I love this site. Some good reads. I hope you like mine. Not a big deal but it was fun back then.
When I was 19 year old I met a girl the same age at our cottage who was staying for two weeks with her grandparents. She, Jessie, was a nice girl but took every chance she could to do something wild or risky. I took a real interest in her right away but I think the only reason she hung with me is because there was nobody else our age on our side of the bay.
We went canoeing one very hot day, portaging into the next lake where it was quiet with no cottages. We stopped at a rocky shore and pulled up the canoe then got out to swim. Both of us had shorts on and Jessie had a bright yellow bikini top holding her perfect medium sized tits in place.
After our swim we were drying off while sitting on the rocks and Jessie caught me looking at her tits, twice. She made me feel embarrassed calling me a pervert but she said it in fun and like she was teasing. She asked me if I wanted to see her tits and get it over with so I could relax. I answered with a shy and loud 'no' even though I really wanted to see them. Then she teased me about being shy and asked me if I even liked girls. I just couldn't win so finally I told her rather loudly that I wanted to see her tits.
I could not believe what I just said but I'm glad I did. Jessie stood up and reached behind her back and pulled the string on her bikini top then out bounced her lovely tits! Were they nice! Hard and firm, round on the bottom and her nipples turned up just a bit pointing to the sky. She stood with her hands on her hips and told me to have a good look because she was going to put them away soon. Seconds later they were going back into the little yellow bikini.
I was shocked and happy at the same time. Jessie sat down again and asked if I was ok. Then she asked what I was going to show her. I fumbled searching for words and before I found an answer she told me I should drop my shorts for her. I refused, but wanted to show her my cock that was now half hard waiting to come out and play.
Jessie kept teasing me about being shy and how I was not showing her anything. While still teasing me she stood up and undid her top again then she slid her shorts off and went for a swim. She shouted back to me, 'come on, you must have gone skinny dipping before'. Now I thought, don't let this chance go by. Nobody was around and I wanted to show her my cock so bad!
Off came my shorts and I made sure to stand tall and show my cock that was now at it's full hardness. I was pointing the same direction as Jessie's nipples, to the sky.
I waded in and I could see Jessie's eyes on my cock all the way. Now I was really horny. We soon got back out and my cock was still at full length and hardness. Jessie just never stopped. We laid on the hot rocks and Jessie sat right back up and asked me, 'don't you have to do something to get rid of that'? 'What' I said, but I knew what she was referring to. 'That' she said pointing to my hard cock laying back on my belly. 'No' I said, 'it goes away by itself'.
Jessie sat looking at my hard cock some more then she said 'it's not going away you know'. I sat up she pointed at my cock again telling me how hard it still was. 'Does it feel bad to leave it like that' she asked? 'Stop asking me so many questions' I told her but so hoping she would keep talking about my cock.
She went quiet for maybe a minute then she spouted something that made my heart jump into my throat. 'Why don't you jerk it off for me' she said. 'Nobody can see us here and you know I'll never tell'. 'Come on, just do it for me, pleeeese, then you'll feel a lot better right? 'Come on, go for it!' 'Just start doing it and don't think about it' she said as she reached over and grabbed my hand and pushed it toward my cock. She held my hand there and moved it up and down and said 'see it's not that hard, just do it for me.'
She kept pushing like that so I just took a hold of my cock and started doing it. I remember how good I felt both in my mind and deep in my cock and balls. I had never jerked off for a girl before ever! It felt really sexy jerking off for her.
Jessie had a smile that never stopped all the time I jerked my cock. I knew I could last for a while because I had just jerked a big load a few hours before that morning. Jessie talked a lot while I was jerking for her. She told me she liked watching guys jerk and that I was the third guy that she had watched. Soon my cock was ready to squirt my wonderful cum. I thought I would last longer but I just wanted that feeling so bad!! As my orgasm crept up I told Jessie I was going to cum in a few seconds. She leaned forward getting closer to my cock and I leaned back pressing my cock high into the air. Then it hit hard! Hard long strong squirts of cum shot about a foot into the air while Jessie made little 'oh' noises after each time my cock squirted a new string of cum.
My orgasm ended but I kept a nice tight pull downward on my tight foreskin to enjoy the nice feeling of the after orgasm while my cock pulsed like it had a heart of it's own.
I kept holding my cock tight while clearish white cum ran out the end and down onto my fingers. It was the last of my show for Jessie. Soon my cock began to fade and I let it drop to one side while I scooped cum off my body. I stood up and went to kneel by the waters edge to rinse the cum off.
'Wow, that was a good show' said Jessie. I turned back and started to pull my shorts on feeling a bit awkward now that the thrill of jerking in front of her was over. Jessie stood up and got dressed too then we slid the canoe back into the water and paddled our way back to our lake.
The ride back was quiet and there was no wind that day so the lake was silent. Jessie stopped paddling and turned to look at me. 'Why didn't you ask me to do it too' she said. 'I never thought to ask' I told her. 'I would have you know' she said, then she turned and paddled back in silence.
Looking back now I kick my ass for not stopping the canoe and letting her masturbate for me. I was 25 before I saw a woman masturbate and it was not as much of a thrill as it would have been had she been just a girl and not my girlfriend.
I only saw Jessie one more time after that day and we weren't alone much at all. Our day of fun was three days before she left to go home. I wanted to see her before she went. I had made my mind up to kiss her but I never got the chance. I never saw her again either. My family were not close with her grandparents so I never even got the chance to ask how she was after she left.
That's it! Not a huge deal but it was for me. At that time of my life I jerked off every day and usually two to five times a day. After my encounter with Jessie all I could think about was that day, jerking for her. I just closed my eyes and I could see her nice hard tits hanging tight to her body while her eyes watched my hand move up and down my cock. Her pussy had light blonde hair and not much of it. Nice round ass too. Mmm, nice. Oh was I stupid!!!