I had known Sandy for pretty much my whole life. She had moved in next door to me when I was like 9. We were the same age and got along pretty well. I would go over to her house and hang out alot in their basement. Even before puberty I thought she was pretty cute, Skinny, kind of elven features and long dark hair. As our bodies matured over the years, I began to take more and more notice of her. By the time we were 17, Sandy had grown a nice set of size B tits and just a little bit of an ass. She was about the same height as me; 5'8" and pretty skinny. She wan't the best looking girl in school but plenty of guys seemed eager to date her.
I still went over to her house and we talked alot about dating and sex. Sandy had never done anything. I had been with her friend Becky who had been around a little and was reputed to give the best blow jobs in school. While I still had nothing to compare her to, I didn't doubt it. Sandy would ask me a lot about it, what it was like and how it felt and stuff like that. I didn't mind talking about it because it kind of turned me on to see Sandy staring at me, obviously as aroused as I was. The problem was that having sex with Becky had kind of created a stigma. Even though she was Sandy's friend, she was pretty much considered to be a slut and Sandy didn't want to be with anyone that had been with Becky. I thought it was kind of stupid, but at the same time I kicked myself for ruining any chance I might have had with Sandy. Well I wasn't willing to give up just yet. I'd tell Sandy that It was good but that I didn't really like Becky that much and I was sure it would be better with someone I cared about. Lying, I told her I wished the first person I'd done it with had been someone I knew really well and was comfortable with. She nodded a lot, like this made sense to her. I also told her how I wished Becky had'nt told everyone like she did. I didn't mind the way girls did but it did seem to make a lot of girls unreachable for me. She nodded and said she would like to keep her sex life quiet. We continued to stare hungrily at each other and continued what I now perceived to be a subtle but important negotiation session. Sandy said how important safe sex was to her. She didn't want to get pregnant or worry about STDs. I agreed whole heartedly saying that I had used a condom with Becky but that if I knew a girl was clean I would really like to try bare back and just pull out because I wanted to know what it felt like. Sandy frowned a little and I quickly stated that of course I would be willing to wear a condom, bare back was just something I wanted to try. She smiled and moved a little closer to me.
It was about 5 o'clock and we decided to break for dinner. I ran home and had a hurried meal and then ran and showered up and shaved and brushed my teeth. I ran back over to Sandy's house by 5:45. She also had finished eating and had changed into some easy clothes. She had on some very thin pajama bottoms and a little cotton t-shirt. I could see she wasn't wearing a bra and was delighted by the implication. Sandy told her parents we were going down into the basement. Her dad just kind of grunted as he sat with his beer, staring at the news. her mom, Gretchen, smiled and gave us a look like maybe she knew we were up to something. As we went down the stairs I looked at Sandy's ass and it looked like maybe she wasn't wearing any panties either. I felt my dick growing hard as I imagined what we might be about to do. In the basement it looked like Sandy had been busy. Theirs was an unfinished basement and nothing special to look at but Sandy had let down an old futon in the corner and covered it with a clean blanket. She had a lamp covered by a scarf to give off a dim light. We approached the corner in kind of a trance. Sandy sat on the futon in front of me and in a halting voice she asked me if she could see it. I fumbled eagerly with my jeans and she helped me pull them down so my cock sprang out and hit her in the head as she sat back up. She stared at it and I could see she was excited. I put her hand on it so she could feel it. I've always been a regular 6' 1/2" , sometimes I've thought I looked bigger or smaller but anytime I've measured it's been the same. Well, Sandy seemed mesmerized and she pulled on it lightly for a few minutes. I could see her nipples hardening through her shirt and she was unconciously rubbing her thighs together. My dick grew rock hard at this and she loved it. I