My Sister's Keeper

By SunshineDaniels

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Tags: sex, first time, virgin, losing my virginity, lust, love, erotica

Added: 15 Jul 2009 Views: 40539 Avg Score: 4.79

I lost my virginity to my sister's boyfriend, read all about it.

Jane was off to college at Boston University.    I was a senior in my high school, which in the back woods of Maine consisted of grades “K through twelve”.   I dreamed of someday following in Jane’s footsteps and going off to a big city, and leaving this North of Nowhere town.

Maybe I was naïve, but my life was going nowhere fast.   I grew accustomed to small town antics and choose to swim nude in a stream rather than attend my classes.   Although I was very talented, my grades were a mere reflection of my boredom and lack of attendance.   I would often slouch around in sweats and an old T-shirt, though I had grown into a very pretty eighteen year old, and would often find the likes of the three single boys in town glaring at me--none of whom I was remotely interested in.   

Jane was tall and slender with dark hair.   She was a bookworm and perhaps some would say she was ordinary. I always thought her outgoing demeanor made anyone want to know her.   She was smart, and wanted to be a Marine Biologist.    She never had a problem conversing with people.   She used to email me regularly once a day or every couple days when she went off to college.   This week I grew worried when her emails stopped for a well over a week.

Just when my parents were ready to jump in the car for a trip to Boston to check on Jane, (which I was so excited about) the emails started again.   Darn. It appears Jane had met someone, and they were dating.   Leo was his name and he was from New Jersey.    For the next few months it was Leo this and Leo that.    Until one day several months later, I read her latest email.

Dearest Magpie,

I’m tired of telling you how great Leo is, so this weekend you can meet him in person and see what you think.   We are an official item now and I’m bringing him home to meet the folks.   Get my room ready.



My name was Maggie but she would always call me Magpie, which I hated.    I had only one day left and then Jane and Leo would arrive.   I cleaned her room and set up some blankets on the couch, as my father was adamant that Leo would sleep in the unused family room.   Our house was large and old, and I wondered if Leo had seen anything like it before.   Certainly a big city Jersey boy would think we were paupers.

A few hours before they were to arrive, I decided to wear some of my clothes that I had gotten for my birthday.   The baby doll t-shirt was a little snug as my breasts had grown, and the denim shorts a little short as I grew somewhat taller.   At 18 I was still considered short and slim, with blonde hair and very large breasts compared to others.   I was much prettier than my sister, but didn’t try to be.   My eyes were green and today I styled my hair and applied some make up and toe nail polish to make the best impression ever.    When I glanced up, I hardly recognized myself—I looked so different than I did in slouchy sweats.  

The doorbell rang.   I ran down the steps and while everyone was exchanging hellos, my sister grabbed me.   When she went to introduce me to Leo, I spun around and was in awe.   Standing in front of me was the most handsome man I’d ever seen.   A strong, muscular Italian with a beautiful smile and eyes stood in front of me.   Soon he was hugging me saying, “It is so very nice to meet you Maggie.”

I forced a smile and told him, “Likewise.” I took my sister’s bags up to her room.   She followed me quickly and said, “So, what do you think?”   I spun around and I said, “You did good, you did really good.”

Over dinner I couldn’t help but exchanging glances with Leo who always seemed to be staring at me during his story telling.   I asked him to tell me all about New Jersey, which prompted a long dinner conversation.   As I was watching his lips move I tuned out the words, lost somewhere in his story I drifted off and imagined him kissing me with his luscious lips and yearned to see him naked.   I was undressing him with my eyes and I wondered if he could feel me looking at him.   Once I think I caught him staring at my low cut T-shirt in between chews.

Quickly I jumped up after dinner to do the dishes and clear the table and Leo insisted on helping. “Please, I’m guest and the least I can do is earn my keep.”

He followed me to the kitchen carrying dishes while my parents and sister whispered in the dining room.   Leo asked, “Shall I wash, or dry?”   I told him I would wash and he could dry.    While doing this, he told me a story about his grandfather and him on a trip to New York from Jersey, and how they got lost in a bad part of New York City.   I found myself laughing often as he was a very good story teller.

My hair fell into my face as I was washing dishes and my hands were soapy.   I felt Leo take his fingers and push my hair back off my face.   Our eyes locked and we held this gaze for more than a minute.   In this instance my body was trembling, there was a tension between us but I was not sure what.    I quickly looked down into the soapy water, and changed the conversation.   “So when are you marrying my sister?” I joked.    Leo laughed and said, “Whoa, slow down. Can I make it thru the ‘M eet the Parents’ weekend first?”

After dinner I went for a walk by myself, trying to get some fresh air.   I told myself that it was wrong to think such things about my sister’s boyfriend and after several hours headed back to the house.   Leo was sitting outside by himself.   He spoke, “I thought you’d gotten lost.”   I smiled, “No, I just needed some fresh air.”   He said, “Me too”, and followed me inside.   I turned around to see him staring at my ass.

