It was a perfect day for sailing on San Diego Bay . The day started foggy but it was sunny and warm by the time we were at the dock. My brother asked me to play captain for a small group, which included my sister-in-law, two friends of theirs who were visiting from Australia , and a local friend of my sister-in-law whom I hadn't met before. I booked a 36 foot Catalina.
When I arrived at the marina, I walked over to the rental company to sign the paperwork and get the boat information. The rental office was a small, one-door store front with a single desk and a water cooler. There was not much else there except for the cute lady behind the desk. Even from across the courtyard I noticed her and was impressed at how good looking she was. She had long, curly brown hair with a cute face. When I walked in the door, she stood up, and I was instantly even more impressed. She was wearing a tight green sweater that showed off her really nice tits. Her pants were basic khakis, almost like hiking pants. It was a rather granola look, with her sandals, khaki pants, and curly unkempt hair, but she was able to pull it off and I was rather turned on. She introduced herself as Jenna, and we talked for a bit about sailing and the key features of San Diego Bay . At one point, I was looking at the chart on the wall and when I backed up, I walked into her. She stumbled but steadied herself by putting a hand on my waist. It was an electrifying touch, albeit brief.
As I left her office and headed to the boat, I was definitely flustered. She was so damn cute and sparkly. I found myself very turned on. I got to the boat, and was getting a briefing by one of the deck hands, when the rest of my group showed up. I gave a kiss to my sister in law and shook hands with my brother, who then introduced me to their three friends. The two women from Australia were attractive, 7's, but once they spoke and I heard their great accents they were both 9's. The other woman was from San Diego and was very attractive; she did not have to open her mouth to be a 9. Her name was Alison and, when introduced, gave me a warm smile and a soft handshake.
We loaded ourselves and our gear on the boat. I tried to focus on the sailboat and off Jenna and the three ladies on the boat. I motored out of the marina, listening to the Australian ladies speak. I chimed in occasionally with some wisdom about the bay or sailing in general, but my main focus was on Alison. She was sitting behind me and it was hard not to keep looking back at her. With my sunglasses on, I was able to check out the Australian ladies in the front of the boat at will, but Alison was out of my view.
After a short motor, we got into the bay and worked on raising the sails. Once we were comfortably under sail, I headed south in the bay towards the bridge. The waters were smoother there and the views of downtown were great. The sun was high in the sky and the temperature was a pleasant 80 degrees. The two Aussies and my sister in law went below to get their swim suits on, while my brother talked about nothing in particular. Alison was still behind me. Much to my dismay, she did not bring a swimsuit, so I could only imagine how her tits looked without her t-shirt on. I needed a reason to get her in front of and closer to me, so I asked if she would like to try driving the boat. She quickly agreed. I offered my hand to her and she accepted. I helped her stand behind the wheel and gave her a quick lesson. I stood behind her and placed her hands on the wheel explaining the center line and pointed to an object on land for her to aim at. She shortly got into the sailing and in her excitement she would occasionally lean back against me or push her ass back into me. I am sure it was all very innocent for her, but it wasn't for me. In fact, I had to stand back so she would not feel my growing hard on.
Before long, the three ladies returned to the cockpit in their swimsuits. The three of them looked good in suits that showed off plenty of cleavage and their nice racks. The two Australians went towards the front, with a towel each, to lay out. Even though they were a distance away, with the slope of the boat and the way they were laying, I had a great view. Alison noticed the same and even called me out, saying how much I must be enjoying the view. I replied, "It did just get a little better."
Right after her comment, we hit a wave and she bumped her ass into my hard on. This time, she lingered there a little longer and let out a giggle. When I asked why, she laughed and said she was just having a great time.
The afternoon got even better as the wind picked up and I took the wheel back from Alison. She did not return to her seat, but instead stayed next to me as we sailed north in the bay. As we would hit a wave, she would reach out to hold onto the wheel or stanchion or occasionally hold onto me. We talked the whole time and were having a lot of fun. She was very touchy and I loved every minute of it. The two women on the bow were a great sight to watch, but my mind was totally on Alison. Well, and every now and then on Jenna from the rental office. I kept thinking it was too bad that it was not just me and Alison on the boat. She had great lips that would be perfect for sucking dick. I started fantasizing about her getting a couple towels, kneeling down, and sucking me as we sailed out of the harbor. Once out in the open ocean we would lower the sails and have sex on the deck, becoming a part of the waves as we had sex. There would be other boats due to our proximity to the bay and we would run the risk of being seen or watched. That would add to it. Being watched, fucking each other, using the waves to add to the sex, the waves making her tits bounce. After sex, she could lie on her back on the floor and play with herself in front of me as I get us under sail again. The fantasy was over too soon as we had to change course to avoid another sailboat.
