My life pt1 by jeff56

I live with my mom, Krystal at 36, my older sister Jackie at 16 and my younger sister Val at 12, my parents relationship fell apart about 10 years ago. In my home nudity was completely accepted, and masturbation was also accepted only in your room, so mostly the girls walked around in just panties and me in just boxers. We live in a nice 2 story house in Sound Beach, NY, 4 bedrooms, 1 1/2 bathroom, the second floor was the bedrooms and the full bathroom, and the first floor had a big living room and a kitchen the same size, and the half bathroom. The kitchen had a door that led to the back yard that had a nice 12′ deep in-ground pool, and a 6′ wide hot tub.

My mom was 5’8″, and about 120 lbs, her skin was a little lighter then mine, and because she ran when ever she could she has long beautiful legs, an amazing ass, and a flat stomach, with 34B beasts topped with areolas as big as a nickel, and nipple as thick as a nickel, with no tan lines as she tanned topless, she haslong wavy blond hair, beautiful blue eyes and a cute nose.

My older sister Jackie, was 5’7″ and no more then 115 lbs, her skin was as dark as mine, and because she loves soccer, her legs look just as good as her mother if not better, with an ass you believe. She has lovely 36C breasts, with cute nipples the size of a pencil eraser, and areolas a bit bigger. She has dark brown hair that runs to the middle of her back, and brown-red with a touch of green eyes, and a nose that matched her mothers.

My younger sister Val, is 5′ and at most 95 lbs, her is lighter then moms, she has beautiful legs, a nice ass, and her tits are just starting to bud, her nipples are about the size of the third prong on a plug, and areolas the same size. She has long straight brown hair, and beautiful hazel eyes.

It was early July and the day started out like any other day, I woke and went to the bathroom, just to find Jackie getting out if the shower and Val getting in, so I took a piss, and went to go eat, and found Jackie eating a bowl of cereal in a tank top and short shorts, “Where’s mom?” I said, “Running.” She responded.

Just as I finished eating mom came home, “Damn, its hot out there, Jeff, honey, can you grab me a drink?” she said stripping off her sweaty training bra, leaving her in only booty shorts that showed off most of her ass. “Now time for a shower.” she said after drinking the whole glass of water. “Can’t Vals in there, and I got next, sorry.” I said, “I just got out, so its all yours.” she said walking into the kitchen in nothing but her panties. “Would you mind if I joined you? After a run like that I need a shower as soon as possible.” she responded, “OK.” I said, remembering last time we took a shower together was when I was 5.

We jumped in the shower, which was only ment for one person, this was the first time I’d seen her pussy in a few years so I had gotten hard almost instantly.

“Oh my! Jeff, you’ve gotten big. Bigger then you father ever was.” she said, trying to keep from laughing. “You still look exactly the same, no droopage or anything, but I remember you being completely shaven, now you have a cute landing strip.” I replied, she slapped me and said “You shouldn’t be looking at you mothers boobs or pussy.” “And you shouldn’t be looking at you sons cock, so were both wrong.” I said. With that we finished our shower.

After the shower I went to my room to stroke my cock, and all I could think about was my mothers beautiful tits and pussy, after a few strokes I could feel that familiar churning in my balls, with two more strokes I started to shoot ropes of white cum all over myself and bed. When I finished I opened my eyes to see my little sister standing in my door way. When she realized I opened my eyes she ran to her room and I was so embarrassed. She had never seen me in any state of arousal, let alone stroking and shooting all over myself.

I went out after that, to hang out with two of my friends, Lynn and Sam. They were both my age, and looked as if they were sisters.

Lynn is 5’7″ and 115 lbs, has long light brown hair, beautiful brown eyes the you could stare into for hours, long shapely legs and an ass that any girl would kill to have, she has 36C breasts. Sam is 5’5″ and 110 lbs,has curly black hair, lovely hazel eyes, long slender legs, a petite ass, and 32C breasts.

