5 Years ago, my best friend John and I graduated from high school. We had known each other since 1 st grade and we became like brothers as we grew older. John lived with his mother Jessica and older sister Vanessa. His mom and dad divorced when he was 7 and Jessica never remarried. Jessica and my mom were also best friends. They had met 11 years earlier at a group for divorced moms with kids. My mom and dad had also divorced around the same time as John's parents. Jessica and my mom started hanging out when they learned that John and I went to the same school and over time, we all became very close. I was an only child and I spent a lot of time at John's house over the years, since my mom traveled a lot for work. Jessica became like a second mom to me.
Two weeks after high school graduation, my mom had to go on a long business trip overseas and I stayed at John's house during this time. John and I had big plans for that summer, considering the fact that we were going to go to different colleges and we wouldn't be able to hang out much once we started the next chapter in our lives. Little did I know that not only was I about to have the best summer of my life, I was about to have the best experience of my life.
Jessica was a well known real estate agent in the Tampa, FL area, where we lived. She was very successful and she had a beautiful home. I enjoyed spending time at her house. She had a 4,000 sq. ft. home in a great neighborhood, with a built in home theatre and a game room with a pool table, ping pong table and a couple of retro arcade games. John and I spend a lot of time in these rooms, or outside, by his pool. The pool area was great. There was a huge privacy wall, so none of the neighbors could see back there. There was also an outdoor hot tub and cabana. Jessica was cool and she would let John have friends over for pool parties all the time.
One day, John and I were hanging out by the pool with his girlfriend Josie and his sister Vanessa. I wasn't seeing anyone at the time. We were talking and listening to music when Jessica came out to join us. She said hi to everyone, and proceeded to take off her robe to sit one a lounge chair on the opposite side of the pool from where we were. My eyes almost popped out of my head when she took off her robe.
Jessica was not very tall, probably 5'3". She had straight, dark brown hair with blonde highlights, sky blue eyes and tanned skin. Over the past year, Jessica had started working out and she had lost at least 40 pounds. I had seen her a bunch of times in a bathing suit, but she always wore a one piece and some kind of draping around her waist. This was the first time I had seen her in a bikini. She looked amazing. Her arms and legs were toned, she had nice, c-cup breasts and an thin, hourglass shape. Her breasts sagged a little, but they still looked good in here bright yellow bikini top. I couldn't stop looking at her. I always thought of her as a second mother, but my perception of her changed that day and I began lusting for her. I couldn't explain why, but I did.
After Jessica sat in the lounge chair, she reached over to a small table, next to her and grabbed a bottle of sun screen. I watched her spread the white, creamy lotion on her shoulders, arms, chest, stomach and legs. It was a good thing I had sun glasses on. I continued my conversation with my friends, but my eyes never left Jessica. Once she was done spreading the lotion over her body, she sat back in her chair, put on her sunglasses and laid back to soak up the sun's rays.
About an hour later, Vanessa left the pool, to get ready to go meet her boyfriend. She walked over to her mom, said a few things to her and gave her a kiss on the cheek. Jessica sat up and asked us if we wanted some lunch. John and his girlfriend said yes and they got up to go in the house to change out of their bathing suits. They said they
would go grab some take out for us. I decided to stay in the pool for a while longer. After everyone left, Jessica got up from her lounge chair and looked over at me.
"How's the pool Anthony?"
"It's great Jessica." I replied, staring at her behind my sunglasses. John's mom had always insisted I call her by her first name.
"Good. I need to cool off a bit. The sun is hot today."
Jessica walked over to the diving board and plunged into the pool, head first. When she emerged from the water, she swam over to the shallow end, where I was standing.
"Have you talked to your mom?" She asked when she approached me.
She stood up, looking at me and waited for my reply. My eyes just moved down to her breasts. The water was glistening off her smooth, tanned skin.
"Not since yesterday morning." I replied, forcing myself to look up at Jessica's face. I noticed a slight smile.
I felt my face get very warm. I wasn't sure if I was blushing or it was the sun making me get hot. I hoped she didn't notice me looking at her chest.
"Well, I spoke to your mom this morning, before coming out to the pool. She told me she needed to stay away on her business trip for a couple of extra weeks, so it looks like you will be spending some extra time here. She said she would call you tonight with the details."
