A Daughter's Vacation Being Free

Note to reader: All characters are at least 18-years-old even if not specifically stated in the story.

We arrived at the resort mid-morning after an overnight flight and shuttle ride. The resort sat on a beautiful beach with very blue, clear ocean waters. The resort was large and featured numerous restaurants, dance clubs, recreational activities, and secluded areas. My parents had insisted my sister and I take this trip with them despite us both being adults. I was 25 years old and still living with them in the house I grew up in. After giving college a try for a year, I ended up dropping out. Temporarily I said at the time, but six years later I had no plans to return. Instead I am continuing to live at my parent's house in my old bedroom. I'll take the odd job here and there but most days I am hanging out in my room playing on the computer. My life is mostly filled with writing fan fiction, playing Runescape, and arguing on Reddit. In high school I was very popular and had a long term boyfriend. But after I dropped out of college, my friends gradually moved on to jobs and marriage. My boyfriend broke up with me claiming I had given up.

Since then I've had a few dates, but generally don't meet a lot of guys. It's not that I'm unattractive. Both my sister and I have inherited my mom's D-cup breast. My ass sticks out more than I'd like but I only weigh 140 lbs at 5 feet, 6 inches tall. I think I'm better looking than some of those girls I regularly see on amateur porn sites.

I felt a bit like a loser going on a vacation my parents paid for while in my early twenties, but I had nothing else going on so I agreed. My younger sister, Jenna, also is coming, but she is 18 years old and a few weeks away from starting her senior year in high school. She's smart, gets great grades and the whole family is excited to see her become a doctor or something. She also has been dating the same guy for the last 5 years believe it or not. They are so cute together and her boyfriend, Rick, has secretly told my parents that he plans to propose at their high school graduation in May. Rick is very sweet and kind. So much so that Jenna has told me that despite dating half a decade, Rick respects her too much to push for sex. They haven't seen done oral or even seen each other naked at all. My parents offered to bring Rick along, but he thought it would be inappropriate for them to be sleeping in the same hut, so he declined.

My mom and dad carried the luggage from the shuttle while my sister and I followed. My dad was very protective of his family. I think he actually likes me living at home where he can watch over me. However, he can be a bit controlling. Even at my age he has strong opinions about what I should wear and generally I just follow his suggestions and dress rather conservatively. My mom, despite being in her mid-forties, looks great. She is currently wearing a long sundress. Like me she is a curvy woman and gets a lot of male attention, causing a lot of arguments between my dad and these men.

We got check in and found our room. Dad suggested we tour the resort, which we did. After an hour we got lunch at one of the restaurants before heading back to the room. After settling in, I announced my intention to head back out.

"I saw some people my age hanging out at the beach. I'm going to head out and maybe make some vacation friends."

My dad, ever protective had questions. "What are you going to wear?"

"Well, they were on the beach, so probably a swimsuit," I said feeling embarrassed by the question.

"Wear a one-piece with shorts," he commanded.

As usual I did what he said and wore a black one-piece bathing suit that did very well covering up my entire top. Over them I wore some blue jeans shorts. I waved goodbye and went out seeking the college age group I saw before.

The group of five guys and one girl were right where I had last saw them on the beach. I neglected to tell my dad the ratio of men to women, but he'll live.

"Hi, do you mind if I hang out with you? I'm Lena," I said as an introduction to the group.

They were very welcoming and cool. They were from all over the country and had met only the day before.

"I like your outfit," the other girl said smiling at me.

I appreciated the compliment but was jealous of the black bikini she was wearing. While I wasn't ignored, the guys were paying more attention to her which I attributed to her outfit showing a lot more skin than mine. We talked about a variety of things and I tried to ask a lot of questions and engage in all of the topics, even the ones I didn't have interest in. The only person who seemed to be engaging with me was the other girl who I think was aware she was getting the majority of the male attention. Eventually we all needed to leave but agreed to meet back in 2 hours at the same place.