At about 2:00 pm we said to hell with it and decided to go to the beach, we decided to walk to Lynn house first because it was the closest to us but the furthest from the beach. When we got there Sam and Lynn went up to Lynns room, and I went to the kitchen to get us some drinks, I went to bring them a drink and figuring Lynn was in the bathroom I just walk in, “Sam I got you and—-” I started saying until I saw Lynn standing there in only her bikini bottoms, and I got a good look at her amazing breasts, her areolas were as big as an iris (the color part of your eye) and a slight bit darker then her skin, and her nipples were about as big as the pupil of you eye.

“GET OUT, STOP LOOKING, GET OUT!” she said while throwing a pillow at me. Sam got up and came out with me and closed the door behind her, she took took two of the glasses from me and brought one to Lynn, “Nice tent.” she said with a wink as she left me standing in the hall. I looked down and covered it with my free hand. A second or two later she came back out and went to the living room.

When Lynn came out Sam an I were sitting on the couch, by now my boner had calmed down, her bikini was an aqua-green with pink trim string bikini with little white bows with black dots on each hip and one in-between her breasts, she had little triangles covering each breast and the bottoms went a little above her pubic region. She put on a pair of shorts as to not get oggled by every boy in town.

“Sorry for that Lynn, I thought you were in the bathroom, but if it means anything they look great.” I said laughing, “Shut up.” she said throwing a couch pillow at me playfully. “Lynn, you should’ve seen the raging boner you gave him, it looked something like this.” Sam said laughing and lifting her shirt to show me her breasts. Her areolas were a little bigger and darker then Lynns, and her nipples were standing out about half an inch. Immediately my cock got rock hard for those two to see, which made Lynn giggle a little.

“Hey look how hard your nipples are Sam, you could cut glass with those.” Lynn said giggling, this made Sam go over to Lynn and pull the triangles covering her breasts over revealing her beautiful breasts to me again, but this time her nipples were just as hard as Sams. By this point my cock was straining to get out of my pants.

“Well this is no fair, you’ve seen our boobs, but we haven’t seen that cock of yours.” Sam said, “Yea.” Lynn agreed. “OK.” I said undoing my pants and pulling down my pants and boxers in one motion, my cock sprung up hitting me in the belly, by the time my cock stopped bouncing, I had two girls on their knees in front of me, but just before Sam touched it, Lynns mom pulled up, so the three of us raced to get dressed and ran out the backdoor, as she’s not supposed to have anyone over without anyone home, especially not a boy.

“Wow, Jeff your cock is huge!” Sam said, as we started to walk to Sams house.

The walk was uneventful, except for a crotch grope from Sam. When we got to Sams house we saw Sams moms car in the driveway, so we knew nothing was going to happen.

When we got there we heard the shower running, Sam and Lynn went to Sams room and I sat in the den and watched tv, and I hear the shower turn off, then Sams mom walks in, not knowing anyone else was there, completely naked drying her hair. Her names Lexie she’s as tall as Sam, ~120 lbs, 36D breasts, areolas as big as a quarter and nipples as big as a WD40 nozzle, a nice fat ass, and a her pussy hair is in the shape of an “L”. When she noticed me, she acted as if I’d seen her naked before, and came over and sat right next to me. By this point I was at full mast, so it was painfully noticeable. She wrapped her hair up and placed her hand a little higher up on my thigh then she probably should’ve. 5 mins later I start wondering where they are, and I notice Lexies hand is resting on my cock, and when she saw that I noticed she started to massage my cock through my pants. After about 5 seconds she starts working at my pants, as soon as she gets my cock out, her eyes go wide, and without saying a word she starts giving me my first blowjob, it took all of my willpower to cum as soon as my cock touched her lips. She bobbed a couple of times, taking only about half my cock, then she went all the way down and held there, with my cock in her throat she started to milk my cock with her throat muscles, and I came almost immediately, it was the biggest, strongest cumshot of my life, and she swallowed all of it without missing a beat. Then we heard Sams door open, I put my still hard cock away pulled my zipper up so fast I almost caught myself in it. When they got out there I made it look like I was trying not to look at Sams still naked mom. Sam had put on a tank top and a pair of shorts over her bikini.