wanted her to put it in her mouth but I also wanted to see her tits since I'm a voyeur at heart. I pulled her up and hugged her to me. I looked into her eyes and kissed her. She had never kissed anyone and I had only kissed Becky but it was still one of the best kisses I've ever had. We moved our tongues around each other and I rubbed my hands up and down her back inside her shirt. She moaned a little and we both decided to remove our shirts. Her breasts were beautiful. Small but firm they pointed straight forward capped by small pink areola and hard little nipples. I cupped them both and rubbed them in a clockwise manner. She seemed to like this and kissed me deeply as I did. I pulled her to me again so I could feel her tits on my chest, it was electrifying. I reached behind her and cupped her ass, pulling her closer to me. My pants were still around my ankles and my cock pressed firmly against her belly. Only the thin fabric of her pajamas seperated me from the pussy I had been dreaming about for years now. I reached under the waist band and cupped her bare ass as we ground together, lips still locked tightly. I was afraid I was going to cum prematurely so I laid Sandy down on the futon and after kicking my own pants off, helped her remove her pajama bottoms. Wow! her pussy looked so good. Just a small triangle of dark hair that seemed to thin around the lips of her pussy. I could see it was puffed up a little and moisture was visible around her slit. I told her I wanted to taste her and she agreed. I hadn't gone down on Becky because I thought she was kind of gross so this was my first time. I was amazed at her pussy as I dove in. I could smell her musky aroma and as I ran my tongue lightly up her slit, I could taste her mild kind of creamy saltiness. Sandy moaned and I began to kiss her all around the inside of her thighs and around her pussy. "Put it in me." she begged and I obliged. I ran my tongue along her slit, each time forcing it in a little further. I could feel her inner lips on my tongue and her tiny clit at the top. She shivered each time I hit her clit and I picked up the tempo. Soon I was focused primarily on her clit and every ten flicks or so I would plunge my tongue as deep in her pussy as I could. Sandy loved this and her hips would buck wildly in my face when I pushed my tongue in. Just as my mouth was really getting sore (I was loving this but I never imagined how much work it entailed) I sensed Sandy's body tensing up. She was about to have an orgasm and I picked up the pace. Flicking as fast as I could, I rubbed her belly with one hand and her pubic mound with the other. Her hips started bucking again and her breathing was ragged. We were trying to be quiet since her parents were upstairs so she let out a lot of quiet whimpers. After a few seconds she shuddered and relaxed. I had been sucking lightly on her clit and felt just a small amount of warm liquid spill out of her cunt. "Oh, god that was amazing." she told me. I laid next to her and grinned. I ran my hands around her sexy body and stared at her face. I ran my left hand down to her pussy and slid my middle finger along her slit. I did this for a few minutes and we kissed. At some point she must have decided she was ready for me, because she turned into me and I pulled her body against mine. My cock was still hard, never having gone down. I rolled on top of Sandy and got her legs apart. We were looking deeply into each other's eyes as I pressed the head of my cock against her swollen pussy. I wanted this moment to last forever as I slid it into her wet cunt. Sandy shivered and I let out a few moans of my own as I buried myself to the hilt. Slowly at first, I slid in and out of her slick honey pot. She felt amazing and I felt my balls and abdomen tightening within the first minute. I realized I didn't have a condom on and said something. Sandy said she knew and had decided she wanted to give me something special. I smiled and thrust harder into her. Sandy roser her hips to meet me each time I thrust into her. "You feel so deep." she kept telling me. I pulled her legs up over my shoulders and started ramming into her even harder. She moaned and the futon was creaking pretty loudly but I didn't care. I slammed into her with all my might and my dick started spasming uncontrollably. Sandy's body was shaking as I pulled out and shot a huge load across her belly and up to her tits. Oh, my god, it was the greatest feeling I'd had in my young life.