My sister was already in bed, exhausted from the car ride.   My parents were going to bed which left me entertaining Leo.   I wanted to retreat to bed as well, but Leo insisted on telling me stories and asking a lot of questions about the town in which I lived.   We shared a lot of stories that night.   Oddly he asked nothing about my sister and when I grew inquisitive, he just stated that they had been dating awhile and were seeing where things were going.   I told him I had never dated anyone, and he seemed astonished.   Leo replied, “You are a gem hidden deep in these woods.   Like a diamond in the rough.”  

Soon we were making Jiffy Pop and watching an old scary movie.   We had a great time and I didn’t want to go to bed.   I was so happy to have someone around whom I could have an intelligent conversation with.   Soon I found us talking about everything and anything and caught myself nodding out on his shoulder and quickly apologized. I only woke up because he was caressing my face.   How embarrassing.   I apologized and quickly ran up to bed.

Saturday flew by as we took Leo on the lake fishing all day, as a family gesture.   We all had a great time.   Leo wanted to go swimming but my sister was not a water lover, so I was again volunteered to swim with Leo.   I removed my tank and shorts to expose my bikini, and instantly I felt Leo staring at me.   I must admit I was in shape thanks to all the walking and hiking I did and my breasts barely fit into my bikini top.  

When Leo took off his clothes down to his boxers, I quickly had to jump in the water, holding my breath and sinking down into the lake.   If not I think I would have attacked him as his stomach was cut and his chest so beautiful, it was apparent that he worked out often and he was driving me crazy.

My sister and parents were fishing and told us to swim to the shore as we were splashing and carrying on, so we would not scare the fish.   It was only thirty feet away so we did just that and climbing up on rocks we made our way to the small island full of pine trees.    I started to walk into the brush and Leo was yelling, “Hey, wait up, where are you going?”   I said, “What’s the matter Jersey boy scared of a little forest?”

I ran and he followed and soon I found myself tripping into a chipmunk hole and tangled up in a tree branch, it had pulled my bikini top to the side and left one breast exposed.   Leo walked in front of me staring at my breast smiling, “It looks like you are the one who should be scared of a little forest!”  

Leo gently removed the branches from my bikini top and attempted to move my bra back over my breast.   He stopped and I saw his hand shaking.   I wanted him to cup my bare breast and soon I felt my nipple hard.   He was frozen staring at my nipple then looked at me intently.   “Why are you so damned beautiful Maggie, I can barely keep my hands off of you.”   

Just then he cupped my breast and pressed up against me, pushing me against a tree trunk.   I felt the bark burn into my back as he kissed me passionately and I felt his cock growing large against my body.   I   felt him rubbing my exposed breast and pinching my nipple.   I soon felt my cunt growing wet and I wanted him to touch me all over with his mouth.   My whole body was shaking and I was moaning and I ran my hand down his chest, down to his belly button where I could feel hair starting.   I longed to follow it, and I pulled the stretchy material on his swim trunks down.   His cock was large and beautiful, and I bent down to kiss it all over.   First I kissed the head, and then I kissed his balls.   I began sucking on his balls and then his cock, taking turns.   Just   then I heard my sister calling and like a shuddering nightmare, I awoke.

I pushed Leo away and ran back to the tiny beach with Leo following me.   He said, “Please, Maggie, wait.”      I fixed my bikini top along the way and waved to my family while approaching the shoreline. I began to swim back with Leo behind me.   My sister had screamed with excitement as she caught a fish and I felt as though the only thing I had hooked was her boyfriend.

Dinner conversation Saturday night was minimal, there was a tension in the air between Leo and myself, and try as I may to not think about what had happened it was just about all I could think about.    My mother and sister were cleaning the fish and Leo was being quizzed by my Father about his family and intentions with Jane.    Leo answered truthfully that they were taking things slow and there was no need to rush into anything.   I thought about his cock being in my mouth just earlier that day and had to excuse myself from the table.

I was relieved when Saturday night Leo and Jane went to a drive in movie by themselves, and as I waved goodbye to them from the front door, I shut it before I could see Leo turning around to look at me. I went to bed early in hopes my weekend would fly by.   Instead, my sister woke me at Midnight to tell me all about the movie and her date with Leo.   She told me that she was trying to kiss him and touch him down there, but she said he was tired and not responding.   She was upset that they didn’t’ do it.   I assured her not to worry that Leo was most likely tired from the day on the lake though she tried her best to have a good time with him.

At two in the morning I had to use the bathroom, so I crept down the steps so as not to wake Leo.    After a short tinkle, I opened the door to see him standing there in briefs.   His body was rock solid and so inviting.    I stepped to the side and walked around him but instead of entering the bathroom he spun me around and whispered, “Maggie, I can’t get you out of my mind.   I haven’t slept a bit.”

I felt guilty and excited all at once.   I couldn’t let myself make another pass at my sister’s keeper but I wanted him so very much.   I suppose he read it in my eyes, as I thought to myself how much I wanted to feel him inside me.   I was a virgin and something about him made me feel comfortable yet aroused at all once.   From the looks of his eyes,   he was thinking how nice it would be to fuck me, and fighting with his obligation to my sister.   There we stood the wolf and the fawn, no one moving, no one saying a word.   I am sure we were both too scared to do anything, and I felt my pussy swelling with wetness and aching for him.     I wonder how many times he had my sister and if I was just a conquest for him.

