His Dream Vacation

Melissa was my best friend since we were in grade school. I was an only child and she has always been the closest thing to a sibling that I have. After high school we both went to the same college in Huntsville, TX.

Her majoring in business and me criminal justice. She was very conservative. The prim and proper lady.

I was the wild one. I had plenty of partners in college. Guys and the occasional girl. She would always call me a little slut and we'd both laugh. It actually turned me on a little.

After college we both moved back to the Houston area. Her taking a job in the administrative office for the locale school district and me landing a job with one of the biggest police departments in the country.

As the years went on we stayed friends. Talking everyday and seeing each other a couple of times a week.

My name is Kelly. I've had a few long term boyfriends, but never married. My career took up a lot of my time. Even now at 51 years old I'm proud to say I still "got it." I'm 5'9" with dark hair and green eyes. I workout 5 days a week. I have a toned athletic body, with firm 36D tits and an ass that you can bounce a quarter off of. I take lots of pride in how nice my ass looks. Especially in a short skirt or tight pair of jeans.

Melissa, married a few months after we graduated from college. She met Chris while we were out one night having a few drinks, during our second year of college. He is a very good guy. After 25 years of marriage he still treats her like a princess. They have 2 children. A daughter name Lauren, who is 22 and away at college. I miss her and still talk to her at least once a week. They also have a son name Jacob. Who recently turned 18. He has always been my baby.

Since I never had kids I was very close to Melissa's kids. It was rare that I missed a choir concert, school program or football game.

Jake, loved being around me. As a little one he loved seeing me in my uniform. He always asked if was taking bad guys to jail. I always assured him that I was. He would ask to play with my cuffs. He has called me Kell Kell since he could talk. Even when he got older he'd make sure I was gonna be at his game on Friday night. Since his sophomore year he had been the starting linebacker on his high school team. Now as a senior every college in American was recruiting him.

Jake had grown to be a gorgeous young man. Standing 6'5" he towered over everyone. He also weighed 230 lbs and was a solid rock. He was the sweetest guy ever. He was friends with everyone. He didn't care who it was or what social level they were on. He went out of his way to make the less popular kids feel like they were just as important to him as his own teammates.

I always found it kind of strange that Jake never brought any girls around. Obviously every girl he knew would like him. I asked on occasions if he had a girlfriend or if he had any dates lined up. He always kind of shyly laughed and told me no. I could always tell it made him a little uncomfortable.

It was a few weeks after Jake's 18th birthday that it all started.

I had a conference to attend in Florida. I went almost every year. Since Jake was little he always asked if he could go. I always told him when he got older and I didn't have to babysit him the whole time then he could. When Melissa told him I was going this year, he immediately texted me.

"Hey Kell Kell!! Am I old enough for the Florida trip yet?" He asked. "It is during spring break." He assured me.

I had a feeling he'd be asking this year since he asked every year. I was prepared and had already decided I was gonna let him tag along this year.

I said "I think this is your lucky year, Jakey!"

He was so excited he called and asked if I was serious. I told him of course I was and that he needed to get packed because we would be leaving in just a few days. I told him to pack enough for a week and plenty of beach clothes. I always spent lots of time on the beach while I was there. Since the conference was only for the first 2 days. I knew we'd be at the beach a lot.

I showed up at Melissa's Monday morning to pick up Jake. He was ready to go as soon as I got there. Melissa and I talked about the week to come. I told her that I'd take good care of Jake. She knew I would.

Jake and I descended for the airport.

The flight was good. I could tell Jake was Nervous about flying. So, I bought him I few screwdrivers on the plane. As he drank I could tell it made him braver. He started to ask about my love life. Why I'd never been married. If I had a boyfriend. Then, he asked if we could pretend that I was his girlfriend on this trip. I thought he was kidding. So I told him, sure.

Then I asked "Are you sure you want to pretend like an old lady like me, is your girlfriend?"

"Old lady?" He asked

"Yes, I'm a few months older than you're mom." I told him.

I could tell he was a little tipsy. He was getting brave. He told me "Kell Kell you are the hottest woman I know!"

I was taken back a little. I'd never had and 18 year old tell me I was hot. I laughed and squeezed his leg. As I laid my head on his shoulder.

"Well, thank you! You little stud. You're a little hottie yourself." I said to him.

I could feel myself gettin getting hot. Was I really getting turned on by an 18 year old? I watched this guy being born. I never missed a birthday party or a football game of his.

I had been with a few younger guys. Just a few months ago, I took home a 21 year old that I met at work. He was a rookie officer. He wasn't all that great, but thought very highly of himself. And not willing to learn. So, it was a one time thing.

I left my hand on his leg for the remainder of the flight. When we got off I held his hand as we walked to get out bags. We took a cab to the resort. It was beautiful like always. We made our way up to the suite.

When we got in the suite the first thing he noticed was the spa in the middle of the living room. He asked if we would be using it while we were there. I just smiled at him.

I told him we should get showered and head down to the beach. He said he'd shower after me.

I was still hot from the flight. So I decided on a cold shower. I washed up not wanting to take too long. Wrapping myself in one of the robs hanging there, I let him know that I was finished.

He passed me and said "Ok thank you, baby..."

I just smiled at him as I ran my nails across his muscular chest. I couldn't believe how much I was turned on by him calling me baby.

I decided we'd just stay in. I called down to the desk and asked them to send up a bottle of Grey Goose and champagne on ice. I walked back into the master bedroom. I let the robe fall off my shoulders and onto the floor. I looked into my suit case and found the red bikini I brought for the trip. I strapped on the top. Adjusting the triangles to cover my light pink areola's. Then I pulled the bottoms up my legs and over my hips. Covering the small patch of hair on my mound. I adjusted to triangle in the back and looked at my firm ass (only covered by a thong) the mirror. I don't usually wear a thong bikini, unless I'm in Miami where it's very common.