“Mom what the hell, you can’t put on a towel!” Sam said shocked that her mom would be in the den completely naked with Sams friends over, “Sam I am wearing a towel.” she said smiling at Sam. “you know what I mean mom.” Sam said walking toward the door. I got up said bye, and before I could take a step she grabbed me and pulled me into a hug and whispered “You owe me one.” giving my cock a little squeeze through my pants, and slapped my ass when I turned to leave.

“Sorry, if my mom embarrassed you Jeff, she can be a little to forward at time.” Sam said as we started to walk to my house. “Its fine don’t worry about it. I’m warning you two now there will be 3 topless women walking around in my house.” I said. They both just looked at each other and laughed, when they did that I just shrugged my shoulders as if to say ‘dont say I didn’t warn you.’ as I pulled out my phone to text my mom to fill up a cooler with sandwiches and drinks because me and my friends were going to the beach.

When we got to my house I said “I’m telling you again there will be three topless women in this house.” Sam just smiled and said “Right, let’s just go inside. Oh and we’re going to need to borrow towel, because we were kinda rushed out if our houses.” I just said OK and pushed the door open. As we walked in we were greeted by my mom in the kitchen topless preparing the cooler I asked for, Jackie watching tv topless and Val running down the hall also topless. Sam and Lynn just stood there in shock as I went upstairs to change and grab a 3 towels and a big blanket. As I got to the bottom of the stairs Lynn came over grabbed the bag with three towels and I grabbed the cooler. With that we were finally on our way to the beach, at 3:00.

“Jeff, I didn’t think you were serious, your whole family was only wearing panties.” Lynn said

“Makes me wonder what you wear when your home.” Sam said with a wink.

“I walk around in my boxers, maybe you should come over and dress as we dress.” I replied.

When we got to the beach Sam and Lynn took off the clothes they had over there bikinis, Lynn was wearing thong bottoms and Sam was wear a powder blue slingshot bikini, (it looks like the swimsuit Borat wore), luckily the beach we were at was secluded or she might have gotten fined for indecent exposure. “Damn, Sam could you wear a smaller bikini?” I said as my cock began to get hard. “I could just swim naked.” she replied. “I’m good with that.” I said jokingly trying not to sound eager, “How about you Lynn, a little bit of skinny dipping?” I continued with a smirk.”Hmm, OK!” Lynn said excitedly taking off her top. “I never really liked tan lines anyway.” Lynn continued as she stripped off her bottoms revealing a completely shaved untouched pussy. Once I pulled my eyes from Lynns pussy, I looked at Sam who had also stripped her bikini to show off her trimmed pussy, her pubes looked like a pot leaf. “Hey Lynn, we can sleep here tonight, Jeff already pitched a tent.” Sam said laughing, “Yea Jeff, aren’t you a little over dressed.” Lynn said. “We’ll have to make a new tent cause this ones coming down.” I replied laughing and taking my shorts off and letting my rock hard cock spring free.

“Damn Jeff, your cock really is huge, I can’t take my eyes off of it.” Lynn said nonchalantly, “Yea, it does catch attention quickly.” Sam said agreeing with Lynn. “I like how you shaved you pussy to look like a pot leaf, all you need now is some green pubic hair dye.” I said laughing, “But me personally I prefer a smooth pussy, like Lynns.” I continued. “Lets go swimming, its hot out here, and maybe the water will make that monster between Jeffs legs shrink a little.” Sam said giggling, “With you two sexy girls around, my cock will stay rock hard even if it was snowing.” I said laughing, as we all made it to the water.