Finally I had an idea.   I pushed him towards the wall and held a finger up as if to say “Stay there”.   I pulled my pants down and began to masturbate in front of him.   I figured if I could play with myself, it wasn’t cheating.    He pulled his cock out and followed my lead.   He stroked his head up and down, and I watched it grow.   I wanted to feel it inside my pussy but I knew that would be again crossing the line. I used my fingers to rub my clitoris and enter my vagina thinking of his cock.   His cock was now huge and bulging and I was scared of it, but I rubbed my pussy and thought of it anyhow.   Soon I began to moan quietly and tremble and shake and I saw a look of satisfaction on his face as he squeezed his cock and it exploded all over his underwear.   We stood in the hallway panting; we had just come together, fantasizing about each other.   All the while we were still worlds apart and that’s how it would stay. Or, so I thought.   

  I had planned on sleeping late but was ripped out of bed by Jane, who begged me to stay with Leo while her and my parents attended church.   To make matters worse, they would be late today as two neighborhood kids were getting communion.    I was the one who never went, and so it was I that had the ill fate of yet again entertaining Leo.   I snuck down the steps and Leo was still sleeping.   I got a hot shower and went into the kitchen.   I heard him use the shower, and soon I felt his stare on my back.   I spun around, wet, and wearing only a tank top and shorts.    I figured without the makeup I would be less attractive to him, and maybe he would think twice about doing anything today.   He said, “Good Morning Maggie. Where’s everyone?”

I told Leo they were at Church, and would be for a few hours.   I saw the look of horror on his face.   He said, “Maggie, we need to talk.”   I looked at him and jumped up on the counter to sit and listen to him.   “What is it?” I asked.

“I can’t do this; I can’t pretend I don’t feel anything for you.   I am supposed to be dating your sister but what we did last night, I mean what I did last night, was so hot, I want to be with you so bad. I can’t hide these feelings, there is some kind of connection between us Maggie, do you feel it?”

I sighed as I was not a good liar.   I responded, “Yes, I feel it.”

Silence became us as he stepped closer to me.   As I sat on the counter, he approached me, standing in between my legs.    Leo said, “Then let’s clear the air of this tension.”

Soon Leo was kissing me passionately and I felt my nipples growing hard.   His hands were groping my nipples and he ripped off my tank top, kissing on breast gently then the other.   He used his teeth and teased my nipples, until I moaned with enjoyment.   He slid his hand up my shorts and moved it to feel my wet pussy.   He began rubbing my clitoris which felt better than if I were doing it myself.   I moaned again as his mouth sucked on my tits and his fingers probed my vagina.  

He reached back and grabbed a chair, and pulled it close, sitting on it.   I was unsure what he was going to do, but then he ripped my shorts off me, and pulled me to the edge of the counter.   He pressed his face into my wet pussy, and I was in shock.   Not only had I never had sex, I’d never had sex like this.   I was nervous and excited all at once.   His tongue probed my pussy as he lapped up the wetness.   Soon his tongue was making circles on my clit and his teeth gently biting me.   I felt myself start to tremble and shake, I grabbed his face and held it close to my pussy.   I was ready to have the biggest orgasm ever, right in his mouth.    Just then he reached up and pinched my hardened nipples, and I felt myself come into his mouth.   I tried to wriggle backwards but he grabbed my ass and pulled me towards his face, burying his head deeper into my vagina.   I continued to come and was throbbing all over, I think I came twice, it was a blur as it felt so good and took all of my energy.  

He stood up and I could see his mouth was all wet. “You taste so good”, he told me.   Just then he stuck his hard cock into my already throbbing pussy.   I began to quiver.   I wanted to tell him I was a virgin, but he found out soon enough when his cock would only go so far in.   I felt like he was hitting a wall.   “Shhhh” he said when I attempted to talk.   He gently pulled his cock in and out of my pussy, pushing it harder with each thrust.   I was still in ecstasy and when he finally broke through I thought I was in heaven.   He fucked me for awhile like this, then carried me into the couch and made me get on all fours.

From behind he entered me and slapped my ass.   He then turned me over and kissed me gently, and made love to me on top staring into my eyes for what only seemed like seconds.   When he was ready to come he asked if I would swallow it like he did mine.   I did just that, almost choking on his cock and heavy load. We collapsed together on the couch, wet, and sweaty.  

Just a half an hour later, we were doing it again.    I could not get enough of his cock.   Soon our fun came to an end when my sister arrived home from church.    I know I should have felt guilty about being with my sister’s boyfriend, but I didn’t.   It was too good and too hot.   I was just so happy that my first time was so erotic.  

Needless to say soon after returning to college Jane indicated that Leo and she had broken up.   A few weeks later she was dating a guy named Jeff and head over heels.   I was thankful that she was over Leo.   My doorbell rang a week after that, and it was Leo.   We’ve been together ever since and the sex just keeps getting better.  

My sister never knew that he took my virginity, until now.