When Was Your First Time…? (Part Two)

Carrying on with my lists of firsts (When Was Your First Time…? Part One), in which we have covered some ground already, I’m on to the next big event in a girl’s life; her first heartbreak.

  • My first heartbreak

I will never forget the first time I got my heart proper broken by a boy. It was nothing big, and it was nothing spectacular, but to me, at the time, it meant everything. He was Number 4 and we dated for 2 years. I shall explain a wee bit of the story: I was16, he was obsessed with me, we started dating. We were inseparable. There was talk of him cheating but it was never confirmed. I cheated. I cheated on my Number 4 with my Number 20 – the guy I was dating before. Number 4 was new, and I was still sad from breaking up with Number 20, and when he offered me the chance to spend the night with him, I saw this as a “we can get back together” fuck, (because I was young and didn’t know any better) and we fucked. We fucked in his car, and then ended up sleeping in the car that night because he had been drinking and therefore couldn’t drive. Was it worth it, I hear you ask? No, it wasn’t.

I have kept a journal throughout my life, on and off. Number 4 found the journal and read it, only a couple of weeks from my stupid infidelity and found out that I had cheated on him with my ex. He went ballistic, quite rightly. I think it was his first heartbreak, and I definitely know I was his First Love. He threw me out of his house in quite the dramatic fashion, and threw my belongings out after me, in true Hollywood style. The hurt in his eyes was heartbreaking enough for me, and from that point onwards, I knew I had broken a barrier in myself, as well as him.

Stupidly enough, I have cheated since this occasion. I have either not been found out, or the situation wasn’t quite as traumatic, but when this heartbreak happened, I knew that I was never going to feel that low again for the rest of my life. I had really hurt this guy; I was really horrible. He cried, he shouted, he got drunk, and he hated me. But at the same time, he loved me. This lead to a couple of odd nights – him turning up at mine, (I was living with my Nan) and sneaking in. Spooning me in my single bed, I ended up having my first encounter with angry, hurtful sex. It was vicious, it hurt, we cried, and it was passionate. This was my first time I had ever had sex like that, and although it wasn’t my last, it was still a pungent moment in my life that I will never forget.

  • My first fuck

My first fuck wasn’t what I told everyone. To the girls and boys at school, I had already had sex with a guy that was 3 years older than me at the age of 13. You know how it is – peer pressure and all that. My first fuck was actually with Number 1 at age 14, and it was dramatic! We had fooled around, lying on the floor of his bedroom, doing some serious heavy petting and some hardcore making out. We were going to get dressed and I realized that I was down to my underwear, and we may as well just get on and do it. I believe we had been dating for around 2 months. Off came his underwear, down went mine, and then it happened. His “Banjo String” snapped and pissed out blood everywhere. We didn’t realize – we had never had sex before; how were we to know how “wet” it was supposed to be? We finished and he said he was sore. That’s when we looked down and saw blood everywhere. It was dark and the lights were off, but the red staining on his sheets most definitely gave it away. At first we thought it was me – we both knew I would bleed a little. After closer inspection however, we noticed that there was blood quite literally pissing out of his cock. We had to throw away his clothes that night.

It wasn’t the ground-breaking experience that I thought it was going to be, to be honest. There were no fireworks, there was no real spark, and although we were definitely at it like rabbits throughout our entire 10 month relationship, it wasn’t that good. Funnily enough, he was also my first blow job. I didn’t realize it was coming and he blurted his load right down the back of my throat. I swallowed my first time. What a whore in the making! It made me gag but I didn’t hate it… I am now a great lover of blowjobs.

  • My first anal

I will never forget my first anal. I am still a very angry wee girl about my first anal. I had heard about it, of course, and I was already under the impression that I would probably end up doing it at some point in my life, but at the age of 16, I didn’t realize it was going to be the painful, horrible experience it truly was.

He was a year older than me, Number 20. You’ll recognize this guy if you have read the beginning of this post, and also if you have read “What’s Your Number?” We were drunk at a house party and left the party to find an empty bedroom. We found one. Sex commenced and before long, I was on my hands and knees pushed right into the corner of the bed, which was pushed against two walls. All of a sudden, he pulled out of my pussy and stuck in full-on into my ass. I screamed! There was no warning, no lubricant, and no preparation for this at all! He made my ass bleed; he actually tore me. It hurt more than I can ever remember anything hurting. The inconsiderate bastard had stuck his cock in my ass dry! DRY!!! Do you people have any idea how much that shit just hurts? I still hate him for that. I have done anal since, of course. You’ll definitely know about this (ha-ha!) if you have already read “Anal – What’s the Deal?”

  • My first sexual awakening

You know what a sexual awakening is – that point where you realize you are not an entirely “Vanilla” person. You like things that are out of the ordinary – pain, restraint, stretching, tugging, biting, scratching…. Etc.

I have had many moments of sexual clarity of the years, but I think my first was, again, Number 20. The first time we slept together, I was so nervous. It was in the early evening and it was still daylight outside. I was nervous about taking my underwear off, (Number 1 never took my underwear off when we were sleeping together) so he decided that me not seeing would put me more at ease. Out came the blindfold. This was frightening; I had never had this kind of sex before. He was trying to go down on me, and it was making me nervous because he could see EVERYTHING. I kept pushing his head away, so out came the restraints. He had two ties to hand, and he used these to tie my hands together and keep them out of the way so that he could continue. This was the exact moment I realize that I quite liked bondage. He also gave me my first love of being scratched, especially my back.

To Be Continued…

2 thoughts on “When Was Your First Time…? (Part Two)

  1. I love the idea of first sexual awaking…. I think many people go through life without any kind of experience that “awakens” them. I am just beginning to realize who I am in this way I am fucking 40! What a long time I wasted, eh?

  2. I know! Luckily, I have a few of these “awakening” experiences fairly early on, which I think is the norm these days, with more and more people being more sexually open. I think people are just too scared to think out of the box when it comes to sex… Sad but true. Thanks for your comment & for reading my blog 🙂

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