2 comments/ 73280 views/ 21 favorites Best Beach Trip Ever Ch. 01 By: bige32123 The summer in between my senior year of high school and freshman year of college my family went on vacation to the beach in Destin, Florida. The trip consisted of Me (Jake), my best friend(Dylan), his girlfriend (Kaley), and my parents. We had rented a condo in Destin for the week and were all excited to go to the beach and what not. We entered the condo and immediately got settled in. We went out onto the balcony which overlooked the gulf and there were tons of people on the beach. Now I should probably describe myself a little. I'm 5'6 and 115 pounds. I'm very skinny with short brown hair. Even though I was 18 I looked about 14. Dylan works out and has a very chiseled body. Kaley like me and Dylan was 18 but looked as though she was 14 or 15. She was about 5'2 and 110 pounds. She had a tight butt that was described as one that black girls would be jealous of. She was a B cup and wore glasses with brunette hair. She is very easy on the eyes. She and Dylan had been going out for about 3 years. I wasn't sexually active. Dylan and Kaley were however. So when I tell you it was very exciting to see Kaley step out of her room in a tight two piece, she was a sight to behold! Me and her make sexual jokes towards each other like "let's get naked" all the time but have never acted on those intentions at all. Little did I know that was all going to change soon. We had been down to the beach during that first day but went back up to the room at about 5:00. We had dinner and were just hanging out. It was about 8:00 and I suggested that the three of us go walk on the beach. They both agreed and with our bathing suits still on we walked downstairs. We walked along the beach with a couple of towels in hand down to a spot were no condos were overlooking the beach. They had a few people on the beach with flashlights but only a few walked down to where we were. We set up a spot in the deserted area and sat down. The conversation drifted from different topics with one of those topics leading to sex. We all talked about how crazy it would be to streak the beach or go skinny dipping in the ocean. We just kind of laughed it of. Dylan got up and walked toward the ocean to go pee. So me and Kaley continued to talk about random things when her jaw dropped. I turned to see what she was looking at and my jaw dropped as well. Here came Dylan walking toward us stark naked, bathing suit in hand, and dick pointing out. We were stunned. He stood in front of us and threw his bathing suit behind him. Kaley "Dylan! What are you doing?" Dylan "I'm sick and tired of the three of us talking about all the crazy things we should do. We're going to college in less than a month! We need to start doing those crazy things. Starting tonight." He turned to me. "Jake" he continued "come on bro. Join me. You won't regret it." I said "No. I'm not going to make things awkward for me and Kaley." Dylan "Pussy!" He turned to Kaley "Baby, come on. Join me!" Kaley "No! And put your clothes back on. You're being ridiculous." Dylan "I'm staying naked. Whether yall like it or not." Dylan sat down completely naked and carried on the conversation as if nothing had changed. I however could not stop looking at my best friend in all his glory. And neither could Kaley. I was astounded at how calm he was being. He was so confident that I even started to contemplate the idea of joining him. About 5 minutes passed and I couldn't help it. I stood up in front of both of them. "I can't take it anymore" I said. I closed my eyes, grabbed the waistband of my bathing suit, and in one swift motion pushed them down to my ankles. There I stood before my best friend and his girlfriend. I was hard and I was 100% naked. I took a moment to feel the cool beach air around my naked body. I finally snapped back to reality. Kaley's eyes were fixated on my cock. Dylan stood up. "That a boy" he said. He gave me a high five and turned to Kaley. "Your turn baby!" Kaley said "This is ridiculous. I'm not doing this." "Kaley" I started "How about if we undress you. You close your eyes and we'll strip you. Then everybody will be naked and it won't be weird." Kaley "I don't know." Dylan "Trust me." He held out his hand to her. She looked around and grabbed his hand. There was a spot on the towel where she was beginning to become wet. She stood in the middle of me and Dylan. Dylan motioned to me and put his hand at the back of her bikini top. With that motion I stood in front of her and dropped to my knees. I grabbed the top of her bikini bottoms. Dylan "Ready, Set, Go." On go he snapped the back of her top and pulled it away from her. I grabbed her bottoms and pulled them clean off her waist and let them fall to her ankles. Her pussy was exposed in front of me. It was truly a sight to behold. I stood back up and examined her entire body. This was my first naked woman and I'm glad it was her. Dylan "See, doesn't that feel amazing?" He threw the top with the rest of our stuff. She stepped out of her bottoms and threw them towards our stuff. The three of us stood there and examined each other under the moonlight. "So what now?" I asked. "Well" Dylan started to run towards the condo. After about 25 feet or so he turned around "Come on. This is what we talked about doing!" Me and Kaley looked at each other and began running. We ran towards the edge of where one of the condos began. We