I got back to the room and dad had a lot of questions about what I did and what the other guys were like. I answered his questions to his sanctification and told him about my plans to meet up later, which he wasn't happy about but didn't object. As a family we headed down to the beach for a while and waded in the water. My mom, sister, and I all wore our one-piece swim suits that dad specifically approved of. It was enjoyable, but I was looking forward to being with people my own age again soon. We headed back and I had about 20 minutes until the next meet up with my new friends was due.

Getting ready, I stood and looked at myself in the mirror wearing the same one-piece bathing suit. I look so frumpy when I'm wearing it. Olympic swimmers show more skin than this. I wasn't looking to have the guys clawing at me, but it would be nice to get close the same level of attention as the girl in the bikini did. Like I said, I'm an attractive woman. I walked over to where my dad and mom were sitting.

"Dad, I want to wear the bikini I brought to the beach, okay?"

"What? Why? I didn't even realize you brought or owned a bikini. What's wrong with swimsuit you have on," he protested.

"I'm not looking to do anything bad, I just want to wear something that matches more what people my age are wearing. Did you see anyone my age out there dressed like me? I didn't."

He continued to argue, "You told me all you guys did before was talk. Are you not able to talk in that swimsuit? What are you doing where you need to show off your body?"

It was no use, he wasn't going to give. Unexpectedly, my mom spoke up, "Honey, remember I use to wear bikinis when I was her age? She's 25. It's not like she is wearing tassels and a thong out there. She'll be okay."

Dad looked unhappy but I think mom speaking up made the difference. "Be careful out there."

He couldn't get himself to say yes to the bikini, but he wasn't forbidding it. I went to the bottom of my suitcase, grabbed it and went to the bathroom. It was a pink 2-piece bikini. It was far from the most scandalous bikini one could wear. It covered my butt and about 80% of my chest, which was very large. I took a final look at myself and then tried my best to rush out of the hotel room before dad could see me and change his mind.

Walking outside was exciting for me. It was true that lots of other women were wearing bikinis. But for me, this was the most skin I have shown outside in a while. I was excited for the guys to see me wearing this. I was a few minutes late to the beach but the five guys and single girl were all already there.

The first guy to see me did a double take before declaring, "Hey, awesome suit! What was your name again, sorry."

"It's Lena," I said with a smile and probably a bit of blush showing in my cheeks.

Everyone greeted me and I instantly felt like I was ten times more welcomed than previously. The other girl and I were invited to tell stories, jokes (which always got a laugh) and answers to a whole bunch of questions. I talked for almost 10 minutes about Runescape despite me being the only one there to have ever played it. I think I actually got more attention than the other girl, which I attributed to me being curvier than her. Not that it's a competition.

After a joke I gave that got a loud round of laughs, one the guys looked at me and said, "Lena, thanks for hanging out with us. I was worried this trip would be dull, but with you around it's been a blast."

The guys all agreed and the girl lightly nodded. "I really hope you can keep hanging out with us. Oh, I meant to bring you a gift from the gift shop, but I forgot. I'll do that next time," another guy mentioned. Several of them mentioned a similar sentiment of wanting to bring me a gift next time. I was almost blushing from the attention.

"Hey Lena, did you know that you are actually allowed to go topless anywhere at this resort?"

I paused upon hearing this. That was an odd thing to bring up.

"Is that true?" I asked not knowing how else to respond.

A different guy answered, "It is, take a look at that sign behind you."

I turned around and saw a large sign with a variety of rules. Scanning down the list, I found a bullet point that read, 'Male and females are allowed to be topless anytime at any location, public or private, indoors or outdoors, anywhere on the resort grounds.' I guess it wasn't too surprising. This was an adults old only resort, however it was not advertised as being sexual in any way.

"Huh, that's interesting. I haven't seen any woman topless though."

The other girl spoke up, "Yeah me either, I don't think anyone actually does that here."

I thought the topic had died, but another of the guys brought it up again.

"True, but that doesn't mean someone can't. Have either of you ladies ever done anything like that."

We both shook our heads no. "There's no way I could do something like that, it would be too embarrassing," I said while the other girl nodded in agreement.

"Embarrassing? Why in the world would you be embarrassed? You are gorgeous! When you walked over here in today, just seeing you took my breath away."

My heart may have skipped a beat hearing that. It had been too long since any guy had given me a compliment like that.

