Naked With Brother and Girlfriend

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 twin brother (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. Dylan and I were 18. My brother is the exact same as me so there is no need to describe him.

Kaley like me and Dylan was 18. 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.

None of us were sexually active. Dylan and Kaley had done some stuff but never had sex. 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.

Haley "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!"

Haley "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 brother 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 brother 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."

"Haley" 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 my twin brother 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!

To be continued...