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 altındağ escort 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.
Unfortunately, after we moved in together, I found out she had a boyfriend, Ryan, and he was an arrogant piece of shit jock. He was not as tall as me, but very obviously attractive and clearly spent a lot of time at the gym. I was so envious every time they hung out together at our house and I don’t think I did a very job hiding this from them or my other housemates. I’d watch her kiss him and run her hand over his huge biceps and just think to myself about how much I wanted to hit him. Looking back on it, I was pathetic and was humiliating myself. Boy did I have no idea how far that theme was going to go.
Charlie quickly became comfortable enough with me to tell me everything about her, including her relationship. I don’t know if she was aware of how obsessed with her I was, but I clearly liked her, and she had very clearly friend zoned me from the get go. Naively though, I let myself stay in denial about this, firmly holding on to a glimmer of hope that if she got to know me well enough, true love would shine through. I confided in her emotionally in ways I’d never let myself do before and I could feel the level of intimacy between us reaching a point beyond where most friendships go.
Some of the conversations were getting rough though as we got closer with each other:
“Look, I know Ryan’s kind of an asshole, but he’s actually really sweet to me and he just makes me feel so good!” Charlie said to me as she lay back on the couch with her head resting in my lap. “I can’t help it. I don’t really care what he’s like to everyone else. ankara anal yapan escort I know he’s rude to you, but Oliver you have to understand… The way he treats me like a goddess, yet at the same time, when we are in the bedroom, he completely owns me — it makes me hot just thinking about it.”
“Uh huh…” I said in return, trying my best not to come across as the jealous loser I was.
“Yeah. And he has a huuuge dick.” She said whilst smiling at me and holding her hands apart about a foot to emphasise his length. I swallowed awkwardly loudly. “Yeah, I didn’t realise how much I needed that until I slept with him, but it made everyone before him fade away to nothing. Like, wow!”
I had never really thought about my size until that conversation. I had always thought that I was about average, but my shyness and virginity had been a bigger worry. After that though, I couldn’t help but wonder how I’d measure up.
Making matters worse, we shared a bedroom wall and I heard them having sex a lot. I often jerked off as they were going at it. Hearing Charlie moan with pleasure was just so hot and I couldn’t help but fantasise as a result.
One night, when I could hear them starting, I decided to sneak a peek at the action. I snuck out of my room quietly and crept up to her bedroom door. I tried to glance through the keyhole, but couldn’t see anything, so, with my heart in my mouth, I turned the doorknob as gently and quietly as I could, hoping they wouldn’t be looking as I pushed it open a crack. Thankfully, they weren’t facing the door completely as Ryan pulled off her top. I watched, amazed at how perfect Charlie’s body was. Those huge, full, perfectly shaped white breasts were gobsmacking. They were the most incredible pair of breasts I had ever seen, even including in porn and on TV. They were emphasised by how slender and toned her body was and they had cute, round pink nipples which were perky and even. As I watched Ryan slowly pull down her panties I got my first glimpse of her gorgeous pussy, completely shaven and with slightly swollen but elegant, innocent looking lips. I could see small droplets of wetness coming out as he pushed two of his thick fingers inside of her. Charlie made a whispered moan in response.
She turned to face him — away from me at an angle — and unbuttoned his trousers. Looking at him, I had to say he was a total hunk. His toned chest and abs and huge biceps were impossible to ignore and though his tattoos were cheesy, overall, I could see why women liked him. Then as she pulled down his underwear, I saw his massive cock. Charlie hadn’t been lying. In its semi-erect state, it was at least 7 inches long and extremely thick. She wrapped her hand around it, and as I watched it grow, I could see that she couldn’t fit the whole way around its girth anymore. The precum that was lubing it up highlighted its thick veins. I could feel my own dick getting hard and I reached down to feel it. I thought “it must be half the size, if that…”
As Charlie bent down and wrapped her lips around it, I started to feel my mouth watering. It looked juicy and meaty ankara escort and I thought to myself, “geez is his cock actually turning me on?” I licked my lips a little as I watched her try to fit it in her mouth, looking at up him with those big eyes. Her full, soft lips were sucking on the tip of it and, fully hard now, he grabbed her head with his strong hands and with gentle, yet intentional force pulled her mouth further along his huge ten-inch monster. Charlie looked uncomfortable, with her eyes wide and beginning to water, but as he pulled her back and forth, gaining rhythm and thrusting slightly, it looked as though she was getting used to it. Then with one firm thrust he forced the entire thing into her mouth and down her throat and held it there for a several seconds before letting her go. Charlie coughed and gasped and spat ropes of precum from her mouth. She looked shocked and slightly dizzy, but her eyes were filled with lust.
Ryan then grabbed her and spun her around, pushing her forward so that she was knelt on all fours. He started stroking his huge cock as from behind he brought it near her wet pussy and slowly pressed its huge veiny head against her opening. I could see her beautiful pussy start to stretch apart and hug the tip of his cock, almost looking like it was trying to suck it inside of her, whilst at the same time not being able to fit it in. Then he pushed it in a little further and as her pussy stretched open Charlie moaned loudly “oh fuck yes!”
Ryan grunted as he began thrusting very gently. I watched in awe as this chiselled meathead pushed his huge veiny cock in deeper and deeper. I could see the expression of pure ecstasy on Charlie’s face as he fucked her harder. Her tits bounced and slapped against her chest as he pounded against her. I looked at the muscles of her long sweaty legs tense and move as she tried to match his rhythm. He kept going faster and faster, deeper and deeper. I looked on in awe as the entirety of his thick, manly cock, went all the way in and then almost all the way out again and again — shining and glistening as Charlie’s pussy continued to swell. After several minutes, with both of them covered in sweat, Charlie started screaming and writhing in what I could only assume were a series of intense orgasms.
I was so immersed in what I was watching that I had forgotten to pay attention to my own stealth as I masturbated and just as I realised how carried away I was getting, Charlie suddenly turned her head and made direct eye contact with me. I must’ve looked like I’d seen a ghost as I embarrassingly shot my shameful load into the bottom of her door and looked down in panic as I sobered in its wake. She looked at me confused, slowly realising what was going on and I quickly closed the door and quietly scurried away, my heart racing like a frightened animal.
“Oh my god. What have I done? What have I done?” My thoughts raced over and over as I lay in bed. “How on earth am I going to face her in the morning? Is she going to tell everyone? Did Ryan see?”
As I lay there shaking in fear, I heard them start back up again. Charlie screaming out “Oh fuck Daddy, fuck me! Fuck my pussy deep like that! It feels so good!” and the cacophony of the bed creaking and shaking filled my room. I reached down and felt my hard little dick. My heart sank as I looked down at it, realising it was increasingly unlikely it would ever fuck her – certainly not like he could.
To be continued…