were about 100 ft. from the condo and from where a group of people were with flashlights. We turned around and ran back towards our stuff. As we approached the towels we all collapsed on top of each other. I was on bottom with Dylan on the side of me and Kaley fell on top of both of us. She looked at Dylan, and then at me. She pushed off of us and laid back on a towel. She began to finger herself! Right in front of us she began masturbating! I could not believe it. Kaley was spread open on her back and moaning as her finger slid in and out of her. Me and Dylan looked at each other. Dylan moved to one side of Kaley and began stroking his cock over her. I was stunned at what was happening. All of the sudden I was brought back into reality when I felt a hand on my own erection. It was Kaley's! She began to pull me by my dick towards her. As I reached her she released my cock and began to finger herself again. She was masturbating in the middle of us while Dylan and I were stroking our own cocks right at her side. I began using my free hand and rubbing it all over Kaley's body. I played with her nipples. Dylan was doing the same thing. It only took a few minutes before we all three climaxed. Me and Dylan both came on her face. As we shot our loads on her face she opened her mouth. What she did next was just as surprising as she leaned up and licked the remaining cum off of both Dylan's dick and my own. She then proceeded to fall back and breath heavily. Me and Dylan both fell on top of her. After about a minute of laying there catching our breaths; Dylan noticed that the flashlights were getting a little to close for comfort. We decided to put our clothes back on and call it a night. We got dressed and packed up. We were led toward the condo with Kaley pulling both our crotches. As we got closer she turned and flashed us both. She came up and kissed both me and Dylan. She looked at me and said "For this week, what's his, is yours." She grabbed my hand and put it on her still exposed breast. She then said to Dylan "Is that ok baby?" Dylan just nodded his head with a smile on his face. He grabbed both our asses and gave them a nice squeeze. This was going to be a fun week! Best Beach Trip Ever Ch. 02 After the first night on the beach it was apparent nothing about this trip is going to be ordinary. Nor would the three of us be the same again. When we got back up to the room the previous night our parents had already been in bed. The three of us went into Kaley's room to talk about what had just happened. It was almost a little tough to look at them both now. Which surprised me a lot. We had all seemed so confident on the beach but now that we were in the light of Kaley's room; it all just became a little surreal. The conversation of course turned to what should we do next and how far we were willing to go. No one knew the answer to the second question but to the first I suggested skinny dipping. It was an idea met with both enthusiasm and scrutiny. The question was how and when? Dylan came up with the answer. Dylan "What if we went to a clothing optional beach?" This suggestion brought stares from both me and Kaley. We looked at Dylan in bewilderment. The kid who had a problem changing into his clothes for P.E. in high school was now suggesting to go and get naked on a beach with a bunch of strangers. Dylan shrugging his shoulders, "Why not?" Kaley and I again looked at each other. We both nodded our heads in agreement to the suggestion. It was settled. "So where is this beach exactly?" I asked. "That's the beauty of it," Dylan started "That's where we were tonight!" "Really?" Kaley asked with a confused look on her face. "Mhmm," Dylan continued "I looked it up yesterday. I was going to take Kaley there sometime this week to see what it was like. But when Jake suggested a walk on the beach. I figured we might as well all check it out." "Well in that case, I'm game to go." I said. "Kaley?" "Sure!" Kaley started "but first, both of yall strip right now!" Dylan and I looked at each other. We both began taking our clothes off. Both of us having hard ons that pointed right at Kaley. We just stood there. Kaley "Alright. Night boys!" She blew us a kiss and turned off the light. Dylan and I gathered our clothes and went to our room. After a quick session of masturbation we both went to sleep; naked of course. The day started out as all the rest would. Mom made breakfast while dad went to the workout center to exercise. The three of us woke up at around 10:00 and got dressed to go to the beach. Dylan and I now had no problem just changing in front of each other. We both took our time with putting our suits on. There was something about Dylan I was beginning to notice. I think Dylan was bi! He just couldn't stop staring at me sometimes. I didn't mind it because I too like being seen naked but I kept the case open and figured I would have an answer by the end of the week. After breakfast we went down to the beach as a family. We played in the water and tanned. It was about 1:30 when my parents went up to the room. We told them that we were going to stay down. My parents just nodded their heads and left. When they were gone we began to walk toward the other beach. It took all of 10 minutes to reach sign that we had not seen the previous night. The sign read "Clothing optional from this point forward." We could see some people in the distance but weren't close enough to see any