We laid there for a few minutes caressing each other's bodies and talking about little things we had liked. I felt my dick getting hard again and was thinking of what I'd like to do next when I saw a little movement out of the corner of my eye. I turned into Sandy and gave her a kiss. As I did this I could see over her shoulder and there was Gretchen at the foot of the stairs kind of peeking around the partition at us. I don't know what wickedness posessed me but I looked straight at Gretchen as I said "I want to feel your mouth on my cock." Sandy agreed and I knelt on the futon and Sandy got on her knees in front of me. My cock was rock hard and Sandy started sucking on it. To my amazement. Gretchen was still standing there looking. I was so turned on, Sandy was bobbing up and down on my dick with her naked ass and dripping pussy facing her mom. I grabbed Sandy's hair and pulled her off my dick as I bent over for a long kiss. When I came up again I wagged my dick in her mom's direction and rubbed it around her face before sticking it back in again. "you like that don't you." I said, still staring at her mom. "You like my big cock in you mouth." Sandy moaned affirmatively and her mom just continued to stare. I realized that I could only see one of Gretchen's hands, her other arm was hidden by the partition and she seemed to be moving ever so slightly back and forth. I had never really thought about Gretchen sexually but I was now. Just an older version of Sandy, she was pretty good looking and still fit. I imagined her sliding her hidden hand in and out of her pussy. "Oh, god that's good. Is your pussy getting wet?" I asked, still focused on Gretchen. Sandy moaned affirmatively and this time I thought I saw Gretchen nod a little too. "You want to feel my cock in your little pussy?" I asked and Sandy came up saying yes yes. Gretchen looked a little worried but I quickly told Sandy to stay where she was and I got off the futon behind her. She was kneeling in the perfect position for me to fuck her from behind. I pressed my dick against her pussy and said "Tell me you want my dick inside of you. Tell me how bad you want me to fuck you." Sandy's head was pressed down into the fabric of the blanket and I was looking at Gretchen again. She was nodiding. She wanted me to fuck her or Sandy or both of them, I couldn't tell. Sandy started to say "I want you so bad. Put it in me please, I want your cock inside of me." I obliged by plunging it violently into her. She moaned loudly and I started to fuck her hard. You could hear skin slapping together each time I rammed into her. "This feels so good, I could fuck you lke this all day." I said and I saw Gretchen shudder. I imagined her having an orgasm from masturbating herself and felt my stomach and balls tightening again. I rammed harder into Sandy's hot snatch and she gave a little grunt with each thrust. I wanted to cum soon, I was afraid Gretchen would leave before I did. Her eyes were a little glazed and she was still staring as I pulled out of Sandy's box and shot across her ass, rubbing my wet cock along her ass crack. Sandy sighed, Gretchen stared and I smiled eveilly. "Did you cum?" I asked and Sandy said yes. I looked at Gretchen and she nodded looking embarrassed and slipped away.
Sandy and I laid there for a while and talked some more. She said she really liked me talking dirty like that and where did I learn it. I couldn't really say. I was thinking a lot about Gretchen but was still really into Sandy as I rolled into her and we made love one more time. On our sides facing each other I managed to get my dick inside of her. We lay there, fucking slowly, grinding for a long time. I slid my hand around her spread ass cheeks and up and down her crack. Sandy didn't seem to mind and finally I settled my middle finger on her little pink asshole. She seemed to like this and we writhed together for several more minutes. "I want you to cum inside of me." Sandy said, before we both shuddered and I shot inside of her. We worried about that a little bit but Sandy said she had just had her period and we figured since it was my third time maybe there wasn't that much and so on. We decided to let it go and not worry about it. We talked some more and kissed and caressed each other and finally decided to call it a night. "Jeez, we were loud enough a couple of times, I'm surprised my parents didn't come down to see what we were doing." Sandy giggled. I laughed a little too and said maybe someone did cum and we just didn't see them.
