Taboo Summer Love

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.

That night we all went together to Mallory Square for Sunset Festival and watched the acrobats and the sailboats drifting by, some were shooting off fireworks like the 4th of July. Dan and I had to confine ourselves to sex in the bedroom that night but it was still good and I was still fantasizing about the boys on the beach.

When I woke on the third day, Dan and his dad were sitting at Dan's laptop looking at some website called Fins & Feathers. It is a website for deep sea fishing. They told me they were considering going deep sea fishing for sailfish (whatever that is) and asked if I'd like to go too. I told them that I can't go because I get sick from the motion on a boat but I wanted them to have some father/son time on this vacation and I would be fine being alone. In truth, I was hoping to have some alone time at South Beach to test my bravery and see if I could or would actually expose my breasts in public. The idea had been growing in my mind ever since the first day and the eroticism of it all was almost overwhelming me.

After they made certain that I was fine being left alone for a day, Dan's dad used his cell to call the charter boat service and book the excursion for the very next day. The only problem was, the boat service left from a few islands back up highway 1 so they would need to leave early in the morning and take the car. The Coconut Mallory is on the wrong side of Key West from Duval Street and all the fun activities. But Dan's dad resolved that problem by offering me money for taxi service and some spending money as well. In fact, he was quite generous. He also left me a number for Maxi Taxi which I programmed into my phone.

The next day Dan and his dad left out early in the morning. I think it was around 4 am? Dan and I had just enough time for a quick screw while his dad showered and then they were gone. I woke around 6 am, showered and shaved everything from head to toe, leaving just the triangle of reddish blonde pubes above my clit. Then I pulled out a bikini Dan doesn't know I have. It is also white but the bottoms are thong and the material is so thin it is semi-transparent when it gets wet; not that I was actually planning on getting into the water. In short, they leave little to the imagination. When I put them on, I almost changed my mind. I had never worn a thong, not even my underwear has ever been thong and, at first, the feeling of a string running up my butt crack was anything but comfortable. But I eventually got used to it and decided to give it a try. I threw my other bikini in my bag with the lotion just in case I got uncomfortable or chickened out at the last minute.

I ate a bowl of cereal then called Maxi Taxi. I pulled on some shorts and a tank top over my bikini, put on some flip flops, finished packing my bag for the day, grab the money off the kitchen counter Dan's dad left for me, the keys for the condo then went out into the drive to wait on the cab. Just before 9 o'clock, I was lying in a chair on the beach face up to the sun. I was already getting some nice tan lines and since this bikini was smaller, it was showing those lines and attracting some much wanted male attention.

Naturally I immediately started to consider removing my top. I really shouldn't because Dan wouldn't like it and I'm not sure I am comfortable with strange men looking at my naked body; even though the thought is exciting, the reality could be very much different. By 10 o'clock I had decided to untie the bikini top and just leave it sitting over my nipples. A short time later the two pretty, thirtysomething women Dan had been spying on the first day returned and set up on the beach a little in front and to the left of me. They immediately removed their tops and resumed chatting. For the first time I also noticed they had wedding rings. Well, if two married women can expose their chests, then why can't I? With that thought, my bikini top went into my bag.

Almost immediately I noticed two guys glancing my way when I removed my top. I felt the moisture between my legs start immediately. It was so thrilling to be almost naked in front of a crowd of total strangers! Then I reached in my bag and pulled out the suntan lotion. My only thought at that moment was that I didn't want to get sunburn on my exposed boobs. How would I explain that one to Dan? But when I laid back and started to rub the lotion onto my breasts, I realized it looked like I was actually playing with my boobs in public and that made me even more aroused! I wasn't the only one. As soon as I started to rub my boobs, I got twice the male attention I was getting before and I became twice as excited; so as I rubbed, I began to squeeze my nipples between my fingers. Just a little bit, I didn't want to make it obvious I was getting off; I just wanted it to appear as though I was an oblivious sunbather rubbing on lotion.