"Ok." I said. Still feeling embarrassed at the idea that Jessica may have caught me looking at her breasts.
"You are not very talkative today Anthony. You feeling OK?" She asked as she splashed some water in my face.
I started laughing and splashed water back at her. Jessica was always cool with us kids. She was 45 years old, but she acted like she was 20 sometimes. She was very playful and very full of energy, especially since she had lost all her weight.
"I'll race you to deep end and back. Loser has to take a cold shower in the outdoor shower by the cabana."
Then she splashed me again in the face and took off, swimming toward the deep end of the pool.
I tossed my sunglasses over my head and swam as fast as I could after her. The outdoor shower had no hot water and it was always cold. I hated cold showers. Jessica and I reached the deep end at the same time, and raced back toward the shallow end. I was captain of the varsity swim team at school. Even though Jessica had a big lead to start, I easily caught and passed her, beating her by several strokes to the end of the race. I got out of the pool and stood at the edge, with my arms crossed, looking down at her. She reached the end and looked up at me, breathing hard.
"What took you so long?" I asked, teasing her.
"Funny guy." She said sarcastically. "Help me out of the pool." She demanded, extending her left arm up at me.
I bent over to help pull her up, but instead, she grabbed my arm and pulled me in. I dove right over her. When I came up, she was wading through the water, toward the ladder to climb out. I chased after her and reached the ladder as she stepped up on the last rung. I looked up at her and saw her bikini bottom wedged in between the crack of her round ass. I could see the tan lines where her skin went from bronze colored to almost milky white. I also saw something else I didn't expect. I saw a slight patch of dark, pubic hair sticking out of the left side of her inner thigh.
"That's what you get for not letting me win!" She exclaimed as she laughed, running over to the shower by the cabana, while pulling her wedgie out of her ass.
I climbed up the ladder and ran after her. She turned on the shower and put her hand under the running water.
"Fuck!" She squealed. "This water is cold!"
I put my hand under the water to feel how cold it was. She was right. It was really cold.
"Karma is a bitch Jessica." I said as I grabbed her and pushed her under the water.
She squirmed and tried to pull away, but I held her tight. It felt nice holding her body
against mine as she squirmed and pressed up against me. At one point, I wound up behind her with my arms wrapped around her waist and my crotch pressed up against her ass. Oddly enough, Jessica didn't struggle to get free as much when I was pressed up against her. It actually felt like she was pressing her hips into my crotch. My heart beat sped up and I felt my manhood swell up a bit. I pulled away from her because I didn't want her to feel me get hard.
"We made a bet and you lost. Get in the shower Jessica, before I lose all respect for you." I joked with a chuckle.
"Fine, but I will pay you back for this."
"Yea, yea. You are the one who bet me and lost."
Jessica gave me a puppy dog frown and walked under the shower head. Her whole body quivered and she squealed as the cold water hit her skin. I just stared at her and admired her body. Her nipples started to protrude from her bikini top and I could see goosebumps pop up all over her skin.
"Don't just stand there staring boy, go grab me a towel!" She exclaimed in a high pitched voice.
I laughed and walked into the cabana and grabbed a towel.
"Here you go Jessie." I said calling her by her nick name.
She jumped out from under the shower head, grabbed the towel, and wrapped her self in it. She was shivering where she stood.
"Oh my God, this towel is so warm." She said, a look of ecstasy on her face.
I walked over to the shower and turned the water off. Then I went into the cabana and grabbed 2 more towels. I walked behind Jessica and put a second towel around her shoulders.
"I already have a towel around my shoulders dumbass." She said defiantly, obviously annoyed that I made her pay the consequences of losing our bet. "Wrap that towel around my waist."
I stood in front of her, reached around her waist, grabbed the towel from around her and brought the 2 ends of the towel to her belly button. I tighten the towel around her and slipped one end in behind the other, my hand pressed between the towel and her lower abdomen. An image of me unwrapping the towel and taking of her bikini bottom popped into my head and I felt my manhood swell again. A let go of her towel and quickly wrapped the other towel I grabbed around my waist. I noticed another smile on Jessica's face.
"I'm going inside to take a shower. John and Josie should be back soon with lunch."
Her voice snapped me out of my fantasy world and I walked into the house behind her. She walked toward her bedroom and I walked toward the guest room bathroom.
