My name is Oliver, and I lost my virginity late. Back in high school I had always been fairly overweight. I was too nervous to approach girls, and the opportunity to meet anyone sort of just passed me by. I used to get heavy crushes on girls from a distance -- I was too innocent to realise I was being creepy. I would watch from afar, looking at the shapes of legs barely covered by short skirts, or staring at a toned bare midriff fantasising about what might happen if I had more confidence.
All my friends lost their virginities before me, and it wasn't until I was at university that I even made out with a girl. I felt embarrassed about by my lack of experience and was so ashamed of the fact that I had never got laid that it paralysed me. In my first year of university, I had opportunities with women that I thought were way out of my league, but I avoided going home with any of them, because of the potential humiliation of being exposed for my inexperience.
To be honest, upon reflection, at that point I was quite handsome and didn't want for attention from women. My puppy fat that I carried through high school had dropped off and at 6'4" and relatively well built, size, in this respect was not an issue. I didn't realise this at the time though and my lack of confidence definitely put off most women that would make a move on me.
In my second year of university, I moved into a sharehouse with my best friend George and four 19-year-old women. They were all very attractive in their own ways.
Sarah had beautifully tanned skin and perfect body. She had dark hair and eyes and classically stunning features. Though she was incredibly beautiful, she was also very shy and polite. It was obvious from early on that we didn't have any chemistry and so I had no qualms with just being friends.
Sally was a bit of a goth and always took great pleasure overtly discussing her fetishes with the house. She would go on about how she loved to be dominated and all the freaky shit she'd get up to. I'd often look at her long, slender, tattooed legs as they dangled over edge of the sofa barely covered at all by her tiny shorts. To be honest though, in terms of personality, she wasn't really my type.
Alex was too much of a hippy, but had a curvy yet athletic build, with a plump round ass, thick, slightly muscular thighs and well-toned abs. She oozed sexuality and had a high level of confidence, flirting with almost every guy she met -- including me. Though she had a boyfriend, I remember one time her bursting into my room after coming home from a night out. She had just a T shirt and underwear on, and she came a lay beside me in bed. I thought that maybe, this might be my time and feeling her soft body pressed against my back made me rock hard. I knew she could tell that I was aroused, and she shook me and said to me "Oliver... I know you are awake. My feet are killing me, I've been dancing all night. I was kinda hoping you might give me a massage..." I turned to see her smile and instantly she looked down at the tent in my pants then looked back with a knowing smirk. Embarrassed, I obliged and gave her the best foot rub I could muster as I looked up admiring her, but as soon I was done, she gave me a kiss on the cheek, said goodnight, and went back downstairs to bed. This was as close as we ever got to sleeping together.
Ultimately though, it was Charlie that I fell for, and I fell for her hard. From the first time I met Charlie I was smitten. I remember going to meet Alex who was introducing us as potential new housemates. As I approached, I saw her sitting on the bench laughing away and my breath was taken from me instantly. She was quite tall and had a devilish smile, full lips, and big round eyes. Her long blonde hair fell down below her shoulders. When she smiled at me and looked into my eyes, I melted. I tried hard not to look her up and down too much as we introduced ourselves, but as soon as she wasn't looking, I couldn't help myself but check her out. Her body was toned with soft, fair skin, a thin yet curvy figure and long model-like legs. It was also impossible to not notice her incredibly large and perfectly round breasts, which stood out in the skin-tight jumper she was wearing. That first time we hung out she made me feel so at ease. She was so warm, funny and kind and I could feel myself falling harder and harder as we teased each other and laughed away that afternoon. When we parted and said goodbye, she gave me a long, close hug and as I felt her huge breasts pressed against me, I did everything I could to contain myself. From that moment she was the only girl I ever fantasised about, and I did, often.
