Back in College, I had been seeing a girl for pretty much my entire freshman year. Since I was still a virgin when I went to school and she was fairly experienced, I had many firsts with Lucy. She had many curves, not the least of which were her very full breasts, 36D to be exact. Since I was a breast man, this was like being a kid in the candy shop. She would often let me just sit and massage them, which sometimes led to other things, but not always. It certainly got me hard every time, though. Her sex drive was not as strong as my 18 yo male needs, so I was often rejected, but she would be a good sport and jack me off every so often when we didn't fool around. Lucy was very firm about staying a virgin, however, so we never actually had intercourse, but our sex life was very full and included everything up to that.
The summer after freshman year my parents planned a trip to the lake and had rented a place big enough for my family and had space for Lucy as well, so they invited her along. Since we hadn't seen each other for a time, my hormones were off the charts. Everyone but my parents were in a common sleeping area, so there was no opportunity for stolen sex in the cabin, so we had to get creative. We stole away for a couple of late night walks on the lake and into the woods, and had frantic mutuals to satisfy our lust for each other.
This story begins as a day on the beach with the entire family at the State Park. There was a BBQ, and frisbee, and all the other trappings of a day spent in the sun. The entire day I was having to hide my erection as my Lucy's big tits were falling out of her suit and turning me on big time. There was just no way to get away for some quick sex with everyone there and a full park of people.
At one point we decided to rent a sailboat for a few trips around the Bay, where there were many other crafts enjoying the great, sunny day. Since it was fairly small, you could only fit two or three people in the boat, so Lucy and I made the first trip, and others in my family would take the boat after us. We climbed in and sailed out into the bay, avoiding other craft as we went. During our conversation I mentioned to Lucy how great she looked and that her awesome rack was turning me on big time. She said prove it, so I slipped my dick out the side of my suit to show her, which made her giggle and look around to see if anyone had noticed. By this time the wind had taken us towards one side of the bay, so there were very few boats around.
Seeing this, she decided to reach out and give my hardon a few tugs. I groaned because it felt so good and I was expecting her to scold me and make me put it away. It was also a great turn on to be under the sun, sailing on a pristine lake, watching my big titted girlfriend lean over and began to stroke my firm dick. She continued to stroke me gently as I turned the boat around to head for the other shore, and I was in heaven. Soon she spit on her hand and started to stroke me with purpose, and it felt even better and brought moans from my throat, which made her grin. As she stroked me, she noticed we were getting close to another boat, so she pulled her hand away and I brought my suit leg down a little to cover up my dick. We waved and laughed as we passed by the boat, and she resumed caressing me once they had passed, putting more spit on her hand to help things along. This happenned a couple of more times as we crossed the bay, which helped me prolong the pleasure of Lucy's wonderful handjob. Towards the secluded end of the bay, Lucy even let me take out her breasts and caress them in the sun as she continued to bring me pleasure with her stroking hand. She would reach down and caress my balls as well, bringing me closer and closer to orgasm. We had to turn around again, so she pulled up her suit but kept jacking me off until we came closer to a boat. This enabled me to back off my orgasm as we made it through the busy part of the bay, but she was sure to keep me hard in between greeting other boats.
Finally we were on the other side of the bay again and I reached in to caress her big tits once again. She lubed up her hand and started to stroke me with a firm grip, which felt fantastic. I let go of the sail and the boat slowed down as we drifted toward shore. Lucy began to increase her tempo, I was loving the feel of her full breasts in my hands, and we both knew I was getting close to blasting my load. Finally I leaned back on the edge of the boat and enjoyed the sensations of her moving hand and her other hand begin to rub my balls and creep down to rub my asshole every now and then, which she knows I love. Finally, she changed her grip, pulling my dick straight down and milking me with her hand while rubbing her fingers over my ass at the same tempo. I could hold on no longer, and shot cum onto the floor of the boat while moaning with every shot. She continued to milk me until I came down from my orgasm, pulling every drop of cum from my dick, which splashed onto the floor of the boat, mixing with my other cum and the water that splashes around inside the boat. We ended with a long, sensual kiss and a caress of those wonderful breasts before rearranging our suits and turning the boat back to shore. What a fantastic sail around the bay.
When we returned, Lucy jumped out of the boat and other member of my family got in so I could give them a ride around the bay. They all thought my big smile was because it was such a great day to be out sailing. Well, it was really because I had just gotten a long and pleasurable handjob from Lucy, but also because my cum was sloshing around all of their toes and they had no idea.
Lucy and I snuck around at night for some other quick sex opportunities, but I will never forget that extended handjob and wonderful tit play during our day sailing on the bay. We eventually broke up as she turned out to be quite a bitch, but I sure miss long sessions massaging her wonderfully large breasts, and getting handjobs from her whenever I could.