In the summer of 2015, just after my 18th birthday in June, my parents allowed me to take a vacation with my boyfriend and his dad. Dan's parents split up when he was very little and he has lived with his dad ever since. Like me, Dan is an only child. We met in high-school; we are the same age and have been together for three years. My parents are good friends with his dad so there was no problem when they invited me along.
Dan's dad had rented us a two bedroom condo in a place called the Coconut Mallory in Key West Florida. It was a condo on the upper level so it was a two story with a kitchen, dining room, living room open floor plan that opened onto a spacious balcony porch with outdoor furniture on the first level. The two bedrooms and the bath were on the second floor with a spiral staircase that led up. As one might expect, everything was beautifully furnished in whicker and pastels that invoked thoughts of the tropics and the beach.
When we first arrived and went up to the bedrooms, I thought maybe Dan's dad would insist on me having my own room and Dan and him take the other. To my surprise he said, "I guess you kids can have the front room and I'll take the one in the back." But then Dan's dad is no idiot, has always been realistic and remembers what it's like to be young. Not to mention, he walked in on me and Dan fooling around on the den sofa one afternoon when he unexpectedly came home from work early. Surprisingly he didn't tell my parents and now, after offering Dan and I to share a bedroom, he just winked at me and added, "Just don't tell your folks; okay?"
The first day, Dan's dad seemed to be content with lounging by the shared complex pool or drinking beers and sitting on the balcony porch. He let Dan and I take the car to go exploring. We'd heard Duval Street was the happening place and I really wanted to lie in the sun on a beach. I saw online that there was a beach on the southern end of Duval Street called South Beach (not to be confused with the famous one in Miami). Under my shorts and tank top, I had on my little white string bikini. Dan really likes it when I wear this one because the white fabric really shows my nipples. Also, I keep my pubes trimmed into a triangle above my clit with my vulva shaved on both sides so the tight fabric of my white bikini bottoms really shows my camel toe. Dan wore his swim trunks, a T-shirt and the Pittsburgh Pirates ball cap that seems to be a permanent part of his skull and we set off for the Key West version of South Beach.
Okay, I have to admit, I was a little disappointed when we reached South Beach. It was much smaller than I had imagined and there was a lot of dead seaweed that had washed ashore separating the sand from the water. But there was a really nice bar/pub style eatery there that was in a building open on three sides and there were plenty of hot bodies broiling in the sun on the beach; some on beach chairs with umbrellas and some just lying on towels in the sand. Dan and I rented two beach chairs and headed out onto the strand with our bag filled with suntan lotions, towels and water.
As we were setting up our carefully selected spot on the beach, I couldn't help but notice many of the women were sunbathing topless. I was surprised at this as I had never given any thought to semi-nude beaches before much less experience one. Once I stripped off my shorts and top and Dan removed his shirt, we lathered up and settled into our lounge chairs; sunglasses in place.
I thought about what it might be like if I went topless. Not that I would ever dare, I mean, Dan is extremely jealous and would probably get upset with me. In fact, I am surprised he let me where this bikini out in public. When I first purchased it two years ago, he told me he would prefer I only wore that for him and not at the public pool in our hometown. Apart from showing my nipples and camel toe, the fabric barely covered my privates. Besides, I am very shy and would never be able to expose myself to an entire crowd of perfect strangers. But, for some reason, the thought really excited me.
During the few hours we lounged there, I noticed several men; from boys to full grown men, giving me the once over with their gazes. Of course, I had always noticed the way men look at me at the pool or the Waterslide Park at home but I had never given it much attention. I do not think I am ugly but never considered myself to be anything more than average. I have a thick head of honey blonde hair that is styled to reach just the tops of my shoulders, bluish/gray colored eyes and peaches and cream skin. I hadn't had the opportunity to sunbathe much this summer so I had almost no tan; in fact I was planning to correct that oversight on this vacation before college began in August. I am only 5 foot 4 inches tall, weigh 95 pounds (I'm the girl most other women hate. I can eat anything and still remain thin) and my breasts are only a 'B' cup but are nice and perky with small, pink nipples that stick way out when I am excited. Like now, when strange men are staring at my body. A phenomenon I never paid attention to until now.
