Educating Gary Ch. 01

I figured things would change some in my life when my mom remarried. I just didn't think my life would take a total 360. The things I would experience thanks to my new step-sister Katie still shock me some to this day. But I will start from the beginning. When I was 18 my mom got married again to a rich businessman this time. He was a nice guy and could provide us with things we needed so I didn't mind my mom marrying him. The best part to me though was my new step-sister Katie. We had gone to school together for years but we didn't really run in the same circles. She was one of the most beautiful girls in school and was very popular, but I was average in about every way possible. Katie and I got to know each a little while our parents were dating but not much. They got married a few days after we had graduated high school and I moved in to her father's large home right before they left for their honeymoon. Katie was gone the entire day I was moving in, probably out partying or getting fucked.

She had a reputation as being a party girl who didn't mind putting out. I had heard some stories about her ranging from her being bisexual to her being involved in gangbangs. Not that I was against getting screwed up and going to parties and getting laid, but I wasn't very popular with the ladies I guess, in fact I was a virgin when I moved in with her. I heard Katie arrive home around 4AM that first night I stayed there and stumble into bed. I woke up the next morning and explored all the new things I could do in my new home. I started off by taking a swim in the huge pool they had in their backyard. The cabana out back had a bunch of Katie's string bikinis spread out across the floor. I had imagined what her smoking hot body looked like in the bikinis and without anything on at all. My biggest hope moving in was that she walked around in little clothing all the time and that I might get to catch her naked a few times. After taking a swim I dried off and went inside to watch some TV in their living room, which was more like a movie theater than a living room with all the gadgets and other things they had.

Around noon Katie finally woke up and strolled past the living room. I guess she didn't even remember I was moving in as she walked by in just a tight white tank top and a pink thong showing off her amazing heart shaped ass. I was instantly hard as my cock sprang up in my gym shorts. She walked into the kitchen and grabbed a bottle of water. As she passed by the living room again she gasped and almost spit out the water she was drinking as she was shocked by my presence.

"Oh god you scared the shit out of me, I forgot I had roommates now." She said while looking me over.

My eyes locked on her amazing body as I tried to focus and respond "Yea umm sorry, I moved in yesterday while you were out."

Katie smiled and said it was fine as she strolled over to the couch and sat next to me. She stretched out and gave me a nice view of her curves before plopping on the couch. Her head turned down to see the erection in my pants and she smiled.

"I hope you don't mind my attire, I tend to walk around in my panties and bikinis and sometimes naked even cause I'm usually home alone." She said with a devilish grin on her face knowing the effect she had over me.

"Oh no its fine I don't mind at all, you don't have to change your ways for me." I responded sounding like an idiot to her probably, but I tried to change the subject quickly. "So do anything fun last night?"

"Went to a party with a bunch of people from school, got wasted, and umm...you know got a little naughty." She said while laughing and patting her thong covered crotch a couple of time.

"Oh right on, sounds like a blast." I said in jealousy, wishing I could get a taste of her.

"Why don't I ever see you out at any parties Gary?" Katie says while turning towards me as her bare legs begin to rub against mine.

"Well you know I guess I'm really not part of that crowd, my friends tend to lay low, not exactly part of the cool crowd like you." I faked a laugh as I answered, knowing I sounded stupid.

"Well how about I start bringing you out with me, I'm sure you'll fit in well, plus you're my step brother now so everyone will like you." She said with a big smile as she placed her hand on my thigh. I was still horny as hell and she could tell as she kept looking down at my crotch.

"Yea that sounds great, I'd love to sometime." I said while my cock ached for release. I wanted to run off to the bathroom to masturbate, but I didn't want to make it obvious so I stayed seated next to her.

"Good, plus I bet you will get tons of pussy, I'm sure you are a ladies man." She said making it painfully obvious she didn't know me.

"Not really, I don't do to well with the ladies." I said shamefully to the hottest girl from school that was half naked.