"Thank you for saying that. But I just don't have the courage to show off my body. Even wearing this is a stretch for me," I said becoming very aware of the male attention I was getting.

"As beautiful as you are, you should have the courage to do anything. I say go for it!" He said starting a clap.

The girl spoke up, "Guys don't push her to do anything that makes her uncomfortable." She was completely ignored.

"You... you guys really think I should?"

"It's your choice gorgeous. But I think you are as brave as you are stunning."

I looked around the group. Each guy was giving me their full attention and showering me with compliments. The girl looked uncomfortable, but the guys had giant smiles. Was I really going to take off my bikini top outside, in front of all of these guys? Half an hour ago I was nervous wearing a bikini. I looked around the area, nobody else was nearby, so only these guys would see me if I did it, which I wasn't ready to say I was going to. These guys lived nowhere near me. In a few days I would never see them again, and none of them had any phones or cameras. I would make their day and feel beautiful in the process.

I reached my hand to the back of my bikini which drove the guys to yell in excitement. They started chanting my name together. I felt my top unhook but grabbed the front with my arm before it could slide off. I was standing nearly topless in front of these guys. All I had to do was move my arm away and they could see every inch of by breast. I paused in this position and began having second thoughts.

"Are you guys sure I should do this?" I asked despite knowing what they would say. They responded as expected. Knowing there was no way I could back down I got a bit playful with it, primarily to hide my shyness.

"Hmmm," I said looking up with a thinking face. "Okay!" and I rapidly pulled the top away revealing my tits to 5 guys and a girl I had just met today.

The guys stared in silence for an uncomfortable amount of time.

"Are you guys okay? Is there something wrong with my chest?" I asked nervously.

"Oh my gosh, no. Sorry. I think we were all just mesmerized by your body. God you are hot. Thank you so much for doing this."

With that, the silence broke and I was showered with more and more compliments, albeit with less eye contact than before. The other girl was looking more uncomfortable and was obviously looking away from me as she had no interest in my bare boobs. I felt bad.

"Listen, please don't feel pressured to take your top off just cause I did. It's fine, truly."

She gave me a judgmental look. "I wasn't going to," she said coldly while shaking her head.

I almost called her a bitch but the five guys were giving me their full attention while ignoring her completely. That's all the response that was needed. She left a few minutes later, not that anyone noticed.

I kept hold of my bikini in my hand. I needed the comfort knowing I could cover myself back up if I ever felt the need. But otherwise I was good staying exposed. I moved the conversation away from my tits and started talking more about my interest. Everything I brought up the guys wanted to know more about. Every comment I said was either very interesting or very funny to them. I felt like I was fast making very close friends. My confidence was soaring and I found myself putting my hands behind my back and sticking my chest out more and more.

It was starting to become dusk and I realized I needed to head out. The guys were disappointed but told me later tonight they were going to set up a bond fire at the beach and they begged me to come. I agreed which got cheers from them.

One of them then asked, "Will you... you know.. be..." he said motioning to my bare chest.

I gave a small smile but didn't give any other indication. Was this a one time thing or was I going to be topless in front of these guys every time from now on?

"Yes... but after I get here. No way am I walking around the resort without a top."

I accepted that I was going to be topless tonight but not worrying about my lack of attire at future meet ups yet. I waved goodbye as the guys walked off in separate directions. I turned around, prepared to put my top back on but was met with the sight of my mom, dad, and little sister staring at my tits.

"Were you stripping for those boys," my Dad yelled.

I looked around to see if any of my friends had maybe heard that but thankfully they were out of earshot. "I was not stripping dad!"

"Then why were you letting them ogle your naked chest?" I don't think I've ever seen him this upset.

"They weren't ogling me dad. I just wanted to get some sun and enjoy the breeze. It's not a big deal. It's allowed in the resort rules, look," I said pointing defensively at the sign.

Dad didn't bother looking while mom looked with interest. "You didn't let them touch you did you," dad asked nervously.

I stamped my foot down causing my still naked boobs to jiggle, reminding me I was still topless. I began putting my bikini back on angrily replying, "Of course not. This wasn't a sex thing. Women go topless all the time in some places. Also it's not against the rules!"