The trip was over too soon. We got back to the dock about an hour before dark. We all said our goodbyes at the slip while I worked on securing the boat with a deck hand. I walked Alison a little ways down the dock and then gave her a hug, which she held for a nice amount of time. It was too bad that Alison was leaving, but I was excited to go see Jenna. I made my way to the office and found Jenna sitting behind her desk. She stood when I walked in and gave me a big genuine smile. We talked about the sail and the weather. I told her there were a couple issues with the boat that should get looked at. It was funny; she smelled of alcohol.
"Is it was happy hour yet?" I joked.
Jenna replied, "It was an hour ago!" She opened her desk drawer, "Would you care for a drink?"
I am not one to pass on having a drink with a lovely lady, so I agreed and she poured me a drink in a red plastic cup and we continued talking about the boat. I offered to show her the problems on the boat and she agreed. We left the office with our red plastic cups and headed to the boat.
We got to the boat after a short walk and I took her hand to help her on board. She smiled again and looked back at me, catching me staring right at her ass.
"Like what you see?"
"Sorry," was my feeble response.
We stepped through the cockpit and she led down the short ladder to the cabin. There was a small kitchen, navigation table, two couches and a bathroom and bedroom towards the front. Behind us was another bedroom. The cabin was all wood with blue upholstery and three small portholes on each side. I showed her a problem on the electrical panel. Jenna was behind me while I pointed out the issue and she was leaning into me so hard I could feel her tits pushing against my back. The electrical was an easy fix. Next, I showed her the problem in the bathroom at the sink. Being a boat, the bathroom was tiny and it was not easy showing her the problem. We managed to both squeeze into the bathroom. When we looked under the sink, our faces were an inch or two from each other. Out of nowhere she kissed me on the lips. It was a quick peck...nothing else...almost imperceptible. But it was definitely a kiss and her narrow wet lips felt really good. It was quiet. We did not move, both waiting for something, kneeling on the floor of the bathroom. What the hell, I thought, she was cute, her lips were sexy, and we were on a boat. I kissed her back, longer this time. I put my hand behind her head and held her to me as we kissed deeper and harder. With my other hand, I worked my way up her leg, across her stomach, and towards her tits. As I touched her breast, I stood up, bringing her with me. I gently pushed her through the door to the forward cabin. It was only three steps before I pushed her onto the bed in there, lying on top of her.
The kissing became more intense. She pushed her pelvis into me, grinding against me. I kissed her neck as she moaned approvingly, saying how good it felt. I put my leg between hers so that she could rub her pussy against it as I kissed her neck. Her hands were all over me, running through my hair, down my back, grabbing my ass, and pulling me into her. She was very aggressive, which I really liked about her. I slid my hands down her side, eager to get them under her top and pull it over her head. As I lifted the tight green sweater up her body, she raised herself off the bed. The sweater was so tight that it took a little extra effort to get over her tits, but the effort was so worth it. Her tits looked amazing in a satin bra that was tight and pushed them together, creating a deep, inviting cleavage. I took the sweater off and threw it behind me onto the floor of the main cabin. Then I kissed my way down her chest.
The smooth fabric of her bra felt good in my mouth. Her hard nipples were pushing against the bra. I loved the feeling of the fabric, but I really wanted her naked tits in my mouth. Before I could get to taking off her bra, she unclasped it and pulled it away. Her big tits were now all mine. She begged me to suck her nipples and bite them lightly. I did as she asked and was treated to moans of approval.
I kissed down her stomach with my hands still on her tits, squeezing the nipples between my fingers. I teased her, enjoying her anxiety, testing her to see if she was going to let me continue. To my surprise, she wanted very little to do with my teasing and asked me to take off her pants and eat her pussy. Her legs were hanging over the small bed and, with a slight lift of her hips, I was able to quickly pull her pants and panties off, tossing them on top of the bra and sweater.
Her pussy was right in front of me. I immediately buried my face between her legs. Her pussy was trimmed nicely and tasted great. I pushed my tongue in deep and then licked my way up, using my tongue to play with her clit, while my hands stayed on her tits. She had a hand on my head and to make sure I would not leave her pussy. I had no intention of doing so; it tasted so good. She was squirming with desire and encouraging me by talking about how much she wanted it.