details. We all just looked at each other. And in time, all stepped past the sign and onto the clothing optional beach. We walked another 5 minutes or so until we found a spot. We had passed a bunch of people both male and female. Some were good looking and others we wished would have stayed clothed. There were a lot of older women. Most were just topless with a few that were completely naked. We set up our spot and sat down. All of us looking at who was going to make the first move. Like the previous night I couldn't take it anymore and took off my swim trunks. It felt so much different from last night. There was a cool breeze that overcame me. The sun felt warm and inviting on my butt and penis. I was very surprised when Kaley was the next of us to strip down. She started with just her top and stopped for a moment. She then said "What the hell?" and took off her bottoms. Now if was I wasn't hard before I was now. I finally got to see Kaley's naked body in the light. It was amazing. Dylan quickly followed and took his trunks off. There the three of us were naked on the beach. We laid there and tanned for a few minutes before Kaley got up and headed toward the water. I watched as her ass cheeks moved up and down as she walked. She looked back and winked at us. When she got to the water she stopped as she let the water run over her toes. After a minute or so she walked into the water and let the waves overtake her. Kaley was out in the water for about 5 minutes before Dylan went out and joined her. The two of them treaded water together and splashed around. There was no one near them so they had privacy. I at this point was horny so I made my way to the water joined them. When I got in the water it was amazing. It might have been more amazing then the sun on my body. The water just surrounding every inch of me was enticing. I would be doing this again very soon I thought. 5 minutes later Dylan went back up on shore to get something to drink. Leaving me and Kaley in the water together. Kaley came over to me and we began talking. Kaley "The water feels great doesn't it?" "It really does. I think I like this better than anything so far." "Oh really?" She started swimming toward me "How about this?" She put her hand on my shoulders and wrapped her legs around me. Our naked bodies were now touching each other with zero space in between them. Kaley looked at me and kissed me! I was stunned! This of all things I was not expecting. I broke the kiss off. "What about Dylan? Won't he be mad?" "Nope!" she began explaining "That's what I was just talking to him about. He said he's fine with me doing anything I want with you as long as he gets the same thing. I told you, this week whatever's his, is yours." She then kissed me again and we began making out. The feeling was great. Getting to makeout with a girl completely naked in the ocean. I thought I was on top of the world. I moved my hands all up and down her body eventually stopping on her ass. I slipped a finger into her asshole at which point she shuddered. I guess Dylan had never done that to her. After a few minutes of passionate kissing Kaley grabbed my hard on and while still kissing, got me off. I spewed my cum into the ocean. When I was finished we got off each other and walked back up to the beach. We returned to our towels and noticed a few feet from us that Dylan was talking to someone. We walked over there. "Hey guys! I'd like yall to meet Raymond. Me and him used to work together at Dominos." Dylan said. I shook hands with Raymond and he began chatting with us. I took a moment to look at this guy. He was a year older than us and went to a college out of state. If you can imagine what Chris Evans from the Captain America movies looks like than you can imagine Raymond. He had great body and like us; was completely naked. He had a nice package. Probably about 8 inches. I could see Kaley staring at it. It was kind of a turn on. After a few minutes of talking we went our separate ways and we went back to the towels. We spent the rest of the afternoon on the beach walking around, checking out the views, and tanning. At about 6:00 I got a call from mom saying dinner was ready. We gathered our things together and walked to where the sign was. It wasn't until we got here that we put our clothes back on. We walked back to the condo and ate dinner. That night we decided to stay in and watch a movie. My folks went to bed. At about 11:00 after the movie we all ended up in Kaley's room. My folks had been asleep for about an hour. We all three talked about the days events. It was filled with some awkward moments as I think Dylan was a little jealous when he heard about me and Kaley's make out session. But for the most part we were all able to laugh it off. "I have a suggestion" said Kaley. She stood up and began to strip. When she was naked she gave us a look that told Dylan and I to strip. We both did. Kaley laid down in the middle of the bed. "Get on the sides of me." she commanded. Dylan and I walked to either side of her. Kaley grabbed both of us and began jacking us off. It was incredible having her handle both of us at the same time. Dylan looked at me and gave me a high five as I think he was over his jealousy. We both came on top of Kaley. With dicks in hand she leaned up and kissed us both. "Night boys!" She slapped our asses and sent us out of her room. We gathered our clothes, went to our room, and went to sleep.