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The Odd Sexual Encounters Of Anthony Bay – Age 17: Losing It

At the age of seventeen I was in the middle of my latter years of high school. Over the course of the year loads of guys and girls had been losing their virginities, it wasn’t fair. I didn’t have a girlfriend, my last one dumped me on the spot when I merely mentioned sex, and some girls you only had to ask and she’d have sex with you! I didn’t resort to them for several reasons. 1: Only desperate and more popular kids got them. 2: They were so slutty it didn’t really count having some whore take your virginity. 3: One nerdy kid tried his luck with one and she had him suspended for sexual harassment. So, although these girls were hot, there were only about two of them who did it willingly. I thought I was safe amongst my circle of friends, until one day Scott came in with a huge grin on his face saying he’d done Sadey Cullingan.
“What?!” I cried in disbelief. They’d only been going out a couple of weeks I assumed she’d do what my ex-girlfriend had done.
Scott, Jeff, Dan, and I are kind of standing in the wide chasm between cool and unpopular. We get invited to all the parties within our division, some of the ones amongst the geeks and nerds (some thought we were to cool to invite which is kind of sad because I don’t consider myself particularly popular) and occasionally the big parties in the upper division. These are where the sports players, cheerleaders, and generally anybody who was able to impress the people who were at the top previously. I was perfectly happy, I had good friends and never made any major social blunders, I like to think that anyway. None of the Bully’s ever bothered me as I had an old mate—Alan Tunnel—who is the biggest, if not the best, football player on the team. I knew that he would at least stand up for me if I ever got beaten up.
Back to the virginity situation. The general custom when someone in high school lost their virginity was to bring back the girls panties as proof that they’d at least got them off her. A Baseball player, Tommy Gray, who spent most of his time on the bench had even got a signed bit of paper from one of the sluts which I think was little sad, for most it was the custom to bring at least one item of clothing back as proof, or if it seemed incredibly unlikely, a photo, the contents of the photo depended on how far up the social hierarchy you were. If a nerd were to claim he’d had sex he does probably have to show off one, if not more, pictures of him inside the girl. If I were to claim I’d lost my virginity I’d only have to have a picture of me getting her clothes off, or, for those in denial, me getting boob or oral, but for my closest friends I could get away with panties. Someone like Alan Tunnel however only had to say he’d had sex and you’d have to believe him, no smart popular person would risk their position by lying, although most had a habit of bringing back lingerie as a ‘prize’.
I turned my attention back to Scott “how the hell did you get Sadey Cullingan to fuck you?”
“You remember that semen they found in the sink last week?”
“Yes” Jeff, Dan, and I replied in unison, hanging off his every word.
“Well she didn’t want me jacking off” Scott was leaning against a dusty brick wall with a smirk on his face “so she decided we ought to have sex so I wouldn’t lose interest”.
“Bloody hell!” Jeff sat down on a nearby bench shaking his head in disbelief.
“Hang on” Dan had been silent throughout most of Scott’s narrative so his voice gave us all a slight jolt as he never spoke much anyway. In spite of that Dan was the most popular out of all of us, and the most paranoid “do you have any proof?”
“Sure” Scott said smugly and he subtly reached into his pocket and removed dark black panties with frills along the edges. Jeff got up and lunged for it in an instant, Scott stuffed it back into his pocket “Piss off!” he hissed at him angrily.
The bell for lesson went and we set off our separate ways. Throughout the whole of English I chose not to listen to Mr Arnette talking about Shakespeare and look around the girls and chose girls I’d like to do.
“Mr Bay, Mr Bay!” I looked up at Mr Arnette
“Yes sir” I said weakly
“What was the name of Shakespeare’s last major play?” He had a sadistic smirk playing about his lips, confident that I didn’t know the answer.
I panicked, I could fell sweat running down my back, was it the heat or was I going red? Suddenly that erection I’d worked up felt like it was bulging over the table “Uh…the…tem-pest?” I prayed to any greater force there was that I was right.
Mr Arnette straightened and his nostrils flared “continue writing Mr Bay” It always gives me a great sense of satisfaction when that happens.


I was trudging back home through the heat, wishing I’d chosen to wear shorts. I noticed a moving van; three burly men in overalls were hauling boxes in and out of the house attached to ours. The gardens were separated by a hedge. I hurried inside and up the stairs to the spare bedroom at the front of the house. All I could see boxes moving back and forth across my vision. Then the new owner of the house next door strode out of the drive. My jaw dropped, she was incredible. She had soft, gentle face, framed with wavy blonde hair. The sun sparkled a little off glossy pink lips, she had warm emerald green eyes, and every time she blinked long, well combed lashes fluttered a little in the breeze. Her neck was slender but it widened into some of the biggest breasts I had ever seen on someone who wasn’t a celebrity. They were poorly disguised beneath a sky blue t-shirt with a logo on it I couldn’t make out, every boner—inducing curve was visible to me, her arms were bare and tanned. Below she wore a loose denim mini skirt, which swayed from side to side as she walked. Long, slender sun tanned legs intensified my erection. Her legs ended in bronze coloured open toed high heels. Swaying a little I felt like jacking off then and there. I managed to restrain myself, and decided I ought to go and say hello.
At the door I stopped ‘its way too early!’ a voice in my head snapped at me ‘she’ll be onto you if you go over there now!’
I did want to meet her but going over to her within five minutes of her arriving would only lead to her likening me to a stalker. I trotted upstairs and into my bedroom to make a start on my homework, and rid my mind of the woman next door. After ten minutes of studying as intensely as I could my thoughts couldn’t help but wander over to a world of fantasy, where I was lifting up that top and those breasts would lie before me, all mine to fondle, and kiss, and lick.
The door slamming and my mum yelling “Anthony, I’m home!” brought me crashing back to reality.
I knew I couldn’t go over to her and tell her I wanted to have sex with her, I’ve never been so attracted to someone physically like this before. My ex-girlfriend was alright, but a couple of months younger than me, always covered up her figure, and with quite small breasts. Now there was this woman, easily about twenty, twenty one? Twenty one is about right I think. Then she wears whatever she wants and has ridiculous cans, it’s almost too good to be true!
Two days later I was ordered over the phone by both of my parents individually to go next door, knock, and ask her if she needed anything. Simple enough. I’ve just got to not cum in my pants while I’m over there. I hurried out of the house and out onto the pavement. I kicked a stone and sent it skittering into the road. I turned and walked as quickly as I dared down a winding crazy paving path, the hedge loomed over me, tall and passive. I walked onto a painted white porch and rang the bell, stood back a few steps and waited.
From within I heard “Coming!”
The woman opened the door and I felt a rush of blood go to my penis. She was wearing skin tight exercise gear “uh, hi” I said desperate not to stutter or screw up “I’m from next door just over there and I was wondering if you need anything just come over and ask and…yeah”
“Oh I recognise you! I saw you walking home from school when I moved in!” I was just thankful that she hadn’t seen me staring at her from the window “I’m Natasha by the way” He voice was flowery and she had a perfume on that smelt like lavender.

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