It wasn't long before I began wondering what it would be like to remove my top and give these men on the beach something real to gawk at. I noticed many of these men were there with their wives or girlfriends and even those I saw alone were wearing wedding bands. For some reason, I got really excited at the thought of someone else's boyfriend or husband getting turned on by seeing my naked breasts. I am just about always wet down there and now I could really feel the urge growing inside of me. I knew it wouldn't be long before I need to have sex with Dan.
Dan; I was getting so into being ogled by other men that I'd completely missed the idea that we were surrounded by bare boobs and I was there with my boyfriend. What is he doing right about now? I glanced sideways at him so as not to turn my head directly towards him, alerting him to the fact I was watching him. To his right were two women I'm guessing were in their thirties. Both of them beautiful and both were topless. The one closest to Dan was very tan, long brown hair, blue and white flower print bikini bottoms and huge boobs! Her friend was attractive too with short, light brown hair, yellow bikini bottoms and boobs that were probably smaller than mine. They were obviously friends and were chatting away, not paying attention to the fact that my boyfriend was openly staring at the one with the huge boobs from behind his sunglasses.
I guess the normal reaction would be for me to be jealous; but I wasn't. For one thing, I really dislike when Dan is jealous of me and I have never personally had any use for the emotion. It makes me feel like I'm his property and not his girlfriend. For another thing, now I had the perfect excuse to stare at the bulges in the swim trunks of the men who were ogling me and fantasize about what it would be like to have sex with someone other than Dan. Oh yes; I have those fantasies. He is the only sex partner I have ever had so I guess it is normal to fantasize about being with someone different. But it is just a fantasy; not to be acted upon. I'm sure other women fantasize about men they cannot have too; especially those who have been married for many years. I cannot even imagine what that must be like.
We got back to the condo around 5 pm There was a note on the kitchen table telling us Dan's dad had taken a cab to Mallory Square for sunset festivities and some tropical drinks. There was a microwave pizza in the fridge for us to eat. He said he'd be back around 10 o'clock unless he found a nice lady to take him in (little smiley face drawn next to that line). We read the note together then looked at each other with mischievous grins. We were both charged up by the sights and bodies at the beach today so we were both thinking the same thing. "I'll go get the condoms!" he said as he charged up the stairs to reach the condoms in his travel bag. Before he hit the second step, my bikini was already on the floor and I was sitting on the whicker loveseat with my legs spread wide. I tested myself with my finger and, as I expected, I was positively dripping. I kept thinking of the men on the beach glancing at my body and my bikini covered mound. Soon Dan reappeared, already naked, already hard and his latex covered cock bouncing in front of him as he hurried over to me.
There was no foreplay on the first go around. We were both too hot and bothered. I leaned into the back of the loveseat; spread my legs wide and used fingers from both hands to hold my dripping hole open for him. Dan just knelt down on the floor and buried his cock deep inside of me. I think our sex that afternoon was the fastest since our very first time. I am a fast cummer and used to multiple orgasms but I only got in one before Dan got his. I giggled as he pulled off the condom and then dumped the contents onto my boobs and belly. Then he ate me out with more enthusiasm than he has ever shown before. I wanted to ask him if he was so turned on because of the big boobed woman I saw him ogling at the beach but I didn't want to ruin the mood by making him upset, so I just enjoyed myself.
Between 5 pm and 9 pm we had sex on just about every surface in every room of the condo. We even did it once on the balcony porch; bikini on, just pulled to the side. When Dan's dad got back, I was glad to see he had a little too much to drink and only said goodnight and wandered up to his room. Though Dan flushed all the condoms down the toilet, the entire place had that musky odor of fresh sex. I'm sure his dad knew what we'd been up to anyway.
Day two was just about a repeat of day one. We did lie on the beach at South Beach, I did ogle the men who were ogling me and Dan was staring at the women thinking he was being sly behind his sunglasses and I wouldn't notice. But we also did some browsing of the shops and bars along Duval Street and Front Street. Dan bought me lunch at a place called the Roof Top Café on Front Street that was really nice. It felt like dining alfresco on a roof top that was also a tropical garden.