While we were in the water Sam kept swimming past grabbing my cock, and touching my balls. Lynn was a lot less forward about it, all she really did was stair at it. After Sam touched it about 5 times I swam over to Lynn who was just floating around and asked if she wanted to touch it. When she reached out she was a little hesitant about touching it, when she finally did she kept squeezing and stroked it a little every so often. At one point when Sam swam past, I reached out and squeezed her ass. “Damn, we forgot to put sun block on.” Sam said. When we got back to the shore, Lynn shouted she gets her back done first. So she laid on her stomach and Sam laid on her back and started to put sun block on her front. I took the sun block and put some in my hands, straddled Lynns upper thighs, and I could feel the heat coming off her pussy and onto my balls, as I started applying it to her shoulders, with my cock laying in-between her soft smooth ass cheeks. Every once in a while Lynn would squeeze my cock with ass cheeks. After a couple of those I found myself slightly thrusting my cock in-between her ass cheeks, I could feel my balls bumping into her pussy, when I realized what I was doing I stopped, and Lynn let out a groan, as if to say ‘why’d you stop.’so I rubbed some sun block on her ass cheeks and crack, so my cock would slide through easier. Once I finished her back and ass I was on the verge of cumming so I turned around and straddled her lower back and put my cock back in-between her cheeks and started thrusting again, and once I finished her thighs I felt that feeling in my balls and started to move faster, and then I started to cum on Lynns calves and lower thighs, then I heard Lynn giggle and Sam groan as if to say ‘now I don’t get to feel his cock on my ass’, “Dont worry Sam, his cock still feels pretty hard.” Lynn said squeezing me with her ass.

“Alright Sam, your turn.” I said, with Sam I did her legs first. My cock sitting between her ass cheeks, and her also squeezing me with her ass cheeks, once again I was thrusting in-between her ass cheeks, so I out the sun block on her ass, but didn’t rub it in as thoroughly and it felt so much better. “Dont forget my ankles.” Sam said, and when I reached for her ankles my cock sliped between her thighs and slapped into her wet pussy lips, and she started to move her ass up and down and I could feel her clit sliding up and down the underside of my cock, it felt so good I didn’t want to move, with every movement I heard Sam let out a little moan, after what felt like an hour but could have been more then 5 mins I felt Sam go stiff, and let out a long low moan, and her juices started to flow from her pussy onto my cock. After her orgasm subsided, I reluctantly turned around to do her back, once again I made sure my cock was nestled between her ass cheeks and started thrusting again. after few thrusts I thought I had moved back a little, but thought it was just no imagination, but it turns out it wasn’t because after a about 5 more mins when I pulled back my cock fell from her ass cheeks and before we realized I pushed forward and half my cock plunged into Sams tight, wet, virgin, pussy, tearing her hymen into pieces, her screaming in pain and me letting out a moan of pure extacy, and almost cumming into her pussy, “OH MY GOD! Jeff get that monster you call cock out of my pussy now, it hurts so much.” Sam said “Hold on Sam if I move at all I will cum, and neither of us want that.” I replied. After about 5 seconds I pulled out, “Sorry Sam, I didn’t mean to shove myself into your pussy.” I said, “It’s OK, I should’ve told you when I felt you sliding back, but now I’m going to be sore for a while.” Sam said.

“OK, so who’s going to put sun block on me now.” I said laughing, “I got front.” Sam said, Lynn just let out a disappointed low groan. I laid down on my back and Sam straddled my upper thighs my cock lined up with the stem of the pot leaf on her pussy, and squirted the sun block straight onto my chest, “Thanks Sam, now it looks like I came on my chest.” I said laughing as Sam started to massage the sun block into my chest, when she leaned over my cock got squeezed between our stomachs, then she slowly worked her down to my abs, then she turned around and my cock was once again nestled in her ass crack, she leaned forward to do my calves, and I got the best look at her pussy, her clit was protruding and so were her inner pussy lips, but for the most part all you could see was her outer pussy lips, I wanted to lift her up and stick my cock right back in her. After she finished my legs she turned around and sat on my thighs and squirted the sun block directly onto the head of my cock and my balls, then reached down to start rubbing it in, as soon as she grabbed my cock I let out a long moan, and she started to move her hand up and down my cock to rub the sun block in, and she took her other hand and started to massage the sun block into my balls, she kept moving her hand up and down my shaft at a teasingly slow rate, very slowly picking up speed, long after all the sun block was gone she finally started stroking me at a good speed, and after what felt like forever I felt that feeling in my balls and started to shoot long white ropes of cum into the air, land on my chest, abs, and some even in Sams breasts and hair.