I was eager to get with Sandy again but unfortunately that weekend she and her dad were going up north to open up their cabin and clean it out. I spent Friday night jerking off and sleeping fitfully as I thought alternately of Sandy and her mom. Saturday morning I was feeling pretty bold and decided to go over to Sandy's house. I knew Gretchen was alone and even though it would be obvious, I figured I would pretend I didn't remember Sandy was out of town. I got cleaned up, shaved and brushed my teeth and snuck nervously over to Sandy's house. I walked right in and yelled hello like I usually did. I heard some moving around and I could tell the tv was on. A few seconds later Gretchen said hello from the living room. I walked into the living room and saw her seated on the sofa in a bathrobe drinking coffee. I asked if Sandy was around and she said no, Sandy had gone up north....... "Oh yeah, " I said, "I totally forgot. Oh well, so you have the whole house to yourself this weekend. Do you have any exciting plans?" I grinned at her as I said this and walked around the living room looking around. She looked a little nervous as I approached the tv and said "No, I was just going to relax and maybe do a little cleaning." I saw the vcr was on but stopped and on the side was a video cassette sleeve, it was a porno. I was familiar with it since Sandy and I had seen it a few times ourselves, it was her dads. Staring at the porno tape I asked in a husky voice. "Is your pussy wet right now?" I turned to Gretchen and she was looking at me like a caged animal. She was kind of stammering but couldn't really say anything. I walked to the couch and sat down next to her. Placing a hand on her knee I said "I know you liked watching me fuck Sandy. You did, didn't you?" She nodded like she was hypnotized. Staring at her face I asked "Did you cum while you were watching?" She nodded again. "Do you want me to do to you what I did to your daughter?" I said and she nodded again. With that affirmation I began to slide my hand up the inside of her thigh. I found that she was wearing no panties and she was indeed wet. Softly I slid my fingers along the soft folds of her wet pussy and she sighed and leaned her head back with her eyes closed. I leaned over and kissed her neck as I slid two fingers into her slick pussy. "Let's go into your room." I suggested and she agreed. We got up and I followed her to the back of the house. as we did this, I reached out and pulled her robe from her shoulders. She was completely naked underneath and as her robe fell to the floor, I admired her tall, thin form. Like Sandy, she was about 5'9" and weighed maybe 135. She had light tan lines around her ass and back. her ass sagged a little but still looked good to me. Her thighs were thinner and I could see a few dark curls peeking out between her legs. Gretchen's hair was short, a mom haircut, and as we got to her bedroom and she turned to me I could see her breasts were small like Sandy's and still firm. She had a bigger triangle of pubic hair, still sparse and kind of dusky, lighter in color than Sandy's.
I was feeling pretty confident and I pulled her to me. I drove my tongue into her mouth and after some initial retiscence she pushed her tongue back. She ran her hands frantically over my body, desperately trying to remember the feeling of a young hard body compared to her husband Leo's soft chubbiness. I pulled my shirt off and rubbed my chest against hers and her nipples poked me, they were bigger and darker than Sandy's and I pinched one of them. This sent a jolt through her body. "Tell me you want my cock." I said. "I do want your cock..." she said as she worked the snap and zipper of my jeans, "Leo is the only man I've been with, we were High School sweethearts and we got married right after. I've always fantasized about feeling another man's cock inside of me and when I saw you with my daughter I knew I should turn away but I couldn't. Leo's penis is only 4 or 5 inches and I knew Immediately that I wanted you. I felt so bad but I couldn't stop staring." She got my pants undone and I stepped out of them, removing also my shoes and socks. We stood there facing each other. I never thought of myself as huge, but I guess compared to Leo I was and I proudly placed her hand on my stiff prick. Gretchen stared down at it, hunger in her eyes as she rubbed my glistening dick with pre-cum. "Suck it." I told her. I knew she wanted to and she dropped to her knees and placed it at her lips. Becky might have given the best blow job in High School but she couldn't begin to compete with Gretchen. She was loving on my dick like she hadn't eaten in weeks. She started with just 4 or 5 inches of it, presumably because that was what she was used to, but soon she was engulfing my entire cock as I lost control and began fucking her mouth. She gagged a few times but when I pulled her off me she just clamped back on my cock and started bobbing again. It was amazing. "Yeah, you're a good little slut." I told her, "Suck it, suck my big cock. You love it." She grabbed my ass cheeks and pulled me harder to her. Back and forth she slammed her face into my pelvis, slurping loudly, I could see thick spittle running down her chin and onto her chest. "I'm gonna cum in your face." I groaned and my ass tightened up in her hands and I pushed my cock as deep into her mouth as I could. Gretchen gagged again as she stared into my eyes and I pumped my fluids down her throat. She pulled her mouth off me and showed me a mouth full of cum before licking her lips and swallowing it all. This I realized was straight from the porn video she had been watching.
