An Adventurous Tomboy with A Quiet Guy

(Female POV)

I giggled to myself as I stared at the doors of the beach house we had been invited to for the summer.

I had my suitcase with, lets just say interesting outfits. Generally I stick with practical outfits, mainly shorts as I enjoyed the looks my legs would receive.

It made it easy to know which guys were 'thigh guys' as I had almost no breasts. But not having a significant weight hanging off my chest made it easy to chose clothes.

When I was younger I cut my hair so I could pass as a boy. I had abused that a few times to sneak into the boys bathroom, that lasted up until my breasts came in. Though they were small it made it impossible to pass as a boy anymore. Though I took a liking to the clothes which was why I mainly wore shorts.

But back to the present, I was given the option to attend some kind of gameshow. But I had read the fine print. There was plenty of 'We're not responsible for any consequences of sexual intercourse' It was thrown around at least three times in the papers I signed, sure it was disguised and hidden fine print but it was there.

To that end I made sure to pack those outfits I mentioned, and right now I was wearing shorts that really showed my ass.

Then the presence of my boyfriend arrived reminding of the little stipulation for this no doubt wild summer. I had to bring him. I would have definitely preferred coming here for an entire summer of kinky sex and returning as if nothing happened. Wouldn't be the first time I went and fooled around, my boyfriend... He just wasn't very fun in bed.

I shook the thoughts from my head. Sure he was boring in bed but he was courteous and sweet out of it. That and he will do what I tell him. I had him wear one of my panties once just to prove it.

I turned to look at him. He was the same height as me but he had a habit of looking at my thighs so by looking down he lost some height. But his stature as it was kept flashing back to why I kept him as my boyfriend. He might not be what typical women want in a guy, especially the way he flushed red whenever there was even the lightest attention on him. But his blushing face was what kept me with him for some reason, it was just cute...

He had light brown hair, slightly long. Not quite as long as mine, I had been growing it out since my last fling. The guy wanted to try hair pulling, I certainly don't regret it even if I couldn't sit from how hard his slaps were on my ass.

Shit I was getting wet thinking about it. I tore my mind away from the muscular guy who I occasionally spend nights with and back to my boyfriend.

Smiling I spoke. "Hey you might not want to stare too much at the others. But you're free to stare at me." I said that last part while ensuring I swayed my hips as I walked into the door excited to see who I was going to enjoy spending time with. Mainly the guys I would sneak away with.

Only after opening the door revealed... nothing? Well Almost. There was a serious woman in a modest dress, She had the serious expression of an employee.

"Ah, Shari and Zack. Here are your room keys, please get settled in while the rest arrive." She handed us each a keycard. I noticed that they were different keys. We got separate rooms?

"We are getting separate rooms?" Her eyes gained a fun glint in her eyes I could relate to as I swear the corner of her mouth tilted into a smile.

"That is correct. Each person has their own room." Well. That works for me. Makes it easier to sneak off without alerting my boyfriend.

I just nodded but my boyfriend gave me a glance and continued to ask questions.

"What if we want to sleep in another room?"

I waited for the answer. "Then you will have to ask to be let in." She shrugged casually. I found my gaze was locked to her breasts... Even though her modest dress didn't draw attention to it she was still a stunning woman.

However it wasn't just me. It was also Zack! I grabbed his arm in a pinch pulling him away. "Come on we got to get settled."

Once we were out of earshot of her I growled at him. "What are you doing looking at her so blatantly? Don't think I'm going to be letting you sleep in my room if you keep that up." Not that I was going to anyways but this was a good excuse to keep him out of my room. All I had to do was feign some anger at him.

"Ah- No no I wasn't looking she just pushed her tits into my face!"

"So you were looking at her tits! Then you can spend a week not sleeping in my room thinking about how large they were."

Ok, maybe it was a little bit of an insecure thing for me. Not only did I lose the perks of being small chested but I also never got benefits of the large chest as well.

So I closed the door on his face to check out my room. Oh yeah... This game or whatever is definitely some type of sex thing. I eyed the overly large bed as there was only one reason to give everyone a large bed. They wanted us to bring others into our bed.

I hope the other guys aren't like Zack. At the very least a large cock will do. As a back up I had packed my trusty friend, A big purple dildo with a very grotesque shape, it wasn't shaped like a human's cock but some kind of fantasy creature. I mainly got it because I was curious about the spines that ran down the length. Since then its been my only consistent lover.

I smiled as I pulled it out of the suitcase. The tingle of anticipation grew until I couldn't take it and I was kicking off my shorts and underwear before I jumped on the bed. I spotted a large mirror on the opposite wall. I had never really used a mirror to watch myself before, and the idea was interesting.

(Male POV)

My girlfriend dragged me to this beach house. Apparently she signed us up for some beach vacation, she was very light on the details but I came along anyways.

I looked at her ass as she didn't wait for me at least not right away. She rarely wore shorts this tight... Usually only when she was going out to spend time with other guys. Yeah... I knew she was doing it. One of her... Boyfriends... was an old friend of mine and he sent me many many photos and videos.

At first I was angry at him then her but seeing her smiling face covered in cum of my friend... I didn't have the heart to tell my friend that she was my girlfriend. Instead I had quietly accepted my roll in our relationship, if anything I had come to actually like imagining what she was doing.

