You Missed The Boat, Pal!

When I was 13, it was a strange time. My family had just moved to another Vancouver-area suburb, ripping me away from my friends as I started high school. Just after that birthday, I had the first ejaculation/only wet dream of my life. Having acquired my cumshot capability, I was hooked on jacking off and spent most of a friendless summer beating my meat and honing my skills in this important facet of life. Then, when high school started up, I met a girl my age at the school bus stop.

Chris was super-cute, with long, thick, wavy brown hair. She had a wondrous little butt, but hadn’t yet matured much in the boob department. She was really smart, and an ardent feminist much before her time. She helped me settle in to the big high school we attended where I knew nobody. We went to the odd movie and had some (very!) light necking sessions, which helped make her one of my go-to jackoff fantasies as I attempted to set the world record for most masturbation orgasms in a calendar year.

I kind of got attracted to more buxom girls as the year went on and dropped my interest in Chris after she rebuffed my attempts to initiate a more physical relationship (“I’m not that kind of girl!”). There was no doubt she was hurt by my asshole behaviour and she started going to a prestigious boarding school starting in grade 9. Although our family houses were close to each other, we didn’t see each other again until after we graduated.

I turned 18 just after grad, and the girl I had gotten into a non-exclusive mutual masturbation relationship with in grade 12 (see my “Pastor’s Daughter” stories) left to go to university in the U.S. This meant I was pretty much married to my right hand and I kind of goofed around in a gap year of sorts. 

There was a large park near our neighbourhood which the area kids used for parties and one night in early fall while I was at one of them, the police broke it up. I was cleverly able to stash my beer and pot where no-one could find it and went home, planning to retrieve the highables the next day. No big deal.

I had started back to my car the next afternoon, when I was stopped in my tracks by the vision of Chris. She had moved on from super-cute to stunningly beautiful. Her boobs, braless underneath a Mahavishnu Orchestra T-shirt, were breathtakingly shapely and jiggled delightfully as she walked. Chris was no longer a skinny 13-year-old. She was, however, out of my reach - she was holding hands with a well-dressed guy in his mid- to late-twenties. She greeted me coldly, and the guy looked at me like I was some kind of insect.

They carried on to his car, which was parked near mine, and the guy left. Chris came over to me as I was putting the beer in my car and asked me to bring a couple of bottles back into the virtually empty park, so we could “catch up.” I rolled a joint and grabbed a couple of beers and a church key and off we went to the grotto where I had hidden my stuff the night before.

We smoked the doobie and started in on the beers. Chris started lording it over me, wondering why I was hanging around in parks while she and her friends were well into freshman year at UBC or SFU. She told me if I’d been nicer to her and less superficial in grade 8, we might well have become something because she’d really liked me. Now she was going with Glen (the guy I’d seen with her) and he’d be taking over his father’s ship-building business in a couple of years.

“What are you going to do with your life, ____? And I’ll tell you something else, loser, you missed your chance with sweet little Chris. Why don’t you just give me a jerk off show, because that’s as close as you’ll ever get to my pussy!”

A couple of things flowed through my buzzed brain. This whole thing had escalated really quickly. And if Chris thought that masturbating in front of a female was some kind of punishment for the likes of me, she was sadly mistaken. I decided to assume she was serious and hooked my thumbs into the waistbands of my shorts and underwear and dropped them to my knees.

I had been semi-erect since I’d watched Chris’ tits jiggle beneath her T-shirt and it didn’t take me long to get my thick, curved, purple-headed cock rock-hard. Her eyes were glued on my dick as I slowly stroked myself. God, she was pretty, and I had to do the stop-and-start thing to prevent myself from cumming too soon.

“OK, Chris,” I finally gasped. “If you want to get out of here at a reasonable hour, you should lift that shirt and show me those big titties.” I didn’t really think she would, but she pulled up her T-shirt and let me see her breasts. They were really big, DDs I’d say, but with only a little sag, and her nipples were hugely erect. I started jacking harder, my fist milking myself towards ecstasy as pre-cum lubed my shaft and cockhead. Chris dropped her hands from the shirt and sent me over the top by pulling her shorts down a bit and giving me a good shot of her glorious pubic bush.

Grunting and babbling in pleasure, I blasted a couple of ropes of thick, white cum that splattered on her lower belly. The rest of my load got shot on my chest and neck as I pulled up my shirt with my other hand. When my balls were finally drained, I took off my shirt and wiped the cum off both our bodies. I offered to give her a ride home, but she told me to “screw off.” Fine, I thought, and walked back to my car, never to see Chris again.Things turned out OK for me, so I didn’t really care.