"Aww really? How many girls have you been with?" She said putting me on the spot.

"Well I've gotten a couple of blow jobs and stuff but...umm...I've never had sex." I admitted to her the embarrassing truth, that I was an 18 year old virgin.

"You're a virgin?" She shouted out while giggling. I turned red and nodded shamefully. "Oh I'm sorry I didn't mean to laugh, I just figured that since you were so cute you would have banged one of those loose whores we go to school with." She said trying to make me feel better.

"Yea I wish, I'm working on it, but so far no luck." I replied wondering how much worse this conversation could get.

"Hmmm...well you don't want to go off to college a virgin do you?" I gave her a quick no, a little annoyed by her stating the obvious. "Well Gary how about I train you to be a pro?"

I turned to her confused and wondering what she meant. "Gary, I want to take your virginity and turn you into a sexual god before you go off to college, if you do what I say we both will have a lot of fun and you will have the confidence to bag any girl you want."

I was in shock. I didn't know what to say. Her hand was now rubbing my cock through my shorts as she smiled and licked her lips. "Ummm yea sure Katie if you want to...I would do anything to fuck you." I blabbed out, she laughed and nodded.

"Good, we will start tonight, first though we need to prep you." With that said she got on her knees and pulled my shorts down and let my cock spring free. She took it in her hand and looked me over.

"Mmm nice looking cock. How big are you?" She said with a playful laugh.

"Like 7 inches long I think, I'm not sure about how thick." I answered hoping that was big to her.

"Not too shabby, looks like you got some nice thickness on there, but you are a little hairy for my taste. Shave your crotch and balls while I'm out. I'm going to run some errands and get some party supplies. Tonight we will start your training, don't you dare jack off while I'm gone either." After that she tucked my penis back into my shorts and went to her room. After she changed into a short jean skirt and put on a t-shirt she got into her car and left.

I did as she said and headed to the bathroom. After showering I shaved my pubes, making my crotch, cock, and balls hairless and smooth. I liked the way it looked and felt as my anticipation for her return grew. I wondered what she had in mind for my training, as I hoped we would have sex tonight so I could finally lose my V card. After cleaning up I got dressed in Khaki shorts and a polo shirt and waited for her return by watching TV. Katie returned a few hours later with a couple of grocery bags, and a couple of shopping bags from the mall. After she put her things up she said she was going to make dinner for us. We ate dinner together, drank some margarita's, and made small talk as I was nervous and excited the whole time for the fun to start. After we cleaned up the mess from our meal she came and sat on my lap on the couch.

"So I feel like taking a little swim, so let's get naked and take a dip" She then kissed me as I embraced my new step-sister and felt her soft plump lips take me over as her tongue slid in my mouth. Katie then popped off my lap and led me out back. As we got outside she lifted her shirt over her head and pulled her skirt down her long smooth legs. I stood there and stared as she smiled and continued to strip removing her pink bra and matching thong. Her body was perfect, like something you only see in magazines. She was toned and had perfect curves without a tan line on her.

Her perky 36 C breasts were matched with hard pink nipples the size of a quarter. A flat stomach led to skinny hips that arched out with an amazing heart shaped ass. She let her hand slide down her stomach all the way to her shaved pussy. She bent over and gave me a show as I saw her tight pink pussy glisten in the lights by the pool.

She walked over to me knowing I couldn't move and began to undress me. She removed my shirt and shorts and let my rock hard penis spring free again. She told me I was a good boy for shaving as she rubbed my cock before guiding me to the pool. We jumped in as she swam a few laps around me, like a shark waiting to strike. She splashed me a couple of times before telling me to come and get her. I chased after her dying to get my hands on her until she led me to the shallow end. She pushed me against the edge of the pool and we began to kiss again. I wrapped my arms around her as I felt her soft wet skin in the pool. My hands dove for her ass as I cupped her soft curves and she wrapped her legs around me. A small moan came out her mouth as her pussy grinded against my cock. I then pulled a hand up to feel her luscious breasts as she began to kiss my neck, I whispered in her ear that I wanted to fuck her. She broke off of me and walked out of the pool as the water dripped off of her amazing body. I followed and we dried off outside. We wrapped towels around ourselves and she led me to her room. She ripped our towels off and pushed me on the bed and mounted me.

