Best summer ever
I was 13 when this went on, my sister was 15. We live in the country sis had worked the prior summer and I had five lawn mowing gigs to keep me busy. That summer sis could not find a job and I lost three of my clients two to the economy and one to a son who was old enough to take over. I tried to find more but it seemed no one could afford a lawn boy.
Mom suggested we enlarge the garden and sell produce. We had a huge garden and mom would can stuff till the cows came home, so there certainly would be enough to get started and a second crop would more than make up. Dad built a stand out of an old seed locker. It kept us out of the sun and actually offered some privacy from the waist down. Sis and I had always been close, but nothing sexual.
That began to change that summer. It started the day we were picking cucumbers for pickling. We used to see each other in the bathroom when we were small, but when sis started to develop mom put an end to that. It had been three years since she had seen me. She held up a cue and said “this one looks like your dick”, “not any more” I said. She asked what I meant. I said “it grew just like your boobs Sissy.” She would hold up a larger one from time to time asking if I was this big. It got to the point that I finally had to start stipulating when it’s hard yea. She was incredulous I don’t think she has ever seen me hard even as a kid. So eventually she wanted me to prove what I was saying.
"What’s in it for me?” I said. She said “what do you want.” She offered doing dishes all week, that offer was tempting but I had a better idea, we both get nagged, and show our stuff. She offered to show her boobs but not her pussy, I said no deal. I countered I’ll make it hard for you if you show me your pussy (like there was any way I would not be hard) she agreed.
The next morning after our parents had left I went to her room right out of the shower she was just getting up. I said, “Are you ready for our deal?” She agreed and pulled off her nightgown. I was dumb struck. She was SOoo Hot. She normally wears bulky clothes that hide her figure. She had definitely developed since the last time I had seen her. I just stood there with my mouth gaping. I sprang and immediate boner which did not escape her notice. She demanded I drop the towel. I did my cock was so hard it was nearly purple. She asked if she could touch it, I said no fearing I might explode, she offered that I could touch her boobs; I did and started leaking pre cum. She noticed and asked if I had cum it was literally dripping off my cock. I smiled and said not yet but it wants to. She asks “does more stuff come out”. “Oh yea.” “Can I see" was her reply. I asked her if she could cum with me. She was reluctant but agreed. I got no more then ten strokes before I launched a huge load over her arm onto her pillow. She was really surprised and so was I. I have never squirted like that. When I was done she stopped rubbing her self. I said what’s up, she said the deal was we cum together, you did not give me time. I said that was only my first cum. Keep going. I had never cum twice in the same session but she did not know that. I surprised myself by staying hard. Sis seemed rather unimpressed with my continued arousal. I asked her how often she could cum twice in the same session; she smiled and said I already did this morning.
We masturbated ourselves for quite a while she seemed to keep getting close but would then back off. The last time she was really squirming and I launched my second load. I asked her to continue because she had not cum, she laughed and said "I came five times where were you?" I asked if I could make her cum, she said maybe some other day.
We took turns working in the stand there was a lot of down time between customers and there is only so much time you can spend cleaning and arranging, and counting money. I got so I would cum three or four times a day. Sis and I would masturbate together in the shed making a competition of it who could cum first.
As the season progressed, sis started adding produce to her jilling sessions, carrots, and cucumbers mostly, but the occasional weird shaped summer squash. We would never sell that produce, but sis would make a point of preparing it for me for lunch. That was hot.
Toward the end of that summer sis got a boyfriend and she asked if I could show her how to jack off a guy and practice on me. I agreed with the stipulation she allow me to do the same for her. We got so we would put a pick and pay sign in the stand at lunch time and would do our practice sessions. They eventually progressed to oral. I could lick my sister all afternoon, if she would let me. She got very good at directing me with subtle coos and moans. She would cum at least three times a day with me and I once or twice a day with her. When school started back up, cold turkey withdrawal of those afternoon sessions was too much. I would try to bust a nut between periods until I got caught, and earned an embarrassing nick name. However that worked out OK because girls wanted to be with a guy who had a reputation of being very sexual, and I did not disappoint them thanks to Sissy.