Once I stopped cumming I asked Lynn to get me a napkin from the cooler, and she came over and started to wipe off my chest, Sam got up and grabbed a napkin to wipe my cum off her chest and out of her hair, when she went to wipe off her chest she noticed she had some cum on her hand and licked it off

“Lynn taste some of his cum, it tastes pretty good.” Sam said as Lynn finished cleaning my chest.

“Damn it, why didn’t you say something sooner I cleaned up all of it already, all that’s left is the little amount on his cock.” Lynn replied.

“So taste what’s on his cock, cause if you don’t I will.” Sam said reaching over and grabbing my soft cock. Then Lynn bent bent down and licked it right off my cock, making me moan. “Mmm, your right it does taste good, alright Jeff turn over so I can do your back.” Lynn said patting my cock a little bit. After I flipped over she straddled my ass and started to massage my back with the sun block, while she was rubbing it in I felt her grinding her wet pussy on to my ass cheek and every so often I would hear her let out a small moan, after she finished my back she turned around and sat on my lower back and went back to grinding her now dripping wet pussy into my back bone as she rubbed the sun block into my ass and thighs. When she got to the back of my knees she had to lean forward which made her grind her clit into my tail bone which sent her overboard, she went stiff and let out a long loud moan and soaked my back with her pussy juices.

Once she recovered she finished my legs and by that time it was about 4:30, so we sat down ate some of the sandwiches and had a drank some vitamin waters, and I went about elbow deep in the water and just stared out at the water, then Sam came up from behind me and pushed me and I fell into the water and stayed under and swam around her, came up and picked her up and threw her into the water, the whole time Lynns just back a bit and laughing her ass off when Sam comes up behind her and pushes her over, and she comes up and the two of them get into a splash fight which quickly turns to a two on one against me, by the time we get out of the water its almost dark out so we decide to call it a night.

“Hey Lynn, can I stay over your house tonight? I really don’t want to see my mom after what she did today.” Sam said putting her bikini and clothes back on.

“No, my mom said no sleep overs after what happened last time, sorry.” Lynn replied.

“What happened last time?” I asked

“Wouldn’t you like to know.” they said simultaneously

“Hey Jeff, would your mom let me stay over at your house?” Sam asked

“I don’t see why not, let’s take Lynn home then we’ll go back to my house.” I said

On the way to Lynns house we dropped everything at my house. The walk was uneventful, except a couple of ass slaps and a crotch grope or two. When we got to Lynns house, when she hugged me she shoved her hand down my pants and gave my cock a good hard squeeze, when she did that I shoved my hand down her pants and put a finger into her still wet extremely tight pussy which made her moan into my ear. “Come on Jeff, let’s get back to your house I’m tired.”

The whole way back Sam walked completely topless. When we got back to my house, I made sure to tell Sam that their are three topless girls in my house. “Mom, I’m home. Is it OK if Sam stays the night?” I shouted as I walked through the front door. “Jeff honey, I’m in the bathroom, come here and say that again.” she replied as Sam and I made our way to the bathroom, “I said, can Sam stay the night.” I repeated as we walked into the bathroom to see my mom taking a bubbleless bath. “Yea, sure.” she said waving to Sam and getting up to give me a hug, leaving a wet imprint of her breasts on my shirt.