"Now it's time to start your training Gary. Tonight we will start with taking your virginity. Now I know you said you've gotten blow jobs before but no one sucks a cock better than me"

She then slid down and took my hard cock into her mouth. She sucked on the fat head of my penis at first before taking her tongue and running it up and down the shaft. After coating my cock in her saliva she took my dick and began to slide into her mouth, taking it in inch by inch before all 7 inches of my dick was buried in her throat. I arched my head back and groaned as I was having the greatest experience in my young life. Her mouth was bobbing up and down on my cock as it disappeared in her mouth. She pulled my dick out of her mouth and then stroked my cock and began to suck on my balls. I told her I felt like I was close to cumming so she stopped.

"You aren't blowing that load just yet" She said with a smirk. "Now get up, it's time for you to learn how to give a girl oral. This is very important so do what I say."

I took her orders and got off of her bed. She then lamed down and spread her legs to invite me in. It was a beautiful sight as I finally got to take in a girl's pussy. Her labia looked a little swollen, probably because she got fucked the night before, but I didn't care. I leaned in and could smell her sweet musk. I took my hand and began to rub her pussy; the feeling of her warm wet snatch was overwhelming. She took her fingers and spread her labia for me. She pointed out her clit to me and told me to start licking. I dove my face in and began to lap at her hot pussy; the sweet taste had me in ecstasy as I licked her and nibbled at her. She then told me to focus on her clit, so I did as she told me to and flicked her clit with my tongue while working two fingers in and out of her. She moaned for more as I kept at it and sucked on her clit until she let a scream out that she was cumming. I felt a sense of pride as her hips bucked into my face that I had made a woman cum. I continued to eat her out for a couple of more minutes until she pushed herself off of me.

She got up and kissed me as she licked her own juices off of my lips. She smiled and stretched her body out as I began to realize we were finally going to have sex soon. After making out for a few minutes she placed me back on the bed.

"Now usually I make most guys wear condoms with me unless I know them very well. But since it's your first time I'll make it special for you and let you go bare. Don't worry though I'm on birth control so we won't have any problems, and I'm clean and tested." She proclaimed as I laid back and she began to stroke my cock quickly making it hard as a rock.

"Ok babe it's time to lose your virginity. Now take it slow with me at first and don't be nervous or over think about it. Just keep stroking it in and out until I tell you to go harder." She demanded as I got between her legs and she guided the tip of my cock inside her pussy.

I gasped as the sensation overcame me. I finally was having sex and it was with one of the hottest girls I've ever known. I was in heaven as her tight pussy slowly took in my penis. She moaned as she reminded me to slow down. I began to create a rhythm as she moaned out that she wanted it harder. I followed orders and began to thrust in and out of warm pussy with some force for a minute or so before I felt my balls tense up and I knew I was going to cum soon. I tried to slow down the pace but she grabbed my hips and demanded I fucked her harder. After a few more pumps I told her I was cumming as I made a final deep thrust into her pussy and shot my load deep inside her. She wrapped her legs around me and held me tight as my cock twitched from the after effects of my orgasm inside her pussy. My dick began to get soft as I felt our juices flow out of her, and I pulled out and laid next to her.

"So how was losing your virginity Gary?" Katie asked while she wrapped her arms around me.

"It was great; I can't wait for you to teach me more." I replied with the world's largest smile on my face.

Katie then reached down to her pussy and grabbed a taste of my creampie "Mmmm that's good, because I am going to show you some things you may never dreamed of doing. But I'm exhausted so let's get some sleep babe."

With that we closed our eyes and fell asleep together. I replayed the night in my head and wondered what else I would experience with my new step-sister.