The Valentines Vacation

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Clothing Optional by eekk (edited version)

This a true story from a couple of years ago. My wife, Diane, and I (my name is Dan, by the way) decided to make the drive down to Key West to celebrate valentines day. We left immediately after work and decided to drive all night to the hotel. I had my usual work clothes on (jeans and a polo, had on her black skirt, nylons and a nice blouse). Believe it or not Key West in February is a nice 70 degrees during the day. Now I should preface this by saying that I have a small penis. It’s about four inches erect and a little turtle head while soft. My wife is about 5’7″ with b cup breasts and a nice big ass. I am 6’1″ and of average build. We both share a small penis humiliation fetish.

We stopped in at a bar that sat right before the actual keys to get directions, and use the ATM. The bar was dark with lots of neon lights and there were a few people scattered around. We made our way to the bar and I started getting directions from an older, albeit attractive bartender. Being a young couple (26 and 25 years old), it wasn’t long before a large muscular man in a sleeveless shirt took notice of this and took a seat next to Diane.

They started to make small talk but I was busy trying to get directions and repeatedly getting distracted by the bartenders cleavage to notice what they were talking about. Just then I felt a petite hand creep across my crotch and begin groping me through my jeans. My wife has always been really kinky but this for some reason surprised me. I pulled up a stool and sat down. Her hand closed around my balls and started to squeeze. She leaned over and whispered that she would wait for me in the car.

I talked to the bartender for about another fifteen minutes (just long enough for my boner to go down a bit) and made my way back to the car. Once we were back on the road my wife shifted sideways in her seat to get comfortable and rested her feet in my lap. We made small talk and after a while she started to really rub her feet against my cock and balls through my jeans.

“Do you know what that guy in the bar talked to me about?” she asked.

“No, what?”

“He asked if you were my husband. When I said ‘yes’, he said he bet he had a bigger dick than you.”

My cock was throbbing against her left foot as her right rubbed a bit more intensely against my balls.

“I told him it probably was and he offered to show it to me.”

I started to unzip my pants and her left foot pushed my hand away.

“Little Dan doesn’t get to come out yet… I told him not to take it out but just describe it to me. He said it was ten inches and very thick… Hmm… That’s more than twice the size of your little wiener, isn’t it?”

I was completely on the edge and about to cum when she removed her feet from my lap and announced she was tired and going to try to take a nap.

The rest of the drive was agony. We made it to the hotel at about midnight and we got changed and ready for bed. She was sitting on the edge of the bed in her nightshirt and I walked up in my pajama bottoms to kiss her Goodnight.


Later that night she asked, “You’re not mad at me about that little tease earlier are you?”

“No, never. I love it when you tease me, you know that.”

“I know, sometimes I think I’m too mean though.”

“You could never be too mean. I love you.”

“I love you, too. Are you starting to get hard?”

Her gaze was now my groin and mine followed. I was starting to get a little bulge going. Her hand reached up and began to massage my balls through my pj’s.

“Were you thinking about my little tease, me talking to that guy about his huge cock or the bartenders cleavage?” she asked.

“Mmmm… You noticed that, huh?”

“Uh-huh, your little dick would have disappeared between those giant things.”

She lowered my pajama pants and told me to stroke it for her. She then told me about how she should have taken the chance to see the big one when she had it. Next she scooted back on the bed and pressed her foot into my balls. After a couple of minutes I started to groan heavily and she told me to cum on her foot. I shot a huge load all over her toes and up her leg a bit. Afterwards we cleaned up and finally went to sleep.


The next day we wandered around Key West (me in loose-fitting shorts, a t-shirt and sandals. My wife had a knee-length flowing skirt, a tube top with no bra and flip-flops) taking tours and hitting local tourist traps. In the late afternoon we noticed a sign on the side of a building that read “the Garden of Eden.” Curious, we followed the sign up the steps to the roof of another bar. To our shock, this bar that sat on the roof of another bar was clothing optional! There were several older guys walking around completely nude and a topless bartender with gigantic breasts who looked like she was in her mid thirties.

We sat at the bar and had some drinks, my wife couldn’t help but gawk at all the exposed penises and loved pointing out the really big ones to me. After a while I excused myself to the restroom and when I came back my wife was in the middle of the room and chatting up some of the locals. I made my way back to the bar and made small talk with the bartender, all the while she was giggling.

“I’m sorry, what’s funny?” I asked.

“Your wife told me about you.”

“Oh… What did she tell you?” I responded nervously.

“You know, about your ‘LITTLE’ problem.”

Just then a couple of twenty something girls in bikinis walked in and sat next to me. One looked to be about 5 feet even with strawberry blond hair and a flat chest. The other was a brunette and looked to have c-cup breasts. They took a seat next to where I was standing.

“Look, it’s not that bad, she just likes to exaggerate.” I assured her.

“Really, ’cause she said you just have a little nub for a dick.” she shot back.

The two girls next to me heard and started to giggle while looking at me then back at each other.

“That’s not true! I mean, it’s not huge but it’s definitely not small!” I almost yelled.

“Oh really!?” said an all too familiar voice behind me. Just then a pair of petite hands gripped the sides of my shorts and boxers and whipped them down to my knees! The girls next to me burst out laughing and one of them gave the small penis sign with her thumb and index finger. The bar tender jumped and leaned over the bar and exclaimed that her nipple was bigger while laughing.

In a rush I tried to pull my shorts and underwear back up but my wife was still squatting behind me and was pushing them to my ankles. After a while I just gave up. One of the girls tom my left said it looked like a cocktail wiener, and I started to get a bit erect. My wife stood up and told them if they kept making fun of it would only get bigger.

The comments seemingly came from all angles: my little brother is bigger than that; it’s like a little shrimp; oh my god it’s only like five inches! “Worse,” Diane said, “It’s only four!”

With that she grabbed my pin dick and started stroking. The brunette girl to my left asked if something that small can cum and Dane said yes, but he might need a little help. The girls look at each other, then back at Diane.

Diane lowered her tube top and exposed her erect nipples. The girls sighed and lifted their bikini tops up over their breasts. It was all too much and I couldn’t help but shoot a huge load all up my wife’s arm. Later we went back to the hotel room and she made me fuck her while telling her about all the other dicks she saw there.

The End

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