole new level. I heard the crowd cheer as her hands grabbed my head and she kept kissing me. I could feel my urges stirring and my arms wrapped around her body as my tongue met hers. This wasn’t the first time I kissed someone, far from it. Just like her I had a way of always getting what I wanted and had more than my share of girls. But never before had it felt anywhere close to like this kiss. Never had I felt so close to anyone, as if we were made to match each other, and I felt it throughout my entire body as we kept on making out. Like it was all a dream time flew by, hours, as we just sat there joined together as our hands moved across the other’s body. There were only a few guests left and as time had passed it seemed we had both missed how many hours had gone by until we finally stopped and looked around. With just a handful people left, the party had become much more private and while the worst buzz was gone, I could tell on her body language she was far from done yet. My sister smiled at me, her eyes still sparkling like diamonds, and bit her lip as she eyed me up and down. She pulled down her dress and held her naked chest just inches from my face. I had seen her naked many times before, but not until now did I truly appreciate the delicate form of her breasts, just large enough for me to cup my hands around them, her fairly small areolas and the small button-like nipple in its center really made my mouth water. To my delight she pushed it right into my mouth and I spared no time waiting to suck it. My tongue played around her nipple as I suckled her breast so intensively, I completely forgot the people surrounding us. “I think they’re gonna fuck!” Someone said suddenly. “Ohh, I hope so!” I heard another voice answer, recognizing it as the girl urging us on earlier. Disappointed, I felt my sister pull her tit out of my mouth but as she slowly slid down, pushing her breasts across my entire body, and landed her head between my legs as she started to unbuckle my belt I knew she’d make up for it. Unzipping my pants and pulling down my boxers my rock-hard cock popped into view, making my sister gasp at the sight. The whispers from the onlookers quickly revealed her gasp coming from the surprise at the size of my dick. She moved her fingers around my shaft and pulled it down toward her mouth and wrapped her lips around it and began to slide her mouth up and down my cock. With each repetition, she came closer and closer to the base. Our passion seemed contagious as I could see two girls making out just beside us, while a third, our cheerleader, was stroking another guy’s cock. Soon they were all naked, and one of the girl’s head landed right beside me, while the other girl pushed her pussy into her face as they started to eat each other out sixty-nine-style right there beside us. My sister’s lustful gaze kept its focus right into my eyes as much as she could while she did her best to push my cock down her throat. Slowly and steady she sucked me for at least ten minutes before I felt her lips against the base, and her tongue playfully moving around my balls. With a victorious grin she smiled at me as she let go of my cock, standing up and once again straddling me. Pulling up her dress, she revealed she wasn’t even wearing any panties as she put my dick right against her pussy. It was already soaking wet and I felt its warmth as she slowly slid down my shaft with a blissful moan. Our onlookers seemed to like what they saw, as they were merely touching themselves by now while enjoying the view as my cock went deep into her. I moaned as I felt the tip push against her cervix, and she started working up and down my cock. Never had I been so horny, and I felt like I would come in an instant. My sister, knowing me enough to realize, leaned in against my ear. “Cum inside me.” she whispered, my disbelief showing on my face. “Don’t worry, it should be fine.” That was more than enough for me, and obviously for her as well as I felt her muscles clench around my cock as it started pumping load after load into her pussy, pushed hard against her uterus. She kissed me again as I kept pumping her full of my seed. Our onlookers were full on having sex just like us, and we sat there for a while, watching them, as my cock held my cum inside of her like a plug. Moments later she got off, letting the cum simply seep out slowly down her leg, and we started walking home together. “I can’t believe we just had sex in front of all those people.” She said, holding my hand. “Yeah, we had sex…” “I sucked your cock.” She smiled. “I really liked it.” The second we got home she threw off every piece of clothing she had on and threw herself onto the bed. I was quick to follow in taking my clothes off while she got on all fours, presenting her soaking wet pussy right before me. I got down behind her and pushed my face right in and started eating her pussy. Her juices flowed and I could feel the taste of my own cum remaining inside of her as I licked up each and every drop. When I felt that she was eager to go on I got up behind her and slid my cock inside her pussy again. My hands wrapped around her waist in a firm grip and I fucked her hard, making her cum over and over again while I pumped load after load into her.