Kelly and I were really sick of winter. It felt like it snowed every weekend. We weren't able to get out as often as we wanted and had a serious case of cabin fever. We decided to book a vacation in southern Florida on a beach for 5 days.
We flew down on a Wednesday night, so we didn't have to burn as many vacation days. As we got out of baggage claim and stepped out to go get our rental car, the warm 70 degree night time air felt wonderful. Looking at the palm trees, we immediately felt better.
The hotel where we had booked a room was right on the beach. Our plan for the vacation was simple. Eat out, booze it up, have sex, and park ourselves in beach chairs for 5-6 hours a day.
We checked into the hotel and were ecstatic to get a room on the 15th floor with a balcony overlooking the beach. Perfect! We unpacked the bare minimum, when Kelly said, "I could really use a shower. You wanna join me?"
I immediately got undressed, and my dick was already at 3/4 mast before I even joined her in the shower. Once I got a look at her magnificent and all natural 36DD breasts, I was at full mast.
Kelly grabbed the soap and started lathering my erect penis, chuckled and said, "Well...that didn't take long."
We washed each other up. I spent extra time lathering up her huge tits. I turned her around, reached down and played with her clit as my cock was pressing on her shapely ass. Kelly had been hitting the gym hard all winter long and it showed.
She turned around, jammed her tongue into my mouth and said, "You're so hot. I need you to fuck me."
Standing up, I inserted my cock into her pussy and fucked her. It didn't take long for me to come inside her. I came first, but towards the end of my orgasm, she came, letting out moans of pleasure.
We got out of the shower and dried off. Tired, we didn't bother putting any clothes on. We climbed into bed naked.
Next day, we slept in a bit, got out on the beach around 11:00. It was beautiful, sunny and 82, and the 5 day forecast looked just like that. We were going to have a kick ass vacation.
After several hours, we'd had a few beers and were facing the water, people watching, checking them out as they walked by. There were old men with big bellies in Speedos, saggy women with bikinis on. Occasionally we'd comment on something that was particularly funny.
What we started to notice was the number of women who looked between the age of 40-45, all made up, big fake boobs, with older guys in their late 60's-early 70's.
I sat there commenting to Kelly, "There's a trophy wife with fake tits." or "His wallet must be fat for her to be with him."
After seeing about 4 of these women in this situation, I just shook my head and said, "I know I'm generalizing, but women are a bunch of gold diggers. There is NO WAY they find these rich old guys attractive."
Kelly said, "If we ever got divorced, I could see myself doing that."
I said, "Get out of here. You'd actually stoop to being a trophy wife?"
She said, "Why not? It beats working. I could be down here, nice and tan, access to as much money as I want, without a care in the world."
"What about attraction? What about having to fuck them? Wouldn't that be an issue?"
Kelly laughed, "Even with Viagra, how often can these guys get it up? They probably fuck these girls once a month, tops. That said, there is something attractive about a distinguished, rich, and successful older man."
"So you'd fuck an old man because he's rich and successful?"
"Sure." Kelly grabbed another beer out of the cooler and took a sip.
I gave her a skeptical look and said, "Hypothetically, if we're out, I tell you to find an older guy to fuck, you'd be on board?
"Yeah" she said sheepishly. "I am attracted to older men and have never fucked anyone who was that far out of my age group."
We went back to the room, showered and went out on the balcony for a cocktail. I still couldn't wrap my arms around this concept and didn't believe her. As usual our kinkiest thoughts and ideas were when we were buzzed from alcohol.
I said, "You feeling dirty?"
Kelly reached and touched my cock through my pants and said, "Of course."
I said, "I don't know why I'm suggesting this, but you have me really curious. What if after dinner, we go to that high end restaurant, we'll do the old, 'Let's sit apart at the bar, and see what happens.' routine. I'm wondering if you're really serious about finding older, rich guys attractive."
Kelly raised her eyebrows. "You don't believe me."
Me, "No"
She said, "Ok, lets put your money where your mouth is. If I find an old, rich guy who's attractive, you gonna let me fuck him?"
I said, "If that's what you want to do. As usual, I expect the play by play afterwards.
Kelly said, "Sure. What are you going to do?"
"Maybe I'll find some loose woman to fuck."
"If that's what you want to do, go ahead. Hope you catch the clap." she responded sarcastically.
"If I do, you'll wind up with it too!"
Kelly rolled her eyes.
Kelly went in and changed her clothes. She put on a black dress that hugged her frame nicely. The dress showed just a little bit of cleavage. Enough for men to know that her boobs were big, but not too much where they were spilling out to where she was begging to be taken home.
We had a few more drinks at dinner, we ate lightly, salads with steak tips. We left the restaurant and headed over to the upscale place, where the bar was half full. I went in first, and grabbed a seat toward the far end of the U shaped bar, that gave me a view of the door and the entire bar.
Five minutes later, Kelly came in and ordered a drink. She nursed her drink for a while. I was actually wondering if this were going to happen. Inevitably, a silver haired man entered the bar and sat next to her. He looked late 60's, neatly dressed, very tan, a little bit of a gut, but he had on a bracelet on one wrist, rings on both fingers and had the aura of someone with money.
Kelly struck up a conversation with him and it seemed to be going well. I ordered another drink watching as the gentleman ordered a second high end single malt scotch and there was no lag in the conversation.
After about another 45 minutes, Kelly nodded her head and they got up and left.
I thought to myself, "She's really fucking serious about the older man fetish."
I finished my drink and took an Uber down the street to another bar.
It just happened to be Karaoke Night. I am a good singer, having been the lead singer and rhythm guitar player in a band in my 20's that was booked every weekend. I got up on stage and nailed "Don't Stop Believin'"
As usual, my singing attracted female attention. A woman about 10 years younger than me came over. She introduced herself as Brenda. She was ok looking, wearing a sun dress, but could have stood to lose 25 lbs. She began talking to me and asked me about my singing skills.
We walked over to the bar and I bought her a drink. We decided to stay there, grabbed two seats and talked some more. Brenda was flirty and continuously kept touching my forearm. Getting the hint from her flirtiness and now obvious intoxication, I decided to make my move.
"Hey, what do you think about going outside to your car?"
We took our show outside to the car and climbed in her back seat. Fortunately, her car was parked near the back and not near any others.
We kissed for a few minutes. Then I pulled her dress straps off her shoulders and fondled her breasts. I unhooked her bra and pulled it off. They were ok sized, C cups, not close to the stratosphere of Kelly's gargantuan mammories. I then pulled her underwear off and began fingering her pussy. That region of hers wasn't well groomed, another thing I wasn't used to.
Brenda unzipped my fly, and undid my pants, pulled my hard cock out and began stroking it. Her technique was excellent.