“Alright Sam, we are going to have to share my bed. OK?” I said leading the way to my room. “Wow, your mom doesn’t care who sees her naked, does she?” Sam said as we got to my room. “No, not really. You should strip down too, its so comfortable.”I said stripping down to my boxers. “OK, but I sleep nude. You don’t mind, right?” Sam said taking off all her clothes, as soon as I saw her pussy my cock started to rise again. “It doesn’t bother me, I also sleep nude. So I hope you don’t mind getting poked a bit.” I said poking her with my boxer clad cock, making her giggle a bit. “You want a vitamin water?” I asked as I walked to the door. “Yea, if you have a focus, thanks.” she said going and laying down. On my way to the kitchen I walked past Jackie, “You should probably do something about that.” she said referring to my cock, I just smiled at her. Once I got back to my room, I took off my boxers and went to hand Sam her drink. when she opened her eyes to grab it she was face to face with my hard cock. “Jeff, I don’t think I’ll ever get over the size of this cock of yours.” she said reaching out and grabbing it and stroking it a few times, getting a moan from me “You should do that some more.” I said with my head back and eyes closed, “What, you mean this?” she said stroking me a few more times. “Yes, that. Keep doing that.” I said thrusting into her hand a little. After that she started to stroke my cock really slow to tease me, after about a minute of that she leaned forward and kissed the tip of my cock, then she started to do that every time she pulled her hand toward her, after doing that a few times, she took my cock head into her mouth licking the slit and underside of my cock head. Then she started to bob her head up and down my shaft, surprisingly taking almost all of it down her throat. giving me a fantastic blowjob. Every time she pulled back she would ring her tongue around the head of my cock, and I could feel her tongue sliding on the underside of my cock. After what felt like an hour I felt that feeling, “Oh Sam, I’m close, keep going, I’m gonna cum. Oh shit Sam I’m cumming!” I shouted a little to loud. As I came I looked down at her, she was wide eyed and swallowing as much as she could, as fast as she could, to no avail, there was just to much cum. Once I finished cumming I looked at the floor below her head and there was a puddle of cum and Sam had a line of cum going from both corners of her bout to her chin. “Damn Jeff, big cock and big loads and your still almost completely hard. I love this thing.” Sam said wipe the cum from her chin. “That was the best orgasm ever, let me return the favor.” I said tearing the blanket off of Sams naked body, and laying down between her legs.

I started by kissing her clit and putting my middle finger into her soaking wet pussy, making her shudder and moan. Then I took long slow licks from my finger to her clit, “Oh god, Jeff that feels so good.” she said putting her hands on the back of my head, pushing me hard into her pussy. Then I took my finger out and shoved my tongue in as far as I could and started to fuck her with my tongue, “Damn Jeff, how did you get so good at that.” she moaned. After about 1 minute of tongue fucking her, she said “Oh my god, Jeff don’t stop, I’m almost there, your gonna make me cum.” while grinding her clit into my nose. I pulled away long enough to latch my lips onto her clit and start humming and flicking the tip of my tongue against it, “OH GOD, I’M CUMMMMMING!” she screamed while her juices flooded out of her pussy, and lapped up as much as I could. “Jeff, that was the best orgasm of my life.” she said after she recovered.

“I want you to be my first, right now. You already broke my cherry, so you technically are my first, but still be gentle, your cock is still huge.” she said pulling me up from her pussy, and lining my cock up with her pussy. “Your pussy is so tight, I don’t know if I can fit.” I said pushing my cock at her hole, then she pushed down and I felt the head pop in and after that the rest slowly followed inch by inch, her mouth was wide open and her eyes were locked on mine filled with love, and stopping me every inch so she can get used to the feeling, and after what felt like an eternity I hit her cervix, making her moan “Oh my god Jeff, you fill me up completely.” while lifting her hips into me signaling I can move, “Holy shit Sam, your so fucking tight, it feels so good!” I said fucking her slowly, “Oh Jeff, fuck my faster and harder!” she moaned fucking back into me, matching my thrusts. “Oh fuck, oh fuck, oh fuck, oh fuuuuuck, Jeff I’m so close to cumming again!” she moaned loudly, “Oh Sam, I’m gonna cum soon, I have to pull out!” I moaned as I started to pull out, “No…. don’t pull out…. I want to…. feel your cum…. inside me…. and…. I’m on the…. pill!” she moaned in-between breaths. “OH MY GOD JEFF I’M CUMMMMMING! she screamed loud enough for the town to hear, as her pussy started to milk my cock, “Oh Sam I’m cumming too!” I said loud enough for my house to hear as I thrust in as deep as I could and started to cum bucket loads of cum deep into her pussy as it milked my cock for all its worth.

“Oh my god.” I said breathlessly as I rolled off of Sam. “Thank you, for being my first Jeff.” she said as she kissed me, “You were my first, too.” I said as I kissed her which led to us making out and her climbing on top of me and trying to coax some life back into my cock, “Lets go to sleep Sam, we’ll go again in the morning.” I said pushing her hand off my cock. “OK.” she sighed rolling over and pulling me into a spooning position, and we both fell asleep almost immediately.