I can't really say my step-sister & I hated each other or even fought like some siblings do, but we certainly didn't always get along. Mom had been killed when I was a baby and when I was 5, dad remarried to Cathy, who had a daughter. I really didn't remember that much of mom & Cathy quickly became my new mom as well as a great wife for dad. Martina was 2 months older than me and figured that meant she knew more than me - about everything. Growing up, we were opposite in most ways. She was fairly tall, slender, long blonde hair, blue eyes and glasses. I on the other hand was shorter, heavier than most kids my age and had short, dark black hair & brown eyes. About the only thing we had in common was that we loved the outdoors - biking, walking, boating, you name it.
I had my first 'steady' girlfriend - Cindy - when I was 16 & it only lasted a couple of weeks - mainly due to my sister. The few times I brought her home after school, my sister would make sure Cindy heard her comments to me: "why would you want a girl with braces" or "why would you want a girl taller than you" or "why would you want a girl that didn't like the outdoors." As you can imagine, that killed that relationship pretty quickly.
I had a few other short-term girlfriends (most of whom I never bothered to take home) and then I met Michelle just after I turned 18. She was new to the college & the more I talked to her, the more I wanted to date her. She always looked like she'd just come out of the beauty parlor - nails, lipstick, makeup, hair - all were perfectly done. When my sister found out I was seeing her, she told me, "I'll bet she's not anywhere near as good looking without all that makeup & likely a tease too.".
We went out for a couple of months, each date we'd go a little further but never 'all the way' and I was grudgingly starting to admit that maybe she was a tease after all - but a beautiful one! There was a yearly event where a lot of us would get together in the bush, camp for the weekend, have a big bonfire, drink and if we were lucky, get some action from our girlfriends. Michelle & I went and I quickly realized she couldn't handle her booze anywhere near as well as I did. Technically we had separate tents but by the end of the night, she was somewhat looped and seemed quite willing to let me do more than just fondle her under her clothes & we ended up in my tent (my tent mate hooked up with her girlfriend and was using her tent). We started making out and eventually ended up lying naked, masturbating each other. I wanted to go all the way but she said she wanted me to go down on her first. I'd never gone down on a girl but between being horny as hell and somewhat drunk I was more than willing.
I brought her to at least 2 orgasms before suggesting that she return the favour - and got a definite "NO!" No problem, I kissed my way back up and got in position to finally have sex with her and was quite surprised to get another "NO!" That started a bit of a fight that finally resulted in me getting nothing more than a hand job before she rolled over and went to sleep. My next surprise was when I woke up the next morning and saw her with her hair all messed up, makeup smeared/smudged/rubbed off & realized my sister was right on both counts -not good looking after all and a definite tease. By the end of the weekend we'd broken up but at least I finally got off with one of the other chicks at the party.
By the time I was 19, I'd finally grown into my weight and was a few inches taller than Martina, bulked up and considered myself quite good looking. I was still attending the local college & I'd had quite a few more girlfriends but much to my dismay, each one turned out pretty much the way that my sister said they would - which pissed me off even more! Martina's usual comment was -- "why do all your girlfriends dress like sluts?"
What could I say? I was 19 and had found that the ones that dressed like sluts were most likely to put out, but I really couldn't tell that to my sister.
The last straw was when I hooked up with Helen - or 'Bird' as she liked to go by. She was pure Goth - black hair, white makeup, dark red lipstick & more than a few piercings. I think the main reason I went out with her was to piss off my sister. Our first date was at the drive-in and before the movie was half over, things were already getting pretty hot in the back seat. Her shirt was off, leaving a very sexy black bra & I noticed a tattoo of a bird on her shoulder blade. When I asked her if that was how she got her nickname she just laughed and said "no, it's a bit of a joke - I got it because I always swallow." It took me a sec to catch on and then wasn't sure if I should laugh or not. She answered my unasked question by unzipping my pants and giving me the best head I'd ever had - true enough she lived up to her name and 'swallow' it was - that time and every time until we broke up. The sex was great, I learned a lot from her and going out with her totally pissed my sister off. Unfortunately sex was all we had in common so after a few months we broke up & she was soon rumored to be seeing one of the younger teachers.
Even so, I was kinda bummed out (as I said, the sex was great) so when my sister gave me the, "I told you it wouldn't work with her." line, it totally pissed me off & I snapped at her, "How can you always tell me what's wrong with my girlfriends when you can't even get a date of your own? You seem to know exactly what I do or don't like but you obviously don't know what you like or maybe it's just that none of the guys like you. Perhaps if you actually wore some clothes that showed you were a girl rather than baggy track pants an a sweatshirt you'd get some attention." As soon as I said it, I could see her lip start to tremble and the tears started. Later I felt sorry but at the time I was so pissed that it really didn't matter how she felt.
Even though I apologized the next day, things were kinda chilly between us for a week or so. I'd pretty much given up finding a relationship for a bit and wasn't really even looking for 'no strings attached' sex. I wouldn't call it a slump -- I just wasn't looking and honestly wasn't sure anymore what I was looking for. That Halloween, one of the guys was throwing a huge party 'cause his parents had gone away for the weekend. I wasn't planning on going but finally gave in to my buddy who kept insisting that even if I didn't hookup with anyone, the beer was cheap.
A couple of days before the party I told Mom & Dad what was happening and they were fine -- I just got the usual "be careful and don't drink & drive!" warning & that they'd be out at his work party that night themselves and had booked a hotel room. My sister seemed interested in the details but to my relief said she had other plans -- at least I didn't feel like I had to invite her along. The party night rolled around and by the time I got there, things were in full swing. I had a couple of beers and checked out the chicks but none really caught my eye. I was taking a break from playing Xbox when I saw a new girl come in -- me and almost every other guy in the place! I didn't recognize her so I figured she must be someone's girlfriend except I didn't see anyone with her.