I laid her on the bed and got between her legs as I tried to remember what else happened in that video. A lot of the usual stuff, stuff I had already done with Sandy. Also, though, I remembered a guy fucking a girl in the ass. I rubbed my already stiffening cock on the bed spread as I dove into Gretchen's drenched pussy. She was cleaner than Sandy and must have douched. there was almost no taste at all. I licked her up and down her slit, one hand on her belly, the other caressing her leg. Gretchen moaned and said that Leo didn't like to go down on her. He liked to watch his videos but never actually did anything but missionary and occasionally doggy style. I sucked her engorged clit, bigger than Sandy's as she tightened her legs around my ears. She squeezed hard as she came and I was rewarded with a small rush of hot liquid. I lapped it up and collapsed next to her on the bed. She must have been watiting for something like this for a long time. Immediately she was on me, rubbing my cock to full attention. My hands wandered along her length as I kissed her deeply again. "Tell me you want me to fuck you." I said, remember the other night with Sandy and also thinking of the video. "I do, i want you to fuck me so bad." Gretchen said. I told her to get on her knees and she quickly obeyed. I got behind her and pushed my cock against her pussy. I slid it in and pulled it out again. With this wetness, I slid it along the crack of her ass taking care to rub it hard against her puckered brown anus. She moaned and begged me to put it in her pussy, and I shoved it in again. After a couple of shoves I pulled it out again and rubbed it on her ass. She was lubed up pretty good and when she begged again I shoved it back in her pussy and started pumping away. She moaned and shoved back hard on my cock everytime I thrust. Her pussy was boiling and as she slid forward she would clamp down tightly on my pole. I was loving this and watching her now glistening asshole shiver back and forth. I put my thumb on it and she moaned loudly. I began gently to massage her little shit hole as I fucked her. She loved this and came almost immediately. Abandoning her asshole for the moment, I leaned into her and reached around to massage her clit with one hand while pinching a nipple hard with the other. Rather than fuck her, I pulled her hard onto my dick, over and over until I was ready to cum. "Cum inside me," she panted, "I cant get pregnant anymore." That was all I needed. I pulled her hard onto my dick and shot my load inside of her. We fell on the bed and I lay on top of her with my dick shrinking and sliding slowly out of her sticky slit. "Oh, god," she groaned "I've never come so many times in my life." I laughed wickedly, "Well get ready for some more, I'm gonna fuck your little asshole." She gasped in mixture of shock and delight. I reached into a side drawer and removed a jar of vaseline. Gretchen didn't even bother asking how I knew it was there. Before I did anything though, I knew I wanted to taste her little asshole. I got a couple of pillows under her hips which put her ass up at a nice angle. Laying on my stomach I leaned into her crotch. lovingly I cleaned her pussy first. some of my cum was leaking out, mixed with her own and I lapped it all up. Gretchen groaned and and I worked my way up to her taint. Licking the area between her pussy and anus sent shivers through her body. I thought of how Sandy had reacted to my finger in her asshole and knew it had to run in the family. As I ran circles with my tongue around her anus, Gretchen squirmed impatiently. Finally I got to her puckered asshole and savored the feel of her tiny ridges on the tip of my tongue. I swirled and poked and sucked as she ground her ass in my face. "Oh, Leo would never go anywhere near my butt." she moaned. I licked heartily as I inserted two fingers into her pussy. More moaning, shivering and I'm sure a few orgasms as I pushed my fingers in and out of her soaked pussy, plunging my tongue simultaneously into her warming asshole. after she came a few more times I got up on my knees. I left my fingers in her pussy as I wrestled the vaseline open with my other hand. I scooped a table spoon or so onto my finger and smeared it on her ass. Her whole body quivered with anticipation and delight as I lubed up my middle finger and slowly slid it into her. Her asshole was amazingly hot and tight. I slid my finger in and out slowly for a few minutes before adding a second. She loved this and was soon thrusting her