I had gotten the suit over my boobs and was working on connecting the hooks in the back.

"Nobody else in this whole resort is topless. Just you!" Dad was not cooling down.

"I wasn't going to walk around and let everyone see me. I just did it around my friends."

After finally hooking the back, I adjusted the top as my left nipple was poking out.

"Aha! So you only wanted these particular boys to see your chest! That sounds sexual to me!," Dad declared, trying to trap me.

All I could do was growl in anger. "Let's head back to the room and cool off," mom suggested. We all walked back in angry silence.

As soon as the door to our room closed, the argument started back up.

"Put away that bikini. For the rest of the trip if you want to wear a swimsuit, you can put on the one-piece with a pair of my trunks over the bottoms," dad said thinking that would end the conversation.

"I'm 25 years old dad. You want me to wear what shy 10-year-old girls wear to the pool. I'm meeting the guys later tonight at the beach and I'm wearing my bikini." I wasn't going to dream about going topless again, but I wanted to at least wear a bikini.

"I will not have my daughter acting like a whore," he yelled slamming his fist on the wall. The room went silent.

Mom looked at me and asked, "Tell me the truth Lena. Did you promise those boys if you would go topless again tonight?"

I took a big breath before answering. "Yes, yes I did."

Mom smiled, "Then you'll go to that meeting topless tonight."

"WHAT! Are you insane? Those guys are going to take advantage of her," Dad was as shocked at me about her response.

"Dad, listen. Yes the guys enjoyed seeing me like that. I'll admit it. But I haven't felt that beautiful or respected in years, if ever. Sometimes a woman needs that."

Dad wasn't having it, "Guys can complement you without being able to see your naked tits!"

Mom spoke again. "I will be going with her to the meeting. I will ensure she stays safe."

Oh great, that's what I need is a chaperon I thought.

"I will also be going topless, wearing only my bikini bottoms."

That's... not what a chaperon does.

"WHAT! You're going to parade topless in front of 5 strangers," dad was looking pale.

"It's like Lena said, women need to do these things sometimes to feel good about herself. I'm a woman too."

"I'll compliment you all you want," dad pleaded.

"Oh honey, that's not the same. Relax. It's not like I'm doing this in front of our neighbors. We will never see these boys again. I'm not going to let them touch either of us. Come on honey, take off your top and let's get ready to go." Dad had no response. He sat down in his chair and stared at his hands.

I wasn't planning on walking from the room to the meeting site at the beach topless. But at this point bringing that up seemed like a bad idea. Mom unhooked the back of my bikini and I was topless once again. Mom left to her room and 30 seconds later came back wearing only her bikini bottoms.

"Oh dear god in heaven," dad said when she entered.

I had no memory of ever seeing my mom's breast. She had the breast of a woman 15 years younger than her, it was impressive. It wasn't until she turned around that I realized I had been staring at her tits since she entered the room. That also made me appreciate how awkward it was going to be showing up to meet my new friends with my topless mom in tow.

"Okay, we are off," mom said opening the door and introducing the resort to her tits.

I gave dad a last look before I followed, "We'll be safe, I promise."

As we exited the room, I was finally able to talk to mom one on one. Not something we get a lot of chances to do and especially not something we do while both topless outside.

"You don't have to do this mom, you can go back in now," I said.

"Honey, I wasn't kidding earlier. This is just as much for me as it is for you. I want to feel admired and wanted as well."

"Okay, but just so you know these guys are my age. Early twenties probably in college."

Mom laughed, "And you're worried they won't like me there, especially topless. I think you'll be surprised." I gulped and started walking.

I had hoped with it being nighttime that the walk to the beach would be void of people, but that was not the case. Not only that but the pathway was well lit. Walking by group after group of fellow guest, I tried to cover myself without making it look like I was covering myself. It was a poor attempt and everyone got an eye-full of my chest that walked by. Mom, on the other hand, made no such attempt. She confidently walked as her massive tits swayed with her. She would make casual conversations with people we passed by, even as they noticeably stared at her and her daughter's naked tits. By the time we got to the beach, the number of people who have seen my nude breast in my life must have increased by at least 10X.