About that time I heard a knock at the door. I opened to a younger girl that seemed to be take back by what I was wearing. I chuckled for a second, then moved to the side letting her push the cart inside. I was glad that she brought strawberries, since I forgot to order them. I knew I had set ups at the bar. I gave her $10 and told her thank you.

When I turned around Jakey was standing at the end of the hall staring at me with his mouth almost on the floor. I laughed and asked "Are you ok, Jakey?"

He snapped back to reality and said "Yes, of course." Trying to act like he wasn't checking out my ass.

I asked "Well, do you like your girlfriends bathing suit?"

He just nodded his head.

Then I told him "It's about to be getting dark. So, I thought we could just hang out in the jacuzzi."

I walked over and took the top off the jacuzzi it was already hot and I turned the air on. I asked "Would you like champagne or what you were drinking on the plane?"

"I'd like another screwdriver." wass all he said.

I headed to the bar and poured him a stiff drink. I also poured me a glass of champagne.

I headed to the jacuzzi setting his drink on the said then getting the champagne that was on ice and set it beside his drink.

I climbed up the steps and stepped inside. The water felt great. I closed my eyes and sank down to my chin, feeling the jets all over my body. When I opened my eyes Jake was stepping inside. He had to have the nicest body of any man I'd seen. I guess all that working out did him real good.

I smiled and came up. "Your drink is right there." I said.

"Thank you, Kell Kell." Was his response.

I could tell he was nervous. It was making me so horny. So, I asked him "Jakey, would you like to play a game with me?"

Looking at me strangely he said "Sure, what game?"

I said "Truth or dare?"

Not knowing what to expect, he said "Truth"

I went right for the kill. "Are you a virgin?" I asked.

The look on his face said it all, but I could tell he thought about lying. Then, he said "Yes"

"You ask me now, Jakey" I instructed.

"Uh truth or dare?" He asked

"I'll go with truth this time." I said

"Ok. Does champagne taste good?" He asked

I giggled a little. I said "Yes it does. You may try it if you'd like."

"Not now." Was all he said.

"Truth or dare?" I asked

"Truth" he said

Standing up out of the water on a bench to where I was knee deep in water, I asked

"Do you think my ass looks good in this thong?"

His eyes almost bursted out of his head. He said "Yes ma'am! It's very nice."

"Aww thanks Jakey!" I told him. As I got back in the water and scooted next to him.

"Truth or Dare" he ask

"Dare" I said

"Uh I dare you to. Uh I dare you to take your top off..." he said very nervously.

Without saying a word I stood in front of him. Reached behind my neck and untied the top. Letting my tits come into view for him. He just stared as I reached behind my back and untied. "Like what you see, Jakey?" I smiled

"Yes ma'am" he said. Still stunned.

Staying there I asked "Truth or Dare?"

"Dare" he said quickly

Sliding onto his lap, straddling his waist, I said "I dare you to let me show you what a real woman can do, Jake."

Grabbing his face with both hands I guided his lips to mine. I pressed my lips to his, then slowly opened my mouth letting my tongue touch his lips before he opened his mouth letting me enter. He took to it quickly. Our tongues started to aggressively wrestle around.

I started to grind my panty covered pussy over his hard cock. I reached down to take hold of it and to my surprise it was already out of his shorts. I laughed "You naughty boy!! You were already playing with him under the water."

He just smiled.

I raised myself pulling his head to my left tit. "Have you ever sucked on titties, Jakey?" I asked him.

"No ma'am." Was his response, as he started to suck mine like he was trying to suck my whole nipple off.

"Easy there tiger!!" I told him with a laugh. "It's not about how hard you can suck.

"Suck lightly, then run your tongue around my nipple." I said

He did as he was instructed.

"There you go, baby. That feels great." I told him.

"Don't leave the other one out." I said

He was catching on really well. I thought about sitting up on the side of the spa and teaching him how to eat my pussy, but fingered I'd do that later. "We have 7 nights here." is what I thought to myself.

I pushed off him. Going under water I pulling the sides of his trucks, as he easily lifted. Letting me slide them off. Then I stood up out of the water and looked at him seductively as I untied the strings holding the sides my thong together.

I then climbed back on his lap. I took hold of his big cock and guided it to the opening of my pussy. Lowering myself onto him. He felt amazing.

He let out a grunt as I started to slowly work my hips. "How does this feel, Jake?" I moaned into his ear as I nibbled on his neck.

"Better than anything I've ever felt, Kell Kell." He said back.

I started bucking hard as I felt my orgasm about to hit and it did like a ton of bricks. "I'M CUMMING JACOB!!" I screamed as I ferociously slammed down on his throbbing cock.

"Me too, Kell!!" Was all he said as I felt jet after jet of his young hot seed shoot deep inside my love canal.

"Ohhh yes, baby!! Give it all to Kell Kell!! Give me all your young cum, Jakey!!" I screamed as I dug my nails into his shoulders, trying to remember if I'd ever cum so intensely.

I let out a few deep breaths as I started to slowed my pace. Still moving my hips till I milked everything out of his cock.

I came to a stop. Looking in his eyes. I told him how great he felt, before locking my mouth back onto his.

He broke the kiss and asked "So, was this just a one time thing, Kell Kell?"

"One time thing?" I questioned sarcastically.

"We're here for 7 days, Jakey. I'm gonna teach you everything there is to know, baby." I assured him.