Though most of the time I didn't get a message from my friend whenever she went 'missing' so she must have multiple people she spends time with. She was actually very good at hiding her acts so I was very surprised she brought me here. I thought she'd have played it safe and left me at home while she ran wild over the summer.

We had had sex a few times... But after the first few times it dropped off quickly. That was around the time she started going 'missing' But I didn't notice then completely oblivious. Now if we do have action she puts me in her panties and I use her favorite toy on her. There was no way my three inches could compare to her literal ten inch monster cock, so there were no delusion of me being able to turn her around with my great prowess.

At least she was practicing safe sex. I once spotted an empty box of condoms, meaning that she had used them all up. But still looking at her... I just couldn't imagine her with her legs wrapped around anyone, even if I knew she was doing just that.

I tore my gaze from her ass walking up next to her where she stopped to gaze at the house. I could tell she noticed me, I snuck a glance at her chest. Yeah. indeed. She was pretty small, I knew it was a bit of contention with her as she would blow up if you even hinted at her lack of size.

She let out an imperceptive sigh before addressing me "Hey you might not want to stare too much at the others. But you're free to stare at me." She walked away mid speaking and I found my gaze on her ass as it shook and squeezed in those shorts.

I followed after that ass like a little duckling into the building.

She stopped not to far into the building the reason apparent. It was the stunning woman. In all honestly she looked like a mature version of her. But being older that meant more mature... and it showed. Her chest still small but more defined, her hips wider. Her height taller. And her expression utterly unreadable.

I found myself swallowing dry when her eyes lighted upon me. I was... trapped under gaze. Unable to to escape, I felt like she was about to do something to me even if she had done nothing.

I almost jumped when her hand held out some cards to us. "Ah, Shari and Zack. Here are your room keys, please get settled in while the rest arrive."

I snatched the card from her fearing she would bite me.

Almost immediately my girlfriend asked a question. "We are getting separate rooms?" What?

I looked at her card... Sure enough it had a different number on it.

Even though it was in the same clinical tone I still couldn't help feeling her words were malicious. "That is correct. Each person has their own room."

I saw the smile bloom on my girlfriend's face. I could connect she was not going to be inviting me.

But I needed to confirm. "What if we want to sleep in another room?"

She shrugged as she pushed her chest towards me. "Then you will have to ask to be let in." Fuck she had no bra on! I could see her nipples pushing up the dress. But despite that her serious tone made me aware she knew that my girlfriend wouldn't be inviting me at night.

Then I got pinched and was being dragged away from the dangerous woman by my Girlfriend. When I looked back I was chilled seeing her grin that I actually kept pace with Shari. She had an energy in her step that made it hard to keep up normally.

I could feel the cold sweat on my back as I suddenly felt like I dodged a deadly bullet when my girlfriend turned to me in mock anger. Not actually angry but was taking advantage of the situation for the excuse.

"What are you doing looking at her so blatantly? Don't think I'm going to be letting you sleep in my room if you keep that up."

The thought of that stunning and hot woman was amazing but I feared her personality... Words then spilled out of my mouth remember that strange malicious attitude I noticed on the woman.

"Ah- No no I wasn't looking she just pushed her tits into my face!"

"So you were looking at her tits! Then you can spend a week not sleeping in my room thinking about how large they were." Ah now she was actually angry. I really shouldn't have mentioned the breasts... Even if she was bigger she would think I was comparing them.

I shook my head as she closed the door to her room. Conveniently my room was right next door. I started at the wall that we shared and spotted a rather large mirror...

A mirror? It's too large to be for just the girls. I put aside the strange mirror for now and addressed the strangely large bed... It was too much for just one person. I pressed my hand on it a few times, it sure is soft though. Its a high quality bed.

I was putting my things away when I saw movement. Movement? When I was alone? I turned with a start only to freeze at what I saw...

The mirror was no longer a mirror... It was a window letting me see into my Girlfriend's room... I swallowed. She was with her favorite dildo in hand as she was preparing to use it on herself. But the entire time she was staring at what for her must be a mirror...

But it still made me think she was staring at me when she pushed the big toy into herself.

I mechanically shoved clothes into places as I was too busy staring at my Girlfriend pleasuring herself. But then just as her mouth opened to let out a moan she in a panic sat up shoving her dildo under the pillow of the bed as she shoved her hands into her crotch looking at the door.

I heard the knocks too then the window quickly turned back to a mirror and strangely the sounds were cutoff as well. But I figured I knew what was coming next...

A few moments later... *Bap *Bap *Bap The sharp knocks told me all I needed to know... It was that woman again. But instead of me opening the door for her it opened and she stepped in.

Of course she had a key...

Then she closed the door behind herself and I felt trapped. She no longer had the serious expression. Instead she was smiling at me... And that scared me.

I didn't notice the situation until I was backed up against the wall with her over me. Then her tits pressed against me.

Her whisper towards me shook me. "Hmm~ You are soo cute." But after her hand brushed my cheek her tone reverted to the more serious tone that I actually preferred now that I heard her honeyed seductive voice just now.

"I am here to inform you that dinner will be here soon." Now that business was over she spun around and left the room the door clicking shut behind her leaving the room full of her seductive scent.

I stepped forward slowly. Unsure if she was really gone then back to the mirror and not seeing anything strange about it decided I needed to get out of this room full of her strangely lingering scent.