Just as I was finishing up with the lotion, a very handsome middle aged man walked over carrying a lounge chair in his left hand, had a can of beer in his right hand and a towel draped over his right arm.

"Do you mind if I setup shop here?" he asked indicating an empty spot just to my left.

"Not at all," I somehow managed to squeak out through my flustered embarrassment.

This man was very good looking. Probably just over six feet tall, dark brown hair fringed with some gray, muscular looking chest, arms and shoulders; not to the extent of looking like a gym rat but rather someone who just takes care of themselves, curly brown and gray chest hairs and a dark tan like someone who's already been here for a week or two.

I probably turned bright red at that moment when I realized my chest was completely exposed to a man who could possibly be the same age as my dad. With that thought, I was almost paralyzed with fear and indecision. Should I cover myself up? What if covering up was a signal to him that I am uncomfortable and makes him leave? I really don't know why but even in my state of near panic, I wanted him to stay. But as he setup his chair and towel and prepared to recline, I noticed he didn't appear to be ogling me like the others. At least if he was, he was very good about being discrete; even while wearing sunglasses. As he reclined, I noticed he was wearing a wedding ring. Maybe that was it? He is so in love with his wife that he doesn't pay attention to other women; even one half his age lying almost naked on the beach? No; if anything, he views me as a child and is a decent man immune to temptation.

As we soaked up the rays I began to think about what it would be like have a man like him naked and on top of me; inside of me. Many times I have wondered how it would be to have an older, experienced man make love to me. I glanced down at his bulge then back at his face. If he saw me look at him, he made no indication.

"So what have you experienced since arriving in Key West?" he asked me breaking the silence a few minutes later.

"Wha...? Oh... how did you know... I mean..." I was stammering and flustered again. He surprised me when he broke the silence and I was taken off guard a little by his question.

"Well, most people come here for vacation so I just assumed," he spoke again.

"Oh; I'm here with my boyfriend and his dad and so far we've gone to sunset festivities, shopped Duval and hung out at the beach." Damn! Why did I tell him I had a boyfriend? He looked over at me for the first time and then he looked around like he was searching for someone.

"He and his dad went deep sea fishing; I think they said in Key Largo or somewhere?" I said when I finally understood what he was searching around for.

"Fin and Feather?" he asked.

"Yeah, I think that's the one."

"I've used them before. They're very good. Your boyfriend and dad should catch something; maybe even a sailfish."

This man was very kind and easy to talk to. No goofy come-on line, no asking me why I'm alone or didn't go with them. Just easy conversation and I liked it.

"How long have you been here?" I asked.

"My wife and I came down about a week ago. We both had two weeks of vacation time to burn and our son decided to stay up at school and take some summer classes."

"She's shopping or something?" I asked and then immediately wished I hadn't. I didn't want to give the wrong impression.

"No, she drove up to Miami this morning to see her sister. We live in Atlanta and rarely ever get this close for a visit. She'll drive back tomorrow night."

I was wondering why he didn't go with her but I didn't ask. Maybe he doesn't get along well with his sister-in-law though by first impressions I find it hard to believe anyone wouldn't get along with this man. I could tell by his demeanor he was laid back and easy going. He was even a little soft spoken with a very kind voice.

We sat in silence for a while then he slowly began to sit up, straightening his towel as he did so. At first I thought he was going to turn over to sun his back but then he looked over at me and said, "I'm sorry, I should have introduced myself. I'm Rick," he said as he held out his hand.

Nervously now, I sat up and shook his hand, giving him the full frontal view of my perky little boobies as I did. Again, if he noticed them, he didn't make a spectacle of glancing down and gawking straight at them like most men do. "Hi, I'm Jenny," I replied.

"Listen, I'm getting kind of hungry; are you?" He asked. Without waiting for my reply he then offered to buy some food for me at the pub/bar/grill place that was here on the beach. Flustered again, all I could get out was, "Sure."

"Okay, let's do it!" he said as he reached down and pulled a T-shirt from under his towel. As he slipped on his T-shirt, I pulled on my shorts and put on my tank top over my bare breasts not even bothering with the bikini top.