ass at my hand in an effort to speed up the motion. I got the message, she was ready. I pulled my hand out of her ass and my other from her cunt and began to lube up my stiff cock. She whimpered with dismay. "Tell me you want me to fuck your ass. Tell me you can't wait to feel my big cock in your ass." I adored her as she did just that. Wagging her ass wantonly in my face she begged me to shove my cock in her ass. "Oh, god yes, fuck my ass. Please shove your big cock in my ass." She was already fingering her clit as she begged me. I laid it on her crack and slid it up and down a little and she begged me again. I wanted to tease her a little but my cock was so hard and leaking pre-cum again, I couldn't wait. I pushed it against her sphincter until she relaxed and I slid in. She grunted like she was constipated as I slid all the way in. I could feel her knuckles against my balls as she furiously rubbed her pussy. She groaned again as I slowly withdrew and then plunged it in again. I couldn't believe the feeling, so much hotter and tighter, as I plunged in again and again. Gretchen loved this and I recalled the video as she started chanting "Fuck me harder, Fuck me harder, I want to feel your hot cum in my ass." As if it was possible, I felt my cock swell up bigger than before. I felt like the veins were going to burst. I was slamming into her ass, watching my cock disappear up her poop shoot again and again while she chanted this. Suddenly for the first time, she wanted to play my game. "Tell me how good my asshole feels." She demanded, "tell me how good my asshole tasted." and like a good boy I did. Gretchen slammed harder and harder on my cock as I told her how great her asshole was and began to shake violently as I said how I loved sucking on her dirty little shithole. Her body shook in long convulsions and her ass clamped tightly on my cock. All I could do was grind against her ass as we both collapsed on the bed and I shot an impossible load into her bowels. We both spasmed for what seemed an interminably long time and just lay there. I was feeling faint as I pulled my cock from her ass and watched it slowly close up. I had a momentary urge to plunge my tongue into her rectum before it closed up but didn't have the engergy. Another time, I thought.
We played around a little more and then I went home for a shower and a nap. I ate like a horse when I woke up and told my parents I was going out. I snuck back over to see Gretchen and we spent the rest of the evening fucking all over the house. It was some of the dirtiest and best fucking I've ever been a part of. As I shoved my cock into her mouth in the shower, I'd say things like "Suck it bitch, Suck it hard." and as I reamed her asshole again over the kitchen table I told her how I was going to do the same thing to her daughter next week while she and Leo were at work. She moaned in extacy, excited at the thought of it. As she rode my cock on the couch with my finger shoved up her ass she reached under a cushion and produced a big black dildo which she demanded I stick up her ass. Later after she had licked my asshole and fingered it warmly, I let her stick the dildo in my ass while she sucked me to a mind blowing orgasm. I was exhausted when Sandy and Leo got back but managed to find the strength to eat her out in the basement and fuck her a few times while massaging her little asshole.
Later that week, I did manage to fuck Sandy in the ass over the kitchen table and she loved it. Just like her mom she was shoving her ass at my by the end as I slammed heavily into her. After I came, I dripped a little in the chair Gretchen would use so she could find it later. After a couple of weeks of this Sandy and I kind of agreed that even though we loved fucking, we wanted to date other people. We still got together once in a while between girlfriends and boyfriends and Gretchen always found a place to watch while I fucked her daughter. I would pound away at Sandy while gretchen would flash me with a that big dildo sliding in and out of her cunt. Just once, when Sandy was tired I managed to sneak off when she fell asleep and Gretchen sucked hungrily at my cock, covered in her daughters juices. then I fucked her furiously in her ass as she grunted painfully. Sandy eventually graduated college and moved out of state. I still run over to see Gretchen when Leo's not around and when Sandy is in town we get together at my house. Every once in a while I convince her to let me fuck her ass in the basement so Gretchen can watch.