Dianne The Girl Next Door

One day as I took the elevator to my office I came across Dianne who grew up in my neighborhood. She was always the nice and quiet one while her sister Debbie was the wild one. I had not seen Dianne since she graduated from college. I heard that she got a job with a the government but that was it. One day I ran into her as she was heading to a meeting. I invited her to stop by my office when she was free. A few days later she stopped by and we chit chatted about her job and why she was in the building. She had one of those government jobs that couldn’t be discussed. We talked about where she lived, Coronado. Was she dating, No…he was too immature. What she did for fun..nothing really. So I invited her to drive to San Diego and meet me and my friends for Happy Hour. She said that she would think about it and get back to me. I also extended the use of one of our offices just in case she was in the building and needed to hang out in between meetings. She was super appreciative of this. I got a text the next day from Dianne saying that she would love to meet up with me and my friends in San Diego and what should she wear or bring. Wear…I said shorts, t-shirt and soft soled shoes. What to bring nothing just her. Then an hour later she responded that she is off all day on Friday so what time should she head down. I said how about we go sailing and then meet up for happy hour. I also said bring an over night bag..just in case she gets wet from sailing or we get caught in a storm. Dianne arrived at my townhouse at 11:00am. I told her where to park and to walk right in. When she was walked in I was finishing up making lunch. She came in with her bag and gave me a BIG hug. I noticed that she was wearing a pair of super short shorts a t-shirt that showed the outline off her bralet and a pair of white tennis shoes. I gave her a tour of the townhouse and showed her where the guest bedroom was..she dropped off her bag. After the tour we grabbed a few bottles of wine from the fridge and went down to the sailboat. Me—>Dianne do you have any sailing experience? Dianne—>No, Me—Dianne can you swim? Dianne—>maybe. We laughed and then I gave her a waist life vest. As I got WinPowered (my sailboat) out of the harbor. Dianne became right at home and put away all of the food and wine and poured us a glass of wine. As I raised the sails and began to make our way towards open water I put Dianne at the helm and she did great she followed all instructions and seemed to enjoy sailing. After an hour or so…it was blazing hot. So I took off my shirt. Dianne said well since you started and she took off her t-shirt leaving her in a bralet that didn’t do a good job of hiding her boobs. By this part in the trip we had finished off 2 bottles of wine. So I made the comment I hope that you are ok with me looking at your boobs…if you aren’t I will do my best not to. Dianne responded…THANK YOU…I want you to look at my boobs. I said ok awesome. We dropped the sail and maneuvered the boat into a cove. I dropped anchor. Dianne had taken off her bralet and was completely topless. She was comfortable being topless around me. She could also see that I was getting hard. So she asked “Any objections to me taking off my shorts?” I said absolutely NOT! Since Dianne is a type-a person she responded I want your shorts off. So I took off my shorts and she pull off her shorts and panties. The 1st thing that I noticed is she had a full but manicured bush on her vagina. I went into start making out with her and she responded favorably. She whispered in my ear “Im not on the pill and I dont want to get pregnant so if we have sex and you think that you are going to cum…please use a condom…I always have 1 or 2 in my purse…just in case. We continued to make out. I laid Dianne on her back where I started to eat her out. I could taste it when I made her cum. She was about to guide me inside of her when I her a weather alert for Thunderstorms. I explained that we should get back home because riding a storm out in this boat would not be fun for a newbie. She agreed and put on her t-shirt and shorts. As we made our way back home she did a great job of following my lead and navigating us back home. By the time that we got back home it was pouring. Since I didn’t want her to get washed away I sent her back inside of the townhouse while I finished up securing the boat. By the time that I got back Dianne was in the shower. I walked in the bathroom and she took off my shorts and gave me a vicious blow job. She kept going until I came in her mouth. She then guided me in the shower where she whispered in my ear and said NOW I know that you won’t cum in me. Sam then climbed up my front and slid my dick inside of her and rode me. Dianne came at least 5x and then she collapsed in my arms.We finished showering her and then we dried off and sat on the patio enjoying a glass of wine. Since we were both hungry we decided to get dressed and meet up with my friends. I started to put on my boxers and shorts and Sam expressed her dislike of me wearing boxers or any type of underwear…I said ok and got dressed commando. She started to get dressed and I said “yeah with a body like that no way” She gave me a deep kiss and said thanks because I don’t like wearing bras or panties. She we both got dressed commando an d headed out to dinner. Over dinner the conversation flowed nicely and Dianne seemed to enjoy flashing me. We met up with a few friends and kept drinking and laughing. As we were headed home she made me promise that anytime we fuck that I have a condom on. I said ok I will. I said when we are at my house I made her promise to wear as few clothes as possible. She said definitely . As soon as we got back to the townhouse she stopped off her clothes and stripped off mine and we made out and had oral sex in every room. When we got to my bed she put a condom on my and then slid my dick in side of her. We kept going until we both came. We both cleaned up and then went to sleep. The next morning we sat in the living room naked and enjoying a cup of coffee. She told me the reason why she insists on me wearing a condom. She is not on the pill and having a kid at this stage in her career is not in the cards, her parents would be livid and then she told me a story about an old boyfriend who didn’t pull out and gave her a scare. We both agreed that we would stock up on condoms because after this past weekend we were going to need them . The next 2-days were filled with sailing fun, flashing and protected sex.